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337021

Sigma-Aldrich

2-Bromo-3-methylthiophene

95%

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About This Item

Empirical Formula (Hill Notation):
C5H5BrS
CAS Number:
14282-76-9
Molecular Weight:
177.06
EC Number:
238-175-2
MDL number:
MFCD00059741
UNSPSC Code:
12352100
PubChem Substance ID:
24860449
NACRES:
NA.22

assay

95%

refractive index

n20/D 1.572 (lit.)

bp

173-176 °C (lit.)

density

1.572 g/mL at 25 °C (lit.)

functional group

bromo

storage temp.

2-8°C

SMILES string

Cc1ccsc1Br

InChI

1S/C5H5BrS/c1-4-2-3-7-5(4)6/h2-3H,1H3

InChI key

YYJBWYBULYUKMR-UHFFFAOYSA-N

General description

2-Bromo-3-methylthiophene is formed (approx. 90%) by bromination of 3-methyl thiophene with N-bromosuccinimide in the absence of benzoyl peroxide.[1]

Application

2-Bromo-3-methylthiophene was used in the preparation of poly(3,3′′′-dimethyl-(2,2′:5′,2′:5′,2′′′)tetrathiophene)).[2] It was also used in the preparation of 2-bromo-3-(bromomethyl)thiophene, lachrymatory compound.[3]

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

hcodes

H302,H318

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

154.4 °F - closed cup

flash_point_c

68 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
SHBJ9774
SHBF1013V
SHBC6601V
SHBB2235V
61796LK

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Regioregular poly (thiophene-3-alkanoic acid) s: water soluble conducting polymers suitable for chromatic chemosensing in solution and solid state.
Ewbank PC, et al.
Tetrahedron, 60(49), 11269-11275 (2004)
The Effect of Benzoyl Peroxide on the Bromination of Methylthiophenes by N-Bromosuccinimide
Dittmer K, et al.
Journal of the American Chemical Society, 71(4), 1201-1204 (1949)
Structural studies of poly (dimethyl-tetrathiophene, an intermediate between poly (thiophene) and poly (3-methylthiophene).
Fell HJ, et al.
Synthetic Metals, 55(1), 420-425 (1993)

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