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100-44-7

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100-44-7 Usage

Chemical Description

Different sources of media describe the Chemical Description of 100-44-7 differently. You can refer to the following data:
1. Benzyl chloride is a colorless liquid used in organic synthesis.
2. Benzyl chloride is an organic compound that is used as a precursor to various chemicals, including benzyl alcohol.

Chemical Properties

Benzyl chloride is a colorless to s lightly yellow liquid with a strong, unpleasant, irritating odor. The Odor Threshold is 0.05 ppm.The stabilized form of benzyl chloride contains a fixed amount of a sodium carbonate solution or propylene oxide.

Physical properties

Colorless to pale yellowish-brown liquid with a pungent, aromatic, irritating odor. Odor threshold concentration is 47 ppbv (Leonardos et al., 1969). Katz and Talbert (1930) reported an experimental detection odor threshold concentration of 210 μg/m3 (41 ppbv). The solubility of benzyl chloride in water is 0.33 g/L at 4°C, 0.49 g/L at 20°C, and 0.55 g/L at 30°C. It is freely soluble in chloroform, acetone, acetic acid esters, diethyl ether, and ethyl alcohol.

Uses

Benzyl chloride is used in the manufacture of benzyl Compounds, dyes, artificial resins, tanning agents, phar maceuticals, plasticizers, synthetic tannins, perfumes, lubricants, and quaternary ammonium compounds. It is also an intermediate in the preparation of phenylacetic acid (precursor to phamaceuticals).

Definition

ChEBI: Benzyl chloride is a member of the class of benzyl chlorides that is toluene substituted on the alpha-carbon with chlorine.

Preparation

Benzyl chloride is the starting material for a large number of industrial syntheses. The first preparation of it involved not the chlorination of toluene, however, but the reaction of benzyl alcohol with hydrochloric acid (S. Cannizzaro, 1853). Today, most side-chain chlorination of toluene to produce benzyl chloride. Dibenzyl ether is formed as a byproduct in the alkaline hydrolysis of benzyl chloride to benzyl alcohol. This ether can be re-converted to benzyl chloride by cleavage with hydrogen chloride at a temperature below 100°C.

Production Methods

Benzyl chloride can be synthesized by chloromethylation of benzene in the presence of a catalyst (ZnCl2) or by treatment of benzyl alcohol with SO2Cl2. Commercially it is produced by chlorination of boiling toluene in the presence of light.

Application

Benzyl chloride is used mainly to produce plasticizers (e.g., benzyl butyl phthalate), benzyl alcohol, and phenylacetic acid via benzyl cyanide (used in the production of synthetic penicillin). On a smaller scale, it is used to produce quaternary ammonium salts (for disinfectants and phase-transfer catalysts), benzyl esters (benzyl benzoate and benzyl acetate for the flavors and perfumes industry), dyes of the triphenylmethane series, dibenzyl disulfide (antioxidant for lubricants), benzylphenol, and benzylamines.

Reactions

Benzyl chloride can be oxidized to benzoic acid or benzaldehyde, or substituted to give the halogenated, sulfonated or nitrated product.With NH3 it yields mono-, di- or tribenzyl amine. With alcohols in base the benzylalkyl ether is formed. With phenols either the phenolic or nuclear hydrogens can react to give benzylaryl ether or benzylated phenols. Reaction with NaCN gives benzyl cyanide (phenylacetonitrile); with aliphatic primary amines the product is the N-alkylbenzylamine, and with aromatic primary amines N-benzylaniline is formed. Benzyl chloride is converted to butyl benzyl phthalate plasticizer and other chemicals.

Synthesis Reference(s)

The Journal of Organic Chemistry, 29, p. 3692, 1964 DOI: 10.1021/jo01035a504Synthetic Communications, 16, p. 1173, 1986 DOI: 10.1080/00397918608056363Tetrahedron Letters, 29, p. 5783, 1988 DOI: 10.1016/S0040-4039(00)82191-7

General Description

Benzyl chloride appears as a colorless liquid with an irritating odor. Toxic by inhalation and skin absorption. Flash point 153°F. Slightly soluble in water. Corrosive to metals and tissue. A lachrymator. Density 9.2 lb /gal.

