6719-21-7

Basic information

• Product Name: 2-Amino-2-cyanoacetamide
• Synonyms: 2-aminocyanoacetamide;ACETAMIDE, 2-AMINO-2-CYANO-;ACA;2-AMINO-2-CYANOACETAMIDE;TIMTEC-BB SBB001501;2-Amino-2-Cyano acetamide (OR 2-aminocyanoacetamide);Aminocyanoacetamide;2-Amino-2-cyanacetamid
• CAS NO: 6719-21-7
• Molecular Formula: C₃H₅N₃O
• Molecular Weight: 99.09
• EINECS: 229-771-3
• Product Categories: Small molecule;Hydrocyanic acid derivatives;Various hydrocyanic acid derivatives
• Mol File: 6719-21-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 120-124 °C
• Boiling Point: 338.5 °C at 760 mmHg
• Flash Point: 158.5 °C
• Appearance: Beige to tan/Powder
• Density: 1.298 g/cm³
• Vapor Pressure: 9.78E-05mmHg at 25°C
• Storage Temp.: Store at
• PKA: 17.05±0.50(Predicted)
• Water Solubility: soluble
• CAS DataBase Reference: 2-Amino-2-cyanoacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-2-cyanoacetamide(6719-21-7)
• EPA Substance Registry System: 2-Amino-2-cyanoacetamide(6719-21-7)

Safety Data

• Hazard Codes: T,Xi,Xn
• Statements: 34-23-51-36-22
• Safety Statements: 45-36/37/39-26
• WGK Germany: WGK 1 slightly water endangering
• Hazardous Substances Data: 6719-21-7(Hazardous Substances Data)

Usage

Description

2-Amino-2-cyanoacetamide is an organic compound that serves as a versatile building block in chemical synthesis. It is characterized by its beige powder form and possesses unique chemical properties that make it valuable for various applications.

Uses

Used in Chemical Synthesis Industry:
2-Amino-2-cyanoacetamide is used as a building block for chemical synthesis, providing a foundation for the development of new compounds and products. Its attributes make it a valuable component in the creation of various chemical products, contributing to the advancement of the industry.

InChI:InChI=1/C3H5N3O/c4-1-2(5)3(6)7/h2H,5H2,(H2,6,7)/p+1/t2-/m1/s1

Synthetic route

ethyl-2-aminocyano acetate (32683-02-6) → 2-Amino-2-cyanoacetamide (6719-21-7)

Conditions	Yield
With ammonia In methanol at 0 - 5℃; for 1h;	53.6%
With diethyl ether; ammonia; water at 0℃;

(E)-ethyl 2-cyano-2-(hydroxyimino)acetate (89765-49-1) + sodium hydrogencarbonate (144-55-8) → 2-Amino-2-cyanoacetamide (6719-21-7)

Conditions	Yield
In water	13%

nitrosocyanoacetamide → 2-Amino-2-cyanoacetamide (6719-21-7)

Conditions	Yield
With hydrogen; platinum In methanol; water; isopropyl alcohol	1%

2-cyano-2-oximinoacetamide (3849-20-5) → 2-Amino-2-cyanoacetamide (6719-21-7)

Conditions	Yield
With nickel Hydrogenation;
With aluminium amalgam

platinum (7440-06-4) + methyl 2-cyanoacetate (105-34-0) → 2-Amino-2-cyanoacetamide (6719-21-7)

Conditions	Yield
With hydrogenchloride; ammonia; hydrogen; sodium nitrite In methanol; water; acetic acid

methyl 2-cyano-2-(hydroxyimino)acetate (127745-39-5) + platinum (7440-06-4) → 2-Amino-2-cyanoacetamide (6719-21-7)

Conditions	Yield
With ammonia In methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; toluene

carbon disulfide (75-15-0) + 2-Amino-2-cyanoacetamide (6719-21-7) → 5-amino-2-mercaptothiazole-4-carboxamide (52868-63-0)

Conditions	Yield
In methanol Reflux;	95%

Ethoxycarbonyl isothiocyanate (16182-04-0) + 2-Amino-2-cyanoacetamide (6719-21-7) → 5-amino-2-ethoxycarbonylaminothiazole-4-carboxamide

Conditions	Yield
In ethyl acetate Reflux;	92.3%
With acetone

ethyl 2-ethoxy-2-iminoacetate (816-27-3) + 2-Amino-2-cyanoacetamide (6719-21-7) → ethyl 4(5)amino-5(4)carbamoyl-imidazole-2-carboxylate (83566-39-6)

