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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

Assay

98%

form

solid

mp

203-206 °C (dec.) (lit.)

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.
  • It can be used in a catalytic amount to protect hydroxyl groups as tetrahydropyranyl (THP) ethers using dihydropyran.
  • It also catalyzes the protection of ketones as ketals.
  • It is a useful catalyst for the intramolecular ring opening of epoxides.
  • CSA can also be used to catalyze nucleophile-promoted alkyne-iminium cyclization in the total synthesis of pumiliotoxin A.

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
10?Camphorsulfonic Acid.
Leahy E M
e-EROS Encyclopedia of Reagents for Organic Synthesis. null
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)
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