Air & Water Reactions

A lachrymator. Slightly soluble in water.

Reactivity Profile

Halogenated aliphatic compounds, such as Benzyl chloride, are moderately or very reactive. Reactivity generally decreases with increased degree of substitution of halogen for hydrogen atoms. Materials in this group are incompatible with strong oxidizing and reducing agents. Also, they are incompatible with many amines, nitrides, azo/diazo compounds, alkali metals, and epoxides.

Hazard

Highly toxic, intense eye and skin irritant. A lachrymator. Upper respiratory tract irritant. Prob- able carcinogen.

Health Hazard

Benzyl chloride is a corrosive liquid. Con tact with the eyes can cause corneal injury.Exposure to its vapors can produce intenseirritation of the eyes, nose, and throat. Highconcentrations may cause lung edema anddepression of the central nervous system.Flury and Zernik (1931) stated that exposureto 16 ppm for 1 minute was intolerable tohumans. The LC50 values for a 2-hour expo sure in mice and rats are 80 and 150 ppm,respectively. The subcutaneous LD50 valuein rats is 1000 mg/kg (NIOSH 1986).Benzyl chloride tested positive to thehistidine reversion–Ames test for mutagenic ity. Subcutaneous administration of this com pound in laboratory animals caused tumors atthe site of application.

Fire Hazard

Benzyl chloride burns but does not ignite readily. Benzyl chloride may ignite combustibles. When heated to decomposition, Benzyl chloride emits toxic and corrosive fumes. Some organic chlorides decompose to yield phosgene. Incompatible with active metals such as copper, aluminum, magnesium, iron, zinc, and tin and keep from strong oxidizing agents. Avoid contact with acids or acid fumes. Keep separate from oxidizing materials. May become unstable at elevated temperatures and pressures; may react with water resulting in some nonviolent release of energy. Polymerizes with evolution of heat and hydrogen chloride when in contact with all common metals except nickel and lead.

Potential Exposure

Used as an intermediate and as an irritant gas in chemical warfare. In contrast to phenyl halides, benzyl halides are very reactive. Benzyl chloride is used in production of benzal chloride, benzyl alcohol, and benzaldehyde. Industrial usage includes the manufacture of benzyl compounds, cosmetics, dyes, plastics, synthetic tannins, perfumes and resins. It is used in the manufacture of many pharmaceuticals. Suggested uses of benzyl chloride include: the vulcanization of fluororubbers and the benzylation of phenol and its derivatives for the production of possible disinfectants.

Carcinogenicity

Benzyl chloride caused genetic mutations and chromosome-damaging effects in a wide variety of in vitro assays; it was not mutagenic in vivo in the mouse micronucleus assay

Source

As of October 1996, benzyl chloride was listed for regulation but no MCLGs or MCLs have been proposed (U.S. EPA, 1996). Reported as an impurity (≤ 0.05 wt %) in 98.5 wt % benzyl mercpatan (Chevron Phillips, April 2005).

Environmental fate

Biological. When incubated with raw sewage and raw sewage acclimated with hydrocarbons, benzyl chloride degraded forming nonchlorinated products (Jacobson and Alexander, 1981). Chemical/Physical. Anticipated products from the reaction of benzyl chloride with ozone or OH radicals in the atmosphere are chloromethyl phenols, benzaldehyde and chlorine radicals (Cupitt, 1980). Slowly hydrolyzes in water forming HCl and benzyl alcohol. The estimated hydrolysis half-life in water at 25 °C and pH 7 is 15 h (Mabey and Mill, 1978). The hydrolysis rate constant for benzyl chloride at pH 7 and 59.2 °C was determined to be 0.0204/min, resulting in a half-life of 34 min (Ellington et al., 1986). May polymerize in contact with metals except nickel and lead (NIOSH, 1997). When heated to decomposition, hydrogen chloride gas may be released (CHRIS, 1984).

Shipping

UN1738 Benzyl chloride, Hazard class: 6.1; Labels: 6.1—Poisonous materials, 8—Corrosive material.

