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DL-10-CAMPHORSULFONIC ACID

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CAS:5872-08-2
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Products Intro: Product Name:Camphorsulfonic acid
CAS:5872-08-2

Lastest Price from DL-10-CAMPHORSULFONIC ACID manufacturers

  • DL-Camphorsulfonic acid
  • US $15.00-10.00 / KG
  • 2021-07-13
  • CAS:5872-08-2
  • Min. Order: 1KG
  • Purity: 99%+ HPLC
  • Supply Ability: Monthly supply of 1 ton
  • DL-Camphorsulfonic acid
  • US $15.00-10.00 / KG
  • 2021-07-10
  • CAS:5872-08-2
  • Min. Order: 1KG
  • Purity: 99%+ HPLC
  • Supply Ability: Monthly supply of 1 ton
DL-10-CAMPHORSULFONIC ACID Basic information
Overview Preparation Resolution Uses Market References
Product Name:DL-10-CAMPHORSULFONIC ACID
Synonyms:DL-10-CAMPHORSULPHONIC ACID;DL-10-CAMPHORSULFONIC ACID;DL-10-CAMPHORSULFONIC ACID N-HYDRATE;D-(+)-10-CAMPHORSULFONIC ACID MONOHYDRATE;(+/-)-CAMPHOR-10-SULPHONIC ACID;(+/-)-CAMPHOR-10-SULFONIC ACID (BETA);(+/-)-CAMPHOR-10-SULFONIC ACID;CAMPHOR-10-SULFONIC ACID
CAS:5872-08-2
MF:C10H16O4S
MW:232.3
EINECS:227-527-0
Product Categories:Organic AcidsOrganic Conductors and Photovoltaics: OFET and OPV Materials;Chemical Synthesis;Bicyclic Monoterpenes;Conducting Polymers and Monomers;Polyanilines and Polyaniline Dopants;Synthetic Reagents;Pharmaceutical Intermediates;FINE Chemical & INTERMEDIATES;Biochemistry;Reagents for Oligosaccharide Synthesis;Terpenes;VX:15689727968
Mol File:5872-08-2.mol
DL-10-CAMPHORSULFONIC ACID Structure
DL-10-CAMPHORSULFONIC ACID Chemical Properties
Melting point 203-206 °C (dec.)(lit.)
Boiling point 344.46°C (rough estimate)
alpha [α]D20 0.0±0.3° (c=5, H2O)
density 1.2981 (rough estimate)
refractive index 1.5400 (estimate)
storage temp. 2-8°C
form Granular Powder
pka1.17±0.50(Predicted)
color Slightly beige
Water Solubility Soluble in water.
Sensitive Hygroscopic
BRN 3205973
Stability:Stable. Incompatible with strong bases, strong oxidizing agents. Combustible.
InChIKeyMIOPJNTWMNEORI-UHFFFAOYSA-N
CAS DataBase Reference5872-08-2(CAS DataBase Reference)
EPA Substance Registry SystemBicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo- (5872-08-2)
Safety Information
Hazard Codes C
Risk Statements 34
Safety Statements 26-36/37/39-45-27
RIDADR UN 3261 8/PG 2
WGK Germany 3
RTECS DT5077100
3-10
TSCA Yes
HazardClass 8
PackingGroup III
HS Code 29147000
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
DL-10-CAMPHORSULFONIC ACID Usage And Synthesis
OverviewDL-Camphorsulfonic acid, also known as camphorsulfonic acid, is a white or almost white crystalline powder. The molecular formula of camphorsulfonic acid is C10H16O4S. It is a pair of chiral optical enantiomers with prismatic crystals, divided into left-handed camphorsulfonic acid and right-handed camphorsulfonic acid. The melting point is 193~195 ℃ and 197~200 ℃, respectively. Camphorsulfonic acid is a derivative of camphor, widely used in medicine, light industry and cosmetic industry. At present, its application mainly focused on chiral asymmetric synthesis, high selective catalysis of natural products and polymer doping with polyaniline to prepare nano-scale conductive polymer materials.
left-right isomer of camphorsulfonic acid
Figure 1: left-right isomer of camphorsulfonic acid
Preparationnatural camphor is mainly extracted from camphor plants, ginger plants and sage seeds, and with optical activity; synthetic camphor is generally prepared by the isomerization of turpentine to obtain camphene, then by esterification, hydrolysis and dehydrogenation reaction process; synthetic camphor is racemic, almost lacking optical activity. Through the reaction of camphor powder and concentrated sulfuric acid sulfonation, racemic camphorsulfonic acid is obtained, and then by the resolution, left and right handed camphorsulfonic acid is made. The optimum conditions for the synthesis of camphorsulfonic acid are as follows: the molar ratio of camphor powder, concentrated sulfuric acid and acetic anhydride is 1.0: 1.4: 3.0; reaction temperature is10 ℃; standing time is 5 days, and camphorsulfonic acid is vacuum dried. Utilizing sopropyl alcohol as solvent, camphor sulfonate is obtained by neutralization of camphorsulfonic acid and a resolving agent made by alcohol amine; camphorsulfonic acid is obtained by purification.
