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Cas Database

100-44-7

100-44-7

Identification

  • Product Name:Benzyl chloride

  • CAS Number: 100-44-7

  • EINECS:202-853-6

  • Molecular Weight:126.586

  • Molecular Formula: C7H7Cl

  • HS Code:29039990

  • Mol File:100-44-7.mol

Synonyms:Tolyl chloride;.omega.-Chlorotoluene;.alpha.-Chlortoluol;Benzyle (chlorure de) [French];NCI-C06360;Chlorure de benzyle [French];Benzylchloride;Benzylchlorid;(Chloromethyl)benzene;Toluene, .alpha.-chloro-;alpha-Chlortoluol [German];Benzyl chloride [UN1738] [Poison];Chlorophenylmethane;Benzene,(chloromethyl)-;RCRA waste number P028;Toluene, alpha-chloro-;alpha-Chlorotoluene;RCRA waste no. P028;.alpha.-Chlorotoluene;Benzylchlorid [German];Benzyl chloride, unstabilized [UN1738] [Poison, Corrosive];Chlorure de benzyle;Benzile (cloruro di) [Italian];Benzene, (chloromethyl)-;Benzoyl Chloride, Reagent;α-chlorotoluene;

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Safety information and MSDS view more

  • Pictogram(s):ToxicT

  • Hazard Codes:T,T+

  • Signal Word:Danger

  • Hazard Statement:H302 Harmful if swallowedH315 Causes skin irritation H318 Causes serious eye damage H331 Toxic if inhaled H335 May cause respiratory irritation H350 May cause cancer

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Half-upright position. Refer for medical attention. In case of skin contact Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention . In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rinse mouth. Refer for medical attention . Intensely irritating to skin, eyes, and mucous membranes. Highly toxic; may cause death or permanent injury after very short exposure to small quantities. Has been listed as a direct-acting or primary carcinogen. Large doses cause central nervous system depression. (EPA, 1998) Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Aromatic hydrocarbons and related compounds/

  • Fire-fighting measures: Suitable extinguishing media Use water spray, dry chemical, foam, or carbon dioxide. Use water to keep fire-exposed containers cool. Approach fire from upwind to avoid hazardous vapors and toxic decomposition products. It burns but does not ignite readily. It may ignite combustibles. When heated to decomposition, it 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. (EPA, 1998) Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in covered non-metallic containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Environmental considerations: Air spill: Apply water spray or mist to knock down vapors. Vapor knockdown water is corrosive or toxic and should be diked for containment.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Separated from food and feedstuffs and incompatible materials. See Chemical Dangers. Dry. Ventilation along the floor. Store only if stabilized.Separated from food and feedstuffs and incompatible materials . Ventilation along the floor. Store only if stabilized.

  • Exposure controls/personal protection:Occupational Exposure limit valuesRecommended Exposure Limit: 15 Minute Ceiling value: 1 ppm (5 mg/cu m).Biological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:TCI Chemical
  • Product Description:Benzyl Chloride (stabilized with epsilon-Caprolactam) >99.0%(GC)
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Benzyl Chloride (stabilized with epsilon-Caprolactam) >99.0%(GC)
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Benzyl chloride for synthesis. CAS No. 100-44-7, EC Number 202-853-6., for synthesis
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  • Product Description:Benzyl chloride Msynth plus. CAS No. 100-44-7, EC Number 202-853-6., Msynth plus
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:Benzyl chloride ReagentPlus , 99%, contains ≤1% propylene oxide as stabilizer
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  • Manufacture/Brand:Sigma-Aldrich
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  • Manufacture/Brand:Sigma-Aldrich
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Relevant articles and documentsAll total 384 Articles be found

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.

An experimental and theoretical study on imidazolium-based ionic liquid promoted chloromethylation of aromatic hydrocarbons

Wang, Yun,Xi, Yanli

, p. 2196 - 2199 (2013)

The chloromethylation of aromatic hydrocarbons proceeded efficiently using the reusable imidazolium-based ionic liquid as promoter. Mild reaction conditions, enhanced rates, improved yields, recyclability of ionic liquids, and reagents' reactivity which is different from that in conventional organic solvents are the remarkable features observed in ionic liquids. The ionic liquids were recycled in three subsequent runs with no decrease in activity. In addition, the results of calculations with the Gaussian 98 suite of program are in good accordance with the experimental outcomes.

