5098-11-3

Basic information

• Product Name: 5-Amino-1H-imidazol-4-carbonitrile
• Synonyms: 1H-IMidazole-4-carbonitrile,5-aMino-;4-Amino-5-cyanoimidazole;4-Aminoimidazole-5-carbonitrile;5-amino-3H-imidazole-4-carbonitrile;Amino-4-carbonitrile-5-imidazole;Imidazole-4-carbonitrile, 5-amino-;4-Amino-1H-imidazole-5-carbonitrile;4-AMINO-5-IMIDAZOLECARBONITRILE
• CAS NO: 5098-11-3
• Molecular Formula: C₄H₄N₄
• Molecular Weight: 108.1
• EINECS: 225-816-6
• Product Categories: VARIOUSAMINE;Heterocyclic Compounds;Heterocycles
• Mol File: 5098-11-3.mol
• Article Data: 11

Chemical Properties

• Melting Point: 131°C
• Boiling Point: 557.7 °C at 760 mmHg
• Flash Point: 291.1 °C
• Appearance: off-white to pale yellow solid
• Density: 1.42 g/cm³
• Vapor Pressure: 1.79E-12mmHg at 25°C
• Refractive Index: 1.621
• Storage Temp.: Refrigerator
• Solubility: DMSO, Methanol
• PKA: 9.79±0.10(Predicted)
• CAS DataBase Reference: 5-Amino-1H-imidazol-4-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Amino-1H-imidazol-4-carbonitrile(5098-11-3)
• EPA Substance Registry System: 5-Amino-1H-imidazol-4-carbonitrile(5098-11-3)

Safety Data

• Hazard Codes: Xn
• Statements: 23/24/25-41-22-37/38
• Safety Statements: 22-36/37/39-45-39-26
• RIDADR: 3439
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 5098-11-3(Hazardous Substances Data)

Usage

Chemical Properties

Off-White to Pale Yellow Solid

InChI:InChI=1/C4H4N4/c5-1-3-4(6)8-2-7-3/h2H,6H2,(H,7,8)

Synthetic route

4-chloroimidazo<4,5-d>-1,2,3-triazine (52773-49-6) → 5-amino-1H-imidazole-4-carbonitrile (5098-11-3)

Conditions	Yield
With ammonium hydroxide at 120 - 130℃; for 2h; high pressure;	55%
With ammonium hydroxide at 120 - 130℃; for 2h; Product distribution; Mechanism; high pressure;	55%

N-(dicyanomethyl)methanimidate (111267-83-5) → 5-amino-1H-imidazole-4-carbonitrile (5098-11-3)

Conditions	Yield
With ammonia In methanol for 0.0833333h;	51%

4-diazo-4H-imidazole-5-carbonitrile (53000-41-2) + aniline (62-53-3) → 4-imino-3-phenylimidazo<4,5-d>-1,2,3-triazine (126965-18-2) + 5-amino-1H-imidazole-4-carbonitrile (5098-11-3)

Conditions	Yield
In chloroform at 5℃; for 2h;	A 51% B 12%

4-diazo-4H-imidazole-5-carbonitrile (53000-41-2) → 5-amino-1H-imidazole-4-carbonitrile (5098-11-3)

Conditions	Yield
With ammonium hydroxide In ethanol for 1h; Ambient temperature;	45%
With ammonium hydroxide In ethanol for 1h; Product distribution; Mechanism; Ambient temperature;	45%

N-(2-amino-1,2-dicyano-vinyl)-formimydic acid ethyl ester (133123-63-4) → 4,5-diamino-6-cyanopyrimidine (1208986-24-6) + 5-amino-1H-imidazole-4-carbonitrile (5098-11-3)

Conditions	Yield
With guanidine hydrochloride; 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran; ethanol at 10℃; for 1728h; Inert atmosphere;	A 2% B 4%

5-amino-4-(cyanoformimidoyl)-1H-imidazole (81693-59-6) → 5-amino-1H-imidazole-4-carbonitrile (5098-11-3)

Conditions	Yield
In water Ambient temperature; base;

5-aminoimidazole-4-carboxamide hydrochloride (72-40-2) → 5-amino-1H-imidazole-4-carbonitrile (5098-11-3)

Conditions	Yield
With trichlorophosphate for 3.5h; Heating / reflux;
With trichlorophosphate for 3.5h; Heating / reflux;

diaminomaleonitrile (1187-42-4) + trimethyl orthoformate (149-73-5) → 4-amino-1H-imidazole-5-carbonitrile (5098-11-3) + 5-amino-1H-imidazole-4-carbonitrile (5098-11-3)

