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
Show more names
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
- Formal charge
- 0
- Complexity
- 46.8
Experimental & physicochemical properties
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
- form
- Liquid
- Specific Gravity
- 1.684 · 1.684
- color
- Clear colorless to slightly brownish
- Water Solubility
- IMMISCIBLE
- Sensitive
- Light Sensitive
- BRN
- 104663 · 104663
- InChI
- 1S/C4H3BrS/c5-4-2-1-3-6-4/h1-3H
- InChIKey
- TUCRZHGAIRVWTI-UHFFFAOYSA-N
- SMILES
- Brc1cccs1
- CAS DataBase Reference
- 1003 · 1003-09-4(CAS DataBase Reference)
- FDA UNII
- 929 NUW7 · GFF929NUW7
- NIST Chemistry Reference
- 2 · Thiophene, 2-bromo-(1003-09-4)
- EPA Substance Registry System
- 2 · Thiophene, 2-bromo- (1003-09-4)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02,GHS05,GHS06
- Signal word
- Danger
- Hazard statements
- 226 · H226-H300-H318
- Precautionary statements
- 210 · P210-P233-P240-P280-P301+P310-P305+P351+P338
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- T,N,Xn
- Risk Statements
- 10 · 10-25-41-51/53-36/37/38-23/24-22-20/21/22
- Safety Statements
- 26 · 26-36/37/39-45-61-16-36
- RIDADR
- 2929 · UN 2929 6.1/PG 2
- WGK Germany
- 3 · 3
- F
- 8 · 8
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1
- PackingGroup
- II
- HS Code
- 29349990 · 29349990
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 2 OralEye · Acute Tox. 2 OralEye Dam. 1Flam. Liq. 3
- REACH Registrations
- Active
- Limited Quantities
- 100 ml · 100ml (liquid) or 0.5 Kg (solid)
- Excepted Quantities
- Max Inner Pack (1g or 1ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
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
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
Toxicology
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
- risk_code
- 10-25-41-51/53-36/37/38-23/24-22-20/21/22
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS05,GHS06
- hazard_code
- T,N,Xn
- hazard_note
- Irritant
- safety_code
- 26-36/37/39-45-61-16-36
- hazard_class
- 6.1
- Storage Class
- 3 - Flammable liquids
- packing_group
- II
- Hazard statements
- H226-H300-H318
- Limited Quantities
- 100ml (liquid) or 0.5 Kg (solid)
- Excepted Quantities
- Max Inner Pack (1g or 1ml) and Max Outer Pack (500g or 500ml)
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 2 OralEye Dam. 1Flam. Liq. 3
- Precautionary statements
- P210-P233-P240-P280-P301+P310-P305+P351+P338
Chemistry & industry
Uses & manufacturing
Applications
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
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%.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Related reactions
Linked notes
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