Phenethylboronic acid

Base Information

• Chemical Name: Phenethylboronic acid
• CAS No.: 34420-17-2
• Molecular Formula: C8H11BO2
• Molecular Weight: 149.985
• Hs Code.: 2931900090
• Mol file: 34420-17-2.mol

Synonyms:Boronicacid, (2-phenylethyl)- (9CI);Ethaneboronic acid, 2-phenyl- (8CI);(2-Phenylethyl)boronic acid;2-Phenylethaneboronic acid;

Chemical Property of Phenethylboronic acid

Chemical Property:

• Vapor Pressure: 0.000179mmHg at 25°C
• Melting Point: 76-81 °C(lit.)
• Refractive Index: 1.587
• Boiling Point: 310.4 °C at 760 mmHg
• PKA: 10.12±0.43(Predicted)
• Flash Point: 141.5 °C
• PSA: 40.46000
• Density: 1.077 g/cm³
• LogP: 0.70190
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C

Purity/Quality:

99% ^*data from raw suppliers

Phenethylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Phenethylboronic acid is a good inhibitor of chymotrypsin. 2-Phenylethylboronic acid is used as a reactant in Suzuki-Miyaura cross-coupling reactions, reactions with α-diazocarbonyl compounds, C-H functionalization of quinones, cross-coupling with aromatic amines and arylation & alkylation of diphenylisoxazole. It has been also used as reactant in studies of the stability of boronic esters to hydrolysis. Reactant involved in:? ;Suzuki-Miyaura cross-coupling reactions1? ;Reactions with α-diazocarbonyl compounds2? ;C-H functionalization of quinones3? ;Cross-coupling with aromatic amines4? ;Arylation and alkylation of diphenylisoxazole5Reactant used in studies of the stability of boronic esters to hydrolysis6

Technology Process of Phenethylboronic acid

There total 13 articles about Phenethylboronic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

potassium trifluoro(phenethyl)borate → (2-phenylethyl)boronic acid (34420-17-2)

Guidance literature:

With aluminum oxide; water; at 70 ℃; for 0.25h; Microwave irradiation;

DOI:10.1016/j.tetlet.2009.09.008

Reference yield: 86.0%

water (7732-18-5) + potassium trifluoro(phenethyl)borate → (2-phenylethyl)boronic acid (34420-17-2)

Guidance literature:

With montmorillonite K₁₀; at 25 ℃; for 1h;

DOI:10.21577/0103-5053.20180126

Reference yield: 75.0%

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) → (2-phenylethyl)boronic acid (34420-17-2)

Guidance literature:

styrene; With dichloroborane dioxane complex; In dichloromethane; for 4h; Heating;

With water; cooling;

DOI:10.1016/j.tetlet.2003.08.086

upstream raw materials:

phenethylmagnesium bromide

boric acid tributyl ester

styrene

4,4,5,5-tetramethyl-2-phenethyl-1,3,2-dioxaborolane

Downstream raw materials:

C₁₅H₁₂Cl₂O

C₁₇H₁₂F₆O

N-benzyl-4-methyl-2-(2-oxo-4-phenethylpyridin-1(2H)-yl)thiazole-5-carboxamide

N-benzyl-3-methyl-5-(2-oxo-4-phenethylpyridin-1(2H)-yl)thiophene-2-carboxamide

Refernces

• 1、 Havare, Nizam,Kano, Naokazu,Morokuma, Keiji,O'Brien, Nathan J.,Ramozzi, Romain,Uematsu, Ryohei. "Synthesis, Structure and Reactivities of Pentacoordinated Phosphorus–Boron Bonded Compounds". . . Retrieved 2020/04/29.
• 2、 Pan, Yue,Jia, Kunfang,Chen, Yali,Chen, Yiyun. "Investigations of alkynylbenziodoxole derivatives for radical alkynylations in photoredox catalysis". supporting information. p. 1215 - 1221. Retrieved 2018/06/13.