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| CAS No.: | 3144-16-9 |
|---|---|
| Name: | D-Camphorsulfonic acid |
| Molecular Structure: | |
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| Formula: | C10H16O4S |
| Molecular Weight: | 232.301 |
| Synonyms: | 10-Bornanesulfonicacid, 2-oxo-, (1S,4R)-(+)- (8CI);Bicyclo[2.2.1]heptane-1-methanesulfonic acid,7,7-dimethyl-2-oxo-, (1S)-;(+)-2-Oxo-10-bornanesulfonic acid;(+)-Camphor-w-sulfonic acid;(+)-D-Camphor-10-sulfonic acid;(S)-(+)-CSA;(S)-Camphor-10-sulfonic acid;Camphor-w-sulfonic acid, (+)-;D-(+)-Camphorsulfonic acid;D-Camphor-b-sulfonic acid;Reychler's acid;b-Camphorsulfonic acid, (+)-;D-(+)-camphour sulphonic acid;D-Camphorsulfonic acid; |
| EINECS: | 221-554-1 |
| Density: | 1.331 g/cm3 |
| Melting Point: | 196-200 °C (dec.)(lit.) |
| Boiling Point: | 344.46°C (rough estimate) |
| Solubility: | soluble in water |
| Appearance: | white to light beige powder |
| Hazard Symbols: |
 C
|
| Risk Codes: | 34 |
| Safety: | 26-36/37/39-45-25-27 |
| Transport Information: | UN 3261 8/PG 2 |
| PSA: | 79.82000 |
| LogP: | 2.35040 |
(1S)-10-camphorsulfonamide
(1S)-10-camphorsulfonic acid
| Conditions | Yield |
|---|---|
| With pyrylium tetrafluoroborate; magnesium chloride In tert-butyl alcohol at 60℃; for 5h; | 86% |
brucine
10-camphorsufonic acid
A
(1S)-10-camphorsulfonic acid
B
(R)-10-camphorsulfonic acid
| Conditions | Yield |
|---|---|
| With sulfuric acid; acetic anhydride | |
| With sulfuric acid In acetic anhydride | |
| With sulfuric acid; acetic anhydride | |
| With sulfuric acid; acetic anhydride | |
| With sulfuric acid; acetic anhydride Wagner-Meerwein Rearrangement; |
| Conditions | Yield |
|---|---|
| With sulfuric acid; acetic anhydride die nach einiger Zeit auskrystallisierende Sulfonsaeure wird abgesaugt und mit Aether gewaschen; |
| Conditions | Yield |
|---|---|
| With brucine man zerlegt das ausscheideten Brucinsalz der -β-sulfonsaeure mit Barytwasser; | |
| With brucine |
camphor-10-sulfonic acid
(1S)-10-camphorsulfonic acid
(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
acetic anhydride
(1S)-10-camphorsulfonic acid
(1S)-10-camphorsulfonic acid
| Conditions | Yield |
|---|---|
| With sulfuric acid; acetic anhydride |
hydrogenchloride
(S)-2-phenylglycine
10-camphorsufonic acid
A
(1S)-10-camphorsulfonic acid
B
(R)-10-camphorsulfonic acid
10-camphorsufonic acid
A
(1S)-10-camphorsulfonic acid
B
(R)-10-camphorsulfonic acid
| Conditions | Yield |
|---|---|
| With barium(II) perchlorate In methanol Solvent; Reagent/catalyst; Resolution of racemate; |
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1.Introduction of D-Camphorsulfonic acid
The D-Camphorsulfonic acid, with the CAS registry number 3144-16-9, is also known as 2-Oxobornane-10-sulphonic acid. It belongs to the product categories of Pharmaceutical Intermediates; Fine Chemical & Intermediates; Chiral Compounds; Chiral; Bicyclic Monoterpenes; Biochemistry; For Resolution of Bases; Optical Resolution; Reagents for Oligosaccharide Synthesis; Synthetic Organic Chemistry; Terpenes; Peptide. Its EINECS registry number is 221-554-1. Its IUPAC name is called (7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl)methanesulfonic acid. This chemical is white to light beige powder which can be used as resolving agent and catalyst for coupling dipeptides. The product should be sealed and stored in cool and dry place (2-8°C).
2.Physical properties of D-Camphorsulfonic acid
(1)ACD/LogP: -0.58; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -4.02; (4)ACD/LogD (pH 7.4): -4.07; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.539; (13)Molar Refractivity: 54.72 cm3; (14)Molar Volume: 174.4 cm3; (15)Surface Tension: 49.9 dyne/cm; (16)Density: 1.331 g/cm3; (17)Melting Point: 196-200 °C (dec.)(lit.).
3.Structure descriptors of D-Camphorsulfonic acid
(1)Canonical SMILES: CC1(C2CCC1(C(=O)C2)CS(=O)(=O)O)C
(2)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)
(3)InChIKey: MIOPJNTWMNEORI-UHFFFAOYSA-N
4.Uses of D-Camphorsulfonic acid
D-Camphorsulfonic acid can be used to produce (1R)-7,7-dimethyl-2-oxo-bicyclo[2.2.1]heptane-1-methanesulfonamide at temperature of 0 °C. This reaction will need reagent NH4OH and solvent CH2Cl2 with reaction time of 2 hours. The yield is about 90%.
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5.Safety information of D-Camphorsulfonic acid
This chemical may destroy living tissue on contact. It may cause burns. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell seek medical advice immediately (show the label where possible).
6.The toxicity data of D-Camphorsulfonic acid
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD50 | subcutaneous | 2502mg/kg (2502mg/kg) | Pharmazie. Vol. 1, Pg. 150, 1946. |
