1,2-Cyclopentanedicarboxylic acid

Base Information

• Chemical Name: 1,2-Cyclopentanedicarboxylic acid
• CAS No.: 21917-20-4
• Deprecated CAS: 80656-14-0
• Molecular Formula: C7H10 O4
• Molecular Weight: 158.154
• European Community (EC) Number: 633-363-4
• NSC Number: 139994
• DSSTox Substance ID: DTXSID40944515
• Nikkaji Number: J1.353.654F
• Mol file: 21917-20-4.mol

Synonyms:1,2-cyclopentanedicarboxylate;trans-1,2-cyclopentanedicarboxylate

Chemical Property of 1,2-Cyclopentanedicarboxylic acid

Chemical Property:

• Vapor Pressure: 8.88E-07mmHg at 25°C
• Boiling Point: 378.6°C at 760 mmHg
• Flash Point: 196.9°C
• PSA: 80.26000
• LogP: -2.09750
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 158.05790880
• Heavy Atom Count: 11
• Complexity: 167

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(C(C1)C(=O)O)C(=O)O

Technology Process of 1,2-Cyclopentanedicarboxylic acid

There total 19 articles about 1,2-Cyclopentanedicarboxylic 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: 95.0%

(1S,2S)-2-methoxycarbonylcyclopentane-1-carboxylic acid (111138-48-8) → (trans)-1,2-cyclopentanedicarboxylic acid (21917-20-4)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 4h;

DOI:10.1016/j.tetasy.2005.12.036

Reference yield: 83.0%

(-)-dimenthyl (1S,2S)-cyclopentane-1,2-dicarboxylate (96055-59-3) → (trans)-1,2-cyclopentanedicarboxylic acid (21917-20-4)

Guidance literature:

(-)-dimenthyl (1S,2S)-cyclopentane-1,2-dicarboxylate; With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20 ℃; for 5h;

With sodium hypochlorite; sodium chlorite; sodium phosphate buffer; 2,2,6,6-tetramethyl-piperidine-N-oxyl; In water; acetonitrile; at 35 ℃; for 9h;

DOI:10.1021/ol0348811

Reference yield: 78.0%

trans-(1S,2S)-cyclopentane-1,2-dicarboxylic acid dimethyl ester (80656-13-9) → (trans)-1,2-cyclopentanedicarboxylic acid (21917-20-4)

Guidance literature:

With sodium hydroxide; In methanol; water; Ambient temperature;

DOI:10.1021/ja00372a027

upstream raw materials:

trans-1,2-cyclopentanedicarboxylic acid

(1S,2S)-2-methoxycarbonylcyclopentane-1-carboxylic acid

trans-(1S,2S)-cyclopentane-1,2-dicarboxylic acid dimethyl ester

(2S,2'S)-1,1'-<(1S,2S)-cyclopentane-1,2-dicarbonyl>bis<1-<(tert-butoxy)carbonyl>-2-(tert-butyl)-5,5-dimethylimidazolidin-4-one>

Downstream raw materials:

Cyclopentan-1.2-trans-diamin

dimethyl cis-1,2-cyclopentanedicarboxylate

trans-(1S,2S)-cyclopentane-1,2-dicarboxylic acid dimethyl ester

cyclopentane-cis-1,2-dicarboxylic acid anhydride

Refernces

• 1、 Atodiresei, Iuliana,Schiffers, Ingo,Bolm, Carsten. "Asymmetric synthesis of chiral bisoxazolines and their use as ligands in metal catalysis". . p. 620 - 633. Retrieved 2007/10/03.
• 2、 Studer, Armido,Hintermann, Tobias,Seebach, Dieter. "Synthesis and First Applications of a New Chiral Auxiliary (tert-Butyl 2-(tert-Butyl)-5,5-dimethyl-4-oxoimidazolidine-1-carboxylate)". . p. 1185 - 1206. Retrieved 2007/10/02.