31230-17-8

Basic information

• Product Name: 3-Amino-5-methylpyrazole
• Synonyms: TIMTEC-BB SBB004375;BUTTPARK 48\04-98;ART-CHEM-BB B016021;AMINO(3-)-5-METHYLPYRAZOLE;AKOS BBS-00004647;AKOS B016021;5-METHYL-2H-PYRAZOLE-3-YL AMINE;5-METHYL-2H-PYRAZOL-3-YL AMINE
• CAS NO: 31230-17-8
• Molecular Formula: C₄H₇N₃
• Molecular Weight: 97.12
• EINECS: -0
• Product Categories: Amines;Pyrazoles & Triazoles;Pyrazole;Heterocyclic Compounds;Bases & Related Reagents;Heterocycles;Nucleotides;Pyrazoles & Triazoles;Benzimidazoles
• Mol File: 31230-17-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 45-47 °C(lit.)
• Boiling Point: 213 °C14 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Light yellow to orange/Solid
• Density: 1.0548 (rough estimate)
• Vapor Pressure: 2.81E-05mmHg at 25°C
• Refractive Index: 1.5200 (estimate)
• Storage Temp.: -20?C Freezer
• Solubility: Soluble in Dichloromethane and Methanol.
• PKA: 15.84±0.10(Predicted)
• Sensitive: Air Sensitive
• Stability: Light Sensitive
• BRN: 1904
• CAS DataBase Reference: 3-Amino-5-methylpyrazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Amino-5-methylpyrazole(31230-17-8)
• EPA Substance Registry System: 3-Amino-5-methylpyrazole(31230-17-8)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 31230-17-8(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

Different sources of media describe the Uses of 31230-17-8 differently. You can refer to the following data:
1. 3-Amino-5-methyl-1H-pyrazole was employed as beta-sheet template to investigate its interaction with ferrocenoyl-dipeptides. It is also used in the synthesis of 4-aryl-3,7,7-trimethyl-2,4,6,7,8,9-hexahydropyrazolo[3,4-b]quinolin-5-ones. It can react with 4-Ethoxymethylene-2-phenyl-4H-oxazol-5-one to get N-(2-Methyl-7-oxo-4,7-dihydro-pyrazolo[1,5-a]pyrimidin-6-yl)-benzamide.
2. 3-Amino-5-methylpyrazole was employed as beta-sheet template to investigate its interaction with ferrocenoyl-dipeptides. It was also used in the synthesis of 4-aryl-3,7,7-trimethyl-2,4,6,7,8,9-hexahydropyrazolo[3,4-b]quinolin-5-ones.

General Description

Complexation of the amino- and carboxyl-protected tripeptide with 3-amino-5-methylpyrazole was studied by low-temperature NMR experiments in a freonic solvent.

InChI:InChI=1/C4H7N3/c1-3-2-4(5)7-6-3/h2H,1H3,(H3,5,6,7)

Upstream product

• 151449-93-3 2-methyl-5,7-diphenyl-6,7-dihydropyrazolo<1,5-a>pyrimidine 
• 118129-50-3 3-[amino(methylthio)methylene]-2,4-pentanedione 
• 5720-05-8 4-methylphenylboronic acid 
• 81542-52-1 C₄H₆IN₃ 
• 110580-44-4 4-Chloro-5-methyl-1H-pyrazol-3-ylamine 
• 1780-72-9 4-bromo-5-methyl-1H-pyrazol-3-amine 
• 108-98-5 thiophenol 

Downstream Products

• 98488-10-9 2,7-dimethyl-1,4-dihydropyrazolo[1,5-a]pyrimidin-4-one 
• 107625-17-2 2-methyl-5-phenylpyrazolo[1,5-a]pyrimidin-7(4H)-one 
• 99056-35-6 ethyl 4,7-dihydro-2-methyl-7-oxopyrazolo[1,5-a]pyrimidine-6-carboxylate 
• 160654-28-4 (Z)-5-Amino-1--3-methyl-1H-pyrazol 
• 160654-29-5 (Z)-5-Amino-1-(1-hydroximino-3-phenylpropyl)-3-methyl-1H-pyrazol 
• 151449-97-7 2-methyl-5,7-diphenylpyrazolo<1,5-a>pyrimidine 
• 174469-59-1 2,5-dimethyl-7-phenylpyrazolo<1,5-a>pyrimidine 
• 186956-64-9 2-methyl-7-phenylpyrazolo[1,5-a]pyrimidine 

Relevant articles and documents

The Suzuki-Miyaura Cross-Coupling Reaction of Halogenated Aminopyrazoles: Method Development, Scope, and Mechanism of Dehalogenation Side Reaction

The efficient Suzuki-Miyaura cross-coupling reaction of halogenated aminopyrazoles and their amides or ureas with a range of aryl, heteroaryl, and styryl boronic acids or esters has been developed. The method allowed incorporation of problematic substrates: aminopyrazoles bearing protected or unprotected pyrazole NH, as well as the free amino or N-amide group. Direct comparison of the chloro, bromo, and iodopyrazoles in the Suzuki-Miyaura reaction revealed that Br and Cl derivatives were superior to iodopyrazoles, as a result of reduced propensity to dehalogenation. Moreover, the mechanism and factors affecting the undesired dehalogenation side reaction were revealed.

Synthesis of 4-acetyl-5(3)-amino-3(5)-methylpyrazoles and pyrazolopyrimidines from diacetylketene N,S-acetal

Isomeric 4-acetyl-5-amino-3-methyl- and 4-acetyl-3-amino-5-methylpyrazoles (2, 3) were formed in the reaction of hydrazones with 3-pentan-2,4-dione (1) (diacetylketene N,S-acetal).Pyrazolopyrimidines (5a,b) were synthesized by condensation of 4-acetyl-5-amino-1,3-dimethylpyrazole (2a) with amide dimethylacetals followed by treatment with ammonium acetate.The structures of the compounds obtained were confirmed by 13C and 15N NMR spectroscopy. - Key words: diacetylketene N,S-acetal; hydrazines; 4-acetyl-5(3)-aminopyrazoles; amide acetals; pyrazolopyrimidines.