Product Name

  • Name

    DL-10-CAMPHORSULFONIC ACID

  • EINECS 227-527-0
  • CAS No. 5872-08-2
  • Article Data8
  • CAS DataBase
  • Density 1.331 g/cm3
  • 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
  • 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;
  • PSA 79.82000
  • LogP 2.35040

Synthetic route

Camphor
76-22-2

Camphor

10-camphorsufonic acid
5872-08-2

10-camphorsufonic acid

Conditions
ConditionsYield
With sulfuric acid; acetic anhydride
(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
464-49-3

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

10-camphorsufonic acid
5872-08-2

10-camphorsufonic acid

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

dl-camphor

10-camphorsufonic acid
5872-08-2

10-camphorsufonic acid

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

10-camphorsufonic acid

bis-[(trifluoroacetoxy)iodo]benzene
2712-78-9

bis-[(trifluoroacetoxy)iodo]benzene

[di((camphorsulfonyl)oxy)iodo]benzene

[di((camphorsulfonyl)oxy)iodo]benzene

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

10-camphorsufonic acid

(2,2,3-Trimethyl-cyclopent-3-enyl)-acetic 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%
Trimethyl orthoacetate
1445-45-0

Trimethyl orthoacetate

10-camphorsufonic acid
5872-08-2

10-camphorsufonic acid

(+/-)-2-oxo-bornane-10-sulfonic acid methyl ester
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%
10-camphorsufonic acid
5872-08-2

10-camphorsufonic acid

alfuzosin
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

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%
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
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

10-camphorsufonic acid
5872-08-2

10-camphorsufonic acid

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

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%
10-camphorsufonic acid
5872-08-2

10-camphorsufonic acid

((1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonyl chloride
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;
10-camphorsufonic acid
5872-08-2

10-camphorsufonic acid

alfuzosin hydrochloride
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

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%
10-camphorsufonic acid
5872-08-2

10-camphorsufonic acid

1,3,3-Trimethyl-5-nitro-2-{(E)-3-[1,3,3-trimethyl-5-nitro-1,3-dihydro-indol-(2E)-ylidene]-propenyl}-2,3-dihydro-1H-indol-2-ol

1,3,3-Trimethyl-5-nitro-2-{(E)-3-[1,3,3-trimethyl-5-nitro-1,3-dihydro-indol-(2E)-ylidene]-propenyl}-2,3-dihydro-1H-indol-2-ol

1,3,3,1',3',3'-Hexamethyl-5,5'-dinitroindocarbocyanine dl-10-camphorsulfonate

1,3,3,1',3',3'-Hexamethyl-5,5'-dinitroindocarbocyanine dl-10-camphorsulfonate

Conditions
ConditionsYield
With potassium hydroxide In methanol; water81%
9-methyl-3-oxa-9-azatricyclo[3.3.1.0(2,4)]non-7-yl hydroxy(di-2-thienyl)acetate

9-methyl-3-oxa-9-azatricyclo[3.3.1.0(2,4)]non-7-yl hydroxy(di-2-thienyl)acetate

10-camphorsufonic acid
5872-08-2

10-camphorsufonic acid

C10H15O4S(1-)*C19H22NO4S2(1+)

C10H15O4S(1-)*C19H22NO4S2(1+)

Conditions
ConditionsYield
In dichloromethane; acetonitrile at 20℃; for 24h;80%
brucine
357-57-3

brucine

10-camphorsufonic acid
5872-08-2

10-camphorsufonic acid

A

(1S)-10-camphorsulfonic acid
3144-16-9

(1S)-10-camphorsulfonic acid

B

(R)-10-camphorsulfonic acid
35963-20-3

(R)-10-camphorsulfonic acid

...Expand
10-camphorsufonic acid
5872-08-2

10-camphorsufonic acid

(1S)-10-camphorsulfonic acid
3144-16-9

(1S)-10-camphorsulfonic acid

Conditions
ConditionsYield
With brucine man zerlegt das ausscheideten Brucinsalz der -β-sulfonsaeure mit Barytwasser;
With brucine
10-camphorsufonic acid
5872-08-2

10-camphorsufonic acid

(R)-10-camphorsulfonic acid
35963-20-3

(R)-10-camphorsulfonic acid

Conditions
ConditionsYield
With hydrogenchloride; d-phenylglycine
With brucine
10-camphorsufonic acid
5872-08-2

10-camphorsufonic acid

Potassium; ((1S,4R)-7,7-dimethyl-2-oxo-bicyclo[2.2.1]hept-1-yl)-methanesulfonate
21791-95-7

Potassium; ((1S,4R)-7,7-dimethyl-2-oxo-bicyclo[2.2.1]hept-1-yl)-methanesulfonate

Conditions
ConditionsYield
With potassium hydroxide
10-camphorsufonic acid
5872-08-2

