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Sigma-Aldrich

3-Aminopyrazole

98%

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Synonym(s):
3-AP, 3-Pyrazolamine
Empirical Formula (Hill Notation):
C3H5N3
CAS Number:
1820-80-0
Molecular Weight:
83.09
Beilstein:
1618
EC Number:
217-338-1
MDL number:
MFCD00005236
PubChem Substance ID:
24849882
NACRES:
NA.22

Assay

98%

form

solid

bp

218 °C/122 mmHg (lit.)

mp

34-37 °C (lit.)

SMILES string

Nc1cc[nH]n1

InChI

1S/C3H5N3/c4-3-1-2-5-6-3/h1-2H,(H3,4,5,6)

InChI key

JVVRJMXHNUAPHW-UHFFFAOYSA-N

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General description

3-Aminopyrazole is a heteroarylamine.

Application

3-Aminopyrazole was used in the spectroscopic characterization of ferrocenoyl peptides via 1H-NMR spectroscopy. It was also used in the synthesis of:
  • symmetrical dialkylpyrazolo[1,5-a]pyrimidines via condensation with symmetrical β-diketones
  • 3,4-annelated coumarins
  • heterocyclic compounds of pharmaceutical interest
  • pyrazolopyrimidines

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302 - H314

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B

Storage Class Code

8A - Combustible, corrosive hazardous materials

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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Trends Heterocycl. Chem., 2, 97-97 (1991)
Tetrahedron Letters, 47, 2611-2611 (2006)
The interaction of ferrocenoyl peptides with 3-aminopyrazole.
Saweczko P and Kraatz H-B.
Coordination Chemistry Reviews, 190, 185-198 (1999)
Synthesis and structure of some 3, 4-annelated coumarin systems.
Govori S, et al.
Heterocyclic Communications, 8(2), 129-134 (2002)
T Novinson et al.
Journal of medicinal chemistry, 18(5), 460-464 (1975-05-01)
A number of 3-bromo-, 3-nitro-, and 3-ethoxycarbonyl-5,7-dialkylpyrazolo[1,5-a]pyrimidines were synthesized and screened as in vitro cAMP phosphodiesterase inhibitors. The condensation of 3-aminopyrazole with symmetrical beta-diketones (acetylacetone, heptane-3,5-dione, etc.) afforded symmetrical dialkylpyrazolo[1,5-a]pyrimidines (5). The reaction of 3-aminopyrazole with unsymmetrical beta-diketones (hexane-2,4-dione, heptane-3,5-dione
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