Formation of Benzylic Chlorides by Rearrangement of Cycloheptatrienes with Tellurium Tetrachloride

Albeck, Michael,Tamari, Tova,Sprecher, Milon

, p. 2276 - 2278 (1983)

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Trichloroisocynuric acid/DMF as efficient reagent for chlorodehydration of alcohols under conventional and ultrasonic conditions

Venkana, Purugula,Kumar, Mukka Satish,Rajanna, Kamatala Chinna,Ali, Mir Moazzam

, p. 97 - 103 (2015)

A new and efficient method for the chlorodehydration of alcohols utilizing TCCA/DMF is described. Various alcohols can be converted smoothly into their corresponding alkyl chlorides in high yields under mild conditions with short reaction times. Taylor & Francis Group, LLC.

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.

Chloroalkylation of aryl aldehydes using alkylboron dichlorides in the presence of oxygen

Kabalka, George W,Wu, Zhongzhi,Ju, Yuhong

, p. 6239 - 6241 (2001)

Reactions of aryl aldehydes with alkylboron dichlorides in the presence of oxygen at room temperature produces arylalkyl chlorides in good to excellent yields.

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)

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Huyser

, p. 5246 (1960)

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Walling,Jacknow

, p. 6108 (1960)

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Reactivity of [WCl6] with Ethers: A Joint Computational, Spectroscopic and Crystallographic Study

Bortoluzzi, Marco,Marchetti, Fabio,Pampaloni, Guido,Zacchini, Stefano

, p. 3169 - 3177 (2016)

The reactions of [WCl6] with a series of ethers have been performed in chlorinated solvent and elucidated by means of analytical, spectroscopic and DFT methods. The addition of tetrahydropyran (thp) or 1,4-dioxane to [WCl6] resulted in the reversible formation of the adducts WCl6···L [L = thp (1a), 1,4-dioxane (1b)], detected in solution by NMR spectroscopy. The reaction of [WCl6] with thp in a molar ratio of 1:2 in chloroform at reflux afforded [WOCl4(thp)] (2a), which was isolated in 51 % yield. [WOCl4(OMe2)] (2b) and [WOCl3(OMe2)2] (3a) were isolated in yields of 53 and 18 %, respectively, from the reaction of [WCl6] with an excess of dimethyl ether. [WOCl3(OEt2)2] (3b) was the only identified metal compound produced from the reaction of [WCl6] and OEt2(1:2 molar ratio). According to NMR studies, the oxide ligand in 2a,b and 3a,b was generated by double C–O bond cleavage involving one equivalent of organic reactant. The 1:1 reaction of [WCl6] with 1,2-diethoxyethane led to [WCl5(κ1-OCH2CH2OEt)] (4) and a minor amount of [WCl4(κ2-EtOCH2CH2OEt)] (5). The aryl oxide compound [WCl5(OPh)] (6) was prepared in 62 % yield from the reaction of [WCl6] and anisole by selective Csp3–O bond activation. The prolonged heating of a mixture of [WCl6] and diphenyl ether in 1,2-dichloroethane led to the isolation of the WVcomplex [WCl5(OPh2)] (7). The molecular structures of 2a and 3a were ascertained by X-ray diffraction.

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Johnson,Douglass

, p. 2548 (1939)

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Chlorination of aromatic compounds with chlorous acid under non-aqueous conditions

Muathen, Hussni A.

, p. 1493 - 1497 (1999)

The non-aqueous solution of chlorous acid is a versatile chlorinating agent for aromatic compounds, e.g. alkylbenzenes, anisoles, and acetanililides. It is also an effective chlorine-substitute for the conversion of aryl bromides into aryl chlorides under mild conditions. The stoichiometry of the chlorination reaction is ArH+3HOClO→ArCl+2ClO2+2H2O, and the mode of dissociation of chlorous acid in dichloromethanc is 3HOClO→HOCl+2ClO2+H2O.

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.

