(2R)-Bornane-10,2-sultam Chemical Properties

Melting point:

183-185 °C

alpha 

-33 º (c=4.9, CHCl3)

Boiling point:

324.8±25.0 °C(Predicted)

Density 

1.1469 (rough estimate)

refractive index 

-31 ° (C=1, CHCl3)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform, Ethanol, Methanol

form 

Liquid

pka

11.05±0.40(Predicted)

color 

Clear colorless

optical activity

[α]19/D 32°, c = 5 in chloroform

Water Solubility 

Slightly soluble in water.

BRN 

83811

CAS DataBase Reference

94594-90-8(CAS DataBase Reference)

NIST Chemistry Reference

(-)-10,2-Camphorsultam(94594-90-8)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-36

WGK Germany 

3

HS Code 

29349990

MSDS

• Language:English Provider:(1S)-(-)-2,10-Camphorsultam
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(2R)-Bornane-10,2-sultam Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

(1S,2R)-(-)-10,2-Camphorsultam is used in the asymmetric synthesis of (S)- and (R)-N-Fmoc-S-trityl-α-methylcysteine. It is used as proton source in the synthesis of chiral α,γ-substituted γ-butyrolactones. It is also employed as a chiral probe for the optical resolution by HPLC and X-ray crystallographic determination of the absolute stereochemistry of carboxylic acids. Also used to prepare N-acryloyl derivatives which are employed as dienophiles in asymmetric Diels-Alder reactions. and for other asymmetric transformations.

Uses

(1S)-(?)-2,10-Camphorsultam may be used in the asymmetric synthesis of (S)- and (R)-N-Fmoc-S-trityl-α-methylcysteine. It may be used as proton source in the synthesis of chiral α,γ-substituted γ-butyrolactones.

Uses

(2R)-Bornane-10,2-sultam is a reagent used to make Camphorsultam conjugates.

General Description

(1S,2R,4R)-(?)-2,10-Camphorsultam may be employed as a chiral probe for the optical resolution by HPLC and X-ray crystallographic determination of the absolute stereochemistry of carboxylic acids.

Purification Methods

The (-)-enantiomer is recrystallised from 95% EtOH and dried in a vacuum desiccator. It dissolves in dilute aqueous NaOH and can be precipitated without hydrolysis by acidifying. It forms the N-Na salt in EtOH (by addition of Na to the EtOH solution), and the salt can be methylated with MeI to give the (-)-N-Me lactam with m 80o after recrystallisation from hot H2O and has []D -59.6o (c 5, CHCl3) [Shriner et al. J Am Chem Soc 60 2794 1938]. [Oppolzer et al. Helv Chim Acta 69 1142 1986, Weismiller et al. Org Synth 69 154 1955, Beilstein 27 III/IV 1007.]

(2R)-Bornane-10,2-sultam(94594-90-8)Related Product Information

• N-Acetylsulfanilyl chloride
• p-Toluenesulfonamide
• (1R)-(-)-10-Camphorsulfonic acid
• Dimethyl ether
• ETHANE
• Dimethyl phthalate
• Dimethyl sulfide
• Dimethyl fumarate
• Sulfanilamide
• N,N-Dimethylformamide
• (-)-CAMPHOR
• Benzenesulfonamide
• Dimethyl sulfoxide
• L(-)-10-Camphorsulfonyl chloride
• (1R,2R)-(-)-1,2-Diaminocyclohexane
• Ethyl (S)-9,10-difluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylate
• 3-METHOXY-DL-TYROSINE
• L(-)-Carvone