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3-Amino-4-pyrazolecarbonitrile structure
3-Amino-4-pyrazolecarbonitrile structure

3-Amino-4-pyrazolecarbonitrile

Iupac Name:5-amino-1H-pyrazole-4-carbonitrile
CAS No.: 16617-46-2
Molecular Weight:108.10100
Modify Date.: 2022-11-25 01:16
Introduction: 3-Amino-4-pyrazolecarbonitrile has been a useful synthetic intermediate. 3-Amino-4-pyrazolecarbonitrile Preparation Products And Raw materials Preparation Products View more+
1. Names and Identifiers
1.1 Name
3-Amino-4-pyrazolecarbonitrile
1.2 Synonyms

1H-Pyrazole-4-carbonitrile, 3-amino- 3-Amino-1H-pyrazole-4-carbonitrile 3-Amino-4-Ccyanopyrazole 3-amino-4-cyano-1H-pyrazole 3-Amino-4-cyanopyrazole 3-Amino-4-Cyanopyrozale 3-Amino-4-cyanopyrozole (intermediate of zaleplon) 3-Amino-4-cyanopyrrole 3-AMINO-4-PYRAZOLOCARBONITRILE 3-Aminopyrazole-4-Carbonitrile 3-aminopyrazolo-4-carbonitrile 4-cyano-5-aminopyrazole 5-amino-1H-pyrazole-4-carbonitrile 5-AMINO-4-CYANOPYRAZOLE 5-amino-4-pyrazolecarbonitrile 5-aminopyrazole-4-carbonitrile Allopurinol Impurity 7 Allopurinol Nitrile IMpurity Amino-1H-Pyrazole-4-Carbonitrile EINECS 240-665-6 MFCD00005237 pyrazolecarbonitrile Zaleplon intermediate

1.3 CAS No.
16617-46-2
1.4 CID
85515
1.5 EINECS(EC#)
240-665-6
1.6 Molecular Formula
C4H4N4 (isomer)
1.7 Inchi
InChI=1S/C4H4N4/c5-1-3-2-7-8-4(3)6/h2H,(H3,6,7,8)
1.8 InChkey
FFNKBQRKZRMYCL-UHFFFAOYSA-N
1.9 Canonical Smiles
C1=NNC(=C1C#N)N
1.10 Isomers Smiles
C1=NNC(=C1C#N)N
2. Properties
2.1 Density
1.42g/cm3
2.1 Melting point
172-174°C(lit.)
2.1 Boiling point
476.37ºC at 760 mmHg
2.1 Refractive index
1.621
2.1 Flash Point
476.37 °C at 760 mmHg
2.1 Precise Quality
108.04400
2.1 PSA
78.49000
2.1 logP
0.44478
2.1 Appearance
Crystalline Solid
2.2 Storage
Ambient temperatures.
2.3 Chemical Properties
Tan Crystalline Solid
2.4 Color/Form
Light yellow to brown-orange
2.5 pKa
11.58±0.50(Predicted)
2.6 Stability
Stable at room temperature in closed containers under normal storage and handling conditions.
2.7 StorageTemp
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
3. Use and Manufacturing
3.1 Methods of Manufacturing
Hydrazine (5 g, 0.156 mol) was carefully added into 2-(ethoxymethylene)malononitrile (8.64 g, 0.070 mol) in ethanol and heated on the steam-bath for 30 min. After completion of the reaction, white precipitate was gradually appeared that kept in a refrigerator overnight. The product was then filtered and washed with a small amount of cold ethanol to afford the desired product 5-amino-1H-pyrazole-4-carbonitrile (1) as white solid; (3.05 g, 86percent); mp 168-170 °C (Lit. mp 169-170 °C) [33].Ethoxy methylene malonic eye 15.0g (0.12 μM) is slowly added at room temperature to 85percent hydrazine hydrate 12 ml (0.25 μM) in, the water bath heating reflux reaction 1h, in the reaction system by adding 10 ml of water. Placed in the refrigerator overnight, filtered, washing the filter cake, washing the yellow solid 10.6g, yield 81.7percent. The resulting spectrogram consistent with literature reports.Ν2Η42Ο (33 g, 640 mmol) was added to a solution of 2- (ethoxymethylene)malononitrile (20 g, 163.77 mmol) in acetic acid (200 mL) and the reaction was stirred overnight at 85°C. The resulting mixture was concentrated in vacuo and the residue was diluted with HTo 2-(ethoxymethylene)propanedinitrile (20 g, 163.80 mmol) was added hydrazine hydrate (15.9 mL, 327.60 mmol) dropwise at 0 °C and the resultant reaction mixture was heated at 100 °C in a closed reagent bottle for 1 h. The reaction was monitored by TLC. After completion of reaction, the mixture was cooled to RT and water (50 mL) was added to the reaction mixture. The product was extracted using EtOAc (3x200 mL). The combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 15 g of 5-amino-1H-pyrazole-4-carbonitrile as a light brown solid.To 2-(ethoxymethylene)propanedinitrile (20 g, 163.80 mmol) was added hydrazine hydrate (15.9 mL, 327.60 mmol) dropwise at 0 °C and the resultant reaction mixture was heated at 100 °C in a closed reagent bottle for 1h. The reaction was monitored by TLC. After completion, the reaction mixture was cooled to RT and water (50 mL) was added. The product was extracted using EtOAc (3x200 mL). The combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 15 g of 5- amino-1H-pyrazole-4-carbonitrile as a light brown solid.Add malononitrile (16.5 g, 0.25 mol), triethyl orthoformate (38 g, 0.29 mol) and acetic anhydride (55 g, 0.54 mol) to a 1 L three-necked flask, slowly heat to 115 °C, reflux reaction for 2 h .The temperature of the mixture was lowered to 20 °C, hydrazine hydrate (15.5 g, 0.31 mol) was added dropwiseover 40minutes, and the temperature was maintained at 18-22 °C.The reaction was then carried out at 20-30 ° C for 18 h.Thereaction wasmonitoredbyTLC, neutralized with a sodium hydroxide aqueous solution (36 g of sodium hydroxide in 72 ml of water) at 25 °C to obtain a prize mixture, and the mixture washeated and azeotropically distilled to collect 45 ml fractions.This fraction was cooled at 0 to 5 ° C for 1.5 h, and a pale brown solid was collected, rinsedwithcold water and dried to give product (19.2 g, 72percent yield).
3.2 Usage
3-Amino-4-pyrazolecarbonitrile has been a useful synthetic intermediate. 3-Amino-4-pyrazolecarbonitrile Preparation Products And Raw materials Preparation Products
4. Safety and Handling
4.1 Hazard Codes
Xn
4.1 Risk Statements
R20/21
4.1 Safety Statements
S22-S24/25-S23
4.1 Packing Group
III
4.1 Hazard Class
6.1
4.1 Hazard Declaration
H301+H311+H331
4.1 RIDADR
3439
4.1 Caution Statement
P261, P264, P270, P271, P280, P301+P310, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P311, P312, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, P501
4.1 WGK Germany
3
4.1 Safety

