16082-33-0

Basic information

• Product Name: 3,5-Diamino-1H-pyrazole
• Synonyms: 3,5-Diamino-1H-pyrazole;1H-pyrazole-3,5-diamine
• CAS NO: 16082-33-0
• Molecular Formula: C₃H₆N₄
• Molecular Weight: 98.11
• Mol File: 16082-33-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 484.95 °C at 760 mmHg
• Flash Point: 278.849 °C
• Appearance: /
• Density: 1.496
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.771
• Storage Temp.: 2-8°C(protect from light)
• PKA: 16.56±0.10(Predicted)
• CAS DataBase Reference: 3,5-Diamino-1H-pyrazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Diamino-1H-pyrazole(16082-33-0)
• EPA Substance Registry System: 3,5-Diamino-1H-pyrazole(16082-33-0)

Safety Data

• Hazardous Substances Data: 16082-33-0(Hazardous Substances Data)

Usage

General Description

3,5-Diamino-1H-pyrazole is a chemical compound with the formula C3H6N4. It is a white to off-white crystalline powder with a melting point of 300-302°C. 3,5-Diamino-1H-pyrazole is a key intermediate in the synthesis of pharmaceuticals and agrochemicals. It is also used as a building block for the production of dyes, pigments, and other specialty chemicals. 3,5-Diamino-1H-pyrazole is considered to be a potential mutagen, and special care should be taken when handling and using this compound in laboratory and industrial settings.

InChI:InChI=1/C3H6N4/c4-2-1-3(5)7-6-2/h1H,(H5,4,5,6,7)

Synthetic route

malononitrile (109-77-3) → 1H-pyrazole-3,5-diamine (16082-33-0)

Conditions	Yield
With ethanol; hydrazine hydrate

3.5-bis-ethoxycarbonylimino-pyrazolidine → 1H-pyrazole-3,5-diamine (16082-33-0)

Conditions	Yield
With barium dihydroxide

Malondiimidsaeure-diethylester (26315-24-2) → 1H-pyrazole-3,5-diamine (16082-33-0)

Conditions	Yield
With hydrazine In ethanol at 4℃; for 16.1667h;
Stage #1: Malondiimidsaeure-diethylester With potassium carbonate In diethyl ether at 0℃; Saturated solution; Stage #2: With hydrazine hydrate In ethanol Reflux;

1H-pyrazole-3,5-diamine (16082-33-0) + (E)-2-Benzoyl-3-(3,4,5-trimethoxy-phenyl)-acrylonitrile → 2-Benzoyl-3-(3,4,5-trimethoxyphenyl)-3-(3,5-diaminopyrazol-4-yl)propionitril

Conditions	Yield
In ethanol at 40℃; for 0.333333h;	87%

1H-pyrazole-3,5-diamine (16082-33-0) + Ethyl 3-ethoxy-3-iminopropionate (27317-59-5) → 2,5-Diamino-pyrazolo<1,5-a>pyrimidin-7(4H)-on

Conditions	Yield
In ethanol Heating;	58.1%

1H-pyrazole-3,5-diamine (16082-33-0) + ethyl 3-oxo-3-phenylpropionate (94-02-0) + acetic acid (64-19-7) → C14H12N4O2 (934293-50-2)

Conditions	Yield
for 5h; Heating / reflux;	35%

1H-pyrazole-3,5-diamine (16082-33-0) + (4aS,6aS,6bR,13aR)-12-amino-2,2,6a,6b,9,9,13a-heptamethyl-2,3,4,4a,5,6,6a,6b,7,8,8a,9,11,13,13a,13b,14,15b-octadecahydro-1H-chryseno[1,2-f]indazole-4-a-carbonyl chloride → (4aS,6aS,6bR,13aR)-12-amino-N-(3-amino-1H-pyrazol-5-yl)-2,2,6a,6b,9,9,13a-heptamethyl-2,3,4,4a,5,6,6a,6b,7,8,8a,9,11,13,13a,13b,14,15b-octadecahydro-1H-chryseno[1,2-f]indazole-4-a-carboxamide

