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About This Item
Empirical Formula (Hill Notation):
C9H9N3
CAS Number:
Molecular Weight:
159.19
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Assay
98%
mp
124-127 °C (lit.)
functional group
phenyl
SMILES string
Nc1cc([nH]n1)-c2ccccc2
InChI
1S/C9H9N3/c10-9-6-8(11-12-9)7-4-2-1-3-5-7/h1-6H,(H3,10,11,12)
InChI key
PWSZRRFDVPMZGM-UHFFFAOYSA-N
General description
3-Amino-5-phenylpyrazole (3-phenyl-1H-pyrazol-5-amine), an amino pyrazole derivative, is an aza-heterocyclic amine.[1] It has been reported to be synthesized by heating either 3-amino-4-bromo- or 3-amino-5-phenylisothiazole in the presence of anhydrous hydrazine.[2] On reaction with ZnCl2 it affords chlorido-tris(3-amino-5-phenyl-1Hpyrazole-N2)zinc (II) chloride.[3]
Application
3-Amino-5-phenylpyrazole ((3-phenyl-1H-pyrazol-5-amine) may be used in the synthesis of the following:
- Urea derivatives by reaction with azido(6-(benzofuran-2-yl)-2-methylpyridin-3-yl) methanone.[4]
- 2-Mercaptoacetamide analogs by treating with thioglycolic acid.[5]
- 3-(Substituentpyrimidayl)-5,6-benzocoumarins by treating with 3-(2′-formyl-1′-chlorovinyl)-5,6-benzocoumarin.[6]
- Substituted 2,7-diphenylpyrazolo[1,5-a]pyrimidine-5-carboxylic esters by reacting with substituted β-diketo esters.[1]
- N-ethoxycarbonylthiourea derivative by reacting with ethoxycarbonyl isothiocyanate.[7]
- Heterobiaryl pyrazolo[3,4-b]pyridines by reacting with indole-3-carboxaldehyde.[8]
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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The conversion of isothiazoles into pyrazoles using hydrazine.
Ioannidou HA and Koutentis PA
Tetrahedron, 65(34), 7023-7037 (2009)
Crystal structure of chlorido-tris (3-amino-5-phenyl-1H pyrazole-N2) zinc (II) chloride, [ZnCl (C9H9N3)3] Cl.
Jacimovic ZK, et al
Zeitschrift fur Kristallographie, 226(3), 397-399 (2011)
Scott T Moe et al.
Bioorganic & medicinal chemistry, 17(8), 3072-3079 (2009-03-31)
Botulinum neurotoxin elicits its paralytic activity through a zinc-dependant metalloprotease that cleaves proteins involved in neurotransmitter release. Currently, no drugs are available to reverse the effects of botulinum intoxication. Herein we report the design of a novel series of mercaptoacetamide
Recent advances in the chemistry of ethoxycarbonyl isothiocyanate and related compounds.
George B and Papadopoulos EP
Journal of Heterocyclic Chemistry, 20(5), 1127-1142 (1983)
Syntheses of 3-pyrimidyl-and 3-pyranyl-5, 6-benzocoumarin derivatives.
El-Deen IM, et al
Bull. Korean Chem. Soc., 23(4), 610-612 (2002)
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