27798-38-5

Usage

Chemical structure

Chlorinated derivative of benzene with a benzyl group attached to the third carbon atom

Primary use

Intermediate in the synthesis of other organic compounds (pharmaceuticals and agrochemicals)

Applications

a. Solvent in organic reactions
b. Starting material for the production of dyes and perfumes
c. Building block in the manufacturing of polymers and plastics

Safety precautions

a. Harmful if inhaled, ingested, or absorbed through the skin
b. Can cause irritation to the respiratory system and skin
c. Handle with caution

Upstream product

• 620-20-2 1-Chloro-3-chloromethyl-benzene 
• 71-43-2 benzene 
• 76017-71-5 1-benzyl-5,6,8,9-tetrahydro-7-phenyldibenzoacridinium triflouromethanesulphonate 
• 587-04-2 m-Chlorobenzaldehyde 
• 98-80-6 phenylboronic acid 
• 640-60-8 toluene-4-sulfonic acid phenyl ester 
• 306773-38-6 3-chlorobenzaldehyde hydrazone 
• 591-50-4 iodobenzene 
• 766-80-3 1-bromomethyl-3-chlorobenzene 
• 108-37-2 1-bromo-3-chlorobenzene 
• 100-44-7 benzyl chloride 
• 873-63-2 m-chlorobenzyl alcohol 
• 201230-82-2 carbon monoxide 
• 63503-60-6 3-chlorophenylboronic acid 

Downstream Products

• 1016-78-0 3-chlorobenzophenone 

Relevant academic research and scientific papers

Combined Photoredox/Enzymatic C?H Benzylic Hydroxylations

Chemical transformations that install heteroatoms into C?H bonds are of significant interest because they streamline the construction of value-added small molecules. Direct C?H oxyfunctionalization, or the one step conversion of a C?H bond to a C?O bond, could be a highly enabling transformation due to the prevalence of the resulting enantioenriched alcohols in pharmaceuticals and natural products,. Here we report a single-flask photoredox/enzymatic process for direct C?H hydroxylation that proceeds with broad reactivity, chemoselectivity and enantioselectivity. This unified strategy advances general photoredox and enzymatic catalysis synergy and enables chemoenzymatic processes for powerful and selective oxidative transformations.

Chlorotrimethylsilane and Sodium Iodide: A Remarkable Metal-Free Association for the Desulfurization of Benzylic Dithioketals under Mild Conditions

A novel metal-free process allowing the reductive desulfurization of various benzylic dithioketals to afford diarylmethane and benzylester derivatives with good to excellent yields is reported. At room temperature, this mild reduction process requires only the use of TMSCl and NaI in CH2Cl2 and tolerates a large variety of functional groups. (Figure presented.).

Cross-Coupling of Phenol Derivatives with Umpolung Aldehydes Catalyzed by Nickel

A nickel-catalyzed cross-coupling to construct the C(sp2)-C(sp3) bond was developed from two sustainable biomass-based feedstocks: phenol derivatives with umpolung aldehydes. This strategy features the in situ generation of moisture/air-stable hydrazones from naturally abundant aldehydes, which act as alkyl nucleophiles under catalysis to couple with readily available phenol derivatives. The avoidance of using both halides as the electrophiles and organometallic or organoboron reagents (also derived from halides) as the nucleophiles makes this method more sustainable. Water tolerance, great functional group (ketone, ester, free amine, amide, etc.) compatibility, and late-stage elaboration of complex biological molecules exemplified its practicability and unique chemoselectivity over organometallic reagents.

Nickel-catalyzed cross-coupling of aldehydes with aryl halides: Via hydrazone intermediates

Traditional cross-couplings require stoichiometric organometallic reagents. A novel nickel-catalyzed cross-coupling reaction between aldehydes and aryl halides via hydrazone intermediates has been developed, merging the Wolff-Kishner reduction and the classical cross-coupling reactions. Aromatic aldehydes, aryl iodides and aryl bromides are especially effective in this new cross-coupling chemistry.