Preparation principle
Figure 2: Preparation principle
ResolutionKinetic resolution is the selective chiral reduction of racemic camphor, so that one of the enantiomers of racemates is selectively reducted, leaving the required isomers, and then purifying. It is also possible to add optically active amino acids, phenylglycine, phenylalanine, hydroxyphenylglycine, o-chlorophenylglycine and resolving agents of its derivatives. Subjecting racemic camphorsulfonic acid to salting treatment, separating the left and right camphorsulfonic acid ammonium salt solution by chromatography, film evaporation, crystallization and filtration; drying to get white crystals, the left and right handed camphorsulfonic acid is made.
UsesPharmaceutical intermediates, optical split agent. Camphorsulfonic acid is an important organic synthesis intermediates, optical resolving agent. Due to its optical rotation, it is industrially applicable be the optical isomers for racemisation, and is also widely used as pharmaceutical intermediates such as for the production of intestinal disorder inhibitors, HIV improving agents and the like. Left and right handed camphorsulfonic acid is an important resolving agent for optically active amino acids, such as camphorsulfonic acid—a chiral ion-pairing reagent. It separates 5 substances—phenylpropanolamine, which has receptor-blocking action and cardiac inhibition and local anesthetic action effects; metoprolol, propranolol, epinephrine, salbutamol and atenolol.
Camphor sulfonate made by camphorsulfonic acid for salting or other synthetic routes also has a wide range of uses. For example, camphor sulfonate is a veterinary central stimulant, which can stimulate the respiratory center and cause respiratory excitement, ; it is used for the treatment respiratory and circulatory acute disorders, resisting central nervous system poisoning; camphor ammonium sulfonate acts as a chiral ion pair reagent added to the mobile phase to separate the aromatic alcohol amine drug enantiomers.
Camphor sulfonate
Figure 3: Camphor sulfonate
MarketThe domestic demand for camphorsulfonic acid is high; camphorsulfonic acid is basically dependent on imports, and the price of it is also very expensive, especially for L-camphorsulfonic acid.
References[1] KE Chunlan, LIU Xiaohong, XU Chunxiao etc. Synthesis and Resolution of Camphor Sulfonic Acid [J]. Journal of Nanchang University Engineering, 2010, 32 (4): 381-384.
[2] KE Chunlan, LIU Xiaohong, XU Chunxiao etc. Synthesis and latest application of chiral camphorsulfonic acid and its salts [J] .Jiangxi Chemical Industry, 2010 (2): 1-4.
Chemical PropertiesDL-10-CAMPHORSULFONIC ACID is white to off-white powder
DL-10-CAMPHORSULFONIC ACID Preparation Products And Raw materials
Preparation ProductsL-Phenylglycine
Tag:DL-10-CAMPHORSULFONIC ACID(5872-08-2) Related Product Information
D-Camphorsulfonic acid DL-Camphor 4,5-Dimethyl-1H-imidazol-2-amine hydrochloride (+)-3-BROMOCAMPHOR-10-SULFONIC ACID HYDR 2-(S)-(2-HYDROXYETHYL)PIPERIDINE-(S)-10-CAMPHORSULPHONATE DL-OXO-10-BORNANESULFONIC ACID CALCIUM SALT Sodium (+)-10-camphorsulfonate (S)-2-PIPERAZINE CARBOXYLIC ACID DI(S)-CAMPHORSULFONIC ACID SALT BENZENEACETIC ACID, 2-CHLORO-A-[[2-(2-THIENYL)ETHYL]AMINO]-, METHYL ESTER, (+)-, (1S)-7,7-DIMETHYL-2-OXOBICYCLO[2.2.1]HEPTANE-1-METHANESULFONATE L-10-CAMPHORSULFONIC ACID AMMONIUM SALT (1S)-2-oxobornane-10-sulphonic acid, compound with 7-[2-(diethylamino)ethyl]-3,7-dihydro-1,3-dimethyl-1H-purine-2,6-dione (1:1) DL-10-CAMPHORSULFONIC ACID CALCIUM SALT CAMPHORQUINONE-10-SULFONIC ACID, HYDRATE [(3E)-3-[[4-[(Z)-[7,7-dimethyl-3-oxo-4-(sulfomethyl)norbornan-2-yliden e]methyl]phenyl]methylidene]-7,7-dimethyl-2-oxo-norbornan-1-yl]methane sulfonic acid D(+)-AMMONIUM-ALPHA-BROMOCAMPHOR-10-SULFONATE (2S,3S)-4-BROMO-CIS-2,3-EPOXYBUTYL (1S)- 10-CAMPHORSULFONATE L-Camphor-10-suLphonic acid (-)-CAMPHOR-10-SULFONIC ACID AMMONIUM SALT