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35963-20-3

Basic Information
CAS No.: 35963-20-3
Name: Bicyclo[2.2.1]heptane-1-methanesulfonicacid, 7,7-dimethyl-2-oxo-, (1R,4S)-
Molecular Structure:
Molecular Structure of 35963-20-3 (Bicyclo[2.2.1]heptane-1-methanesulfonicacid, 7,7-dimethyl-2-oxo-, (1R,4S)-)
Formula: C10H16O4S
Molecular Weight: 232.29
Synonyms: Bicyclo[2.2.1]heptane-1-methanesulfonicacid, 7,7-dimethyl-2-oxo-, (1R)-;(-)-(1R)-7,7-Dimethyl-2-oxobicyclo[2.2.1]heptane-1-methanesulfonic acid;(-)-10-Camphorsulfonic acid;(-)-Camphorsulfonic acid;(1R)-10-Camphorsulfonic acid;(R)-(-)-CSA;(R)-Camphor-10-sulfonic acid;l-10-Camphorsulfonic acid;L-(-) Camphor-10-Sulfonic Acid;
EINECS: 252-817-9
Density: 1.331 g/cm3
Melting Point: 198 °C (dec.)(lit.)
Boiling Point: 467.7°C at 760 mmHg
Flash Point: 236.6°C
Solubility: soluble in water
Appearance: white to light yellow crystal powder
Hazard Symbols: CorrosiveC
Risk Codes: 34
Safety: 26-36/37/39-45-24/25-27
Transport Information:
PSA: 79.82000
LogP: 2.35040
Synthetic route
188416-34-4, 137234-71-0

(2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (1R)-10-camphorsulfonate

35963-20-3

(R)-10-camphorsulfonic acid

Conditions
ConditionsYield
Stage #1: (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (1R)-10-camphorsulfonate With potassium carbonate In dichloromethane; water pH=8.9;
Stage #2: In dichloromethane; cyclohexane at 20 - 50℃; for 8h; Reagent/catalyst;
93.2%
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

5872-08-2

10-camphorsufonic acid

35963-20-3

(R)-10-camphorsulfonic acid

Conditions
ConditionsYield
With hydrogenchloride; d-phenylglycine
With brucine
35963-20-3

(R)-10-camphorsulfonic acid

brucine salt of/the/ -β-sulfonic acid

brucine salt of/the/ -β-sulfonic acid

35963-20-3

(R)-10-camphorsulfonic acid

Conditions
ConditionsYield
man zerlegt das in der Mutterlauge vom Brucinsalz der d-Saeure vorgekommene Salz mit Barytwasser;
l-camphor

l-camphor

35963-20-3

(R)-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

82509-30-6

d-camphor β-sulphonate ammonium salt

35963-20-3

(R)-10-camphorsulfonic acid

Conditions
ConditionsYield
In water; 4-methyl-2-pentanone at 80 - 117℃; Inert atmosphere;
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;
35963-20-3

(R)-10-camphorsulfonic acid

59543-81-6

4-(1H-imidazol-1-yl)-2-butanone

1-(3'-oxobutyl)imidazolium (+)-camphor-10-sulfonate

Conditions
ConditionsYield
In dichloromethane at 0℃; for 2h; Inert atmosphere;100%
35963-20-3

(R)-10-camphorsulfonic acid

603-33-8

triphenylbismuthane

Bi(3+)*3C10H15O4S(1-)

Conditions
ConditionsYield
In neat (no solvent) at 85℃; for 4h;100%
35963-20-3

(R)-10-camphorsulfonic acid

121352-80-5, 121422-48-8

(2S*,3R*,3'R*,4'R*)-2-(3',4'-epoxy-5'-hexenyl)tetrahydropyran-3-ol

121352-81-6

((1R,4S)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]hept-1-yl)-methanesulfonic acid (1R,2R)-2-hydroxy-4-((2S,3R)-3-hydroxy-tetrahydro-pyran-2-yl)-1-vinyl-butyl ester

Conditions
ConditionsYield
In dichloromethane for 0.5h; Ambient temperature;98%
855473-48-2

(R,E)-methyl 2-(3-(acetylthio)-3-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)propyl)benzoate

35963-20-3

(R)-10-camphorsulfonic acid

676-58-4

methylmagnesium chloride

(R,E)-2-[2-(3-{3-[2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-3-mercapto-propyl)-phenyl]-propan-2-ol (R)-camphorsulfonate

