(-)-Camphanic acid chloride

Base Information

• Chemical Name: (-)-Camphanic acid chloride
• CAS No.: 39637-74-6
• Molecular Formula: C10H13ClO3
• Molecular Weight: 216.664
• Hs Code.: 29322090
• European Community (EC) Number: 254-552-4
• DSSTox Substance ID: DTXSID60960257
• Nikkaji Number: J1.478.250H
• Wikidata: Q72515027
• Mol file: 39637-74-6.mol

Synonyms:2-Oxabicyclo[2.2.1]heptane-1-carbonylchloride, 4,7,7-trimethyl-3-oxo-, (1S)-;(-)-(1S)-Camphanoyl chloride;(-)-(1S,4R)-Camphanoyl chloride;(-)-(S)-Camphanyl chloride;(-)-Camphanic acidchloride;(-)-Camphanic chloride;(-)-Camphanylchloride;(1S)-(-)-Camphanic acid chloride;(1S)-(-)-Camphanic chloride;(1S)-(-)-Camphanoyl chloride;(1S)-(-)-Camphanylchloride;(1S)-(-)-w-Camphanic chloride;(1S)-Camphanoyl chloride;(1S,4R)-(-)-Camphanic acidchloride;(1S,4R)-w-Camphanoyl chloride;(S)-Camphanic acid chloride;(S)-Camphanoylchloride;

Chemical Property of (-)-Camphanic acid chloride

Chemical Property:

• Appearance/Colour: Off-white powder
• Vapor Pressure: 0.00119mmHg at 25°C
• Melting Point: 71-73 °C(lit.)
• Refractive Index: 1.52
• Boiling Point: 299.5 °C at 760 mmHg
• Flash Point: 125 °C
• PSA: 43.37000
• Density: 1.298 g/cm³
• LogP: 1.87370
• Storage Temp.: −20°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: decomposes
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 216.0553220
• Heavy Atom Count: 14
• Complexity: 336

Purity/Quality:

99% ^*data from raw suppliers

(-)-(1S,4R)-CamphanoylChloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C, Xi
• Hazard Codes: C,Xi
• Statements: 34-29
• Safety Statements: 26-36/37/39-45-8-27

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2(CCC1(OC2=O)C(=O)Cl)C)C
• Isomeric SMILES: C[C@@]12CC[C@@](C1(C)C)(OC2=O)C(=O)Cl
• Uses: An optically active resolving agent (1S)-(-)-Camphanic chloride is used as a resolving agent for alcohols as the diastereomeric esters by crystallization or chromatography and as a chiral derivatization reagent for determination of enantiomeric excess of alcohols and amines. (1S)-(-)-Camphanic chloride may be used in esterification of enantiomers in volatiles releasedf from wheat, in order to determine the proportion of enantiomers and also in quantifying the esters.

Technology Process of (-)-Camphanic acid chloride

There total 8 articles about (-)-Camphanic acid chloride 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: 99.0%

(-)-camphanic acid (67111-66-4,13429-83-9) → (1S)-(-)-camphanic chloride (39637-74-6)

Guidance literature:

With thionyl chloride; Reflux;

DOI:10.15227/orgsyn.071.0048

Reference yield: 94.0%

(-)-camphanic acid (67111-66-4,13429-83-9) → (-)-ω-camphanic acid chloride (39637-74-6,49620-91-9,104530-16-7)

Guidance literature:

With thionyl chloride; for 3h; Heating;

Reference yield:

D-(+)-camphoric acid (124-83-4) → (1S)-(-)-camphanic chloride (39637-74-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: phosphorus pentachloride / Cooling with ice

1.2: 12 h / 125 °C

2.1: sulfuric acid / Reflux

2.2: 110 °C

3.1: thionyl chloride / Reflux

With thionyl chloride; phosphorus pentachloride; sulfuric acid;

DOI:10.15227/orgsyn.071.0048

upstream raw materials:

(-)-camphanic acid

1,2,2-trimethyl-cyclopentane-1,3-dicarbonyl chloride

1-Bromo-5,8,8-trimethyl-3-oxa-bicyclo[3.2.1]octane-2,4-dione

(+)-camphoric acid

Downstream raw materials:

(1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid ((1S,2S)-2-hydroxy-1,2-diphenyl-ethyl)-amide

(1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid ((1R,2R)-2-hydroxy-1,2-diphenyl-ethyl)-amide

(4S)-N-<4-(difluoromethoxy)phenyl>-4-(4-fluorophenyl)-N-<(1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo<2.2.1>hept-1-ylcarbonyl>-3-<4-(2,2,2-trifluoroethoxy)phenyl>-4,5-dihydropyrazole-1-carboxamide

(4R)-N-<4-(difluoromethoxy)phenyl>-4-(4-fluorophenyl)-N-<(1S,4R)-4,7,7-trimethyl-3-oxo-2-oxabicyclo<2.2.1>hept-1-ylcarbonyl>-3-<4-(2,2,2-trifluoroethoxy)phenyl>-4,5-dihydropyrazole-1-carboxamide

Refernces

• 1、 Zheng, Lu,Zheng, Dan,Wang, Yanru,Yu, Chengyuan,Zhang, Kun,Jiang, Hua. "Chiral bisphosphine ligands based on quinoline oligoamide foldamers: application in asymmetric hydrogenation". supporting information. p. 9573 - 9577. Retrieved 2019/11/20.
• 2、 Lo, Brian,Lam, Sarah,Wong, Wing-Tak,Chiu, Pauline. "Asymmetric (4+3) cycloadditions of enantiomerically enriched epoxy enolsilanes". supporting information. p. 12120 - 12123. Retrieved 2013/01/16.