(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
(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)
Safety
- Hazard Codes
- Xi
- Risk Statements
- 36/37/38
- Safety Statements
- 26-36-24/25
- WGK Germany
- 3
- F
- 10
- HS Code
- 29349990
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.
N-Bromosuccinimide Price
- Product number
- 349003
- Product name
- (1R)-(?)-(10-Camphorsulfonyl)oxaziridine
- Packaging
- 1g
- Price
- $188
- Updated
- 2025/07/31
- Product number
- C1327
- Product name
- (2S,8aR)-(-)-(Camphorylsulfonyl)oxaziridine [Asymmetric Oxidizing Reagent]
- Purity
- >95.0%(T)
- Packaging
- 1g
- Price
- $27
- Updated
- 2025/07/31
- Product number
- C1327
- Product name
- (2S,8aR)-(-)-(Camphorylsulfonyl)oxaziridine [Asymmetric Oxidizing Reagent]
- Purity
- >95.0%(T)
- Packaging
- 5g
- Price
- $79
- Updated
- 2025/07/31
- Product number
- C175095
- Product name
- (1R)-(-)-(10-Camphorsulfonyl)oxaziridine
- Packaging
- 50g
- Price
- $405
- Updated
- 2021/12/16
- Product number
- J97606
- Product name
- (1R)-(-)-(10-Camphorsulfonyl)oxaziridine
- Packaging
- 1g
- Price
- $20
- Updated
- 2021/12/16
(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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View Lastest Price from (1R)-(-)-(10-Camphorsulfonyl)oxaziridine manufacturers
- 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
- 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
- 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