2,3-dibromothiophene

• ChemBase ID: 11750
• Molecular Formular: C4H2Br2S
• Molecular Mass: 241.93168
• Monoisotopic Mass: 239.82439506
• SMILES: c1c(c(sc1)Br)Br
• Canonical SMILES: Brc1sccc1Br
• InChI: InChI=1S/C4H2Br2S/c5-3-1-2-7-4(3)6/h1-2H
• InChIKey: ATRJNSFQBYKFSM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,3-dibromothiophene
• IUPAC Traditional name: thiophene, 2,3-dibromo-
• Synonyms: 2,3-Dibromothiophene; 2,3-DIBROMOTHIOPHENE TECHNICAL GRADE; 2,3-Dibromothiophene; NSC 99003; 2,3-Dibromothiophene 98%; 2,3-二溴噻吩

Database IDs

• CAS Number: 3140-93-0
• EC Number: 221-542-6
• MDL Number: MFCD00005418
• Beilstein Number: 107512
• PubChem SID: 24893867; 24861207; 160975057
• PubChem CID: 76590

CALCULATED PROPERTIES

• Log P: 3.457189
• Molar Refractivity: 37.5693 cm^3
• Polarizability: 15.159819 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true
• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 3.457189
• LogD (pH = 7.4): 3.457189

PROPERTIES

Physical Property

• Boiling Point: 214-216°C; 215-216°C; 215-216°C; 218-219 °C(lit.)
• Flash Point: >100°C(212°F); 123.8 °F; 51 °C; 52°C
• Density: 2.135; 2.137; 2.137 g/mL at 25 °C(lit.)
• Refractive Index: 1.6300; 1.6310; n20/D 1.632; n20/D 1.632(lit.)
• Hydrophobicity(logP): 3.371

Safety Information

• Storage Warning: Flammable/Harmful/Irritant/Stench/Light Sensitive/Keep Cold; IRRITANT; Light Sensitive
• European Hazard Symbols: Toxic (T); Irritant (Xi)
• UN Number: 1993
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 3
• Risk Statements: 10-25-36; 36/38; R:36/37/38
• Safety Statements: 23-24/25-26-45; 26-37; S:20-25-26-37/39
• TSCA Listed: false; 否
• GHS Pictograms: GHS02; GHS06; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H226-H301-H319; H315-H319
• GHS Precautionary statements: P280-P305+P351+P338-P302+P352-P321-P362-P332+P313; 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 1993 3/PG 3

Product Information

• Purity: ≥97.0% (GC); 95%; 97%; 98%; 98+%
• Grade: purum; TECHNICAL
• Empirical Formula (Hill Notation): C4H2Br2S

DETAILS

MP Biomedicals - 05202122

MP Biomedicals Rare Chemical collection

Sigma Aldrich - D43905

Packaging
5 g in glass bottle

REFERENCES

• Lithiation with n-BuLi occurs selectively at the 2-position, giving e.g. on carboxylation, 3-bromothiophene-2-carboxylic acid in good yield: Synthesis, 327 (1980). With 2 eq. of n-BuLi the dilithio-derivative is obtained, providing a useful route to 2,3-disubstituted thiophenes: Synthesis, 545 (1972).
• Metallation with LDA at low temperature results, not in the expected 5-lithio-derivative, but in rearrangement to 2,4-dibromo-5-lithiothiophene, an example of the "base-catalyzed halogen dance": Synthesis, 771 (1989):