The Hexachlorocerate(III) Anion: A Potent, Benchtop Stable, and Readily Available Ultraviolet A Photosensitizer for Aryl Chlorides

Yin, Haolin,Jin, Yi,Hertzog, Jerald E.,Mullane, Kimberly C.,Carroll, Patrick J.,Manor, Brian C.,Anna, Jessica M.,Schelter, Eric J.

, p. 16266 - 16273 (2016)

The hexachlorocerate(III) anion, [CeIIICl6]3-, was found to be a potent photoreductant in acetonitrile solution with an estimated excited-state reduction potential of - 3.45 V versus Cp2Fe0/+. Despite a short lifetime of 22.1(1) ns, the anion exhibited a photoluminescence quantum yield of 0.61(4) and fast quenching kinetics toward organohalogens allowing for its application in the photocatalytic reduction of aryl chloride substrates.

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Downie,Lee

, p. 4951 (1968)

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The selective functionalization of saturated hydrocarbons. Part 47, investigation of the size of the reagent involved in the Fe(II)-Fe(IV) manifold

Barton, Derek H.R.,Launay, Franck

, p. 12699 - 12706 (1998)

Competition experiments between cyclohexane and various aromatic substrates have been carried out in pyridine-acetonitrile in order to ascertain the steric requirements of the Fe(II)-H2O2 reagent in comparison with the Fe(III)-H2O2 reagent already studied. The latter is distinctly larger and much less reactive than the former. Although these results might indicate that the Fe(II)H2O2 reagent is simply the hydroxyl radical, the chemistry observed is strictly dependent on the presence of picolinic acid. Without the latter, no significant oxidation of any substrate is observed. Hydroxyl radical formation (Fenton Chemistry) is not considered to be ligand dependent in preceding investigations.

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.

-

Schreyer

, p. 3483 (1958)

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

, p. 962 - 963 (1972)

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Phase Transfer Catalysts Based on Sucrose Ethyleneoxide Adducts

Gruber, Heinrich,Greber, Gerd

, p. 1063 - 1076 (1981)

Sucrose ethyleneoxide adducts have been prepared by reaction of sucrose with various amounts of ethyleneoxide in DMSO.The resulting polypode molecules were found to be efficient phase transfer catalysts in nucleophilic substitutions, oxidation and dichlorcarbene generation.Polymerisable polypodes have been obtained by reaction of sucrose ethyleneoxide adducts with methacrylic anhydride or methacryloylchloride in pyridine.Free radical polymerisation of the resulting mixtures of mono- and polyfunctional methacrylic esters of sucrose ethyleneoxide adducts yielded crosslinked gels.These polymer-supported "octopus-molecules" were found to be efficient triphase catalysts. - Keywords: Polypode ligand as phase transfer catalyst; Polypode ligand, polymer supported

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.

Kinetics of the gas-phase elimination reaction of benzyl chloroformate and neopentyl chloroformate

Lezama, Jesus,Domnguez, Rosa M.,Chuchani, Gabriel

, p. 104 - 112 (2015)

The gas-phase eliminations of benzyl chloroformate (475-523 K, 31-103 Torr) and neopentyl chloroformate (563-622 K, 37-70 Torr), in a deactivated static reaction vessel, and in the presence of a free radical suppressor, are homogeneous, unimolecular, and follow a first-order rate law. The rate coefficients are expressed by the following Arrhenius equations: Benzyl chloroformate log κI = (13.30 ± 0.38) - (152.9 ± 3.6) kJ mol-1(2.303RT)-1; r = 0.9989 Neopentyl chloroformate Formation of neopentyl chloride: log κI = (14.29 ± 0.48) - (196.3 ± 5.5) kJ mol-1(2.303RT)-1; r = 0.9986 Formation of 2-methylbutenes: log κII = (12.12 ± 0.73) - (178.2 ± 8.3) kJ mol-1(2.303RT)-1; r = 0.9960 The derived kinetic and thermodynamic parameters for benzyl chloroformate decomposition indicate the reaction proceeds through a concerted four-membered cyclic transition state to give benzyl chloride and CO2 gas. Neopentyl chloroformate undergoes a parallel reaction, where neopentyl chloride formation may arise from a polar-concerted four-membered cyclic transition state, whereas the mixture of olefins, 2-methyl-2-butene, and 2-methyl-1-butene appears to be produced from a carbene intermediate. This intermediate seems to be originated from a concerted five-membered cyclic transition state of the neopentyl substrate.