Conditions	Yield
Heating;	92%

1-methyl-3-methylcarbamoyliminomethyl urea (65906-68-5) + 2-Amino-2-cyanoacetamide (6719-21-7) → 5-amino-N1-methyl-1H-imidazole-1,4-dicarboxamide (188612-53-5)

Conditions	Yield
With hydrogenchloride In water; acetonitrile at 20 - 25℃; for 24h; Solvent; Reagent/catalyst;	90.5%
With acetic acid In methanol at 20 - 25℃; for 18h;	88.04%

4-Methoxyphenyl isothiocyanate (2284-20-0) + 2-Amino-2-cyanoacetamide (6719-21-7) → 5-amino-2-(4-methoxyphenylamino)thiazole-4-carboxamide (1228281-45-5)

Conditions	Yield
In ethyl acetate at 80℃; for 0.833333h;	86%

orthoformic acid triethyl ester (122-51-0) + Benzhydrylamine (91-00-9) + 2-Amino-2-cyanoacetamide (6719-21-7) → 1-diphenylmethyl-5-aminoimidazole-4-carboxamide (127574-36-1)

Conditions	Yield
Stage #1: orthoformic acid triethyl ester; 2-Amino-2-cyanoacetamide In acetonitrile for 0.75h; Reflux; Stage #2: Benzhydrylamine In acetonitrile for 0.75h; Reflux;	82%

p-tolylglyoxalmonoxime (17628-76-1) + 2-Amino-2-cyanoacetamide (6719-21-7) → 2-amino-3-carbamoyl-5-(p-methylphenyl)pyrazine 1-oxide (113120-67-5)

Conditions	Yield
In acetic acid for 168h; Ambient temperature;	81%

2-Amino-2-cyanoacetamide (6719-21-7) → 2-cyano-2-diazoacetamide (85059-18-3)

Conditions	Yield
With hydrogenchloride; sodium nitrite In water at 0 - 2℃;	78%
With hydrogenchloride; sodium nitrite In water at 0 - 20℃; for 15h;	7.24 g

orthoformic acid triethyl ester (122-51-0) + benzylamine (100-46-9) + 2-Amino-2-cyanoacetamide (6719-21-7) → 5-amino-1-(phenylmethyl)-1H-imidazole-4-carboxamide (3815-69-8)

Conditions	Yield
Stage #1: orthoformic acid triethyl ester; 2-Amino-2-cyanoacetamide In acetonitrile for 0.75h; Reflux; Stage #2: benzylamine In acetonitrile for 0.75h; Reflux;	78%
Stage #1: orthoformic acid triethyl ester; 2-Amino-2-cyanoacetamide With pyridine In acetonitrile at 100℃; for 1h; Stage #2: benzylamine In acetonitrile for 0.25h;	76%

2-naphthyl isothiocyanate (1636-33-5) + 2-Amino-2-cyanoacetamide (6719-21-7) → 5-amino-2-(naphthalen-2-ylamino)thiazole-4-carboxamide

Conditions	Yield
In ethyl acetate for 0.5h; Reflux;	78%

3-Phenylpropan-1-amine (2038-57-5) + orthoformic acid triethyl ester (122-51-0) + 2-Amino-2-cyanoacetamide (6719-21-7) → 5-amino-1-(3-phenylpropyl)-1H-imidazole-4-carboxamide

Conditions	Yield
Stage #1: orthoformic acid triethyl ester; 2-Amino-2-cyanoacetamide With pyridine In acetonitrile at 100℃; for 1h; Stage #2: 3-Phenylpropan-1-amine In acetonitrile for 0.25h;	76%

ethanolamine (141-43-5) + orthoformic acid triethyl ester (122-51-0) + 2-Amino-2-cyanoacetamide (6719-21-7) → 5-amino-1-(2-hydroxyethyl)-1H-imidazole-4-carboxamide

Conditions	Yield
With pyridine In acetonitrile Reflux;	73.2%
Stage #1: orthoformic acid triethyl ester; 2-Amino-2-cyanoacetamide With pyridine In acetonitrile at 100℃; for 1h; Stage #2: ethanolamine In acetonitrile for 0.25h;	73.2%

