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31:
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330:
453:. Alcohols are also good alkylating agents in the presence of suitable acid catalysts. For example, most methyl amines are prepared by alkylation of ammonia with methanol. The alkylation of phenols is particularly straightforward since it is subject to fewer competing reactions.
675:
in the laboratory, but it is too hazardous (explosive gas with a high acute toxicity) to be employed on an industrial scale without special precautions. Use of diazomethane has been significantly reduced by the introduction of the safer and equivalent reagent
905:. It is caused by alkylating agents such as EMS (Ethyl Methyl Sulphonate). Bifunctional alkyl groups which have two alkyl groups in them cause cross linking in DNA. Alkylation damaged ring nitrogen bases are repaired via the
573:
688:
Electrophilic, soluble alkylating agents are often toxic and carcinogenic, due to their tendency to alkylate DNA. This mechanism of toxicity is relevant to the function of anti-cancer drugs in the form of
218:
The SN2 mechanism is not available for aryl substituents, where the trajectory to attack the carbon atom would be inside the ring. Thus, only reactions catalyzed by organometallic catalysts are possible.
1192:
Ma, Qisheng; Chakraborty, Deb; Faglioni, Francesco; Muller, Rick P.; Goddard, William. A.; Harris, Thomas; Campbell, Curt; Tang, Yongchun (1 February 2006). "Alkylation of Phenol: A Mechanistic View".
444:
299:
Amines are readily alkylated. The rate of alkylation follows the order tertiary amine < secondary amine < primary amine. Typical alkylating agents are alkyl halides. Industry often relies on
881:
732:, are employed when the alkyl halide are used. Brønsted acids are used when alkylating with olefins. Typical catalysts are zeolites, i.e. solid acid catalysts, and sulfuric acid.
1493:
Michael Röper, Eugen Gehrer, Thomas
Narbeshuber, Wolfgang Siegel "Acylation and Alkylation" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2000.
701:(sulfide of dichloroethyl) function as alkylating agents. Alkylated DNA either does not coil or uncoil properly, or cannot be processed by information-decoding enzymes.
1387:
Misono, Makoto (2009). "Recent progress in the practical applications of heteropolyacid and perovskite catalysts: Catalytic technology for the sustainable society".
1510:
Kore, Rajkumar; Scurto, Aaron M.; Shiflett, Mark B. (2020). "Review of
Isobutane Alkylation Technology Using Ionic Liquid-Based Catalysts—Where Do We Stand?".
348:. The reaction is typically conducted in the presence of a base or using the conjugate base of the thiol. Thioethers undergo alkylation to give
1323:
Proctor, Lee D.; Warr, Antony J. (November 2002). "Development of a continuous process for the industrial generation of diazomethane".
147:
between the alkyl group and the electrophile. The counterion, which is a cation such as lithium, can be removed and washed away in the
1307:
649:
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March Jerry; (1985). Advanced
Organic Chemistry reactions, mechanisms and structure (3rd ed.). New York: John Wiley & Sons, inc.
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1155:
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N-, P-, and S-alkylation are important processes for the formation of carbon-nitrogen, carbon-phosphorus, and carbon-sulfur bonds,
656:
are particularly strong electrophiles due to their overt positive charge and an inert leaving group (dimethyl or diethyl ether).
690:
114:
1235:
D. Landini; F. Rolla (1978). "Sulfide
Synthesis In Preparation Of Dialkyl And Alkyl Aryl Sulfides: Neopentyl Phenyl Sulfide".
284:, as these are often easier to handle than their corresponding alkenes, which tend to be gasses. The reaction is catalysed by
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1371:
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1545:
937:
Several commodity chemicals are produced by alkylation. Included are several fundamental benzene-based feedstocks such as
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969:
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1050:
blending stock because it has exceptional antiknock properties and is clean burning. Alkylate is also a key component of
326:. Similar reactions occur when tertiary phosphines are treated with alkyl halides, the products being phosphonium salts.
