603-67-8

Basic information

• Product Name: Diethyl nitromalonate
• Synonyms: DIETHYL NITROMALONATE;2-Nitromalonic acid diethyl;Nitromalonic acid diethyl ester;2-nitromalonic acid diethyl ester;diethyl 2-nitropropanedioate;diethyl 2-nitromalonate;Diethyl nitromalonate 97%
• CAS NO: 603-67-8
• Molecular Formula: C₇H₁₁NO₆
• Molecular Weight: 205.17
• EINECS: 210-052-8
• Product Categories: Pharmaceutical Intermediates;C6 to C7;Carbonyl Compounds;Esters
• Mol File: 603-67-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 78-80 °C0.2 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: COLORLESS TO YELLOW LIQUID
• Density: 1.174 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00247mmHg at 25°C
• Refractive Index: n20/D 1.428(lit.)
• Storage Temp.: 2-8°C
• PKA: 6.46±0.59(Predicted)
• CAS DataBase Reference: Diethyl nitromalonate(CAS DataBase Reference)
• NIST Chemistry Reference: Diethyl nitromalonate(603-67-8)
• EPA Substance Registry System: Diethyl nitromalonate(603-67-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 603-67-8(Hazardous Substances Data)

Usage

Uses

Diethyl nitromalonate has been used in the preparation of 5,5-diethoxycarbonyl-1-pyrroline N-oxide (DECPO).

Synthesis Reference(s)

Journal of the American Chemical Society, 77, p. 4391, 1955 DOI: 10.1021/ja01621a060

General Description

Thermal decomposition of diethyl nitromalonate to furoxan has been studied.

InChI:InChI=1/C7H11NO6/c1-3-13-6(9)5(8(11)12)7(10)14-4-2/h5H,3-4H2,1-2H3

Upstream product

• 7697-37-2 nitric acid 
• 105-53-3 diethyl malonate 
• 64-19-7 acetic acid 
• 108-24-7 acetic anhydride 
• 7647-01-0 hydrogenchloride 
• 856327-17-8 cyano-nitro-acetic acid ethyl ester 
• 421-17-0 Trifluoromethylsulfenyl chloride 
• 42065-95-2 bromo-nitro-malonic acid diethyl ester 
• 6829-41-0 diethyl oximinomalonate 
• 40561-27-1 1-cyano-1-methylethylnitrate 
• 996-82-7 sodium diethylmalonate 
• 64-17-5 ethanol 

Downstream Products

• 4591-86-0 2-(2-Nitroethyl)cyclohexanone 
• 626-35-7 nitroacetic acid ethyl ester 
• 6829-40-9 aminomalonic acid diethyl ester 
• 14011-21-3 2-nitroacetamide 
• 51-79-6 urethane 
• 1979-97-1 2-(methylthio)-5-nitropyrimidine-4,6-diol 
• 57-13-6 urea 
• 105-53-3 diethyl malonate 
• 119367-04-3 ethyl 2-(4',6'-di-O-benzyl-2',3'-dideoxy-β-D-erythro-hex-2'-enopyranosyl)-2-nitro-2-(ethoxycarbonyl)acetate 
• 119367-03-2 ethyl 2-(4',6'-di-O-benzyl-2',3'-dideoxy-α-D-erythro-hex-2'-enopyranosyl)-2-nitro-2-(ethoxycarbonyl)acetate 
• 80466-56-4 2-amino-5-nitropyrimidine-4,6-diol 
• 102154-59-6 2--2-nitro-malonsaeure-diaethylester 
• 680-42-2 diethyl 2-fluoro-2-nitromalonate 
• 10477-63-1 <4.4'-Bis-dimethylamino-benzhydryl>-nitro-malonsaeure-diethylester 

Relevant articles and documents

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The Synthesis and Application of Novel Nitrating And Nitrosating Agents

Alcohols and phenols are efficiently nitrated with thionyl chloride nitrate or thionyl nitrate, even in the presence of an aromatic moiety.While thionyl chloride nitrate is suitable for nitration of primary OH-groups in carbohydrates, thionyl nitrate is reactive enough to react with secondary OH-groups as well.These reagents permit the highly selective nitration of the 5'-, 2',5'- and 3',5'-OH-groups of ribonucleosides to produce either mono- or diprotected nitro derivatives in high yields.Carbon acids and the enol form of some ketones are efficiently nitrated with trifluoromethanesulfonyl nitrate/potassium tert-butoxide.Lutidine N-oxide(2,6-(CH3)2C5H3N->O) was found to have marked effect on nitration reactions.Similarly, thionyl chloride nitrite and thionyl nitrite exhibit an excellent capacity for nitrosation of the aforementioned substrates