46021-27-6

Basic information

• Product Name: 1,2-Cyclohexanedicarbonyl dichloride, trans-(-)- (9CI)
• Synonyms: 1,2-Cyclohexanedicarbonyl dichloride, trans-(-)- (9CI)
• CAS NO: 46021-27-6
• Molecular Formula: C₈H₁₀Cl₂O₂
• Molecular Weight: 209.0698
• Product Categories: ACIDHALIDE
• Mol File: 46021-27-6.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1,2-Cyclohexanedicarbonyl dichloride, trans-(-)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Cyclohexanedicarbonyl dichloride, trans-(-)- (9CI)(46021-27-6)
• EPA Substance Registry System: 1,2-Cyclohexanedicarbonyl dichloride, trans-(-)- (9CI)(46021-27-6)

Safety Data

• Hazardous Substances Data: 46021-27-6(Hazardous Substances Data)

Usage

Appearance

Colorless liquid

Synonyms

trans-1,2-Cyclohexanedicarbonyl dichloride

Usage

Organic synthesis
Preparation of various organic compounds
Building block in the production of dyes, pharmaceuticals, and agrochemicals

Reactivity

Highly reactive

Safety concerns

Potential for causing skin and eye irritation
Respiratory issues if inhaled
Environmental damage if released into the environment

Handling

Must be handled with care due to its reactivity and potential hazards

Upstream product

• 2305-32-0 trans-1,2-cyclohexanedicarboxylic acid 
• 610-10-6 (1S,2S)-cyclohexane-1,2-dicarboxylic acid 

Downstream Products

• 115720-23-5 (+/-)-trans-1-cyano-cyclohexane-carboxylic acid-(2) 
• 393078-38-1 (1S,2S)-2-(pyridin-2-ylcarbamoyl)cyclohexanecarboxylic acid 
• 568588-45-4 (S,S)-1,2-bis[(S)-(4-phenyl)-1,3-oxazolin-2-yl]cyclohexane 
• 568588-48-7 (1S,2S)-Cyclohexane-1,2-dicarboxylic acid bis-[((S)-2-hydroxy-1-phenyl-ethyl)-amide] 
• 90682-77-2 (3E,9E)-1,2-Diphenyl-3,10-bis-trimethylsilanyloxy-1,2,5,6,7,8-hexahydro-[1,2]diphosphecine 
• 104722-26-1 trans-1,2-dibenzoylcyclohexane 

Relevant articles and documents

Synthesis of new C2-symmetric chiral bisamides from (1S,2S)-cyclohexane-1,2-dicarboxylic acid

series of new C2-symmetric (1S,2S)-cyclohexane-1,2-dicarboxamides was synthesized from (1S,2S)-cyclohexane-1,2-dicarbonyl dichloride and N-benzyl-substituted aromatic amines, which were prepared from 2-aminopyridine, 2-chloroaniline, and 2-aminophenol via imine formation with benzaldehyde and subsequent reduction with NaBH4. (1S,2S)-N,N'-Dibenzyl-N,N'-bis[2-(benzyloxy)-phenyl]cyclohexane-1,2-dicarboxamide was converted to (1S,2S)-N,N'-dibenzyl-N,N'-bis(2-hydroxyphenyl) cyclohexane-1,2-dicarboxamide via hydrogenolysis in the presence of Pd(OH)2 on active carbon powder.

Diastereoselective imine-bond formation through complementary double-helix formation

Optically active amidine dimer strands having a variety of chiral and achiral linkers with different stereostructures are synthesized and used as templates for diastereoselective imine-bond formations between two achiral carboxylic acid monomers bearing a terminal aldehyde group and racemic 1,2-cyclohexanediamine, resulting in a preferred-handed double helix stabilized by complementary salt bridges. The diastereoselectivity of the racemic amine is significantly affected by the chirality of the amidine residues along with the rigidity and/or chirality of the linkers in the templates. NMR and kinetic studies reveal that the present imine-bond formation involves a two-step reversible reaction. The second step involves formation of a preferred-handed complementary double helix assisted by the chiral amidine templates and determines the overall reaction rate and diastereoselectivity of the amine.