5400-68-0

Basic information

• Product Name: DIHYDROFURAN-2,3-DIONE 3-OXIME
• Synonyms: DIHYDROFURAN-2,3-DIONE 3-OXIME
• CAS NO: 5400-68-0
• Molecular Formula: C₄H₅NO₃
• Molecular Weight: 115.09
• Mol File: 5400-68-0.mol

Chemical Properties

• Boiling Point: 238.6°Cat760mmHg
• Flash Point: 98.1°C
• Appearance: /
• Density: 1.55g/cm³
• Vapor Pressure: 0.00744mmHg at 25°C
• Refractive Index: 1.58
• CAS DataBase Reference: DIHYDROFURAN-2,3-DIONE 3-OXIME(CAS DataBase Reference)
• NIST Chemistry Reference: DIHYDROFURAN-2,3-DIONE 3-OXIME(5400-68-0)
• EPA Substance Registry System: DIHYDROFURAN-2,3-DIONE 3-OXIME(5400-68-0)

Safety Data

• Hazardous Substances Data: 5400-68-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C4H5NO3/c6-4-3(5-7)1-2-8-4/h7H,1-2H2

Upstream product

• 517-23-7 3-acetyl-2-oxo-4,5-dihydrofuran 
• 109-95-5 ethyl nitrite 
• 4360-91-2 α-carboxy-γ-butyrolactone 
• 118633-87-7 dihydro-furan-2,3-dion-3-(O-acetyl oxime ) 
• 96-48-0 4-butanolide 
• 263840-05-7 [(E)-Trityloxyimino]-acetic acid 2-bromo-ethyl ester 
• 51425-66-2 (4,5-dihydro-2-furanyloxy)(trimethyl)silane 
• 7664-93-9 sulfuric acid 
• 7647-01-0 hydrogenchloride 
• 67-56-1 methanol 
• 871886-90-7 (2-bromo-ethyl)-malonic acid 

Downstream Products

• 4374-64-5 dihydrofuran-2,3-dione 
• 1192-20-7 2-aminobutyrolactone 
• 7803-49-8 hydroxylamine 

Relevant articles and documents

Synthesis method of 2-amino-gamma-butyrolactone hydrochloride

The invention discloses a synthesis method of 2-amino-gamma-butyrolactone hydrochloride (I) for a kind of important chemical, dye, pesticide and medical intermediates. The synthesis method includes the following steps: taking a gamma-butyrolactone compound (II) and a nitroso ester compound (III) as raw materials to react with each other to obtain 2-(hydroxyl imino)-gamma-butyrolactone (IV), and subjecting the compound (IV) to reduction reaction and acidification to obtain the 2-amino-gamma-butyrolactone hydrochloride (I). The method used for preparing the product compound (I) is mild in condition, simple to operate, high in yield, low in environmental pollution, easier for industrial production and the like.

Metal nitrite: A powerful oxidizing reagent

An efficient and simple source of nitroso reagents and their oxidation reactions are described. The combination of a Lewis acid and a metal nitrite was applied to the oxidation of silyl enol ethers. Amino acid and peptide derivatives were easily accessed through in situ C-C bond cleavage of fully substituted silyl enol ethers upon oxidation.

A tin hydride designed to facilitate removal of tin species from products of stannane-mediated radical reactions

The stannane 1, which is simple to prepare, behaves like the conventional reagents Bu3SnH and Ph3SnH in standard free radical reactions, but with the special characteristic that the tin-containing byproducts are easily and very largely removed by mild hydrolysis (LiOH-water-THF or TsOH-water-THF), which converts them into base-soluble (aqueous NaHCO3) materials. The performance of stannane 1 was evaluated for a range of radical reactions involving halides, selenides, Barton-McCombie deoxygenation, and enyne cyclization. In several cases the effectiveness of the workup procedure in removing tin species was monitored by 1H NMR.

Radical cyclization of O-trityl oximino esters: A ring closure that preserves the oxime function

O-Trityl oximino esters 1 undergo stannane-induced radical cyclization to regenerate an oxime function, affording oximino lactones 4; these can be converted into enamides (e.g. 11b), and such a transformation was used to make the natural product 14c.