Conditions
ConditionsYield
Stage #1: methylmagnesium chloride With cerium(III) chloride In tetrahydrofuran at -20 - 25℃; for 1.75h;
Stage #2: (R,E)-methyl 2-(3-(acetylthio)-3-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)propyl)benzoate In tetrahydrofuran; toluene at -20℃; for 0.5h;
Stage #3: (R)-10-camphorsulfonic acid
97.65%
35963-20-3

(R)-10-camphorsulfonic acid

20667-12-3

silver(l) oxide

99147-14-5

silver (1R)-(-)-camphor-10-sulfonate

Conditions
ConditionsYield
In water an aq. soln. of the camphorsulfonic acid was treated with silver oxide; stirring for 5 min;; centrifugation and decantation; the supernatant was evapd. to dryness; the residue was washed with cold H2O and dried under vac.;;96.7%
3240-34-4

[bis(acetoxy)iodo]benzene

35963-20-3

(R)-10-camphorsulfonic acid

[hydroxy[((1R)-10-camphorylsulfonyl)oxy]iodo]benzene

Conditions
ConditionsYield
for 0.00555556h; Microwave irradiation; neat (no solvent);94%
for 0.166667h;91%
35963-20-3

(R)-10-camphorsulfonic acid

41018-45-5

naphthalen-1-yl-λ3-iodanediyl diacetate

C20H23IO5S

Conditions
ConditionsYield
for 0.166667h;94%
35963-20-3

(R)-10-camphorsulfonic acid

1111941-97-9

(2S,3R)-N-(2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)benzofuran-2-carboxamide R-camphorsulfonate

Conditions
ConditionsYield
In ethanol Heating / reflux;93.8%
931-53-3

Cyclohexyl isocyanide

35963-20-3

(R)-10-camphorsulfonic acid

N-cyclohexyl-C-(7,7-dimethyl-2-oxo-bicyclo[2.2.1]hept-1-yl)-methanesulfonamide

Conditions
ConditionsYield
With water In dichloromethane at 20℃; for 0.333333h;93%
225382-63-8

[2-(3-Methyl-3H-imidazol-4-yl)-thieno[3,2-b]pyridin-7-yl]-(2-methyl-1H-indol-5-yl)-amine

35963-20-3

(R)-10-camphorsulfonic acid

C20H17N5S*C10H16O4S

Conditions
ConditionsYield
In tetrahydrofuran; methanol; dichloromethane Large scale;93%
119072-55-8, 7188-38-7

tert-butylisonitrile

35963-20-3

(R)-10-camphorsulfonic acid

(R)-C-(7,7-dimethyl-2-oxo-bicyclo[2.2.1]hept-1-yl)-N-tert-butylmethanesulfonamide

Conditions
ConditionsYield
With water In dichloromethane at 20℃; for 0.333333h;92%
82789-35-3

methyl-1-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate

35963-20-3

(R)-10-camphorsulfonic acid

1375000-23-9

(1R,3R)-1-(3,4-methylenedioxyphenyl)-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylic methyl ester (1R)-10-camphorsulfonic acid salt

Conditions
ConditionsYield
In nitromethane at 0℃; Reflux;92%
35963-20-3

(R)-10-camphorsulfonic acid

dimethyl 2-((fluoromethyl)(phenyl)-l4-sulfaneylidene)malonate

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

Conditions
ConditionsYield
In acetone at 40℃; for 0.0833333h; Schlenk technique; Inert atmosphere;92%
1520-21-4

4-vinyl benzylamine

35963-20-3

(R)-10-camphorsulfonic acid

C10H16O4S*C8H9N

Conditions
ConditionsYield
In methanol; isopropyl alcohol at 0℃; for 1.5h;92%
760937-92-6

((2S,4S)-4-(4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl)pyrrolidin-2-yl)(1,3-thiazolidin-3-yl)methanone

35963-20-3

(R)-10-camphorsulfonic acid

3-{(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl}thiazolidine di-(-)-camphorsulfonate

Conditions
ConditionsYield
In tetrahydrofuran; tert-butyl methyl ether at 20℃; for 1h;91%
35963-20-3

