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282146

Sigma-Aldrich

(1R)-(−)-10-Camphorsulfonic acid

98%

Synonym(s):

(−)-Camphor-10-sulfonic acid, (1R)-(−)-Camphor-10-sulfonic acid, (1R)-Camphor-10-sulfonic acid

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About This Item

Empirical Formula (Hill Notation):
C10H16O4S
CAS Number:
35963-20-3
Molecular Weight:
232.30
Beilstein:
2809676
EC Number:
252-817-9
MDL number:
MFCD00064158
UNSPSC Code:
12352106
PubChem Substance ID:
24857020
NACRES:
NA.22

Assay

98%

optical activity

[α]20/D −21°, c = 2 in H2O

mp

198 °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-/m0/s1

InChI key

MIOPJNTWMNEORI-XVKPBYJWSA-N

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General description

(1R)-(−)-10-Camphorsulfonic acid is an HPLC derivatization reagent for UV/Vis detection. It is mainly employed for the resolution of bases.

Application

(1R)-(−)-10-Camphorsulfonic acid may be used as a chiral building block for the synthesis of pentavalent organo-bismuth derivatives by enantioselective C-arylation. It may be used as a chiral monomer in the enantioselective sensing of chiral amino acids by potentiometric sensors based on optical active polyaniline films.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - 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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(+)-(2R, 8aS)-10-(Camphorylsulfonyl) Oxaziridine.
Towson JC, et al
Organic Syntheses, 158-158 (1993)
Synthesis and reactivity of chiral pentavalent bismuth derivatives
Finet PJ and Fedorov YA
Russian Chemical Bulletin, 53(7), 1488-1495 (2004)
Chen Liu et al.
Organic letters, 13(10), 2638-2641 (2011-04-23)
A novel ion pair catalyst containing a chiral counteranion can be readily derived by simply mixing cinchona alkaloid-derived diamine with chiral camphorsulfonic acid (CSA). A mixture of 9-amino(9-deoxy)epi-quinine 8 and (-)-CSA was found to be the best catalyst with matching
Bala Kishan Gorityala et al.
Bioorganic & medicinal chemistry letters, 19(11), 3093-3095 (2009-04-29)
A mild and efficient synthesis of pseudoglycosides has been developed using metal free (S)-camphorsulfonic acid. (S)-CSA acts as an excellent catalyst for conversion of 2,4,6-tri-O-acetyl-D-glucal to 2,3-unsaturated O-glycosides. A wide range of biologically active natural products, alcohols and thiols could
[D-camphor-beta-sulfonic acid as an ion-pair reagent for the determination of biogenic amines and their metabolites in the rat brain by reverse phase high performance liquid chromatography].
X R Xu et al.
Zhongguo yao li xue bao = Acta pharmacologica Sinica, 8(2), 113-117 (1987-03-01)
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