5-Amino-3-methyl-1-phenylpyrazole Chemical Properties

Melting point:

114-117 °C (lit.)

Boiling point:

333 °C

Density 

1.2894 (rough estimate)

vapor pressure 

0.006Pa at 25℃

refractive index 

1.6250 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

3.88±0.10(Predicted)

form 

Solid

color 

Yellow to pale brown

Water Solubility 

6.051g/L at 25℃

InChI

InChI=1S/C10H11N3/c1-8-7-10(11)13(12-8)9-5-3-2-4-6-9/h2-7H,11H2,1H3

InChIKey

FMKMKBLHMONXJM-UHFFFAOYSA-N

SMILES

N1(C2=CC=CC=C2)C(N)=CC(C)=N1

LogP

1.76

CAS DataBase Reference

1131-18-6(CAS DataBase Reference)

NIST Chemistry Reference

1H-Pyrazol-5-amine, 3-methyl-1-phenyl-(1131-18-6)

EPA Substance Registry System

1H-Pyrazol-5-amine, 3-methyl-1-phenyl- (1131-18-6)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36

WGK Germany 

3

RTECS 

UQ4990000

Hazard Note 

Harmful

TSCA 

Yes

HazardClass 

IRRITANT

HS Code 

29331990

Toxicity

mouse,LD50,oral,1300mg/kg (1300mg/kg),BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS",Personal Communication from LONZA Ltd., CH-4002, Basel, SwitzerlandVol. 03FEB1981,

MSDS

• Language:English Provider:SigmaAldrich

5-Amino-3-methyl-1-phenylpyrazole Usage And Synthesis

Uses

3-methyl-1-phenyl-1H-pyrazol-5-amine is a useful research chemical.

Chemical Properties

Yellow crystalline powder

Uses

5-Amino-3-methyl-1-phenylpyrazole may be used to synthesize:

• substituted pyrazoles
• pyrazolopyridine derivatives
• pyrazolo[3,4,-b]pyridines

General Description

5-Amino-3-methyl-1-phenylpyrazole is an aminopyrazole derivative. It reacts with 6-methyl-4-oxo-4H-[1]-benzopyran-3-carboxaldehyde to yield 5-(2-hydroxy-5-methylbenzoyl)-3-methyl-1-phenyl-1H-pyrazolo[3,4-b]pyridine and 2-methoxy-6-methyl-3-(3-methyl-1-phenylpyrazol-5-ylaminomethylene)chroman-4-one.

Flammability and Explosibility

Not classified

Synthesis

In a 2-5 mL microwave reaction tube equipped with a stirrer, 3-aminobut-2-enenenitrile (164 mg, 2 mmol) was mixed with 5 mL of 1 M hydrochloric acid solution and stirred until completely dissolved to make a 0.4 M solution of the feedstock. Subsequently, phenylhydrazine (216 mg, 2 mmol) was added to this solution. The reaction tube was sealed with an aluminum cap and placed in a microwave reactor and irradiated at 150 °C for 10 min at a 'very high' absorbance setting. After completion of the reaction, it was cooled to room temperature to obtain a non-homogeneous solution containing an orange precipitate. The pH was adjusted to alkaline with 10% sodium hydroxide solution and sonicated for 5 min to promote solid precipitate formation. The precipitate was collected by filtration, washed twice with deionized water and dried to obtain a light orange solid product (292 mg, 84% yield). For products that do not precipitate easily, the basic aqueous layer can be extracted three times with dichloromethane (DCM) to separate the product. The organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the target compound.

References

[1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 42, p. 7806 - 7810
[2] Tetrahedron Letters, 2019, vol. 60, # 1, p. 72 - 74
[3] Chemistry of Heterocyclic Compounds, 2018, vol. 54, # 1, p. 51 - 57
[4] Khim. Geterotsikl. Soedin., 2018, vol. 54, # 1, p. 51 - 57,7
[5] Journal of Organic Chemistry, 1993, vol. 58, # 22, p. 6155 - 6157

5-Amino-3-methyl-1-phenylpyrazole(1131-18-6)Related Product Information

• 3-Methylpyrazole
• PHENYL VALERATE
• Methyl acetate
• Methyltriphenylphosphonium bromide
• Methyl salicylate
• Tribenuron methyl
• Lithium bis(trimethylsilyl)amide
• Pirimiphos-methyl
• Trimethylphenylammonium chloride
• METSULFURON METHYL
• N-Ethylmethylamine
• N,N-Dimethyl-1,4-phenylenediamine
• Dichloromethylphenylsilane
• Kresoxim-methyl
• Thiophanate-methyl
• Tris(hydroxymethyl)aminomethane
• Methyl
• Parathion-methyl