(1S,2S)-cyclohexane-1,2-dicarboxylic acid

Base Information

• Chemical Name: (1S,2S)-cyclohexane-1,2-dicarboxylic acid
• CAS No.: 21963-41-7
• Deprecated CAS: 610-10-6
• Molecular Formula: C₈H₁₂O₄
• Molecular Weight: 172.181
• Hs Code.: 2917209090
• European Community (EC) Number: 680-116-1
• DSSTox Substance ID: DTXSID20879215
• Nikkaji Number: J253.117H
• Wikidata: Q72459636
• Mol file: 21963-41-7.mol

Synonyms:21963-41-7;(1S,2S)-cyclohexane-1,2-dicarboxylic acid;(1S,2S)-1,2-Cyclohexanedicarboxylic Acid;1,2-Cyclohexanedicarboxylic acid, (1S,2S)-;1,2-Cyclohexanedicarboxylic acid, trans-;EINECS 218-975-8;AI3-18155;MFCD00001464;SCHEMBL150816;DTXSID20879215;MFCD00151258;NSC 31593;AKOS015833093;CS-W017609;DS-6642;1alpha,2beta-Cyclohexanedicarboxylic acid;AC-25529;(1S,2S)-cyclohexane-1,2-dicarboxylicacid;1,2-Cyclohexanedicarboxylicacid,(1S,2S)-;C1954;trans-1,2-Cyclohexanedicarboxylic acid, 95%;trans-(1s,2s)-1,2-cyclohexanedicarboxylic acid;(1S,2S)-(+)-CYCLOHEXANEDICARBOXYLIC ACID;1,2-Cyclohexanedicarboxylic acid, trans-(.+.)-;A878849;J-014375

Chemical Property of (1S,2S)-cyclohexane-1,2-dicarboxylic acid

Chemical Property:

• Melting Point: 184 °C
• Refractive Index: 18 ° (C=1, Acetone)
• Boiling Point: 384.1 °C at 760 mmHg
• PKA: 4.18±0.28(Predicted)
• Flash Point: 200.3 °C
• PSA: 74.60000
• Density: 1.314 g/cm³
• LogP: 0.96200
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Soluble in acetone(almost transparency).
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 172.07355886
• Heavy Atom Count: 12
• Complexity: 177

Purity/Quality:

98%,99%, ^*data from raw suppliers

(1S,2S)-1,2-Cyclohexanedicarboxylic Acid >98.0%(GC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(C(C1)C(=O)O)C(=O)O
• Isomeric SMILES: C1CC[C@@H]([C@H](C1)C(=O)O)C(=O)O
• Uses: A series of new C2-symmetric (1S,2S)-cyclohexane-1,2-dicarboxamides was synthesized from (1S,2S)-Cyclohexane-1,2-dicarboxylic acid.

Technology Process of (1S,2S)-cyclohexane-1,2-dicarboxylic acid

There total 6 articles about (1S,2S)-cyclohexane-1,2-dicarboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 19.0%

trans-1,2-cyclohexanedicarboxylic acid (2305-32-0) → (1S,2S)-cyclohexane-1,2-dicarboxylic acid (610-10-6,1687-30-5,2305-32-0,21963-41-7,46022-05-3,610-09-3)

Guidance literature:

With (S)-1-phenyl-ethylamine; In ethanol; toluene; Heating;

DOI:10.1021/jo051765y

Reference yield:

dimethyl cis-1,2-cyclohexanedicarboxylate (1687-29-2) → (1R,2R)-(-)-trans-cyclohexane-1,2-dicarboxylic acid (46022-05-3) + (1S,2S)-cyclohexane-1,2-dicarboxylic acid (610-10-6,1687-30-5,2305-32-0,21963-41-7,46022-05-3,610-09-3)

Guidance literature:

dimethyl cis-1,2-cyclohexanedicarboxylate; With sodium methylate; In methanol; for 4h; Inert atmosphere; Reflux;

With water; sodium hydroxide; at 75 ℃; for 4h; Inert atmosphere;

With hydrogenchloride; In water; at 0 - 5 ℃; pH=2; Optical yield = 16.399 %ee; diastereoselective reaction; Inert atmosphere;

DOI:10.1080/00397911.2015.1074695

Reference yield:

(-)-trans-1,2-cyclohexanedicarboxylic anhydride → (1S,2S)-cyclohexane-1,2-dicarboxylic acid (610-10-6,1687-30-5,2305-32-0,21963-41-7,46022-05-3,610-09-3)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane;

upstream raw materials:

trans-1,2-cyclohexanedicarboxylic acid

dimethyl cis-1,2-cyclohexanedicarboxylate

Downstream raw materials:

(1S,2S)-2-((S)-2-Hydroxy-1-phenyl-ethylcarbamoyl)-cyclohexanecarboxylic acid methyl ester

(1S,2S)-Cyclohexane-1,2-dicarboxylic acid bis-[((S)-2-hydroxy-1-phenyl-ethyl)-amide]

(1S,2S)-cyclohexane-1,2-dimethanol bis(methanesulfonate)

(1S,2S)-1,2-bis(diphenylphosphinomethyl)cyclohexane

Refernces

• 1、 Mueller, Christian E.,Zell, Daniela,Hrdina, Radim,Wende, Raffael C.,Wanka, Lukas,Schuler, Soeren M. M.,Schreiner, Peter R.. "Lipophilic oligopeptides for chemo- and enantioselective acyl transfer reactions onto alcohols". . p. 8465 - 8484. Retrieved 2013/09/24.
• 2、 Berkessel, Albrecht,Glaubitz, Katja,Lex, Johann. "Enantiomerically pure β-amino acids: A convenient access to both enantiomers of trans-2-aminocyclohexanecarboxylic acid". . p. 2948 - 2952. Retrieved 2007/10/03.