4-Chlorobenzaldehyde

Last updated
4-Chlorobenzaldehyde
4-Chlorbenzaldehyd.svg
Identifiers
3D model (JSmol)
ChEMBL
ECHA InfoCard 100.002.953 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-247-4
KEGG
PubChem CID
UNII
UN number 2811
  • InChI=1S/C7H5ClO/c8-7-3-1-6(5-9)2-4-7/h1-5H
    Key: AVPYQKSLYISFPO-UHFFFAOYSA-N
  • C1=CC(=CC=C1C=O)Cl
Properties
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: [1]
GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
Warning
H302, H315, H317, H319, H411
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).

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]

Related Research Articles

<span class="mw-page-title-main">Catalysis</span> Process of increasing the rate of a chemical reaction

Catalysis is the increase in rate of a chemical reaction due to an added substance known as a catalyst. Catalysts are not consumed by the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycles quickly, very small amounts of catalyst often suffice; mixing, surface area, and temperature are important factors in reaction rate. Catalysts generally react with one or more reactants to form intermediates that subsequently give the final reaction product, in the process of regenerating the catalyst.

<span class="mw-page-title-main">Epoxide</span> Organic compounds with a carbon-carbon-oxygen ring

In organic chemistry, an epoxide is a cyclic ether, where the ether forms a three-atom ring: two atoms of carbon and one atom of oxygen. This triangular structure has substantial ring strain, making epoxides highly reactive, more so than other ethers. They are produced on a large scale for many applications. In general, low molecular weight epoxides are colourless and nonpolar, and often volatile.

In organic chemistry, an acyl chloride is an organic compound with the functional group −C(=O)Cl. Their formula is usually written R−COCl, where R is a side chain. They are reactive derivatives of carboxylic acids. A specific example of an acyl chloride is acetyl chloride, CH3COCl. Acyl chlorides are the most important subset of acyl halides.

<span class="mw-page-title-main">Acyl halide</span> Oxoacid compound with an –OH group replaced by a halogen

In organic chemistry, an acyl halide is a chemical compound derived from an oxoacid by replacing a hydroxyl group with a halide group.

<span class="mw-page-title-main">Benzyl group</span> Chemical group (–CH₂–C₆H₅)

In organic chemistry, benzyl is the substituent or molecular fragment possessing the structure R−CH2−C6H5. Benzyl features a benzene ring attached to a methylene group.

<span class="mw-page-title-main">Benzoyl chloride</span> Organochlorine compound (C7H5ClO)

Benzoyl chloride, also known as benzenecarbonyl chloride, is an organochlorine compound with the formula C7H5ClO. It is a colourless, fuming liquid with an irritating odour, and consists of a benzene ring with an acyl chloride substituent. It is mainly useful for the production of peroxides but is generally useful in other areas such as in the preparation of dyes, perfumes, pharmaceuticals, and resins.

The Cannizzaro reaction, named after its discoverer Stanislao Cannizzaro, is a chemical reaction which involves the base-induced disproportionation of two molecules of a non-enolizable aldehyde to give a primary alcohol and a carboxylic acid.

<span class="mw-page-title-main">Triphenylphosphine</span> Chemical compound

Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 and often abbreviated to PPh3 or Ph3P. It is versatile compound that is widely used as a reagent in organic synthesis and as a ligand for transition metal complexes, including ones that serve as catalysts in organometallic chemistry. PPh3 exists as relatively air stable, colorless crystals at room temperature. It dissolves in non-polar organic solvents such as benzene and diethyl ether.

<span class="mw-page-title-main">Gold(III) chloride</span> Chemical compound

Gold(III) chloride, traditionally called auric chloride, is an inorganic compound of gold and chlorine with the molecular formula Au2Cl6. The "III" in the name indicates that the gold has an oxidation state of +3, typical for many gold compounds. It has two forms, the monohydrate (AuCl3·H2O) and the anhydrous form, which are both hygroscopic and light-sensitive solids. This compound is a dimer of AuCl3. This compound has a few uses, such as an oxidizing agent and for catalyzing various organic reactions.

The Tishchenko reaction is an organic chemical reaction that involves disproportionation of an aldehyde in the presence of an alkoxide. The reaction is named after Russian organic chemist Vyacheslav Tishchenko, who discovered that aluminium alkoxides are effective catalysts for the reaction.

