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

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(2R)-Bornane-10,2-sultam Basic information

Product Name:
(2R)-Bornane-10,2-sultam
Synonyms:
  • (-)-EXO-10,2-BORNANESULTAM
  • (-)-D-2,10-CAMPHORSULTAM
  • (-)-D-2,10-CAMPHOSULTAM
  • D(-)-10,2-CAMPHORSULTAME
  • (2R)-BORNANE-10,2-SULTAM
  • (1S)-(-)-2,10-CAMPHORSULTAM
  • (1S)-2,10-CAMPHORSULTAM
  • (1S,2R)-(-)-2,10-CAMPHORSULTAM
CAS:
94594-90-8
MF:
C10H17NO2S
MW:
215.31
Product Categories:
  • Chiral Reagents
  • Sulfur & Selenium Compounds
  • chiral
  • Asymmetric Synthesis
  • Bicyclic Monoterpenes
  • Biochemistry
  • Sulfur Compounds (for Synthesis)
  • Synthetic Organic Chemistry
  • Terpenes
  • Peptide
Mol File:
94594-90-8.mol
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(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)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-37/39-36
WGK Germany 
3
HS Code 
29349990

MSDS

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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.]

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