3-Bromothiophene

3-Bromothiophene
Names
	Preferred IUPAC name 3-Bromothiophene
	Other names 3-Thienyl bromide, 3BT
Identifiers
CAS Number	872-31-1;
3D model (JSmol)	Interactive image;
ChemSpider	12811;
ECHA InfoCard	100.011.656
EC Number	212-821-3;
PubChem CID	13383;
UNII	G818Z74YV0;
CompTox Dashboard (EPA)	DTXSID2022129 ;
	InChI InChI=1S/C4H3BrS/c5-4-1-2-6-3-4/h1-3H Key: XCMISAPCWHTVNG-UHFFFAOYSA-N; InChI=1/C4H3BrS/c5-4-1-2-6-3-4/h1-3H Key: XCMISAPCWHTVNG-UHFFFAOYAH;
	SMILES C1=CSC=C1Br;
Properties
Chemical formula	C4H3BrS
Molar mass	163.03 g·mol−1
Appearance	Colorless liquid
Density	1.74 g/mL
Melting point	−10 °C (14 °F; 263 K)
Boiling point	150–158 °C (302–316 °F; 423–431 K)
Solubility in water	Immiscible
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	N,Xi,Xn,T
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H301, H310, H315, H317, H319, H330, H335, H411
Precautionary statements	P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P270, P271, P272, P273, P280, P284, P301+P310, P302+P350, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P320, P321, P322, P330, P332+P313, P333+P313, P337+P313, P361, P362, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501
Flash point	56 °C (133 °F; 329 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

3-Bromothiophene is an organosulfur compound with the formula C₄H₃BrS. It is a colorless liquid. It is a precursor to the antibiotic timentin and the vasodilator cetiedil.^[1]

Preparation

Unlike 2-bromothiophene, the 3-bromo isomer cannot be prepared directly from thiophene. It can be prepared by debromination of 2,3,5-tribromothiophene,^[2] which is obtained by bromination of thiophene.

References

^ Jonathan Swanston (2006). "Thiophene". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_793.pub2. ISBN 978-3527306732.
^ S. Gronowitz (1959). "3-Bromothiophene". Org. Syntheses. 44: 9. doi:10.15227/orgsyn.044.0009.

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[Ullmann-1] Jonathan Swanston (2006). "Thiophene". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_793.pub2. ISBN 978-3527306732.

[2] S. Gronowitz (1959). "3-Bromothiophene". Org. Syntheses. 44: 9. doi:10.15227/orgsyn.044.0009.

[1]

[2]

Preparation

See also

References