21963-41-7

Basic information

• Product Name: (1S,2S)-1,2-CYCLOHEXANEDICARBOXYLIC ACID
• Synonyms: (1S,2S)-(+)-1,2-CYCLOHEXANEDICARBOXYLIC ACID;(1S,2S)-1,2-CYCLOHEXANEDICARBOXYLIC ACID;(S,S)-CYCLOHEXANE-1,2-DICARBOXYLIC ACID;(1S,2S)-(+)-Cyclohexanedicarboxylic acid;1,2-Cyclohexanedicarboxylic acid, (1S,2S)-;(1S,2S)-1,2-CYCLOHEXANEDICARBOXYLIC ACID 98+%;(1S,2S)-Cyclohexane-1,2-dicarboxylic acid, 98+%;(1S-trans)-1,2-Cyclohexanedicarboxylic acid
• CAS NO: 21963-41-7
• Molecular Formula: C₈H₁₂O₄
• Molecular Weight: 172.18
• Product Categories: Carboxylic Acids (Chiral);Chiral Building Blocks;Synthetic Organic Chemistry
• Mol File: 21963-41-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 184 °C
• Boiling Point: 384.1 °C at 760 mmHg
• Flash Point: 200.3 °C
• Appearance: /
• Density: 1.314
• Refractive Index: 18 ° (C=1, Acetone)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Soluble in acetone(almost transparency).
• PKA: 4.18±0.28(Predicted)
• CAS DataBase Reference: (1S,2S)-1,2-CYCLOHEXANEDICARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-1,2-CYCLOHEXANEDICARBOXYLIC ACID(21963-41-7)
• EPA Substance Registry System: (1S,2S)-1,2-CYCLOHEXANEDICARBOXYLIC ACID(21963-41-7)

Safety Data

• Hazardous Substances Data: 21963-41-7(Hazardous Substances Data)

Usage

Uses

A series of new C2-symmetric (1S,2S)-cyclohexane-1,2-dicarboxamides was synthesized from (1S,2S)-Cyclohexane-1,2-dicarboxylic acid.

Upstream product

• 2305-32-0 trans-1,2-cyclohexanedicarboxylic acid 
• 1687-29-2 dimethyl cis-1,2-cyclohexanedicarboxylate 

Downstream Products

• 7436-01-3 (1S)-trans-1,2-bis-(toluene-4-sulfonyloxymethyl)-cyclohexane 
• 2756-85-6 1-aminocyclohexane carboxylic acid 
• 5691-19-0 rac-trans-2-aminocyclohexanecarboxylic acid 
• 70223-77-7 (1S,2S)-1,2-bis(diphenylphosphinomethyl)cyclohexane 
• 38261-85-7 (1S,2S)-1,2-bis(bromomethyl)cyclohexane 
• 144540-72-7 trans-hexahydrophthalide 
• 57280-65-6 trans-2-(hydroxymethyl)cyclohexanecarboxylic acid 
• 31982-90-8 (1S,2S)-(+)-cyclohexane-1,2-dicarboxylic acid dimethyl ester 
• 1263273-14-8 (1S,2S)-2-((3,5-dichlorophenyl)carbamoyl)cyclohexanecarboxylic acid 

Relevant articles and documents

Enantioselective Synthesis of ((1 R,2 R)-Cyclohexane-1,2-diyl)bis(methylene)dimethanesulfonate, a Lurasidone Hydrochloride Intermediate

A concise, economical, and highly enantioselective synthesis of bismesylate intermediate of lurasidone HCl, an antipsychotic, has been developed. The key steps involved in the synthesis are thionyl chloride-catalyzed esterification of tetrahydrophthalic anhydride in MeOH, epimerization of cis to trans isomer, hydrolysis of the diester, resolution of the diacid, reduction with Red-Al, and finally bismesylation of the corresponding diol, which provided the desired intermediate ((1 R,2 R)-cyclohexane-1,2-diyl)bis(methylene) dimethanesulfonate in overall good yield.

Rational tuning chelate size of bis-oxazoline ligands to improve enantioselectivity in the asymmetric aziridination of chalcones

Chalcones were asymmetrically aziridinated with [N-(p-toluenesulfonyl) imino]phenyliodinane (PhI=NTs) as a nitrene source under catalysis of CuOTf and a series of cyclohexane-linked bis-oxazolines (cHBOXes), which are chelate size rationally tuned bis-oxazolines. The results indicate that highly enantioselective aziridination of chalcones with up to >99% ee have been achieved under catalysis of (S,S)-1,2-bis[(S)-(4-phenyl)oxazolin-2-yl] cyclohexane, which is the most-matched stereoisomer among cyclohexane-linked bis-oxazolines. It was also found that the enantioselectivity is not substituent-dependent with respect to chalcones in the present case, unlike with 1,8-anthracene-linked bis-oxazolines (AnBOXes).

Synthesis of new C2-symmetrical diphosphines using chiral zinc organometallics

The new C2-symmetrical diphosphines 1-4 of potential interest for asymmetric catalysis were prepared in protected form by a convergent synthesis based on the use of readily available (S,S)-1,2-cyclohexanedicarboxylic acid 8 and the phosphorus reagent (Et2N)2PLi·BH3.