72-40-2

Basic information

• Product Name: 4-Amino-5-imidazolecarboxamide hydrochloride
• Synonyms: 5-amino-4-imidazolecarboxamide hydrochloride (intermediate of dacarbazine);5-Amino-1H-imidazole-4-carboxamide hydrochloride 98%;5-amino-1H-imidazole-4-carboxamide HCl;4-Amino-5-(aminocarbonyl)imidazole Hydrochloride;4-AMINO-5-IMIDAZOLECARBOXAMIDE HCL, (AICA) 98+%;4-AMINO-5-IMIDAZOLECARBOXAMIDE HYDROCHLORIDE 99%;4-Amino-5-imidazolecarboxamide hydrochloride ,99%;4-Amino-5-imidazolecarboxamide hydrochloride,98%
• CAS NO: 72-40-2
• Molecular Formula: C₄H₆N₄O*ClH
• Molecular Weight: 162.58
• EINECS: 200-778-3
• Product Categories: Imidazoles, Pyrroles, Pyrazoles, Pyrrolidines;pharmacetical;Imidazoles;(intermediate of dacarbazine)
• Mol File: 72-40-2.mol
• Article Data: 2

Chemical Properties

• Melting Point: 250-252 °C (dec.)(lit.)
• Boiling Point: 522.1 °C at 760 mmHg
• Flash Point: 269.6 °C
• Appearance: White/Crystals or Crystalline Powder
• Vapor Pressure: 5.33E-11mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: water: soluble50mg/mL, clear, light yellow
• Water Solubility: SOLUBLE
• Sensitive: Hygroscopic
• Stability: Hygroscopic
• BRN: 3701645
• CAS DataBase Reference: 4-Amino-5-imidazolecarboxamide hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Amino-5-imidazolecarboxamide hydrochloride(72-40-2)
• EPA Substance Registry System: 4-Amino-5-imidazolecarboxamide hydrochloride(72-40-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-24/25-36-26
• WGK Germany: 3
• RTECS: NI3911000
• TSCA: Yes
• Hazardous Substances Data: 72-40-2(Hazardous Substances Data)

Usage

Chemical Properties

very slightly beige fine powder

Uses

5-Amino-4-imidazolecarboxamide hydrochloride was used in the synthesis of heterocyclic compounds such as guanine, purines and pyrimidines.

General Description

Corrosion inhibition and adsorption characteristics of 5-amino-4-imidazolecarboxamide hydrochloride on aluminum in 1M HCl has been investigated.

Purification Methods

Recrystallise the hydrochloride from EtOH. [Kuroda & Hakko JEst(1) Est(2)Heterocycl Chem 30 593 1993, Alhede et al. J Org Chem 56 2139 1991, Cheru et al. Heterocycles 24 1133 1992, Beilstein 25 II 221, 25 III/IV 4329.]

InChI:InChI=1/C4H6N4O.ClH/c5-3-2(4(6)9)7-1-8-3;/h1H,5H2,(H2,6,9)(H,7,8);1H

Synthetic route

5-Aminoimidazole-4-carboxamide (360-97-4) → 5-amino-1H-imidazole-4-carboxamide monohydrochloride (72-40-2)

Conditions	Yield
With hydrogenchloride In methanol; water at 68℃; for 0.5h; Inert atmosphere;	84%

5-Aminoimidazole-4-carboxamide (360-97-4) → 5-amino-1H-imidazole-4-carboxamide monohydrochloride (72-40-2) + 5-diazoimidazole-4-carboxamide (7008-85-7)

Conditions	Yield
With hydrogenchloride; sodium nitrite In water

3-ethoxy-4-(2-ethoxyethoxy)pyridine-2-carbaldehyde (955042-99-6) + 5-amino-1H-imidazole-4-carboxamide monohydrochloride (72-40-2) → 4-({[3-ethoxy-4-(2-ethoxyethoxy)pyridin-2-yl]methyl}amino)-1H-imidazole-5-carboxamide (955043-00-2)

Conditions	Yield
With sodium cyanoborohydride In methanol at 20℃; for 48h;	100%

ethyl N-benzyloxycarbonylamino-orthoacetate (13347-35-8) + 5-amino-1H-imidazole-4-carboxamide monohydrochloride (72-40-2) → 5-<(N-benzyloxycarbonylaminomethyl)(ethoxy)methylimino>imidazole-4-carboxamide

