13429-83-9

Basic information

• Product Name: (1S)-(-)-Camphanic acid
• Synonyms: 4,7,7-Trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylic acid;(1S)-(-)-CAMPHANIC ACID;(1S)-3-OXO-4,7,7-TRIMETHYL-2-OXABICYCLO[2.2.1]HEPTANE-1-CARBOXYLIC ACID;(1R)-(-)-CAMPHANIC ACID;(S)-(-)-1-CAMPHANIC ACID;(−)-Camphanic acid;(1S)-4,7,7-Trimethyl-3-oxo-2-oxabicyclo[2.2.1]heptane-1-carboxylic acid;4,7,7-trimethyl(2-oxabicyclo[2.2.1]hept-1-yl)carboxylic acid
• CAS NO: 13429-83-9
• Molecular Formula: C₁₀H₁₄O₄
• Molecular Weight: 198.22
• EINECS: 236-552-6
• Product Categories: FINE Chemical & INTERMEDIATES;Chemical intermediate for Efavirenz;Miscellaneous Natural Products;API intermediates;Analytical Chemistry;Bicyclic Monoterpenes;Biochemistry;e.e. / Absolute Configuration Determination (NMR);Enantiomer Excess & Absolute Configuration Determination;Terpenes;Chiral Compound
• Mol File: 13429-83-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 201-205 °C
• Boiling Point: 255.53°C (rough estimate)
• Flash Point: 142.124°C
• Appearance: white to slightly beige crystalline powder
• Density: 1.0143 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.4500 (estimate)
• Storage Temp.: Store below +30°C.
• PKA: 3.36±0.60(Predicted)
• BRN: 84570
• CAS DataBase Reference: (1S)-(-)-Camphanic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1S)-(-)-Camphanic acid(13429-83-9)
• EPA Substance Registry System: (1S)-(-)-Camphanic acid(13429-83-9)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 22-24/25-37/39-26-36-37
• WGK Germany: 3
• Hazardous Substances Data: 13429-83-9(Hazardous Substances Data)

Usage

Description

(1S)-(-)-Camphanic acid, a white to slightly beige crystalline powder, is a versatile organic compound known for its applications in the synthesis of various chemicals and pharmaceuticals. It is commonly used as a chiral auxiliary for the separation of racemates, which is crucial in the production of enantiomerically pure compounds.

Uses

Used in Pharmaceutical Industry:
(1S)-(-)-Camphanic acid is used as a chiral auxiliary for the separation of racemates, which is essential in the production of enantiomerically pure compounds. This application is particularly important in the development of single-enantiomer drugs, as the different enantiomers of a drug can have significantly different pharmacological effects.
Used in Chemical Synthesis:
(1S)-(-)-Camphanic acid is used in the preparation of (-)-(1S,4R)-camphanoyl chloride by reacting with thionyl chloride. (1S)-(-)-Camphanic acid is an important intermediate in the synthesis of various chemicals and pharmaceuticals, showcasing the versatility of (1S)-(-)-Camphanic acid in different chemical reactions.

Purification Methods

Dissolve it in CH2Cl2, dry (MgSO4), filter, evaporate and the residue is sublimed at 120o/0.5mm or 140o/1mm. [Gerlach Helv Chim Acta 61 2773 1978, Beilstein 18/8 V 101.]

InChI:InChI=1/C10H14O4/c1-8(2)9(3)4-5-10(8,6(11)12)14-7(9)13/h4-5H2,1-3H3,(H,11,12)/t9?,10-/m0/s1

Upstream product

• 39637-74-6 (1S)-(-)-camphanic chloride 
• 432036-82-3 (-)-(1S,4R)-camphanic acid [((2R)-5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methyl]ester 
• 432036-81-2 (-)-(1S,4R)-camphanic acid [(5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methyl]ester 
• 48138-74-5 1,2,2-trimethyl-cyclopentane-1,3-dicarbonyl chloride 
• 87859-83-4 α-chlorocamphoric acid dichloride 
• 124-83-4 D-(+)-camphoric acid 
• 88701-62-6 1-(Cyanovinyl) (1'S)-camphanate 
• 87859-84-5 (-)-(1R,3R)-3-chlorocamphoric anhydride 
• 88764-13-0 (1R,2R,4R)-2-exo-cyano-7-oxabicyclo<2.2.1>hept-5-en-2-endo-yl(1S)-camphanate 
• 10333-96-7 1-Bromo-5,8,8-trimethyl-3-oxa-bicyclo[3.2.1]octane-2,4-dione 
• 124-83-4 (+)-camphoric acid 

Downstream Products

• 133098-41-6 4'-N-camphanyl-(4'R)-<4-2H1>-3,5'-O-dibenzylpyridoxamine 
• 133008-70-5 4'-N-camphanyl-(4'S)-<4-2H1>-3,5'-O-dibenzylpyridoxamine 
• 133008-61-4 (4'R)-<4'-2H1>-3,5'-O-dibenzylpyridox-4'-yl camphanate 
• 133098-40-5 (4'S)-<4'-2H1>-3,5'-O-dibenzylpyridox-4'-yl camphanate 
• 142696-11-5 (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid 1-[(R)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-phenyl-propionyl]-1H-pyrrol-2-ylmethyl ester 
• 142597-20-4 (1S,4R)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid 1-[(S)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-phenyl-propionyl]-1H-pyrrol-2-ylmethyl ester 
• 39637-74-6 (-)-ω-camphanic acid chloride 
• 432036-81-2 (-)-(1S,4R)-camphanic acid [(5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methyl]ester 
• 432036-82-3 (-)-(1S,4R)-camphanic acid [((2R)-5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methyl]ester 
• 432036-84-5 (-)-(1S,4R)-camphanic acid [((2S)-5-benzyloxy-2-hydroxy-1,2,3,4-tetrahydronaphth-2-yl)methyl]ester 
• 138403-92-6 (R)-Methoxy-phenyl-acetic acid (4bR,8aR,9R)-7-[1-ethoxycarbonyl-meth-(E)-ylidene]-2-methoxy-4b,5,6,7,8,8a,9,10-octahydro-phenanthren-9-yl ester 

Relevant articles and documents

182. The Preparation of Optically Pure 7-Oxabicyclohept-2-ene Derivatives. The CD Spectrum of (+)-(1R)-7-Oxabicyclohept-5-en-2-one

(-)-1-Camphanoyloxyacrylonitrile (=(-)-1-cyanovinyl camphanate; 1) obtained from the commercially available (-)-camphanoyl chloride and 2-oxopropiononitrile added to furan at 20 deg C in the presence of Cu(BF4)2*6H2O or ZnI2 and gave a mixture of 2-cyano-

METHOD FOR THE PREPARATION OF FUSED HETEROCYCLIC SUCCINIMIDE COMPOUNDS AND ANALOGS THEREOF

Fused cyclic compounds, methods of using such compounds in the treatment of nuclear hormone receptor-associated conditions such as cancer and immune disorders, and pharmaceutical compositions containing such compounds.

Preparation of (-)-(1S,4R)-Camphanoyl Chloride heptane-1-carbonyl Chloride, 4,7,7-Trimethyl-3-oxo, (1S)->

A convenient three step procedure for the preparation of (-)-(1S,4R)-camphanoyl chloride, starting from (+)-camphoric acid (A) via (-)-bromocamphoric anhydride (B) and (-)-camphanic acid (C) is described.