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C-alkylation is a process for the formation of carbon-carbon bonds. The largest example of this takes place in the
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1058:, polymerization, and alkylation, refineries can obtain a gasoline yield of 70 percent. The widespread use of
1055:
609:, low-valent metals often react with alkylating agents to give metal alkyls. This reaction is one step in the
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261:
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713:
622:
257:
152:
1461:
Bipin V. Vora; Joseph A. Kocal; Paul T. Barger; Robert J. Schmidt; James A. Johnson (2003). "Alkylation".
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employs both a nucleophilic alkylation step subsequent to the oxidative addition of the aryl halide (L =
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288:. This approach is rarely used industrially as alkyl halides are more expensive than alkenes.
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reagents. These compounds typically can add to an electron-deficient carbon atom such as at a
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1027:, which alkylate isobutane. The product, called "alkylate", is composed of a mixture of high-
113:
to damage the DNA of cancer cells. Alkylation is accomplished with the class of drugs called
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1427:
1396:
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Shioiri, Takayuki; Aoyama, Toyohiko; Snowden, Timothy (2001). "Trimethylsilyldiazomethane".
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Sodium dodecylbenzene, obtained by alkylation of benzene with dodecene, is a precursor to
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105:, alkylation produces a premium blending stock for gasoline. In medicine, alkylation of
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1546:"Oil & Gas Engineering | Ionic liquid alkylation technology receives award"
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Bouziane, M.; Miao, F.; Ye, N.; Holmquist, G.; Chyzak, G.; O'Connor, T. R. (1998).
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Complementing alkylation reactions are the reverse, dealkylations. Prevalent are
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for effecting alkylation. Alkyl groups can also be removed in a process known as
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methods involving alkylation of amines with alcohols, the byproduct being water.
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are also commonly alkylated to produce a variety of products; examples include
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Stefanidakis, G.; Gwyn, J.E. (1993). "Alkylation". In John J. McKetta (ed.).
1023:(zeolites). The catalyst protonates the alkenes (propene, butene) to produce
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When the alkylating agent is an alkyl halide, the conversion is called the
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are used in place of the older generation of strong
Bronsted acids.
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Electrophilic alkylating agents deliver the equivalent of an alkyl
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1019:) in the presence of a Brønsted acid catalyst, which can include
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568:{\displaystyle {\ce {Ph-O- + Me2-SO4 -> Ph-O-Me + Me-SO4-}}}
180:
106:
81:. Alkylating agents are often classified according to their
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of petrochemical plants, which convert low-molecular-weight
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More complex alkylation of a alcohols and phenols involve
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Typical route for alkylation of benzene with ethylene and
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268:. This can be achieved using either acid catalysts like
876:{\displaystyle {\ce {C2H4 + CH3CO2H -> CH3CO2C2H5}}}
716:
of benzene is often catalyzed by aluminium trichloride.
27:
Transfer of an alkyl group from one molecule to another
53:
group. The alkyl group may be transferred as an alkyl
1356:
e-EROS Encyclopedia of
Reagents for Organic Synthesis
1066:
in refineries poses significant environmental risks.
757:
462:
376:
728:, sometimes both. Classically, Lewis acids, e.g.,
640:
is one of the most electrophilic alkylating agents.
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567:
438:
648:. Alkyl halides are typical alkylating agents.
439:{\displaystyle {\ce {R-OH + R'-X -> R-O-R'}}}
1512:Industrial & Engineering Chemistry Research
1463:Kirk-Othmer Encyclopedia of Chemical Technology
1563:Macrogalleria page on polycarbonate production
1352:Encyclopedia of Reagents for Organic Synthesis
1292:Encyclopedia of Reagents for Organic Synthesis
175:. Nucleophilic alkylating agents can displace
8:
1471:10.1002/0471238961.0112112508011313.a01.pub2
901:. It is the transfer of alkyl groups to the
928:and cytosine base are shown for simplicity.
1325:Organic Process Research & Development
597:is the alkylating group in this reaction.
307:is another green method for N-alkylation.
276:like aluminium. On a laboratory scale the
244:components. Electron-rich species such as
179:substituents on a carbon atom through the
1570:at the U.S. National Library of Medicine
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1007:is alkylated with low-molecular-weight
139:). The formal "alkyl anion" attacks an
660:is intermediate in electrophilicity.