Hazard Codes:?HarmfulXn,ToxicT
Risk Statements: 20/21/22-20/21-36/37/38
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.?
R20/21:Harmful by inhalation and in contact with skin.?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 22-24/25-23-36-26
S22:Do not breathe dust.?
S24/25:Avoid contact with skin and eyes.?
S23:Do not breathe vapour.?
S36:Wear suitable protective clothing.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR: 3439
WGK Germany: 3
F: 10
HazardClass: 6.1
PackingGroup: III
HS Code: 29331990

4.2 Specification

? 3-Amino-4-pyrazolecarbonitrile , with CAS number of 16617-46-2, can be called 1H-pyrazole-4-carbonitrile, 3-amino- ; 5-Amino-1H-pyrazole-4-carbonitrile ; 3-Amino-1H-pyrazole-4-carbonitrile . It is a?crystalline solid and be?a useful synthetic intermediate.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H302 Harmful if swallowed

H315 Causes skin irritation

H319 Causes serious eye irritation

H335 May cause respiratory irritation

Precautionary statement(s)
Prevention

none

Response

none

Storage

none

Disposal

none

2.3 Other hazards which do not result in classification

none

9. Other Information
9.0 Storage Conditions
Hydrazine (5 g, 0.156 mol) was carefully added into 2-(ethoxymethylene)malononitrile (8.64 g, 0.070 mol) in ethanol and heated on the steam-bath for 30 min. After completion of the reaction, white precipitate was gradually appeared that kept in a refrigerator overnight. The product was then filtered and washed with a small amount of cold ethanol to afford the desired product 5-amino-1H-pyrazole-4-carbonitrile (1) as white solid; (3.05 g, 86percent); mp 168-170 °C (Lit. mp 169-170 °C) [33].Ethoxy methylene malonic eye 15.0g (0.12 μM) is slowly added at room temperature to 85percent hydrazine hydrate 12 ml (0.25 μM) in, the water bath heating reflux reaction 1h, in the reaction system by adding 10 ml of water. Placed in the refrigerator overnight, filtered, washing the filter cake, washing the yellow solid 10.6g, yield 81.7percent. The resulting spectrogram consistent with literature reports.Ν2Η42Ο (33 g, 640 mmol) was added to a solution of 2- (ethoxymethylene)malononitrile (20 g, 163.77 mmol) in acetic acid (200 mL) and the reaction was stirred overnight at 85°C. The resulting mixture was concentrated in vacuo and the residue was diluted with HTo 2-(ethoxymethylene)propanedinitrile (20 g, 163.80 mmol) was added hydrazine hydrate (15.9 mL, 327.60 mmol) dropwise at 0 °C and the resultant reaction mixture was heated at 100 °C in a closed reagent bottle for 1 h. The reaction was monitored by TLC. After completion of reaction, the mixture was cooled to RT and water (50 mL) was added to the reaction mixture. The product was extracted using EtOAc (3x200 mL). The combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 15 g of 5-amino-1H-pyrazole-4-carbonitrile as a light brown solid.To 2-(ethoxymethylene)propanedinitrile (20 g, 163.80 mmol) was added hydrazine hydrate (15.9 mL, 327.60 mmol) dropwise at 0 °C and the resultant reaction mixture was heated at 100 °C in a closed reagent bottle for 1h. The reaction was monitored by TLC. After completion, the reaction mixture was cooled to RT and water (50 mL) was added. The product was extracted using EtOAc (3x200 mL). The combined organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 15 g of 5- amino-1H-pyrazole-4-carbonitrile as a light brown solid.Add malononitrile (16.5 g, 0.25 mol), triethyl orthoformate (38 g, 0.29 mol) and acetic anhydride (55 g, 0.54 mol) to a 1 L three-necked flask, slowly heat to 115 °C, reflux reaction for 2 h .The temperature of the mixture was lowered to 20 °C, hydrazine hydrate (15.5 g, 0.31 mol) was added dropwiseover 40minutes, and the temperature was maintained at 18-22 °C.The reaction was then carried out at 20-30 ° C for 18 h.Thereaction wasmonitoredbyTLC, neutralized with a sodium hydroxide aqueous solution (36 g of sodium hydroxide in 72 ml of water) at 25 °C to obtain a prize mixture, and the mixture washeated and azeotropically distilled to collect 45 ml fractions.This fraction was cooled at 0 to 5 ° C for 1.5 h, and a pale brown solid was collected, rinsedwithcold water and dried to give product (19.2 g, 72percent yield).
