918:
86:
945:
980:
1038:
1068:
2307:
2158:
2226:
2063:
794:, is found in some marine foods such as fish and algae, and also in mushrooms in larger concentrations. The average person's intake is about 10-50 ÎĽg/day. Values about 1000 ÎĽg are not unusual following consumption of fish or mushrooms. But there is little danger in eating fish because this arsenic compound is nearly non-toxic. Arsenobetaine was first identified in the
1011:
219:
AsO(OH) (R = alkyl or aryl). Cacodylic acid, central to arsenic chemistry, arises from the methylation of arsenic(III) oxide. (In contrast, the dimethylphosphonic acid is less significant in the corresponding chemistry of phosphorus.) Phenylarsonic acids can be accessed by the reaction of
1669:
Mancini, Ines; Guella, Graziano; Frostin, Maryvonne; Hnawia, Edouard; Laurent, Dominique; Debitus, Cecile; Pietra, Francesco (2006). "On the First
Polyarsenic Organic Compound from Nature: Arsenicin a from the New Caledonian Marine SpongeEchinochalina bargibanti".
1480:
Styblo, M.; Del Razo, L. M.; Vega, L.; Germolec, D. R.; LeCluyse, E. L.; Hamilton, G. A.; Reed, W.; Wang, C.; Cullen, W. R.; Thomas, D. J. (2000). "Comparative toxicity of trivalent and pentavalent inorganic and methylated arsenicals in rat and human cells".
1630:
Alice
Rumpler; John S. Edmonds; Mariko Katsu; Kenneth B. Jensen; Walter Goessler; Georg Raber; Helga Gunnlaugsdottir; Kevin A. Francesconi (2008). "Arsenic-Containing Long-Chain Fatty Acids in Cod-Liver Oil: A Result of Biosynthetic Infidelity?".
579:, equilibrate between three-, four-, and five-membered rings, but bulkier substituents usually settle on a four-membered configuration. Synthesis is typically by reductive dehalogenation with a metal.
765:
is the methyl donor. The methanearsonates are the precursors to dimethylarsonates, again by the cycle of reduction (to methylarsonous acid) followed by a second methylation. This dimethyl compound is
1603:; Brian W. Skelton & Allan H. White (1977). "Isolation, crystal structure and synthesis of arsenobetaine, the arsenical constituent of the western rock lobster panulirus longipes cygnus George".
725:
As arsenic is toxic to most life forms and it occurs in elevated concentration in some areas several detoxification strategies have evolved. Inorganic arsenic and its compounds, upon entering the
623:
Arsenic-arsenic bonds are very weak, and oligomeric arsenic compounds are even more liable to oxidize than their hydrogenated precursors. The following reaction can, however, be prepared through
96:
Surprising for an area now considered of minor importance, organoarsenic chemistry played a prominent role in chemistry's history. The oldest known organoarsenic compound, the foul smelling
669:, decomposing spontaneously in the absence of a vicinal carbonyl. Stabilized ylides olefinate to a mixture of stereoisomers, whereas unstabilized ylides tend to epoxidate (like a
1178:
1741:
1567:
558:
bonds are rare. They are observed in the gas phase but considerable steric protection is required to inhibit their conversion to oligomers as liquids or solids.
65:. In general these applications are declining in step with growing concerns about their impact on the environment and human health. The parent compounds are
917:
345:) is known. Reduction of the chloride derivatives with hydride reducing reagents affords the corresponding hydrides, such as dimethylarsine ((CH
1374:
1329:
1218:
1398:
Toshikazu Kaise; Mitsuo Ogura; Takao Nozaki; Kazuhisa Saitoh; Teruaki
Sakurai; Chiyo Matsubara; Chuichi Watanabe; Ken'ichi Hanaoka (1998).
264:
1734:
1416:
1399:
1195:
2439:
733:. Organoarsenic compounds arise via biomethylation of inorganic arsenic compounds, via processes mediated by enzymes related to
1727:
1292:
1161:
1067:
1582:
1308:
Reimer, K. J.; Koch, I.; Cullen, W. R. (2010). "Organoarsenicals. Distribution and transformation in the environment".
1230:
Maier, L.; Rochow, E.G.; Fernelius, W.C. (1961). "The direct synthesis of organoarsenic and organoantimony compounds".
