(5-formylfuran-2-yl)boronic acid

• ChemBase ID: 9898
• Molecular Formular: C5H5BO4
• Molecular Mass: 139.9018
• Monoisotopic Mass: 140.02808904
• SMILES: c1cc(oc1B(O)O)C=O
• Canonical SMILES: O=Cc1ccc(o1)B(O)O
• InChI: InChI=1S/C5H5BO4/c7-3-4-1-2-5(10-4)6(8)9/h1-3,8-9H
• InChIKey: JUWYQISLQJRRNT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5-formylfuran-2-yl)boronic acid
• IUPAC Traditional name: 5-formylfuran-2-ylboronic acid
• Synonyms: (5-formyl-2-furyl)boronic acid; 5-Formylfuran-2-boronic acid; 2-Formylfuran-5-boronic acid; 2-Formylfuran-5-boronic acid; 5-Borono-2-furaldehyde; 2-Borono-5-formylfuran; 5-Formylfuran-2-boronic acid; 5-Formyl-2-furanboronic acid; 5-Formyl-2-furanylboronic acid; 5-甲酰基呋喃-2-硼酸; 5-甲酰基-2-呋喃硼酸; 5-甲醛基呋喃-2-硼酸

Database IDs

• CAS Number: 27329-70-0
• MDL Number: MFCD01114696
• Beilstein Number: 1637050
• PubChem SID: 160973205; 24873623
• PubChem CID: 2734355

CALCULATED PROPERTIES

• Acid pKa: 7.4677153
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.20177191
• LogD (pH = 7.4): -0.06176674
• Log P: 0.2064
• Molar Refractivity: 28.8317 cm^3
• Polarizability: 12.41567 Å^3
• Polar Surface Area: 70.67 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 136 °C (dec.)(lit.); 140-144°C; ca 140°C dec.

Safety Information

• Storage Warning: Air Sensitive; Harmful/Irritant/Store at -20°C/Store under Argon; IRRITANT, KEEP COLD
• European Hazard Symbols: Corrosive (C); Irritant (Xi)
• UN Number: 3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 3
• Risk Statements: 34; 36/37/38
• Safety Statements: 26-36/37/39-45; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 3

Product Information

• Purity: 97%; 98%
• Empirical Formula (Hill Notation): C5H5BO4

DETAILS

Sigma Aldrich - 512346

Other Notes
Contains varying amounts of anhydride
Packaging
1, 5 g in glass bottle
Application
Reactant involved in Suzuki coupling for synthesis of stable dye-senstitized solar cells1,2,3Reactant involved in synthesis of biologically active molecules including:
• Heteroarylation for the synthesis of HIF-1 inhibitors4
• Disalicylic acid-furanyl derivatives to inhibit ephrin binding5
• HIV-1 integrase inhibitors6
• Epidermal growth factor receptor inhibitors7

REFERENCES

• Bifunctional reagent used in the synthesis of π -extended heteroarylfuran systems: Org. Biomol. Chem., 1, 1447 (2003).