ChemicalBook > Product Catalog > Organic Chemistry > Hydrocarbons and derivatives > Hydrocarbon halides > Benzyl chloride
Benzyl chloride Chemical Properties
- Melting point:-39 °C
- Boiling point:179 °C
- Density 1.1 g/mL at 25 °C(lit.)
- vapor density 4.36 (vs air)
- vapor pressure 10.3 mm Hg ( 60 °C)
- refractive index n
- Flash point:165 °F
- storage temp. 0-6°C
- solubility soluble0.46g/L at 30°C (Decomposes in contact with water)
- form Liquid
- color Clear colorless to slightly yellow
- OdorPungent, irritating.
- explosive limit1.1-14%(V)
- Water Solubility 0.3 g/L (20 ºC)
- Merck 14,1129
- BRN 471308
- Henry's Law Constant(x 10-4 atm?m3/mol): 3.57 at 20.00 °C (inert gas stripping, Hovorka and Dohnal, 1997)
- Exposure limitsTLV-TWA 1 ppm (～5mg/m3) (ACGIH, MSHA, and OSHA); IDLH 10 ppm (NIOSH); carcinogenicity: Animal Limited Evidence, Human Inadequate Evidence (IARC).
- Stability:Unstable - inhibitors such as propylene oxide or trimethylamine are usually added to prevent polymerization. Combustible. Incompatible with strong oxidizing agents, water, acids, most common metals, dimethyl sulfoxide. Above flash point vapour-air mixtures are explosive within the limits noted above. Contact with water produces toxic fumes.
- CAS DataBase Reference100-44-7(CAS DataBase Reference)
- NIST Chemistry ReferenceBenzyl chloride(100-44-7)
- IARC2A (Vol. 29, Sup 7, 71) 1999
- EPA Substance Registry SystemBenzyl chloride (100-44-7)
- Hazard Codes T,T+
- Risk Statements 45-22-23-37/38-41-48/22-43-26-46
- Safety Statements 53-45-36/37/39-28-26-36/37
- RIDADR UN 1738 6.1/PG 2
- WGK Germany 3
- RTECS XS8925000
- F 8-19
- Autoignition Temperature585 °C
- TSCA Yes
- HazardClass 6.1
- PackingGroup II
- HS Code 29039990
- Hazardous Substances Data100-44-7(Hazardous Substances Data)
- ToxicityLD50 orally in Rabbit: 440 mg/kg
Benzyl chloride Usage And Synthesis
- Chemical PropertiesBenzyl 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 propertiesColorless 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).
- UsesBenzyl chloride is used in the manufacture ofdyes, artificial resins, tanning agents, phar maceuticals, plasticizers, perfumes, lubri cants, and miscellaneous benyl compounds.
- UsesAn intermediate in the preparation of phenylacetic acid (precursor to phamaceuticals). Also a precursor molecule to benzyl esters which are used as plasticizer, flavorants, and perfumes.
- UsesBenzyl chloride is a chemical intermediate in the manufacture of benzyl Compounds, perfumes, pharmaceutical products, dyes, plasticizers, synthetic tannins, artificial resins, and quaternary ammonium compounds.
- DefinitionChEBI: A member of the class of benzyl chlorides that is toluene substituted on the alpha-carbon with chlorine.
- Preparation2g benzyl alcohol and 6g concentrated hydrochloric acid were mixed and slowly heated. at 60°C the mixture separated into two layers. the yield of benzyl chloride was 70% of the theoretical. When the alcohol and a large excess of the acid were mixed, the reaction took place at the room temperature after a few minutes, and a theoretical yield of the chloride separated. Benzyl alcohol dissolves sparingly in hydrochloric acid of the specific gravity 1.12. when the solution is warmed, benzyl chloride is formed. Benzyl bromide and benzyl iodide were prepared in the same way from the corresponding acids.
benzyl chloride is a lachrymator, and a powerful one at that. In the presence of water, it hydrolyzes to benzyl alcohol and hydrochloric acid, so it's clear why it burns your water saturated eye so bad.
- Production MethodsBenzyl 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. 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/jo01035a504
Synthetic Communications, 16, p. 1173, 1986 DOI: 10.1080/00397918608056363
Tetrahedron Letters, 29, p. 5783, 1988 DOI: 10.1016/S0040-4039(00)82191-7
- General DescriptionA 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 ReactionsA lachrymator. Slightly soluble in water.