815:
are also known. Although arsenic and its compounds are toxic for humans, one of the first synthetic antibiotics was
2296:
2291:
2286:
2281:
2276:
2271:
2266:
2261:
2256:
2251:
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2231:
2174:
2068:
1989:
1984:
1841:
1104:
742:
2332:
2034:
2004:
1994:
1974:
1962:
1930:
1895:
1863:
1831:
1826:
1786:
837:
Organoarsenic compounds may pose significant health hazards, depending on their speciation. Arsenous acid (As(OH)
624:
1801:
1765:
1719:
2377:
2372:
2367:
2362:
2357:
2352:
2347:
2342:
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2322:
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2138:
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2118:
2103:
2083:
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1957:
1940:
1890:
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1880:
1875:
1851:
1811:
670:
655:
2327:
2317:
2128:
2113:
2098:
2088:
2073:
2014:
1999:
1979:
1969:
1950:
1945:
1925:
1868:
1836:
369:
247:), is a precursor to fungicides (tradename Neoasozin) in the cultivation of rice and cotton. Derivatives of
112:. Various other organoarsenic compounds formerly found use as antibiotics (Solarson) or other medical uses.
101:
1806:
1796:
2236:
2151:
2093:
2056:
2051:
2039:
2019:
2009:
1915:
1910:
1905:
1846:
1821:
1483:
1353:
Dopp, E.; Kligerman, A. D.; Diaz-Bone, R. A. (2010). "Organoarsenicals. Uptake, metabolism and toxicity".
944:
507:
2044:
1856:
1791:
1781:
274:. These applications are controversial as they introduce soluble forms of arsenic into the environment.
53:. A few organoarsenic compounds, also called "organoarsenicals," are produced industrially with uses as
628:
2123:
2108:
1920:
1900:
1094:
1037:
964:
795:
759:
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334:
2024:
617:
570:
236:
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85:
1508:
539:
248:
191:
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1687:
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1500:
1462:
1380:
1370:
1335:
1325:
1288:
1214:
1191:
1157:
1099:
646:, but arsine(I) rings may instead insert the bond into the ring. In general, arsines are less
372:, methyl halides react with elemental As, as illustrated in the following idealized equation:
38:
136:. Correspondingly, organoarsenic compounds are commonly found in these two oxidation states.
1679:
1640:
1612:
1546:
1538:
1492:
1452:
1444:
1411:
1362:
1317:
1280:
1239:
1183:
1137:
647:
551:
310:
229:
1600:
933:
755:
747:
698:
666:
651:
503:
499:
314:
121:
1529:
Cullen, William R.; Reimer, Kenneth J. (1989). "Arsenic speciation in the environment".
766:
751:
405:
365:
268:
173:
1616:
1457:
1432:
758:. Thus, trivalent inorganic arsenic compounds are methylated to give methanearsonate.
281:
organic ligands are rare, the pre-eminent member being the pentaphenyl derivative As(C
2433:
2396:
1243:
1079:
1026:
956:
827:
787:
729:, are progressively metabolized to a less toxic form of arsenic through a process of
306:
183:
165:
148:
42:
979:
404:
Another route to dimethylarsenic compounds begins with reduction of the As compound
100:
was reported in "cacodyl" (1760) and is sometimes classified as the first synthetic
1512:
1448:
697:
Organoarsenic compounds, especially those featuring As-Cl bonds, have been used as
566:
221:
109:
70:
1187:
1321:
1052:
823:
804:
734:
730:
702:
643:
488:
74:
54:
573:
at As and have formal oxidation state As. Small substituents, such as in (MeAs)
17:
1366:
894:
889:
800:
726:
555:
995:
816:
562:
105:
62:
58:
34:
1691:
1683:
1652:
1644:
1504:
1466:
1384:
1339:
479:
A variety of heterocycles containing arsenic(III) are known. These include
1496:
1417:
10.1002/(SICI)1099-0739(199704)11:4<297::AID-AOC584>3.0.CO;2-0
361:). Similar manipulations apply to other organoarsenic chloride compounds.
973:
808:
706:
492:
401:
Such reactions require copper catalysts, are conducted near 360 °C.
1542:
1176:
Grund, S. C.; Hanusch, K.; Wolf, H. U. "Arsenic and
Arsenic Compounds".
869:
Some illustrative organoarsenic compound are listed in the table below:
510:. They behave like phosphine ligands, but are less basic. The diarsine C
1284:
791:
686:
678:
484:
225:
97:
89:
46:
1551:
1142:
1125:
1010:
1751:
1433:"Microbial Methylation of Metalloids: Arsenic, Antimony, and Bismuth"
1400:"Biomethylation of Arsenic in an Arsenic-rich Freshwater Environment"
1126:"Cadet's Fuming Arsenical Liquid and the Cacodyl Compounds of Bunsen"
1061:
1057:
1031:
1004:
1000:
969:
938:
674:
535:
480:
211:
Arsenic(V) compounds typically feature the functional groups RAsO(OH)
125:
66:
50:
92:(tetramethyldiarsine) was one of the first organoarsenic compounds.
