1-Methyl-1H-pyrazol-5-ylamine Chemical Properties

Melting point:

73 °C

Boiling point:

95-96°C (0.5 mmHg)

Density 

1.22±0.1 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

solubility 

Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

form 

Solid

pka

4.16±0.10(Predicted)

color 

Dark Red to Orange to Brown

InChI

InChI=1S/C4H7N3/c1-7-4(5)2-3-6-7/h2-3H,5H2,1H3

InChIKey

JESRNIJXVIFVOV-UHFFFAOYSA-N

SMILES

N1(C)C(N)=CC=N1

CAS DataBase Reference

1192-21-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38-22

Safety Statements 

26-36/37/39

RIDADR 

2811

HazardClass 

IRRITANT

HS Code 

29331990

1-Methyl-1H-pyrazol-5-ylamine Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

An interesting synthetic intermediate

Synthesis

General procedure for the synthesis of 1-methyl-5-aminopyrazole (9) from 3-methoxyacrylonitrile (1a) and methylhydrazine (2b): methylhydrazine (2b) (0.25 mL, 4.7 mmol) and 3-methoxyacrylonitrile (1a) (0.20 mL, 2.4 mmol) were dissolved in toluene/acetic acid (4:1 v/v; 5 mL) solvent mixture. The reaction mixture was placed in a sealed pressure rated Pyrex tube (10 mL) and microwave irradiated for 1 h at 120 °C using a CEM Discover microwave synthesizer set at an initial power of 100 W. The reaction was carried out using a CEM Discover microwave synthesizer. After completion of the reaction, the reaction mixture was cooled in a stream of compressed air. Subsequently, the reaction mixture was neutralized with saturated aqueous NaHCO3 solution and extracted with EtOAc (3 × 20 mL). The organic layers were combined, washed sequentially with water and brine, dried over MgSO4, and the solvent was evaporated in vacuum to afford 1-methyl-5-aminopyrazole (0.22 g, 97%) as a light brown solid with a melting point of 71-73 °C (literature value: 71-72 °C). The product was confirmed by high-resolution mass spectrometry (measured value: 97.0640, C4H7N3 [M] theoretical value: 97.0637).1H NMR (400 MHz; DMSO-d6) δ 7.60 (1H, d, J = 2.0 Hz, H-3), 5.15 (1H, d, J = 2.0 Hz, H-4), 3.85 (2H, br s, with D2O exchange, NH2), 3.50 (3H, s, Me); 13C NMR (126 MHz; DMSO-d6) δ 145.6 (C), 138.5 (CH), 90.8 (CH), 34.0 (Me); LRMS (APcI) m/z (relative intensity) 97 (M+, 100).

References

[1] Tetrahedron, 2013, vol. 69, # 39, p. 8429 - 8438

1-Methyl-1H-pyrazol-5-ylamine(1192-21-8)Related Product Information

• 5-AMINO-1-(4-CHLOROPHENYL)-1H-PYRAZOLE-4-CARBONITRILE
• 5-AMINO-4-CYANO-3-CYANOMETHYL-1-PHENYLPYRAZOLE
• 5-AMINO-1-PHENYLPYRAZOLE-4-CARBONITRILE
• 5-AMINO-4-CYANO-1-(2-HYDROXYETHYL)PYRAZOLE
• 1,3-Dimethyl-1H-pyrazol-5-amine
• 1,4,6-Trimethyl-1H-pyrazolo[3,4-b]pyridin-3-ylamine ,97%
• 5-Amino-3-methyl-1-phenylpyrazole
• 5-AMINO-1-PHENYLPYRAZOLE
• 5-AMINO-4-CARBETHOXY-1-PHENYLPYRAZOLE
• ETHYL 5-AMINO-1-METHYLPYRAZOLE-4-CARBOXYLATE
• 5-AMINO-1-PHENYLPYRAZOLE-4-CARBOXAMIDE
• 5-AMINO-3-METHYL-1H-PYRAZOLE-4-CARBOXYLIC ACID ETHYL ESTER
• 1-METHYL-1H-PYRAZOL-4-YLAMINE
• 1-METHYL-1H-PYRAZOL-3-YLAMINE
• 3-Amino-5-methylpyrazole
• 6-Methyl-1H-pyrazolo[3,4-b]pyridin-3-amine
• 1-(3'-Sulfo)phenyl-3-methyl-5-aminopyrazole
• 4,6-DIMETHYL-1H-PYRAZOLO[3,4-B]PYRIDIN-3-AMINE