[(1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl]methanesulfonic acid

• ChemBase ID: 107738
• Molecular Formular: C10H16O4S
• Molecular Mass: 232.29664
• Monoisotopic Mass: 232.07692999
• SMILES: CC1(C)[C@@H]2CC[C@@]1(CS(=O)(=O)O)C(=O)C2
• Canonical SMILES: O=C1C[C@@H]2C([C@]1(CC2)CS(=O)(=O)O)(C)C
• InChI: 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
• InChIKey: MIOPJNTWMNEORI-GMSGAONNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl]methanesulfonic acid
• IUPAC Traditional name: (R)-camphorsulfonic acid
• Synonyms: (+)-CSA; (1S)-(+)-Camphor-10-sulfonic acid; (±)-β-Camphorsulfonic acid; (±)-Camphor-10-sulfonic acid; (+)-Camphor-10-sulfonic acid (β); (1S)-Camphor-10-sulfonic acid; (1S)-(+)-10-Camphorsulfonic acid; Camphor-10-sulfonic acid (β); (+)-β-Camphorsulfonic acid; (1S)-(+)-Camphor-10-sulfonic acid; (+)-Camphor-10-sulfonic acid; D-CAMPHORSULFONIC ACID; (1S)-(+)-樟脑-10-磺酸; (±)-β-樟脑磺酸; (±)-樟脑-10-磺酸; (+)-樟脑-10-磺酸(β); (1S)-樟脑-10-磺酸; (1S)-(+)-10-樟脑磺酸; 樟脑-10-磺酸(β); (+)-β-樟脑磺酸; (1S)-(+)-樟脑-10-磺酸; (+)-樟脑-10-磺酸

Database IDs

• CAS Number: 3144-16-9; 5872-08-2
• EC Number: 227-527-0; 221-554-1
• MDL Number: MFCD00074827; MFCD00064157
• Beilstein Number: 3205973; 2809675
• Merck Index: 141734
• PubChem SID: 24892465; 24852789; 24852792; 24848866; 162094296
• PubChem CID: 65617

CALCULATED PROPERTIES

• Acid pKa: -0.8099843
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -1.3937413
• LogD (pH = 7.4): -1.393791
• Log P: 0.9826071
• Molar Refractivity: 54.6607 cm^3
• Polarizability: 22.475769 Å^3
• Polar Surface Area: 71.44 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ~200 °C (dec.)(lit.); 196-200 °C (dec.)(lit.); 196-200°C dec.; 199-201 °C (dec.); 203-206 °C (dec.)(lit.)
• Optical Rotation: [α]20/D +19.9°, c = 2 in H2O; [α]20/D +21.5±1°, c = 10% in H2O; +20 (c=2 in water)

Safety Information

• Storage Warning: Hygroscopic
• RTECS: ED1530000; ED1550000
• European Hazard Symbols: Corrosive (C)
• UN Number: 3261; UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; III
• Risk Statements: 34
• Safety Statements: 20-26-36/37/39-45-60; 26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (T); 98%; 98+%(dry wt.), water <2%; 99%
• Grade: purum
• Impurities: ≤1% water
• Empirical Formula (Hill Notation): C10H16O4S

DETAILS

Sigma Aldrich - 147923

Application
Used in the protonation of polyaniline, a conducting polymer.
Packaging
100, 500 g in glass bottle

Sigma Aldrich - C2107

Packaging
5, 100, 500 g in glass bottle
Application
Used as a resolving agent,1 as a catalyst for coupling dipeptides.2

Sigma Aldrich - 21360

Other Notes
Reagent used for the resolution of bases; use as mobile phase additive for LC separations1,2; Reagent used for crystallization-induced asymmetric transformations3,4

REFERENCES

• Resolving agent for optically-active bases. For an improved resolution technique, using two immiscible solvents and half equivalent of resolving agent, see: Tetrahedron, 41, 2465 (1985). The procedure is claimed to lead to faster resolutions with higher optical purities than conventional methods.