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147923

Sigma-Aldrich

Camphor-10-sulfonic acid (β)

98%

Synonym(s):

CSA

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About This Item

Empirical Formula (Hill Notation):
C10H16O4S
CAS Number:
5872-08-2
Molecular Weight:
232.30
Beilstein:
3205973
EC Number:
227-527-0
MDL number:
MFCD00074827
UNSPSC Code:
12352106
PubChem Substance ID:
24848866
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

200

Assay

98%

form

solid

mp

203-206 °C (dec.) (lit.)

functional group

ketone
sulfonic acid

SMILES string

[H][C@@]12CC[C@@](CS(O)(=O)=O)(C(=O)C1)C2(C)C

InChI

1S/C10H16O4S/c1-9(2)7-3-4-10(9,8(11)5-7)6-15(12,13)14/h7H,3-6H2,1-2H3,(H,12,13,14)/t7-,10-/m1/s1

InChI key

MIOPJNTWMNEORI-GMSGAONNSA-N

General description

Camphorsulfonic acid is a organosulphur compound.

Application

Camphor-10-sulfonic acid (β) (CSA) is extensively used as an acid catalyst.[1]
  • It can be used in a catalytic amount to protect hydroxyl groups as tetrahydropyranyl (THP) ethers using dihydropyran.[2]
  • It also catalyzes the protection of ketones as ketals.[3]
  • It is a useful catalyst for the intramolecular ring opening of epoxides.[4]
  • CSA can also be used to catalyze nucleophile-promoted alkyne-iminium cyclization in the total synthesis of pumiliotoxin A.[5]

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000382220
BCCM3886
0000353651
0000382220
0000238686

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Sigma-Aldrich

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10?Camphorsulfonic Acid.
Leahy E M
e-EROS Encyclopedia of Reagents for Organic Synthesis. null
Activation of 6-endo over 5-exo hydroxy epoxide openings. Stereoselective and ring selective synthesis of tetrahydrofuran and tetrahydropyran systems.
Nicolaou K C, et al.
Journal of the American Chemical Society, 111(14), 5330-5334 (1989)
A total synthesis of (+)-pisiferol.
Tamai Y, et al.
Journal of the Chemical Society. Perkin Transactions 1, 1311-1315 (1986)
Conducting Polyaniline-Electrical Charge Transportation
Babu VJ, et al.
Materials Sciences and Applications, 4(1-10) (2013)
Enantioselective total synthesis of the pumiliotoxin a alkaloids via reductive iminium ion-alkyne cyclizations. Total synthesis of (+)-pumiliotoxin a.
Overman L E and Sharp M J
Tetrahedron Letters, 29(8), 901-904 (1988)
View All Related Papers

Questions

  1. Does product 147923, Camphor-10-sulfonic acid (β), consist of a racemic mixture of R and S camphor-10-sulphonic acid?

    1 answer

    1. This is a racemic mixture.

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