15454-54-3

Usage

Uses

Used in Chemical Synthesis:
5-Aminotetrazole monohydrate is used as a reagent in condensation reactions for the formation of pyrimidines, which are important heterocyclic compounds with a wide range of applications in the pharmaceutical and chemical industries. These pyrimidines can be further utilized in the synthesis of various biologically active molecules, including pharmaceuticals and agrochemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 5-Aminotetrazole monohydrate is used as a building block for the synthesis of various drug candidates. The pyrimidines formed through condensation reactions involving 5-AMINOTETRAZOLE MONOHYDRATE can be incorporated into the molecular structures of potential therapeutic agents, targeting a variety of diseases and medical conditions.
Used in Agrochemical Industry:
Similarly, in the agrochemical industry, 5-Aminotetrazole monohydrate is employed in the synthesis of active ingredients for pesticides, herbicides, and other crop protection products. The pyrimidines derived from 5-AMINOTETRAZOLE MONOHYDRATE can be used to develop novel molecules with improved efficacy and selectivity, contributing to more effective and environmentally friendly agricultural practices.

InChI:InChI=1/CH3N5.H2O/c2-1-3-5-6-4-1;/h(H3,2,3,4,5,6);1H2

Synthetic route

1,5-dihydro-1,5-dioxo-4-methyl-1-benzopyrano[3,4-b]pyridine-2-carboxylic acid (75704-60-8) + 1,5-dihydro-1,5-dioxo-N-1H-tetrazol-5-yl-4H-[1]benzopyrano[3,4-b]pyridine-2-carboxamide (75704-66-4) + 5-amino-1H-tetrazole monohydrate (15454-54-3) + 1,1'-carbonyldiimidazole (530-62-1) → 1,5-dihydro-4-methyl-1,5-dioxo-N-1H-tetrazol-5-yl-4H-[1]benzopyrano[3,4-b]pyridine-2-carboxamide (75704-67-5)

Conditions	Yield
In N-methyl-acetamide	95%

5-amino-1H-tetrazole monohydrate (15454-54-3) + 2-Nitrobenzenesulfonyl chloride (1694-92-4) → <(2-nitrophenyl)sulfonyl>carbamimidic azide (115172-67-3)

Conditions	Yield
In tetrahydrofuran; water	76%

2-(ethoxymethylene)-1H-indene-1,3(2H)-dione (59117-83-8) + 5-amino-1H-tetrazole monohydrate (15454-54-3) → 2-<(1H-tetrazol-5-ylamino)methylene>-1,3-indandione (130749-17-6)

Conditions	Yield
With acetic acid In ethanol for 1h; Heating;	75%

5-amino-1H-tetrazole monohydrate (15454-54-3) + benzenesulfonyl chloride (98-09-9) → 2-(phenylsulfonyl)carbamimidic azide

Conditions	Yield
In tetrahydrofuran; water 1.) reflux, 30 min.; 2.) room temp., 15 h.;	73%

5-amino-1H-tetrazole monohydrate (15454-54-3) + 2-acetyl-indan-1,3-dione (1133-72-8) → 10-Methyl-1,2,3,4,10a-pentaaza-cyclopenta[b]fluoren-9-one (130749-12-1)

Conditions	Yield
With acetic acid In ethanol for 48h; Heating;	63%

3-methoxy-1-(phenylmethyl)-1H-indole-2-carboxylic acid + 5-amino-1H-tetrazole monohydrate (15454-54-3) + 1,1'-carbonyldiimidazole (530-62-1) → 3-Methoxy-1-(phenylmethyl)-N-1H-tetrazol-5-yl-1H-indole-2-carboxamide

Conditions	Yield
In N,N-dimethyl-formamide	63%

formaldehyd (50-00-0) + 5-amino-1H-tetrazole monohydrate (15454-54-3) + ethyl acetate (141-78-6) → ethyl 5-methyl-4H,7H-[1,2,3,4]tetrazolo[1,5-a]pyrimidine-6-carboxylate

Conditions	Yield
With acetic acid In ethanol; water at 120℃; for 0.166667h; Microwave irradiation;	62%

5-amino-1H-tetrazole monohydrate (15454-54-3) + 3,7-dimethoxy-4-phenyl-4H-furo<3,2-b>indole-2-carboxylic acid (89224-55-5) + 1,1'-carbonyldiimidazole (530-62-1) → 3,7-dimethoxy-4-phenyl-N-(1H-tetrazol-5-yl)-4H-furo[3,2-b]indole-2-carboxamide (89224-56-6)

Conditions	Yield
In N,N-dimethyl-formamide	61%

5-amino-1H-tetrazole monohydrate (15454-54-3) + squaric acid (2892-51-5) + zinc(II) chloride (7646-85-7) → C5HN5O3(2-)*Zn(2+)*3H2O

Conditions	Yield
In water for 24h; Autoclave;	61%

cobalt(II) chloride hexahydrate + 5-amino-1H-tetrazole monohydrate (15454-54-3) + squaric acid (2892-51-5) → C5HN5O3(2-)*3H2O*Co(2+)

