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2-Chlorobenzaldehyde (o-chlorobenzaldehyde) is an organic compound with the formula ClC5H4CHO.
2-Chlorobenzaldehyde is one of three isomeric monochlorinated benzaldehyde.
3-Chlorobenzaldehyde and 4-chlorobenzaldehyde are the other isomers.
Whereas benzaldehyde is prone to autoxidation, the 2-chloro derivatives are more air-stable.
CAS Number: 89-98-5
EC Number: 201-956-3
IUPAC Name: 2-chlorobenzaldehyde
Chemical Formula: C7H5ClO
Other names: 89-98-5, O-CHLOROBENZALDEHYDE, Benzaldehyde, 2-chloro-, Benzaldehyde, o-chloro-, 2-Chlorbenzaldehyd, 2-Clorobenzaldeide, o-Chloorbenzaldehyde, USAF M-7, 2-Chloorbenzaldehyde, o-Chlorobenzenecarboxaldehyde, QHR24X1LXK, DTXSID5024764, NSC-15347, DTXCID204764, 201-956-3, Chlorobenzaldehyde, 2-chloro-benzaldehyde, MFCD00003304, BENZALDEHYDE,CHLORO-, 35913-09-8, NSC 15347, 2-chloro benzaldehyde, 2-Chlorbenzaldehyd [German], o-Chloorbenzaldehyde [Dutch], 2-Chloorbenzaldehyde [Dutch], 2-Clorobenzaldeide [Italian], CCRIS 5991, Benzaldehyde, chloro-, HSDB 2727, EINECS 201-956-3, UNII-QHR24X1LXK, AI3-04254, o-chlorobezaldehyde, 2-chlorobezaldehyde, 6-chlorobenzaldehyde, o-Chloroformylbenzene, orthochlorobenzaldehyde, 2- chlorobenzaldehyde, 2-chlorobenzenaldehyde, NSC 174140, (2-chloro)benzaldehye, ortho-chlorobenzaldehyde, (2-chloro)benzaldehyde, Amlodipine Impurity 65, (2-chloro) benzaldehyde, WLN: VHR BG, EC 201-956-3, 2-Chlorobenzaldehyde, 99%, SCHEMBL97421, SCHEMBL97422, MLS001056242, CHLOROBENZALDEHYDE, O-, SCHEMBL6738745, SCHEMBL7481553, CHEMBL1547989, SCHEMBL15067305, SCHEMBL15068124, SCHEMBL29815450, NSC15347, STR00143, Tox21_200373, SBB040228, STL146016, AKOS000119188, CS-W003973, CAS-89-98-5, NCGC00091218-01, NCGC00091218-02, NCGC00257927-01, SMR001216556, DB-303226, DS-006490, NS00009019, ST50213378, EN300-19123, D77644, 2-Chlorobenzaldehyde(Discontinued,See C4X-109565), Q2195231, 2-Chlorobenzaldehyde, purum, dist., >=98.0% (GC), F2190-0599, Z104472866, InChI=1/C7H5ClO/c8-7-4-2-1-3-6(7)5-9/h1-5
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.
2-chlorobenzaldehyde is a clear colorless to yellowish liquid.
2-Chlorobenzaldehyde undergoes alkynylation with phenylacetylene in the presence of catalytic ligands and dimethylzinc at 0°C to form binaphthyl-derived amino alcohols.
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 2-Chlorobenzaldehyde is heated with sodium sulfite solution under pressure, benzaldehyde-2-sulfonic acid forms.
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.
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.
2-Chlorobenzaldehyde is combustible
Uses
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.
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.
2-Chlorobenzaldehyde can also be used to prepare triphenyl methane and related dyes, organic intermediate.
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.
2-Chlorobenzaldehyde is used acid zinc plating brightener, also be used for organic synthesis, agricultural pesticide and pharmaceutical industries.
2-Chlorobenzaldehyde 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.
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.
