CAS 14282-76-9 2-Bromo-3-methylthiophene (HCID 84314)

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Basic information

CAS: 14282-76-9
Standard SMILES: Cc1ccsc1Br
InChIKey: YYJBWYBULYUKMR-UHFFFAOYSA-N
Molecular formula: C5H5BrS
Average molar mass: 177.06 g/mol
Monoisotopic mass: 175.92953326

Names & identifiers

Preferred name: 2-Bromo-3-methylthiophene
IUPAC: 2-bromo-3-methylthiophene
English name: 2-Bromo-3-methylthiophene
Molecular formula: C5H5BrS
Molecular weight: 177.06

Names & synonyms

2-Bromo-3-methylthiophene14282-76-9Thiophene, 2-bromo-3-methyl-EINECS 238-175-2DTXSID20162194RefChem:85683DTXCID1084685238-175-2YYJBWYBULYUKMR-UHFFFAOYSA-N2-bromo-3-methyl-thiopheneMFCD000597412-Bromo-3-methylthiophene-d3

Show more names

2B3MT178.04TH1-Br2-Bromo-3-methylthio2-bromo-3-methyltiophene3-Methyl-2-bromothiopheneThiophene,2-bromo-3-methyl-2-Bromo-3-methylthiophene>2-Bromo-3-methylthiophene 97%

2-bromo-3-methythiopheneSCHEMBL438162-Bromo-3-methylthiophene #BIDD:GT0358SCHEMBL694060SCHEMBL32865382-Bromo-3-methylthiophene, 95%SBB089226

Database identifiers

CAS: 14282-76-9
PubChem CID: 84314
DTXSID: DTXSID20162194
EC Number: 238-175-2
Nikkaji: J149.674C

Properties

Computed structural properties

XLogP: 3
Topological polar surface area: 28.2 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 1
Rotatable bonds: 0
Heavy atoms: 7
Formal charge: 0
Complexity: 65.1

Experimental & physicochemical properties

SpringerMaterials PropertiesOptical coefficient

Physicochemical properties

Melting point: 25 °C · <25 °C
Boiling point: 173 · 173-176 °C (lit.)
Density: 1.572 g/mL · 1.572 g/mL at 25 °C (lit.)
refractive index: 20 · n20/D 1.572(lit.)
Flash point: 155 °F · 155 °F
storage temp.: 2 · 2-8°C
Water Solubility: Insoluble in water
solubility: soluble in Chloroform, Ethyl Acetate
form: liquid
color: Pale yellow
Specific Gravity: 1.58 · 1.580
BRN: 105719 · 105719
InChI: InChI=1S/C5H5BrS/c1-4-2-3-7-5(4)6/h2-3H,1H3

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H302 (97.8%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P330, P332+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 46 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (97.8%)

Safety data

wgk: 3
ridadr: UN 2810
hs_code: 29349990
risk_code: 25-41-43-36/37/38-20/21/22
Signal word: Danger
Symbol(GHS): GHS05,GHS07
hazard_code: T,Xi,Xn
hazard_note: Harmful
safety_code: 26-36/37/39-45
hazard_class: 6.1
packing_group: III
Hazard statements: H302-H318
Limited Quantities: 5.0 L (1.3 gallons) (liquid) or 5.0 kg (11 lbs) (solid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Precautionary statements: P280-P305+P351+P338

Chemistry & industry

Applications

Uses2-Bromo-3-methylthiophene was used in the preparation of poly(3,3′′′-dimethyl-(2,2′:5′,2′:5′,2′′′)tetrathiophene)). It was also used in the preparation of 2-bromo-3-(bromomethyl)thiophene, lachrymatory compound.

General Description2-Bromo-3-methylthiophene is formed (approx. 90%) by bromination of 3-methyl thiophene with N-bromosuccinimide in the absence of benzoyl peroxide.

Preparation methods · 1 item

Preparation2-Bromo-3-methylthiophene synthesis: To a solution of glacial AcOH (100 mL), acetic anhydride (4.0 g, 0.039 mol), and 3-methylthiophene (9.82 g, 0.100 mol) as a stirred mixture was added NBS (19.6 g, 0.11 mol) in one portion with a slight exotherm to 44 oC. After 20 min the reaction mixture was poured onto ice, neutralized with sodium bisulfite and extracted with ether. The ether layer was washed with water and concentrated to give 11.3 g (64%) of 2-bromo-3-methylthiophene as a tan colored liquid in 88% purity by GC area % analysis: 1H NMR (CDCl3) d 7.1 (d, 1H, J=5.7 Hz), 6.7 (d, 1H, J=5.9 Hz), 2.2 (s, 3H).