4-Bromothiophenol

4-Bromothiophenol
Names
	Other names p-bromothiophenol; 1-bromo-4-mercaptobenzene
Identifiers
CAS Number	106-53-6 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL278240;
ChemSpider	59439;
ECHA InfoCard	100.003.099
EC Number	203-407-3;
PubChem CID	66049;
UNII	P3WUO03X17;
CompTox Dashboard (EPA)	DTXSID8059340;
	InChI InChI=1S/C6H5BrS/c7-5-1-3-6(8)4-2-5/h1-4,8H Key: FTBCOQFMQSTCQQ-UHFFFAOYSA-N;
	SMILES C1=CC(=CC=C1S)Br;
Properties
Chemical formula	C6H5BrS
Molar mass	189.07 g·mol−1
Appearance	Colorless crystals
Melting point	72-74 °C
Boiling point	230.5 °C
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H314, H315, H319, H335
Precautionary statements	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). Infobox references

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

Synthesis

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

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

^ Field, Lamar (2002). "Aromatic Sulfonic Acid Anhydrides". Journal of the American Chemical Society. 74 (2): 394–398. doi:10.1021/ja01122a032. ISSN 0002-7863.
^ "PhysProp" data were obtained from Syracuse Research Corporation of Syracuse, New York (US)
^ 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.
^ 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.
^ 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.
^ 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.

[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.

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