10-camphorsufonic acid

C10H15PS4

C10H15PS4

Conditions
ConditionsYield
With tetraphosphorus decasulfide; tetra(n-butyl)ammonium hydroxide 2.) toluene, reflux, 16h; Yield given. Multistep reaction;
hydrogenchloride
7647-01-0

hydrogenchloride

(S)-2-phenylglycine
2935-35-5

(S)-2-phenylglycine

10-camphorsufonic acid
5872-08-2

10-camphorsufonic acid

A

(1S)-10-camphorsulfonic acid
3144-16-9

(1S)-10-camphorsulfonic acid

B

(R)-10-camphorsulfonic acid
35963-20-3

(R)-10-camphorsulfonic acid

...Expand
10-camphorsufonic acid
5872-08-2

10-camphorsufonic acid

N-phenethyl-10-camphorsulfonamide

N-phenethyl-10-camphorsulfonamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Cl3CCN; PPh3 / CH2Cl2 / 1 h / Heating
2: 4-picoline / CH2Cl2 / 1 h / 20 °C
View Scheme
10-camphorsufonic acid
5872-08-2

10-camphorsufonic acid

(+/-)-6-(camphor-10-sulfonamido)-hexanoic acid

(+/-)-6-(camphor-10-sulfonamido)-hexanoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 85 percent / SOCl2 / dimethylformamide / 4.5 h / 0 - 20 °C
2.1: MgO / H2O; dioxane / 0.25 h / Heating
2.2: 65 percent / H2O; dioxane / 16 h
View Scheme
10-camphorsufonic acid
5872-08-2

10-camphorsufonic acid

(+/-)-6-(camphorquinone-10-sulfonamido)-hexanoic acid

(+/-)-6-(camphorquinone-10-sulfonamido)-hexanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 85 percent / SOCl2 / dimethylformamide / 4.5 h / 0 - 20 °C
2.1: MgO / H2O; dioxane / 0.25 h / Heating
2.2: 65 percent / H2O; dioxane / 16 h
3.1: SeO2 / H2O; dioxane / 120 h / Heating
View Scheme
10-camphorsufonic acid
5872-08-2

10-camphorsufonic acid

10 bromocamphor
1925-54-8, 64161-50-8, 116783-25-6

10 bromocamphor

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: KOH
2: PBr3
3: xylene / Heating; Dallacker et al. method
View Scheme
10-camphorsufonic acid
5872-08-2

10-camphorsufonic acid

(+)-10-bromo-2-chloro-2-nitrosocamphane

(+)-10-bromo-2-chloro-2-nitrosocamphane

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: KOH
2: PBr3
3: xylene / Heating; Dallacker et al. method
4: NH2OH-HCl
5: Cl2 gas / diethyl ether / 0 °C / Davidson method
View Scheme
10-camphorsufonic acid
5872-08-2

10-camphorsufonic acid

10-bromocamphor oxime

10-bromocamphor oxime

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: KOH
2: PBr3
3: xylene / Heating; Dallacker et al. method
4: NH2OH-HCl
View Scheme
10-camphorsufonic acid
5872-08-2

10-camphorsufonic acid

((1S,4R)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]hept-1-yl)-methanesulfonyl bromide

((1S,4R)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]hept-1-yl)-methanesulfonyl bromide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: KOH
2: PBr3
View Scheme
Ph(3-Cl)(5-OCHF2)-(R)CH(OH)C(O)-Aze-Pab(OMe)
433937-93-0

Ph(3-Cl)(5-OCHF2)-(R)CH(OH)C(O)-Aze-Pab(OMe)

10-camphorsufonic acid
5872-08-2

10-camphorsufonic acid

C10H16O4S*C22H23ClF2N4O5

C10H16O4S*C22H23ClF2N4O5

4,4'-diformylbiphenyl
66-98-8

4,4'-diformylbiphenyl

10-camphorsufonic acid
5872-08-2

10-camphorsufonic acid

C34H36O8S2(2-)*2Na(1+)

C34H36O8S2(2-)*2Na(1+)

Conditions
ConditionsYield
Stage #1: 10-camphorsufonic acid With sodium methylate In methanol; toluene at 25 - 66℃;
Stage #2: 4,4'-diformylbiphenyl In methanol; toluene at 66 - 70℃; for 7h;
2-methylspiro(1,3-oxathiolane-5,3'-quinuclidine)
124620-88-8

2-methylspiro(1,3-oxathiolane-5,3'-quinuclidine)

10-camphorsufonic acid
5872-08-2

10-camphorsufonic acid

cis-2-methylspiro(1,3-oxathiolane-5,3')quinuclidine camphorsulfonic acid salt

cis-2-methylspiro(1,3-oxathiolane-5,3')quinuclidine camphorsulfonic acid salt

Conditions
ConditionsYield
In methanol; toluene at 20℃; for 22h;12.04 g
10-camphorsufonic acid
5872-08-2

10-camphorsufonic acid

A

(1S)-10-camphorsulfonic acid
3144-16-9

(1S)-10-camphorsulfonic acid

B

(R)-10-camphorsulfonic acid
35963-20-3

(R)-10-camphorsulfonic acid

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

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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