Conditions	Yield
Stage #1: diaminomaleonitrile; trimethyl orthoformate With methanesulfonic acid In tetrahydrofuran at 40℃; for 1h; Stage #2: With ammonia In tetrahydrofuran; water at 30℃; for 1h;

N-(2-amino-1,2-dicyanovinyl)formamidine (71749-37-6) → 4,5-dicyano-1H-imidazole (1122-28-7) + C5H8N4O (1314916-41-0) + 4-amino-1H-imidazole-5-carbonitrile (5098-11-3) + 5-amino-1H-imidazole-4-carbonitrile (5098-11-3)

Conditions	Yield
With sodium hydroxide In water at 20℃; for 20h;

N-(2-amino-1,2-dicyanovinyl)formamidine (71749-37-6) + 5-amino-4-(cyanoformimidoyl)-1H-imidazole (81693-59-6) → 4-amino-1H-imidazole-5-carbonitrile (5098-11-3) + 5-amino-1H-imidazole-4-carbonitrile (5098-11-3)

Conditions	Yield
Stage #1: N-(2-amino-1,2-dicyanovinyl)formamidine; 5-amino-4-(cyanoformimidoyl)-1H-imidazole With sodium hydroxide In water at 30 - 40℃; for 1h; Stage #2: With hydrogenchloride In water pH=6;

5-amino-1H-imidazole-4-carbonitrile (5098-11-3) → 4-chloroimidazo<4,5-d>-1,2,3-triazine (52773-49-6)

Conditions	Yield
With hydrogenchloride; isopentyl nitrite In ethanol at 0 - 2℃; for 0.166667h;	98%

trimethyl orthovalerate (13820-09-2) + 5-amino-1H-imidazole-4-carbonitrile (5098-11-3) → methyl N-(4-cyano-1-imidazol-5-yl)pentanimidate

Conditions	Yield
In N,N-dimethyl-formamide at 90℃;	96%
With camphor-10-sulfonic acid In N,N-dimethyl-formamide at 90℃; for 1h;	86%

2,2-diethoxy-ethanimidic acid methyl ester (76742-48-8) + 5-amino-1H-imidazole-4-carbonitrile (5098-11-3) → 2-diethoxymethyladenine (79936-09-7)

Conditions	Yield
With acetic acid In methanol for 0.25h;	94%

Trimethyl orthoacetate (1445-45-0) + 5-amino-1H-imidazole-4-carbonitrile (5098-11-3) → methyl N-(4-cyano-1-imidazol-5-yl)acetimidate

Conditions	Yield
In N,N-dimethyl-formamide at 90℃;	93%

tert-butylisonitrile (119072-55-8, 7188-38-7) + 3,4,5-trimethoxy-benzaldehyde (86-81-7) + 5-amino-1H-imidazole-4-carbonitrile (5098-11-3) → 3-(tert-butylamino)-2-(3,4,5-trimethoxyphenyl)-1H-imidazo[1,5-a]imidazole-7-carbonitrile

Conditions	Yield
With perchloric acid In methanol at 20℃; for 24h;	93%

1,1,3,3-tetramethylbutane isonitrile (14542-93-9) + 4-methoxy-benzaldehyde (123-11-5) + 5-amino-1H-imidazole-4-carbonitrile (5098-11-3) → 2-(4-methoxyphenyl)-3-[(2,4,4-trimethylpentan-2-yl)amino]-1H-imidazo[1,5-a]imidazole-7-carbonitrile

Conditions	Yield
With perchloric acid In methanol at 20℃; for 24h;	92%

2-ethoxy-azacyclotridec-1-ene (29956-25-0) + 5-amino-1H-imidazole-4-carbonitrile (5098-11-3) → 6,2-epiminoundecanopurine (116612-45-4)

Conditions	Yield
In butan-1-ol for 96h; Heating;	91%

p-benzyloxybenzaldehyde (4397-53-9) + Benzyl isocyanide (88333-03-3, 10340-91-7) + 5-amino-1H-imidazole-4-carbonitrile (5098-11-3) → 3-(benzylamino)-2-[4-(benzyloxy)phenyl]-1H-imidazo[1,5-a]imidazole-7-carbonitrile

