17109-93-2

Basic information

• Product Name: diethyl (cyanomethyl)propanedioate
• CAS NO: 17109-93-2
• Molecular Formula: C₉H₁₃NO₄
• Molecular Weight: 199.2038
• Mol File: 17109-93-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 307.7°C at 760 mmHg
• Flash Point: 133.4°C
• Density: 1.12g/cm³
• Vapor Pressure: 0.000711mmHg at 25°C
• Refractive Index: 1.443
• CAS DataBase Reference: diethyl (cyanomethyl)propanedioate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl (cyanomethyl)propanedioate(17109-93-2)
• EPA Substance Registry System: diethyl (cyanomethyl)propanedioate(17109-93-2)

Safety Data

• Hazardous Substances Data: 17109-93-2(Hazardous Substances Data)

Upstream product

• 107-16-4 glycolonitrile 
• 105-53-3 diethyl malonate 
• 68922-87-2 sodium 1,3-diethoxy-2-(ethoxycarbonyl)-1,3-dioxopropan-2-ide 
• 590-17-0 cyanomethyl bromide 
• 107-14-2 chloroacetonitrile 
• 996-82-7 sodium diethylmalonate 

Downstream Products

• 426835-40-7 diethyl 2-(2-iodo-3-phenylprop-3-enyl)-2-(cyanomethyl)propanedioate 
• 632-07-5 2-cyanopropanoic acid 
• 36821-26-8 2-oxopyrrolidine-3-carboxylic acid ethyl ester 

Relevant articles and documents

Preparation of mono-substituted malonic acid half oxyesters (SMAHOs)

The use of mono-substituted malonic acid half oxyesters (SMAHOs) has been hampered by the sporadic references describing their preparation. An evaluation of different approaches has been achieved, allowing to define the best strategies to introduce diversity on both the malonic position and the ester function. A classical alkylation step of a malonate by an alkyl halide followed by a monosaponification gave access to reagents bearing different substituents at the malonic position, including functionalized derivatives. On the other hand, the development of a monoesterification step of a substituted malonic acid derivative proved to be the best entry for diversity at the ester function, rather than the use of an intermediate Meldrum acid. Both these transformations are characterized by their simplicity and efficiency, allowing a straightforward access to SMAHOs from cheap starting materials.

Preparing method of 2,3-dicyanopropionate

The invention discloses a preparing method of 2,3-dicyanopropionate, which comprises: taking diethyl malonate and glycolonitrile as raw materials, reacting in a methanol solvent of sodium methoxide to obtain an intermediate I alpha-cyanmethyl-diethyl malonate, reacting the intermediate with ammonia gas in a methylbenzene solvent to obtain an intermediate II 2-acylamino-3-cyan ethyl propionate reaction solvent, and finally reacting the intermediate II reaction solvent with phosgene in presence of a catalyst 1,4-diazabicyclo[2.2.2]octane (DABCO for short) to obtain the product 2,3-dicyanopropionate. A highly toxic product of metal cyanide is not used as a raw material, alpha replaced (replacing hydrogen or olefinic bond, hydroxymethyl) cyanoacetic acid ester is not used as an initial raw material, the produced three wastes do not contain a metal cyanide highly toxic product and are low in processing difficulty, a recycled solvent can be used indiscriminately; an operation process is simple and safe and used raw materials are cheap and easy to obtain. A reaction yield is high, the product quality is high, the production cost is low, postprocessing is easy and easiness for industrialization is realized.

NOVEL HETEROCYCLES BY THE MALONIC ESTER VARIATION OF THE JAPP-KLINGEMANN REACTION

Azocompounds prepared by coupling malonic ester derivatives with diazotized anilines, 3-amino-2-chloropyridine, anthranilic ester or 2-aminobenzophenones are shown to be versatile intermediates for the synthesys of various polyaza-heterocycles.