Synthesis of zwitterionic palladium complexes and their application as catalysts in cross-coupling reactions of aryl, heteroaryl and benzyl bromides with organoboron reagents in neat water

N-(3-Chloro-2-quinoxalinyl)-N′-arylimidazolium salts (aryl = 2,6-diisopropylphenyl [HL1Cl]Cl, aryl = mesityl [HL2Cl]Cl) have been synthesized by treating 2,3-dichloroquinoxaline with the corresponding N′-arylimidazole in neat water. Facile reactions of these imidazolium salts with Pd(PPh3)4 and Pd2(dba)3/PPh3 (dba = dibenzyledene acetone) at 50 °C have afforded zwitterionic palladium(ii) complexes [Pd(HL1)(PPh3)Cl2] (I) and [Pd(HL2)(PPh3)Cl2] (II) in excellent yields. I and II have been tested for their ability to catalyze Suzuki-Miyaura cross coupling (SMC) reactions in neat water/K2CO3 and are found to be highly active for carrying out these reactions between aryl bromides and organoboron reagents. Furthermore, the scope of the catalyst I was also examined by employing (hetero)aryl bromides, hydrophilic aryl bromides, benzyl bromides and various organoboron reagents. More than 80 aryl/benzyl bromide-arylboronic acid combinations were screened in neat water/K2CO3 and it was found that I was a versatile catalyst, which produced biaryls/diarylmethanes in excellent yields. A TON of 82 000 was achieved by using I. Studies on the mechanism have also been carried out to investigate the involvement of carbene complexes in the catalytic path. Poison tests and a two-phase test were also conducted and the results are reported.

Cobalt-Catalyzed Reductive Cross-Coupling Between Benzyl Chlorides and Aryl Halides

A new protocol for the direct reductive cobalt-catalyzed arylation of benzyl chlorides has been developed in order to form functionalized diarylmethanes. A variety of reactive groups either on the aryl or the benzyl halide was employed. This represents the first cobalt-catalyzed reductive cross-coupling which does not require any ligand and pyridine. A reaction pathway is proposed involving a radical benzyl species. (Figure presented.).

Iron-catalyzed hetero-cross-dehydrogenative coupling reactions of sulfoximines with diarylmethanes: A new route to N-alkylated sulfoximines

An efficient iron-catalyzed C-N bond formation by hetero-cross- dehydrogenative coupling (CDC) between sulfoximines and diarylmethanes is described. The reaction shows good functional group tolerance and provides N-alkylated sulfoximines in moderate to go

Rapid Wolff-Kishner reductions in a silicon carbide microreactor

Wolff-Kishner reductions are performed in a novel silicon carbide microreactor. Greatly reduced reaction times and safer operation are achieved, giving high yields without requiring a large excess of hydrazine. The corrosion resistance of silicon carbide avoids the problematic reactor compatibility issues that arise when Wolff-Kishner reductions are done in glass or stainless steel reactors. With only nitrogen gas and water as by-products, this opens the possibility of performing selective, large scale ketone reductions without the generation of hazardous waste streams.

Microwave-promoted palladium catalysed Suzuki cross-coupling reactions of benzyl halides with arylboronic acid

Simple catalytic systems for the coupling of benzyl halides with phenylboronic acid under microwave conditions were tested. Microwave-promoted Suzuki reaction of arylboronic acid with benzyl halides catalysed by PdCl2(PPh3)2 in the mixed solvents DMF/H2O is reported to give diaryl methane derivatives in good to high yield.

Indium(III) triflate - A catalyst for greener aromatic alkylation reactions

An environmentally friendly method for alkylating aromatic compounds with simple alcohols in the presence of a catalytic amount of indium(III) triflate is reported. Ionic liquids are used as solvents and energy-efficient heating is provided by microwave radiation. Good yields are obtained with benzyl, secondary, and tertiary alcohols. Simple primary alcohols are not effective alkylating agents under these conditions. With tertiary alcohols, activated aromatic compounds such as toluene and anisole must be used to obtain good yields. The catalyst, which is immobilized in a water-insoluble ionic liquid, can be easily recycled without significant loss of activity.