(1S,3R)-1,2,2-TRIMETHYL-1,3-CYCLOPENTANEDICARBOXYLIC ACID

Base Information

• Chemical Name: (1S,3R)-1,2,2-TRIMETHYL-1,3-CYCLOPENTANEDICARBOXYLIC ACID
• CAS No.: 560-09-8
• Molecular Formula: C10H16 O4
• Molecular Weight: 200.235
• Hs Code.: 2942000000
• European Community (EC) Number: 811-021-7
• NSC Number: 60219,824
• UNII: 62F72U898F
• DSSTox Substance ID: DTXSID80204569
• Nikkaji Number: J184.557H
• Wikipedia: Camphoric_acid
• Mol file: 560-09-8.mol

Synonyms:1,3-Cyclopentanedicarboxylicacid, 1,2,2-trimethyl-, (1S-cis)-; Camphoric acid, cis-(-)- (8CI); (-)-Camphoricacid; (-)-cis-Camphoric acid; (1S,3R)-(-)-Camphoric acid; (1S,3R)-Camphoricacid; L-Camphoric acid; l-Camphoric acid

Chemical Property of (1S,3R)-1,2,2-TRIMETHYL-1,3-CYCLOPENTANEDICARBOXYLIC ACID

Chemical Property:

• Vapor Pressure: 0.000119mmHg at 25°C
• Melting Point: 188-190 °C(lit.)
• Boiling Point: 312°Cat760mmHg
• PKA: 4.57±0.60(Predicted)
• Flash Point: 156.7°C
• PSA: 74.60000
• Density: 1.177g/cm³
• LogP: 1.59810
• Storage Temp.: Refrigerator
• Solubility.: DMSO, Ethanol, Methanol
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 200.10485899
• Heavy Atom Count: 14
• Complexity: 282

Purity/Quality:

≥98% ^*data from raw suppliers

(1S,3R)-(?)-Camphoric acid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(CCC1(C)C(=O)O)C(=O)O)C
• Isomeric SMILES: C[C@@]1(CC[C@H](C1(C)C)C(=O)O)C(=O)O
• Uses: (1S,3R)-(?)-Camphoric acid can be used:As an enantiomeric linker in the preparation of chiral surface-anchored metal-organic frameworks (MOFs).To prepare porous MOFs having multifunctional properties; used in gas adsorption and separation of racemic alcohols.To prepare a cobalt(II) coordination polymer named {Co(phen)(H2O)[C8H14(COO)2]}n·(CH3OH)n , wherein “phen” is 1,10-phenanthroline and C8H14(COOH)2 is [(1S,3R)-camphoric acid.

Technology Process of (1S,3R)-1,2,2-TRIMETHYL-1,3-CYCLOPENTANEDICARBOXYLIC ACID

There total 10 articles about (1S,3R)-1,2,2-TRIMETHYL-1,3-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: 84.0%

(1S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione (2767-84-2) → (1S,3R)-(-)-camphoric acid (560-09-8)

Guidance literature:

With sodium percarbonate; In water; acetone; at 65 ℃; for 0.166667h; other α-diketones, var. time;

DOI:10.1080/00397919308018595

Reference yield:

(-)-(1S,3R,4R)-3-bromocamphor (64474-54-0) → (1S,3R)-(-)-camphoric acid (560-09-8) + (1S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione (2767-84-2)

Guidance literature:

(-)-(1S,3R,4R)-3-bromocamphor; With air; potassium iodide; In dimethyl sulfoxide; at 150 ℃;

With sodium hydroxide; In water; Further stages.;

DOI:10.1007/s10600-007-0032-2

Reference yield:

endo-borneol (464-45-9) → (1S,3R)-(-)-camphoric acid (560-09-8)

Guidance literature:

With nitric acid; man loest in Natronlauge, aethert aus, faellt die alkal. Loesung mit Salzsaeure;

upstream raw materials:

endo-borneol

DL-camphoric acid

(1S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione

1,7,7-trimethylbicyclo[2.2.1]hept-2-ene

Downstream raw materials:

DL-camphoric acid

(1R,3S)-(+)-camphoric imide

(+)-(1S,3R)-1,2,2-trimethylcyclopentane-1,3-dicarboxylic anhydride

(1S,3R)-dimethyl 1,2,2-trimethylcyclopentane-1,3-dicarboxylate

Refernces

PHENYLCAMPHORIC ACID: STEREOCHEMISTRY AND EPIMERIZATION

10.1016/S0040-4039(00)81949-8

The research aimed to revise the stereochemistry of phenylcamphoric acid, a compound with a history of assigned structures and configurations since its first preparation in 1894. The researchers conducted difference NOE experiments and confirmed their new assignment through x-ray crystallography. They discovered that base treatment of methyl phenylcamphorate led to equilibration with its previously unknown epimer, methyl-epiphenylcamphorate. The study was motivated by the structural and stereochemical similarity of phenylcamphoric acid to B-necrodol, a terpenoid alcohol found in the defensive secretion of a carrion beetle, with the hope that the acid could serve as a synthetic precursor for B-necrodol.

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