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3-Amino-4-cyanopyrazole

3-Amino-4-cyanopyrazole structure

CAS No:
16617-46-2
Formula:
C4H4N4
Chemical Name:
3-Amino-4-cyanopyrazole
Synonyms:
1H-Pyrazole-4-carbonitrile,3-amino-;Pyrazole-4-carbonitrile,3-amino-;Pyrazole-4-carbonitrile,3(or 5)-amino-;3-Amino-1H-pyrazole-4-carbonitrile;3-Amino-4-cyanopyrazole;5-Amino-4-cyanopyrazole;3-Amino-4-pyrazolecarbonitrile;5-Amino-4-pyrazolecarbonitrile;3-Aminopyrazol-4-carbonitrile;NSC 44932;(4-Cyano-1H-pyrazol-3-yl)amine;3-Amino-4-cyano-1H-pyrazole;5-Amino-1H-pyrazole-4-carbonitrile;5-Amino-4-cyano-1H-pyrazole;4-Cyano-3-aminopyrazole;95470-64-7;99196-22-2;103013-86-1;108443-29-4;134022-72-3;140706-29-2;40234-39-7;50908-45-7;52630-99-6;54381-61-2;72242-75-2;73075-19-1;80509-48-4;81375-80-6;89403-99-6;706823-00-9;749216-52-2;821023-66-9;842170-55-2;862172-63-2;875554-86-2;877833-74-4;145370-88-3;147770-51-2;154180-57-1;159224-07-4;250712-20-0;882231-01-8;924366-17-6;948292-33-9;1017683-96-3;1028842-84-3;1092789-12-2
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Description

Tan Crystalline Solid

3-Amino-4-cyanopyrazole Basic Attributes

Molecular Weight：

108.1

Exact Mass：

108.10

EC Number：

240-665-6

UNII：

OOB953S9X2

NSC Number：

44932

DSSTox ID：

DTXSID9066091

HScode：

29331990

Characteristics

PSA：

78.5

XLogP3：

0.1

Appearance：

Crystalline Solid

Density：

1.2722 (rough estimate)

Melting Point：

174-175 °C @ Solvent: Water

Boiling Point：

192.71°C (rough estimate)

Flash Point：

241.9±24.6 °C

Refractive Index：

1.7380 (estimate)

Storage Conditions：

Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

Vapor Pressure：

0mmHg at 25°C

Safety Information

Packing level：

III

Hazard category：

6.1

Transport codes：

3439

wgk germany：

hazard class code：

R20/21

safety instructions：

22-24/25-23-36-26

Marks：

Xn,T

Stability/Shelf Life：

Stable at room temperature in closed containers under normal storage and handling conditions.

Precautionary statement(s)：

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

Hazard Statements：

H301+H311+H331

GHS Classification：

|Warning|H302 (72.73%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 11 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

5-amino-4-cyanopyrazole

3-Amino-4-cyanopyrazole Use and Manufacturing

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).

Uses

3-Amino-4-pyrazolecarbonitrile has been a useful synthetic intermediate.

Manufacturing Info：

1H-Pyrazole-4-carbonitrile, 3-amino-: INACTIVE

Computed Properties

Molecular Weight:108.10
XLogP3:0.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Exact Mass:108.043596145
Monoisotopic Mass:108.043596145
Topological Polar Surface Area:78.5
Heavy Atom Count:8
Complexity:123
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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