15454-54-3

Basic information

• Product Name: 5-AMINOTETRAZOLE MONOHYDRATE
• Synonyms: 5-TETRAZOLAMINE MONOHYDRATE;5-AMINO-1H-TETRAZOLE HYDRATE;5-AMINO-1H-TETRAZOLE MONOHYDRATE;5-AMINOTETRAZOLE MONOHYDRATE;1H-TETRAZOLE-5-AMINE MONOHYDRATE;tetrazol-5-amine;5-AMINO-1H-TETRAZOLE MONOHYDRATE 99%;1H-Tetrazol-5-amine hydrate
• CAS NO: 15454-54-3
• Molecular Formula: CH₃N₅*H₂O
• Molecular Weight: 103.08
• EINECS: 224-581-7
• Mol File: 15454-54-3.mol
• Article Data: 0

Chemical Properties

• Melting Point: 198204°Cdec.
• Boiling Point: 488.8 °C at 760 mmHg
• Flash Point: 249.4 °C
• Appearance: /
• Vapor Pressure: 2.29E-10mmHg at 25°C
• Storage Temp.: 2-8°C
• Water Solubility: Soluble in water, ethanol (1.36%).
• BRN: 108872
• CAS DataBase Reference: 5-AMINOTETRAZOLE MONOHYDRATE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-AMINOTETRAZOLE MONOHYDRATE(15454-54-3)
• EPA Substance Registry System: 5-AMINOTETRAZOLE MONOHYDRATE(15454-54-3)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38
• Safety Statements: 26
• RIDADR: UN 1325 4.1/PG 2
• WGK Germany: 3
• RTECS: XF7465000
• TSCA: Yes
• HazardClass: 4.1
• PackingGroup: III
• Hazardous Substances Data: 15454-54-3(Hazardous Substances Data)

Usage

Chemical Properties

White to light yellow poowder

Uses

5-Aminotetrazole monohydrate is a useful reagent in condensation reactions to form pyrimidines.

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

• 288-94-8 1H-tetrazole 
• 13958-60-6 N-(1⁽²⁾H-tetrazol-5-yl)-formamide 
• 76575-42-3 4-oxo-2-phenyl-N-1H-tetrazol-5-yl-4H-pyrido[1,2-a]thieno[2,3-d]pyrimidine-7-carboxamide 
• 68056-49-5 8-(1H-tetrazol-5-ylcarbamoyl)chinolin 
• 93700-60-8 2-methoxy-N-(tetrazol-5-yl)benzamide 
• 177785-15-8 3-nitro-N-(1H-tetrazol-5-yl)benzamide 
• 87693-22-9 2-methyl-6-nitro-N-1H-tetrazol-5-ylbenzamide 
• 76512-08-8 4-Oxo-5-phenyl-N-(5-tetrazolyl)-4H-pyran-2-carboxamide 
• 89224-56-6 3,7-dimethoxy-4-phenyl-N-(1H-tetrazol-5-yl)-4H-furo[3,2-b]indole-2-carboxamide 
• 87693-28-5 2-nitro-N-(1H-tetrazol-5-yl)-benzamide 
• 6973-21-3 (1H-tetrazol-5-yl)urea 
• 117705-55-2 7-(4-acetyl-2-ethyl-5-hydroxyphenoxy)-N-(1H-tetrazol-5-yl)heptanamide 
• 111374-47-1 6-chloro-N-(1H-tetrazol-5-yl)-2-pyrazinecarboxamide 
• 115172-67-3 <(2-nitrophenyl)sulfonyl>carbamimidic azide