13166-10-4

Basic information

• Product Name: ISOPROPYLIDENEMALONONITRILE
• Synonyms: 1,1-DICYANO-2-METHYL-1-PROPENE;ISOPROPYLIDENEMALONONITRILE;(1-Methylethylidene)malononitrile;1-Methylethylidenemalononitrile;2-Isopropylidenepropanedinitrile;2-(propan-2-ylidene)Malononitrile;2-Isopropylidene-malononitrile
• CAS NO: 13166-10-4
• Molecular Formula: C₆H₆N₂
• Molecular Weight: 106.13
• Product Categories: Dinitriles;Dinitriles & Trinitriles
• Mol File: 13166-10-4.mol
• Article Data: 40

Chemical Properties

• Boiling Point: 112°C 25mm
• Flash Point: 101°C
• Appearance: /
• Density: 0.96
• Vapor Pressure: 0.146mmHg at 25°C
• Refractive Index: 1.4680-1.4710
• Storage Temp.: Refrigerator
• Solubility: soluble in Methanol
• CAS DataBase Reference: ISOPROPYLIDENEMALONONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: ISOPROPYLIDENEMALONONITRILE(13166-10-4)
• EPA Substance Registry System: ISOPROPYLIDENEMALONONITRILE(13166-10-4)

Safety Data

• Statements: 23/24/25-36/37/38
• Safety Statements: 25-36/37/39
• RIDADR: 3276
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 13166-10-4(Hazardous Substances Data)

Usage

General Description

ISOPROPYLIDENEMALONONITRILE, also known as dimethyl malononitrile or DMMN, is a chemical compound with the formula C7H8N2. It is a colorless liquid that is used as a building block in organic synthesis, particularly in the production of pharmaceuticals and agrochemicals. ISOPROPYLIDENEMALONONITRILE is an important intermediate in the synthesis of pyridopyrimidine derivatives, which have been found to have various biological activities including antibacterial, antiviral, and anticancer properties. It is also used as a nucleophilic reagent in organic reactions due to the presence of the cyano group, and it can undergo various reactions to produce a variety of functionalized products. However, ISOPROPYLIDENEMALONONITRILE should be handled with caution as it is toxic and may cause skin and eye irritation.

InChI:InChI=1/C6H6N2/c1-5(2)6(3-7)4-8/h1-2H3

Upstream product

• 78386-09-1 1,1-dicyano-2,4-dimethyl-4-phenylpent-1-ene 
• 80982-69-0 dicyanomethylene-O,O-diethyl phosphorane 
• 67-64-1 acetone 
• 109-77-3 malononitrile 
• 107-95-9 3-amino propanoic acid 
• 917-54-4 methyllithium 
• 93102-10-4 dicyano-1,1 propadiene 
• 64-17-5 ethanol 
• 917-58-8 potassium ethoxide 
• 110-89-4 piperidine 
• 64-19-7 acetic acid 

Downstream Products

• 13017-67-9 3,3-dimethylcyclopropane-1,1,2,2-tetracarbonitrile 
• 102354-00-7 2-[(E)-3-(Ethyl-phenyl-amino)-1-methyl-allylidene]-malononitrile 
• 127877-45-6 β,β-dimethyl-α-(3-phenyl-1,2,4-oxadiazol-5-yl)acrylonitrile 
• 78386-14-8 1-phenyl-2,2-dicyano-1,3,3-trimethylcyclobutane 
• 78386-15-9 1-phenyl-3,3-dicyano-1,2,2-trimethylcyclobutane 
• 1135993-52-0 1-formyl-3,4,6,6-tetramethyl-3-cyclohexenecarbonitrile 
• 21448-31-7 1.1.1-Triphenyl-2.2-dicyan-3-methyl-butan 
• 16738-89-9 2-Butyl-2-methyl-cyclopropane-1,1-dicarbonitrile 
• 946-76-9 2-[(4-chlorophenyl)hydrazono]malononitrile 
• 133627-47-1 N-(2-chloro-4-methyl-3-pyridinyl)-2-(cyclopropylamino)-3-pyridinecarboxamide 
• 133627-45-9 3-Amino-2-chloro-4-methylpyridine 
• 152362-01-1 2-chloro-4-methyl-3-pyridinecarboxamide 

Relevant articles and documents

Investigating the continuous synthesis of a nicotinonitrile precursor to nevirapine

2-Chloro-3-amino-4-picoline (CAPIC) is a strategic building block for the preparation of nevirapine, a widely-prescribed nonnucleosidic reverse transcriptase inhibitor for the treatment of HIV-infected patients. A continuous synthesis to the bromo derivative of a CAPIC intermediate, 2-bromo-4- methylnicotinonitrile, that terminates in a dead-end crystallization is described. The route uses inexpensive, acyclic commodity-based raw materials and has the potential to enable lower cost production of nevirapine as well as other value added structures that contain complex pyridines. The route terminates in a batch crystallization yielding high purity CAPIC. This outcome is expected to facilitate regulatory implementation of the overall process.

Molybdenum hexacarbonyl-catalyzed condensation of malononitrile with ketones and aldehydes

Molybdenum hexacarbonyl activated with pyridine or morpholine catalyzes the condensation of malononitrile with ketones and aldehydes at 140 C, which leads to alkylidenemalononitriles in 75-100% yield.

Preparation of mesoporous carbon nitride materials using urea and formaldehyde as precursors and catalytic application as solid bases

A series of mesoporous carbon nitride materials have been fabricated using inexpensive and eco-friendly urea and formaldehyde as precursors and mesocellular silica foam (MCF) as a template through a nanocasting approach. Several techniques, including XRD, TEM, elemental analysis, FT-IR, XPS, and CO2-TPD have been applied to characterize the physicochemical properties of the mesoCN materials, and the results show that the materials possess high surface areas (331–355?m2?g?1), relatively concentrated pore size of ca. 6?nm, and abundant and multiple nitrogen-containing species. As heterogeneous base catalysts, mesoCN materials demonstrate high catalytic activity and selectivity in both Knoevenagel condensation and transesterification reactions.

Observations of tetrel bonding between sp3-carbon and THF

We report the direct observation of tetrel bonding interactions between sp3-carbons of the supramolecular synthon 3,3-dimethyl-tetracyanocyclopropane (1) and tetrahydrofuran in the gas and crystalline phase. The intermolecular contact is establishedvias-holes and is driven mainly by electrostatic forces. The complex manifests distinct binding geometries when captured in the crystalline phase and in the gas phase. We elucidate these binding trends using complementary gas phase quantum chemical calculations and find a total binding energy of -11.2 kcal mol-1for the adduct. Our observations pave the way for novel strategies to engineer sp3-C centred non-covalent bonding schemes for supramolecular chemistry.

Liquid-phase Knoevenagel reactions over modified basic microporous titanosilicate ETS-10

Al- and Ga-incorporated ETS-10, designated as ETAlS-10 and ETGaS-10, respectively, were synthesized by using P25 titania as a Ti source. The isomorphous substitution of Al and Ga for framework Si at the (4Si) environment was confirmed by 29Si M

Propargylamine-selective dual fluorescence turn-on method for post-synthetic labeling of DNA

We have developed a propargylamine-selective dual fluorescence turn-on system, using ylidenemalononitrile enamines, for post-synthetic DNA labeling, allowing the direct monitoring of DNA using dual emission in living cells.

Synthesis method of methylene malononitrile compounds

The invention discloses a synthesis method of methylene malononitrile compounds. According to the method, in the air atmosphere, a ketone compound and malononitrile are taken as raw materials, Ru/C istaken as a catalyst, the raw materials and the catalyst