(2-formylthiophen-3-yl)boronic acid

• ChemBase ID: 64503
• Molecular Formular: C5H5BO3S
• Molecular Mass: 155.9674
• Monoisotopic Mass: 156.00524542
• SMILES: c1(c(scc1)C=O)B(O)O
• Canonical SMILES: O=Cc1sccc1B(O)O
• InChI: InChI=1S/C5H5BO3S/c7-3-5-4(6(8)9)1-2-10-5/h1-3,8-9H
• InChIKey: BBENFHSYKBYWJX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-formylthiophen-3-yl)boronic acid
• IUPAC Traditional name: 2-formylthiophen-3-ylboronic acid
• Synonyms: 3-Boronothiophene-2-carboxaldehyde; 3-Borono-2-formylthiophene; 2-Formylthien-3-ylboronic acid; 2-Formylthiophen-3-ylboronic acid; 2-Formyl-3-thiopheneboronic acid; 2-Formyl-3-thienylboronic acid; 2-Formylthiophene-3-boronic acid; 2-Formylthiophene-3-boronic acid; 2-甲酰基噻吩-3-硼酸; 2-醛基噻吩-3-硼酸; 2-甲酰基噻吩-3-硼酸

Database IDs

• CAS Number: 4347-31-3
• MDL Number: MFCD01075678
• Beilstein Number: 4393584
• PubChem SID: 24873308; 162030242
• PubChem CID: 2773426

CALCULATED PROPERTIES

• Acid pKa: 8.108252
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.1368368
• LogD (pH = 7.4): 1.0606012
• Log P: 1.1379
• Molar Refractivity: 34.0774 cm^3
• Polarizability: 14.1970215 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 167-193 °C(lit.); ca 200°C dec.

Safety Information

• Storage Warning: Air Sensitive; Harmful/Irritant/Air Sensitive/Store under Argon/Keep Cold; IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: false; 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 - 499900

Other Notes
Contains varying amounts of anhydride
Packaging
5 g in glass bottle
Application
Reactant for:
• Suzuki cross-coupling reactions1
• Preparation of boronic acid esters2

REFERENCES

• Suzuki coupling (see Appendix 5) with amino bromo- or iodo-pyridine derivatives is accompanied by in situ cyclization to the thieno[2,3-c]-1,7-naphthyridine ring system: J. Heterocycl. Chem., 31, 11 (1994):