93:refers to a particular alkylation of
89:character. In oil refining contexts,
7:
1262:G. S. Hiers and F. D. Hager (1941).
1194:The Journal of Physical Chemistry A
920:2-like methyl transfer reaction in
650:Trimethyloxonium tetrafluoroborate
223:Alkylation by carbon electrophiles
25:
1416:"Repair of DNA alkylation damage"
654:triethyloxonium tetrafluoroborate
638:Triethyloxonium tetrafluoroborate
991:Typical acid-catalyzed route to
691:alkylating antineoplastic agents
115:alkylating antineoplastic agents
629:Electrophilic alkylating agents
187:, they also alkylate alkyl and
1171:. CRC Press. pp. 80–138.
959:linear alkylbenzene sulfonates
817:
720:Electrophilic alkylation uses
516:
408:
340:are readily alkylated to give
151:. Examples include the use of
126:Nucleophilic alkylating agents
121:Nucleophilic alkylating agents
1:
1364:10.1002/047084289X.rt298.pub2
1300:10.1002/047084289X.rt223.pub2
970:linear alkylbenzene sulfonate
897:Alkylation in biology causes
664:Methylation with diazomethane
128:deliver the equivalent of an
1401:10.1016/j.cattod.2008.10.054
1169:Chemical Processing Handbook
601:Oxidative addition to metals
260:, or butylated phenols like
49:that entails transfer of an
1130:Category:Methylating agents
191:halides, as exemplified by
38:as a heterogeneous catalyst
1619:
1125:Category:Ethylating agents
1120:Category:Alkylating agents
980:
890:
678:trimethylsilyldiazomethane
451:Williamson ether synthesis
252:used in the production of
157:Grignard (organomagnesium)
1278:, vol. 1, p. 58
1046:). Alkylate is a premium
714:Friedel-Crafts alkylation
69:(or their equivalents).
1572:Medical Subject Headings
1524:10.1021/acs.iecr.0c03418
1499:10.1002/14356007.a01_185
1420:Acta Biochimica Polonica
1249:10.15227/orgsyn.058.0143
1056:fluid catalytic cracking
1011:(primarily a mixture of
623:cross coupling reactions
320:quaternary ammonium salt
153:organometallic compounds
1115:Friedel–Crafts reaction
736:is used to manufacture
278:Friedel–Crafts reaction
1432:10.18388/abp.1998_4333
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730:aluminium trichloride
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613:for the synthesis of
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286:aluminium trichloride
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1588:Industrial processes
907:Base Excision Repair
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374:
322:by reaction with an
318:is converted into a
292:N-,P-, S- alkylation
264:, which are used as
250:linear alkylbenzenes
1518:(36): 15811–15838.
1206:2006JPCA..110.2246M
993:2,4-dimethylpentane
977:Gasoline production
933:Commodity chemicals
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734:Silicotungstic acid
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333:Menshutkin-reaction
312:Menshutkin reaction
101:. For upgrading of
1603:Chemical processes
999:In a conventional
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183:mechanism. With a
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1568:Alkylating+agents
1548:. 2 January 2018.
1337:10.1021/op020049k
1276:Collected Volumes
1269:Organic Syntheses
1214:10.1021/jp0560213
1100:Hydrodealkylation
1064:hydrofluoric acid
1031:, branched-chain
903:nitrogenous bases
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71:Alkylating agents
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178:
174:
170:
166:
162:
161:organolithium
158:
154:
150:
146:
145:covalent bond
142:
138:
134:
131:
127:
120:
118:
116:
112:
108:
104:
100:
96:
92:
88:
87:electrophilic
84:
80:
76:
72:
68:
64:
60:
56:
52:
48:
44:
37:
32:
19:
1593:Oil refining
1540:
1515:
1511:
1505:
1489:
1462:
1456:
1423:
1419:
1409:
1392:
1388:
1382:
1355:
1351:
1345:
1328:
1324:
1318:
1291:
1285:
1275:
1267:
1257:
1240:
1236:
1230:
1197:
1193:
1187:
1168:
1162:
1146:
1110:Alkynylation
1077:
1074:Dealkylation
1036:hydrocarbons
1025:carbocations
1001:oil refinery
998:
939:ethylbenzene
936:
926:SAM cofactor
896:
719:
687:
669:Diazomethane
667:
643:
604:
591:ethoxylation
588:
448:
359:
356:O-alkylation
336:
324:alkyl halide
309:
298:
295:
266:antioxidants
231:
228:C-alkylation
217:
169:organosodium
165:organocopper
141:electrophile
125:
124:
111:chemotherapy
90:
83:nucleophilic
79:dealkylation
78:
70:
59:free radical
42:
41:
1021:solid acids
972:detergents.