C13H21NO + orthoformic acid triethyl ester (122-51-0) + 2-Amino-2-cyanoacetamide (6719-21-7) → 5-amino-1-[1-(1-hydroxyethyl)-4-phenylbutyl]-1H-imidazole-4-carboxamide (212840-00-1)

Conditions	Yield
Stage #1: orthoformic acid triethyl ester; 2-Amino-2-cyanoacetamide In acetonitrile at 100℃; for 1h; Stage #2: C13H21NO In acetonitrile for 0.25h;	73.2%

4-phenyl-1-butylamine (13214-66-9) + orthoformic acid triethyl ester (122-51-0) + 2-Amino-2-cyanoacetamide (6719-21-7) → 5-amino-1-(4-phenylbutyl)-1H-imidazole-4-carboxamide

Conditions	Yield
Stage #1: orthoformic acid triethyl ester; 2-Amino-2-cyanoacetamide With pyridine In acetonitrile at 100℃; for 1h; Stage #2: 4-phenyl-1-butylamine In acetonitrile for 0.25h;	72%

4-((7-cyclopentyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d] pyrimidin-2-yl)amino)-3-fluorobenzoic acid + 2-Amino-2-cyanoacetamide (6719-21-7) → 2-((4-((2-amino-1-cyano-2-oxoethyl)carbamoyl)-2-fluorophenyl) amino)-7-cyclopentyl-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 12h;	72%

methyl 2,5-anhydroallonothioate (95936-45-1) + 2-Amino-2-cyanoacetamide (6719-21-7) → 5-amino-2-(β-D-ribofuranosyl)thiazole-4-carboxamide (95936-47-3)

Conditions	Yield
With pyridine In methanol for 16h; Ambient temperature;	69%

amino-3 phenyl-4 butanol-2 (91251-46-6) + orthoformic acid triethyl ester (122-51-0) + 2-Amino-2-cyanoacetamide (6719-21-7) → 5-amino-1-[1-(1-hydroxyethyl)-2-phenylethyl]-1H-imidazole-4-carboxamide

Conditions	Yield
Stage #1: orthoformic acid triethyl ester; 2-Amino-2-cyanoacetamide With pyridine In acetonitrile at 100℃; for 1h; Stage #2: amino-3 phenyl-4 butanol-2 In acetonitrile for 0.25h;	67%

6-isothiocyanatoquinoline (88240-51-1) + 2-Amino-2-cyanoacetamide (6719-21-7) → 5-amino-2-(quinolin-6-ylamino)thiazole-4-carboxamide

Conditions	Yield
In ethyl acetate for 1.5h; Reflux;	65%

oxo-phenyl-acetaldehyde oxime (532-54-7) + 2-Amino-2-cyanoacetamide (6719-21-7) → 2-amino-3-carbamoyl-5-phenylpyrazine 1-oxide (19994-59-3)

Conditions	Yield
In acetic acid for 168h; Ambient temperature;	64%

ethyl N-(2,3-O-isopropylidene-β-D-ribofuranosyl)acetimidate (88054-47-1) + 2-Amino-2-cyanoacetamide (6719-21-7) → 5-amino-1-(2,3-O-isopropylidene-β-D-ribofuranosyl)-2-methylimidazole-4-carboxamide (88054-50-6)

Conditions	Yield
In acetonitrile for 1.5h; Heating;	64%

propylamine (107-10-8) + 2-Amino-2-cyanoacetamide (6719-21-7) + trimethyl orthoformate (149-73-5) → 5-amino-1-propyl-1H-imidazole-4-carboxamide (61507-88-8)

Conditions	Yield
In acetonitrile	61%

S-benzyl thioacetimidate hydrochloride (32894-07-8) + 2-Amino-2-cyanoacetamide (6719-21-7) → 4-Amino-2-methylimidazole-5-carboxamide hydrochloride (53330-95-3)

Conditions	Yield
In methanol; acetonitrile for 6h; Heating;	60%

1-O-methyl-2,3-O-isopropylidene-5-amino-5-deoxy-β-D-ribofuranose (14131-74-9) + orthoformic acid triethyl ester (122-51-0) + 2-Amino-2-cyanoacetamide (6719-21-7) → methyl 5-(5-amino-4-carbamoylimidazol-1-yl)-5-deoxy-2,3-O-isopropylidene-β-D-ribofuranoside (221551-08-2)