9.1 Mesh Entry Terms
5-amino-4-cyanopyrazole
9.2 Manufacturing Info
1H-Pyrazole-4-carbonitrile, 3-amino-: INACTIVE
9.3 BRN
2647
9.4 Chemical Properties
Tan Crystalline Solid
9.5 Uses
A useful synthetic intermediate
10. Computational chemical data
  • Molecular Weight: 108.10100g/mol
  • Molecular Formula: C4H4N4
  • Compound Is Canonicalized: True
  • XLogP3-AA: 0.1
  • Exact Mass: 108.043596145
  • Monoisotopic Mass: 108.043596145
  • Complexity: 123
  • Rotatable Bond Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Topological Polar Surface Area: 78.5
  • Heavy Atom Count: 8
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADcYBjgAAAAAAAAAAAAAAAAAAAAWAAAAAAAAAAAAAAAAABgAAAHAAYAAAADADBGgQtsJBjAACyBhJnYACwBAKAgAAUMSAgRBAAgIAAQEAAhAAQCAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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(2S)-5-Amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-4-amino-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2R)-2-amino-3-sulfanylpropanoyl]amino]-4-oxobutanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-3-methylbutanoyl]amino]propanoyl]amino]propanoyl]amino]propanoyl]amino]-3-hydroxypropanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-3-methylpentanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-5-oxopentanoyl]amino]-4-oxobutanoyl]amino]-5-oxopentanoyl]amino]-3-phenylpropanoyl]amino]-3-methylbutanoyl]amino]-5-oxopentanoic acid;2,2,2-trifluoroacetic acid
143257-74-3 (2S)-5-Amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-4-amino-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2R)-2-amino-3-sulfanylpropanoyl]amino]-4-oxobutanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-3-methylbutanoyl]amino]propanoyl]amino]propanoyl]amino]propanoyl]amino]-3-hydroxypropanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-3-methylpentanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-5-oxopentanoyl]amino]-4-oxobutanoyl]amino]-5-oxopentanoyl]amino]-3-phenylpropanoyl]amino]-3-methylbutanoyl]amino]-5-oxopentanoic acid;2,2,2-trifluoroacetic acid
(2S)-2-[[2-[[(2S)-6-Amino-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-4-amino-2-[[(2S,3S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-4-methylpentanoyl]amino]-3-hydroxypropanoyl]amino]-4-carboxybutanoyl]amino]-4-methylpentanoyl]amino]-3-methylpentanoyl]amino]-3-methylpentanoyl]amino]-4-oxobutanoyl]amino]-4-oxobutanoyl]amino]propanoyl]amino]-3-hydroxybutanoyl]amino]-4-carboxybutanoyl]amino]-4-carboxybutanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]-3-methylpentanoyl]amino]hexanoyl]amino]acetyl]amino]-4-methylpentanoic acid
175922-65-3 (2S)-2-[[2-[[(2S)-6-Amino-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-4-amino-2-[[(2S,3S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-4-methylpentanoyl]amino]-3-hydroxypropanoyl]amino]-4-carboxybutanoyl]amino]-4-methylpentanoyl]amino]-3-methylpentanoyl]amino]-3-methylpentanoyl]amino]-4-oxobutanoyl]amino]-4-oxobutanoyl]amino]propanoyl]amino]-3-hydroxybutanoyl]amino]-4-carboxybutanoyl]amino]-4-carboxybutanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]-3-methylpentanoyl]amino]hexanoyl]amino]acetyl]amino]-4-methylpentanoic acid