[4-(bromomethyl)phenyl]boronic acid

• ChemBase ID: 10772
• Molecular Formular: C7H8BBrO2
• Molecular Mass: 214.85222
• Monoisotopic Mass: 213.9800719
• SMILES: c1c(ccc(c1)B(O)O)CBr
• Canonical SMILES: BrCc1ccc(cc1)B(O)O
• InChI: InChI=1S/C7H8BBrO2/c9-5-6-1-3-7(4-2-6)8(10)11/h1-4,10-11H,5H2
• InChIKey: PDNOURKEZJZJNZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [4-(bromomethyl)phenyl]boronic acid
• IUPAC Traditional name: 4-(bromomethyl)phenylboronic acid
• Synonyms: 4-Boronobenzyl bromide; 4-(Bromomethyl)benzeneboronic acid; 4-(Bromomethyl)phenylboronic acid; α-Bromo-p-tolueneboronic acid; p-Boronobenzyl bromide; 4-(Bromomethyl)phenylboronic acid; 4-Bromomethylphenylboronic acid; 4-(Bromomethyl)phenylboronic acid; 4-(Bromomethyl)benzeneboronic acid; 4-(溴甲基)苯硼酸

Database IDs

• CAS Number: 68162-47-0
• MDL Number: MFCD01318113
• Beilstein Number: 3030979
• PubChem SID: 24885493; 160974079
• PubChem CID: 2735593

CALCULATED PROPERTIES

• Acid pKa: 8.750213
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.3142574
• LogD (pH = 7.4): 2.2956321
• Log P: 2.3145
• Molar Refractivity: 43.4539 cm^3
• Polarizability: 18.098082 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 173-177 °C; ca 145-150°C

Safety Information

• Storage Warning: Irritant
• European Hazard Symbols: Corrosive (C); Harmful (Xn)
• UN Number: UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: III
• Risk Statements: 22-36/37/38; 34
• Safety Statements: 26-36/37; 26-36/37/39-45
• TSCA Listed: false; 否
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335; H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: 95%; 97+%; 98%; tech. 85%
• Linear Formula: BrCH2(C6H4)B(OH)2

DETAILS

Sigma Aldrich - 679437

General description
May contain varying amounts of anhydride
Packaging
1, 5 g in glass bottle
Application
Reactant involved in:
• Design of boronic acid-based autotaxin inhibitors1
• Synthesis of boronated phosphonium salts2
• Studies of incorporation of boronic acid groups to enhance gene transfection capability2
• Investigations of the effect of boronic acid-positioning in optical glucose-sensing ensemble3

REFERENCES

• Has been employed in the synthesis of para-substituted boronated stilbenes via the Wittig reaction: J. Am. Chem. Soc., 117, 8982 (1995), which were subsequently employed as highly selective fluorescent probes for glucose: J. Phys. Chem. A, 105, 6834 (2001).