4-Chlorobenzaldehyde

4-Chlorobenzaldehyde
Identifiers
CAS Number	104-88-1 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	385858
ChEMBL	ChEMBL1474;
ChemSpider	21106019;
ECHA InfoCard	100.002.953
EC Number	203-247-4;
KEGG	C06648;
PubChem CID	7726;
UNII	E67727UP9Z;
UN number	2811
CompTox Dashboard (EPA)	DTXSID2021860 ;
	InChI InChI=1S/C7H5ClO/c8-7-3-1-6(5-9)2-4-7/h1-5H Key: AVPYQKSLYISFPO-UHFFFAOYSA-N;
	SMILES C1=CC(=CC=C1C=O)Cl;
Properties
Chemical formula	C7H5ClO
Molar mass	140.57 g·mol−1
Melting point	47.5 °C (117.5 °F; 320.6 K)
Boiling point	213.5 °C (416.3 °F; 486.6 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H315, H317, H319, H411
Precautionary statements	P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P333+P313, P337+P317, P362+P364, P391, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

4-Chlorobenzaldehyde (o-Chlorobenzaldehyde) is an organic compound with the formula ClC₅H₄CHO. It is one of three isomeric monochlorinated benzaldehydes.

Preparation

It can be produced by hydrolysis of 4-chlorobenzal chloride:^[2]

ClC₅H₄CHCl₂ + H₂O → ClC₅H₄CHO + 2 HCl

It can also be produced by the oxidation of 4-chlorobenzyl alcohol.^[3]^[4] It can be further oxidized to 4-chlorobenzoic acid.^[5] It will react with malononitrile to form 4-chlorobenzylidenylmalononitrile. ^[6]4-Chlorobenzaldehyde reacts with benzylamine to produce N-(4-chlorobenzylidenyl)benzylamine。^[7]

References

^ "4-Chlorobenzaldehyde". pubchem.ncbi.nlm.nih.gov. Retrieved 3 April 2022.
^ Brühne, Friedrich; Wright, Elaine (2011). "Benzaldehyde". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a03_463.pub2. ISBN 978-3-527-30385-4.
^ Yang, Y. X.; An, X. Q.; Kang, M.; Zeng, W.; Yang, Z. W.; Ma, H. C. (2020). "A Simple and Effective Method for Catalytic Oxidation of Alcohols Using the Oxone/Bu4NHSO4 Oxidation System". Russian Journal of Organic Chemistry. 56 (3): 521–523. doi:10.1134/S1070428020030240. ISSN 1070-4280. S2CID 216049138. Retrieved 2021-05-10.
^ Alegre-Requena, Juan V.; Marqués-López, Eugenia; Herrera, Raquel P. (2018-01-04). "Organocatalyzed Enantioselective Aldol and Henry Reactions Starting from Benzylic Alcohols". Advanced Synthesis & Catalysis. 360 (1): 124–129. doi:10.1002/adsc.201701351. hdl:10261/186549. ISSN 1615-4150. S2CID 102499775. Retrieved 2021-05-10.
^ Hajimohammadi, Mahdi; Azizi, Naeleh; Tollabimazraeno, Sajjad; Tuna, Ali; Duchoslav, Jiri; Knör, Günther (2021). "Cobalt (II) Phthalocyanine Sulfonate Supported on Reduced Graphene Oxide (RGO) as a Recyclable Photocatalyst for the Oxidation of Aldehydes to Carboxylic Acids". Catalysis Letters. 151 (1): 36–44. doi:10.1007/s10562-020-03287-9. ISSN 1011-372X. S2CID 220312197. Retrieved 2021-05-10.
^ Gao, Ziyang; Yang, Hongyuan; Liu, Qing (2019). "Natural Seashell Waste as an Efficient and Low-Cost Catalyst for the Synthesis of Arylmethylenemalonitriles". CLEAN – Soil, Air, Water. 47 (10): 1900129. Bibcode:2019CSAW...4700129G. doi:10.1002/clen.201900129. ISSN 1863-0650. S2CID 203946880. Retrieved 2021-05-10.
^ He, Meixia; Lehn, Jean-Marie (2019-11-20). "Time-Dependent Switching of Constitutional Dynamic Libraries and Networks from Kinetic to Thermodynamic Distributions". Journal of the American Chemical Society. 141 (46): 18560–18569. Bibcode:2019JAChS.14118560H. doi:10.1021/jacs.9b09395. ISSN 0002-7863. PMID 31714075. S2CID 207938797. Retrieved 2021-05-10.

[1] "4-Chlorobenzaldehyde". pubchem.ncbi.nlm.nih.gov. Retrieved 3 April 2022.

[2] Brühne, Friedrich; Wright, Elaine (2011). "Benzaldehyde". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a03_463.pub2. ISBN 978-3-527-30385-4.

[3] Yang, Y. X.; An, X. Q.; Kang, M.; Zeng, W.; Yang, Z. W.; Ma, H. C. (2020). "A Simple and Effective Method for Catalytic Oxidation of Alcohols Using the Oxone/Bu4NHSO4 Oxidation System". Russian Journal of Organic Chemistry. 56 (3): 521–523. doi:10.1134/S1070428020030240. ISSN 1070-4280. S2CID 216049138. Retrieved 2021-05-10.

[4] Alegre-Requena, Juan V.; Marqués-López, Eugenia; Herrera, Raquel P. (2018-01-04). "Organocatalyzed Enantioselective Aldol and Henry Reactions Starting from Benzylic Alcohols". Advanced Synthesis & Catalysis. 360 (1): 124–129. doi:10.1002/adsc.201701351. hdl:10261/186549. ISSN 1615-4150. S2CID 102499775. Retrieved 2021-05-10.

[5] Hajimohammadi, Mahdi; Azizi, Naeleh; Tollabimazraeno, Sajjad; Tuna, Ali; Duchoslav, Jiri; Knör, Günther (2021). "Cobalt (II) Phthalocyanine Sulfonate Supported on Reduced Graphene Oxide (RGO) as a Recyclable Photocatalyst for the Oxidation of Aldehydes to Carboxylic Acids". Catalysis Letters. 151 (1): 36–44. doi:10.1007/s10562-020-03287-9. ISSN 1011-372X. S2CID 220312197. Retrieved 2021-05-10.

[6] Gao, Ziyang; Yang, Hongyuan; Liu, Qing (2019). "Natural Seashell Waste as an Efficient and Low-Cost Catalyst for the Synthesis of Arylmethylenemalonitriles". CLEAN – Soil, Air, Water. 47 (10): 1900129. Bibcode:2019CSAW...4700129G. doi:10.1002/clen.201900129. ISSN 1863-0650. S2CID 203946880. Retrieved 2021-05-10.

[7] He, Meixia; Lehn, Jean-Marie (2019-11-20). "Time-Dependent Switching of Constitutional Dynamic Libraries and Networks from Kinetic to Thermodynamic Distributions". Journal of the American Chemical Society. 141 (46): 18560–18569. Bibcode:2019JAChS.14118560H. doi:10.1021/jacs.9b09395. ISSN 0002-7863. PMID 31714075. S2CID 207938797. Retrieved 2021-05-10.

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