2-Bromothiophene

HCID 13851CAS 1003-09-4

Basic information

Standard SMILES
Brc1cccs1
InChIKey
TUCRZHGAIRVWTI-UHFFFAOYSA-N
Molecular formula
C4H3BrS
Average molar mass
163.04 g/mol
Monoisotopic mass
161.9138832

Names & identifiers

Preferred name
2-Bromothiophene
IUPAC
2-bromothiophene
English name
2-Bromothiophene
Molecular formula
C4H3BrS
Molecular weight
163.04

Names & synonyms

2-BROMOTHIOPHENE1003-09-4Thiophene, 2-bromo-2-Thienyl bromideGFF929NUW7NSC 4456NSC-4456EINECS 213-699-4DTXSID40613892Thienyl bromideThiophene, 2bromoRefChem:467332
Show more names
2-BromthiophenS0502DKIIRINDIP-020forTipepidineThienyl bromide2-bromo-thiophen2-Bromothiaphene
DTXCID7032509213-699-4InChI=1/C4H3BrS/c5-4-2-1-3-6-4/h1-3Thiophene, bromo-Bromothiophene2-bromo-thiophene2-bromo thiopheneMFCD00005417

Database identifiers

CAS
1003-09-4、60326-18-3
PubChem CID
13851
DTXSID
DTXSID4061389
UNII
GFF929NUW7
EC Number
213-699-4
Nikkaji
J101.470F

Properties

Computed structural properties

XLogP
2.8
Topological polar surface area
28.2 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
0
Heavy atoms
6

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Thiophenes
SpringerMaterials PropertiesSchoenflies notation
LogP2.75
Physical DescriptionClear slightly brown liquid with a stench; [Acros Organics MSDS]

Physicochemical properties

Melting point
-10 °C · -10 °C
Boiling point
149 · 149-151 °C (lit.)
Density
1.684 g/mL · 1.684 g/mL at 25 °C (lit.)
refractive index
20 · n20/D 1.586(lit.)
Flash point
140 °F · 140 °F
storage temp.
2 · 2-8°C

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P260, P262, P264, P264+P265, P270, P271, P280, P284, P301+P316, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P320, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 78 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Status: Active Update: 03-05-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/20637

2-Bromothiophene: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryAn irritant; Highly toxic by skin absorption; Harmful by ingestion and inhalation; Oral LD50 (rat) = 200-250 mg/kg; [Acros Organics MSDS] See 3,4-Dibromothiophene.
Hazard Classes and CategoriesFlam. Liq. 3 (100%)

Toxicology

Toxicity DataLC50 (rat) = 1,040 mg/m3/4hr

Safety data

F
8
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
3
tsca
TSCA listed
ridadr
UN 2929 6.1/PG 2
hs_code
29349990

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationThiophene, 2-bromo-: ACTIVE
Applications · 2 items

Uses2-Bromothiophene has been used in electrochemical reduction of a number of mono- and dihalothiophenes at carbon cathodes in dimethylformamide containing tetramethylammonium per chlorate by cyclic voltammetry and controlled-potential electrolysis.

General Description2-Bromothiophene undergoes metalation-alkylation reaction with various electrophiles to form various 5-alkylated 2-bromo products. It undergoes coupling with 4-bromo allyl phenyl ether to form allyl phenyl thiophene ether, which is a novel potential dielectric material for organic thin film transistors.

Preparation methods · 1 item

Preparation2-Bromothiophene is synthesized by bromination of thiophene, which is achieved through the following steps: dissolve thiophene in acetic acid, and add bromine in glacial acetic acid solution below 10°C. Water was added to the reaction mixture to precipitate an oily liquid. Extract with ether. Add potassium carbonate to the extract to remove acetic acid, dry it, distill off the ether, and then conduct vacuum distillation to collect fractions at 42-46°C (1.73kPa) to obtain 2-bromothiophene with a yield of 55%.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
T&W GROUP021-61551611 13296011611 · [email protected]

Related reactions

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