methyl (4-nitro-1H-pyrazol-1-yl)acetate

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CAS:6715-84-0
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methyl (4-nitro-1H-pyrazol-1-yl)acetate Basic information
Product Name:methyl (4-nitro-1H-pyrazol-1-yl)acetate
Synonyms:methyl (4-nitro-1H-pyrazol-1-yl)acetate;Methyl 4-Nitro-1H-pyrazole-1-acetate;methyl 2-(4-nitropyrazol-1-yl)acetate;1H-Pyrazole-1-acetic acid, 4-nitro-, methyl ester
CAS:6715-84-0
MF:C6H7N3O4
MW:185.14
EINECS:
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Mol File:6715-84-0.mol
methyl (4-nitro-1H-pyrazol-1-yl)acetate Structure
methyl (4-nitro-1H-pyrazol-1-yl)acetate Chemical Properties
Boiling point 321.7±22.0 °C(Predicted)
density 1.48±0.1 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
pka-2.71±0.10(Predicted)
AppearanceWhite to off-white Solid
InChIInChI=1S/C6H7N3O4/c1-13-6(10)4-8-3-5(2-7-8)9(11)12/h2-3H,4H2,1H3
InChIKeyGEADOFDFVOSIOA-UHFFFAOYSA-N
SMILESN1(CC(OC)=O)C=C([N+]([O-])=O)C=N1
Safety Information
MSDS Information
methyl (4-nitro-1H-pyrazol-1-yl)acetate Usage And Synthesis
UsesMethyl (4-Nitro-1H-pyrazol-1-yl)acetate is used in preparation of novel substituted glycine derivatives as Factor XIa and/or plasma kallikrein inhibitors.
Synthesis
4-Nitropyrazole

2075-46-9

Methyl chloroacetate

96-34-4

methyl (4-nitro-1H-pyrazol-1-yl)acetate

6715-84-0

Step 1: To a solution of 4-nitro-1H-pyrazole (100 g, 0.88 mol) in acetonitrile (ACN, 2 L) was added potassium carbonate (K2CO3, 183.2 g, 1.33 mol) and methyl chloroacetate (95.6 g, 0.88 mol). The reaction mixture was heated to 60 °C and the reaction was stirred at this temperature for 5 hours. Upon completion of the reaction, the mixture was filtered to remove insoluble solids and the solvent was subsequently removed by distillation under reduced pressure to afford methyl 2-(4-nitro-1H-pyrazol-1-yl)acetate as a white solid (150 g, 92% yield). The product was characterized by 1H NMR (400 MHz, CDCl3): δ 8.28 (s, 1H), 8.11 (s, 1H), 4.98 (s, 2H), 3.84 (s, 3H).

References[1] Patent: WO2013/14162, 2013, A1. Location in patent: Page/Page column 99
methyl (4-nitro-1H-pyrazol-1-yl)acetate Preparation Products And Raw materials
Raw materials4-Nitropyrazole-->Methyl chloroacetate-->Potassium carbonate-->Acetonitrile
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