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D-Camphorsulfonic acid

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Name

D-Camphorsulfonic acid

EINECS 221-554-1
CAS No. 3144-16-9 Density 1.331 g/cm3
PSA 79.82000 LogP 2.35040
Solubility soluble in water Melting Point 196-200 °C (dec.)(lit.)
Formula C10H16O4S Boiling Point 344.46°C (rough estimate)
Molecular Weight 232.301 Flash Point N/A
Transport Information UN 3261 8/PG 2 Appearance white to light beige powder
Safety 26-36/37/39-45-25-27 Risk Codes 34
Molecular Structure Molecular Structure of 3144-16-9 (D-Camphorsulfonic acid) Hazard Symbols CorrosiveC
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;

Article Data 24

D-Camphorsulfonic acid Synthetic route

60933-63-3

(1S)-10-camphorsulfonamide

3144-16-9

(1S)-10-camphorsulfonic acid

Conditions
ConditionsYield
With pyrylium tetrafluoroborate; magnesium chloride In tert-butyl alcohol at 60℃; for 5h;86%
357-57-3

brucine

5872-08-2

10-camphorsufonic acid

A

3144-16-9

(1S)-10-camphorsulfonic acid

B

35963-20-3

(R)-10-camphorsulfonic acid

464-49-3

(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one

3144-16-9

(1S)-10-camphorsulfonic acid

Conditions
ConditionsYield
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;
76-22-2

Camphor

3144-16-9

(1S)-10-camphorsulfonic acid

Conditions
ConditionsYield
With sulfuric acid; acetic anhydride die nach einiger Zeit auskrystallisierende Sulfonsaeure wird abgesaugt und mit Aether gewaschen;
5872-08-2

10-camphorsufonic acid

3144-16-9

(1S)-10-camphorsulfonic acid

Conditions
ConditionsYield
With brucine man zerlegt das ausscheideten Brucinsalz der -β-sulfonsaeure mit Barytwasser;
With brucine
3144-16-9

(1S)-10-camphorsulfonic acid

464-49-3

(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one

108-24-7

acetic anhydride

H2SO4

H2SO4

3144-16-9

(1S)-10-camphorsulfonic acid

(+)-1-hydroxy-camphene

(+)-1-hydroxy-camphene

3144-16-9

(1S)-10-camphorsulfonic acid

Conditions
ConditionsYield
With sulfuric acid; acetic anhydride
7647-01-0

hydrogenchloride

2935-35-5

(S)-2-phenylglycine

5872-08-2

10-camphorsufonic acid

A

3144-16-9

(1S)-10-camphorsulfonic acid

B

35963-20-3

(R)-10-camphorsulfonic acid

5872-08-2

10-camphorsufonic acid

A

3144-16-9

(1S)-10-camphorsulfonic acid

B

35963-20-3

(R)-10-camphorsulfonic acid

Conditions
ConditionsYield
With barium(II) perchlorate In methanol Solvent; Reagent/catalyst; Resolution of racemate;

D-Camphorsulfonic acid Consensus Reports

Reported in EPA TSCA Inventory.

D-Camphorsulfonic acid Specification

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%.

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.

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