(R)-10-camphorsulfonic acid

72597-34-3

(+/-)-10-Camphorsulfonamide

Conditions
ConditionsYield
With ammonium hydroxide In dichloromethane at 0℃; for 2h;90%
Stage #1: (R)-10-camphorsulfonic acid With thionyl chloride In chloroform for 17h; Heating / reflux;
Stage #2: With ammonia In chloroform; water at 4 - 20℃; for 4h;
83%
Multi-step reaction with 2 steps
1: 80.5 percent / PCl5 / 1 h at 0 deg C and 2 h at r.t.
2: 74 percent / NH3 / toluene / 0 °C
View Scheme
120-57-0

piperonal

35963-20-3

(R)-10-camphorsulfonic acid

7303-49-3

DL-tryptophan methyl ester

1375000-23-9

(1R,3R)-1-(3,4-methylenedioxyphenyl)-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylic methyl ester (1R)-10-camphorsulfonic acid salt

Conditions
ConditionsYield
In nitromethane at 0 - 30℃; Reflux;90%
35963-20-3

(R)-10-camphorsulfonic acid

75276-67-4

1-(2-methyl-3-chlorophenyl)-4,6-dimethylpyrimidin-2(1H)-thione

75276-78-7

1-(2-methyl-3-chlorophenyl)-4,6-dimethyl-2-thioxo-1,2-dihydropyrimidinium D-camphor-10-sulphonate

Conditions
ConditionsYield
In ethanol for 1h; Heating;89%
35963-20-3

(R)-10-camphorsulfonic acid

83391-98-4, 83435-51-2, 106036-93-5

1-β-dimethylaminoethyl-3,3-bis(trifluoromethyl)diaziridine

83429-30-5

[2-(3,3-Bis-trifluoromethyl-diaziridin-1-yl)-ethyl]-dimethyl-amine; compound with ((1R,4S)-7,7-dimethyl-2-oxo-bicyclo[2.2.1]hept-1-yl)-methanesulfonic acid

Conditions
ConditionsYield
In isopropyl alcohol at 0℃; for 24h;88.1%
35963-20-3

(R)-10-camphorsulfonic acid

113665-84-2

(S)-(+)-clopidogrel

clopidogrel (1R)-(-)-camphor-10-sulfonate

Conditions
ConditionsYield
In acetone at 20℃; for 12h;88%
In acetone at 20℃; for 4h;86%
In acetone at 25 - 56℃; for 2.5h;85.25%
In ethyl acetate at 20℃; for 2h; Product distribution / selectivity;
In acetone at 20℃; for 2h; Product distribution / selectivity;
35963-20-3

(R)-10-camphorsulfonic acid

C22H27FN4O3

C10H16O4S*C17H19FN4O

Conditions
ConditionsYield
In water; acetonitrile at 60℃; for 4.5h; Solvent; Inert atmosphere; Large scale;88%
35963-20-3

(R)-10-camphorsulfonic acid

28899-97-0

triphenylbismuth(V) diacetate

triphenylbismuth bis[(1R)-(-)-camphor-10-sulfonate]

Conditions
ConditionsYield
In acetonitrile addn. of soln. of (1R)-(-)-camphor-10-sulfonic acid (2 equiv.) in MeCN to soln. of Bi(OAc)2Ph3 (1 equiv.) in MeCN; reflux with stirring for 1 h; filtration, removal of solvent under reduced pressure, recrystn. from CH2Cl2-Et2O-pentane; elem. anal.;86%
35963-20-3

(R)-10-camphorsulfonic acid

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

Conditions
ConditionsYield
With sodium azide; trichloroacetonitrile; triphenylphosphine In acetonitrile at 20℃; for 2h;86%
6290-03-5

(R)-butane-1,3-diol

35963-20-3

(R)-10-camphorsulfonic acid

91-00-9

Benzhydrylamine

(2S)-1-(diphenylmethyl)-2-methylazetidinium [(1R,4S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonate

Conditions
ConditionsYield
Stage #1: (R)-butane-1,3-diol With trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine In acetonitrile at -35 - -30℃; for 3.83333h; Inert atmosphere;
Stage #2: Benzhydrylamine In acetonitrile at -35 - 45℃; for 2.66667h;
Stage #3: (R)-10-camphorsulfonic acid In methanol at 10 - 20℃; for 0.25h;
86%
Stage #1: (R)-butane-1,3-diol With trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine In acetonitrile at -35 - -30℃; for 0.833333h;
Stage #2: (R)-10-camphorsulfonic acid; Benzhydrylamine In acetonitrile at -30 - 45℃;
65%
35963-20-3

