2-Cyanoacetamide

Chemical properties

White or light yellow needle crystal or powder. Slightly soluble in water, easily soluble in ethanol.

The Uses of 2-Cyanoacetamide

2-Cyanoacetamide was used in spectrofluorimetric method for the determination of some antihistaminic H1 receptor antagonist drugs such as ebastine, cetirizine dihydrochloride and fexofenadine hydrochloride. It may be used in fluorometric determination of 3,4-dihydroxyphenylalanine. It was used as post column fluorigenic derivatizing agent for the bio-analysis and pharmacokinetics of chitosan ester in rabbit serum. Cyanoacetamide is the starting reagent for vitamin B6 synthesis. It reacts with reducing carbohydrates in borate buffer to give intense fluorescence and is useful for the automated analysis of carbohydrates as borate complexes. It can also be used in the synthesis of heterocyclic compounds such as pyrazole, pyridine and pyrimidine derivatives. Moreover, it can also be applied for the spectrophotometric assay of the enzyme activity of cellulose in related host cells.

Definition

2-Cyanoacetamide is an acetic amide with a nitrile functional group. It is a codon of glutamine that directs the placement of glutamine into a polypeptide.

Preparation

Cyanoacetamide can be prepared from ethyl cyanoacetate and ammonia. Cool the ethyl cyanoacetate to below 200°C, add concentrated ammonia water to react, and the mixture turns from turbid to clear. After cooling in cold water for 20 minutes, a precipitate is precipitated. After filtration and drying, the crude product is obtained, and then the crude product of cyanoacetamide is added. In the boiling ethanol, after dissolving it, add a small amount of activated carbon for decolorization and purification, filter, cool the filtrate to separate out the precipitate, and dry it at 80-100 ℃ to obtain the fine cyanoacetamide.

General Description

Cyanoacetamide is the starting reagent for vitamin B₆ synthesis. It reacts with reducing carbohydrates in borate buffer to give intense fluorescence andis useful for the automated analysis of carbohydrates as borate complexes.

Reaction

2-Cyanoacetamide is a versatile chemical reagent that is easily alkylated at C2.
(1) It undergoes alkylation with 2-chloroacetoacetate in the presence of triethylamine, followed by nucleophilic attack of the amide nitrogen on the carbonyl group and acid-catalyzed dehydration to produce substituted pyrroles in high yields. (2) It reacts with various benzaldehydes in the presence of nitrogen-containing bases to produce (E)-2-cyano-3-phenylacrylamide.
(3) Ketones or aldehydes react with 2-cyanoacetamide in the presence of base and elemental sulfur to produce substituted 2-aminothiophenes via a Gewald reaction.

Toxicity

2-Cyanoacetamide is a cyanide that is harmful if swallowed; it can cause skin irritation, severe eye irritation, and respiratory irritation. Cyanide poisoning is characterized by rapid, deep and short breathing, general weakness, dizziness, headache, vertigo, confusion, convulsions/seizures, and eventually loss of consciousness. Short-term exposure to high concentrations of cyanide can damage the brain and heart and can even cause coma, seizures, respiratory arrest, cardiac arrest, and death. Long-term inhalation of cyanide can cause difficulty breathing, chest pain, vomiting, blood changes, headaches, and thyroid enlargement. Skin contact with cyanide salts can irritate and produce ulcers.

Purification Methods

Crystallise the amide from MeOH/dioxane (6:4), then water and dry it over P2O5 under vacuum. [Beilstein 2 IV 1891.]