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4-Bromothiophenol

From Wikipedia, the free encyclopedia
4-Bromothiophenol
Names
Other names
p-bromothiophenol
1-bromo-4-mercaptobenzene
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.003.099 Edit this at Wikidata
EC Number
  • 203-407-3
UNII
  • InChI=1S/C6H5BrS/c7-5-1-3-6(8)4-2-5/h1-4,8H
    Key: FTBCOQFMQSTCQQ-UHFFFAOYSA-N
  • C1=CC(=CC=C1S)Br
Properties
C6H5BrS
Molar mass 189.07 g·mol−1
Appearance Colorless crystals
Melting point 72-74 °C[1]
Boiling point 230.5 °C[2]
Hazards
GHS labelling:
GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation mark
Danger
H301, H314, H315, H319, H335
P260, P261, P264, P270, P271, P280, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

4-Bromothiophenol is an organic compound with the formula BrC6H4SH. It forms colorless crystals.

Synthesis

[edit]

4-Bromothiophenol can be synthesized via the reduction of 4-bromo-benzenesulfonyl chloride by red phosphorus and iodine in an acidic solution.[3] Hydrogenation of 4,4'-dibromodiphenyl disulfide also produces 4-bromothiophenol.[4]

Reactions

[edit]

It reacts with acetylacetone in the presence of cesium carbonate to give 3-(4-bromophenylthio)pentane-2,4-dione. 4,4'-Dibromophenyl disulfide is also produced as the intermediate.[5]

Like other thiols, it reacts with silver nitrate to produce silver 4-bromothiophenolate.[6]

References

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  1. ^ Field, Lamar (2002). "Aromatic Sulfonic Acid Anhydrides". Journal of the American Chemical Society. 74 (2): 394–398. doi:10.1021/ja01122a032. ISSN 0002-7863.
  2. ^ "PhysProp" data were obtained from Syracuse Research Corporation of Syracuse, New York (US)
  3. ^ Zhou, Shaodong; Liao, Zutai; Yuan, Jixin; Qian, Chao; Chen, Xinzhi (2012). "One-pot synthesis of 6-bromo-4,4-dimethylthiochroman". Research on Chemical Intermediates. 39 (9): 4121–4125. doi:10.1007/s11164-012-0928-8. ISSN 0922-6168. S2CID 95014526.
  4. ^ Chen, Xinzhi; Zhou, Shaodong; Qian, Chao (2012). "Catalytic transfer hydrogenation of aryl sulfo compounds". Journal of Sulfur Chemistry. 33 (2): 179–185. doi:10.1080/17415993.2012.654392. ISSN 1741-5993. S2CID 98285530.
  5. ^ Chen, Qian; Wang, Xiaofeng; Wen, Chunxiao; Huang, Yulin; Yan, Xinxing; Zeng, Jiekun (2017). "Cs2CO3-promoted cross-dehydrogenative coupling of thiophenols with active methylene compounds". RSC Advances. 7 (63): 39758–39761. doi:10.1039/C7RA06904A. ISSN 2046-2069.
  6. ^ Jardim, Guilherme A. M.; Oliveira, Willian X. C.; de Freitas, Rossimiriam P.; Menna-Barreto, Rubem F. S.; Silva, Thaissa L.; Goulart, Marilia O. F.; da Silva Júnior, Eufrânio N. (2018). "Direct sequential C–H iodination/organoyl-thiolation for the benzenoid A-ring modification of quinonoid deactivated systems: a new protocol for potent trypanocidal quinones". Organic & Biomolecular Chemistry. 16 (10): 1686–1691. doi:10.1039/C8OB00196K. ISSN 1477-0520. PMID 29450434.