Conditions	Yield
With perchloric acid In methanol at 20℃; for 24h;	91%

orthobenzoic acid trimethyl ester (707-07-3) + 5-amino-1H-imidazole-4-carbonitrile (5098-11-3) → methyl N-(4-cyano-1-imidazol-5-yl)benzimidate

Conditions	Yield
In N,N-dimethyl-formamide at 90℃;	90%

tert-butylisonitrile (119072-55-8, 7188-38-7) + 4-methoxy-benzaldehyde (123-11-5) + 5-amino-1H-imidazole-4-carbonitrile (5098-11-3) → 3-(tert-butylamino)-2-(4-methoxyphenyl)-1H-imidazo[1,5-a]imidazole-7-carbonitrile

Conditions	Yield
With perchloric acid In methanol at 20℃; for 24h; Reagent/catalyst; Concentration; Solvent; Time;	90%

methyl isocyanate (624-83-9) + 5-amino-1H-imidazole-4-carbonitrile (5098-11-3) → 5-methylureido-4-cyanoimidazole (87469-30-5)

Conditions	Yield
In tetrahydrofuran for 0.5h; Ambient temperature;	87%

furan-3-carboxaldehyde (498-60-2) + tert-butylisonitrile (119072-55-8, 7188-38-7) + 5-amino-1H-imidazole-4-carbonitrile (5098-11-3) → 3-(tert-butylamino)-2-(furan-3-yl)-1H-imidazo[1,5-a]imidazole-7-carbonitrile

Conditions	Yield
With perchloric acid In methanol at 20℃; for 24h;	86%

5-ethoxy-3,4-dihydro-2H-pyrrole (931-46-4) + 5-amino-1H-imidazole-4-carbonitrile (5098-11-3) → 9-amino-6,7-dihydro-5H-pyrrolo<1,2-a>purine (116612-40-9)

Conditions	Yield
In butan-1-ol for 48h; Heating;	85%

5-amino-1H-imidazole-4-carbonitrile (5098-11-3) → 5-Aminoimidazole-4-thioamide (20271-18-5)

Conditions	Yield
With hydrogenchloride; thiophosphate sodium salt hydrate In water; water-d2 at 50℃; for 24h; pH=6.5; Sealed tube;	85%

Hexyl isocyanate (2525-62-4) + 5-amino-1H-imidazole-4-carbonitrile (5098-11-3) → C11H17N5O

Conditions	Yield
In tetrahydrofuran; ethyl acetate; acetonitrile for 4h; Reflux;	83.7%

5-amino-1H-imidazole-4-carbonitrile (5098-11-3) → 4-diazo-4H-imidazole-5-carbonitrile (53000-41-2)

Conditions	Yield
With hydrogenchloride; sodium nitrite In water at 0℃; for 2h;	83%
With acetic acid; sodium nitrite	78%

Benzyl isocyanide (88333-03-3, 10340-91-7) + 3,4,5-trimethoxy-benzaldehyde (86-81-7) + 5-amino-1H-imidazole-4-carbonitrile (5098-11-3) → 3-(benzylamino)-2-(3,4,5-trimethoxyphenyl)-1H-imidazo[1,5-a]imidazole-7-carbonitrile

Conditions	Yield
With perchloric acid In methanol at 20℃; for 24h;	83%

5-amino-1H-imidazole-4-carbonitrile (5098-11-3) + 2-cyano-3-chlorocinnamonitrile (18270-61-6) → C14H8N6

Conditions	Yield
With TEA In ethanol for 24h; Heating;	82%

oct-2-ynal (1846-68-0) + tert-butylisonitrile (119072-55-8, 7188-38-7) + 5-amino-1H-imidazole-4-carbonitrile (5098-11-3) → 3-(tert-butylamino)-2-(hept-1-yn-1-yl)-1H-imidazo[1,5-a]imidazole-7-carbonitrile

Conditions	Yield
With perchloric acid In methanol at 20℃; for 24h;	82%

1-isocyanatooctane (3158-26-7) + 5-amino-1H-imidazole-4-carbonitrile (5098-11-3) → C13H21N5O

Conditions	Yield
In tetrahydrofuran; ethyl acetate; acetonitrile for 4h; Reflux;	82%

3-(4-(trifluoromethyl)phenyl)propiolaldehyde (183801-13-0) + tert-butylisonitrile (119072-55-8, 7188-38-7) + 5-amino-1H-imidazole-4-carbonitrile (5098-11-3) → C19H16F3N5