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Brocklehurst et al.

, p. 2017 (1964)

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Selective Cross Coupling via Oxovanadium(V)-Induced Oxidative Desilylation of Benzylic Silanes

Hirao, Toshikazu,Fujii, Takashi,Ohshiro, Yoshiki

, p. 8005 - 8008 (1994)

Benzylic silanes bearing an electron-donating group at the ortho- or para-position underwent the oxovanadium(V)-induced one-electron oxidative desilylation due to low ionization potential, which was applied to the intermolecular regioselective coupling with allylic silanes or silyl enol ether.

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.

Medium and Structure Effects on the Anodic Oxidation of Aryl Arylmethyl Sulfides

Baciocchi, Enrico,Rol, Cesare,Scamosci, Emanuela,Sebastiani, Giovanni V.

, p. 5498 - 5502 (1991)

The anodic oxidation of a number of XC6H4CH2SC6H4Y has been investigated under a variety of conditions (AcOH/AcO(1-), AcOH/NO3(1-), AcOH/ClO4(1-), CH3CN/ClO4(1-) and the relative weight of the various reaction paths available to the intermediate radical cation (Cα-H deprotonation, C-S bond cleavage, attack on sulfur) evaluated via product analysis.It has been observed that in AcOH/AcO(1-) (presence of a strong base) the main reaction is Cα-H deprotonation, which is also favored when X is an electron-withdrawing substituent and depressed by electron-donating Y.The C-S bond cleavage reaction is particularly important in CH3CN/ClO4(1- ); its relative contribution is enhanced by an electron-donating X, which makes the benzyl carbocation more stable.The pathway leading to sulfoxides is favored in AcOH/NO3(1-) and, to a lesser extent, in AcOH/ClO4(1-).Formation of sulfoxide is also favored when Y is an electron-donating group.

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

-

Bancroft,Whearty

, p. 183,184 (1931)

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Halford,Reid

, p. 1873,1876 (1941)

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Astonishing alkylation and unusual reduction reactions of anionic titanium(II) isopropoxide complexes: Evidence for SET processes in transition-metal oxidative additions

Eisch, John J.,Gitua, John N.

, p. 3091 - 3096 (2002)

A mixture of titanium(II) isopropoxide and lithium isopropoxide (1:2), generated in THF by the treatment of titanium(IV) isopropoxide with two equivalents of n-butyllithium, has been shown to be an unexpected alkylating agent as well as an unusual reducing agent for a wide variety of organic substrates. Since titanium(II) isopropoxide, which is free of any lithium isopropoxide, neither causes alkylation of any of the same substrates nor is such a powerful reductant, it is proposed that the lithium isopropoxide activates titanium(II) isopropoxide for such unusual reactions by the formation of the lithium salt coordination complex Li2Ti[OiPr]4. Illustrative of the unprecedented alkylations are the transformations, after hydrolysis, of various substituted benzonitriles to isopropyl-substituted phenyl ketones, of (dichloromethyl)benzene to, principally, 2-methyl-1-phenyl-1-propene and of (trichloromethyl)benzene to isopropyl phenyl ketone. By comparing the reducing actions of Li2Ti[OiPr]4 and Ti[OiPr]2 individually, it has been shown that, generally, the lithium salt is the more powerful reductant for epoxides, benzylic halides and conjugated olefins. From the reactions of Li2Ti[OiPr]4 with the benzonitriles, styrene, the isomeric stilbene oxides and cis-stilbene, cogent evidence is marshaled for the operation of SET processes, sensitive to steric hindrance, in such alkylations and reductions. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Elliott,Speakman

, p. 641,647,649 (1940)

Competing reactions of secondary alcohols with sodium hypochlorite promoted by phase-transfer catalysis

Bright, Zack R.,Luyeye, Cedric R.,Morton, Angela Ste. Marie,Sedenko, Marina,Landolt, Robert G.,Bronzi, Matthew J.,Bohovic, Katherine M.,Gonser, M. W. Alex,Lapainis, Theodore E.,Hendrickson, William H.

