Title: d-Camphorsulfonic Acid
CAS Registry Number: 3144-16-9
CAS Name: 7,7-Dimethyl-2-oxobicyclo[2.2.1]heptane-1-methanesulfonic acid
Synonyms: 2-oxo-10-bornanesulfonic acid; 10-camphorsulfonic acid; camsylate; camphostyl; b-camphorsulfonic acid; Reychler's acid
Molecular Formula: C10H16O4S
Molecular Weight: 232.30
Percent Composition: C 51.70%, H 6.94%, O 27.55%, S 13.80%
Literature References: Prepn from powdered camphor, concd H2SO4 and acetic anhydride: Reychler,
Bull. Soc. Chim. Fr. [3]
19, 120 (1898); Armstrong, Lowry,
J. Chem. Soc. 81, 1447 (1902); Lipp, Knapp,
Ber. 73B, 915 (1940). Structure: Loudon,
J. Chem. Soc. 1933, 823; Komppa,
J. Prakt. Chem. 162, 19 (1943).
Properties: Prisms from glacial acetic acid or ethyl acetate, dec 193-195°. [a]D20 +43.5° (c = 4.3 in alcohol); [a]D20 +21.5° (c = 4.3 in water). Deliquesc in moist air. Practically insol in ether; slightly sol in glacial acetic acid, ethyl acetate.
Optical Rotation: [a]D20 +43.5° (c = 4.3 in alcohol); [a]D20 +21.5° (c = 4.3 in water)
Derivative Type: Ammonium salt
Molecular Formula: C10H19NO4S
Molecular Weight: 249.33
Percent Composition: C 48.17%, H 7.68%, N 5.62%, O 25.67%, S 12.86%
Properties: Needles from water. [a]D16 +20.5° (c = 5 in water). Very sol in water.
Optical Rotation: [a]D16 +20.5° (c = 5 in water)
Derivative Type: Potassium salt
Molecular Formula: C10H15KO4S
Molecular Weight: 270.39
Percent Composition: C 44.42%, H 5.59%, K 14.46%, O 23.67%, S 11.86%
Properties: Needles from alcohol. [a]D16 +18.4° (c = 4.4 in water).
Optical Rotation: [a]D16 +18.4° (c = 4.4 in water)
Use: Resolution of optically active isomers.
