61892-68-0

Basic information

• Product Name: 3-cyanopropionamide
• Synonyms: 3-cyanopropionamide;3-Cyanopropanamide
• CAS NO: 61892-68-0
• Molecular Formula: C₄H₆N₂O
• Molecular Weight: 98.10324
• EINECS: 263-303-9
• Mol File: 61892-68-0.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 385.4°C at 760 mmHg
• Flash Point: 186.9°C
• Appearance: /
• Density: 1.105g/cm³
• Vapor Pressure: 3.82E-06mmHg at 25°C
• Refractive Index: 1.454
• CAS DataBase Reference: 3-cyanopropionamide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-cyanopropionamide(61892-68-0)
• EPA Substance Registry System: 3-cyanopropionamide(61892-68-0)

Safety Data

• Hazardous Substances Data: 61892-68-0(Hazardous Substances Data)

Usage

General Description

3-cyanopropionamide is an organic compound with the chemical formula C4H6N2O. It is a white crystalline solid with a molecular weight of 98.10 g/mol. 3-cyanopropionamide is a key intermediate in the synthesis of pharmaceuticals and agrochemicals, and is also used as a chemical building block in the production of various other compounds. It is known to be a versatile chemical reagent in organic synthesis and is widely used in the pharmaceutical and chemical industries. 3-cyanopropionamide is also used in the production of dyes, resins, and polymers. It has low acute toxicity and is generally considered to be a safe compound when handled and used properly.

InChI:InChI=1/C4H6N2O/c5-3-1-2-4(6)7/h1-2H2,(H2,6,7)

Upstream product

• 10137-67-4 ethyl 3-cyanopropionate 
• 56-85-9 L-glutamine 
• 4107-62-4 3-cyano-propionic acid methyl ester 
• 79-06-1 2-propenamide 
• 110-61-2 butanedinitrile 
• 74-90-8 hydrogen cyanide 
• 5875-24-1 3-chloropropionamide 
• 143-33-9 sodium cyanide 
• 127-65-1 chloroamine-T 

Downstream Products

• 616-45-5 2-pyrrolidinon 
• 110-61-2 butanedinitrile 
• 74-90-8 hydrogen cyanide 
• 13031-62-4 4-aminobutyric acid amide hydrochloride 

Relevant articles and documents

Synthesis of α-aminonitriles using aliphatic nitriles, α-amino acids, and hexacyanoferrate as universally applicable non-toxic cyanide sources

In cyanation reactions, the cyanide source is often directly added to the reaction mixture, which restricts the choice of conditions. The spatial separation of cyanide release and consumption offers higher flexibility instead. Such a setting was used for the cyanation of iminium ions with a variety of different easy-to-handle HCN sources such as hexacyanoferrate, acetonitrile or α-amino acids. The latter substrates were first converted to their corresponding nitriles through oxidative decarboxylation. While glycine directly furnishes HCN in the oxidation step, the aliphatic nitriles derived from α-substituted amino acids can be further converted into the corresponding cyanohydrins in an oxidative C-H functionalization. Mn(OAc)2 was found to catalyze the efficient release of HCN from these cyanohydrins or from acetone cyanohydrin under acidic conditions and, in combination with the two previous transformations, permits the use of protein biomass as a non-toxic source of HCN.

Decarboxylation of a Wide Range of Amino Acids with Electrogenerated Hypobromite

Bromide-assisted electrochemical decarboxylation efficiently produces valuable nitriles in high yields from a wide range of naturally occurring amino acids in a single step. Bromide salts are used as both redox mediators and supporting electrolytes in a simple one-compartment setup. As demonstrated for lysine, the selectivity of the decarboxylation can be tuned towards nitriles, amines or amides. An electrochemical system is developed that allows the selective decarboxylation of a wide range of amino acids. Valuable nitriles are obtained in high yields in a single step by using bromide salts as both redox mediators and supporting electrolytes. The product selectivity of lysine can be tuned towards nitriles, amines, or amides.

Synthesis of biobased succinonitrile from glutamic acid and glutamine

Succinonitrile is the precursor of 1,4-diaminobutane, which is used for the industrial production of polyamides. This paper describes the synthesis of biobased succinonitrile from glutamic acid and glutamine, amino acids that are abundantly present in many plant proteins. Synthesis of the intermediate 3-cyanopropanoic amide was achieved from glutamic acid 5-methyl ester in an 86 mol % yield and from glutamine in a 56 mol % yield. 3-Cyanopropanoic acid can be converted into succinonitrile, with a selectivity close to 100 % and a 62 % conversion, by making use of a palladium(II)-catalyzed equilibrium reaction with acetonitrile. Thus, a new route to produce biobased 1,4-diaminobutane has been discovered. Copyright