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
F: 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

L-Phenylglycine

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View Lastest Price from DL-10-CAMPHORSULFONIC ACID manufacturers

Wuhan Circle Star Chem-medical Technology Co.,Ltd

Product: DL-10-CAMPHORSULFONIC ACID 5872-08-2
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 98
Supply Ability: 1000
Release date: 2024-12-25

Hebei Zhuanglai Chemical Trading Co.,Ltd

Product: DL-Camphorsulfonic Acid 5872-08-2
Price: US $120.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 20ton
Release date: 2024-05-06

Hebei Weibang Biotechnology Co., Ltd

Product: DL-10-CAMPHORSULFONIC ACID 5872-08-2
Price: US $10.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 10 mt
Release date: 2024-11-20

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

(1R)-(-)-10-Camphorsulfonic acid (1S)-(+)-Camphor-10-sulphonic acid rac 5-Desfluoro Voriconazole ent-Voriconazole 4-Ethyl-5-fluoropyrimidine methyl N,N,N-trimethyl-4-[(4,7,7-trimethyl-3-oxobicyclo[2.2.1]hept-2-ylidene)methyl]anilinium sulphate 6-(1-Bromoethyl)-4-chloro-5-fluoropyrimidine Pyrimidine, 4-chloro-6-(1,1-dibromoethyl)-5-fluoro- Voriconazole Impurity 53 (2R,3S/2S,3R)-3-(4-Chloro-5-fluoro-6-pyrimidinyl)-2-(2,4-difluorophenyl)butan-2-ol hydrochloride Voriconazole Impurity 8 BGPPSFHHAYWTMX-LRDDRELGSA-N Voriconazole (2R,3R)-Isomer Voriconazole Impurity 18 1H-1,2,3-Triazole-4-methanol, 1-[(2,6-difluorophenyl)methyl]- 1,2,4-Triazole 2,2'-Azobis(2-methylpropionitrile) Voriconazole Impurity 51

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)

(7,7-dimethyl-2-oxo-norbornan-1-yl)methanesulfonic acid

Carbadox Impurity 5

5872-08-2

5872/8/2

5872-8-2

C10H16O4SH2O