Purification Methods

Dry it with MgSO4 or CaSO4, or reflux it with fresh Ca turnings, then fractionally distil it under reduced pressure, collecting the middle fraction and storing it over CaH2 or P2O5. It has also been purified by passage through a column of alumina. Alternatively it is dried over MgSO4 and distilled in a vacuum. The middle fraction is degassed by several freeze-thaw cycles and then fractionated in an 'isolated fractionating column' (which has been evacuated and sealed off at ~10-6 mm) over a steam bath. The middle fraction is retained. The final samples are distilled in a vacuum from this sample and again retaining the middle fraction. The purity is >99.9% (no other peaks are visible by GLC, and the NMR spectrum is consistent with the structure. [Mohammed & Kosower J Am Chem Soc 93 1709 1971, Beilstein 5 IV 809.] IRRITANT and strongly LACHRYMATORY.

Incompatibilities

May form explosive mixture with air. Contact with water forms hydrogen chloride fumes. Strong oxidizers may cause fire and explosions. Unstabilized benzyl chloride undergoes polymerization with copper, aluminum, iron, zinc, magnesium, tin, and other common metals except lead and nickel, with the liberation of heat and hydrogen chloride gas. May accumulate static electrical charges, and may cause ignition of its vapors. Attacks some plastics and rubber. Thermal decomposition and polymerization reactions are inhibited, to a limited extent, by addition of triethylamine, propylene oxide, or sodium carbonate.

Waste Disposal

Incineration @ 816 C for 0.5 second minimum for primary combustion and 1204 C for 12.0 second for secondary combustion. Elemental chlorine formation may be alleviated by injection of steam or methane into the combustion process.

Check Digit Verification of cas no

The CAS Registry Mumber 100-44-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 0 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 100-44:
(5*1)+(4*0)+(3*0)+(2*4)+(1*4)=17
17 % 10 = 7
So 100-44-7 is a valid CAS Registry Number.
InChI:InChI=1/C7H7Cl/c8-6-7-4-2-1-3-5-7/h1-5H,6H2

100-44-7 Well-known Company Product Price

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  • (Code)Product description
  • CAS number
  • Packaging
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  • Detail
  • TCI America

  • (B0412)  Benzyl Chloride (stabilized with ε-Caprolactam)  >99.0%(GC)

  • 100-44-7

  • 25g

  • 120.00CNY

  • Detail
  • TCI America

  • (B0412)  Benzyl Chloride (stabilized with ε-Caprolactam)  >99.0%(GC)

  • 100-44-7

  • 500g

  • 170.00CNY

  • Detail
  • Alfa Aesar

  • (A12481)  Benzyl chloride, 99%, stab.   

  • 100-44-7

  • 500g

  • 207.0CNY

  • Detail
  • Alfa Aesar

  • (A12481)  Benzyl chloride, 99%, stab.   

  • 100-44-7

  • 2500g

  • 530.0CNY

  • Detail
  • Alfa Aesar

  • (A12481)  Benzyl chloride, 99%, stab.   

  • 100-44-7

  • 10000g

  • 1823.0CNY

  • Detail
  • Aldrich

  • (185558)  Benzylchloride  ReagentPlus®, 99%, contains ≤1% propylene oxide as stabilizer

  • 100-44-7

  • 185558-50G

  • 321.75CNY

  • Detail
  • Aldrich

  • (185558)  Benzylchloride  ReagentPlus®, 99%, contains ≤1% propylene oxide as stabilizer

  • 100-44-7

  • 185558-250G

  • 347.49CNY

  • Detail
  • Aldrich

  • (185558)  Benzylchloride  ReagentPlus®, 99%, contains ≤1% propylene oxide as stabilizer

  • 100-44-7

  • 185558-1KG

  • 500.76CNY

  • Detail

100-44-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name benzyl chloride

1.2 Other means of identification

Product number -
Other names Benzene, (chloromethyl)-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Benzyl chloride is used as a chemical intermediate in the manufacture of certain dyes and pharmaceutical, perfume and flavor products. It is also used as a photographic developer. Benzyl chloride can be used in the manufacture of synthetic tannins and as a gum inhibitor in petrol. Benzyl chloride has been used as an irritant gas in chemical warfare.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:100-44-7 SDS

