34420-17-2

Basic information

• Product Name: Phenethylboronic acid
• Synonyms: 2-PHENYL-1-ETHYLBORONIC ACID;2-PHENYLETHANEBORONIC ACID;2-PHENYLETHYL-1-BORONIC ACID;2-PHENYLETHYLBORONIC ACID;RARECHEM AH PB 0199;PHENYLETHANEBORONIC ACID;PHENETHYLBORONIC ACID;Phenylethylboronic acid
• CAS NO: 34420-17-2
• Molecular Formula: C₈H₁₁BO₂
• Molecular Weight: 149.98
• Product Categories: blocks;BoronicAcids;Boronic acids;Aryl;Boronic acid;Organoborons;Alkyl;Boronic Acids;Boronic Acids and Derivatives;Alkyl Boronic Acids;Boronic Acids and Derivatives;Chemical Synthesis;Organometallic Reagents;OLED materials,pharm chemical,electronic
• Mol File: 34420-17-2.mol
• Article Data: 13

Chemical Properties

• Melting Point: 76-81 °C(lit.)
• Boiling Point: 310.4 °C at 760 mmHg
• Flash Point: 141.5 °C
• Appearance: /
• Density: 1.077 g/cm³
• Vapor Pressure: 0.000179mmHg at 25°C
• Refractive Index: 1.587
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• PKA: 10.12±0.43(Predicted)
• CAS DataBase Reference: Phenethylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: Phenethylboronic acid(34420-17-2)
• EPA Substance Registry System: Phenethylboronic acid(34420-17-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 34420-17-2(Hazardous Substances Data)

Usage

Chemical Properties

off-white powder

Uses

Different sources of media describe the Uses of 34420-17-2 differently. You can refer to the following data:
1. Phenethylboronic acid is a good inhibitor of chymotrypsin.
2. 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.
3. 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

InChI:InChI=1/C8H9BO2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-7,10-11H/b7-6+

Upstream product

• 4363-35-3 Dihydroxy-styryl-boran 
• 7732-18-5 water 
• 100-42-5 styrene 
• 14044-65-6 borane-THF 
• 55671-55-1 dibromoborane dimethylsulfide 
• 103-63-9 1-phenyl-2-bromoethane 
• 165904-22-3 4,4,5,5-tetramethyl-2-phenethyl-1,3,2-dioxaborolane 
• 3277-89-2 phenethylmagnesium bromide 
• 688-74-4 boric acid tributyl ester 

Downstream Products

• 14310-21-5 1-(4-methoxyphenyl)-2-phenylethane 
• 14310-29-3 1-nitro-4-phenethylbenzene 
• 244782-33-0 (3aS,4S,6S,7aR)-3a,5,5-trimethyl-2-(2-phenylethyl)hexahydro-4,6-methano-1,3,2-benzodioxaborole 
• 1146543-18-1 4-phenethyl-pyrrolo[1,2-a]quinoline 
• 1186624-78-1 14-phenethyl-13,15-dioxa-14-boradispiro[5.0.5.3]pentadecane 
• 1311272-65-7 C₅₇H₉₅N₁₁O₁₂ 
• 1579-80-2 (3,3,3-trifluoropropyl)benzene 
• 1415646-33-1 5-phenethyl-12-phenyltetracene 
• 60-12-8 2-phenylethanol 
• 167558-24-9 <18O>-2-phenylethanol 
• 76541-76-9 tetraethyl 4-phenylbutylidene 1,1-diphosphonate 
• 143425-74-5 1-(2',4',6'-trimethylphenyl)-2-phenylethane 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 4765-57-5 2-phenethylquinazolin-4(3Η)-one 

Relevant articles and documents

Dichloroborane-dioxane: An exceptional reagent for the preparation of alkenyl- and alkylboronic acids

Terminal alkynes and alkenes were conveniently hydroborated to the corresponding alkenyl- and alkyldichloroboranes using dichloroborane-dioxane in dichloromethane. These dichloroboranes were hydrolyzed by water to the corresponding alkenyl- and alkylboron

Synthesis, Structure and Reactivities of Pentacoordinated Phosphorus–Boron Bonded Compounds

The isolation and reactivities of two pentacoordinated phosphorus–tetracoordinated boron bonded compounds were explored. A highly Lewis acidic boron reagent and electron-withdrawing ligand system were required to form the pentacoordinated phosphorus state of the P–B bond. The first compound, a phosphoranyl-trihydroborate, gave a THF stabilised phosphoranyl-borane intermediate upon a single hydride abstraction in THF. This compound could undergo a unique rearrangement, which involved a two-fold ring expansion, to give a fused bicyclic compound or it could act as a mono-hydroboration reagent. The hydroboration reactivity of the intermediate was found to be higher towards alkynes vs. alkenes, with good to moderate regioselectivity towards the terminal carbon. The second compound, a phosphoranyl-triarylborate, was found to have different reactivity as it was highly stable towards acids and bases. This is thought to be due to the large bulk around the P–B bond as shown in the crystal structure.

Investigations of alkynylbenziodoxole derivatives for radical alkynylations in photoredox catalysis

The alkynylbenziodoxole derivatives are recently developed alkynylation reagents in organic synthesis, which demonstrate excellent radical alkynylation reactivity in photoredox catalysis reactions. Herein we report the synthesis of alkynylbenziodoxole derivatives with difluoro, monofluoro, monomethoxy, and dimethoxy substitution on the benziodoxole moiety, and investigated their radical alkynylation reactivity for the first time. A series of mechanistic experiments were conducted to study the radical acceptor and oxidative quencher reactivity of alkynylbenziodoxoles, in which unsubstituted alkynylbenziodoxoles played balancing roles in both processes, while electron-rich benziodoxole derivatives demonstrate synthetic advantages in some cases.