(2,3-dihydro-1,4-benzodioxin-6-yl)boronic acid

• ChemBase ID: 10543
• Molecular Formular: C8H9BO4
• Molecular Mass: 179.96566
• Monoisotopic Mass: 180.05938917
• SMILES: c1cc(cc2c1OCCO2)B(O)O
• Canonical SMILES: OB(c1ccc2c(c1)OCCO2)O
• InChI: InChI=1S/C8H9BO4/c10-9(11)6-1-2-7-8(5-6)13-4-3-12-7/h1-2,5,10-11H,3-4H2
• InChIKey: SQDUGGGBJXULJR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2,3-dihydro-1,4-benzodioxin-6-yl)boronic acid
• IUPAC Traditional name: 2,3-dihydro-1,4-benzodioxin-6-ylboronic acid
• Synonyms: 1,4-Benzodioxane-6-boronic acid; 3,4-Ethylenedioxybenzeneboronic acid; 2,3-Dihydro-1,4-benzodioxine-6-boronic acid; 2,3-Dihydro-1,4-benzodioxin-6-ylboronic acid; 3,4-(Ethylenedioxy)benzeneboronic acid; 1,4-Benzodioxane-6-boronic acid; 1,4-Benzodioxan-6-boronic acid; 6-(1,4-Benzodioxanyl)boronic acid; 1,4-Benzodioxane-6-boronic acid; 1,4-苯二氧烷-6-硼酸; 1,4-苯并二噁烷-6-硼酸; 6-(1,4-苯并二噁烷)硼酸; 苯并-1,4-二氧六环-6-硼酸

Database IDs

• CAS Number: 164014-95-3
• MDL Number: MFCD01009696
• Beilstein Number: 7478648
• PubChem SID: 24882748; 160973850
• PubChem CID: 2776178

CALCULATED PROPERTIES

• Acid pKa: 8.779501
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.9563731
• LogD (pH = 7.4): 0.93893784
• Log P: 0.9566
• Molar Refractivity: 41.5609 cm^3
• Polarizability: 17.870665 Å^3
• Polar Surface Area: 58.92 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Warning: IRRITANT; Irritant/Keep Cold/Store under Argon
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36/37; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: 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

Product Information

• Purity: 97%; 98%
• Empirical Formula (Hill Notation): C8H9BO4

DETAILS

Sigma Aldrich - 635995

Other Notes
Contains varying amounts of anhydride
Packaging
1, 5 g in glass bottle
Application
Reactant involved in:
• Addition reactions with 1,8-naphthyridine N-oxides1
• Iodocyclization and palladium-catalyzed coupling reactions for synthesis of pyranoquinolines2
• Suzuki coupling reactions for synthesis of combretastatin analogs3
• Suzuki-Miyaura coupling reactions for synthesis of aryl-substituted oxabenzindoles and methanobenzindoles4
• Palladium-catalyzed oxyarylation of Heck reaction intermediates5
• C-H functionalization of quinones6