<span class="mw-page-title-main">Trimethylsilyl chloride</span> Organosilicon compound with the formula (CH3)3SiCl

Trimethylsilyl chloride, also known as chlorotrimethylsilane is an organosilicon compound, with the formula (CH3)3SiCl, often abbreviated Me3SiCl or TMSCl. It is a colourless volatile liquid that is stable in the absence of water. It is widely used in organic chemistry.

<span class="mw-page-title-main">Carbonate ester</span> Chemical group (R–O–C(=O)–O–R)

In organic chemistry, a carbonate ester is an ester of carbonic acid. This functional group consists of a carbonyl group flanked by two alkoxy groups. The general structure of these carbonates is R−O−C(=O)−O−R' and they are related to esters, ethers and also to the inorganic carbonates.

<span class="mw-page-title-main">Benzylamine</span> Chemical compound

Benzylamine is an organic chemical compound with the condensed structural formula C6H5CH2NH2 (sometimes abbreviated as PhCH2NH2 or BnNH2). It consists of a benzyl group, C6H5CH2, attached to an amine functional group, NH2. This colorless water-soluble liquid is a common precursor in organic chemistry and used in the industrial production of many pharmaceuticals. The hydrochloride salt was used to treat motion sickness on the Mercury-Atlas 6 mission in which NASA astronaut John Glenn became the first American to orbit the Earth.

In chemistry, carbonylation refers to reactions that introduce carbon monoxide (CO) into organic and inorganic substrates. Carbon monoxide is abundantly available and conveniently reactive, so it is widely used as a reactant in industrial chemistry. The term carbonylation also refers to oxidation of protein side chains.

<span class="mw-page-title-main">Triethyl phosphite</span> Chemical compound

Triethyl phosphite is an organophosphorus compound, specifically a phosphite ester, with the formula P(OCH2CH3)3, often abbreviated P(OEt)3. It is a colorless, malodorous liquid. It is used as a ligand in organometallic chemistry and as a reagent in organic synthesis.

Benzaldehyde (C6H5CHO) is an organic compound consisting of a benzene ring with a formyl substituent. It is among the simplest aromatic aldehydes and one of the most industrially useful.

<span class="mw-page-title-main">Organobismuth chemistry</span>

Organobismuth chemistry is the chemistry of organometallic compounds containing a carbon to bismuth chemical bond. Applications are few. The main bismuth oxidation states are Bi(III) and Bi(V) as in all higher group 15 elements. The energy of a bond to carbon in this group decreases in the order P > As > Sb > Bi. The first reported use of bismuth in organic chemistry was in oxidation of alcohols by Frederick Challenger in 1934 (using Ph3Bi(OH)2). Knowledge about methylated species of bismuth in environmental and biological media is limited.

Organogold chemistry is the study of compounds containing gold–carbon bonds. They are studied in academic research, but have not received widespread use otherwise. The dominant oxidation states for organogold compounds are I with coordination number 2 and a linear molecular geometry and III with CN = 4 and a square planar molecular geometry.

<span class="mw-page-title-main">Barium manganate</span> Chemical compound

Barium manganate is an inorganic compound with the formula BaMnO4. It is used as an oxidant in organic chemistry. It belongs to a class of compounds known as manganates in which the manganese resides in a +6 oxidation state. Manganate should not be confused with permanganate which contains manganese(VII). Barium manganate is a powerful oxidant, popular in organic synthesis and can be used in a wide variety of oxidation reactions.

<span class="mw-page-title-main">2-Chlorobenzaldehyde</span> Chemical compound

2-Chlorobenzaldehyde (o-Chlorobenzaldehyde) is an organic compound with the formula ClC5H4CHO. It is one of three isomeric monochlorinated benzaldehyde. 2-Chlorobenzaldehyde]] and 3-chlorobenzaldehyde are the other isomers. Whereas benzaldehyde is prone to autoxidation, the 2-chloro derivatives are more air-stable.

References

  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. doi:10.1021/jacs.9b09395. ISSN   0002-7863. PMID   31714075. S2CID   207938797 . Retrieved 2021-05-10.