All Photos(3)

147923

Sigma-Aldrich

Camphor-10-sulfonic acid (β)

98%

Synonym(s):
CSA
Empirical Formula (Hill Notation):
C10H16O4S
CAS Number:
Molecular Weight:
232.30
Beilstein:
3205973
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

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.

Packaging

100, 500 g in glass bottle

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

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

Certificate of Analysis

Certificate of Origin

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)
Conducting Polyaniline-Electrical Charge Transportation
Babu VJ, et al.
Materials Sciences and Applications, 4(1-10) (2013)
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)
Chemistry of amphotericin B. Degradation studies and preparation of amphoteronolide B.
Nicolaou K C, et al.
Journal of the American Chemical Society, 110(14), 4660-4672 (1988)

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