, p. 684 - 687 (2005)

(Chemical Equation Presented) With aqueous hypochlorite and a phase transfer catalyst, secondary alcohols undergo hitherto unreported free radical reactions that compete with and effectively limit traditional ketone syntheses. Product mixture profiles are determined by reactant ratios, organic cosolvent, and availability of oxygen to the system. Under argon, over half of substrate alcohols, PhCH(OH)R, are converted to benzaldehyde and free radical products through β-scission of intermediate alkyl hypochlorites. Secondary alcohols with R containing three or more carbons also may undergo δ chlorination.

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Gruselle,Nedelec

, p. 1813,1814 (1978)

-

-

Knowles,Norman

, p. 2938 (1961)

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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.

NICKEL(SALEN) CATALYSED CHLORINATION OF SATURATED HYDROCARBONS BY SODIUM HYPOCHLORITE

Querci, Cecilia,Strogolo, Sauro,Ricci, Marco

, p. 6577 - 6580 (1990)

In the presence of nickel(salen) as the catalyst, basic (pH 11) aqueous solutions of sodium hypochlorite chlorinate saturated hydrocarbons under very mild conditions.

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)

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-

Silberrad,O.,Silberrad,C. A.,Parke

, p. 1724 (1925)

-

-

Kwart et al.

, p. 765 (1967)

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-

Firth,Smith

, p. 337,339 (1936)

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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

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Rees,Storr

, p. 1474 (1969)

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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.

Silica Chloride (SiO2-Cl), a New Heterogeneous Reagent, for the Selective and Efficient Conversion of Benzylic Alcohols to Their Corresponding Chlorides and Iodides

Firouzabadi, Habib,Iranpoor, Naser,Karimi, Babak,Hazarkhani, Hassan

, p. 3671 - 3677 (2003)

Structurally different benzylic alcohols were efficiently converted to their corresponding chlorides by silica chloride (SiO2-Cl) in CHCl3 at room temperature. Silica chloride is also able to convert benzylic alcohols to their iodides in the presence of NaI in a mixture of CH3CN/CHCl3 in excellent yields.

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.

Catalytic dehydrative etherification and chlorination of benzyl alcohols in ionic liquids

Kalviri, Hassan A.,Petten, Chad F.,Kerton, Francesca M.

, p. 5171 - 5173 (2009)

Dibenzyl ethers and benzyl chloride can be obtained in moderate to excellent yields through Pd-catalysed reactions in hydrophobic ionic liquids using microwave or conventional heating. The Royal Society of Chemistry 2009.

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.

A Kinetic and Mechanistic Study of the Self-Reaction and Reaction with H2O of the Benzylperoxy Radical

Noziere, Barbara,Lesclaux, Robert,Hurley, Michael D.,Dearth, Mark A.,Wallington, Timothy J.

, p. 2864 - 2873 (1994)

