D-Camphorsulfonic acid supplier

Name
D-Camphorsulfonic acid
EINECS 221-554-1
CAS No. 3144-16-9
Article Data24
CAS DataBase
Density 1.331 g/cm³
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
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
Hazard Symbols C
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;
PSA 79.82000
LogP 2.35040

Synthetic route

: 60933-63-3
(1S)-10-camphorsulfonamide

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

Conditions

Conditions	Yield
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

...Expand

: 464-49-3
(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one

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

Conditions

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;

: 76-22-2
Camphor

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

Conditions

Conditions	Yield
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

Conditions	Yield
With brucine man zerlegt das ausscheideten Brucinsalz der -β-sulfonsaeure mit Barytwasser;
With brucine

: 76-26-6, 3144-16-9, 5872-08-2, 35963-20-3
camphor-10-sulfonic acid

: 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

...Expand

(+)-1-hydroxy-camphene: (+)-1-hydroxy-camphene

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

Conditions

Conditions	Yield
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

...Expand

: 5872-08-2
10-camphorsufonic acid

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

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

Conditions

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

: 5-methyl-6a-phenylhexahydro-1H-pyrrolo[3,4-c]isoxazole

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

: 5-methyl-6a-phenylhexahydro-1H-pyrrolo[3,4-c][1,2]oxazol-5-ium (7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methane sulfonate

Conditions

Conditions	Yield
In acetone at 20℃; Heating;	100%

: 5-methyl-6a-phenylhexahydro-1H-pyrrolo[3,4-c]isoxazole

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

: 5-methyl-6a-phenylhexahydro-1H-pyrrolo[3,4-c][1,2]oxazol-1,5-diium (7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methane sulfonate

Conditions

Conditions	Yield
In acetone at 20℃; Heating;	100%

: (rac)-1,8,9,16-tetramethyl-6,7,10,11-tetrahydrodipyrido[2,1-a:1',2'-k][2,9]phenanthroline-5,12-diium trifluoromethanesulfonate

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

: (rac)-1,8,9,16-tetramethyl-6,7,10,11-tetrahydrodipyrido[2,1-a:1',2'-k][2,9]phenanthroline-5,12-diium ((1S,3S,4S)-3-bromo-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonate

Conditions

Conditions	Yield
With strongly basic anion exchange chloride resin Dowex 1 x 2; 16-100 mesh In methanol	100%

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

: 123-41-1
cholin hydroxide

: 1639366-27-0
[cholinium][(S)-camphorsulfonate]

Conditions

Conditions	Yield
for 1h; Inert atmosphere;	100%

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

: (R)-2-methyl-6-(1-phenylethyl)aniline

: (R)-2-methyl-6-(1-phenylethyl)benzenaminium ((1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonate

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 12h;	100%

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

: 284461-73-0
sorafenib

: 4-{4-[({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenoxy}-N-methylpyridine-2-carboxamide hemicamsylate

Conditions

Conditions	Yield
In tert-butyl methyl ether at 15 - 50℃; Solvent; Temperature;	99.4%

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

: 21286-54-4
Camphorsulfonyl chloride

Conditions

Conditions	Yield
With thionyl chloride; N,N-dimethyl-formamide at 20℃; for 3h;	99%
With thionyl chloride at 0 - 50℃; for 2.5h;	98%
With thionyl chloride for 2h; Heating;	98%

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

: silver carbonate

: 20520-61-0
silver camphorsulfonate

Conditions

Conditions	Yield
In methanol 2 equivalents of d-camphor-10-sulfonic acid; the mixture was refluxed for 2 h;; cooling down to 35-40 ° C; filtration; solvent evaporation;;	99%

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

: 603-33-8
triphenylbismuthane

: bis-phenylbismuth(III) (S)-(+)-10-camphorsulfonate

Conditions

Conditions	Yield
In neat (no solvent) byproducts: benzene; BiPh3 and sulfonic acid (molar ratio 1:2) ground together briefly in mortar; heated at 85°C for 4 h; powder isolated; washed with small amt. of toluene and EtOH;	99%
In ethanol mixt. of BiPh3 and sulfonic acid stirred in EtOH at room temp. for 2-3 dand crystd. over 3-4 d; or stirred for 1 wk (ppt. obtained); crystals collected by filtration; ppt. collected by filtration and washed with toluene and H2O; elem. anal.;	73%

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

: 7732-18-5
water

: 1304-76-3
bismuth(III) oxide

: [Bi18O12(OH)12(S-(+)-10-camphorsulfonate)18(H2O)2]*13H2O

Conditions

Conditions	Yield
In not given	99%

...Expand

: rac-3-methyl-2-(2-methylnaphthalen-1-yl)-4-phenyl-5,6-dihydrobenzo[h]quinoline

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

: 3-methyl-2-(2-methylnaphthalen-1-yl)-4-phenyl-5,6-dihydrobenzo[h]quinolinium (1S)-camphor-10-sulfonate

