949-38-2

Usage

Appearance

White solid

Molecular weight

216.68 g/mol

Uses

a. Intermediate in the synthesis of pharmaceuticals
b. Intermediate in the synthesis of agrochemicals
c. Intermediate in the synthesis of other organic compounds
d. Production of dyes and pigments

Toxicity

Moderate toxicity

Safety precautions

Handle with care and follow proper safety and handling practices

Upstream product

• 95-57-8 2-monochlorophenol 
• 3204-68-0 benzyldimethylphenylammonium chloride 
• 100-44-7 benzyl chloride 
• 1193-00-6 sodium 4-chlorophenolate 
• 100-39-0 benzyl bromide 
• 40400-13-3 2-Iodobenzyl bromide 

Downstream Products

• 26926-56-7 4-(3-benzyloxy-phenyl)-morpholine 
• 20967-96-8 2-(3-benzyloxyphenyl)acetonitrile 
• 32045-70-8 4-(5-benzyloxy-1,3,4,8b-tetrahydro-2H-biphenylen-4a-yl)-morpholine 
• 32045-69-5 2-(3-Benzyloxyphenyl)-cyclohexanon 
• 4525-75-1 2-chlorophenyl acetate 
• 1239569-26-6 2-(2-(benzyloxy)phenyl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 95-57-8 2-monochlorophenol 
• 100-39-0 benzyl bromide 
• 6954-45-6 (2-chlorophenyl)(phenyl)methanol 
• 1484-26-0 3-(benzyloxy)aniline 

Relevant academic research and scientific papers

Visible light mediated synthesis of 6H-benzo[c]chromenes: transition-metal-free intramolecular direct C-H arylation

A synthetic approach towards the 6H-benzo[c]chromene ring under visible light and transition-metal-free conditions has been developed. Benzochromenes are synthesized from the corresponding (2-halobenzyl) phenyl ethers or (2-halophenyl) benzyl ethers using

Organic Photoredox Catalysis for Pschorr Reaction: A Metal-Free and Mild Approach to 6 H-Benzo[ c[chromenes

An expedient organic photoredox Pschorr reaction has been developed that opens up a synthetic route to 6 H-benzo[ c[chromenes. The process can be performed under mild conditions by using eosin Y as a photoredox catalyst and acetonitrile as the solvent. Th

Exploring the Reactivity of α-Lithiated Aryl Benzyl Ethers: Inhibition of the [1,2]-Wittig Rearrangement and the Mechanistic Proposal Revisited

By carefully controlling the reaction temperature, treatment of aryl benzyl ethers with tBuLi selectively leads to α-lithiation, generating stable organolithiums that can be directly trapped with a variety of selected electrophiles, before they can undergo the expected [1,2]-Wittig rearrangement. This rearrangement has been deeply studied, both experimentally and computationally, with aryl α-lithiated benzyl ethers bearing different substituents at the aryl ring. The obtained results support the competence of a concerted anionic intramolecular addition/elimination sequence and a radical dissociation/recombination sequence for explaining the tendency of migration for aryl groups. The more favored rearrangements are found for substrates with electron-poor aryl groups that favor the anionic pathway.

Choline chloride based deep eutectic solvent as an efficient solvent for the benzylation of phenols

Deep eutectic solvents (such as the combination of urea and choline chloride) are found to be promising solvent and phase-transfer-media for benzylation of phenol. These methods avoided the complexity of multiple alkylations giving selectively O-alkylated aromatic products. Good to excellent yields of the corresponding benzyl phenyl ether were obtained. The non-toxic, biodegradable, inexpensive, and recyclable nature of DES make this protocol green and cost-effective.

NiCl2·6H2O/NaBH4 in methanol: A mild and efficient strategy for chemoselective deallylation/debenzylation of aryl ethers

Deprotection of allyl/benzyl aryl ethers was achieved chemoselectively. The mild and inexpensive reagent combination of NiCl2·6H 2O/NaBH4 in methanol afforded the products in high yields, within a reaction time of 5-10 min.

Metal-free chlorodeboronation of organotrifluoroborates

A mild and metal-free method for the chlorodeboronation of organotrifluoroborates using trichloroisocyanuric acid (TCICA) was developed. Aryl-, heteroaryl-, alkenyl-, alkynyl-, and alkyltrifluoroborates were converted into the corresponding chlorinated products in good yields. This method proved to be tolerant of a broad range of functional groups.

Counterattack mode differential acetylative deprotection of phenylmethyl ethers: Applications to solid phase organic reactions

A counterattack protocol for differential acetylative cleavage of phenylmethyl ether has been developed. The phenylmethyl moiety is liberated as benzyl bromide that is isolated and reused providing advantages in terms of waste minimization/utilization and atom economy. The applicability of this methodology has been extended for solid phase organic reactions with the feasibility of reuse of the solid support.

THE SALT-FREE SYNTHESIS OF ARYL ETHERS USING METHYL TRICHLOROACETATE

Metyl trichloroacetate is an effective reagent for salt-free synthesis of aryl ethers and anisoles from phenols.

THE EFFECT OF CHANGES IN HYDRODYNAMIC CONDITIONS ON THE RESPONSE OF CALCIUM-SELECTIVE MEMBRANE ELECTRODES WITH A MACROCYCLIC CARRIER

Shifts of the potentials of a calcium ion-selective electrode based on the complex of 7,19-dibenzyl-2,2,3,3-tetramethyl-7,19-diaza-1,4,10,13,16-pentaoxacycloheneicosane-6,20-dione with calcium tetra(4-chlorophenyl)borate in various membrane solvents caused by changes in hydrodynamic conditions in the measured solution were examined.The use of 2-fluoro-2'-nitrodiphenyl ether as a membrane solvent combined with substitution of benzyl groups with octyl ones in the neutral carrier eliminates this unfavourable phenomenon while preseving the selectivity parameters of the elect rode.