130995-62-9

Basic information

• Product Name: 2-(2-TERT-BUTYL-1,2-OXAZIRIDIN-3-YL)PHENOL
• Synonyms: 2-(2-TERT-BUTYL-1,2-OXAZIRIDIN-3-YL)PHENOL
• CAS NO: 130995-62-9
• Molecular Formula: C₁₁H₁₅NO₂
• Molecular Weight: 193.24
• Mol File: 130995-62-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 221.3±50.0 °C(Predicted)
• Appearance: /
• Density: 1.176±0.06 g/cm3(Predicted)
• PKA: 9.57±0.35(Predicted)
• CAS DataBase Reference: 2-(2-TERT-BUTYL-1,2-OXAZIRIDIN-3-YL)PHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-TERT-BUTYL-1,2-OXAZIRIDIN-3-YL)PHENOL(130995-62-9)
• EPA Substance Registry System: 2-(2-TERT-BUTYL-1,2-OXAZIRIDIN-3-YL)PHENOL(130995-62-9)

Safety Data

• Hazardous Substances Data: 130995-62-9(Hazardous Substances Data)

Usage

Chemical structure

2-(2-tert-butyl-1,2-oxaziridin-3-yl)phenol The compound is a phenol derivative with an oxaziridine ring attached to a phenol group.

Oxaziridine ring

A three-membered cyclic compound with one oxygen and two nitrogen atoms This ring structure is responsible for the compound's unique reactivity and properties.

Phenol derivative

Modified form of phenol The presence of the oxaziridine ring makes this compound a derivative of the parent compound, phenol.

Reagent in organic synthesis

Commonly used in organic reactions This compound is often employed as a reagent to facilitate various organic transformations.

Chiral auxiliary in asymmetric synthesis

Helps induce chirality in target molecules As a chiral auxiliary, this compound plays a crucial role in the synthesis of chiral molecules with high enantioselectivity.

Potential applications

Pharmaceutical and agrochemical industries The compound has been studied for its possible uses in these fields, which could lead to the development of new drugs and agrochemical products.

Unique structure and reactivity

Valuable and versatile in organic chemistry The combination of the oxaziridine ring and phenol group gives this compound a distinct set of properties, making it a useful tool in various organic chemistry applications.

Upstream product

• 26945-93-7 2-tert-butyliminomethylphenol 

Downstream Products

• 104883-60-5 α-(2-hydroxyphenyl)-N-tert-butylnitrone 
• 90-02-8 salicylaldehyde 

Relevant articles and documents

Rearrangement Reactions of Oxaziridines to Nitrones. X-Ray Crystal and Molecular Structure of N-t-Butyl-α(o-hydroxyphenyl)nitrone

Substituted N-benzylidene-t-butylamines are oxidized with m-chloroperoxybenzoic acid to oxaziridines which can rearrange to the corresponding nitrones when electron-donating groups are present in the phenyl ring.The oxaziridine-to-nitrone rearrangement, which has been considered as a 'pseudo-abnormal' reaction, can also be catalysed by Lewis acids.It has been found that the rearrangement of 2-t-butyl-3-(o-hydroxyphenyl)oxaziridine to the corresponding nitrone is of first order.The rearrangement has been investigated for different substituents in the phenyl ring, andin the case of 2-t-butyl-3-phenyloxaziridine substituted in the ortho position with electron-donating groups it has been found that the presence of protons of a Lewis acid is necessary.An X-ray structure of α-(o-hydroxyphenyl)-N-t-butylnitrone shows strong hydrogen bonding between the nitrone oxygen and the hydrogen in the hydroxy group.The oxaziridine-to-nitrone rearrangement is also analysed from a theoretical point of view using ab initio calculations.A Mulliken-population analysis of the C-O and N-O bonds in the oxaziridine ring for para-substitued 2-t-butyl-3-phenyloxaziridines shows a reduction of the C-O bond population when an electron-donating group is present in the para position of the phenyl ring compared with an electron-withdrawing group; the N-O bond populations show the reverse picture.A state-correlation diagram for the oxaziridine-to-nitrone rearrangement is also presented and the experimental and theoretical results support each other.