Benzal chloride (dichloromethylbenzene, a,adichlorotoluene, benzylidene chloride) is produced exclusively by the side-chain chlorination of toluene. It was first synthesized in 1848 by A. CAHOURS, by using the reaction of PCl5 with benzaldehyde. Almost the sole application of benzal chloride is in the production of benzaldehyde.
Benzal chloride is a combustible, fuming,
colorless, oily liquid; fumes on exposure to air. Faint, pungent
odor.
Benzal chloride is a liquid which fumes in moist
air and which has a pungent odor and a strong
irritant effect on the mucous membranes and eyes.Benzal chloride is freely soluble in alcohol,
ether, chloroform, and carbon tetrachloride, but
only slightly soluble in water (0.05 g/L at 5 ℃;
0.25 g/L at 39 ℃). The solubility of chlorine in
100 g of benzal chloride is
6.2 g at 30 ℃,
4.3 g at 50 ℃,
1.5 g at 100 ℃.
α,α-Dichlorotoluene has been useds as initiator during the atom transfer radical polymerization (ATRP) of styrene and methyl methacrylate.
manufacture of benzaldehyde, cinnamic acid.
ChEBI: Benzal chloride is a member of benzenes.
The Journal of Organic Chemistry, 15, p. 795, 1950
DOI: 10.1021/jo01150a012Tetrahedron Letters, 9, p. 4951, 1968
A colorless oily liquid with a faint aromatic odor. Insoluble in water and denser than water. Strongly irritates skin and eyes. Used to manufacture dyes.
BENZAL CHLORIDE is incompatible with strong oxidizers and strong bases. BENZAL CHLORIDE readily hydrolyzes under acid or alkaline conditions. BENZAL CHLORIDE reacts with metals (except nickel and lead). .
Strong irritant and lachrymator. Probable
carcinogen.
Acute: vapors are highly irritating to eyes. May be fatal if inhaled, swallowed, or absorbed through skin.
Fire may produce irritating or poisonous gases. Runoff from fire control water may give off poisonous gases and may cause pollution. Cylinder may explode in the heat of fire. Reacts with water to release hydrochloric acid.
Confirmed carcinogen
with experimental carcinogenic and
neoplastigenic data. Poison by inhalation.
Moderately toxic by ingestion. A strong
irritant and lachrymator. Causes central
nervous system depression. Mutation data
reported. When heated to decomposition it
emits toxic fumes of Cl-. See also
CHLORINATED HYDROCARBONS,
AROMATIC.
Benzal chloride is used almost exclusively
for the manufacture of benzaldehyde. It can also be
used to prepare cinnamic acid and benzoyl chloride.
If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.Medical observation is recommended for 24 48 h afterbreathing overexposure, as pulmonary edema may bedelayed. As first aid for pulmonary edema, a doctor orauthorized paramedic may consider administering a corticosteroid spray
Color Code—Blue: Health Hazard/Poison: Storein a secure poison location. Store in tightly closed containers in a cool, well-ventilated area away from oxidizers,strong acids, flammable materials, sources fire as this material is combustible. Sources of ignition, such as smokingand open flames, are prohibited where this chemical isused, handled, or stored in a manner that could create apotential fire or explosion hazard.
UN1886 Benzylidene chloride, Hazard class 6.1;
Label 6.1—Poisonous materials.
May form explosive mixture with air.
Reacts with water, air, or heat, forming fumes of hydrochloric
acid. Reacts (possibly violently) with acids, bases,
strong oxidizers; many metals; potassium, sodium, aluminum.
Attacks plastics and coatings.
Incineration @ 816 C,
0.5 second minimum for primary combustion; 1204 C,
1.0 second for secondary combustion; elemental chlorine
formation may be alleviated through injection of steam or
methane into the combustion process.
