115459-65-9

Basic information

• Product Name: (2S)-(+)-GLYCIDYL 4-NITROBENZOATE
• Synonyms: (S)-(+)-GLYCIDYL-4-NITROBENZOATE;(2s)-(+)-(2,3-epoxypropylester)-4-nitrobenzoate;4-nitrobenzoate,(s)-oxiranemethano;(2S)-(+)-GLYCIDYL 4-NITROBENZOATE;(2S)-(+)-Glycidyl 4-nitr0benzoate;4-17-00-01007 (Beilstein Handbook Reference);2,3-EPOXYPROPYLESTER-4-NITROBENZOATE;(S)-(+)-Glycidyl 4-nitrobenzoate, (S)-(+)-Oxirane-2-methanol 4-nitrobenzoate
• CAS NO: 115459-65-9
• Molecular Formula: C₁₀H₉NO₅
• Molecular Weight: 223.18
• Mol File: 115459-65-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 60-62 °C(lit.)
• Boiling Point: 383.3°Cat760mmHg
• Flash Point: 187.5°C
• Appearance: /
• Density: 1.399g/cm³
• Storage Temp.: 2-8°C
• BRN: 87687
• CAS DataBase Reference: (2S)-(+)-GLYCIDYL 4-NITROBENZOATE(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-(+)-GLYCIDYL 4-NITROBENZOATE(115459-65-9)
• EPA Substance Registry System: (2S)-(+)-GLYCIDYL 4-NITROBENZOATE(115459-65-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• RTECS: RR0511020
• F: 10-21
• Hazardous Substances Data: 115459-65-9(Hazardous Substances Data)

Usage

Purification Methods

Purify glycidol by fractional distillation.The 4-nitrobenzoates have m 56o (±); m 60-62o, [] D 20 -37.9o (c 3.38 CHCl3) for R-(-)-isomer [106268-95-5];m 60-62o, [] D 20 +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.] Gramine.

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-/m0/s1

Upstream product

• 57044-25-4 (R)-oxiranemethanol 
• 62-23-7 4-nitro-benzoic acid 
• 121727-23-9 (S)-1-(4-Nitrobenzoyloxy)-2,3-propanediol 
• 121727-22-8 3-Hydroxy-1-(4-nitrobenzoyloxy)propanone 
• 122-04-3 4-nitro-benzoyl chloride 
• 3847-57-2 sodium 4-nitrobenzoate 
• 106-89-8 epichlorohydrin 
• 121727-24-0 (S)-1-(4-Nitrobenzoyloxy)-3-tosyloxy-2-propanol 
• 107-18-6 allyl alcohol 

Downstream Products

• 1337527-57-7 (R)-tert-butyl 2-(benzyloxycarbonylamino)-3-((R)-2,3-dihydroxypropylthio)propanoate 
• 57044-25-4 (R)-oxiranemethanol 
• 62-23-7 4-nitro-benzoic acid 

Relevant articles and documents

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Nonsymmetrical azocarbonamide carboxylates as effective Mitsunobu reagents

A family of nonsymmetrical Mitsunobu reagents possessing both dialkyl amide and ester substituents was developed. These new reagents were readily prepared in a single pot from inexpensive, commercially available materials by using a scalable and environmentally friendly procedure. They were shown to exhibit activity parallel to that of diethyl azodicarboxylate/diisopropyl azodicarboxylate in a wide variety of Mitsunobu reactions. Importantly, the acyl hydrazine reaction byproducts were readily separable from the crude mixture by standard aqueous workup. In addition, the discovery of effective nonsymmetrical Mitsunobu reagents offers new directions for the ongoing development of this important reaction.

Enatioselective Microbial Reduction of Monoesters of 1,3-Dihydroxypropanone: Synthesis of (S)- and (R)-1,2-O-Isopropylideneglycerol

The reduction of 3-benzoyloxy-1-hydroxypropanone with bakers' yeast proceeds enantioselectively to afford (S)-3-benzoyloxy-1,2-propanediol, which may be further converted into (S)-(benzoyloxymethyl)oxirane.The bioreduction with fermenting yeast of 1-acetoxy-3-benzyloxypropanones gives (R)-1-benzyloxy-3-acetoxy-2-propanol which can be used for the preparation of both (S)- and (R)-1,2-O-isopropylideneglycerol.