(3-formylthiophen-2-yl)boronic acid

• ChemBase ID: 74773
• Molecular Formular: C5H5BO3S
• Molecular Mass: 155.9674
• Monoisotopic Mass: 156.00524542
• SMILES: O=Cc1c(B(O)O)scc1
• Canonical SMILES: O=Cc1ccsc1B(O)O
• InChI: InChI=1S/C5H5BO3S/c7-3-4-1-2-10-5(4)6(8)9/h1-3,8-9H
• InChIKey: HYXMHAHVUFTVFZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3-formylthiophen-2-yl)boronic acid
• IUPAC Traditional name: 3-formylthiophen-2-ylboronic acid
• Synonyms: (3-Formyl-2-thienyl)boronic acid; 3-Formyl-2-thiopheneboronic acid; 3-Formyl-2-thienylboronic acid; (3-Formylthiophen-2-yl)boronic acid; 3-FORMYLTHIOPHENE-2-BORONIC ACID; 2-Boronothiophene-3-carboxaldehyde; 3-Formylthiophene-2-boronic acid; 3-甲酰-2-噻吩基硼酸; 3-甲酸基噻吩-2-硼酸; 3-甲酰基噻吩-2-硼酸

Database IDs

• CAS Number: 17303-83-2
• MDL Number: MFCD01075679
• Beilstein Number: 4387740
• PubChem SID: 162039691; 24873309
• PubChem CID: 2773429

CALCULATED PROPERTIES

• Acid pKa: 7.552904
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.90539265
• LogD (pH = 7.4): 0.6782342
• Log P: 0.9092
• Molar Refractivity: 33.4532 cm^3
• Polarizability: 14.19205 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 330 °C (dec.)(lit.); ca 180°C dec.

Safety Information

• Storage Warning: Air Sensitive
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 95+%; 97%; 98%
• Empirical Formula (Hill Notation): C5H5BO3S

DETAILS

Sigma Aldrich - 499919

Other Notes
Contains varying amounts of anhydride
Packaging
1, 5 g in glass bottle
Application
Reactant for:
• Suzuki-Miyaura cross-coupling reactions1,2