(5-bromothiophen-2-yl)boronic acid

• ChemBase ID: 10572
• Molecular Formular: C4H4BBrO2S
• Molecular Mass: 206.85336
• Monoisotopic Mass: 205.92084277
• SMILES: s1c(ccc1Br)B(O)O
• Canonical SMILES: OB(c1ccc(s1)Br)O
• InChI: InChI=1S/C4H4BBrO2S/c6-4-2-1-3(9-4)5(7)8/h1-2,7-8H
• InChIKey: USJPOBDLWVCPGG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5-bromothiophen-2-yl)boronic acid
• IUPAC Traditional name: 5-bromothiophen-2-ylboronic acid
• Synonyms: 5-Bromothiophene-2-boronic acid; 5-Bromothiophene-2-boronic acid; 5-Bromo-2-thienylboronic acid; 5-溴噻吩-2-硼酸; 5-溴-2-噻吩硼酸

Database IDs

• CAS Number: 162607-17-2
• MDL Number: MFCD02094028
• PubChem SID: 160973879; 24879688
• PubChem CID: 2734319

CALCULATED PROPERTIES

• Acid pKa: 7.898609
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 1.9482783
• LogD (pH = 7.4): 1.8308191
• Log P: 1.95
• Molar Refractivity: 33.6519 cm^3
• Polarizability: 15.286391 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 95-100 °C(lit.)

Safety Information

• Storage Warning: IRRITANT; Irritant
• German water hazard class: 3
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: 97%; 98%
• Empirical Formula (Hill Notation): C4H4BBrO2S

DETAILS

Sigma Aldrich - 557684

Other Notes
Contains varying amounts of anhydride
Packaging
5 g in glass bottle
Application
Reactant involved in:
• Suzuki coupling reactions for the synthesis of benzotriazole-containing organic sensitizers1 and meso-Polyarylamide-BODIPY hybrids2
• Suzuki-Miyaura coupling for the synthesis of ratanhine3
• Microwave-assisted Sonogashira reactions for the synthesis of ethynylarylboronates4