106268-97-7

Basic information

• Product Name: (2S,3S)-TRANS-3-METHYLOXIRANE-2-METHYL 4-NITROBENZOATE
• Synonyms: (2S,3S)-TRANS-3-METHYLOXIRANE-2-METHYL 4-NITROBENZOATE;(2S,3S)-(-)-3-METHYLGLYCIDYL 4 NITROBENZOATE;(2s,3s)-(-)-(2,3-epoxybutylester)-4-nitrobenzoate;3-methyl-,4-nitrobenzoate,(2s-trans)-oxiranemethano;3-methyloxiranemethanol4-nitrobenzoate(2s-trans)-;2,3-EPOXYBUTYLESTER-4-NITROBENZOATE;(2S,3S)-TRANS-3-METHYLOXIRANE-2-METHYL 4-NITROBENZOATE 97+%;3-methylglycidyl 4-nitrobenzoate
• CAS NO: 106268-97-7
• Molecular Formula: C₁₁H₁₁NO₅
• Molecular Weight: 237.21
• Mol File: 106268-97-7.mol

Chemical Properties

• Melting Point: 103-105 °C
• Boiling Point: 379.74°C (rough estimate)
• Flash Point: 178.3°C
• Appearance: /
• Density: 1.3350 (rough estimate)
• Vapor Pressure: 4.69E-06mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (2S,3S)-TRANS-3-METHYLOXIRANE-2-METHYL 4-NITROBENZOATE(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-TRANS-3-METHYLOXIRANE-2-METHYL 4-NITROBENZOATE(106268-97-7)
• EPA Substance Registry System: (2S,3S)-TRANS-3-METHYLOXIRANE-2-METHYL 4-NITROBENZOATE(106268-97-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: RR0510330
• F: 10-21
• Hazardous Substances Data: 106268-97-7(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(2S,3S)-TRANS-3-METHYLOXIRANE-2-METHYL 4-NITROBENZOATE is used as a reagent or intermediate for the synthesis of other organic molecules, leveraging its unique structural properties to facilitate the creation of new compounds with potential applications in various industries.
Used in Pharmaceutical Chemistry:
In the pharmaceutical industry, (2S,3S)-TRANS-3-METHYLOXIRANE-2-METHYL 4-NITROBENZOATE is utilized as a key intermediate in the development of pharmaceuticals. Its precise stereochemistry and substituent groups make it a valuable component in the synthesis of drugs with specific therapeutic targets, potentially leading to the discovery of novel medications.
Used in Research and Development:
(2S,3S)-TRANS-3-METHYLOXIRANE-2-METHYL 4-NITROBENZOATE is employed as a subject of study in research and development settings. Its unique structural features and potential applications in chemical and biological systems make it an intriguing candidate for exploration, with the aim of uncovering new insights and applications in various scientific fields.

InChI:InChI=1/C11H11NO5/c1-7-10(17-7)6-16-11(13)8-2-4-9(5-3-8)12(14)15/h2-5,7,10H,6H2,1H3/t7-,10-/m0/s1

Upstream product

• 504-61-0 (E)-but-2-enol 
• 122-04-3 4-nitro-benzoyl chloride 
• 50468-21-8 (2S,3S)-2,3-epoxy-1-butanol 

Relevant articles and documents

Asymmetric epoxidation of α,β-unsaturated aldehydes catalyzed by a spiro-pyrrolidine-derived organocatalyst

The asymmetric epoxidation of α,β-unsaturated aldehydes, catalyzed by a spiro-pyrrolidine (SPD)-derived organocatalyst, has been accomplished with good diastereoselectivities (up to dr >20:1) and with high to excellent enantioselectivities (up to 99% ee).

Catalytic Asymmetric Epoxidation and Kinetic Resolution: Modified Procedures Including in Situ Derivatization

The use of 3A or 4A molecular sieves ( zeoiltes ) substantially increases the scope of the titanium(IV)-catalyzed asymmetric epoxidation of primary allylic alcohols.Whereas without molecular sieves epoxidations employing only 5 to 10 mol percent Ti(O-i-Pr)4 generally led to low conversion or low enantioselectivity, in the presence of molecular sieves such reactions generally led to high conversion (>95percent) and high enantioselectivity (90-95percent ee).The epoxidations of 20 primary allylic alcohols are described.Especially noteworthy are the epoxidations of cinnamyl alcohol, 2-tetradecyl-2-propen-1-ol, allyl alcohol, and crotyl alcohol-compounds which heretofore had been considered difficult substrates for asymmetric epoxidation.In the case of allylic alcohol, the use of cumene hydroperoxide substantially increases both the reaction rate and the conversion, even in the absence of molecular sieves.In general, enantioselectivities are slightly depressed (by 1-5percent ee) relative to reactions employing 50-100 mol percent Ti(O-i-Pr)4.The epoxidation of low molecular weight allylic alcohols is especially facilitated and, in conjuction with in situ derivatization, provides for the synthesis of many epoxy alcohol synthons which were previously difficult to obtain.The kinetic resolution of four secondary allylic alcohols with 10 mol percent Ti(O-i-Pr)4 is also described.The role of molecular sieves in the reaction and the effects of variation in reaction stoichiometry, oxidant, and tartrate are discussed.