13017-53-3

Basic information

• Product Name: 2-(1,2,2-TRIMETHYLPROPYLIDENE)MALONONITRILE
• Synonyms: 2-(1,2,2-TRIMETHYLPROPYLIDENE)MALONONITRILE;2-CYANO-3,4,4-TRIMETHYLPENT-2-ENENITRILE;(1,2,2-Trimethylpropylidene)malononitrile;2-(1,2,2-Trimethylpropylidene)propanedinitrile
• CAS NO: 13017-53-3
• Molecular Formula: C₉H₁₂N₂
• Molecular Weight: 148.2
• Mol File: 13017-53-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 244.1°Cat760mmHg
• Flash Point: 98.6°C
• Appearance: /
• Density: 0.943g/cm³
• Vapor Pressure: 0.031mmHg at 25°C
• Refractive Index: 1.463
• CAS DataBase Reference: 2-(1,2,2-TRIMETHYLPROPYLIDENE)MALONONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(1,2,2-TRIMETHYLPROPYLIDENE)MALONONITRILE(13017-53-3)
• EPA Substance Registry System: 2-(1,2,2-TRIMETHYLPROPYLIDENE)MALONONITRILE(13017-53-3)

Safety Data

• Hazardous Substances Data: 13017-53-3(Hazardous Substances Data)

Usage

General Description

2-(1,2,2-Trimethylpropylidene)malononitrile is a chemical compound with the molecular formula C11H16N2. It is also known as "Meldrum's Acid" and is commonly used as a precursor in organic synthesis for the preparation of various compounds. It is a versatile building block in organic chemistry and is often used in the formation of heterocycles and pharmaceuticals. Meldrum's Acid is also used as a reagent in the synthesis of other complex molecules and has a wide range of applications in the fields of medicinal chemistry, material science, and agrochemicals.

InChI:InChI=1/C9H12N2/c1-7(9(2,3)4)8(5-10)6-11/h1-4H3

Upstream product

• 75-97-8 3,3-dimethyl-butan-2-one 
• 109-77-3 malononitrile 
• 17380-91-5 thiopinacolone 
• 22150-66-9 4-tert-butyl-4,5-dihydro-pyrazole-3,3-dicarbonitrile 
• 76-09-5 2,3-dimethyl-2,3-butane diol 

Downstream Products

• 42009-35-8 (Z)-2-Aminomethyl-3,4,4-trimethyl-pent-2-enenitrile 
• 75-97-8 3,3-dimethyl-butan-2-one 
• 109-77-3 malononitrile 
• 1380808-75-2 [5-(tert-butyl)selenopheno[3,2-e]pyrimidin-4-yl](3-chloro-4-fluorophenyl)amine 

Relevant articles and documents

Synthesis and Reactivity Profile of Ylidenemalononitrile Enamines and Their Ester Analogs Towards Electrophiles and Nucleophiles

Herein, we describe the synthesis and reactivity of enamines derived from ylidenemalononitriles and ylidenecyanoacetates. The enamine scope was expanded by (1) increasing yields of aldehyde-derived ylidenemalononitriles, (2) incorporating silyl functional

A convenient and selective one-pot method for the synthesis of monosubstituted secondary alkyl malononitriles

We have found that α,α-dicyanoalkenes can be efficiently and selectively reduced to α,α-dicyanoalkanes (malononitriles) with NaBH4 in 95% EtOH at 0 °C. In addition, we have determined that the condensation of malononitrile with ketones using absorption alumina as a catalyst can be followed directly, in one pot, by reduction with NaBH 4 in 95% EtOH at 0 °C to provide the monosubstituted secondary alkyl malononitriles in good to excellent yields (42-94%). This procedure provides a convenient alternative to direct alkylation of malononitrile or reduction of α,α-dicyanoalkene intermediates.

Geminal dinitriles and their reactions: I. Hydrolysis of alkylidene- and cycloalkylidenemalononitriles in aqueous medium

The kinetics of pseudounimolecular hydrolysis of alkylidene- and cycloalkylidenemalononitriles in an aqueous buffer at pH 7 were studied. Correlations between the rate constants and substituent effects were found to fit the Taft-Hancock equation. Electrochemical reduction of alkylidenemalononitriles was studied using 0.2 M tetraethylammonium iodide as supporting electrolyte. The half-wave reduction potentials are related to the substituent constants σ* by the Taft-Zuman equation. Anomalous behavior of 1,1-dicyano-2,3,3-trimethyl-1-butene was observed during the hydrolysis and electrochemical reduction at a dropping mercury electrode.