924:. Only the
893:methylation
742:acetic acid
722:Lewis acids
699:mustard gas
615:acetic acid
274:Lewis acids
254:surfactants
109:is used in
55:carbocation
1582:Categories
1480:0471238961
1373:0471936235
1237:Org. Synth
1138:References
1040:isoheptane
1033:paraffinic
899:DNA damage
887:In biology
342:thioethers
91:alkylation
43:Alkylation
1532:225512999
1440:0001-527X
1264:"Anisole"
1044:isooctane
1005:isobutane
818:⟶
705:Catalysts
560:−
546:−
532:−
524:−
517:⟶
500:−
478:−
469:−
424:−
416:−
409:⟶
402:−
383:−
270:Amberlyst
137:carbanion
103:petroleum
95:isobutane
63:carbanion
1222:16466262
1094:See also
1048:gasoline
1038:(mostly
746:ethylene
697:such as
621:. Many
432:′
397:′
361:Alcohols
344:via the
242:gasoline
185:catalyst
155:such as
75:reagents
1448:9701511
1243:: 143.
1202:Bibcode
1013:propene
1009:alkenes
955:acetone
943:styrene
693:. Some
684:Hazards
310:In the
246:phenols
238:alkenes
210:, Ar =
149:work-up
99:olefins
67:carbene
65:, or a
1574:(MeSH)
1530:
1477:
1446:
1438:
1370:
1306:
1220:
1175:
1154:
1029:octane
1017:butene
951:phenol
947:cumene
646:cation
577:(with
365:ethers
338:Thiols
208:Ligand
177:halide
167:, and
1528:S2CID
1052:avgas
916:The S
617:from
581:as a
280:uses
272:, or
256:like
133:anion
130:alkyl
97:with
51:alkyl
45:is a
36:ZSM-5
1475:ISBN
1444:PMID
1436:ISSN
1368:ISBN
1304:ISBN
1218:PMID
1173:ISBN
1152:ISBN
1086:and
1062:and
1042:and
1015:and
953:and
724:and
652:and
367::
314:, a
212:Aryl
202:The
189:aryl
73:are
61:, a
57:, a
1520:doi
1495:doi
1467:doi
1428:doi
1397:doi
1393:144
1360:doi
1333:doi
1296:doi
1245:doi
1210:doi
1198:110
957:),
945:),
744:by
593:.
262:BHT
258:LAS
181:SN2
117:.
107:DNA
85:or
1584::
1526:.
1516:59
1514:.
1473:.
1465:.
1442:.
1434:.
1424:45
1422:.
1418:.
1391:.
1366:.
1358:.
1354:.
1327:.
1302:.
1294:.
1273:;
1266:.
1241:58
1239:.
1216:.
1208:.
1196:.
1090:.
1003:,
835:CO
822:CH
803:CO
790:CH
748::
680:.
579:Na
551:SO
542:Me
536:Me
520:Ph
505:SO
487:Me
465:Ph
387:OH
352:.
214:).
195:.
163:,
159:,
1534:.
1522::
1497::
1483:.
1469::
1450:.
1430::
1403:.
1399::
1376:.
1362::
1339:.
1335::
1329:6
1312:.
1298::
1280:.
1251:.
1247::
1224:.
1212::
1204::
1181:.
995:.
918:N
865:5
861:H
852:2
848:C
839:2
826:3
815:H
807:2
794:3
786:+
778:4
774:H
765:2
761:C
585:)
555:4
539:+
528:O
509:4
491:2
483:+
474:O
429:R
420:O
412:R
406:X
394:R
390:+
379:R
135:(
20:)
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