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Sigma-Aldrich

3-Aminopyrazole

98%

Synonym(s):

3-AP, 3-Pyrazolamine

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About This Item

Empirical Formula (Hill Notation):
C3H5N3
CAS Number:
1820-80-0
Molecular Weight:
83.09
Beilstein:
1618
EC Number:
217-338-1
MDL number:
MFCD00005236
UNSPSC Code:
12352100
PubChem Substance ID:
24849882
NACRES:
NA.22

Quality Level

100

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Synthesis and structure of some 3, 4-annelated coumarin systems.
Govori S, et al.
Heterocyclic Communications, 8(2), 129-134 (2002)
Tetrahedron Letters, 47, 2611-2611 (2006)
Trends Heterocycl. Chem., 2, 97-97 (1991)
The interaction of ferrocenoyl peptides with 3-aminopyrazole.
Saweczko P and Kraatz H-B.
Coordination Chemistry Reviews, 190, 185-198 (1999)
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