Conditions	Yield
In pyridine at 20℃;	25%

1H-pyrazole-3,5-diamine (16082-33-0) + (4aS,6aS,6bR,13aR)-12-amino-2,2,6a,6b,9,9,13a-heptamethyl-2,3,4,4a,5,6,6a,6b,7,8,8a,9,11,13,13a,13b,14,15b-octadecahydro-1H-chryseno[1,2-f]indazole-4a-carbonyl chloride (1415383-28-6) → (4aS,6aS,6bR,13aR)-12-amino-N-(3-amino-1H-pyrazol-5-yl)-2,2,6a,6b,9,9,13a-heptamethyl-2,3,4,4a,5,6,6a,6b,7,8,8a,9,11,13,13a,13b,14,15b-octadecahydro-1H-chryseno[1,2-f]indazole-4a-carboxamide (1415382-84-1)

Conditions	Yield
With pyridine In pyridine at 20℃;	25%

1H-pyrazole-3,5-diamine (16082-33-0) + potassium cyanate (590-28-3) → N,N''-(1H-pyrazole-3,5-diyl)-di-urea

Conditions	Yield
With hydrogenchloride

1H-pyrazole-3,5-diamine (16082-33-0) + benzoyl chloride (98-88-4) → N,N'-(1H-pyrazole-3,5-diyl)-bis-benzamide

Conditions	Yield
With sodium hydroxide

1H-pyrazole-3,5-diamine (16082-33-0) → 3,5-diamino-4-iodopyrazole

Conditions	Yield
With bis(pyridine)iodonium(I)tetrafluoroborate In dimethyl sulfoxide for 5h; Ambient temperature;

4-methyl-8-(morpholin-4-ylsulfonyl)-furo[3,4-c]quinoline-1,3-dione (753482-69-8) + 1H-pyrazole-3,5-diamine (16082-33-0) → 2-(5-amino-1H-pyrazol-3-yl)-4-methyl-8-(morpholine-4-sulfonyl)-pyrrolo[3,4-c]quinoline-1,3-dione

Conditions	Yield
Stage #1: 4-methyl-8-(morpholin-4-ylsulfonyl)-furo[3,4-c]quinoline-1,3-dione; 1H-pyrazole-3,5-diamine With pyridine at 20℃; for 0.5h; Stage #2: With acetic anhydride for 3h; Heating;

1H-pyrazole-3,5-diamine (16082-33-0) + trifluoroacetic anhydride (407-25-0) → N-(5-amino-1H-pyrazol-3-yl)-2,2,2-trifluoro-acetamide (452913-45-0)

1H-pyrazole-3,5-diamine (16082-33-0) + 5-(2,3-difluoro-phenyl)-3-oxo-pentanoic acid ethyl ester (412950-62-0) + acetic acid (64-19-7) → N-{5-[2-(2,3-difluoro-phenyl)-ethyl]-7-hydroxy-pyrazolo[1,5-a]pyrimidin-2-yl}acetamide (1185908-04-6)

Conditions	Yield
at 100℃; for 18h;

1H-pyrazole-3,5-diamine (16082-33-0) + sodium (1,3-dioxopropan-2-ylidyne)azinate monohydrate → 5-nitro-1H-pyrazolo[3,4-b]pyridin-3-amine

Conditions	Yield
With acetic acid at 90℃; for 6h; Sealed tube;	0.91 g

1H-pyrazole-3,5-diamine (16082-33-0) + 1,3-dimethyluracil (874-14-6) → 2-amino-4H,5H-pyrazolo[1,5-a]pyrimidin-5-one

Conditions	Yield
With sodium ethanolate In ethanol at 80℃; for 15h;

1H-pyrazole-3,5-diamine (16082-33-0) + 1,3-dimethyluracil (874-14-6) → 2-aminopyrazolo[1,5-a]pyrimidin-5-ol

Conditions	Yield
With sodium ethanolate In ethanol at 80℃;

Upstream product

• 26315-24-2 Malondiimidsaeure-diethylester 
• 109-77-3 malononitrile 

Downstream Products

• 934293-50-2 C₁₄H₁₂N₄O₂ 
• 1186608-97-8 5-nitro-1H-pyrazolo[3,4-b]pyridin-3-amine 
• 1185908-04-6 N-{5-[2-(2,3-difluoro-phenyl)-ethyl]-7-hydroxy-pyrazolo[1,5-a]pyrimidin-2-yl}acetamide 

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