100-44-7Relevant articles and documents

Photocatalytic oxidation of alkanes with dioxygen by visible light and copper(II) and iron(III) chlorides: Preference oxidation of alkanes over alcohols and ketones

Takaki, Ken,Yamamoto, Jun,Komeyama, Kimihiro,Kawabata, Tomonori,Takehira, Katsuomi

, p. 2251 - 2255 (2004)

Visible light irradiation of alkanes in acetonitrile with CuCl2 and FeCl3 catalysts under atmospheric dioxygen gave the corresponding alcohols and ketones effectively; in these reactions, the total selectivity of the products did not decrease so much with increase of alkane conversion. For example, cyclohexanol and cyclohexanone were formed with ca. 70% selectivity at 50% conversion, because overoxidation of the products took place more slowly than cyclohexane oxidation. The relative reactivity values of cycloalkanes increased as their ring-sizes decreased. In the oxidation of hexane, the reactivity ratio of C1-/C2-/C3-H was found to be 1.0/1.4/1.8 with CuCl2 and 1.0/4.6/6.6 with FeCl3, respectively. Toluene and diphenylmethane were more reactive than cyclohexane with FeCl3, as expected, whereas the alkane was oxidized faster than the benzylic compounds in the separate reaction with CuCl2. Moreover, the alkane oxidation could be comparably performed by sunlight instead of an artificial lamp.

Formation of Benzylic Chlorides by Rearrangement of Cycloheptatrienes with Tellurium Tetrachloride

Albeck, Michael,Tamari, Tova,Sprecher, Milon

, p. 2276 - 2278 (1983)

-

Vitamin B12 Catalyzed Atom Transfer Radical Addition

Proinsias, Keith O.,Jackowska, Agnieszka,Radzewicz, Katarzyna,Giedyk, MacIej,Gryko, Dorota

, p. 296 - 299 (2018)

Vitamin B12, a natural Co-complex, catalyzes atom transfer radical addition (ATRA) of organic halides to olefins. The established conditions were found to be very selective, with atom transfer radical polymerization (ATRP) occurring only in the case of acrylates.

Investigation of the stability of the Corey-Kim intermediate

Cink, Russell D.,Chambournier, Gilles,Surjono, Herman,Zhenglong, Xiao,Richter, Steve,Naris, Marius,Bhatia, Ashok V.

, p. 270 - 274 (2007)

-

-

Walling,Jacknow

, p. 6108 (1960)

-

-

Johnson,Douglass

, p. 2548 (1939)

-

Diphenylphosphinated Ethylene Oligomers as polymeric Reagents for Synthesis of Alkyl Chlorides from Alcohols

Bergbreiter, David E.,Blanton, James R.

, p. 337 - 338 (1985)

Diphenylphosphinated ethylene oligomers can be used as homogeneous polymeric reagents at 90 deg C in carbon tetrachloride to form alkyl chlorides from alcohols and since these funcionalized ethylene oligomers precipitate quantitatively from solution at 25 deg C, they can be easily recovered and separated from the reaction products and can be partially recycled.

-

Downie,Lee

, p. 4951 (1968)

-

A convenient method for producing mono- and dichlorohydrins from glycerol

Giomi, Donatella,Malavolti, Marino,Piccolo, Oreste,Salvini, Antonella,Brandi, Alberto

, p. 46319 - 46326 (2014)

A new method for the transformation of glycerol into mono- and dichlorohydrins has been studied. With trimethylchlorosilane as chlorinating agent and acetic acid as catalyst, mono- and dichlorohydrins have been obtained in high yields and selectivity. In fact, under different reaction conditions, the synthesis of α-monochlorohydrin (3-chloropropan-1,2-diol) or α,γ-dichlorohydrin (1,3-dichloropropan-2-ol) as predominant product has been achieved. This process was also exploited for the valorisation of the crude mixture of glycerol and monochlorohydrin (glyceric mixture), a by-product from an earlier BioDiesel production. A reaction mechanism has been proposed based on investigations on the chlorination of different alcohols.

-

Hancock,K.G.,Dickinson,D.A.