- Reactivity ProfileHalogenated 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.
- HazardHighly toxic, intense eye and skin irritant. A lachrymator. Upper respiratory tract irritant. Prob- able carcinogen.
- Health HazardBenzyl 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 HazardBenzyl 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.
- Chemical ReactivityReactivity with Water Undergoes slow hydrolysis, liberating hydrogen chloride (hydrochloric acid); Reactivity with Common Materials: Decomposes rapidly in the presence of all common metals (with the exception of nickel and lead), liberating heat and hydrogen chloride; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Rinse with sodium bicarbonate or lime solution; Polymerization: Polymerizes with evolution of heat and hydrogen chloride when in contact with all common metals except nickel and lead; Inhibitor of Polymerization: Triethylamine, propylene oxide or sodium carbonate.
- Potential ExposureUsed 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.
- CarcinogenicityBenzyl 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
- SourceAs 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).
- ShippingUN1738 Benzyl chloride, Hazard class: 6.1; Labels: 6.1—Poisonous materials, 8—Corrosive material.
- Purification MethodsDry 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.
- IncompatibilitiesMay 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 DisposalIncineration @ 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.
Benzyl chloride Preparation Products And Raw materials
- Preparation ProductsMeclozinesoftener DOD6-BENZYLAMINOPURINE4-(Acetamidomethyl)benzenesulfonylchloride Benzyltrimethylammonium chlorideN-Benzyl-N-ethylanilineN-Benzylcinchonidinium chlorideAMMONIUM O,O-DIISOPROPYLTHIOPHOSPHATEBenzyl salicylatesodium dibenzyl amine enzene sulfonateBenzyl cinnamateBenzyl propionate4-BENZYLOXY-2-NITROTOLUENEBenzyl ether4-METHYL-1-PHENYL-2-PENTANOL2,3-DIPHENYLPROPIONIC ACIDETHYL 5-BENZYLOXYINDOLE-2-CARBOXYLATEleucotrope OFast Scarlet Base LGBenzyl butyrate1-Benzyl-3-hydroxy-1H-indazolesoftener BCH2-Benzyl-2-thiopseudourea hydrochlorideTetradecyldimethylbenzylammonium chloride3-BenzyloxyphenolButyl benzyl phthalatepesticide emulsifier BCHS-Benzyl-L-cysteine4-Benzylpyridineazelaic acid, compound with morpholine 1-Benzyloxy-2-methoxy-4-propenylbenzene DIBENZYL PHTHALATEAlkyldimethylbenzylammonium chloride1,2-DiphenylethaneDibenzyl disulfideN-BENZYLANTHRANILIC ACIDStearyldimethylbenzylammonium chloridebenzyltrimeehyl ammonium chlorideLevelling agent S4-(phenylmethoxy)azobenzene
- Raw materialsZinc chloride2,6-DICHLOROTOLUENE
- N-OCTYLPYRIDINIUM CHLORIDE methyl3-((3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin -4-yl)amino)piperidin-1-yl)-3-oxopropanoate 3-ACETAMIDO-4-PICOLINE Tofacitinib Impurity 191 3-METHOXYCARBONYLAMINO-4-METHYLPYRIDINE 4-chloro-5H-pyrrolo[2,3-d]pyrimidin-6(7H)-one 7H-Pyrrolo[2,3-d]pyriMidin-4-aMine, N-Methyl-N-[(3R,4R)-4-Methyl-1-(phenylMethyl)-3-piperidinyl]- Methyl (1-benzyl-4-Methylpiperidin-3-yl)carbaMate Tofacitinib Impurity 20 3-bis(4-Methylbenzoyloxy)succinate) N-((3S,4S)-1-benzyl-4-Methylpiperidin-3-yl)-N-Methyl-7H-pyrrolo[2,3-d]pyriMidin-4-aMine benzyl-N,4-diMethylpiperidin-3-aMine dihydrochloride(dr>98/2) 3-Piperidinamine,4-methyl-1-(phenylmethyl)-,(3R,4R)-rel- 2,4-DICHLORO-7H-PYRROLO2,3-DPYRIMIDINE Tofacitinib Impurity 77 4-METHYL-3-METHYLAMINOPYRIDINE N-Methylbenzylamine (-)-Di-p-toluoyl-L-tartaric acid
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