Overview Preparation Resolution Uses Market References
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DL-10-CAMPHORSULFONIC ACID

Overview Preparation Resolution Uses Market References
Product Name
DL-10-CAMPHORSULFONIC ACID
CAS No.
5872-08-2
Chemical Name
DL-10-CAMPHORSULFONIC ACID
Synonyms
CAMPHOR-10-SULFONIC ACID;10-CAMPHORSULFONIC ACID;DL-CAMPHORSULFONIC ACID;((1R,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonic acid;DL-10-CAMPHORSULPHONIC ACID;(+/-)-CSA;¥1,450,959.00;(+/-)-10-CamphorsuL;Carbadox Impurity 5;ChaMphorsulfonic acid
CBNumber
CB4408868
Molecular Formula
C10H16O4S
Formula Weight
232.3
MOL File
5872-08-2.mol
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DL-10-CAMPHORSULFONIC ACID Property

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
pka
1.17±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.
InChIKey
MIOPJNTWMNEORI-UHFFFAOYSA-N
CAS DataBase Reference
5872-08-2(CAS DataBase Reference)
EPA Substance Registry System
Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo- (5872-08-2)
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
147923
Product name
Camphor-10-sulfonic acid (β)
Purity
98%
Packaging
100g
Price
$71.9
Updated
2024/03/01
Sigma-Aldrich
Product number
147923
Product name
Camphor-10-sulfonic acid (β)
Purity
98%
Packaging
500g
Price
$177
Updated
2024/03/01
TCI Chemical
Product number
C0016
Product name
(+/-)-10-Camphorsulfonic Acid
Purity
>98.0%(T)
Packaging
25g
Price
$23
Updated
2024/03/01
TCI Chemical
Product number
C0016
Product name
(+/-)-10-Camphorsulfonic Acid
Purity
>98.0%(T)
Packaging
100g
Price
$42
Updated
2024/03/01
Alfa Aesar
Product number
A12620
Product name
(±)-Camphor-10-sulfonic acid, 98%
Packaging
100g
Price
$47.2
Updated
2024/03/01
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DL-10-CAMPHORSULFONIC ACID Chemical Properties,Usage,Production

Overview

DL-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.

Figure 1: left-right isomer of camphorsulfonic acid

Preparation

natural 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.

Figure 2: Preparation principle

Resolution

Kinetic 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.

Uses

Pharmaceutical 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.

Figure 3: Camphor sulfonate

Market

The 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 Properties

DL-10-CAMPHORSULFONIC ACID is white to off-white powder

Uses

(+)-Camphor-10-sulfonic acid is used as a resolving agent for chiral amines and other cations. It is involved in the preparation of active pharmaceutical ingredient such as trimetaphan camsilate, which is used to reduce bleeding during neurosurgery. Further, it is involved in the transglucosidation of methyl and ethyl D-glucopyranosides by alcoholysis.

Definition

ChEBI: Camphorsulfonic acid is a sulfonic acid containing the camphorsulfonate anion. It is functionally related to a camphor. It is a conjugate acid of a camphorsulfonate anion.

General Description

Camphorsulfonic acid is a organosulphur compound.

DL-10-CAMPHORSULFONIC ACID Preparation Products And Raw materials

Raw materials

Preparation Products

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DL-10-CAMPHORSULFONIC ACID Suppliers

TCI Europe
Tel
320-37350700
Fax
+32 (0)37350701
Email
sales@tcieurope.eu
Country
Europe
ProdList
23680
Advantage
75
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View Lastest Price from DL-10-CAMPHORSULFONIC ACID manufacturers

Hebei Yime New Material Technology Co., Ltd.
Product
DL-10-CAMPHORSULFONIC ACID 5872-08-2
Price
US $100.00-95.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
EX:20T
Release date
2023-03-03
Hebei Yibangte Import and Export Co. , Ltd.
Product
DL-10-CAMPHORSULFONIC ACID 5872-08-2
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
50000kg
Release date
2023-11-07
Hebei Mojin Biotechnology Co., Ltd
Product
DL-10-CAMPHORSULFONIC ACID 5872-08-2
Price
US $0.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
50000KG/month
Release date
2023-06-21

5872-08-2, DL-10-CAMPHORSULFONIC ACIDRelated Search:


  • 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
  • 7-dimethyl-2-oxo-(+/-)-bicyclo[2.2.1]heptane-1-methanesulfonicaci
  • D,L-Camphor sulphonic acid
  • (±)-Camphor-10-sulfonicacid,98%
  • Bicyclo2.2.1heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-
  • (n)-camphor-10-sulfonic acid
  • Campho 10 Sulphonic Acid
  • DL-6-oxobornane-10-sulphonic acid
  • ((1R,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonic acid
  • (7,7-dimethyl-3-oxoniumylidene-4-bicyclo[2.2.1]heptanyl)methanesulfonate
  • Voriconazole Impurity 19(Voriconazole EP Impurity E)
  • (+/-)-10-CamphorsuL
  • DL-OXO-10-BORNANESULFONIC ACID
  • DL-CAMPHOR-10-SULFONIC ACID
  • DL-CAMPHORSULFONIC ACID
  • (+/-)-10-CAMPHORSULFONIC ACID
  • 10-CAMPHORSULFONIC ACID
  • (±)-Camphor-10-sulfonate
  • (+-)-10-camphorsulphonic acid
  • DL-10-Camphorsulfonic acid,98%
  • D-(+)-10-Camphorsulfonic acid
  • Ecamsule Related Compound D (50 mg) (((1SR,4RS)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonic acid)
  • Voriconazole Related Compound F (50 mg) ({(1RS,4SR)-7,7-Dimethyl-2-oxobicyclo[2.2.1]hept-1-yl}methanesulphonic acid)
  • DL-CaMphor-10-sulphonic acid
  • DL-10-CaMphorsulfonic acid, 98% 500GR
  • ChaMphorsulfonic acid
  • Voriconazole IMpurity E
  • EcaMsule Related CoMpound D
  • DL- caMphor sulfonic acid (DL-caMphor sulfonic acid)
  • (+/-)-10-CaMphorsulfonic Acid, 98.0%(T)
  • ¥1,450,959.00
  • DL-10-Camphorsulfonic acid,99%
  • Voriconazole impurity E CRS
  • Voriconazole EP Impurity E (Voriconazole USP Related Compound F)
  • DL-10-CamphorsulfonicAci
  • (+/-)-CSA
  • Mixed camphor sulfonic acid
  • Voriconazole Impurity 31
  • DL-10-CAMPHORSULFONIC ACID/Voriconazole imp-E
  • (±)-1-Camphorsulfonic Acid
  • DL-10-CAMPHORSULFONIC
  • Voriconazole Related Compound F ({(1RS,4SR)-7,7-Dimethyl-2-oxobicyclo[2.2.1]hept-1-yl}methanesulpho (1718063)
  • Ecamsule USP Related Compound D
  • Voriconazole USP Related Compound F
  • Voriconazole Impurity 25 (Voriconazole EP Impurity E)
  • Carbadox Impurity 5
  • 5872-08-2
  • 5872/8/2
  • 5872-8-2
  • C10H16O4SH2O
  • Terpenes