147923
Camphor-10-sulfonic acid (β)
98%
Synonym(s):
CSA
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About This Item
Empirical Formula (Hill Notation):
C10H16O4S
CAS Number:
Molecular Weight:
232.30
UNSPSC Code:
12352106
NACRES:
NA.22
PubChem Substance ID:
EC Number:
227-527-0
Beilstein/REAXYS Number:
3205973
MDL number:
Product Name
Camphor-10-sulfonic acid (β), 98%
InChI key
MIOPJNTWMNEORI-GMSGAONNSA-N
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
SMILES string
[H][C@@]12CC[C@@](CS(O)(=O)=O)(C(=O)C1)C2(C)C
assay
98%
form
solid
mp
203-206 °C (dec.) (lit.)
functional group
ketone
sulfonic acid
Quality Level
Related Categories
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.
General description
Camphorsulfonic acid is a organosulphur compound.
signalword
Danger
hcodes
Hazard Classifications
Skin Corr. 1B
Storage Class
8A - Combustible corrosive hazardous materials
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
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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)
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)
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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