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 1h;	95%

5-amino-1H-imidazole-4-carboxamide monohydrochloride (72-40-2) + benzyl isothiocyanate (3173-56-6) → 5-Amino-1-(N-benzylcarbamoyl)imidazole-4-carboxamide (188612-59-1)

Conditions	Yield
With triethylamine In dimethyl sulfoxide at 25℃;	95%
With triethylamine In dimethyl sulfoxide at 20℃;	88%

5-amino-1H-imidazole-4-carboxamide monohydrochloride (72-40-2) + 2-chloro-5-nitrobenzaldehyde (6361-21-3) → 5-[N-(2-chloro-5-nitrobenzylidene)amino]imidazole-4-carboxamide

Conditions	Yield
With sodium acetate In ethanol; water for 1h; Heating;	94%

5-amino-1H-imidazole-4-carboxamide monohydrochloride (72-40-2) + 2-chloro-benzaldehyde (89-98-5) → 5-[N-(2-chlorobenzylidene)amino]imidazole-4-carboxamide

Conditions	Yield
With sodium acetate In ethanol; water for 1h; Heating;	93%

5-amino-1H-imidazole-4-carboxamide monohydrochloride (72-40-2) + m-xylylene diisocyanate (3634-83-1) → 1,3-bis(5-amino-4-carbamoylimidazolecarboxamidomethyl)benzene

Conditions	Yield
With triethylamine In acetonitrile for 60h; Ambient temperature;	92%

5-amino-1H-imidazole-4-carboxamide monohydrochloride (72-40-2) + 2-nitro-benzaldehyde (552-89-6) → 5-[N-(2-nitrobenzylidene)amino]imidazole-4-carboxamide

Conditions	Yield
With sodium acetate In ethanol; water for 1h; Heating;	91%

5-amino-1H-imidazole-4-carboxamide monohydrochloride (72-40-2) + methyl isocyanate (624-83-9) → 5-amino-N1-methyl-1H-imidazole-1,4-dicarboxamide (188612-53-5)

Conditions	Yield
With triethylamine In dimethyl sulfoxide at 20℃;	90%
With triethylamine In dimethyl sulfoxide at 25℃;	85%
With triethylamine 1.) CH3CN, 25 deg C, 10 min, 2.) 25 deg C, 18 h; Yield given. Multistep reaction;

2-ethoxy-2-methylpropanal (130797-57-8) + 5-amino-1H-imidazole-4-carboxamide monohydrochloride (72-40-2) → 4-[(2-ethoxy-2-methylpropyl)amino]-1H-imidazole-5-carboxamide (959862-23-8)

Conditions	Yield
With sodium cyanoborohydride; acetic acid In methanol at 20℃; for 19h;	90%

5-amino-1H-imidazole-4-carboxamide monohydrochloride (72-40-2) + 2-Fluorobenzaldehyde (446-52-6) → 5-[N-(2-fluorobenzylidene)amino]imidazole-4-carboxamide

Conditions	Yield
With sodium acetate In ethanol; water for 1h; Heating;	89%

5-amino-1H-imidazole-4-carboxamide monohydrochloride (72-40-2) + 5-diazoimidazole-4-carboxamide (7008-85-7) → 5-amino-2-(4carbamoylimidazol-5-ylazo)imidazole-4-carboxamide (87614-68-4)

Conditions	Yield
With sodium acetate buffer at 0 - 5℃;	85%

5-amino-1H-imidazole-4-carboxamide monohydrochloride (72-40-2) + methyl chloroformate (79-22-1) → 5-amino-1-methoxycarbonylimidazole-4-carboxamide (55983-56-7)

Conditions	Yield
With triethylamine In ethanol at 20℃; for 1h;	85%

5-amino-1H-imidazole-4-carboxamide monohydrochloride (72-40-2) + Glycine ethyl ester isocyanate (2949-22-6) → [(5-Amino-4-carbamoyl-imidazole-1-carbonyl)-amino]-acetic acid ethyl ester (157466-96-1)