, p. 962 - 963 (1972)

-

Kinetic study of the reactions of chlorine atoms and Cl2.- radical anions in aqueous solutions. II. Toluene, benzoic acid, and chlorobenzene

Martire,Bertolotti,Carrillo Le Roux,Braun,Rosso,Bertolotti,Carrillo Le Roux,Braun,Gonzalez

, p. 5385 - 5392 (2001)

The reactions of chlorine atoms and Cl2.- radical ions with toluene, benzoic acid, and chlorobenzene were studied using laser conventional flash photolysis of Na2S2O8 aqueous solutions containing Cl- ions. The reaction rate constants was diffusion-controlled, thus showed no dependence on the σ-Hammett parameter of the substituent in the aromatic ring. The high reactivity of Cl atoms was distinct with that of Cl2.- radical ions, for which the rate constants for the reactions with the substituted benzenes were -/M-sec. The π-complex of benzene yielded very low bond energies (a sequence of chemical reactions unless highly stabilized by the solvent. An electron-transfer reaction pathway was not important for the substrates benzene, toluene, and benzoic acid since phenolic derivatives formed from the disproportionation of HO-CHD radicals were not observed as reaction products. The dissimilarity in the behavior of the Cl-CHD radicals in the gas phase and in organic solvents compared with that in the aqueous phase seemed to be the lack of dissociation of Cl-CHD in aqueous solutions.

-

Brocklehurst et al.

, p. 2017 (1964)

-

The halogenation of aliphatic C-H bonds with peracetic acid and halide salts

He, Yu,Goldsmith, Christian R.

, p. 1377 - 1380 (2010)

Hydrocarbons react with molar concentrations of peracetic acid and halide salts to yield predominantly monohalogenated products under optimum conditions, with chlorination being more oxidatively efficient than bromination. The alkane halogenation proceeds at ambient temperature and does not require a heavy-metal catalyst. The observed reactivity is consistent with a radical mechanism, in which the peracid initially reacts with the halide ions to yield halogen-atom radicals, which ultimately oxidize the hydrocarbon. Although the reactivity proceeds slightly more efficiently in acetonitrile, the halogenation protocol works well in water.

Practical conversion of chlorosilanes into alkoxysilanes without generating HCl

Wakabayashi, Ryutaro,Sugiura, Yasushi,Shibue, Toshimichi,Kuroda, Kazuyuki

, p. 10708 - 10711 (2011)

Alcohol-free: A versatile, efficient, and practical synthesis of alkoxysilanes without generation of HCl involves the reaction of chlorosilanes with unsymmetrical ethers in the presence of a Lewis acid (see scheme). The reaction proceeds through selective cleavage of C-O bonds and is superior to conventional processes. Industrially feasible reagents are used and only one by-product results. Copyright

-

Halford,Reid

, p. 1873,1876 (1941)

-

Elliott,Speakman

, p. 641,647,649 (1940)

-

Gruselle,Nedelec

, p. 1813,1814 (1978)

-

BiCl3 : An efficient agent for selective chlorination of alcohols or for halogen exchange reaction

Boyer, Bernard,Keramane, El Mehdi,Montero, Jean-Louis,Roque, Jean-Pierre

, p. 1737 - 1741 (1998)

BiCl3 was found to be an effective reagent for an improved chlorination of alcohols and for a convenient halogen exchange reaction.

ESI-MS study on transient intermediates in the fast cyclopropenium- activated chlorination reaction of alcohols

Zhao, Zhi-Xiong,Wang, Hao-Yang,Guo, Yin-Long

, p. 856 - 858 (2011)

-

-

Kwart et al.

, p. 765 (1967)

-

Thermal Decomposition of Allylbenzene Ozonide

Ewing, James C.,Church, Daniel F.,Pryor, William A.

, p. 5839 - 5844 (1989)

Thermal decomposition of allylbenzene ozonide (ABO) at 98 deg C in the liquid phase yields toluene, bibenzyl, phenylacetaldehyde, formic acid, and (benzyloxy)methyl formate as major products; benzyl chloride is formed when chlorinated solvents are employe

The chemistry of cyclic carbaphosphazenes: The first observation of (R 2PN)(ClCN)2 (R=Cl, Ph) as a reagent for the conversion of alcohols to aldehydes, ketones, and alkyl chlorides

Behera, Nabakrushna,Mishra, Pradyumna Kumar,Elias, Anil J.