812:
682:
662:
531:
84:
1277:
The
Chemistry of Organic Arsenic, Antimony, and Bismuth Compounds
1213:
Elschenbroich, C. "Organometallics" (2006) Wiley-VCH: Weinheim.
911:
842:
822:
The only polyarsenic compound isolated from a natural source is
108:
was one of the first pharmaceuticals, earning a Nobel prize for
1723:
1705:
301:
Many organoarsenic compounds are prepared by alkylation of AsCl
639:
Further oxidation then depolymerizes them to arsinous acids.
561:
Oligomers with As-As bonds include the anti-syphylic drugs
1279:. Chemistry of Functional Groups. Chichester, UK: Wiley.
1599:
John S. Edmonds; Kevin A. Francesconi; Jack R. Cannon;
1156:
871:
27:
Chemistry of organic compounds with arsenic–carbon bond
263:) are used as feed additives for livestock, including
845:
of 34.5 mg/kg (mice) whereas for the betaine (CH
631:. Oxidation first forms polymeric arsinoxides, e.g.:
267:(3-NHPAA or Roxarsone), ureidophenylarsonic acid and
709:" (chlorovinyl-2-arsenic dichloride) and "Clark I" (
2388:
754:of arsenic compounds starts with the formation of
587:Protic arsines oxidize to oligomers. For example,
1566:Francesconi, Kevin A.; Edmonds, John S. (1998).
677:, they either olefinate or cyclopropanate. With
819:, the use of which has long been discontinued.
642:Arsine(III) compounds add to multiple bonds as
616:These compounds have structures similar to the
498:Symmetrical organoarsenic(III) compounds, e.g.
1179:Ullmann's Encyclopedia of Industrial Chemistry
1735:
1431:Bentley, Ronald; Chasteen, Thomas G. (2002).
8:
546:Lower-order organoarsenic compounds and uses
1267:
1265:
1263:
1261:
1259:
1257:
1255:
1253:
1742:
1728:
1720:
1664:
1662:
1437:Microbiology and Molecular Biology Reviews
1232:Journal of Inorganic and Nuclear Chemistry
1754:with other elements in the periodic table
1550:
1456:
1415:
1171:
1169:
1141:
803:bound to arsenic, collectively known as
394:
390:
386:
382:
378:
139:The hydroxyarsenic compounds are known:
73:. Despite their toxicity, organoarsenic
1524:
1522:
1209:
1207:
1116:
1771:
1361:. Cambridge: RSC publishing: 231–265.
1316:. Cambridge: RSC publishing: 165–229.
874:Representative organoarsenic compounds
297:Organoarsenic(III) compounds and uses
7:
2413:Academic research, no widespread use
542:is an indicator for several metals.
265:4-hydroxy-3-nitrobenzenearsonic acid
1568:"Arsenic Species in Marine Samples"
277:Compounds of arsenic(V) containing
207:Organoarsenic(V) compounds and uses
1082:182–184 °C (360–363 °F)
554:, compounds with As=As, As=C, and
506:, are commonly used as ligands in
325:As), dimethylarsenic chloride ((CH
124:(III) and (V), illustrated by the
25:
750:if inorganic arsenic is present.
172:As(O)OH), common, illustrated by
2305:
2224:
2156:
2061:
1761:
1404:Applied Organometallic Chemistry
1066:
1036:
1009:
978:
943:
916:
746:produces significant amounts of
120:Arsenic typically occurs in the
665:are generally less stable than
1449:10.1128/MMBR.66.2.250-271.2002
1:
1672:Chemistry: A European Journal
1617:10.1016/S0040-4039(01)93098-9
1188:10.1002/14356007.a03_113.pub2
705:. Infamous examples include "
1581:(2): 343–359. Archived from
1244:10.1016/0022-1902(61)80492-2
681:compounds, they either form
116:Synthesis and classification
1355:Metal Ions in Life Sciences
1322:10.1039/9781849730822-00165
1310:Metal Ions in Life Sciences
2456:
1124:Seyferth, Dietmar (2001).
1105:Category:Arsenic compounds
861:the LD50 exceeds 10 g/kg.
