(2H-1,3-benzodioxol-5-yl)boronic acid

• ChemBase ID: 8562
• Molecular Formular: C7H7BO4
• Molecular Mass: 165.93908
• Monoisotopic Mass: 166.0437391
• SMILES: c1c(ccc2c1OCO2)B(O)O
• Canonical SMILES: OB(c1ccc2c(c1)OCO2)O
• InChI: InChI=1S/C7H7BO4/c9-8(10)5-1-2-6-7(3-5)12-4-11-6/h1-3,9-10H,4H2
• InChIKey: CMHPUBKZZPSUIQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2H-1,3-benzodioxol-5-yl)boronic acid
• IUPAC Traditional name: 2H-1,3-benzodioxol-5-ylboronic acid
• Synonyms: 3,4-Methylenedioxybenzeneboronic acid; 1,3-Benzodioxole-5-boronic acid; 1,3-benzodioxol-5-ylboronic acid; 1,3-Benzodioxole-5-boronic acid; 3,4-(Methylenedioxy)phenylboronic acid; 3,4-Methylenedioxyphenylboronic acid; 3,4-(Methylenedioxy)phenylboronic acid; 3,4-(Methylenedioxy)benzeneboronic acid; 3,4-(亚甲基二氧基)苯硼酸; 3,4-亚甲二氧基苯硼酸

Database IDs

• CAS Number: 94839-07-3
• MDL Number: MFCD01009695
• Beilstein Number: 5523347
• PubChem SID: 24873316; 160971869
• PubChem CID: 2734371

CALCULATED PROPERTIES

• Acid pKa: 8.755093
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.32386
• LogD (pH = 7.4): 1.3054383
• Log P: 1.3241
• Molar Refractivity: 36.3704 cm^3
• Polarizability: 16.038465 Å^3
• Polar Surface Area: 58.92 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 224-229 °C(lit.); 224-229°C; 239-243°C; 243-245°C

Safety Information

• Storage Warning: IRRITANT; 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: 97%; 98%
• Empirical Formula (Hill Notation): C7H7BO4

DETAILS

Sigma Aldrich - 499994

Other Notes
Contains varying amounts of anhydride
Packaging
1, 5 g in glass bottle
Application
Reactant involved in:
• Petasis reaction between glyoxylic acid, α-amino phosphonates, and organylboronic acids1
• Mannich-type multicomponent assembly and 1,3-dipolar cycloaddition for synthesis of tetrahydroisoquinoline fused isoxazolidine scafford2
• Suzuki-Miyaura cross-coupling of aryl and heteroaryl halides3,4
• Oxidative Heck reaction for synthesis of functionalized cinnamaldehyde derivatives5
• Intramolecular Alder-ene and Pictet-Spengler reactions for synthesis of crinine6

REFERENCES

• Suzuki coupling (Appendix 5) with 1-amino-2-bromonaphthalene derivatives has been used in a versatile synthesis of benzo[c]phenanthridine alkaloids: J. Chem. Soc., Perkin 1, 1647 (1996).