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D-(+)-10-Camphorsulfonic acid

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Name

D-(+)-10-Camphorsulfonic acid

EINECS 227-527-0
CAS No. 5872-08-2 Density 1.331 g/cm3
PSA 79.82000 LogP 2.35040
Solubility Soluble in water. Melting Point 203-206 °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 off-white powder
Safety 26-36/37/39-45-27 Risk Codes 34
Molecular Structure Molecular Structure of 5872-08-2 (DL-10-CAMPHORSULFONIC ACID) Hazard Symbols CorrosiveC
Synonyms

(7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methanesulfonic acid;(1R)-(7,7-Dimethyl-2-oxobicyclo(2.2.1)hept-1-yl)methanesulphonic acid;(RS)-10-Camphorsulfonic acid;10-camphorsulfonic acid;Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-;2-Oxo-10-bornanesulfonic acid;Camphor-10-sulfonic acid;DL-10-Camphorsulfonicacid;DL-Camphorsulfonic acid;

Article Data 8

D-(+)-10-Camphorsulfonic acid Synthetic route

76-22-2

Camphor

5872-08-2

10-camphorsufonic acid

Conditions
ConditionsYield
With sulfuric acid; acetic anhydride
464-49-3

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

5872-08-2

10-camphorsufonic acid

Conditions
ConditionsYield
With sulfuric acid; acetic anhydride Reychler method;
dl-camphor

dl-camphor

5872-08-2

10-camphorsufonic acid

Conditions
ConditionsYield
With sulfuric acid; acetic anhydride
5872-08-2

10-camphorsufonic acid

2712-78-9

bis-[(trifluoroacetoxy)iodo]benzene

[di((camphorsulfonyl)oxy)iodo]benzene

Conditions
ConditionsYield
In acetonitrile at 20℃; for 3h; Inert atmosphere;98%
5872-08-2

10-camphorsufonic acid

25435-53-4

(2,2,3-Trimethyl-cyclopent-3-enyl)-acetic acid

Conditions
ConditionsYield
With potassium hydroxide at 200 - 220℃; for 0.0833333h; Retro-Prins fragmentation;90%
1445-45-0

Trimethyl orthoacetate

5872-08-2

10-camphorsufonic acid

46471-67-4, 62319-13-5, 83603-04-7

(+/-)-2-oxo-bornane-10-sulfonic acid methyl ester

Conditions
ConditionsYield
In dichloromethane at 20℃;89%
In dichloromethane at 20℃;89%
5872-08-2

10-camphorsufonic acid

81403-80-7

alfuzosin

N1-(4-amino-6,7-dimethoxyquinazol-2-yl)-N1-methyl-N2-(tetrahydrofuro-2-yl)propylenediamine (7,7-dimethyl-2-oxo-bicyclo[2,2,1]hept-1-yl)methanesulfonate

Conditions
ConditionsYield
In ethyl acetate at 20 - 50℃; Product distribution / selectivity; Inert atmosphere;88%
1253568-74-9

2-(tetrahydro-2H-pyran-2-yl)-N-(3-(9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)pyridin-2-yl)-2H-indazol-4-amine

5872-08-2

10-camphorsufonic acid

N-(3-(9H-purin-6-yl)pyridin-2-yl)-1H-indazol-4-amine (+/-)-10-camphorsulfonate

Conditions
ConditionsYield
In methanol; dichloromethane at 40℃; for 22h;86%
5872-08-2

10-camphorsufonic acid

6994-93-0

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

Conditions
ConditionsYield
With thionyl chloride In N,N-dimethyl-formamide at 0 - 20℃; for 4.5h;85%
With trichloroacetonitrile; triphenylphosphine In dichloromethane for 1h; Heating;
5872-08-2

10-camphorsufonic acid

81403-68-1

alfuzosin hydrochloride

N1-(4-amino-6,7-dimethoxyquinazol-2-yl)-N1-methyl-N2-(tetrahydrofuro-2-yl)propylenediamine (7,7-dimethyl-2-oxo-bicyclo[2,2,1]hept-1-yl)methanesulfonate

Conditions
ConditionsYield
Stage #1: alfuzosin hydrochloride With sodium hydroxide In dichloromethane; water
Stage #2: 10-camphorsufonic acid In dichloromethane at 20 - 40℃; Product distribution / selectivity;
84%

D-(+)-10-Camphorsulfonic acid Specification

The Bicyclo[2.2.1]heptane-1-methanesulfonicacid, 7,7-dimethyl-2-oxo-, with the CAS registry number 5872-08-2 and EINECS registry number 227-527-0, has the systematic name of (7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methanesulfonic acid. It belongs to the following product categories: Pharmaceutical Intermediates; FINE Chemical & INTERMEDIATES; Bicyclic Monoterpenes; Biochemistry; Reagents for Oligosaccharide Synthesis; Terpenes; Organic AcidsOrganic Conductors and Photovoltaics: OFET and OPV Materials; Chemical Synthesis; Conducting Polymers and Monomers; Polyanilines and Polyaniline Dopants; Synthetic Reagents. And the molecular formula of the chemical is C10H16O4S.

The characteristics of Bicyclo[2.2.1]heptane-1-methanesulfonicacid, 7,7-dimethyl-2-oxo- are as followings: (1)# of Rule of 5 Violations: 0; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 1; (5)ACD/KOC (pH 7.4): 1; (6)#H bond acceptors: 4; (7)#H bond donors: 1; (8)#Freely Rotating Bonds: 2; (9)Polar Surface Area: 79.82 Å2; (10)Index of Refraction: 1.54; (11)Molar Refractivity: 54.724 cm3; (12)Molar Volume: 174.486 cm3; (13)Polarizability: 21.694×10-24cm3; (14)Surface Tension: 49.952 dyne/cm; (15)Density: 1.331 g/cm3.

Uses of Bicyclo[2.2.1]heptane-1-methanesulfonicacid, 7,7-dimethyl-2-oxo-: It can react with 1-(3-chloro-2-methyl-phenyl)-4,6-dimethyl-1H-pyrimidine-2-thione to produce 1-(2-methyl-3-chlorophenyl)-4,6-dimethyl-2-thioxo-1,2-dihydropyrimidinium D-camphor-10-sulphonate. This reaction will need reagent ethanol. The reaction time is 1 hour with heating, and the yield is about 89%. 

You should be cautious while dealing with this chemical. It may cause burns. Therefore, you had better take the following instructions: Wear suitable protective clothing, gloves and eye/face protection; In case of contacting with eyes, rinse immediately with plenty of water and seek medical advice; Take off immediately all contaminated clothing; In case of accident or if you feel unwell, seek medical advice immediately (show label where possible).

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: CC1(C2CCC1(C(=O)C2)CS(=O)(=O)O)C
(2)InChI: InChI=1/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-UHFFFAOYAN

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