40137-29-9

Usage

Uses

Used in Pharmaceutical Industry:
4-Chloro-2-methylbenzaldehyde is used as a reactant in the synthesis of benzylidene cyclopentenediones, which are inhibitors against botulinum neurotoxin A's zinc endopeptidase. This application is significant in the development of potential treatments for botulism, a severe and potentially fatal form of food poisoning caused by the toxins produced by the bacterium Clostridium botulinum.
Used in Fragrance Industry:
Due to its unique aromatic and spicy scent, 4-chloro-2-methylbenzaldehyde is utilized as a key ingredient in the creation of various fragrances and perfumes. Its distinct odor profile contributes to the overall complexity and richness of the fragrance, making it a valuable addition to the perfumer's palette.
Used in Flavor Industry:
In addition to its applications in the fragrance industry, 4-chloro-2-methylbenzaldehyde is also employed in the flavor industry to impart specific taste and aroma characteristics to various food and beverage products. Its unique flavor profile can enhance the overall taste experience, making it a sought-after ingredient in the development of new and innovative flavors.
Used in Chemical Synthesis:
4-Chloro-2-methylbenzaldehyde serves as an important intermediate in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its versatile chemical structure allows for further functionalization and modification, making it a valuable building block in the development of new and improved chemical products.

InChI:InChI=1/C8H7ClO/c1-6-4-8(9)3-2-7(6)5-10/h2-5H,1H3

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 74-88-4 methyl iodide 
• 6611-78-5 4-dichloromethyl-4-methyl-2,5-cyclohexadienone 
• 10026-13-8 phosphorus pentachloride 
• 142-25-6 N,N',N'-trimethylenediamine 
• 201230-82-2 carbon monoxide 
• 108-41-8 1-chloro-3-methylbenzene 
• 615-60-1 4-chloro-1,2-dimethylbenzene 
• 75-17-2 formaldoxime 
• 95-69-2 4-chloro-2-methylbenzeneamine 

Downstream Products

• 1201189-90-3 4-chloro-2-methyl-1-((E)-2-nitro-vinyl)-benzene 
• 1616363-92-8 C₂₀H₂₄ClN₃O₂S 
• 1616363-64-4 (4R)-4-(4-chloro-2-methylphenyl)-1-methyl-3-(2-pyridyl)-4,6,7,8-tetrahydropyrazolo[3,4-e][1,4]thiazepine 
• 1616363-65-5 (4S)-4-(4-chloro-2-methylphenyl)-1-methyl-3-(2-pyridyl)-4,6,7,8-tetrahydropyrazolo[3,4-e][1,4]thiazepine 
• 1616363-62-2 (4S)-4-(4-chloro-2-methylphenyl)-3-cyclopropyl-1,6,6-trimethyl-7,8-dihydro-4H-pyrazolo[3,4-e][1,4]thiazepine 
• 1616363-63-3 (4R)-4-(4-chloro-2-methylphenyl)-3-cyclopropyl-1,6,6-trimethyl-7,8-dihydro-4H-pyrazolo[3,4-e][1,4]thiazepine 
• 1616363-61-1 4-(4-chloro-2-methylphenyl)-3-cyclopropyl-1,6,6-trimethyl-7,8-dihydro-4H-pyrazolo[3,4-e][1,4]thiazepine 
• 1616360-37-2 4-(4-chloro-2-methylphenyl)-1-methyl-3-(2-pyridyl)-4,6,7,8-tetrahydropyrazolo[3,4-e][1,4]thiazepine 
• 1616360-80-5 4-(4-chloro-2-methylphenyl)-3-cyclopropyl-1,6,6-trimethyl-4,8-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one 
• 1616360-36-1 4-(4-chloro-2-methylphenyl)-1-methyl-3-(2-pyridyl)-4,8-dihydropyrazolo[3,4-e][1,4]thiazepin-7-one 
• 1616363-78-0 4-(4-chloro-2-methylphenyl)-1,7-dimethyl-3-(2-pyridyl)-4,6-dihydropyrazolo[3,4-e][1,4]thiazepine 
• 1438071-12-5 N-(4-chloro-2-methylbenzyl)-N-(4-chlorobenzyl)-1-(5-nitrothiophen-2-yl)methanamine 
• 1441734-83-3 1-(3-chloro-2-fluoro-phenyl)-5-(4-chloro-2-methyl-phenyl)-3-hydroxy-4-isobutyryl-1,5-dihydro-pyrrol-2-one 
• 1441739-40-7 5-(4-chloro-2-methyl-phenyl)-3-hydroxy-4-isobutyryl-1-(4-methoxy-benzyl)-1,5-dihydro-pyrrol-2-one 

Relevant academic research and scientific papers

Synthesis of Tetrahydroisoquinolines by Visible-Light-Mediated 6- exo -trig Cyclization of α-Aminoalkyl Radicals

