175136-95-5

Basic information

• Product Name: 2-(2-AMINO-6-CHLORO-3-CYANO-4H-CHROMEN-4-YL)MALONONITRILE
• Synonyms: 2-(2-AMINO-6-CHLORO-3-CYANO-4H-CHROMEN-4-YL)MALONONITRILE;TIMTEC-BB SBB001064;2-(2-AMINO-6-CHLORO-3-CYANO-4H-(1)BENZOPYRAN-4-YL)MALONONITRILE
• CAS NO: 175136-95-5
• Molecular Formula: C13H7ClN4O
• Molecular Weight: 270.67
• Mol File: 175136-95-5.mol
• Article Data: 9

Chemical Properties

• Melting Point: 155 °C
• Boiling Point: 560°Cat760mmHg
• Flash Point: 292.5°C
• Appearance: /
• Density: 1.48g/cm³
• Vapor Pressure: 1.43E-12mmHg at 25°C
• Refractive Index: 1.65
• CAS DataBase Reference: 2-(2-AMINO-6-CHLORO-3-CYANO-4H-CHROMEN-4-YL)MALONONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-AMINO-6-CHLORO-3-CYANO-4H-CHROMEN-4-YL)MALONONITRILE(175136-95-5)
• EPA Substance Registry System: 2-(2-AMINO-6-CHLORO-3-CYANO-4H-CHROMEN-4-YL)MALONONITRILE(175136-95-5)

Safety Data

• Hazard Codes: Xn:Harmful
• Statements: R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.; R36/37/38:Irritating to eyes, respiratory system
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S36/37/39:Wear suitabl
• Hazardous Substances Data: 175136-95-5(Hazardous Substances Data)

Usage

Molecular weight

247.65 g/mol
The molecular weight of the compound is 247.65 grams per mole, which indicates the mass of one mole of the compound.

Chemical structure

Chromen-4-yl malononitrile derivative
The compound is derived from a chromene ring (a benzene ring fused with a pyran ring) and has malononitrile functional groups attached to it.

Amino group

-NH2
The compound contains an amino group, which is a basic functional group with the ability to form hydrogen bonds and coordinate with metal ions.

Chlorine atom

-Cl
A chlorine atom is attached to the chromene ring, which can influence the compound's reactivity, polarity, and lipophilicity.

Cyano group

-CN
The cyano group is a highly polar and electronegative functional group, which can contribute to the compound's biological activity and interactions with target proteins.

Potential applications

Pharmaceutical research and development
The compound is used as a potential drug candidate in pharmaceutical research due to its potential biological activities, such as anticancer, antiviral, and anti-inflammatory properties.

Synthesis of novel therapeutic agents

Unique structure and functional groups
The compound's unique structure and functional groups make it a promising target for the synthesis of new therapeutic agents for various medical conditions.

InChI:InChI=1/C13H7ClN4O/c14-8-1-2-11-9(3-8)12(7(4-15)5-16)10(6-17)13(18)19-11/h1-3,7,12H,18H2

Upstream product

• 635-93-8 5-chlorosalicyclaldehyde 
• 109-77-3 malononitrile 
• 476479-85-3 6-Chloro-2-imino-2H-chromene-3-carbonitrile 

Relevant articles and documents

Diethylamine: A smart organocatalyst in eco-safe and diastereoselective synthesis of medicinally privileged 2-amino-4H-chromenes at ambient temperature

Diethylamine has been demonstrated to be an efficient organocatalyst in the diastereoselective synthesis of Bcl-2 protein antagonist (HA-14-1) and of its structural analogues by one-pot condensation between salicylaldehyde and three different C-H acids, viz. ethyl cyanoacetate, phenylsulfonyl acetonitrile, and malononitrile. Easy commercial availability of the catalyst at extremely low cost and avoidance of conventional work-up as well as purification procedures qualifies this scalable protocol for a "near-ideal synthesis".

Visible light induced, catalyst free, convenient synthesis of chromene nucleus and its derivatives using water-ethanol mixture as a solvent

A highly efficient, green, eco-friendly, one pot protocol has been demonstrated for the synthesis of 2-imino-2H-chromene-3-carbonitrile (3), 2-aminochromene (4) and chromeno(2,3-b)pyridines (5). The synthesis of the chromene nucleus has been carried out under visible light irradiation in a water-ethanol mixture at room temperature using salicylaldehyde and malononitrile in different proportions. The adopted method shows significant advantages such as mild and clean reaction conditions, eco-friendly procedures, absence of catalysts and a short reaction time. This protocol involves the use of CFL as the visible light source and shows high selectivity in the presence of a mixture of ethanol and water. The reaction proceeds with good to excellent yield.

Catalyst-free cascade synthesis of densely functionalized chromenes in water

An expeditious and environmental friendly, general protocol has been developed for the synthesis of 2-amino-3-cyano-4H-chromenes via cascade Knoevenagel-Michael-intramolecular cyclization in water. Pure solid products were obtained by simple filtration technique. The aqueous catalyst-free reactions lead to high product yield at room temperature.