807:, are found especially in
743:Scopulariopsis brevicaulis
635:MeAs + O → MeAsO
491:, the arsenic analogue of
483:, the arsenic analogue of
313:. For example, the series
305:and its derivatives using
190:), common, illustrated by
132:(X = F, Cl, Br, I) and AsF
2302:
2221:
1773:
1769:
1759:
1367:10.1515/9783110436600-012
625:electrochemical reduction
353:AsH) and methylarsine (CH
235:The monomethylated acid,
865:Representative compounds
832:Echinochalina bargibanti
740:. For example, the mold
671:Corey-Chaykovsky reagent
335:methylarsenic dichloride
2440:Organoarsenic compounds
1182:. Weinheim: Wiley-VCH.
370:organosilicon chemistry
143:arsonous acids (RAs(OH)
102:organometallic compound
31:Organoarsenic chemistry
2408:Many uses in chemistry
2403:Core organic chemistry
1684:10.1002/chem.200600783
1645:10.1002/anie.200705405
1484:Archives of Toxicology
508:coordination chemistry
424:H + 2 Zn + 4 HCl → (CH
93:
1575:Croatica Chemica Acta
1497:10.1007/s002040000134
811:. Arsenic containing
786:The organic compound
569:. They are typically
88:
1633:Angew. Chem. Int. Ed
1095:Arsenic biochemistry
965:Phenyldichloroarsine
796:Western rock lobster
715:Phenyldichloroarsine
711:chlorodiphenylarsine
701:, especially during
381:Br + 2 As → (CH
1605:Tetrahedron Letters
1543:10.1021/cr00094a002
876:
763:-adenosylmethionine
618:phosphorus sulfides
237:methanearsonic acid
1285:10.1002/0470023473
872:
603: + O → H
595:-methylarsine(I):
591:oxidizes first to
249:phenylarsonic acid
192:phenylarsonic acid
94:
2427:
2426:
2383:
2382:
1639:(14): 2665–2667.
1611:(18): 1543–1546.
1376:978-1-84755-177-1
1331:978-1-84755-177-1
1219:978-3-527-29390-2
1143:10.1021/om0101947
1100:Arsenic poisoning
1086:
1085:
629:zinc-sulfate cell
534:, is a chelating
311:Grignard reagents
158:arsinous acids (R
16:(Redirected from
2447:
2419:
2414:
2409:
2404:
2309:
2308:
2228:
2227:
2160:
2159:
2065:
2064:
1762:
1744:
1737:
1730:
1721:
1714:
1713:
1710:sigmaaldrich.com
1702:
1696:
1695:
1666:
1657:
1656:
1627:
1621:
1620:
1596:
1590:
1589:
1587:
1572:
1563:
1557:
1556:
1554:
1531:Chemical Reviews
1526:
1517:
1516:
1477:
1471:
1470:
1460:
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1422:
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1395:
1389:
1388:
1350:
1344:
1343:
1305:
1299:
1298:
1269:
1248:
1247:
1238:(3–4): 213–218.
1227:
1221:
1211:
1202:
1201:
1173:
1164:
1154:
1148:
1147:
1145:
1136:(8): 1488–1498.
1121:
1070:
1040:
1013:
982:
947:
920:
904:10,10'-oxybis-10
877:
783:
756:methanearsonates
717:is another one.
699:chemical weapons
693:Chemical warfare
667:phosphine ylides
611:
577:
552:double bond rule
397:
230:Bechamp reaction
228:, the so-called
155:) is well known)
122:oxidation states
77:are well known.
21:
2455:
2454:
2450:
2449:
2448:
2446:
2445:
2444:
2430:
2429:
2428:
2423:
2422:
2417:
2412:
2407:
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2384:
2306:
2225:
2157:
2062:
1755:
1748:
1718:
1717:
1704:
1703:
1699:
1678:(35): 8989–94.
