D-Camphorsulfonic acid CAS#: 3144-16-9

By Janice Zhang,
D-Camphorsulfonic-acid
IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

英文名D-Camphorsulfonic acid
IUPAC Name[(1S,4R)-7,7-dimethyl-2-oxo-1-bicyclo[2.2.1]heptanyl]methanesulfonic acid
分子结构D-Camphorsulfonic-acid
CAS编号 3144-16-9
EINECS Number221-554-1
MDL NumberMFCD00064157
Beilstein Registry Number2809675
别名(1S)-10-camphorsulfonic acid, d-10-camphorsulfonic acid
分子式C10H16O4S
分子量232.301
InChIInChI=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)/t7-,10-/m1/s1
InChI KeyMIOPJNTWMNEORI-GMSGAONNSA-N
Canonical SMILESCC1(C2CCC1(C(=O)C2)CS(=O)(=O)O)C
Isomeric SMILESCC1([C@@H]2CC[C@]1(C(=O)C2)CS(=O)(=O)O)C
Patent Information
Patent IDTitlePublication Date
WO2018/170476POLYMORPHIC COMPOUNDS AND USES THEREOF2018
CN103509029Phenanthroquinolizidine Phenanthroindolizidine alkaloid derivatives and salts thereof and their preparation, anti-plant-virus and anti-cancer activity (by machine translation) 2016
US2013/150360INHIBITORS OF BRUTON’S TYROSINE KINASE 2013

Physical Data

AppearanceOff white crystalline powder
Alpha22 º (589nm, c=20, H2O 25 ºC)
Boiling Point100 °C
Refractive index21.5 ° (C=5, H2O)
SolubilityExhibit moderate Solubulity in HCCl.
PH0.3 (200g/l, H2O)
StabilityStable. Protect from moisture. Incompatible with strong oxidizing agents, strong bases.
SensitiveHygroscopic
Water SolubilitySoluble in water
Melting Point, °C Solvent (Melting Point)
196 – 200
194.9 – 195.8ethyl acetate
195acetic acid
197 – 198benzene
Description (Association (MCS))Solvent (Association (MCS))Temperature (Association (MCS)), °CPartner (Association (MCS))
Formation constant of a complexaq. phosphate buffer24.99β-cyclodextrin
Association with compoundCDCl3-60Dimethyl-(2-methyl-8-phenyl-quinolin-5-yl)-amine
Association with compoundCDCl3-60[8-(6-Methoxy-naphthalen-2-yl)-2-methyl-quinolin-5-yl]-dimethyl-amine
Association with compoundCDCl3-605-(Dimethylamino)-8-(3,5-diphenylphenyl)-2-methylquinoline
Dissociation Exponent (pK)Dissociation GroupSolvent (Dissociation Exponent)Type (Dissociation Exponent)
1.2SO2OHdichloromethanea1/apparent

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Temperature (NMR Spectroscopy), °CFrequency (NMR Spectroscopy), MHz
Chemical shifts1Hwater-d2300
Chemical shifts1H[D3]acetonitrile400
Chemical shifts 13CCDCl3
Chemical shifts33SH2O37
D-Camphorsulfonic acid CAS#: 3144-16-9NMR of D-Camphorsulfonic acid CAS 3144-16-9
Description (IR Spectroscopy)Solvent (IR Spectroscopy)
Spectrumpotassium bromide
D-Camphorsulfonic acid CAS#: 3144-16-9 IR1IR1 of D-Camphorsulfonic acid CAS 3144-16-9
D-Camphorsulfonic acid CAS#: 3144-16-9 IR2IR2 of D-Camphorsulfonic acid CAS 3144-16-9
Description (UV/VIS Spectroscopy)Solvent (UV/VIS Spectroscopy)
Spectrumethanol
SpectrumH2O
D-Camphorsulfonic acid CAS#: 3144-16-9 MS MS of D-Camphorsulfonic acid CAS 3144-16-9

Route of Synthesis (ROS)

Route of Synthesis (ROS) of D-Camphorsulfonic acid CAS 3144-16-9
Route of Synthesis (ROS) of D-Camphorsulfonic acid CAS 3144-16-9
ConditionsYield
With sulfuric acid; acetic anhydride

Safety and Hazards

Pictogram(s)corrosion
SignalDanger
GHS Hazard StatementsH290: May be corrosive to metals [Warning Corrosive to Metals]
H314: Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]
H318: Causes serious eye damage [Danger Serious eye damage/eye irritation]
Information may vary between notifications depending on impurities, additives, and other factors.
Precautionary Statement CodesP234, P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P390, P404, P405, and P501
(The corresponding statement to each P-code can be found at the GHS Classification page.)

