1202-48-8

Basic information

• Product Name: 2-(anilinomethylene)malononitrile
• Synonyms: 2-(anilinomethylene)malononitrile;2-(anilinomethylidene)propanedinitrile;2-[(phenylamino)methylidene]propanedinitrile
• CAS NO: 1202-48-8
• Molecular Formula: C₁₀H₇N₃
• Molecular Weight: 169.18268
• Mol File: 1202-48-8.mol
• Article Data: 16

Chemical Properties

• Melting Point: 245 °C
• Boiling Point: 300.6°Cat760mmHg
• Flash Point: 135.6°C
• Appearance: /
• Density: 1.22g/cm³
• Vapor Pressure: 0.00111mmHg at 25°C
• Refractive Index: 1.632
• PKA: -2.77±0.70(Predicted)
• CAS DataBase Reference: 2-(anilinomethylene)malononitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(anilinomethylene)malononitrile(1202-48-8)
• EPA Substance Registry System: 2-(anilinomethylene)malononitrile(1202-48-8)

Safety Data

• Hazardous Substances Data: 1202-48-8(Hazardous Substances Data)

Usage

Physical state

Bright yellow solid

Common uses

Organic synthesis, chemical research

Functional groups

Aniline group, malononitrile group

Known for

Reactivity in various reactions

Usage

Precursor for the synthesis of various organic compounds (e.g. pharmaceuticals, dyes, specialty chemicals)

Field of study

Organic chemistry

InChI:InChI=1/C10H7N3/c11-6-9(7-12)8-13-10-4-2-1-3-5-10/h1-5,8,13H

Upstream product

• 122-51-0 orthoformic acid triethyl ester 
• 62-53-3 aniline 
• 109-77-3 malononitrile 
• 91255-20-8 N,N-Dimethyl-N'-(α-cyano-β-N'-anilinoacrylyl)formamidine 
• 1783-25-1 N₁,N₁-dimethyl-N₂-phenylformamidine 
• 149-73-5 trimethyl orthoformate 
• 80420-96-8 α-Cyano-β-anilinoacrylamide 
• 997-76-2 tricyanoethene 
• 123-06-8 Ethoxymethylenemalononitrile 

Downstream Products

• 112124-35-3 sodium 6-amino-3,5-dicyanopyridine-2-thiolate 
• 59021-52-2 [(2,2-Dicyano-vinyl)-phenyl-amino]-acetic acid ethyl ester 
• 59021-50-0 2-{[(2-Oxo-2-phenyl-ethyl)-phenyl-amino]-methylene}-malononitrile 
• 158591-06-1 2-Amino-4H-pyrazolo<1,5-a>benzimidazol-3-carbonitril 
• 52832-04-9 N-(trichloromethylthio)anilinomethylenemalononitrile 

Relevant articles and documents

Solvent-free synthesis of quinolone derivatives

Quinolones can be prepared in a three step procedure from triethylorthoformate and activated methylene derivatives leading to alkoxymethylenemalonates followed by reaction with aromatic amines and finally a cyclization. All the reactions were carried out under solvent-free conditions possibly under microwave activation with benefits for the first step.

One Pot Synthesis of 3-Amino-1H-pyrazole-4-carbonitrile

Condensation of malodinitrile with trimethoxymethan and aniline affords 3-anilino-2-cyanoacrylonitrile, which on treatment with hydrazine gives the title compound.Aniline can be recovered almost quantitatively. Keywords: Enaminonitrile; Amine exchange; Cyclisation

Triflic acid-mediated N-heteroannulation of β-anilino-β-(methylthio)acrylonitriles: a facile synthesis of 4-amino-2-(methylthio)quinolines

Various functionalised 4-amino-2-(methylthio)quinolines are synthesised through triflic acid-mediated N-heteroannulation of α-functionalized-β-anilino-β-(methylthio)acrylonitriles for the first time. The N-heteroannulation process is highly chemoselective and has mild reaction conditions. However, this process fails in the absence of the β-methylthio group in the acrylonitriles. In addition, a new double N-heteroannulation process is demonstrated to synthesise indolo[3,2-c]quinolines from non-heterocyclic precursors. Natural product isocryptolepine is synthesised in four steps from an acyclic precursor.

Pyrrolopyrimidine derivatives and purine analogs as novel activators of Multidrug Resistance-associated Protein 1 (MRP1, ABCC1)

Multidrug resistance (MDR) is the main cause of diminished success in cancer chemotherapy. ABC transport proteins are considered to be one important factor of MDR. Besides P-glycoprotein (P-gp, ABCB1) and Breast Cancer Resistance Protein (BCRP, ABCG2), Mu

Pyrrolopyrimidine Derivatives as Novel Inhibitors of Multidrug Resistance-Associated Protein 1 (MRP1, ABCC1)

Five series of pyrrolo[3,2-d]pyrimidines were synthesized and evaluated with respect to potency and selectivity toward multidrug resistance-associated protein 1 (MRP1, ABCC1). This transport protein is a major target to overcome multidrug resistance in cancer patients. We investigated differently substituted pyrrolopyrimidines using the doxorubicin selected and MRP1 overexpressing small cell lung cancer cell line H69 AR in a calcein AM and daunorubicin cell accumulation assay. New compounds with high potency and selectivity were identified. Piperazine residues at position 4 bearing large phenylalkyl side chains proved to be beneficial for MRP1 inhibition. Its replacement by an amino group led to decreased activity. Aliphatic and aliphatic-aromatic variations at position 5 and 6 revealed compounds with IC50 values in high nanomolar range. All investigated compounds had low affinity toward P-glycoprotein (P-gp, ABCB1). Pyrrolopyrimidines with small substituents showed moderate inhibition against breast cancer resistance protein (BCRP, ABCG2).