847560-49-0

Basic information

• Product Name: 4-Benzyloxy-2-methylphenylboronic acid
• Synonyms: 4-BENZYLOXY-2-METHYLPHENYLBORONIC ACID;4-BENZYLOXY-2-METHYLBENZENEBORONIC ACID;AKOS BRN-0589;5-Benzyloxytoluene-2-boronic acid
• CAS NO: 847560-49-0
• Molecular Formula: C₁₄H₁₅BO₃
• Molecular Weight: 242.08
• Product Categories: blocks;BoronicAcids;Boronic acid;Aryl;Organoborons
• Mol File: 847560-49-0.mol
• Article Data: 2

Chemical Properties

• Melting Point: 154-158
• Boiling Point: 436.2°C at 760 mmHg
• Flash Point: 217.6°C
• Appearance: /
• Density: 1.17g/cm³
• Vapor Pressure: 2.22E-08mmHg at 25°C
• Refractive Index: 1.585
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: DMSO (Slightly)
• PKA: 8.78±0.58(Predicted)
• CAS DataBase Reference: 4-Benzyloxy-2-methylphenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Benzyloxy-2-methylphenylboronic acid(847560-49-0)
• EPA Substance Registry System: 4-Benzyloxy-2-methylphenylboronic acid(847560-49-0)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36/37/39-36
• HazardClass: IRRITANT, IRRITANT-HARMFUL
• Hazardous Substances Data: 847560-49-0(Hazardous Substances Data)

Usage

Description

4-Benzyloxy-2-methylphenylboronic acid is an organic boronic acid compound that features a benzyloxy group at the 4-position and a methyl group at the 2-position on a phenyl ring. It is known for its reactivity in organic synthesis and its potential applications in medicinal chemistry.

Uses

Used in Organic Synthesis:
4-Benzyloxy-2-methylphenylboronic acid is used as a reagent in the Suzuki reaction, a type of cross-coupling reaction that facilitates the formation of carbon-carbon bonds. This reaction is crucial for the synthesis of various organic compounds, including pharmaceuticals and agrochemicals.
Used in Medicinal Chemistry:
4-Benzyloxy-2-methylphenylboronic acid is used in the development of Phenyl-oxazoles, a family of H3R inverse agonists that exhibit anti-amnesic effects. These compounds have potential therapeutic applications in the treatment of cognitive disorders and memory impairments.

InChI:InChI=1/C14H15BO3/c1-11-9-13(7-8-14(11)15(16)17)18-10-12-5-3-2-4-6-12/h2-9,16-17H,10H2,1H3

Upstream product

• 14472-14-1 4-bromo-3-methylphenol 
• 17671-75-9 4-(benzyloxy)-1-bromo-2-methylbenzene 
• 100-39-0 benzyl bromide 

Downstream Products

• 309947-24-8 4-(4'-Benzyloxy-2'-methylbiphenyl-4-yloxymethyl)-2,2-dimethyl-1,3-dioxolane 
• 309947-35-1 4-[2'-Methyl-4'-(4-methylbenzyloxy)biphenyl-4-yloxymethyl]-2,2-dimethyl-1,3-dioxolane 
• 309947-37-3 4-[2'-Methyl-4'-(3-methylbenzyloxy)biphenyl-4-yloxymethyl]-2,2-dimethyl-1,3-dioxolane 
• 1209484-76-3 C₂₃H₂₆N₂O₂ 
• 1283146-32-6 2-((2S,4S)-1-(4-(4-(benzyloxy)-2-methylphenoxy)phenyl)-4-(trifluoromethyl)pyrrolidin-2-yl)acetonitrile 
• 1609259-46-2 2-[4-(benzyloxy)-2-methylphenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Relevant articles and documents

Crisaborole intermediate, preparation method and application of crisaborole intermediate in preparation of crisaborole

The invention discloses a crisaborole intermediate, a preparation method and application of the crisaborole intermediate in preparation of crisaborole. The crisaborole intermediate has a structure asshown in a formula I in the specification. The preparation method comprises the following steps: carrying out Grignard reaction on a compound shown in a structural formula VI in an organic solvent A or carrying out exchange reaction with a metal Grignard reagent, and reacting with borate to obtain a compound shown in a structural formula V; reacting the obtained compound with the structural formula V with pinacol in an organic solvent B to obtain a compound with a structural formula IV; removing a protecting group from the compound shown in the structural formula IV in an organic solvent C toobtain a compound shown in a structural formula III; and carrying out a coupling reaction on the compound shown in the structural formula III and 4-halogenated cyanophenyl shown in the structural formula II in an organic solvent D under an alkaline condition to obtain the crisaborole intermediate shown in the structural formula I. The method effectively solves the problems of high production costand low product purity, and is suitable for industrial large-scale production.