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 0.5h;	99%

: 1445-45-0
Trimethyl orthoacetate

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

: 62319-13-5
(1S,4R)-methyl (7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methanesulfonate

Conditions

Conditions	Yield
In dichloromethane for 0.5h; Ambient temperature;	98%
In dichloromethane at 20℃; for 1.5h;	90%
In dichloromethane at 20℃;	87%
In dichloromethane at 20℃;	87%

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

: 78622-29-4, 84708-94-1
(1S,4R)-1-(iodomethyl)-7,7-dimethylbicyclo-[2.2.1]heptan-2-one

Conditions

Conditions	Yield
With iodine; triphenylphosphine In toluene at 111℃; for 16h;	98%
With iodine; triphenylphosphine In toluene for 16h; Substitution; Heating;	92%
With iodine; triphenylphosphine In toluene	88%

: 3731-51-9
(2-aminomethylpyridine)

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

: C16H22N2O3S

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In chloroform for 20h; Heating;	98%

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

: (3aR,6aR)-6a-Phenyl-tetrahydro-furo[3,4-c]isoxazol-6-one

: 6-oxo-6a-phenyltetrahydro-1H,3H-furo[3,4-c][1,2]oxazol-1-ium (7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methane sulfonate

Conditions

Conditions	Yield
In acetone at 20℃; Heating;	98%

: 480450-71-3
N-{(1R,2S,5S)-2-amino-5-[(dimethylamino)carbonyl]cyclohexyl}-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine-2-carboxamide

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

: C17H27N5O2S*C10H16O4S

Conditions

Conditions	Yield
In ethyl acetate at 50 - 65℃; for 0.00416667h;	98%

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

: tert-butyl 3-(bromoethynyl )azetidine-1-carboxylate

: 3-(bromoethynyl)azetidin-1-ium (+)-camphor-10-sulfonate

Conditions

Conditions	Yield
In cyclohexane; acetonitrile at 65 - 77℃;	98%

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

: 78-39-7
Triethyl orthoacetate

: 108481-13-6
D-camphorsulfonic acid ethyl ester

Conditions

Conditions	Yield
In dichloromethane for 0.5h; Ambient temperature;	97%

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

: 2488-14-4
N-(tert-butoxycarbonyl)-L-histidine methyl ester

: N(α)-tert-butoxycarbonyl-L-histidine methyl ester D-camphorsulfonate

Conditions

Conditions	Yield
In dichloromethane salt formation;	97%

: N-benzyl-4-trifluoromethyl-10-azatricyclo[6.3.1.0(2,7)]dodeca-2(7),3,5-triene

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

: N-benzyl-4-trifluoromethyl-10-azatricyclo[6.3.1.0(2,7)]dodeca-2(7),3,5-triene (+)-camphorsulfonic acid salt

Conditions

Conditions	Yield
In ethyl acetate; isopropyl alcohol at 20℃;	97%

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

: 120779-84-2
1,7-Diphenyl-3-oxa-2,7-diazabicyclo<3.3.0>octane

: 5,6a-diphenylhexahydro-1H-pyrrolo[3,4-c][1,2]oxazol-5-ium (7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methane sulfonate

Conditions

Conditions	Yield
In acetone at 20℃; Heating;	97%

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

: potassium (1S)-camphor-10-sulfonate

Conditions

Conditions	Yield
With potassium hydroxide In water	97%

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

: 21791-95-7
potassium (S)-camphorsulfonate

Conditions

Conditions	Yield
With potassium hydroxide In water at 20℃; for 12h;	96%

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

: 122-52-1
triethyl phosphite

: 108481-13-6
D-camphorsulfonic acid ethyl ester

Conditions

Conditions	Yield
at 50℃; for 2h; Inert atmosphere; Schlenk technique;	96%

: 591-80-0
pent-4-enoic acid

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

: 1199942-54-5
(tetrahydro-5-oxofuran-2-yl)methyl [(1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methansulfonate

Conditions

Conditions	Yield
With [bis(acetoxy)iodo]benzene In acetonitrile at 20℃; for 0.5h;	95%
With [bis(acetoxy)iodo]benzene; 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 24h;	83%
With [bis(acetoxy)iodo]benzene In tetrahydrofuran for 0.0333333h; ultrasound irradiation;	83%
With ammonium iodide; 3-chloro-benzenecarboperoxoic acid In 2,2,2-trifluoroethanol; acetonitrile at 20℃; for 24h;	42%

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

: 120779-84-2
1,7-Diphenyl-3-oxa-2,7-diazabicyclo<3.3.0>octane

: 5,6a-diphenylhexahydro-1H-pyrrolo[3,4-c][1,2]oxazol-1,5-diium (7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methane sulfonate

Conditions

Conditions	Yield
In acetone at 20℃; Heating;	95%

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.

Product Name

D-Camphorsulfonic acid

Synthetic route

D-Camphorsulfonic acid Consensus Reports

D-Camphorsulfonic acid Specification

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