(R)-10-camphorsulfonic acid

112101-81-2

5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide

906338-31-6

C10H16N2O3S*C10H16O4S

Conditions
ConditionsYield
In water; isopropyl alcohol at 0 - 4℃; for 1.5h; Product distribution / selectivity; Heating / reflux;85.65%

(R)-5-(2-aminoethyl)-1-(6,8-difluorochroman-3-yl)-1,3-dihydroimidazole-2-thione

35963-20-3

(R)-10-camphorsulfonic acid

(R)-5-(2-aminoethyl)-1-(6,8-difluorochroman-3-yl)-1,3-dihydroimidazole-2-thione camphorsulfonate

Conditions
ConditionsYield
In methanol at 20 - 50℃; for 2h; Product distribution / selectivity; Heating / reflux;85%
In methanol; ethyl acetate at 20 - 50℃; for 2h; Product distribution / selectivity; Heating / reflux;
In methanol; isopropyl alcohol at 20 - 50℃; for 2h; Product distribution / selectivity; Heating / reflux;
1445-45-0

Trimethyl orthoacetate

35963-20-3

(R)-10-camphorsulfonic acid

83603-04-7

methyl 1R-(-)-10-camphorsulphonate

Conditions
ConditionsYield
In dichloromethane at 20℃;85%
at 20℃;85%
391-77-5

4-Chloro-6-fluoroquinoline

17159-79-4

ethyl 4-oxocyclohexane-1-carboxylate

35963-20-3

(R)-10-camphorsulfonic acid

4-(6-fluoroquinolin-4-yl)cyclohexan-1-one ((1R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonate

Conditions
ConditionsYield
Stage #1: ethyl 4-oxocyclohexane-1-carboxylate; (R)-10-camphorsulfonic acid In ethylene glycol; toluene at 60℃; for 4h; Inert atmosphere; Dean-Stark; Large scale;
Stage #2: 4-Chloro-6-fluoroquinoline With sodium hexamethyldisilazane In tetrahydrofuran; N,N-dimethyl-formamide; toluene at -20℃; for 3h; Large scale;
Stage #3: In ethylene glycol Temperature; Large scale;
84.8%
35963-20-3

(R)-10-camphorsulfonic acid

90055-48-4

clopidogrel

(+)-clopidogrel camphorsulfonic acid

Conditions
ConditionsYield
In 1,2-dichloro-ethane at 20℃; for 53h; Product distribution / selectivity;84.7%
In ethyl acetate at 20℃; for 53h; Product distribution / selectivity;83.8%
In isopropyl alcohol at 20 - 35℃; for 53h; Product distribution / selectivity;82.9%
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    1R-(-)-Camphorsulfonic acid

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    L(-)-Camphorsulfonic acid

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    MSDS/COA Download

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    35963-20-3

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Chemistry

Synonyms: (1r)-[7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulphonic acid;(1R)-(-)-10-CAMPHORSULFONIC ACID; (1R)-(-)-CAMPHOR-10-SULPHONIC ACID;(1R)-(-)-CAMPHOR-10-SULFONIC ACID;(1R)-CAMPHOR-10-SULFONIC ACID;(1R)-(-)-CAMPHORSULFONIC ACID;
(-)-10-CAMPHORSULFONIC ACID;(-)-CAMPHOR-10-SULPHONIC ACID ;(-)-10-CAMPHORSULFONIC ACID;(-)-CAMPHOR-10-SULPHONIC ACID ;
Molecular formula: C10H16O4S
Molecular Weight: 232.3
Molecular Structure :
EINECS: 252-817-9
Melting point: 198 °C (dec.)(lit.)
alpha: -22 o (c=20,H2O)
refractive index : -21.5 ° (C=5, H2O)
storage temp.:2-8°C
Water Solubility:soluble
Sensitive:Hygroscopic

Safety Profile

Hazard Codes:  C
The Risk Statements information of  L(-)-Camphorsulfonic acid:
34:  Causes burns 
The Safety Statements information of  L(-)-Camphorsulfonic acid:
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
27:  Take off immediately all contaminated clothing 
45:  In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) 
24/25:  Avoid contact with skin and eyes 
36/37/39:  Wear suitable protective clothing, gloves and eye/face protection 
RIDADR:UN 3261 8/PG 2
WGK Germany:3
F:3-10
HazardClass:8