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588423

Sigma-Aldrich

Phenethylboronic acid

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Synonym(s):
2-Phenylethaneboronic acid
Linear Formula:
C6H5CH2CH2B(OH)2
CAS Number:
34420-17-2
Molecular Weight:
149.98
MDL number:
MFCD01631226
UNSPSC Code:
12352103
PubChem Substance ID:
24881217
NACRES:
NA.22

mp

76-81 °C (lit.)

Quality Level

100

SMILES string

OB(O)CCc1ccccc1

InChI

1S/C8H11BO2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5,10-11H,6-7H2

InChI key

VPRUMANMDWQMNF-UHFFFAOYSA-N

Related Categories

Application

Reactant involved in:
  • Suzuki-Miyaura cross-coupling reactions
  • Reactions with α-diazocarbonyl compounds
  • C-H functionalization of quinones
  • Cross-coupling with aromatic amines
  • Arylation and alkylation of diphenylisoxazole

Reactant used in studies of the stability of boronic esters to hydrolysis

Other Notes

Contains varying amounts of anhydride

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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J B Jones et al.
The Journal of biological chemistry, 258(4), 2135-2142 (1983-02-25)
The heat of formation of the chymotrypsin-phenylethane boronic acid complex has been observed calorimetrically from pH 4 to 8 at 25 degrees C and is found to be pH-dependent, changing from near -6 kcal/mol at pH 4 to -13 kcal/mol
A Tulinsky et al.
The Journal of biological chemistry, 262(16), 7737-7743 (1987-06-05)
A 1.8-A resolution x-ray crystallographic restrained least squares refinement has been carried out on the phenylethane boronic acid (PEBA) complex of alpha-chymotrypsin dimer (alpha-CHT), and it has been compared to the 1.67-A resolution structure of the native enzyme. PEBA has
B Goz et al.
Biochemical pharmacology, 35(20), 3587-3591 (1986-10-15)
Several compounds have been tested for their ability to inhibit bovine pancreatic alpha-chymotrypsin (Ki) and their ability to inhibit cell replication (IC50). There is good agreement over three orders of magnitude between the Ki and the IC50 values of these

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