, p. 2445 - 2452 (2006)

The oxidation of nine primary and secondary alcohols to the corresponding aldehydes and ketones has been carried out under mild conditions and in good yields using the cyclocarbaphosphazenes (R2PN)(ClCN)2 [R2P = Cl2 P(1), Ph2P(2)] along with dimethylsulfoxide. While both the P-Cl and C-Cl bonds of the carbaphosphazene can in principle bring about the reaction, we observed an increased preference for the C-Cl bonds over the P-Cl bonds in the oxidation of alcohol. Blocking the reactive P site on the heterocyclic ring with the phenyl groups was found to reduce the yields of the oxidized products, while blocking the C- sites with diethylamino groups resulted in no reaction. In addition, along with DMF, the same cyclocarbaphosphazene has been found to be useful for the conversion of alcohols to alkyl chlorides. Copyright Taylor & Francis Group, LLC.

Discovery of novel quinazolinone derivatives as potential anti-HBV and anti-HCC agents

Qiu, Jingying,Zhou, Qingqing,Zhang, Yinpeng,Guan, Mingyu,Li, Xin,Zou, Yueting,Huang, Xuan,Zhao, Yali,Chen, Wang,Gu, Xiaoke

, (2020)

As a continuation of earlier works, a series of novel quinazolinone derivatives (5a-s) were synthesized and evaluated for their in vitro anti-HBV and anti-hepatocellular carcinoma cell (HCC) activities. Among them, compounds 5j and 5k exhibited most potent inhibitory effect on HBV DNA replication in both drug sensitive and resistant (lamivudine and entecavir) HBV strains. Interestingly, besides the anti-HBV effect, compound 5k could significantly inhibit the proliferation of HepG2, HUH7 and SK- cells, with IC50 values of 5.44, 6.42 and 6.75 μM, respectively, indicating its potential anti-HCC activity. Notably, the in vitro anti-HCC activity of 5k were more potent than that of positive control 5-fluorouracil and sorafenib. Further studies revealed that compound 5k could induce HepG2 cells apoptosis by dose-dependently upregulating Bad and Bax expression and decreasing Bcl-2 and Bcl-xl protein level. Considering the potent anti-HBV and anti-HCC effect, compound 5k might be a promising lead to develop novel therapeutic agents towards HBV infection and HBV-induced HCC.

Convenient One-Pot Synthesis of Sulfonyl Chlorides from Thiols Using Sulfuryl Chloride and Metal Nitrate

Park, Young Jun,Shin, Hyun Ho,Kim, Yong Hae

, p. 1483 - 1486 (1992)

Various sulfonyl chlorides were obtained in excellent yields by the reaction of alkyl and aryl thiols with sulfuryl chloride in the presence of metal nitrate under mild condition in aprotic solvents such as acetonitrile and N,N-dimethylformamide.

Keefer,Andrews

, p. 543,544, 547 (1953)

Iron-Catalyzed C-C Single-Bond Cleavage of Alcohols

Liu, Wei,Wu, Qiang,Wang, Miao,Huang, Yahao,Hu, Peng

supporting information, p. 8413 - 8418 (2021/11/01)

An iron-catalyzed deconstruction/hydrogenation reaction of alcohols through C-C bond cleavage is developed through photocatalysis, to produce ketones or aldehydes as the products. Tertiary, secondary, and primary alcohols bearing a wide range of substituents are suitable substrates. Complex natural alcohols can also perform the transformation selectively. A investigation of the mechanism reveals a procedure that involves chlorine radical improved O-H homolysis, with the assistance of 2,4,6-collidine.

Nickel catalyzed deoxygenative cross-coupling of benzyl alcohols with aryl-bromides

Kumar Chenniappan, Vinoth,Peck, Devin,Rahaim, Ronald

, (2020/03/03)

A nickel-catalyzed cross-electrophile coupling of benzyl alcohols with aromatic bromides has been developed. This deoxygenative cross-coupling occurs under mild reaction conditions at ambient temperature affording diarylmethanes, or 1,3-diarylpropenes from benzyl allyl alcohols. The system demonstrated good chemoselectivity tolerating an assortment of reactive functional groups.

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