2-Chlorobenzaldehyde

Chemical properties

2-Chlorobenzaldehyde is a colorless to yellowish liquid with a penetrating odor. Insoluble in water, soluble in benzene, alcohol and ether. 2-Chlorobenzaldehyde is considerably more resistant to oxidation than benzaldehyde. When it is heated with sodium sulfite solution under pressure, benzaldehyde-2-sulfonic acid forms.

The Uses of 2-Chlorobenzaldehyde

2-Chlorobenzaldehyde has been used in generation of small focused library of diversely functionalized dihydropyrimidine derivatives via one-pot three-component Biginelli cyclocondensation of β-ketoesters, aldehydes and thioureas.

The Uses of 2-Chlorobenzaldehyde

2-Chlorobenzaldehyde can be used to make alcohols, acids, and dyes; used in the rubber, tanning, and paper industries; used as an intermediate for optical brighteners, agricultural chemicals, and pharmaceuticals.It can also be used to prepare triphenyl methane and related dyes, organic intermediate.

Preparation

2-Chlorobenzaldehyde is produced mainly by chlorination of 2-chlorotoluene to form 2-chlorobenzal chloride, which is then subjected to acid hydrolysis. Metal salts, such as iron(III) chloride, are used as catalysts. The hydrolysis can also be accomplished using formic acid without a catalyst.
2-Chlorobenzaldehyde can also be produced by oxidation of 2-chlorobenzyl chloride with N-oxides of tertiary amines or with dilute nitric acid.
https://pubchem.ncbi.nlm.nih.gov/compound/2-Chlorobenzaldehyde

What are the applications of Application

2-Chlorobenzaldehyde is used acid zinc plating brightener, also be used for organic synthesis, agricultural pesticide and pharmaceutical industries. It is used to synthesize the acaricides clofentezine and flutenzine. 2-Chlorobenzaldehyde undergoes alkynylation with phenylacetylene in the presence of catalytic ligands and dimethylzinc at 0°C to form binaphthyl-derived amino alcohols.

Synthesis Reference(s)

Tetrahedron Letters, 34, p. 8037, 1993 DOI: 10.1016/S0040-4039(00)61444-2

General Description

2-chlorobenzaldehyde is a clear colorless to yellowish liquid. (NTP, 1992)

Air & Water Reactions

2-Chlorobenzaldehyde is moisture and light sensitive. Slightly water soluble.

Reactivity Profile

2-Chlorobenzaldehyde reacts with iron and strong oxidizers, strong bases and strong reducing agents.

Health Hazard

Symptoms of exposure to 2-Chlorobenzaldehyde may include skin, eye and upper respiratory tract irritation. This compound may cause skin, eye and respiratory tract irritation. When heated to decomposition it emits toxic fumes.

Fire Hazard

2-Chlorobenzaldehyde is combustible.

Safety Profile

Poison by intraperitoneal and intravenous routes. When heated to decomposition it emits toxic fumes of Cl-. See also ALDEHYDES and CHLORIDES.

Purification Methods

Wash it with 10% Na2CO3 solution, then fractionally distil it in the presence of a small amount of catechol as stabiliser. [Beilstein 7 H 233, 7 IV 561.]