Conditions	Yield
With perchloric acid In methanol at 20℃; for 24h;	81%

furan-3-carboxaldehyde (498-60-2) + 1,1,3,3-tetramethylbutane isonitrile (14542-93-9) + 5-amino-1H-imidazole-4-carbonitrile (5098-11-3) → 2-(furan-3-yl)-3-[(2,4,4-trimethylpentan-2-yl)amino]-1H-imidazo[1,5-a]imidazole-7-carbonitrile

Conditions	Yield
With perchloric acid In methanol at 20℃; for 24h;	81%

2-ethoxy-azacycloundec-1-ene (72687-05-9) + 5-amino-1H-imidazole-4-carbonitrile (5098-11-3) → 6,2-epiminononanopurine (116612-43-2)

Conditions	Yield
In butan-1-ol for 96h; Heating;	80%

tert-butylisonitrile (119072-55-8, 7188-38-7) + 4-methyl-benzaldehyde (104-87-0) + 5-amino-1H-imidazole-4-carbonitrile (5098-11-3) → 3-(tert-butylamino)-2-(p-tolyl)-1H-imidazo[1,5-a]imidazole-7-carbonitrile

Conditions	Yield
With perchloric acid In methanol at 20℃; for 24h;	80%

1,1,1-trimethoxybutane (43083-12-1) + 5-amino-1H-imidazole-4-carbonitrile (5098-11-3) → methyl N-(4-cyano-1-imidazol-5-yl)butyrimidate

Conditions	Yield
In N,N-dimethyl-formamide at 90℃;	79%

tert-butylisonitrile (119072-55-8, 7188-38-7) + 3-methoxy-benzaldehyde (591-31-1) + 5-amino-1H-imidazole-4-carbonitrile (5098-11-3) → 3-(tert-butylamino)-2-(3-methoxyphenyl)-1H-imidazo[1,5-a]imidazole-7-carbonitrile

Conditions	Yield
With perchloric acid In methanol at 20℃; for 24h;	79%

1,1,3,3-tetramethylbutane isonitrile (14542-93-9) + 4-nitrobenzaldehdye (555-16-8) + 5-amino-1H-imidazole-4-carbonitrile (5098-11-3) → 2-(4-nitrophenyl)-3-[(2,4,4-trimethylpentan-2-yl)amino]-1H-imidazo[1,5-a]imidazole-7-carbonitrile

Conditions	Yield
With perchloric acid In methanol at 20℃; for 24h;	79%

4-methoxyphenyl magnesium bromide (13139-86-1) + 5-amino-1H-imidazole-4-carbonitrile (5098-11-3) → (5-amino-1H-imidazol-4-yl)-(4-methoxy-phenyl)-methanone

Conditions	Yield
Stage #1: 4-methoxyphenyl magnesium bromide; 5-amino-1H-imidazole-4-carbonitrile In tetrahydrofuran at 20℃; for 2h; Cooling with ice-salt bath; Stage #2: With hydrogenchloride; water In tetrahydrofuran at 90 - 95℃; for 1h; Stage #3: With ammonia In tetrahydrofuran; water pH=10;	77%

tert-butylisonitrile (119072-55-8, 7188-38-7) + ortho-anisaldehyde (135-02-4) + 5-amino-1H-imidazole-4-carbonitrile (5098-11-3) → 3-(tert-butylamino)-2-(2-methoxyphenyl)-1H-imidazo[1,5-a]imidazole-7-carbonitrile

Conditions	Yield
With perchloric acid In methanol at 20℃; for 24h;	77%

tert-butylisonitrile (119072-55-8, 7188-38-7) + 2-bromo-4-methylbenzaldehyde (824-54-4) + 5-amino-1H-imidazole-4-carbonitrile (5098-11-3) → 2-(2-bromo-4-methylphenyl)-3-(tert-butylamino)-1H-imidazo[1,5-a]imidazole-7-carbonitrile

Conditions	Yield
With perchloric acid In methanol at 20℃; for 24h;	77%

Upstream product

• 5181-05-5 2-aminomalononitrile 
• 463-52-5 formamidine 
• 1187-42-4 diaminomaleonitrile 
• 149-73-5 trimethyl orthoformate 
• 71749-37-6 N-(2-amino-1,2-dicyanovinyl)formamidine 
• 81693-59-6 5-amino-4-(cyanoformimidoyl)-1H-imidazole 
• 52773-49-6 4-chloroimidazo<4,5-d>-1,2,3-triazine 
• 53000-41-2 4-diazo-4H-imidazole-5-carbonitrile 
• 111267-83-5 N-(dicyanomethyl)methanimidate 
• 62-53-3 aniline 
• 72-40-2 5-aminoimidazole-4-carboxamide hydrochloride 
• 133123-63-4 N-(2-amino-1,2-dicyano-vinyl)-formimydic acid ethyl ester 

