Exhaustive chlorination of the side-chain of toluene leads to benzotrichloride (trichloromethyl
benzene, a,a,a-trichlorotoluene, phenyl chloroform) [98-07-7]. The compound was first synthesized in 1858 by L. SCHISCHKOFF and A. ROSING,
using the reaction of PCl5 with benzoyl chloride.
Benzotrichloride is now produced on a large
scale, since it serves as an important intermediate
in the preparation of acid chlorides (benzoyl
chloride), dyes, herbicides, pesticides, and other
products.
Benzotrichloride is a colorless liquid with a
pungent odor and is irritating to the eyes and
mucous membranes. It fumes in moist air.Benzotrichloride is freely soluble in alcohol,
ether, and chloroform. It is only slightly soluble in
water (0.05 g/L at 5 ℃, 0.25 g/L at 39 ℃). The
solubility of chlorinein 100 g of benzotrichloride is 5.1 g at 30 ℃,
3.4 g at 50 ℃,
1.3 g at 100 ℃.
Benzotrichloride is a combustible, colorless to
yellow-brown, oily liquid that fumes on contact with air. It
has a penetrating odor.
α,α,α-Trichlorotoluene was used in determination of chlorinated toluenes in effluents of wastewater treatment plants and textile industries by closed loop stripping analysis.
Chemical intermediate primarily in
benzoyl chloride production; dye intermediate
Benzotrichloride is used mainly to produce benzoyl chloride, for which purpose it is either
partially hydrolyzed with water or else reacted
with benzoic acid. It is also of some significance
in the production of pesticides (through transformation into benzotrifluoride), ultraviolet stabilizers, and dyes.
In dye chemistry. In organic syntheses (source of benzenyl group).
ChEBI: (trichloromethyl)benzene is an organochlorine compound that is toluene in which all three hydrogens of the methyl group have been replaced by chlorines. It is used as an intermediate in organic synthesis and dye chemistry. It has a role as a carcinogenic agent. It is a member of benzenes, a volatile organic compound and an organochlorine compound.
Benzotrichloride appears as a clear colorless to yellowish colored liquid with a penetrating odor. Denser than water and vapors are heavier than air. May be toxic by inhalation or ingestion. Burns skin, eyes, and mucous membranes. Insoluble in water. Used to make dyes and other chemicals.
Hydrolyzes in the presence of moisture. The reaction is rather slow due to low solubility in water.
Benzotrichloride hydrolyzes in the presence of moisture. Benzotrichloride reacts with water, lime, ammonia, strong alkalis, organic amines, chlorates and acids.
Highly toxic by inhalation, fumes highly
irritant. Eye, skin, and upper respiratory tract irri-
tant. Probable carcinogen.
Toxic by inhalation; fumes are highly irritating to skin and mucous membranes. May cause death or permanent injury after very short exposure to small quantities. A suspected carcinogen.
Benzotrichloride may react violently with water. Fire may produce irritating or poisonous gases. Flammable/poisonous gases may accumulate in tanks and hopper cars. Materials may ignite combustibles (wood, paper, oil, etc.). Produces toxic and corrosive fumes when Benzotrichloride reacts with water or steam. Similar to hydrochloric acid; material will react with water or steam to produce toxic and corrosive fumes. Hydrolyzes in presence of water forming benzoic and hydrochloric acids.
The acute oral toxicity of benzotrichloride is
2180 mg/kg in male rats and 1590 mg/kg in
female rats. The inhalative LC50s are higher than
600 mg/m3 in male rats and about 500 mg/m3 in
female rats after a 4-h exposure. Benzotrichloride irritates the skin and eyes. The
compound proved to be mutagenic in bacterial test systems. Dermal application of benzotrichloride resulted in elevated tumor incidence
in mice.
Benzotrichloride is used as a chemical
and dye intermediate; extensively used in the dye industry
for the production of Malachite green, Rosamine,
Quinoline red, and Alizarin yellow A. It can also be used
to produce ethyl benzoate. Commercial grades may contain
hydrochloric acid, benzylidene chloride, or benzyl 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. If victim is conscious, administer water ormilk. Do not induce vomiting. Medical observation isrecommended for 24 48 h after breathing overexposure, aspulmonary edema may be delayed. As first aid for pulmonary edema, a doctor or authorized paramedic may consideradministering a corticosteroid spray.
Benzotrichloride is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.
(1) Color Code—White: Corrosive or ContactHazard; Store separately in a corrosion-resistant location.(2) Color Code—Blue: Health Hazard/Poison: Store in asecure poison location. Before entering confined spacewhere benzotrichloride may be present, check to make surethat an explosive concentration does not exist. Store intightly closed containers in a dark, cool, well-ventilatedarea. Metal containers involving the transfer of this chemical should be grounded and bonded. Where possible, automatically pump liquid from drums or other storagecontainers to process containers. Drums must be equippedwith self-closing valves, pressure vacuum bungs, and flamearresters. Use only nonsparking tools and equipment, especially when opening and closing containers of this chemical. Sources of ignition, such as smoking and open flames,are prohibited where this chemical is used, handled, orstored in a manner that could create a potential fire orexplosion hazard. A regulated, marked area should be established where this chemical is handled, used, or stored incompliance with OSHA Standard 1910.1045.
UN2226 Benzotrichloride, Hazard class: 8;
Labels: 8—Corrosive material.
Benzotrichloride decomposes on heating,
on contact with acids and/or water, producing toxic and
corrosive hydrogen chloride and benzoic acid. Reacts violently
with strong oxidizers, iron and other metals, alkali
and earth alkali metals; bases and organic substances, and
may cause fire and explosions. On contact with air it emits
toxic and corrosive hydrogen chloride. Attacks many
metals in presence of water. Attacks many plastics.
Incineration with flammable
solvent added in incinerator with afterburner and alkaline
scrubber.
