| Identification | More | [Name]
Benzyl chloride | [CAS]
100-44-7 | [Synonyms]
A-CHLOROTOLUENE
AKOS BBS-00003953
ALPHA-CHLOROTOLUENE
BENZYL CHLORIDE
(chloromethyl)-benzen
(Chloromethyl)benzene
(chloromethyl)-Benzene
1-Chloromethylbenzene
1-Chlorome-thylbenzene
ai3-15518
alpha-chloro-toluen
alpha-Chlortoluol
alpha-tolylchloride
Benzene, (chloromethyl)-
benzene,(chloromethyl)-
benzene,chloromethyl-
Benzile
Benzile(cloruro di)
benzile(clorurodi)
Benzylchlorid | [EINECS(EC#)]
202-853-6 | [Molecular Formula]
C7H7Cl | [MDL Number]
MFCD00000889 | [Molecular Weight]
126.58 | [MOL File]
100-44-7.mol |
| Chemical Properties | Back Directory | [Appearance]
Benzyl chloride is a colorless to s lightly yellow
liquid with a strong, unpleasant, irritating odor. The
Odor Threshold is 0.05 ppm. | [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.)
| [Fp ]
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 | [Odor]
Pungent, irritating. | [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. | [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) | [Dielectric constant]
7.0（13℃） | [Exposure limits]
TLV-TWA 1 ppm (～5mg/m3) (ACGIH,
MSHA, and OSHA); IDLH 10 ppm
(NIOSH); carcinogenicity: Animal Limited
Evidence, Human Inadequate Evidence
(IARC). | [InChIKey]
KCXMKQUNVWSEMD-UHFFFAOYSA-N | [LogP]
2.3 at 20℃ and pH7 | [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]
100-44-7(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T | [Risk Statements ]
R45:May cause cancer.
R22:Harmful if swallowed.
R23:Toxic by inhalation.
R37/38:Irritating to respiratory system and skin .
R41:Risk of serious damage to eyes.
R48/22:Harmful: danger of serious damage to health by prolonged exposure if swallowed . | [Safety Statements ]
S53:Avoid exposure-obtain special instruction before use .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 1738 6.1/PG 2
| [WGK Germany ]
3
| [RTECS ]
XS8925000
| [F ]
8-19 | [Autoignition Temperature]
585 °C | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
II | [HS Code ]
29039900 | [Hazardous Substances Data]
100-44-7(Hazardous Substances Data) | [Toxicity]
LD50 orally in Rabbit: 440 mg/kg | [IDLA]
10 ppm |
| Hazard Information | Back Directory | [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. | [Reactivity Profile]
Halogenated aliphatic compounds, such as BENZYL CHLORIDE(100-44-7), 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. | [Air & Water Reactions]
A lachrymator. Slightly soluble in water. | [Hazard]
Highly toxic, intense eye and skin irritant. A
lachrymator. Upper respiratory tract irritant. Prob-
able carcinogen.
| [Health Hazard]
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. | [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 plastics,
dyes, 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. | [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. | [First aid]
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately
with soap and water. Seek medical attention immediately.
If this chemical has been inhaled, remove from exposure,
begin rescue breathing (using universal precautions, including
resuscitation mask) if breathing has stopped and CPR if
heart action has stopped. Transfer promptly to a medical
facility. When this chemical has been swallowed, get medical
attention. If victim is conscious, administer water or
milk. Do not induce vomiting. Medical observation is
recommended for 24 to 48 hours after breathing overexposure,
as pulmonary edema may be delayed. As first aid for
pulmonary edema, a doctor or authorized paramedic may
consider administering a drug or other inhalation therapy. | [Shipping]
UN1738 Benzyl chloride, Hazard class: 6.1;
Labels: 6.1—Poisonous materials, 8—Corrosive material. | [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. | [Description]
Benzyl chloride is a colorless to slight yellowliquid with a strong, unpleasant, irritating odor. The odorthreshold is 0.05 ppm. Molecular weight = 126.6;Specific gravity (H2O:1) = 1.10; Boiling point = 179.4℃;Freezing/Melting point = -43℃; Vapor pressure =1 mmHg at 20℃; Flash point = 67℃ (cc); Autoignitiontemperature = 585℃. Flammable Limits in Air:LEL =5 1.1%; UEL=14.0%.Hazard Identification(based on NFPA-704 M Rating System): Health 3,Flammability 2, Reactivity 1. Practically insoluble in water;solubility=0.05%. | [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.
| [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. | [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]
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.
| [Uses]
Benzyl chloride is used in the manufacture ofdyes, artificial resins, tanning agents, phar maceuticals, plasticizers, perfumes, lubri cants, and miscellaneous benyl compounds. | [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. | [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. | [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/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 | [Health effects]
A concentration of 16
ppm of benzyl chloride in air is reported to be
intolerable to humans within 1 min. The compound is a potent lachrymator, strongly irritating
to the eyes, nose, and throat and capable of
causing lung edema. | [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. | [Toxicology]
The acute oral toxicity (LD50) of benzyl chloride
in rats is 1231 mg/kg and in mice 1624 mg/kg. The subcutaneous LD50 (in rats) of benzyl
chloride in oil solution is 1000 mg/kg.
Exposure of rats and mice to benzyl chloride
concentrations of 100 –1000 mg/m3 for 2 h
caused irritation of the mucous membranes and
conjunctivitis, vol. 11. Benzyl chloride is a
strong skin-sensitizing agent for guinea pigs . Benzyl chloride acts weakly mutagenic
in validated test systems.
Subcutaneous injection of weekly doses of 80
mg/kg for 1 year followed by a post-observation
period resulted in local sarcomas with lung
metastases in rats. The mean induction time was
500 d. After dermal application of benzyl
chloride, skin carcinomas were observed in mice. | [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). | [storage]
Color Code—Blue: Health Hazard/Poison: Storein a secure poison location. This material should be storedin tightly closed containers in a cool, well-ventilated areaaway from sunlight, heat, moisture, active metals, oxidizers.Metal containers involving the transfer of this chemicalshould be grounded and bonded. Where possible, automatically pump liquid from drums or other storage containers toprocess containers. Drums must be equipped with selfclosing valves, pressure vacuum bungs, and flame arresters.Use only nonsparking tools and equipment, especially whenopening and closing containers of this chemical. Sources ofignition, such as smoking and open flames, are prohibitedwhere this chemical is used, handled, or stored in a mannerthat could create a potential fire or explosion hazard. A regulated, marked area should be established where this chemical is handled, used, or stored in compliance with OSHAStandard 1910.1045. | [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. |
|
|