(thiophen-2-yl)boronic acid

• ChemBase ID: 6669
• Molecular Formular: C4H5BO2S
• Molecular Mass: 127.9573
• Monoisotopic Mass: 128.0103308
• SMILES: c1(sccc1)B(O)O
• Canonical SMILES: OB(c1cccs1)O
• InChI: InChI=1S/C4H5BO2S/c6-5(7)4-2-1-3-8-4/h1-3,6-7H
• InChIKey: ARYHTUPFQTUBBG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (thiophen-2-yl)boronic acid
• IUPAC Traditional name: thiophen-2-ylboronic acid
• Synonyms: Thiophen-2-ylboronic acid; Thiophene-2-boronic acid; 2-thienylboronic acid; 2-Thienylboric acid; Thien-5-ylboronic acid; 2-Thienylboronic acid; Thiophene-2-boronic acid; 2-Thienylboronic acid; 2-Thiopheneboronic acid; Thiophene-2-boronic acid; thiophen-2-ylboranediol; 2-Boronothiophene; 2-噻吩硼酸; 噻吩-2-硼酸; 2-噻吩硼酸; 噻酚-2-硼酸

Database IDs

• CAS Number: 6165-68-0
• EC Number: 000-000-0
• MDL Number: MFCD00151850
• Beilstein Number: 112375
• PubChem SID: 160969976; 24867305
• PubChem CID: 2733960

CALCULATED PROPERTIES

• Acid pKa: 7.984538
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 1.2322869
• LogD (pH = 7.4): 1.1336635
• Log P: 1.2337
• Molar Refractivity: 26.8692 cm^3
• Polarizability: 12.232995 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 128-131°C; 128-131°C; 138-140 °C(lit.); 138-140°C; 139 - 140°C
• Hydrophobicity(logP): 1.241

Safety Information

• Storage Warning: Harmful/Irritant/Keep Cold; IRRITANT, KEEP COLD
• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38; 36/37/38
• Safety Statements: 26-36/37; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335; H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0%; 95%; 97%; 98%
• Empirical Formula (Hill Notation): C4H5BO2S

DETAILS

Sigma Aldrich - 436836

Other Notes
Contains varying amounts of anhydride
Packaging
1, 5 g in glass bottle
Application
Reagent used for
• Palladium-catalyzed Suzuki-Miyaura cross-couplings1
• Alkylation, boration, coupling reaction, Suzuki coupling, and halogenation of fluorenyl bromide2
• Chain-growth catalyst transfer polycondensation of conjugated alternating copolymer3
• Ferric perchlorate-promoted reaction of fullerene to give fullerenyl boronic esters4
• Ligand-free Suzuki, Sonogashira, and Heck cross-coupling reactions5
• Copper-catalyzed nitration reactions6
• Geometry relaxation-induced Large Stokes shift in red-emitting borondipyrromethenes (BODIPY) and applications in fluorescent thiol probes7 Reagent used in Preparation of
• Photophysical properties of oxygen-containing polycyclic aromatic triptycenes8
• Donor unit for donor-acceptor-type polymers via N-alkylation, Suzuki coupling, and bromination9
• Aminopyridine-based inhibitors of mitotic kinase Nek2 with potential antipoliferative effects in cancer tumors10

REFERENCES

• Suzuki coupling (see Appendix 5) to a polymer-bound aryl iodide gives the 2-arylthiophene derivative in high yield: J. Org. Chem., 61, 5169 (1996).