3-bromothiophene

• ChemBase ID: 8513
• Molecular Formular: C4H3BrS
• Molecular Mass: 163.03562
• Monoisotopic Mass: 161.9138831
• SMILES: c1(ccsc1)Br
• Canonical SMILES: Brc1cscc1
• InChI: InChI=1S/C4H3BrS/c5-4-1-2-6-3-4/h1-3H
• InChIKey: XCMISAPCWHTVNG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-bromothiophene
• IUPAC Traditional name: 3-bromothiophene
• Synonyms: 3-Bromothiophene 97%; 3-Thienyl bromide; 3-Bromothiophene; 3-BROMO THIOPHENE; 3-Bromothiophene; 3-噻吩基溴; 3-溴噻吩

Database IDs

• CAS Number: 872-31-1
• EC Number: 212-821-3
• MDL Number: MFCD00005464
• Beilstein Number: 105338
• PubChem SID: 160971820; 24846726; 24851112
• PubChem CID: 13383

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.5224404
• LogD (pH = 7.4): 2.5224404
• Log P: 2.5224404
• Molar Refractivity: 30.7866 cm^3
• Polarizability: 11.938102 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 138 - 140°C
• Boiling Point: 150 °C(lit.); 150°C; 157-158°C; 159°C; 92-93°C/90mm
• Flash Point: 125.6 °F; 52 °C; 63°C; 63°C(145°F)
• Density: 1.721 g/ml; 1.722; 1.74 g/mL at 25 °C(lit.); 1.740
• Refractive Index: 1.5910; n20/D 1.591(lit.); n20/D 1.592
• Hydrophobicity(logP): 2.693

Safety Information

• Storage Warning: TOXIC, FLAMMABLE; Toxic/Flammable/Irritant/Light Sensitive/Stench/Keep Cold
• European Hazard Symbols: Flammable (F); Nature polluting (N); Toxic (T)
• UN Number: 1993; UN2810
• German water hazard class: 3
• Hazard Class: 3; 6.1
• Packing Group: 3; II
• Risk Statements: 10-23/24/25-36/37-43-51/53; 23/24/25-36/37/38-51/53; R:10
• Safety Statements: 26-27-36/37-45-61; 26-36/37-45-61; S:9-16-29
• TSCA Listed: true; 是
• GHS Pictograms: GHS02; GHS06; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H226-H301-H310-H317-H319-H330-H335; H300-H310-H330-H315-H319-H335-H227-H401-H411
• GHS Precautionary statements: P210-P301+P310-P304+P340-P305+P351+P338-P320-P330-P361-P405-P501A; P260-P280-P284-P301 + P310-P302 + P350-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1993 3/PG 3

Product Information

• Purity: ≥95% (GC); 95%; 97%; 98%
• Grade: technical
• Empirical Formula (Hill Notation): C4H3BrS

DETAILS

MP Biomedicals - 05223871

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 106224

Application
Forms 3,3-Bithiophene via borylation followed by Suzuki coupling.1 Novel coupling at the thiophene 2-position with N-arylmethanesulfonamides mediated by iodobenzene diacetate (178721).2
Packaging
5, 25, 100 g in glass bottle

REFERENCES

• Intermediate for preparation of 3-substituted thiophenes by the Grignard route: Arkiv. Kemi., 13, 295 (1959). Similarly, used in the synthesis of poly(3-alkylthiophenes) as conducting polymers: J. Org. Chem., 58, 904 (1993). Conditions have been described for the formation of 3-lithiothiophene, previously considered to be stable only under cryogenic conditions. It has been found to be stable in hexane solution at ambient temperature: Tetrahedron Lett., 35, 3673 (1994). Subsequent reaction with electrophiles leads to a variety of 3-substituted thiophenes.