Conditions	Yield
In water for 24h; Autoclave;	57%

2-propanoylindan-1,3-dione (2740-25-2) + 5-amino-1H-tetrazole monohydrate (15454-54-3) → 10-Ethyl-1,2,3,4,10a-pentaaza-cyclopenta[b]fluoren-9-one (130749-13-2)

Conditions	Yield
With acetic acid In ethanol for 48h; Heating;	56%

1-ferrocenyl-3-(4-methoxyphenyl)prop-2-en-1-one + 5-amino-1H-tetrazole monohydrate (15454-54-3) → (ferrocenyl)(CCH2CH(p-CH3OC6H4)N(N3)CN)

Conditions	Yield
In ethanol soln. of Fe-complex and 5-aminotetrazole monohydrate in absolute ethanol was refluxed for 18 h; filtn., recrystallised from ethanol, elem. anal.;	56%

methyl 2-acetyl-3-methyl-2-butenoate (35491-51-1) + 5-amino-1H-tetrazole monohydrate (15454-54-3) → methyl 5,7,7-trimethyl-4H,7H-[1,2,3,4]tetrazolo[1,5-a]pyrimidine-6-carboxylate

Conditions	Yield
In ethanol for 4h; Reflux;	56%

1,5-dihydro-1,5-dioxo-4-ethyl-1-benzopyrano[3,4-b]pyridine-2-carboxylic acid + 1,5-dihydro-1,5-dioxo-N-1H-tetrazol-5-yl-4H-[1]benzopyrano[3,4-b]pyridine-2-carboxamide (75704-66-4) + 5-amino-1H-tetrazole monohydrate (15454-54-3) + 1,1'-carbonyldiimidazole (530-62-1) → 4-Ethyl-1,5-dihydro-1,5-dioxo-N-(1H-tetrazol-5-yl)-4H-[1]benzopyrano[3,4-b]pyridine-2-carboxamide

Conditions	Yield
In N-methyl-acetamide	55%

2-isovalerylindane-1,3-dione (83-28-3) + 5-amino-1H-tetrazole monohydrate (15454-54-3) → 10-Isobutyl-1,2,3,4,10a-pentaaza-cyclopenta[b]fluoren-9-one (130749-14-3)

Conditions	Yield
With acetic acid In ethanol for 72h; Heating;	51%

5-amino-1H-tetrazole monohydrate (15454-54-3) + dimethyl sulfate (77-78-1) → 2-methyl-2H-tetrazole-5-amine (6154-04-7) + 1-methyl-5-amino-1H-tetrazole (5422-44-6)

Conditions	Yield
With phenolphthalein; sodium hydroxide In water for 1h; Reflux;	A 25% B 51%

pindone (83-26-1) + 5-amino-1H-tetrazole monohydrate (15454-54-3) → 2-Azido-4-tert-butyl-indeno[1,2-d]pyrimidin-5-one

Conditions	Yield
With acetic acid In ethanol for 72h; Heating;	50%

5-amino-1H-tetrazole monohydrate (15454-54-3) → sodium 5-nitro-2H-1,2,3,4-tetrazol-2-ide (67312-43-0)

Conditions	Yield
With sulfuric acid; sodium nitrite In water at 70 - 72℃;	50%

3,6-dimethoxybenzofuran-2-carboxylic acid (104796-46-5) + 5-amino-1H-tetrazole monohydrate (15454-54-3) + 1,1'-carbonyldiimidazole (530-62-1) → 3,6-dimethoxy-N-1H-tetrazol-5-yl-2-benzofurancarboxamide + 3,6-dimethoxy-N-1Htetrazol-5-yl-2-benzofurancarboxamide (104796-69-2)

Conditions	Yield
In N,N-dimethyl-formamide	A n/a B 43%

5-amino-1H-tetrazole monohydrate (15454-54-3) + 1,5-dihydro-1,5-dioxo-4H-1-benzopyrano[3,4-b]pyridine-3-carboxylic acid (75945-10-7) + 1,1'-carbonyldiimidazole (530-62-1) → 1,5-Dihydro-1,5-dioxo-N-1H-tetrazol-5-yl-4H-[1]benzopyrano-[3,4-b]pyridine-3-carboxamide (75945-13-0)

Conditions	Yield
In N-methyl-acetamide	39%

2-benzoyl-1,3-indanedione (1785-95-1) + 5-amino-1H-tetrazole monohydrate (15454-54-3) → 2-Azido-4-phenyl-indeno[1,2-d]pyrimidin-5-one

Conditions	Yield
With acetic acid In ethanol for 48h; Heating;	38%

5-amino-1H-tetrazole monohydrate (15454-54-3) + 3-methoxy-4-methyl-4H-furo<3,2-b>indole-2-carboxylic acid (89224-64-6) + 1,1'-carbonyldiimidazole (530-62-1) → 3-Methoxy-4-methyl-N-(1H-tetrazol-5-yl)-4H-furo[3,2-b]indole-2-carboxamide (89224-65-7)