The kinetics and mechanism of the reactions C6H5CH2O2 + C6H5CH2O2 -> 2C6H5CH2O + O2 (3a), C6H5CH2O2 + C6H5CH2O2 -> C6H5CHO + C6H5CH2OH + O2 (3b), and C6H5CH2O2 + HO2 -> C6H5CH2OOH + O2 (4) have been investigated using two complementary techniques: flash photolysis/UV absorption for kinetic measurements and continuous photolysis/FTIR spectroscopy for end-product analyses and branching ratio determinations.The reaction of chlorine atoms with toluene was found to yield benzyl radicals exclusively and was used to generate benzylperoxy radicals in excess oxygen.During this study, relative reaction rate constants of chlorine atoms with compounds related to those involved in the reaction mechanism have been measured at room temperature: k(Cl+toluene) = (6.1 +/- 0.2)E-11, k(Cl+benzaldehyde) = (9.6 +/- 0.4)E-11, k(Cl+benzyl chloride) = (9.7 +/- 0.6)E-12, k(Cl+benzyl alcohol) = (9.3 +/- 0.5)E-11, k(Cl+benzene) 3 molecule-1 s-1.The products identified following the self-reaction 3 were benzaldehyde, benzyl alcohol, and benzyl hydroperoxide.The latter is the product of the reaction of C6H5CH2O2 with HO2.The yield of products allowed us to determine the branching ratio α = k3a/k3 = 0.4.The UV absorption spectrum of the benzylperoxy radical was determined from 220 to 300 nm.It was similar to those of alkylperoxy radicals, with a maximum cross section at 245 nm of 6.8E-18 cm2 molecule-1.Kinetic data were obtained from the detailed simulation of experimental decay traces recorded at 250 nm over the temperature range 273-450 K.The resulting rate expression are k3 = (2.75 +/- 0.15)E-14 exp cm3 molecule-1 a-1 and k4 = (3.75 +/- 0.32)E-13 exp3 molecule-1 s-1 (errors = 1?).The UV absorption traces in the flash-photolysis kinetic study were well accounted for by the identified products in the FTIR study, thus providing good confidence in the results.However, about 20percent of the products have remained unidentified.Some uncertainties persist in the reaction mechanism leading us to assign a fairly large uncertainty of about 50percent to the rate constants k3 and k4 over the whole temperature range.This work shows that the aromatic substituent does not provide any specificity in the reactivity of peroxy radicals and confirms that large radicals tend to react faster with HO2 than generally assumed in current atmospheric models.

Keefer,Andrews

, p. 543,544, 547 (1953)

Kochi,Davis

, p. 5264,5266 (1964)

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.

One-Pot Synthesis of Thiocarbamates

Barther, Dennis,Malliaridou, Triantafillia,Meier, Michael A. R.,Moatsou, Dafni,Waibel, Kevin A.

supporting information, p. 4508 - 4516 (2021/08/30)

An efficient isocyanide-based synthesis of S-thiocarbamates was discovered and thoroughly investigated. The new reaction protocol is a one-pot procedure and allows the direct conversion of N-formamides into thiocarbamates by initial dehydration with p-toluene sulfonyl chloride to the respective isocyanide and subsequent addition of a sulfoxide component. Contrary to recent literature, which also uses isocyanides as starting material, but with other sulfur reagents than sulfoxides, in this protocol, no isolation and purification of the isocyanide component is necessary, thus significantly decreasing the environmental impact and increasing the efficiency of the synthesis. The new protocol was applied to synthesize a library of sixteen thiocarbamates, applying four N-formamides and four commercially available sulfoxides. Furthermore, experiments were conducted to investigate the reaction mechanism. Finally, four norbornene-based thiocarbamate monomers were prepared and applied in controlled ring-opening metathesis polymerization (ROMP) reactions. The polymers were characterized by size-exclusion chromatography (SEC) and their properties were investigated utilizing differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA).

Visible Light-Catalyzed Benzylic C-H Bond Chlorination by a Combination of Organic Dye (Acr+-Mes) and N-Chlorosuccinimide

Xiang, Ming,Zhou, Chao,Yang, Xiu-Long,Chen, Bin,Tung, Chen-Ho,Wu, Li-Zhu

, p. 9080 - 9087 (2020/08/14)

By combining "N-chlorosuccinimide (NCS)"as the safe chlorine source with "Acr+-Mes"as the photocatalyst, we successfully achieved benzylic C-H bond chlorination under visible light irradiation. Furthermore, benzylic chlorides could be converted to benzylic ethers smoothly in a one-pot manner by adding sodium methoxide. This mild and scalable chlorination method worked effectively for diverse toluene derivatives, especially for electron-deficient substrates. Careful mechanistic studies supported that NCS provided a hydrogen abstractor "N-centered succinimidyl radical,"which was responsible for the cleavage of the benzylic C-H bond, relying on the reducing ability of Acr?-Mes.

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.