1668:
1667:
1660:
1629:
1628:
1624:
1601:Colin L. Raston
1598:
1597:
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1224:
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1205:
1198:
1175:
1174:
1167:
1155:
1151:
1130:Organometallics
1123:
1122:
1118:
1113:
1091:
934:Triphenylarsine
867:
860:
856:
852:
848:
840:
826:, found in the
781:
777:
773:
769:
748:trimethylarsine
738:
723:
695:
654:(but more than
612:
609:
607:O + (MeAs)
606:
602:
585:
578:
575:
548:
529:
525:
521:
517:
513:
504:triphenylarsine
500:trimethylarsine
474:
470:
466:
462:
458:
454:
450:
446:
439:
435:
431:
427:
423:
419:
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388:
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352:
348:
344:
340:
332:
328:
324:
320:
315:trimethylarsine
304:
299:
292:
288:
284:
272:-arsanilic acid
262:
258:
254:
246:
242:
218:
214:
209:
201:
197:
189:
179:
171:
161:
154:
146:
135:
131:
118:
104:. The compound
83:
28:
23:
22:
18:Organic arsenic
15:
12:
11:
5:
2453:
2451:
2443:
2442:
2432:
2431:
2425:
2424:
2421:
2420:
2415:
2410:
2405:
2400:
2397:Chemical bonds
2393:
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2355:
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2300:
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2294:
2289:
2284:
2279:
2274:
2269:
2264:
2259:
2254:
2249:
2244:
2239:
2234:
2229:
2222:
2219:
2218:
2214:
2213:
2210:
2207:
2204:
2201:
2198:
2195:
2192:
2189:
2186:
2183:
2180:
2177:
2172:
2169:
2166:
2161:
2154:
2149:
2145:
2144:
2141:
2136:
2131:
2126:
2121:
2116:
2111:
2106:
2101:
2096:
2091:
2086:
2081:
2076:
2071:
2066:
2059:
2054:
2048:
2047:
2042:
2037:
2032:
2027:
2022:
2017:
2012:
2007:
2002:
1997:
1992:
1987:
1982:
1977:
1972:
1967:
1965:
1960:
1954:
1953:
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1933:
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1918:
1913:
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1903:
1898:
1893:
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1878:
1873:
1871:
1866:
1860:
1859:
1854:
1849:
1844:
1839:
1834:
1829:
1824:
1818:
1817:
1814:
1809:
1804:
1799:
1794:
1789:
1784:
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1777:
1774:
1772:
1770:
1768:
1760:
1757:
1756:
1749:
1747:
1746:
1739:
1732:
1724:
1716:
1715:
1697:
1658:
1622:
1591:
1588:on 2008-03-09.
1558:
1537:(4): 713–764.
1518:
1491:(6): 289–299.
1472:
1443:(2): 250–271.
1423:
1410:(4): 297–304.
1390:
1375:
1345:
1330:
1300:
1293:
1275:, ed. (1994).
1249:
1222:
1203:
1197:978-3527306732
1196:
1165:
1149:
1115:
1114:
1112:
1109:
1108:
1107:
1102:
1097:
1090:
1087:
1084:
1083:
1077:
1074:
1071:
1064:
1055:
1049:
1048:
1046:
1043:
1041:
1034:
1029:
1023:
1022:
1020:
1017:
1014:
1007:
998:
992:
991:
989:
986:
983:
976:
967:
961:
960:
959:58-61 °C
954:
951:
948:
941:
936:
930:
929:
927:
924:
921:
914:
909:
901:
900:
897:
892:
887:
884:
881:
866:
863:
858:
854:
850:
846:
838:
830:marine sponge
828:New Caledonian
779:
775:
771:
767:cacodylic acid
752:Biomethylation
736:
722:
719:
694:
691:
648:Brønsted basic
637:
636:
614:
613:
608:
604:
600:
584:
581:
574:
547:
544:
527:
523:
519:
