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

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

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

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".

An efficient condensation of substituted salicylaldehyde and malononitrile catalyzed by lipase under microwave irradiation

The present work illustrates the condensation of substituted salicylaldehyde and malononitrile catalyzed by lipase under microwave irradiation. The reaction obtains two different products by a delicate control of the substrate molar ratio and reaction time. This protocol has the advantages of high yield, short reaction time and environmental friendliness.

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.

Synthesis of 4H-chromene-isoxazole hybrids via ortho-hydroxy directing cyclization of isoxazole-styrenes and Michael addition of imino-chromenes in aqueous medium

A green, efficient, and one-pot method synthesis of functionalized 4H-chromene-isoxazole hybrids is reported via o-hydroxy group directing cyclization of isoxazole-styrenes and Michael addition of 3,5-dimethyl-4-nitroisoxazole on 2-imino-2H-chromene-3-carbonitrile (independent methods). The developed methodology was further extended for nitromethane, malononitrile, and alkylcyanoacetates as Michael donors.

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.

Aegle marmelos in heterocyclization: Greener, highly efficient, one-pot three-component protocol for the synthesis of highly functionalized 4 H -benzochromenes and 4 H -chromenes

A facile, one-pot three-component protocol for the synthesis of 2-amino-4H-chromene derivatives has been demonstrated using Bael Fruit Extract (BFE) as a natural catalyst in a green reaction medium. This method offers a mild, efficient and highly economic

Synthesis of 2-amino-3-cyano-4H-chromen-4-ylphosphonates and 2-amino-4H-chromenes catalyzed by tetramethylguanidine

Synthesis of 2-amino-4H-chromen-4-ylphosphonates and 2-amino-4H-chromenes has been accomplished by the reaction of salicylaldehyde, malononitrile, dialkyl/diphenylphosphites catalyzed by 1,1,3,3-tetramethylguanidine (TMG) under neat conditions at room tem

Solvent-free cascade assembling of salicylic aldehydes and malononitrile: Rapid and efficient approach to 2-amino-4H-chromene scaffold

Solvent-free NaOAc- or KF-catalyzed assembling of salicylic aldehydes with two molecules of malononitrile affords (2-amino-3-cyano- 4H-chromen-4-yl) malononitriles in 94-99% yields within 10 min.

One-pot synthesis of 4H-chromene and dihydropyrano[3, 2-c]chromene derivatives in hydroalcoholic media

4ff-Chromenes and dihydropyrano[3, 2-c]chromenes are obtained in good to excellent yields by a simple, mild and efficient procedure using poly(N, N'-dibromo-N-ethyl-benzene-1, 3-disulfonamide) [PBBS] and N, N, N, N,-tetrabromobenzene-1, 3-disulfonamide [T