2-bromothiophene

• ChemBase ID: 8512
• Molecular Formular: C4H3BrS
• Molecular Mass: 163.03562
• Monoisotopic Mass: 161.9138831
• SMILES: c1ccsc1Br
• Canonical SMILES: Brc1cccs1
• InChI: InChI=1S/C4H3BrS/c5-4-2-1-3-6-4/h1-3H
• InChIKey: TUCRZHGAIRVWTI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-bromothiophene
• IUPAC Traditional name: 2-bromothiophene
• Synonyms: 2-Thienyl bromide; 2-Bromothiophene; 2-Bromothiophene 98%; NSC 4456; 2-Bromothiophene; 2-噻吩基溴; 2-溴噻吩

Database IDs

• CAS Number: 1003-09-4
• EC Number: 213-699-4
• MDL Number: MFCD00005417
• Beilstein Number: 104663
• PubChem SID: 24847601; 160971819
• PubChem CID: 13851

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.6884363
• LogD (pH = 7.4): 2.6884363
• Log P: 2.6884363
• Molar Refractivity: 29.9465 cm^3
• Polarizability: 11.968581 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: <-10°C
• Boiling Point: 149-151 °C(lit.); 149-151°C; 149-152°C
• Flash Point: 125.6 °F; 52 °C; 52°C; 58°C(136°F)
• Density: 1.684; 1.684 g/mL at 25 °C(lit.); 1.7; 1.701
• Refractive Index: 1.586; 1.5860; n20/D 1.586(lit.)

Safety Information

• Storage Warning: Light Sensitive; TOXIC, FLAMMABLE; Very Toxic/Flammable/Stench/Light Sensitive/Keep Cold
• European Hazard Symbols: Toxic (T)
• UN Number: 2929; UN2929
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; II
• Risk Statements: 10-25-41; 23/24/25-36/38
• Safety Statements: 26-36/37/39-45; 9-26-27-36/37/39-45-60
• TSCA Listed: true; 是
• GHS Pictograms: GHS02; GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H226-H300-H318; H300-H310-H330-H315-H319-H226
• GHS Precautionary statements: P210-P301+P310-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P361-P405-P501A; P264-P280-P301 + P310-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 2929 6.1/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: 97%; 98%; 98+%
• Empirical Formula (Hill Notation): C4H3BrS

DETAILS

Sigma Aldrich - 124168

Application
2-Thienyl esters are readily prepared from the derived Grignard reagents on treatment with CuBr-LiBr couple and chloroformates.1
Packaging
10, 50, 250 g in glass bottle

REFERENCES

• The bromo-substituent can be readily displaced by methoxide in methanol in the presence of a Cu(I) catalyst: Synth. Commun., 20, 213 (1990). For coupling reaction with Thiophene-2-thiol, B22642, in the presence of Cu₂O, to give 2,2'-dithienyl sulfide, see: Org. Synth. Coll., 6, 558 (1988).
• Allylic alcohols are thienylated by means of a Heck-type, Pd-catalyzed coupling reaction; the products are ketones formed by rearrangement: Chem. Lett., 423 (1977). Coupling with iodoarenes can be induced at the 5-position by the use of a palladium(II) catalyst in the presence of silver nitrate and potassium fluoride, providing access to 5-aryl-2-bromothiophene derivatives, which may be further elaborated by reaction with the available 2-bromo-substituent: Org. Lett., 7, 5083 (2005).