Conditions	Yield
With triethylamine In dimethyl sulfoxide at 20℃;	85%
With triethylamine In dimethyl sulfoxide at 25℃; for 12h;	80%

2-chloroethyl isothiocyanate (1943-83-5) + 5-amino-1H-imidazole-4-carboxamide monohydrochloride (72-40-2) → 5-Amino-1-[N-(2-chloroethyl)carbamoyl]imidazole-4-carboxamide (188612-57-9)

Conditions	Yield
With triethylamine In acetonitrile at 20℃;	85%
With triethylamine In dimethyl sulfoxide at 25℃;	70%

5-amino-1H-imidazole-4-carboxamide monohydrochloride (72-40-2) + methyl thioisocyanate (556-61-6) → 5-(3-Methyl-thioureido)-1H-imidazole-4-carboxylic acid amide

Conditions	Yield
With triethylamine In dimethyl sulfoxide at 25℃;	85%

trimethylsilyl isocyanate (1118-02-1) + 5-amino-1H-imidazole-4-carboxamide monohydrochloride (72-40-2) → 5-amino-1H-imidazole-1,4-dicarboxamide

Conditions	Yield
With triethylamine In dimethyl sulfoxide at 20℃;	80%

5-amino-1H-imidazole-4-carboxamide monohydrochloride (72-40-2) + Cinnamoyl chloride (102-92-1) → 6-chloro-2-trans-styrylpurine hydrochloride

Conditions	Yield
Stage #1: 5-amino-1H-imidazole-4-carboxamide monohydrochloride; Cinnamoyl chloride With dmap In pyridine at 80℃; for 8h; Stage #2: With potassium hydrogencarbonate In water for 4h; Heating; Stage #3: With trichlorophosphate In N,N-dimethyl-aniline for 1h; Heating;	80%

5-amino-1H-imidazole-4-carboxamide monohydrochloride (72-40-2) + benzaldehyde (100-52-7) → 5-(N-benzylideneamino)imidazole-4-carboxamide

Conditions	Yield
With sodium acetate In ethanol; water for 1h; Heating;	80%

5-amino-1H-imidazole-4-carboxamide monohydrochloride (72-40-2) + Triethyl orthoacetate (78-39-7) → 5-(methyl(ethoxy)methylene)-aminoimidazole-4-carboxamide (117987-01-6)

Conditions	Yield
In N,N-dimethyl-formamide at 180℃; for 0.25h;	80%
In N,N-dimethyl-formamide at 170 - 180℃; for 0.25h;

5-amino-1H-imidazole-4-carboxamide monohydrochloride (72-40-2) → 5-diazoimidazole-4-carboxamide (7008-85-7)

Conditions	Yield
With hydrogenchloride; sodium nitrite In water at 0℃;	79%
With hydrogenchloride; sodium nitrite In water at 0℃; for 0.1h;	60%
With hydrogenchloride; sodium nitrite

5-amino-1H-imidazole-4-carboxamide monohydrochloride (72-40-2) + Hexanoyl chloride (142-61-0) → 6-chloro-2-n-pentylpurine hydrochloride

Conditions	Yield
Stage #1: 5-amino-1H-imidazole-4-carboxamide monohydrochloride; Hexanoyl chloride With dmap In pyridine at 80℃; for 8h; Stage #2: With potassium hydrogencarbonate In water for 4h; Heating; Stage #3: With trichlorophosphate In N,N-dimethyl-aniline for 1h; Heating;	78%

ethyl N-benzyloxycarbonylamino-orthoacetate (13347-35-8) + 5-amino-1H-imidazole-4-carboxamide monohydrochloride (72-40-2) → 2-(N-benzyloxycarbonylaminomethyl)hypoxanthine

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 1h;	77%

potassium ethyl xanthogenate (140-89-6) + 5-amino-1H-imidazole-4-carboxamide monohydrochloride (72-40-2) → 2-mercapto-1,9-dihydro-6H-purin-6-one (2487-40-3)

Conditions	Yield
In N,N-dimethyl-formamide at 140℃; for 5h;	77%

1,3-dibenzyloxy-2-(chloromethoxy)propane (74564-16-2) + 5-amino-1H-imidazole-4-carboxamide monohydrochloride (72-40-2) → 5-amino-1-<<1,3-bis(benzyloxy)-2-propoxy>methyl>-1H-imidazole-4-carboxamide

