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532223

Sigma-Aldrich

5-Amino-1,3-dimethylpyrazole

97%

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Empirical Formula (Hill Notation):
C5H9N3
CAS Number:
Molecular Weight:
111.15
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

mp

65-69 °C (lit.)

SMILES string

Cc1cc(N)n(C)n1

InChI

1S/C5H9N3/c1-4-3-5(6)8(2)7-4/h3H,6H2,1-2H3

InChI key

ZFDGMMZLXSFNFU-UHFFFAOYSA-N

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This Item
123048390836541001
5-Amino-1,3-dimethylpyrazole 97%

532223

5-Amino-1,3-dimethylpyrazole

5-Amino-1-pentanol ≥92.0% (GC)

123048

5-Amino-1-pentanol

2,4-Dimethylpyrrole 97%

390836

2,4-Dimethylpyrrole

5-Amino-3-methyl-1-phenylpyrazole 97%

541001

5-Amino-3-methyl-1-phenylpyrazole

mp

65-69 °C (lit.)

mp

33-35 °C (lit.)

mp

-

mp

114-117 °C (lit.)

General description

5-Amino-1,3-dimethylpyrazole undergoes cyclocondensation with ethyl acetoacetate to form the corresponding tetrahydropyrazolopyridine derivatives.

Application

5-Amino-1,3-dimethylpyrazole may be used in the preparation of:
  • 5-benzamido-1,3-dimethylpyrazole
  • diethyl 2-{[(1,3-dimethyl-1H-pyrazol-5-yl)amino]methylene}malonate
  • 5-amino-1,3-dimethyl-4-phthalidylpyrazole
  • (E)-N-(3,7-dimethylocta-2,6-dienyl)-1,3-dimethyl-1H-pyrazol-5-amine analog(LQFM002)
  • 4-isopropyl-1,3-dimethyl-1H-pyrazolo[3,4-b]pyridin-6-ol

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

190.4 °F - closed cup

flash_point_c

88 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves


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The reaction of o?phthalaldchydic acid with 5?amino?1,3?dimethylpyrazole.
Swett LR and Aynilian GH.
Journal of Heterocyclic Chemistry, 12(6), 1135-1136 (1975)
Hiroshi Ochiai et al.
Chemical & pharmaceutical bulletin, 52(9), 1098-1104 (2004-09-02)
A series of 4-anilinopyrazolopyridine derivatives were synthesized and biologically evaluated as inhibitors of phosphodiesterase (PDE4). Chemical modification of 3, a structurally new chemical lead that was found in our in-house library, was focused on 1- and 3-substituents. Full details of
The cyclocondensation of 5?amino?1,3?dimethylpyrazole with ethyl acetoacetate. Synthesis of isomeric pyrazolopyridones.
Ratajczyk JD and Swett LR.
Journal of Heterocyclic Chemistry, 12(3), 517-522 (1975)
1,3-Oxazines and related compounds. II.1) Ring contraction reaction of 1, 3-oxazin-4-one derivatives into 1,2,4-triazoles and pyrazoles.
Yamamoto, et al.
Chemical & Pharmaceutical Bulletin, 26(6), 1825-1831 (1978)
E A Costa et al.
Life sciences, 92(3), 237-244 (2013-01-09)
The current study describes the synthesis and pharmacological evaluation of (E)-N-(3,7-dimethylocta-2,6-dienyl)-1,3-dimethyl-1H-pyrazol-5-amine (LQFM002), a compound originally designed through a molecular simplification strategy from 4-nerolidylcatechol. LQFM002 was evaluated for preservation of the PLA(2) enzyme inhibitory effects of the lead compound, 4-nerolidylcatechol, using

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