106268-95-5

Basic information

• Product Name: (2R)-(-)-GLYCIDYL 4-NITROBENZOATE
• Synonyms: (2r)-(-)-(2,3-epoxypropylester)-4-nitrobenzoate;4-nitrobenzoate,(r)-oxiranemethano;(R)-(-)-GLYCIDYL-4-NITROBENZOATE;(2R)-(-)-GLYCIDYL 4-NITROBENZOATE;GLYCIDYL4-NITROBENZOATE;(R)-(-)-Oxirane-2-methanol 4-nitrobenzoate;(R)-(-)-Glycidyl 4-nitrobenzoate, (R)-(-)-Oxirane-2-methanol 4-nitrobenzoate
• CAS NO: 106268-95-5
• Molecular Formula: C₁₀H₉NO₅
• Molecular Weight: 223.18
• Mol File: 106268-95-5.mol

Chemical Properties

• Melting Point: 60-62 °C
• Boiling Point: 383.3°Cat760mmHg
• Flash Point: 187.5°C
• Appearance: /
• Density: 1.399g/cm³
• Vapor Pressure: 4.45E-06mmHg at 25°C
• Refractive Index: 1.584
• Storage Temp.: 2-8°C
• BRN: 5278590
• CAS DataBase Reference: (2R)-(-)-GLYCIDYL 4-NITROBENZOATE(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-(-)-GLYCIDYL 4-NITROBENZOATE(106268-95-5)
• EPA Substance Registry System: (2R)-(-)-GLYCIDYL 4-NITROBENZOATE(106268-95-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: RR0511000
• F: 10-21
• Hazardous Substances Data: 106268-95-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(2R)-(-)-GLYCIDYL 4-NITROBENZOATE is used as a starting material for the total synthesis of leukotriene B4, a potent inflammatory mediator involved in various physiological processes and diseases. Its synthesis enables the development of new therapeutic strategies targeting leukotriene B4-related pathways.
Used in Chemical Synthesis:
(2R)-(-)-GLYCIDYL 4-NITROBENZOATE serves as a key intermediate in the synthesis of various complex organic molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structural features allow for further functionalization and modification, making it a valuable building block in the development of novel compounds with diverse applications.

Purification Methods

Purify glycidol by fractional distillation.The 4-nitrobenzoates have m 56o (±); m 60-62o, [] D20 -37.9o (c 3.38 CHCl3) for R-(-)-isomer [106268-95-5];m 60-62o, [] D20 +38o (c 1 CHCl3) for the S-(+)-isomer [115459-65-9] and are recrystallised from Et2O or Et2O/pet ether (b 40-60o) [S-isomer: Burgos et al. J Org Chem 52 4973 1987, Sowden & Fischer J Am Chem Soc 64 1291 1942.] [Beilstein 17 I 50, 17 III/IV 985, 17/3 V 9.]

InChI:InChI=1/C10H9NO5/c12-10(16-6-9-5-15-9)7-1-3-8(4-2-7)11(13)14/h1-4,9H,5-6H2/t9-/m1/s1

Upstream product

• 122-04-3 4-nitro-benzoyl chloride 
• 107-18-6 allyl alcohol 
• 208838-21-5 ((2R,3R)-3-Triphenylsilanyl-oxiranyl)-methanol 
• 3847-57-2 sodium 4-nitrobenzoate 
• 106-89-8 epichlorohydrin 
• 13318-11-1 2-((4-nitrobenzoyloxy)methyl)oxirane 

Downstream Products

• 148519-83-9 (2R)-2-hydroxy-4-decynyl 4-nitrobenzoate 
• 97798-48-6 (S)-(2,3-dihydroxypropyl) phenyl sulfide 
• 106269-03-8 (S)-3-iodo-1,2-propanediol 1-O-p-nitrobenzoate 
• 106269-04-9 (R)-3-cyano-1,2-propanediol 1-O-p-nitrobenzoate 
• 61656-62-0 (2,2-dimethyl-1,3-dioxolane-4-yl)methyl p-nitrobenzoate 
• 60456-23-7 (S)-oxiranemethanol 
• 62-23-7 4-nitro-benzoic acid 
• 74628-84-5 (R)-glycerol mono-p-nitrobenzoate 
• 106269-05-0 (R)-3-cyano-1,2-propanediol bis(p-nitrobenzoate) 
• 121727-23-9 (S)-1-(4-Nitrobenzoyloxy)-2,3-propanediol 
• 38117-54-3 cyclopentadienyl iron(II) dicarbonyl dimer 
• 681490-95-9 (R)-2-chloro-1-[2-hydroxy-2-methyl-3-(4-nitrobenzoyloxy)]-propyl-4-nitroimidazole 
• 1337527-02-2 (R)-tert-butyl 2-(benzyloxycarbonylamino)-3-((S)-2,3-dihydroxypropylthio)propanoate 
• 148519-84-0 (2R)-2-<(tert-butyldiphenylsilyl)oxy>-4-decynyl 4-nitrobenzoate 

Relevant articles and documents

Novel synthesis and enzymatic resolution of (±)-2,3-epoxy propyl esters

A novel method of synthesizing glycidyl esters (±) -2,3-epoxy propyl esters has been developed involving reaction of epichlorohydrin with sodium salt of carboxylic acids in the presence of 15-crown-5 as catalyst with excellent yields. Enzymatic resolution of these glycidyl esters by lipasePS- C has been achieved with remarkable substrate selectivity.

Migration of aryl groups from silicon to carbon in α,β-epoxysilanes. A new model for hypervalent silicon study

The reaction of (2R,3R)-3-(triphenylsilyl)glycidol (1) with n-Bu4NF·3H2O in THF, followed by treatment of the product with p-nitrobenzoyl chloride yields (2S)-glycidol p-nitrobenzoate (4) and trans-cinnamyl p-nitrobenzoate (6) in a ratio of 1:1.5. The reaction of (R)Si-(2R,3R)- or (R)Si-(2S,3S)-3-[(methyl)(phenyl)(1-naphthyl)silyl]-glycidols, 7 or 8 respectively, with n-Bu4NF·3H2O affords mixtures of the respective glycidol, trans-cinnamyl alcohol and 3-(1-naphthyl)allyl alcohol. No significant difference in the product distribution in reaction of these two diasteromers was observed.

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.