Conditions	Yield
With potassium hydroxide In N,N-dimethyl-formamide at 0 - 5℃; for 0.5h;	75%

5-amino-1H-imidazole-4-carboxamide monohydrochloride (72-40-2) + ethyl isocyanate (109-90-0) → 5-amino-N 1-ethyl-1H-imidazole-1,4-dicarboxamide (188612-55-7)

Conditions	Yield
With triethylamine In dimethyl sulfoxide at 25℃;	75%
With triethylamine In acetonitrile at 20℃;	45%

5-amino-1H-imidazole-4-carboxamide monohydrochloride (72-40-2) + acetic anhydride (108-24-7) → 5-Acetylamino-1H-imidazole-4-carboxamide hydrochloride (96960-72-4)

Conditions	Yield
In acetic acid for 2h; Heating;	74%

5-amino-1H-imidazole-4-carboxamide monohydrochloride (72-40-2) → C4H3N4(15)NO

Conditions	Yield
With hydrogenchloride; sodium (15)N-nitrite In water at 0 - 5℃; for 0.833333h;	74%

5-amino-1H-imidazole-4-carboxamide monohydrochloride (72-40-2) + cyclohexanylcarbonyl chloride (2719-27-9) → 6-chloro-2-cyclohexylpurine hydrochloride

Conditions	Yield
Stage #1: 5-amino-1H-imidazole-4-carboxamide monohydrochloride; cyclohexanylcarbonyl chloride With dmap In pyridine at 80℃; for 8h; Stage #2: With potassium hydrogencarbonate In water for 4h; Heating; Stage #3: With trichlorophosphate In N,N-dimethyl-aniline for 1h; Heating;	73%

5-amino-1H-imidazole-4-carboxamide monohydrochloride (72-40-2) + 2-methoxy-2-methylpropionaldehyde (36133-35-4) → 4-[(2-methoxy-2-methylpropyl)amino]-1H-imidazole-5-carboxamide (959862-26-1)

Conditions	Yield
With sodium cyanoborohydride; acetic acid In methanol at 20℃; for 20.5h;	73%

Upstream product

• 360-97-4 5-Aminoimidazole-4-carboxamide 

Downstream Products

• 2268-14-6 2-trifluoromethyl-1,7-dihydro-purin-6-one 
• 4656-86-4 2-azohypoxanthine 
• 118966-30-6 5-amino-1-<<2-(acetyloxy)ethoxy>methyl>-1H-imidazole-4-carboxamide 
• 2268-14-6 1,9-dihydro-2-(trifluoromethyl)-6H-purin-6-one 
• 3815-69-8 5-amino-1-(phenylmethyl)-1H-imidazole-4-carboxamide 
• 2487-40-3 2,3-dihydro-2-thioxo-9H-purine-6(1H)-one 
• 55418-16-1 2,4-dimethylimidazo[1,5-a]pyrimidine-8-carboxamide 
• 173409-61-5 5-amino-1-(2-fluorobenzyl)imidazole-4-carboxamide 
• 188612-53-5 5-amino-N₁-methyl-1H-imidazole-1,4-dicarboxamide 
• 188612-59-1 5-Amino-1-(N-benzylcarbamoyl)imidazole-4-carboxamide 
• 7008-85-7 5-diazoimidazole-4-carboxamide 
• 5167-18-0 2-Methyl-hypoxanthin 
• 117987-01-6 5-(methyl(ethoxy)methylene)-aminoimidazole-4-carboxamide 
• 91026-75-4 5-(p-Nitrobenzamido)imidazole-4-carboxamide 

Relevant articles and documents

Development of a One-Step Synthesis of 5-Amino-1 H-imidazole-4-carboxamide

An innovative and efficient synthesis of 5-amino-1H-imidazole-4-carboxamide (AIC) from commercially available hypoxanthine (～$30/kg) is described. The development of the key hydrolysis step and a practical isolation enables a highly efficient one-step manufacturing process for AIC with minimal environmental impact and significant reduction of production cost.