1118-61-2

Basic information

• Product Name: 3-Aminocrotononitrile
• Synonyms: (2E)-3-Amino-2-butenenitrile;3-amino-2-butenenitril;3-aminocrotononitrile,mixtureofcisandtrans;beta-Aminocrotonitrile;BETA-AMINOCROTONONITRILE;DIACETONITRILE;3-AMINO-2-BUTENONITRILE;3-AMINO-2-BUTENENITRILE
• CAS NO: 1118-61-2
• Molecular Formula: C₄H₆N₂
• Molecular Weight: 82.1
• EINECS: 214-266-2
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 1118-61-2.mol
• Article Data: 9

Chemical Properties

• Melting Point: 79-81°C
• Boiling Point: 120°C 4mm
• Flash Point: 154°C
• Appearance: Yellow/Flakes
• Density: 0.952
• Vapor Pressure: 0.00484mmHg at 25°C
• Refractive Index: 1.4449 (estimate)
• Storage Temp.: 2-8°C
• Solubility: 95% ethanol: soluble25mg/mL, clear, colorless to yellow
• PKA: 3.88±0.70(Predicted)
• Water Solubility: Very soluble in water, soluble in ethanol.
• BRN: 1719815
• CAS DataBase Reference: 3-Aminocrotononitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Aminocrotononitrile(1118-61-2)
• EPA Substance Registry System: 3-Aminocrotononitrile(1118-61-2)

Safety Data

• Hazard Codes: Xn,T
• Statements: 22-20/21/22-43-24/25
• Safety Statements: 22-24/25-29-36/37-45
• RIDADR: UN 3439 6.1/PG 3
• WGK Germany: 3
• TSCA: Yes
• PackingGroup: III
• Hazardous Substances Data: 1118-61-2(Hazardous Substances Data)

Usage

Chemical Properties

Yellowish flakes

Uses

Different sources of media describe the Uses of 1118-61-2 differently. You can refer to the following data:
1. 3-Aminocrotononitrile is used as intermediate for the syntheses of heterocycles (e.g. pyridines and pyrimidines) and for the production of polyurethane). It is used in the pharmaceutical (e.g. production of sulfsomizole) and dyestuff industries. Product Data Sheet
2. 3-Aminocrotononitrile reacts with ferrocenyl-1,2-enones to form ferrocenyl pyridines. It undergoes diazotization coupling reaction with p-substituted anilines to give 2-arylhydrazone-3-ketimino-butyronitriles.3-Aminocrotononitrile, (E)+(Z), is used in reaction with aryldiazonium salts gave, instead of the expected triazene, 2-arylhydrazono-3-ketobutyronitrile by electrophilic attack at the ?-carbon and hydrolysis of the resulting imine. It is also used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff. 3-Aminocrotononitrile was used as bisnucleophilic reagent which on cyclocondensation with hexafluoroacetone(ethoxycarbonylimine) forms bis(trifluoromethyl)pyrimidinones.

Biochem/physiol Actions

3-Aminocrotononitrile reacts with ferrocenyl-1,2-enones to form ferrocenyl pyridines. It undergoes diazotization coupling reaction with p-substituted anilines to give 2-arylhydrazone-3-ketimino-butyronitriles.

InChI:InChI=1/C4H6N2/c1-4(6)2-3-5/h2H,6H2,1H3/b4-2-

Upstream product

• 75-05-8 acetonitrile 
• 60-29-7 diethyl ether 
• 107-12-0 propiononitrile 
• 5765-44-6 5-methylisoxazole 
• 7664-41-7 ammonia 
• 14798-97-1 1-cyano-2-(trimethylsilyl)amino-1-propene 
• 925-90-6 ethylmagnesium bromide 
• 816-43-3 lithium diethylamide 

Downstream Products

• 1721-23-9 2-methyl-nicotinonitrile 
• 5594-07-0 4-(4-chlorophenyl)-2-methyl-6-phenylpyridine-3-carbonitrile 
• 445-71-6 5-cyano-6-methyl-2-trifluoromethyl-nicotinic acid ethyl ester 
• 2469-99-0 Cyanoaceton 
• 90814-75-8 3-p-toluidino-crotononitrile 
• 846546-76-7 4-(4-acetoxy-3-methoxy-2-nitro-phenyl)-5-cyano-2,6-dimethyl-1,4-dihydro-pyridine-3-carboxylic acid ethyl ester 
• 846546-78-9 5-cyano-4-(4-hydroxy-3-methoxy-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3-carboxylic acid ethyl ester 
• 846547-59-9 5-cyano-4-(3,4-dimethoxy-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3-carboxylic acid ethyl ester 
• 63093-77-6 Ethyl 5-cyano-1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)-3-pyridinecarboxylate 
• 109482-47-5 2-benzoyl-3-benzoylamino-crotononitrile 
• 25354-52-3 4-(2-cyano-1-methyl-vinylamino)-benzoic acid 
• 42412-18-0 3-phenylhydrazono-butyronitrile 
• 1563-42-4 2-((Z)-1-amino-ethyliden)-5-oxo-hex-3t-enenitrile 
• 39603-75-3 3-(benzylamino)but-2-enenitrile 

Relevant articles and documents

SYNTHESIS AND ANTICONVULSANT ACTIVITY OF 5-AMINOPYRAZOLES

-

Microwave-assisted synthesis of chiral nopinane-annelated pyridines by condensation of pinocarvone oxime with enamines promoted by FeCl3 and CuCl2

Reaction of pinocarvone oxime with enamines and FeCl3 or CuCl2 resulted in annulation of nopinane carbon frame with pyridine and regioselective formation of chiral nopinane-annelated pyridines in 20-39% yields. Chemical structure of the pyridine derivatives were proved by precise NMR study.

Double-twist pyridine-carbonitrile derivatives yielding excellent thermally activated delayed fluorescence emitters for high-performance OLEDs

Possessing high photoluminescence quantum yield (PLQY) and fast reverse intersystem crossing (RISC) process are critical for obtaining efficient thermally activated delayed fluorescence (TADF) emitters. Herein, two donor-spacer-acceptor molecules, namely, 4-(4-(9,9-dimethylacridin-10(9H)-yl)phenyl)-2,6-dimethylpyridine-3,5-dicarbonitrile (Me-DMAC) and 4-(4-(10H-phenoxazin-10-yl)phenyl)-2,6-dimethylpyridine-3,5-dicarbonitrile (Me-PXZ), were developed via a double-twist design strategy. The large hindrance induces a twisted geometry, leading to small ΔEST values and fast RISC processes. The time-resolved photophysical measurements revealed the TADF emissions of these pyridine-3,5-dicarbonitrile-based molecules in doped thin films. High external quantum efficiency (EQE) values of 25.8% and 21.1% were achieved in organic light-emitting diodes (OLEDs) using green Me-DMAC and yellow Me-PXZ dyes, respectively, as emitters.

Acid-promoted rapid solvent-free access to substituted 1,4-dihydropyridines from β-ketothioamides

β-Ketothioamides (KTAs) have been used as building blocks with aldehydes and β-enaminonitriles for synthesis of 1,4-dihydropyridines in the presence of AcOH under solvent-free conditions within 5 min. This new strategy exhibits remarkable features such as high chemoselectivity, mild reaction conditions, easily available substrates, and good yields.