4-Chlorobenzaldehyde
{{Chembox
| Name =
| ImageFile = 4-Chlorbenzaldehyd.svg
| ImageSize = 70px
| ImageAlt =
| IUPACName =
| OtherNames =
| Section1 = {{Chembox Identifiers
| CASNo = 104-88-1
| CASNo_Ref = {{cascite|correct|CAS}}
| Beilstein = 385858
| ChEMBL = 1474
| ChemSpiderID = 21106019
| EC_number = 203-247-4
| KEGG = C06648
| PubChem = 7726
| UNNumber = 2811
| UNII = E67727UP9Z
| StdInChI=1S/C7H5ClO/c8-7-3-1-6(5-9)2-4-7/h1-5H
| StdInChIKey = AVPYQKSLYISFPO-UHFFFAOYSA-N
| SMILES = C1=CC(=CC=C1C=O)Cl
}}
| Section2 = {{Chembox Properties
| C=7 | H=5 | Cl=1 | O=1
| Appearance =
| Density =
| MeltingPtC = 47.5
| BoilingPtC = 213.5
| Solubility = }}
| Section3 = {{Chembox Hazards
| GHSPictograms = {{GHS07}}{{GHS09}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|302|315|317|319|411}}
| PPhrases = {{P-phrases|261|264|264+265|270|271|272|273|280|301+317|302+352|304+340|305+351+338|319|321|330|332+317|333+313|337+317|362+364|391|403+233|405|501}}
| MainHazards =
| FlashPt =
}}
}}
4-Chlorobenzaldehyde (p-Chlorobenzaldehyde) is an organic compound with the formula {{chem2|ClC6H4CHO}}. It is one of three isomeric monochlorinated benzaldehydes.
Preparation
It can be produced by hydrolysis of 4-chlorobenzal chloride:{{cite book |doi=10.1002/14356007.a03_463.pub2 |chapter=Benzaldehyde |title=Ullmann's Encyclopedia of Industrial Chemistry |date=2011 |last1=Brühne |first1=Friedrich |last2=Wright |first2=Elaine |isbn=978-3-527-30385-4 }}
:{{chem2|ClC6H4CHCl2 + H2O -> ClC6H4CHO + 2 HCl}}
It can also be produced by the oxidation of 4-chlorobenzyl alcohol.{{cite journal |last1=Yang |first1=Y. X. |last2=An |first2=X. Q. |last3=Kang |first3=M. |last4=Zeng |first4=W. |last5=Yang |first5=Z. W. |last6=Ma |first6=H. C. |date=2020 |title=A Simple and Effective Method for Catalytic Oxidation of Alcohols Using the Oxone/Bu4NHSO4 Oxidation System |url=https://link.springer.com/10.1134/S1070428020030240 |journal=Russian Journal of Organic Chemistry |language=en |volume=56 |issue=3 |pages=521–523 |doi=10.1134/S1070428020030240 |issn=1070-4280 |s2cid=216049138 |accessdate=2021-05-10}}{{cite journal |last1=Alegre-Requena |first1=Juan V. |last2=Marqués-López |first2=Eugenia |last3=Herrera |first3=Raquel P. |date=2018-01-04 |title=Organocatalyzed Enantioselective Aldol and Henry Reactions Starting from Benzylic Alcohols |url=https://onlinelibrary.wiley.com/doi/10.1002/adsc.201701351 |journal=Advanced Synthesis & Catalysis |language=en |volume=360 |issue=1 |pages=124–129 |doi=10.1002/adsc.201701351 |issn=1615-4150 |s2cid=102499775 |accessdate=2021-05-10|hdl=10261/186549 |hdl-access=free }} It can be further oxidized to 4-chlorobenzoic acid.{{cite journal |last1=Hajimohammadi |first1=Mahdi |last2=Azizi |first2=Naeleh |last3=Tollabimazraeno |first3=Sajjad |last4=Tuna |first4=Ali |last5=Duchoslav |first5=Jiri |last6=Knör |first6=Günther |date=2021 |title=Cobalt (II) Phthalocyanine Sulfonate Supported on Reduced Graphene Oxide (RGO) as a Recyclable Photocatalyst for the Oxidation of Aldehydes to Carboxylic Acids |url=https://link.springer.com/10.1007/s10562-020-03287-9 |journal=Catalysis Letters |language=en |volume=151 |issue=1 |pages=36–44 |doi=10.1007/s10562-020-03287-9 |issn=1011-372X |s2cid=220312197 |accessdate=2021-05-10}} It will react with malononitrile to form 4-chlorobenzylidenylmalononitrile. {{cite journal |last1=Gao |first1=Ziyang |last2=Yang |first2=Hongyuan |last3=Liu |first3=Qing |date=2019 |title=Natural Seashell Waste as an Efficient and Low-Cost Catalyst for the Synthesis of Arylmethylenemalonitriles |url=https://onlinelibrary.wiley.com/doi/10.1002/clen.201900129 |journal=CLEAN – Soil, Air, Water |language=en |volume=47 |issue=10 |pages=1900129 |doi=10.1002/clen.201900129 |bibcode=2019CSAW...4700129G |issn=1863-0650 |s2cid=203946880 |accessdate=2021-05-10}}4-Chlorobenzaldehyde reacts with benzylamine to produce N-(4-chlorobenzylidenyl)benzylamine。{{cite journal |last1=He |first1=Meixia |last2=Lehn |first2=Jean-Marie |date=2019-11-20 |title=Time-Dependent Switching of Constitutional Dynamic Libraries and Networks from Kinetic to Thermodynamic Distributions |url=https://pubs.acs.org/doi/10.1021/jacs.9b09395 |journal=Journal of the American Chemical Society |language=en |volume=141 |issue=46 |pages=18560–18569 |doi=10.1021/jacs.9b09395 |issn=0002-7863 |pmid=31714075 |bibcode=2019JAChS.14118560H |s2cid=207938797 |accessdate=2021-05-10}}