Conditions	Yield
With orthoformic acid triethyl ester In acetonitrile for 0.75h; Cyclization; Heating;	59%

orthoformic acid triethyl ester (122-51-0) + 5-amino-5-deoxy-1,2-O-isopropylidene-α-D-ribofuranose (25572-88-7) + 2-Amino-2-cyanoacetamide (6719-21-7) → 5-(5-amino-4-carbamoylimidazol-1-yl)-5-deoxy-1,2-O-isopropylidene-α-D-ribofuranose (221551-05-9)

Conditions	Yield
With orthoformic acid triethyl ester In acetonitrile for 0.75h; Cycloaddition; Heating;	58%

tert-butyl (4-isothiocyanatophenyl)carbamate (89631-75-4) + 2-Amino-2-cyanoacetamide (6719-21-7) → tert-butyl-4-(5-amino-4-carbamoylthiazol-2-ylamino)phenylcarbamate (1228281-43-3)

Conditions	Yield
In ethyl acetate for 0.5h; Reflux;	57%

p-methoxy-isonitrosoacetophenone (1823-76-3) + 2-Amino-2-cyanoacetamide (6719-21-7) → 2-amino-3-carbamoyl-5-(p-methoxyphenyl)pyrazine 1-oxide (113120-68-6)

Conditions	Yield
In acetic acid for 168h; Ambient temperature;	52%

4-fluorophenyl isothiocyanate (1544-68-9) + 2-Amino-2-cyanoacetamide (6719-21-7) → 5-amino-2-(4-fluorophenylamino)thiazole-4-carboxamide (1228281-40-0)

Conditions	Yield
In ethyl acetate for 0.5h; Reflux;	52%

ethyl 2-ethoxy-2-iminoacetate (816-27-3) + 2-Amino-2-cyanoacetamide (6719-21-7) → ethyl 4(5)amino-5(4)carbamoyl-imidazole-2-carboxylate (83566-39-6) + ethyl 4(5)carboethoxyformamidino-5(4)carbamoyl-imidazole-2-carboxylate (107972-50-9)

Conditions	Yield
In ethanol 1.) reflux, 45 min, 2.) r.t., 24 h;	A 50.5% B 6.7%

chlorhydrate de benzyl (88713-35-3) + 2-Amino-2-cyanoacetamide (6719-21-7) → (benzoyloxy-2 ethoxymethyl)-2 amino-5 carboxamido-4 imidazole (88713-36-4)

Conditions	Yield
In pyridine at 60℃; for 0.666667h;	50%

Upstream product

• 3849-20-5 2-cyano-2-oximinoacetamide 
• 32683-02-6 ethyl-2-aminocyano acetate 
• 89765-49-1 (E)-ethyl 2-cyano-2-(hydroxyimino)acetate 
• 144-55-8 sodium hydrogencarbonate 
• 7440-06-4 platinum 
• 105-34-0 methyl 2-cyanoacetate 
• 127745-39-5 methyl 2-cyano-2-(hydroxyimino)acetate 

Downstream Products

• 854882-46-5 (carbamoyl-cyano-methyl)-carbamic acid ethyl ester 
• 14056-39-4 acetylaminocyanoacetamide 
• 34407-35-7 Ethyl N-(carbamoylcyanomethyl)acetimidate 
• 37800-98-9 2-Methyl-4-amino-imidazol-carboxamid-(5) 
• 37842-62-9 ethyl N-(carbamoylcyanomethyl)formamidate 
• 360-97-4 5-Aminoimidazole-4-carboxamide 
• 5539-46-8 5-aminothiazole-4-carboxamide 
• 60598-58-5 5-amino-2-phenylmethylamino-thiazole-4-carboxylic acid amide 
• 83566-39-6 ethyl 4(5)amino-5(4)carbamoyl-imidazole-2-carboxylate 
• 107972-50-9 ethyl 4⁽⁵⁾carboethoxyformamidino-5⁽⁴⁾carbamoyl-imidazole-2-carboxylate 
• 19994-59-3 2-amino-3-carbamoyl-5-phenylpyrazine 1-oxide 
• 113120-67-5 2-amino-3-carbamoyl-5-(p-methylphenyl)pyrazine 1-oxide 
• 113120-68-6 2-amino-3-carbamoyl-5-(p-methoxyphenyl)pyrazine 1-oxide 
• 88713-36-4 (benzoyloxy-2 ethoxymethyl)-2 amino-5 carboxamido-4 imidazole 

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