Starting from the respective tertiary α-silylmethyl amines, the intramolecular cyclization of α-aminoalkyl radicals to Michael acceptors produced tetrahydroisoquinolines. The reaction conditions included the use of 5 molpercent of an iridium photoredox catalyst, dimethylformamide as the solvent, and equimolar amounts of water and cesium carbonate as the additives. 13 substrates were synthesized from ortho -alkylbenzaldehydes in a three-step procedure involving a carbonyl condensation, a radical bromination, and a substitution by a secondary α-silylmethyl amine. After optimization of the photocyclization, the reaction delivered tetrahydroisoquinolines in moderate to high yields (41-83percent). A facial diastereoselectivity (dr ? 80:20) was observed with chiral substrates and a crystal structure provided evidence for the relative configuration of the major diastereoisomer. A catalytic cycle with direct electron transfer to the photoexcited metal catalyst is proposed.

Method for producing halogen-substituted aromatic aldehyde

In the production method of the invention, a halogen-substituted aromatic compound is reacted with carbon monoxide in the presence of hydrogen fluoride and boron trifluoride into a corresponding halogen-substituted aromatic aldehyde. By the use of hydrogen fluoride and boron trifluoride, the para position to halogen atom is selectively formylated to provide the halogen-substituted aromatic aldehyde in high yields in a short reaction time even at temperatures lower than room temperature.

Therapeutic agents useful for treating inflammatory diseases

This invention relates to compounds of formula I and pharmaceutically acceptable salts thereof STR1 in which R1, R2 and R3 independently represent hydrogen, halo, alkyl, alkoxy, phenoxy, phenyl, alkoxycarbonyl, --NR13 R14, halogenated alkoxy, halogenated alkyl, benzyloxy, hydroxy, hydroxyalkyl, (C2-6 alkoxycarbonyl)vinyl, --S(O)n R7, carbamoylalkyl, alkoxycarbonylalkyl, --CONR11 R12, or R1 and R2 together with the phenyl ring represent a naphthyl group; R4 and R5 independently represent hydrogen, alkyl, phenyl or together with the carbon atom represent C3-6 cycloalkyl; R6 represents hydrogen, alkyl or ω-hydroxy alkyl; A represents C2-9 alkylene; R8 represents hydrogen, alkyl, halo, alkoxy, hydroxyalkyl, benzyl or phenyl; R9 and R10 independently represent hydrogen, alkyl, halo, alkoxy, phenyl, hydroxyalkyl, alkoxycarbonyl, nitro, --NR30 R31, alkanoyloxyalkyl, or aminomethyl; which are antiinflammatory and antiallergic agents. Compositions containing these compounds and processes to make them are also disclosed.

A Convenient Oxidation of Benzylic Methyl, Methylene, and Methine Groups with Potassium Permanganate/Triethylamine Reagent

A useful and versatile procedure for benzylic oxidations with potassium permanganate/triethylamine has been developed.The methyl, methylene and methine groups are oxidized in good to excellent yields to benzylic aldehydes and ketones and to tertiary benzyl alcohols, respectively.This procedure can easily be carried out in conventional organic solvents without using any phase-transfer or supported catalysts.

Transition Metal Catalyzed Grignard Cross-Coupling to Ortho-Halogenated Aryl Imines. An Efficient Synthesis of Ortho-Substituted Aryl Aldehydes

N-(o-Halogenated benzylidene)cyclohexylamines 2 were successfully reacted with reducing and nonreducing Grignard reagents in a transition metal catalyzed cross-coupling reaction resulting in an efficient single-step synthesis of ortho-substituted benzaldehydes after acidic workup.The dihalogenated benzylidene amines reacted regioselectively at the amine-activated ortho position to yield ortho-substituted halogenated benzaldehydes.

Ortho Metalation Directed by α-Amino Alkoxides

The addition of aromatic aldehydes to certain lithium dialkylamides in benzene or tetrahydrofuran gave α-amino alkoxides which were ortho lithiated with excess n-butyllithium.Subsequent alkylation and hydrolysis provided ortho-substituted aromatic aldehydes via a one-pot reaction.The ortho metalation of α-amino alkoxides derived from 1- and 2-naphthaldehyde and various substituted benzaldehydes was examined.When N,N,N'-trimethylethylenediamine was used as the amine component of the α-amino alkoxide, metalation could be carried out at lower temperatures.This rate increase is due to an intramolecular TMEDA-like assisted metalation.The synthetic utility of this ortho metalation, including how varying the amine component of the α-amino alkoxide affects the regiochemistry and metalation rate, is discussed.

A ONE-POT ORTHO ALKYLATION OF AROMATIC ALDEHYDES

The addition of aromatic aldehydes to lithium N-methylpiperazide in benzene gave α-amino alkoxides which were ortho-lithiated with excess n-butyllithium.Subsequent alkylation and hydrolysis provided ortho-substituted aromatic aldehydes via a one-pot reaction.