Other Data

TransportationUN number: 2585; Class: 8; Packing group: III
Under the room temperature and away from light
HS Code294200
StorageUnder the room temperature and away from light
Shelf Life2 years
Market PriceUSD 60/kg
Use Pattern
(1S)-(+)-10-Camphorsulfonic acid may be used as a starting material to synthesize 10-iodocamphor. It may also be used as a dopant to induce chirality in the conduction band of polyaniline.(±)-S-methyl-S-phenylsulfoximine can be resolved using it as a chiral resolving agent to form the (-)-form in high enantiomeric purity.
Used as a resolving agent, as a catalyst for coupling dipeptides.

DL-10-CAMPHORSULFONIC ACID CAS#: 5872-08-2

By Janice Zhang,
DL-10-CAMPHORSULFONIC-ACID-CAS-5872-08-2
IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Other DataApproved Manufacturers

Identification

英文名DL-10-CAMPHORSULFONIC ACID
分子结构DL-10-CAMPHORSULFONIC-ACID-CAS-5872-08-2
CAS编号 5872-08-2
EINECS Number227-527-0
MDL NumberMFCD00074827
Beilstein Registry Number3205973
别名camphor-10-sulfonic acid, DL-10-camphorsulphonic acid, (7,7-dimethyl-2-oxobicyclo(2,2,1)heptan-1-yl)methanesulfonic acid, (7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonic acid, 7,7-dimethyl-2-oxobicyclo[2.2.1]-heptane-1-methanesulfonic acid, 10-camphorsulfonic acid||camphor-10-sulfonic acid||CSA||10-CSA, (±)-camphor-10-sulfonic acid
分子式C10H16O4S
分子量232.301
InChIInChI=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)/t7-,10+/m1/s1
InChI Key MIOPJNTWMNEORI-UHFFFAOYSA-N
Canonical SMILES CC1(C2CCC1(C(=O)C2)CS(=O)(=O)O)C
Patent Information
Patent IDTitlePublication Date
WO2008/145605IMPROVED SYNTHESIS OF (2S-CIS)-2-(BROMOMETHYL)-2-(4-CHLOROPHENYL)-1,3 DIOXOLANE-4-METHANOL METHANESULFONATE(ESTER) 2008
US2004/24254Process for preparation of optically active halogeno hydroxypropyl compound and glycidyl compound2004
US6348622Vitamin a related compounds and process for producing the same2002
US6372945Process for the synthesis of vinyl sulfoxides2002

Physical Data

AppearanceWhite or almost white crystalline powder
Melting Point 193~202 °C
Flash Point207.324°C
Boiling Point344.46°C (rough estimate)
Density1.2981 (rough estimate)
Water SolubilitySoluble in water
Refractive index1.5400 (estimate)
Description (Association (MCS))Comment (Association (MCS))Partner (Association (MCS))
IR spectrum of the complexfilmN,N-dimethyl-formamide
Further physical properties of the complexpolyacrylic acid, polyaniline; Monomer(s): aniline
Further physical properties of the complexpolyaniline

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Temperature (NMR Spectroscopy), °C Frequency (NMR Spectroscopy), MHz
Spectrum1Hchloroform-d1400
Spectrum13C[D3]acetonitrile26.84126
Description (IR Spectroscopy)Solvent (IR Spectroscopy)
SpectrumKBr

Route of Synthesis (ROS)

Route of Synthesis (ROS) of DL-10-CAMPHORSULFONIC ACID CAS 5872-08-2
Route of Synthesis (ROS) of DL-10-CAMPHORSULFONIC ACID CAS 5872-08-2
ConditionsYield
With sulfuric acid; acetic anhydride

Other Data

TransportationUN number: 3261; Class: 8; Packing group: II
Under the room temperature and away from light
HS Code294200
StorageUnder the room temperature and away from light
Shelf Life2 years
Market PriceUSD 60/kg
Use Pattern
Camphor-10-sulfonic acid (β) (CSA) is extensively used as an acid catalyst.
• It can be used in a catalytic amount to protect hydroxyl groups as tetrahydropyranyl (THP) ethers using dihydropyran.
• It also catalyzes the protection of ketones as ketals.
• It is a useful catalyst for the intramolecular ring opening of epoxides.
• CSA can also be used to catalyze nucleophile-promoted alkyne-iminium cyclization in the total synthesis of pumiliotoxin A.
starting material for manufacturing a composite catalyst suitable for making polyethylene terephthalate resin
Resolving agent
Camphorsulfonic acid is a organosulphur compound.