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Benzyl chloride

Product Name
Benzyl chloride
CAS No.
100-44-7
Chemical Name
Benzyl chloride
Synonyms
gjgjg;Bzl-Cl;Benzile;Benzyle;NSC 8043;ai3-15518;C6H5CH2Cl;NCI-C06360;Benzylchlorid;tolylchloride
CBNumber
CB1852583
Molecular Formula
C7H7Cl
Formula Weight
126.58
MOL File
100-44-7.mol
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Benzyl chloride Property

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 
n20/D 1.538(lit.)
Flash point:
165 °F
storage temp. 
Store below +30°C.
solubility 
soluble0.46g/L at 30°C (Decomposes in contact with water)
form 
Liquid
color 
Clear colorless to slightly yellow
Odor
Pungent, irritating.
explosive limit
1.1-14%(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 limits
TLV-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.
InChIKey
KCXMKQUNVWSEMD-UHFFFAOYSA-N
CAS DataBase Reference
100-44-7(CAS DataBase Reference)
IARC
2A (Vol. 29, Sup 7, 71) 1999
NIST Chemistry Reference
Benzyl chloride(100-44-7)
EPA Substance Registry System
Benzyl chloride (100-44-7)
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Safety

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
8-19
Autoignition Temperature
585 °C
TSCA 
Yes
HazardClass 
6.1
PackingGroup 
II
HS Code 
29039990
Hazardous Substances Data
100-44-7(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: 440 mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H227Combustible liquid

H301Toxic if swalloed

H302Harmful if swallowed

H314Causes severe skin burns and eye damage

H315Causes skin irritation

H317May cause an allergic skin reaction

H318Causes serious eye damage

H330Fatal if inhaled

H331Toxic if inhaled

H335May cause respiratory irritation

H340May cause genetic defects

H350May cause cancer

H370Causes damage to organs

H372Causes damage to organs through prolonged or repeated exposure

H373May cause damage to organs through prolonged or repeated exposure

H400Very toxic to aquatic life

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P284Wear respiratory protection.

P320Specific treatment is urgent (see … on this label).

P391Collect spillage. Hazardous to the aquatic environment

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P307+P311IF exposed: call a POISON CENTER or doctor/physician.

P308+P313IF exposed or concerned: Get medical advice/attention.

P405Store locked up.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.01809
Product name
Benzyl chloride
Purity
for synthesis
Packaging
100 mL
Price
$25.53
Updated
2021/03/22
Sigma-Aldrich
Product number
8.01809
Product name
Benzyl chloride
Purity
for synthesis
Packaging
1 L
Price
$31.08
Updated
2021/03/22
Sigma-Aldrich
Product number
185558
Product name
Benzyl chloride
Purity
ReagentPlus , 99%, contains ≤1% propylene oxide as stabilizer
Packaging
1kg
Price
$88.2
Updated
2021/03/22
Sigma-Aldrich
Product number
185558
Product name
Benzyl chloride
Purity
ReagentPlus , 99%, contains ≤1% propylene oxide as stabilizer
Packaging
2kg
Price
$101
Updated
2021/03/22
Sigma-Aldrich
Product number
8.01809
Product name
Benzyl chloride
Purity
for synthesis
Packaging
2.5 L
Price
$63.36
Updated
2021/03/22
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Benzyl chloride Chemical Properties,Usage,Production

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).

Uses

Benzyl chloride is used in the manufacture ofdyes, artificial resins, tanning agents, phar maceuticals, plasticizers, perfumes, lubri cants, and miscellaneous benyl compounds.

Uses

An 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.

Uses

Benzyl chloride is a chemical intermediate in the manufacture of benzyl Compounds, perfumes, pharmaceutical products, dyes, plasticizers, synthetic tannins, artificial resins, and quaternary ammonium compounds.

Definition

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

Preparation

2g 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 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. 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 Description

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.

Chemical Reactivity

Reactivity 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 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.

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Benzyl chloride Suppliers

Liaocheng Yuze Chemical Products Co., Ltd.
Tel
;
Email
13589473332@163.com;13589473332@163.com
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China
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Nanjing Vital Chemical Co., Ltd.
Tel
025-87193546-
Fax
025-87193546
Email
chemweiao@163.com;
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China
ProdList
9076
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60
Liaocheng Tongda Chemical Co. LTD
Fax
18963573761
Email
18963573761@163.com
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China
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58
Nantong Runfeng Petrochemical Co., Ltd
Tel
Fax
0513-55085866
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2853167121@qq.com
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China
ProdList
2835
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58
Jinan Trands Chemical Co. LTD
Tel
0531-88770911- ;0531-88770911-
Fax
0531-88770911
Email
277033665@qq.com;1343989492@qq.com
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China
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Sigma-Aldrich
Tel
021-61415566- ;
Email
orderCN@merckgroup.com;orderCN@merckgroup.com
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China
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Shandong Xuchen Chemical Technology Co. Ltd
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0533-15053312575;
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Shandong Zhenkun New Material Co., LTD
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13683127222
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277809310@qq.com;277809310@qq.com
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WUHAN JIXINYIBANG BIOTECHNOLOGY .,LTD
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J & K SCIENTIFIC LTD.
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010-82848833- ;010-82848833-
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jkinfo@jkchemical.com;market6@jkchemical.com
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View Lastest Price from Benzyl chloride manufacturers

Shanxi Lianxu New Material Co., LTD
Product
Benzyl chloride 100-44-7
Price
US $30.00/Kg/Drum
Min. Order
1Kg/Drum
Purity
99%
Supply Ability
1000kg/month
Release date
2021-10-27
Anhui Rencheng Technology Co., Ltd
Product
Benzyl chloride 100-44-7
Price
US $140.00-250.00/KG
Min. Order
0.5KG
Purity
>99%
Supply Ability
20tons
Release date
2021-05-08
Wuhan Monad Medicine Tech Co.,LTD
Product
benzyl chloride 100-44-7
Price
US $10.00/Kg/Bag
Min. Order
1Kg/Drum
Purity
99%min
Supply Ability
50000
Release date
2020-12-24

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