515:
511:
477:
476:
472:
468:
464:
460:
456:
452:
448:
444:
441:
437:
433:
429:
425:
421:
417:
413:
406:cacodylic acid
399:
398:
366:Direct process
358:
354:
350:
346:
342:
338:
330:
326:
322:
318:
302:
298:
295:
290:
286:
282:
260:
256:
252:
244:
240:
216:
212:
208:
205:
204:
203:
199:
195:
187:
181:
177:
174:cacodylic acid
169:
163:
159:
156:
152:
144:
133:
129:
117:
114:
82:
79:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
2452:
2441:
2438:
2437:
2435:
2416:
2411:
2406:
2401:
2398:
2395:
2394:
2391:
2387:
2379:
2376:
2374:
2371:
2369:
2366:
2364:
2361:
2359:
2356:
2354:
2351:
2349:
2346:
2344:
2341:
2339:
2336:
2334:
2331:
2329:
2326:
2324:
2321:
2319:
2316:
2314:
2311:
2304:
2301:
2298:
2295:
2293:
2290:
2288:
2285:
2283:
2280:
2278:
2275:
2273:
2270:
2268:
2265:
2263:
2260:
2258:
2255:
2253:
2250:
2248:
2245:
2243:
2240:
2238:
2235:
2233:
2230:
2223:
2220:
2216:
2215:
2211:
2208:
2205:
2202:
2199:
2196:
2193:
2190:
2187:
2184:
2181:
2178:
2176:
2173:
2170:
2167:
2165:
2162:
2155:
2153:
2150:
2147:
2146:
2142:
2140:
2137:
2135:
2132:
2130:
2127:
2125:
2122:
2120:
2117:
2115:
2112:
2110:
2107:
2105:
2102:
2100:
2097:
2095:
2092:
2090:
2087:
2085:
2082:
2080:
2077:
2075:
2072:
2070:
2067:
2060:
2058:
2055:
2053:
2050:
2049:
2046:
2043:
2041:
2038:
2036:
2033:
2031:
2028:
2026:
2023:
2021:
2018:
2016:
2013:
2011:
2008:
2006:
2003:
2001:
1998:
1996:
1993:
1991:
1988:
1986:
1983:
1981:
1978:
1976:
1973:
1971:
1968:
1966:
1964:
1961:
1959:
1956:
1955:
1952:
1949:
1947:
1944:
1942:
1939:
1937:
1934:
1932:
1929:
1927:
1924:
1922:
1919:
1917:
1914:
1912:
1909:
1907:
1904:
1902:
1899:
1897:
1894:
1892:
1889:
1887:
1884:
1882:
1879:
1877:
1874:
1872:
1870:
1867:
1865:
1862:
1861:
1858:
1855:
1853:
1850:
1848:
1845:
1843:
1840:
1838:
1835:
1833:
1830:
1828:
1825:
1823:
1820:
1819:
1815:
1813:
1810:
1808:
1805:
1803:
1800:
1798:
1795:
1793:
1790:
1788:
1785:
1783:
1780:
1779:
1775:
1767:
1764:
1763:
1758:
1753:
1750:Compounds of
1745:
1740:
1738:
1733:
1731:
1726:
1725:
1722:
1711:
1707:
1701:
1698:
1693:
1689:
1685:
1681:
1677:
1673:
1665:
1663:
1659:
1654:
1650:
1646:
1642:
1638:
1634:
1626:
1623:
1618:
1614:
1610:
1606:
1602:
1595:
1592:
1584:
1580:
1576:
1569:
1562:
1559:
1553:
1548:
1544:
1540:
1536:
1532:
1525:
1523:
1519:
1514:
1510:
1506:
1502:
1498:
1494:
1490:
1486:
1485:
1476:
1473:
1468:
1464:
1459:
1454:
1450:
1446:
1442:
1438:
1434:
1427:
1424:
1418:
1413:
1409:
1405:
1401:
1394:
1391:
1386:
1382:
1378:
1372:
1368:
1364:
1360:
1356:
1349:
1346:
1341:
1337:
1333:
1327:
1323:
1319:
1315:
1311:
1304:
1301:
1296:
1290:
1286:
1282:
1278:
1274:
1268:
1266:
1264:
1262:
1260:
1258:
1256:
1254:
1250:
1245:
1241:
1237:
1233:
1226:
1223:
1220:
1216:
1210:
1208:
1204:
1199:
1193:
1189:
1185:
1181:
1180:
1172:
1170:
1166:
1163:
1159:
1153:
1150:
1144:
1139:
1135:
1131:
1127:
1120:
1117:
1110:
1106:
1103:
1101:
1098:
1096:
1093:
1092:
1088:
1081:
1078:
1075:
1072:
1069:
1065:
1063:
1059:
1056:
1054:
1051:
1050:
1047:
1044:
1042:
1039:
1035:
1033:
1030:
1028:
1027:Arsenobetaine
1025:
1024:
1021:
1018:
1015:
1012:
1008:
1006:
1002:
999:
997:
994:
993:
990:
987:
984:
981:
977:
975:
971:
968:
966:
963:
962:
958:
955:
952:
949:
946:
942:
940:
937:
935:
932:
931:
928:
925:
922:
919:
915:
913:
910:
908:-Phenoxarsine
907:
903:
902:
898:
896:
893:
891:
888:
885:
882:
879:
878:
875:
870:
864:
862:
844:
835:
833:
829:
825:
820:
818:
814:
810:
806:
802:
798:
797:
793:
789:
788:arsenobetaine
784:
768:
764:
762:
757:
753:
749:
745:
744:
739:
732:
728:
720:
718:
716:
712:
708:
704:
700:
692:
690:
688:
684:
680:
676:
672:
668:
664:
659:
657:
653:
649:
645:
640:
634:
633:
632:
630:
626:
621:
619:
598:
597:
596:
594:
590:
582:
580:
572:
571:tricoordinate
568:
564:
559:
557:
553:
545:
543:
541:
537:
533:
509:
505:
501:
496:
494:
490:
486:
482:
442:
411:
410:
409:
407:
402:
375:
374:
373:
371:
367:
362:
336:
316:
312:
308:
307:organolithium
296:
294:
280:
275:
273:
271:
266:
250:
238:
233:
231:
227:
223:
206:
193:
185:
184:arsonic acids
182:
175:
167:
166:arsinic acids
164:
157:
150:
149:arsenous acid
142:
141:
140:
137:
127:
123:
115:
113:
111:
107:
103:
99:
91:
87:
80:
78:
76:
72:
68:
64:
60:
56:
52:
48:
44:
43:chemical bond
41:containing a
40:
36:
32:
19:
2418:Bond unknown
1935:
1709:
1700:
1675:
1671:
1636:
1632:
1625:
1608:
1604:
1594:
1583:the original
1578:
1574:
1561:
1534:
1530:
1488:
1482:
1475:
1440:
1436:
1426:
1407:
1403:
1393:
1358:
1354:
1348:
1313:
1309:
1303:
1276:
1235:
1231:
1225:
1177:
1152:
1133:
1129:
1119:
905:
883:Substituents
873:
868:
836:
831:
821:
805:arsenosugars
799:
785:
760:
741:
724:
696:
660:
644:nucleophiles
641:
638:
622:
615:
592:
589:methylarsine
586:
567:Neosalvarsan
560:
549:
497:
478:
432:AsH + 2 ZnCl
403:
400:
364:Akin to the
363:
300:
278:
276:
269:
234:
222:arsenic acid
210:
138:
119:
110:Paul Ehrlich
95:
75:biomolecules
71:arsenic acid
55:insecticides
30:
29:
1273:Patai, Saul
1076:925705-41-5
1053:Arsenicin A
899:Properties
824:arsenicin A
801:Saccharides
731:methylation
703:World War I
530:, known as
489:arsabenzene
389:AsBr + CH
333:AsCl), and
186:(RAs(O)(OH)
162:AsOH), rare
1552:10214/2162
1294:047193044X
1162:817099831X
1111:References
1045:64436-13-1
895:CAS number
890:Molar mass
727:food chain
652:phosphines
459:+ HI → (CH
63:fungicides
59:herbicides
2399:to carbon
996:Roxarsone
886:Structure
841:) has an
817:Salvarsan
735:vitamin B
721:In nature
583:Reactions
563:Salvarsan
147:), rare (
106:Salvarsan
39:compounds
35:chemistry
2434:Category
1692:17039560
1653:18306198
1505:11005674
1467:12040126
1385:20877809
1340:20877808
1089:See also
1019:121-19-7
988:696-28-6
974:chlorine
953:603-32-7
923:502.2318
809:seaweeds
707:Lewisite
687:nitrones
673:). With
656:stibines
550:Per the
493:pyridine
467:AsI + SO
226:anilines
45:between
2217:
1513:1025140
926:58-36-6
792:betaine
679:nitroso
661:Arsine
485:pyrrole
259:AsO(OH)
243:AsO(OH)
176:(R = CH
151:(As(OH)
126:halides
98:cacodyl
90:Cacodyl
81:History
47:arsenic
33:is the
2389:Legend
1752:carbon
1706:"Home"
1690:
1651:
1511:
1503:
1465:
1458:120786
1455:
1383:
1373:
1338:
1328:
1291:
1217:
1194:
1160:
1073:389.76
1062:oxygen
1058:Methyl
1032:Methyl
1016:263.04
1005:oxygen
1001:Phenyl
985:222.93
970:Phenyl
950:306.23
