6140-64-3

Basic information

• Product Name: 1-Methylcyclohexanecarboxaldehyde
• Synonyms: 1-Methylcyclohexanecarboxaldehyde;1-Formyl-1-methylcyclohexane;1-Methylcyclohexane-1-carboxaldehyde 95%;Cyclohexanecarboxaldehyde, 1-Methyl-;1-METHYLCYCLOHEXANECARBALDEHYDE;1-Methylcyclohexane-1-carboxaldehyde;1-Methylcyclohexane-1-carboxaldehyde95%;1-methylcyclohexane-1-carbaldehyde
• CAS NO: 6140-64-3
• Molecular Formula: C₈H₁₄O
• Molecular Weight: 126.198
• Mol File: 6140-64-3.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 85 °C(Press: 20 Torr)
• Flash Point: 51 °C
• Appearance: /
• Density: 0.9407 g/cm3
• CAS DataBase Reference: 1-Methylcyclohexanecarboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methylcyclohexanecarboxaldehyde(6140-64-3)
• EPA Substance Registry System: 1-Methylcyclohexanecarboxaldehyde(6140-64-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Hazardous Substances Data: 6140-64-3(Hazardous Substances Data)

Usage

Uses

1-Methylcyclohexanecarboxaldehyde is used in preparation of Indazole derivatives as IDO and TDO modulators.

Synthesis Reference(s)

Journal of the American Chemical Society, 114, p. 4422, 1992 DOI: 10.1021/ja00037a070

Upstream product

• 1453-25-4 1-methylcycloheptene 
• 55089-30-0 2-(1-methyl-cyclohexyl)-4,5-dihydro-thiazole 
• 64-18-6 formic acid 
• 502-41-0 cycloheptanol 
• 24463-38-5 2-(1-Methyl-cyclohexyl)-[1,3]dioxolane 
• 1123-25-7 1-methyl-1-cyclohexanecarboxylic acid 
• 2890-61-1 1-methyl-1-cyclohexancarboxylic acid chloride 
• 53282-55-6 (trimethylsiloxymethylidene)cyclohexane 
• 333-27-7 methyl trifluoromethanesulfonate 
• 2043-61-0 cyclohexanecarbaldehyde 
• 74-88-4 methyl iodide 
• 111-24-0 1,5-dibromo-pentane 
• 825-04-7 methyl 1-methylcyclohexanecarboxylate 
• 14064-13-2 (1-methylcyclohexyl)methanol 

Downstream Products

• 62257-88-9 N,N-dimethyl-1-(1-methylcyclohexyl)methanamine 
• 161139-35-1 methyl N-(4-methoxybenzyl)-N-<3-(1-methylcyclohexyl)-3-oxopropanoyl>glycinate 
• 92319-11-4 (+/-)-Cyclohexyl-<1-methyl-cyclohexyl>-methanol 
• 103096-65-7 N-(1-Methyl-cyclohexylmethylen)-(1-methyl-cyclohexylmethyl)-amin 
• 923591-39-3 (2R)-{[(1R)-2-hydroxy-1-phenylethyl]amino}(1-methylcyclohexyl)acetonitrile 
• 1227718-79-7 (Z)-3-(1-methylcyclohexyl)acrylonitrile 
• 1262639-74-6 2-(methyl-((1-methylcyclohexyl)methyl)amino)ethanenitrile 
• 1434277-55-0 (3,3-dimethylcycloprop-1-en-1-yl)(1-methylcyclohexyl)methanol 
• 1433188-06-7 1-(1-methylyclohexylcarbonyl)-1,2-hydrazinedicarboxylic acid 1,2-diisopropyl ester 
• 107367-82-8 4-chloromethyl-2-(1-methylcyclohexan-1-yl)-5-methyloxazole 
• 50993-21-0 1-methyl-N-phenylcyclohexane-1-carboxamide 
• 1332894-81-1 (R)-methyl 4-(1-((1-methylcyclohexyl)methylamino)ethyl)benzoate 
• 161139-41-9 N-(4-methoxybenzyl)-3-(1-methylcyclohexanecarbonyl)tetramic acid 

Relevant articles and documents

Iron-Catalyzed Oxidative Decarbonylative α-Alkylation of Acyl-Substituted Furans with Aliphatic Aldehydes as the Alkylating Agents

A protocol for FeCl2-catalyzed oxidative decarbonylative α-alkylation of acyl furans using alkyl aldehydes as the alkylating agents has been developed. This protocol affords α-alkyl-α-acylfurans in moderate to good yields in a practical and sustainable fa

Mechanistic Studies on the Organocatalytic α-Chlorination of Aldehydes: The Role and Nature of Off-Cycle Intermediates

Herein we report the isolation and characterization of aminal intermediates in the organocatalytic α-chlorination of aldehydes. These species are stable covalent ternary adducts of the substrate, the catalyst and the chlorinating reagent. NMR-assisted kinetic studies and isotopic labeling experiments with the isolated intermediate did not support its involvement in downstream stereoselective processes as proposed by Blackmond. By tuning the reactivity of the chlorinating reagent, we were able to suppress the accumulation of rate-limiting off-cycle intermediates. As a result, an efficient and highly enantioselective catalytic system with a broad functional group tolerance was developed.

Tropylium ion mediated α-cyanation of amines

Tropylium ion mediated α-cyanation of amines is described. Even in the presence of KCN, tropylium ion is capable of oxidizing various amine substrates, and the resulting iminium ions undergo salt metathesis with cyanide ion to produce aminonitriles. The byproducts of this transformation are simply cycloheptatriene, a volatile hydrocarbon, and water-soluble potassium tetrafluoroborate. Thirteen total substrates are shown for the α-cyanation procedure, including a gram scale synthesis of 17β-cyanosparteine. In addition, a tropylium ion mediated oxidative aza-Cope rearrangement is demonstrated.