Downstream Products

• 57042-89-4 (1R)-1-(6-amino-7⁽⁹⁾H-purin-2-yl)-O³,O⁵-bis-(4-methyl-benzoyl)-D-erythro-1,4-anhydro-2-deoxy-pentitol 
• 57042-90-7 (1S)-1-(6-amino-7⁽⁹⁾H-purin-2-yl)-O³,O⁵-bis-(4-methyl-benzoyl)-D-erythro-1,4-anhydro-2-deoxy-pentitol 
• 108575-59-3 1-benzyl-4-benzylamino-5-cyanoimidazole 
• 4059-12-5 4-amino-1-benzylimidazole-5-carbonitrile 
• 60598-48-3 5-amino-1-benzyl-1H-imidazole-4-carbonitrile 
• 108575-38-8 1-phenyl-6-imino-2-thioxopurine 
• 87460-47-7 1-Allyl-5-amino-1H-imidazole-4-carbonitrile 
• 87460-48-8 3-Allyl-5-amino-3H-imidazole-4-carbonitrile 
• 69-89-6 2,6-dihydroxypurine 
• 69-89-6 xanthine 
• 17289-59-7 4-amino-5-cyano-1-(β-D-ribofuranosyl)imidazole 
• 23192-64-5 5-amino-1-β-D-ribofuranosyl-1H-imidazole-4-carbonitrile 
• 70590-21-5 5-amino-1-(tri-O-benzoyl-β-D-ribofuranosyl)-1H-imidazole-4-carbonitrile 
• 228875-07-8 9-benzyl-2-pentyladenine 

Relevant articles and documents

SYNTHESIS AND PROPERTIES OF ANALOGS OF 5(OR 4)-AMINOIMIDAZOLE-4(OR 5)-CARBOXAMIDE (AICA) AND PURINES. 12. INVESTIGATION OF THE INTERACTION OF 4-CHLOROIMIDAZO-1,2,3-TRIAZINE WITH NUCLEOPHILES

The reactions of 4-chloroimidazo-1,2,3-triazine with a number of nucleophilic reagents have been studied.Either replacement of the chlorine atom in position 4 of the 1,2,3-triazine ring or opening of the triazine ring with the formation of products of the interaction of the intermediate 5-diazoimidazole-4-carbonitrile with these nucleophiles occurs, depending on the nucleophilicity of the reagent.

METHOD FOR PRODUCTION OF N-(2-AMINO-1,2-DICYANOVINYL)IMIDATE, METHOD FOR PRODUCTION OF N-(2-AMINO-1,2-DICYANOVINYL)FORMAMIDINE, AND METHOD FOR PRODUCTION OF AMINOIMIDAZOLE DERIVATIVE

A method for producing N-(2-amino-1,2-dicyanovinyl)imidates represented by the following formula (1-III) under low temperature conditions within a short period of time in high yield is provided. In addition, a method for producing N-(2-amino-1,2-dicyanovinyl)formamidine represented by the following formula (2-II) which is suitably applicable to a cyclization reaction for producing AICN, AICA or the like and which enhances yield of the cyclization reaction is provided. In addition, a method for producing aminoimidazole derivatives represented by the following formula (3-V) in high yield by using diaminomaleonitrile as a starting material is provided.

DNA Methyltransferase inhibitors

A compound of the formula or a pharmaceutically acceptable salt thereof,whereinR1, R2, and R3 are the same or different and are independently hydrogen, lower alkyl, aryl or substituted aryl, lower alkoxy, lower alkoxyalkyl, or cycloalkyl or cycloalkyl alkoxy, where each cycloalkyl group has from 3-7 members, where up to two of the cycloalkyl members are optionally hetero atoms selected from oxygen and nitrogen, and where any member of the alkyl, aryl or cycloalkyl group is optionally substituted with halogen, lower alkyl or lower alkoxy, aryl or substituted aryl, andwhereR3 can be ribose, deoxyribose or phosphorylated derivatives thereof,whereinR1, R2, and R3 are not all hydrogen andwhereinwhen R3 is ribose, deoxyribose or phosphorylated derivatives thereof, one of R1 or R2 is not hydrogen.