939:Phenyl
813:lipids
683:imines
675:enones
663:ylides
540:Thorin
536:ligand
518:(As(CH
487:, and
481:arsole
455:H + SO
194:(R = C
67:arsane
61:, and
51:carbon
1586:(PDF)
1571:(PDF)
1509:S2CID
1080:Melts
957:Melts
650:than
627:in a
599:MeAsH
593:cyclo
532:diars
436:+ 2 H
224:with
1688:PMID
1649:PMID
1501:PMID
1463:PMID
1381:PMID
1371:ISBN
1336:PMID
1326:ISBN
1289:ISBN
1215:ISBN
1192:ISBN
1158:ISBN
912:Aryl
880:Name
853:AsCH
843:LD50
790:, a
770:((CH
565:and
556:As≡C
502:and
393:AsBr
377:3 CH
341:AsCl
317:((CH
309:and
279:only
215:or R
69:and
49:and
2363:CEs
2358:CCf
2353:CBk
2348:CCm
2343:CAm
2338:CPu
2333:CNp
2323:CPa
2318:CTh
2297:CYb
2292:CTm
2287:CEr
2282:CHo
2277:CDy
2272:CTb
2267:CGd
2262:CEu
2257:CSm
2252:CPm
2247:CNd
2242:CPr
2237:CCe
2232:CLa
2212:Og
2209:Ts
2206:Lv
2203:Mc
2200:Fl
2197:Nh
2194:Cn
2191:Rg
2188:Ds
2185:Mt
2182:Hs
2179:Bh
2175:CSg
2171:Db
2168:Rf
2152:CRa
2148:Fr
2143:Rn
2139:CAt
2134:CPo
2129:CBi
2124:CPb
2119:CTl
2114:CHg
2109:CAu
2104:CPt
2099:CIr
2094:COs
2089:CRe
2079:CTa
2074:CHf
2069:CLu
2057:CBa
2052:CCs
2045:CXe
2035:CTe
2030:CSb
2025:CSn
2020:CIn
2015:CCd
2010:CAg
2005:CPd
2000:CRh
1995:CRu
1990:CTc
1985:CMo
1980:CNb
1975:CZr
1963:CSr
1958:CRb
1951:CKr
1946:CBr
1941:CSe
1936:CAs
1931:CGe
1926:CGa
1921:CZn
1916:CCu
1911:CNi
1906:CCo
1901:CFe
1896:CMn
1891:CCr
1881:CTi
1876:CSc
1869:CCa
1857:CAr
1852:CCl
1837:CSi
1832:CAl
1827:CMg
1822:CNa
1816:Ne
1787:CBe
1782:CLi
1776:He
1680:doi
1641:doi
1613:doi
1547:hdl
1539:doi
1493:doi
1453:PMC
1445:doi
1412:doi
1363:doi
1318:doi
1281:doi
1240:doi
1184:doi
1138:doi
782:H),
778:AsO
713:).
685:or
658:).
471:+ H
451:AsO
443:(CH
420:AsO
412:(CH
368:in
357:AsH
337:(CH
239:(CH
128:AsX
37:of
2436::
2378:No
2373:Md
2368:Fm
2328:CU
2313:Ac
2164:Lr
2084:CW
2040:CI
1970:CY
1886:CV
1864:CK
1847:CS
1842:CP
1812:CF
1807:CO
1802:CN
1797:CC
1792:CB
1766:CH
1708:.
1686:.
1676:12
1674:.
1661:^
1647:.
1637:47
1635:.
1609:18
1607:.
1579:71
1577:.
1573:.
1545:.
1535:89
1533:.
1521:^
1507:.
1499:.
1489:74
1487:.
1461:.
1451:.
1441:66
1439:.
1435:.
1408:11
1406:.
1402:.
1379:.
1369:.
1357:.
1334:.
1324:.
1312:.
1287:.
1252:^
1236:16
1234:.
1206:^
1190:.
1168:^
1134:20
1132:.
1128:.
1060:,
1003:,
972:,
857:CO
834:.
737:12
689:.
620:.
538:.
495:.
408::
293:.
251:(C
232:.
168:(R
57:,
1743:e
1736:t
1729:v
1712:.
1694:.
1682::
1655:.
1643::
1619:.
1615::
1555:.
1549::
1541::
1515:.
1495::
1469:.
1447::
1420:.
1414::
1387:.
1365::
1359:7
1342:.
1320::
1314:7
1297:.
1283::
1246:.
1242::
1200:.
1186::
1146:.
1140::
906:H
859:2
855:2
851:3
849:)
847:3
839:3
780:2
776:2
774:)
772:3
761:S
610:n
605:2
601:2
576:n
528:2
526:)
524:2
522:)
520:3
516:4
514:H
512:6
475:O
473:2
469:3
465:2
463:)
461:3
457:2
453:2
449:2
447:)
445:3
440:O
438:2
434:2
430:2
428:)
426:3
422:2
418:2
416:)
414:3
395:2
391:3
387:2
385:)
383:3
379:3
359:2
355:3
351:2
349:)
347:3
343:2
339:3
331:2
329:)
327:3
323:3
321:)
319:3
303:3
291:5
289:)
287:5
285:H
283:6
270:p
261:2
257:5
255:H
253:6
245:2
241:3
217:2
213:2
202:)
200:5
198:H
196:6
188:2
180:)
178:3
170:2
160:2
153:3
145:2
134:5
130:3
20:)
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