Process route upstream and downstream products

Process route

(benzyloxy)trichlorosilane
18141-27-0

(benzyloxy)trichlorosilane

tetrachlorosilane
10026-04-7,53609-55-5

tetrachlorosilane

stilbene
588-59-0

stilbene

hexachlorodisiloxane
14986-21-1

hexachlorodisiloxane

pentachlorodisiloxane
56240-62-1

pentachlorodisiloxane

benzyl chloride
100-44-7

benzyl chloride

Conditions
Conditions Yield
With trichlorosilane; at 480 ℃; for 0.00833333h; Product distribution; Mechanism; other amount of HSiCl3, other temperature;
1-Phenylethanol
98-85-1,13323-81-4

1-Phenylethanol

tert-butylamine hydrochloride
10017-37-5

tert-butylamine hydrochloride

benzyl chloride
100-44-7

benzyl chloride

acetophenone
98-86-2

acetophenone

Conditions
Conditions Yield
With N,N-dichloro-t-butylamine; at 20 ℃; for 1h; Irradiation;
51%
benzenesulfonyl chloride
1939-99-7

benzenesulfonyl chloride

benzyl bromide
100-39-0

benzyl bromide

benzyl chloride
100-44-7

benzyl chloride

Conditions
Conditions Yield
With lithium bromide; Mechanism;
phosphorus pentachloride
10026-13-8,874483-75-7

phosphorus pentachloride

phenyl-methanesulfonic acid ; potassium salt

phenyl-methanesulfonic acid ; potassium salt

thionyl chloride
7719-09-7

thionyl chloride

benzyl chloride
100-44-7

benzyl chloride

Conditions
Conditions Yield
tert-butylammonium methyl N-(benzyloxycarbonyl)-N-methyl-1-amino-1-methylethylphosphonate

tert-butylammonium methyl N-(benzyloxycarbonyl)-N-methyl-1-amino-1-methylethylphosphonate

tert-butylamine hydrochloride
10017-37-5

tert-butylamine hydrochloride

benzyl chloride
100-44-7

benzyl chloride

2-methoxy-3,3,4-trimethyl-2-oxo-2λ<sup>5</sup>-[1,4,2]oxazaphospholidin-5-one

2-methoxy-3,3,4-trimethyl-2-oxo-2λ5-[1,4,2]oxazaphospholidin-5-one

Conditions
Conditions Yield
With thionyl chloride; In chloroform-d1;
benzyl bromide
100-39-0

benzyl bromide

benzyl chloride
100-44-7

benzyl chloride

Conditions
Conditions Yield
With tetrabutylammomium bromide; hydrogen bromide; potassium bromide; In water; at 20 ℃; Irradiation; Green chemistry;
90%
With N-hydroxyphthalimide; carbon tetrabromide; trichloroisocyanuric acid; cobalt(II) diacetate tetrahydrate; In dichloromethane; at 25 ℃; for 20h;
benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

Benzyl acetate
140-11-4

Benzyl acetate

benzyl chloride
100-44-7

benzyl chloride

Conditions
Conditions Yield
With chloro-trimethyl-silane; acetic acid; at 60 ℃; for 9h; Concentration;
acrylic acid n-butyl ester
141-32-2,9003-49-0

acrylic acid n-butyl ester

benzyl bromide
100-39-0

benzyl bromide

n-butyl 2-bromo-4-phenyl-n-butyrate

n-butyl 2-bromo-4-phenyl-n-butyrate

benzyl chloride
100-44-7

benzyl chloride

n-butyl 4-phenylbutanoate

n-butyl 4-phenylbutanoate

Conditions
Conditions Yield
With chlorinated reagents;
1-phenylmethyl-4-piperidone
3612-20-2

1-phenylmethyl-4-piperidone

benzyl chloride
100-44-7

benzyl chloride

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1.1: sodium t-butanolate / toluene / 2 h
1.2: 4 h / 20 - 30 °C
2.1: sodium carbonate / toluene / 6 h / 55 - 60 °C
With sodium carbonate; sodium t-butanolate; In toluene; 1.1: |Wittig Olefination / 1.2: |Wittig Olefination;
chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

N-benzyl-4-methylenepiperidine
109105-86-4

N-benzyl-4-methylenepiperidine

benzyl chloride
100-44-7

benzyl chloride

ethyl 4-methylenepiperidine-1-carboxylate
144282-55-3

ethyl 4-methylenepiperidine-1-carboxylate

Conditions
Conditions Yield
With sodium carbonate; In toluene; at 55 - 60 ℃; for 6h; Temperature; Time;

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