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

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

Uses

Used in Pharmaceutical Industry:
3-Aminocrotononitrile is used as an intermediate for the production of various pharmaceuticals, such as sulfsomizole. It plays a crucial role in the synthesis of essential drugs, contributing to the development and manufacturing of life-saving medications.
Used in Dyestuff Industry:
In the dyestuff industry, 3-Aminocrotononitrile is utilized as a key intermediate for the synthesis of different types of dyes. Its unique chemical properties enable the creation of a wide array of colorants used in various applications, including textiles, plastics, and printing inks.
Used in Organic Synthesis:
3-Aminocrotononitrile is an important raw material and intermediate in organic synthesis, where it is employed in the production of heterocycles like pyridines and pyrimidines. These heterocycles are essential components in the development of various chemical compounds and materials.
Used in Agrochemicals:
3-Aminocrotononitrile also finds application in the agrochemical industry, where it is used as a starting material for the synthesis of various agrochemical products. Its versatility in chemical reactions allows for the development of effective solutions for agricultural needs.
Used in Polyurethane Production:
In the polymer industry, 3-Aminocrotononitrile is used in the production of polyurethane, a versatile polymer with a wide range of applications, including foams, elastomers, and coatings. Its use in this industry highlights its importance in creating durable and functional materials.
Used in the Synthesis of Ferrocenyl Pyridines:
3-Aminocrotononitrile reacts with ferrocenyl-1,2-enones to form ferrocenyl pyridines, which are valuable compounds in the field of organometallic chemistry and have potential applications in catalysis and material science.
Used in the Formation of 2-Arylhydrazono-3-ketobutyronitriles:
Through diazotization coupling reactions with p-substituted anilines, 3-Aminocrotononitrile is used to produce 2-arylhydrazono-3-ketobutyronitriles. These compounds have potential applications in the development of new chemical entities and materials.
Used in the Synthesis of Bis(trifluoromethyl)pyrimidinones:
As a bisnucleophilic reagent, 3-Aminocrotononitrile undergoes cyclocondensation with hexafluoroacetone(ethoxycarbonylimine) to form bis(trifluoromethyl)pyrimidinones, which are important intermediates in the synthesis of various pharmaceuticals and agrochemicals.

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

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

Downstream Products

• 769-27-7 6-amino-3-cyano-2,4-dimethylpyridine 
• 1721-23-9 2-methyl-nicotinonitrile 
• 5594-07-0 4-(4-chlorophenyl)-2-methyl-6-phenylpyridine-3-carbonitrile 
• 114303-44-5 8-methyl-10-phenyl-acenaphtho[1,2-b]pyridine-9-carbonitrile 
• 445-71-6 5-cyano-6-methyl-2-trifluoromethyl-nicotinic acid ethyl ester 
• 103040-10-4 3-(5-amino-3-methyl-pyrazol-1-yl)-benzenesulfonamide 
• 861619-37-6 phenoxy-acetic acid-(2-cyano-1-methyl-vinylamide) 
• 153719-44-9 4-(2,4-dinitro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarbonitrile 
• 27036-88-0 N-(2-cyano-1-methyl-vinyl)-benzamide 
• 847062-45-7 4-(3-chloro-phenyl)-2-methyl-6-phenyl-nicotinonitrile 
• 114163-31-4 8-methyl-10-p-tolyl-acenaphtho[1,2-b]pyridine-9-carbonitrile 
• 856858-95-2 4-(2-methoxy-5-nitro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarbonitrile 
• 856859-00-2 4-(4-hydroxy-3-methoxy-2-nitro-phenyl)-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarbonitrile 
• 28317-57-9 phenylazo acetylacetonitrile 

Relevant articles and documents

Reactions of methyl esters of adamantane acids with acetonitrile

Methyl adamantane-1-carboxylate and methyl (1-adamantyl)acetate react with acetonitrile in the presence of sodium hydride to give 3-(1-adamantyl)-3-oxopropanenitrile and 4-(1-adamantyl)-3-oxobutanenitrile, respectively. Reaction involving methyl (1-adamantyl)-acetate produces also 2-(1-adamantyl)-N-(E-1-cyanoprop-1-ene-2-yl)acetamide; the structure of this side product was established by X-ray diffraction analysis.

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.

Study of the Reactivity of the [(PE1CE2P)Ni(II)] (E1, E2 = O, S) Pincer System with Acetonitrile and Base: Formation of Cyanomethyl and Amidocrotononitrile Complexes versus Ligand Decomposition by P-S Bond Activation

Nickel(II) chloride complexes with PE1CE2P (E = O, S) pincer ligands were used as precursors for the generation of cyanomethyl complexes in order to investigate the influence of variations (O vs S) in the side arms of the ligands on reactivity and stability of such compounds. In this regard, five hitherto unknown Ni(II) compounds were synthesized and fully characterized. Reaction of the Ni(II) chloride complex [(iPrPOCSPiPr)NiCl] (2-Cl) with 1 equiv of base and nitrile furnishes the cyanomethyl complex [(iPrPOCSPiPr)NiCH2CN] (2-CM). Increase of the amount of base and nitrile results in the formation of 3-amidocrotononitrile complexes [(iPrPOCOPiPr)NiNHC(CH3)CHCN] (1-ACN) and [(iPrPOCSPiPr)NiNHC(CH3)CHCN] (2-ACN). In contrast, similar reactions of the bis(thiophosphinite) complex 3-Cl resulted in formation of a tetranuclear Ni cluster (4) or a dinuclear 1,3-dithiolate-bridged PSCSP complex 5 by unexpected cleavage of P-S bonds of the pincer ligand.

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.

Direct β-acyloxylation of enamines via PhIO-mediated intermolecular oxidative C-O bond formation and its application to the synthesis of oxazoles

A direct β-acyloxylation of enamine compounds has been achieved by using iodosobenzene (PhIO) as an oxidant to realize the intermolecular oxidative C(sp2)-O bond formation between enamines and various carboxylic acids, including N-protected amino acids. The transformation tolerates a wide range of functional groups and furnishes a variety of β-acyloxy enamines that can be conveniently converted to oxazole compounds via cyclodehydration.

Direct β-acyloxylation of enamines via PhIO-mediated intermolecular oxidative C-O bond formation and its application to the synthesis of oxazoles

A direct β-acyloxylation of enamine compounds has been achieved by using iodosobenzene (PhIO) as an oxidant to realize the intermolecular oxidative C(sp2)-O bond formation between enamines and various carboxylic acids, including N-protected amino acids. The transformation tolerates a wide range of functional groups and furnishes a variety of β-acyloxy enamines that can be conveniently converted to oxazole compounds via cyclodehydration.

Highly efficient RhI-catalyzed asymmetric hydrogenation of β-amino acrylonitriles

(Figure Presented) It takes two to TangPhos: β-Amino acrylonitriles can be readily prepared from acetonitriles. Both of the E/Z isomers undergo hydrogenation with excellent enantioselectivity by using the Rh-TangPhos (TangPhos = l, 1'-ditert-butyl-(2, 2')-diphospholane) catalyst system. The products, chiral β-amino nitriles, are valuable chiral building blocks for many drugs.