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reactions. As for thiophene, electrophiles tend to attack at the carbon positions next to the chalcogen. Such reactions are slower than that of furan, but faster than
293:
990:
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510:
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901:
268:
995:
764:
Atoms in selenophene are numbered sequentially around the ring, starting with the selenium atom as number 1 following normal
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670:
768:
rules. Oxidized forms include selenophene 1,1-dioxide. Related ring structures include those with only one double bond (
562:
504:
211:
451:
446:
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Pelkey, E. T. (2008). Katritzky, Alan R.; Ramsden, Christopher A.; Scriven, Eric F. V.; Taylor, Richard J. K. (eds.).
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598:
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Substituted selenophenes can be made using a
Fiesselman procedure in which a β-chloro-aldehyde reacts with
162:
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27:
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and at about 300 °C yields up to 15% selenophene were obtained. Benzoselenophene (analogue of
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Mazza and
Solazzo reported the first confirmed synthesis in 1927. By treating selenium with
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The
Chemistry of Heterocycles: Structures, Reactions, Synthesis, and Applications
849:
Nomenclature of
Organic Chemistry: IUPAC Recommendations and Preferred Names 2013
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824:
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756:. A colorless liquid, it is one of the more common selenium heterocycles.
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Except where otherwise noted, data are given for materials in their
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Eicher, Theophil; Hauptmann, Siegfried; Speicher, Andreas (2013).
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The selenophene molecule is flat. Being aromatic, it undergoes
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26:
845:International Union of Pure and Applied Chemistry
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91:
8:
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15:
958:. John Wiley & Sons. pp. 69–70.
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886:Comprehensive Heterocyclic Chemistry III
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888:. Oxford: Elsevier. pp. 975–1006.
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947:
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387:110 °C (230 °F; 383 K)
377:−38 °C (−36 °F; 235 K)
156:
280:Key: MABNMNVCOAICNO-UHFFFAOYSA-N
123:
7:
190:
991:Heterocyclic compounds with 1 ring
714:compound containing a five-member
277:InChI=1S/C4H4Se/c1-2-4-5-3-1/h1-4H
14:
726:atom. It is a selenium analog of
894:10.1016/B978-008044992-0.00313-8
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445:
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50:
667:(at 25 °C , 100 kPa).
853:The Royal Society of Chemistry
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1:
923:Thiophene and Its Derivatives
22:
1012:
821:electrophilic substitution
926:. John Wiley & Sons.
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920:Hartough, H. D. (2009).
505:Precautionary statements
986:Selenium(−II) compounds
766:systematic nomenclature
800:) was also produced.
623:Related more saturated
40:
31:
996:Selenium heterocycles
861:10.1039/9781849733069
39:
30:
65:Preferred IUPAC name
349: g·mol
105:Beilstein Reference
18:
809:ethyl bromoacetate
671:Infobox references
617:Related compounds
41:
32:
16:
870:978-0-85404-182-4
679:Chemical compound
677:
676:
643:Related compounds
475:Hazard statements
357:colorless liquid
233:CompTox Dashboard
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776:) and the fully
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691:chemical formula
687:organic compound
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855:. p. 141.
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798:benzothiophene
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722:atoms and one
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29:
25:
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20:
954:
922:
885:
879:
848:
839:
818:
802:
791:
774:3-selenolene
770:2-selenolene
763:
760:Nomenclature
682:
681:
656:tellurophene
636:3-selenolene
632:2-selenolene
466:
418:
397:
76:Identifiers
17:Selenophene
807:, and then
712:unsaturated
710:. It is an
683:Selenophene
461:Signal word
354:Appearance
310:Properties
163:100.157.009
125:CHEBI:30857
69:Selenophene
980:Categories
831:References
815:Properties
788:Production
782:selenolane
780:structure
718:with four
628:selenolane
430:Pictograms
367:1.52 g/cm
342:Molar mass
221:UYZ3M5T8L7
136:ChemSpider
83:CAS Number
825:thiophene
794:acetylene
778:saturated
743:thiophene
689:with the
652:thiophene
603:P403+P235
599:P403+P233
591:P370+P378
571:P304+P340
563:P301+P310
421:labelling
847:(2014).
724:selenium
412:Hazards
301:C1=CC=C1
93:288-05-1
363:Density
347:131.047
188:PubChem
181:100994
110:103223
962:
930:
900:
867:
720:carbon
685:is an
467:Danger
294:SMILES
201:136130
145:119907
59:Names
728:furan
648:furan
407:1.58
269:InChI
116:ChEBI
960:ISBN
928:ISBN
898:ISBN
865:ISBN
772:and
741:and
716:ring
611:P501
607:P405
595:P391
587:P330
583:P321
579:P314
575:P311
559:P280
555:P273
551:P271
547:P270
543:P264
539:P261
535:P260
531:P243
527:P242
523:P241
519:P240
515:P233
511:P210
497:H410
493:H373
489:H331
485:H301
481:H225
212:UNII
890:doi
857:doi
419:GHS
238:EPA
191:CID
982::
942:^
912:^
896:.
863:.
851:.
827:.
811:.
784:.
707:Se
609:,
605:,
601:,
597:,
593:,
589:,
585:,
581:,
577:,
573:,
569:,
565:,
561:,
557:,
553:,
549:,
545:,
541:,
537:,
533:,
529:,
525:,
521:,
517:,
513:,
495:,
491:,
487:,
483:,
423::
335:Se
968:.
936:.
906:.
892::
873:.
859::
754:S
752:4
750:H
748:4
746:C
739:O
737:4
735:H
733:4
731:C
704:4
701:H
698:4
695:C
403:)
401:D
398:n
396:(
332:4
329:H
326:4
323:C
240:)
236:(
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