Benzoic trichloride

Synonyms Benzenyl chloride benzoic trichloride benzylidyne chloride benzyl trichloride phenylchloroform toluene trichloride trichlorotoluene (trichloromethyl)-... 

Benzidine Benzoic trichloride (Benzotrichloride) Benzoyl chloride Benzoyl peroxide Benzyl chloride Beryllium Biphenyl... 

SYNS BENZENYL CHLORIDE BENZENYL TRICHLORIDE BENZOIC TRICHLORIDE BENZOTRICHLORIDE pOT, MAK) BENZYLIDYNE CHLORIDE CHLORURE de BENZENYLE (FRENCH) PHENYL CHLOROFORM PHENYLTRICHLORO-METHANE RCRA WASTE NUMBER U023 ... 

BENZOIC TRICHLORIDE (98-07-7) Combustible liquid (flash point 260°F/127°C). Reacts with moist air, forming hydrogen chloride fumes. Reacts slowly with water, forming corrosive hydrochloric acid and benzoic acid. Reacts violently with amines or finely divided light metals (aluminum, magnesium, beryllium, etc.). Contact with acids evolves chlorine gas. Attacks some plastics, rubber, and coatings. Attacks metals in the presence of moisture. 

Beilstein Handbook Reference) AI3-02583 Benzene, trichloromethyl)- Benzenyl trichloride Benzoic trichloride Benzotrichloride Benzolrlcloruro Benzyl trichloride Benzylidyne chloride BRN 0508152 CCRIS 1292 Chloruie de benzenyle Chlorure de benzylidyne EINECS 202-634-5 HSDB 2076 NSC 14663 Phenyl chloroform Phenyltrichloromethane RCRA waste a,a,a,-trichloro- Toluene trichloride ... 

SYNONYMS Alpha-alpha-alpha-trichlorotoluene, benzenyl chloride, benzenyl trichloride, benzoic trichloride, phenylchloroform, phenyltrichloromethane. 

Benzoic aldehyde. See Benzaldehyde Benzoic ether. See Ethyl benzoate Benzoic trichloride. See Benzotrichloride Benzoin... 

Synonyms Benzene, (trichloromethyl)- Benzenyl chloride Benzenyl trichloride Benzoic trichloride Benzylidyne chloride Benzyl trichloride Phenylchloroform Phenyl trichloromethane Toluene trichloride Toluene,... 

Acylation. Aromatic amines react with acids, acid chlorides, anhydrides, and esters to form amides. In general, acid chlorides give the best yield of the pure product. The reaction with acetic, propionic, butanoic, or benzoic acid can be catalyzed with phosphoms oxychloride or trichloride. 

Pyridine has been phenylated with the following free-radical sources benzenediazonium chloride with aluminum trichloride the Gomberg reaction " phenylhydrazine and metal oxides A -nitroso-acetanilide dibenzoyl peroxide phenylazotriphenylmethane di-phenyliodonium hydroxide and electrolysis of benzoic acid. ° Although 2-phenylpyridine usually accounts for over 50% of the total phenylated product, each of the three phenyl derivatives can be obtained from the reaction by fractional recrystallization of the... 

Another examination involves a synthesis of thienobenzazepines based on the formation of key intermediate 6 prepared according to the method of McDowell and Wisowaty (Scheme 6.2). ° Selective reduction of this intermediate using zinc dust in 28-30% ammonia solution afforded the benzoic acid 7, which upon subsequent Curtius rearrangement and aluminum trichloride-mediated cyclization furnished the oxo-azepine 8. While this synthetic approach gave the tricycle in a few synthetic transformations, many of the same concerns as above exist when considering large scale preparation of 8 the use of large amounts of zinc, sodium azide, and aluminum trichloride. 

Methylbenzenes are oxidized to the corresponding benzoic acids in very high yield under phase-transfer catalytic conditions by sodium hypochlorite in the presence of ruthenium trichloride, which is initially oxidized to ruthenium tetroxide [5]. Absence of either the ruthenium or the quaternary ammonium salt totally inhibits the reaction. 

In the presence of ruthenium trichloride, alkaline sodium hypochlorite is able to oxidize methylbenzenes to benzoic acids under phase-transfer conditions at room temperature. In a recent development, selective oxidation of xylenes to toluic acids has... 

Aryltellurium trichlorides and diaryltellurium dichlorides react with nickel tetracarbonyl in DMF, giving benzoic acids. Small amounts of diaryl tellnrides and diaryl ketones are by-products of these reactions. 

The unusual oxidant nickel peroxide converts aromatic aldehydes into carboxylic acids at 30-60 °C after 1.5-3 h in 58-100% yields [934. The oxidation of aldehydes to acids by pure ruthenium tetroxide results in very low yields [940. On the contrary, potassium ruthenate, prepared in situ from ruthenium trichloride and potassium persulfate in water and used in catalytic amounts, leads to a 99% yield of m-nitrobenzoic acid at room temperature after 2 h. Another oxidant, iodosobenzene in the presence of tris(triphenylphosphine)ruthenium dichloride, converts benzaldehyde into benzoic acid in 96% yield at room temperature [785]. The same reaction with a 91% yield is accomplished by treatment of benzaldehyde with osmium tetroxide as a catalyst and cumene hydroperoxide as a reoxidant [1163]. 

The second example of an acylation during which the acid chloride is generated in situ (67BCF88) (Scheme 12) involves the reaction of 4-aminopyrazol-3-one 30 with 2-hydroxy-5-(methoxycarbonyl)benzoic acids 47a c where phosphorus trichloride is used and gives methyl 3- [(3-oxopyrazol-4-yl)amino]carbonyl -4-hydroxybenzoates 48a c. 

Hard Lewis acid chloroaluminate ionic liquids show intense catalytic activity in the Friedel-Crafts acylation reaction however, they suffer from the same issues as anhydrous aluminum chloride. i Of particular interest to these reactions, aluminum chloride may be replaced by indium trichloride to form chloroindate(III) ionic liquids. The advantage of using indium trichloride compared with aluminum chloride is represented by its hydrolytic stability and reduced oxophilicity. Chloroindate(III) ionic liquids are synthesized by mixing l-butyl-3-methylimidazolium chloride [C4mim]Cl with anhydrous indium trichloride at 80°C. In the benzoyla-tion of anisole with benzoic anhydride (BAN) at 80°C, the best yield of... 

Benzylidene chloride and its nuclear-substituted derivatives are important mainly as intermediates on the way to aldehydes, so that the difficulty of separating them from benzotri-chlorides must be overcome. On hydrolysis they give benzoic acids, which are readily separable from the aldehydes. Phosphorus trichloride (ca. 2%) has been recommended as addition for side-chain chlorination of toluenes. 

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