Conditions	Yield
In N,N-dimethyl-formamide	38%

5-amino-1H-tetrazole monohydrate (15454-54-3) + squaric acid (2892-51-5) + cadmium(II) chloride (10108-64-2) → C5HN5O3(2-)*3H2O*Cd(2+)

Conditions	Yield
In water for 24h; Autoclave;	35%

5-amino-1H-tetrazole monohydrate (15454-54-3) + 1,5-dihydro-1,5-dioxo-4H-1-benzopyrano[3,4-b]pyridine-2-carboxylic acid (75704-62-0) + 1,1'-carbonyldiimidazole (530-62-1) → 1,5-dihydro-1,5-dioxo-N-1H-tetrazol-5-yl-4H-[1]benzopyrano[3,4-b]pyridine-2-carboxamide (75704-66-4)

Conditions	Yield
In N-methyl-acetamide	34%

4-(2-hydroxyphenyl)but-3-en-2-one (22214-28-4, 6051-53-2) + 5-amino-1H-tetrazole monohydrate (15454-54-3) → (5R*,11R*)-(+/-)-5-methyl-4,5-dihydro-11H-5,11-methanotetrazolo[5,1-d][1,3,5]benzoxadiazocine

Conditions	Yield
In N,N-dimethyl-formamide for 2h; Reflux;	34%

5-amino-1H-tetrazole monohydrate (15454-54-3) + methanesulfonyl chloride (124-63-0) → 2-(methylsulfonyl)carbamimidic azide

Conditions	Yield
In tetrahydrofuran for 1h; heating on a steam bath;	20%

sulfur tetrafluoride (7783-60-0) + 5-amino-1H-tetrazole monohydrate (15454-54-3) → S,S-difluoro-N-trifluoromethyl-sulfimide (1512-14-7)

Conditions	Yield
300°C 2 h;	14%

4-(3,5-bis(trifluoromethyl)phenyl)-1-(4-(3,4-dichlorophenyl)-5-(isopropylthio)thiazol-2-yl)-3-methyl-1H-pyrazole-5-carboxamide + 5-amino-1H-tetrazole monohydrate (15454-54-3) → 4-(3,5-bis(trifluoromethyl)phenyl)-1-(4-(3,4-dichlorophenyl)-5-(isopropylthio)thiazol-2-yl)-3-methyl-N-(1H-tetrazol-5-yl)-1H-pyrazole-5-carboxamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 72h;	6%

4-(3,5-bis(trifluoromethyl)phenyl)-1-(4-(3,4-dichlorophenyl)-5-(isopropylthio)thiazol-2-yl)-3-methyl-1H-pyrazole-5-carboxylic acid + 5-amino-1H-tetrazole monohydrate (15454-54-3) → 4-(3,5-bis(trifluoromethyl)phenyl)-1-(4-(3,4-dichlorophenyl)-5-(isopropylthio)thiazol-2-yl)-3-methyl-N-(1H-tetrazol-5-yl)-1H-pyrazole-5-carboxamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃;	6%

2-pyrazylcarboxylic acid (98-97-5) + 5-amino-1H-tetrazole monohydrate (15454-54-3) → N-(1H-tetrazol-5-yl)-2-pyrazinecarboxamide (111374-14-2)

Conditions	Yield
With chloroformic acid ethyl ester; triethylamine 1) THF, 5 deg C, 30 min, 2) room temperature, 28.5 h; Yield given. Multistep reaction;

Downstream Products

• 111374-47-1 6-chloro-N-(1H-tetrazol-5-yl)-2-pyrazinecarboxamide 
• 87693-28-5 2-nitro-N-(1H-tetrazol-5-yl)-benzamide 
• 177785-15-8 3-nitro-N-(1H-tetrazol-5-yl)benzamide 
• 93700-60-8 2-methoxy-N-(tetrazol-5-yl)benzamide 
• 68056-49-5 8-(1H-tetrazol-5-ylcarbamoyl)chinolin 
• 6973-21-3 (1H-tetrazol-5-yl)urea 
• 117705-55-2 7-(4-acetyl-2-ethyl-5-hydroxyphenoxy)-N-(1H-tetrazol-5-yl)heptanamide 
• 288-94-8 1H-tetrazole 
• 115172-67-3 <(2-nitrophenyl)sulfonyl>carbamimidic azide 
• 89224-56-6 3,7-dimethoxy-4-phenyl-N-(1H-tetrazol-5-yl)-4H-furo[3,2-b]indole-2-carboxamide 
• 6154-04-7 2-methyl-2H-tetrazole-5-amine 
• 5422-44-6 1-methyl-5-amino-1H-tetrazole 
• 76575-42-3 4-oxo-2-phenyl-N-1H-tetrazol-5-yl-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxamide 
• 13958-60-6 N-(1⁽²⁾H-tetrazol-5-yl)-formamide