ChemicalBook > CAS DataBase List > (1R)-(-)-(10-Camphorsulfonyl)oxaziridine

(1R)-(-)-(10-Camphorsulfonyl)oxaziridine

Product Name
(1R)-(-)-(10-Camphorsulfonyl)oxaziridine
CAS No.
104372-31-8
Chemical Name
(1R)-(-)-(10-Camphorsulfonyl)oxaziridine
Synonyms
(-)-CAMPHORSULFONYLOXAZIRIDINE;(10-camphorsulfonyl)oxaziridine;R-(10-Camphorsulfonyl)oxaziridine;(R)-2,N-EPOXY-EXO-10,2-BORNANESULTAM;(-)-((CAMPHORYL) SULFONYL)OXAZIRIDINE;(1R)-(-)-(CAMPHORYLSULFONYL)OXAZIRIDINE;(1R)-(-)-(10-Camphorsulfonyl)oxaziridin;(1R)-(-)-(10-CAMPHORSULFONYL)OXAZIRIDINE;(1R)-(-)-2,N-EPOXY-EXO-10,2-BORNANESULTAM;(1R)-(-)-(10-CAMPHORSULPHONYL)OXAZIRIDINE
CBNumber
CB9768000
Molecular Formula
C10H15NO3S
Formula Weight
229.3
MOL File
104372-31-8.mol
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(1R)-(-)-(10-Camphorsulfonyl)oxaziridine Property

Melting point:
170-174 °C
alpha 
-46.6 º (c=2, CHCl3 25 ºC)
Boiling point:
317.6±25.0 °C(Predicted)
Density 
1.2486 (rough estimate)
refractive index 
1.5060 (estimate)
Flash point:
170℃
storage temp. 
2-8°C
solubility 
Chloroform (Slightly), Methanol (Slightly)
pka
-11.75±0.40(Predicted)
form 
Powder
color 
White
optical activity
[α]20/D 44°, c = 2.2 in chloroform
BRN 
6274369
InChI
InChI=1/C10H15NO3S/c1-8(2)7-3-4-9(8)6-15(12,13)11-10(9,5-7)14-11/h7H,3-6H2,1-2H3/t7-,9-,10?,11?/s3
InChIKey
GBBJBUGPGFNISJ-SENRVMEJNA-N
SMILES
C123C[C@@]4([H])CC[C@@]1(CS(=O)(=O)N2O3)C4(C)C |&1:2,6,r|
CAS DataBase Reference
104372-31-8(CAS DataBase Reference)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-36-24/25
WGK Germany 
3
10
HS Code 
29349990
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
349003
Product name
(1R)-(?)-(10-Camphorsulfonyl)oxaziridine
Packaging
1g
Price
$188
Updated
2025/07/31
TCI Chemical
Product number
C1327
Product name
(2S,8aR)-(-)-(Camphorylsulfonyl)oxaziridine [Asymmetric Oxidizing Reagent]
Purity
>95.0%(T)
Packaging
1g
Price
$27
Updated
2025/07/31
TCI Chemical
Product number
C1327
Product name
(2S,8aR)-(-)-(Camphorylsulfonyl)oxaziridine [Asymmetric Oxidizing Reagent]
Purity
>95.0%(T)
Packaging
5g
Price
$79
Updated
2025/07/31
TRC
Product number
C175095
Product name
(1R)-(-)-(10-Camphorsulfonyl)oxaziridine
Packaging
50g
Price
$405
Updated
2021/12/16
AK Scientific
Product number
J97606
Product name
(1R)-(-)-(10-Camphorsulfonyl)oxaziridine
Packaging
1g
Price
$20
Updated
2021/12/16
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(1R)-(-)-(10-Camphorsulfonyl)oxaziridine Chemical Properties,Usage,Production

Chemical Properties

White crystalline powder

Uses

Reactant involved in:

  • Asymmetric synthesis of proton pump inhibitors
  • Asymmetric synthesis of polyhydroxylated pyrrolidines
  • Diastereoselective hydroxylation of chlorophylls a and b enolate anions

Used in impregnated silica nanoparticles for removal of sulfur mustard from wastewater

Used to modify blebbistatin for investigations of myosin inhibitor design

Uses

(1R)-(-)-(10-Camphorsulfonyl)oxaziridine is a useful synthetic intermediate. Used for asymmetric hydroxylation.

Synthesis

The enantiopure (1S)-(+)-(Camphorylsulfonyl)oxaziridine and (1R)-(-)-(10-Camphorsulfonyl)oxaziridine and [(8,8- dichlorocamphor)sulfonyl]oxaziridines (2) are commercially available. They can also be prepared on a large scale via the oxidation of corresponding camphorsulfonimines with buffered Potassium Monoperoxysulfate (Oxone) or buffered peracetic acid. Since oxidation takes place from the endo face of the C=N double bond, only a single oxaziridine isomer is obtained. The precursor camphorsulfonimines can be prepared in 3 steps (>80% yield) from inexpensive (+)- and (-)-10-Camphorsulfonic Acids. A variety of (camphorylsulfonyl)oxaziridine derivatives such as (2)-(4) are also readily available via the functionalization of the camphorsulfonimines followed by oxidation.

Synthesis

(1R)-(-)-(10-Camphorsulfonyl)oxaziridine is a neutral, aprotic, electrophilic, and asymmetric oxidizing agents for the chemoselective oxidation of many nucleophilic substrates such as sulfides, enamines, enol esters, carbanions, and enolates.

References

1. Mergelsberg, I.; Gala, D.; Scherer, D.; DiBenedetto, D.; Tanner TL 1992, 33, 161.
2. Davis, F. A.; Kumar, A.; Chen, B.-C. JOC 1991, 56, 1143.
3. Chen, B.-C.; Weismiller, M. C.; Davis, F. A.; Boschelli, D.; Empfield, J. R.; Smith, III, A. B. T 1991, 47, 173.

(1R)-(-)-(10-Camphorsulfonyl)oxaziridine Preparation Products And Raw materials

Raw materials

Preparation Products

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(1R)-(-)-(10-Camphorsulfonyl)oxaziridine Suppliers

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View Lastest Price from (1R)-(-)-(10-Camphorsulfonyl)oxaziridine manufacturers

Hebei Chuanghai Biotechnology Co., Ltd
Product
(1R)-(-)-(10-Camphorsulfonyl)oxaziridine 104372-31-8
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-12-02
Aromsyn Co., Ltd.
Product
(1R)-(-)-(10-Camphorsulfonyl)oxaziridine 104372-31-8
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
kgs
Release date
2023-02-17
Career Henan Chemical Co
Product
(1R)-(-)-(10-Camphorsulfonyl)oxaziridine 104372-31-8
Price
US $1.00/KG
Min. Order
1KG
Purity
98%
Supply Ability
20KG
Release date
2018-08-07

104372-31-8, (1R)-(-)-(10-Camphorsulfonyl)oxaziridineRelated Search:


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  • 104372-31-8
  • Oxidation
  • Bicyclic Monoterpenes
  • Terpenes
  • Sulfur Compounds (for Synthesis)
  • Asymmetric Synthesis
  • Chiral Catalysts, Ligands, and Reagents
  • Hydroxylation
  • Biochemistry
  • Oxidation
  • Sulfur Compounds (for Synthesis)
  • Synthetic Organic Chemistry
  • Terpenes
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Asymmetric Synthesis
  • Bicyclic Monoterpenes
  • chiral
  • Chiral Reagents