ChemicalBook > CAS DataBase List > 1H-Pyrazole-3-carboxylic acid, 4-nitro-, methyl ester

1H-Pyrazole-3-carboxylic acid, 4-nitro-, methyl ester

Product Name: 1H-Pyrazole-3-carboxylic acid, 4-nitro-, methyl ester
CAS No.: 138786-86-4
Chemical Name: 1H-Pyrazole-3-carboxylic acid, 4-nitro-, methyl ester
Synonyms: 3-Methoxycarbonyl-4-nitropyrazole;Methyl 4-Nitropyrazole-3-carboxylate;Methyl 4-nitro-1H-pyrazol-3-carboxylate;methyl 4-nitro-4H-pyrazole-3-carboxylate;methyl 4-nitro-2H-pyrazole-3-carboxylate;4-Nitropyrazole-3-carboxylic acid methyl ester;4-Nitro-1H-pyrazole-3-carboxylic acid Methyl ester;1H-PYRAZOLE-5-CARBOXYLIC ACID 4-NITRO- METHYL ESTER;1H-Pyrazole-3-carboxylic acid, 4-nitro-, methyl ester;4-nitro-1H-Pyrazole-3-carboxylic acid methyl ester (9CI ACI)
CBNumber: CB61509207
Molecular Formula: C5H5N3O4
Formula Weight: 171.11
MOL File: 138786-86-4.mol

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1H-Pyrazole-3-carboxylic acid, 4-nitro-, methyl ester Property

Boiling point:: 363.2±22.0 °C(Predicted)
Density: 1.545
storage temp.: 2-8°C
pka: 6.67±0.50(Predicted)
form: solid
color: Off-white to light yellow
InChI: InChI=1S/C5H5N3O4/c1-12-5(9)4-3(8(10)11)2-6-7-4/h2H,1H3,(H,6,7)
InChIKey: ARAFBUCGMOKZMI-UHFFFAOYSA-N
SMILES: N1C=C([N+]([O-])=O)C(C(OC)=O)=N1

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Safety

HazardClass: IRRITANT
HS Code: 2933199090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

TRC

Product number: M339143
Product name: Methyl4-Nitro-1H-pyrazole-3-carboxylate
Packaging: 50mg
Price: $45
Updated: 2021/12/16

AK Scientific

Product number: J94817
Product name: Methyl4-nitro-1H-pyrazole-3-carboxylate
Packaging: 5g
Price: $45
Updated: 2021/12/16

Matrix Scientific

Product number: 113995
Product name: Methyl 4-nitro-1H-pyrazole-3-carboxylate
Purity: 97%
Packaging: 1g
Price: $15
Updated: 2021/12/16

AK Scientific

Product number: X0355
Product name: Methyl4-nitro-1H-pyrazole-3-carboxylate
Packaging: 1g
Price: $21
Updated: 2021/12/16

ChemScene

Product number: CS-W009019
Product name: 1H-Pyrazole-3-carboxylicacid,4-nitro-,methylester
Purity: 99.74%
Packaging: 10g
Price: $66
Updated: 2021/12/16

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1H-Pyrazole-3-carboxylic acid, 4-nitro-, methyl ester Chemical Properties,Usage,Production

Synthesis

67-56-1

5334-40-7

138786-86-4

4-Nitro-1H-pyrazole-3-carboxylic acid (1.117 kg, 7.11 mol, 1.0 equiv.) and methanol (8.950 L, 8.0 v/v) were added to a 20 L reactor equipped with a digital thermometer and a mechanical stirrer. The reaction mixture was cooled to 0-5 °C under nitrogen protection and thionyl chloride (0.581 L, 7.96 mol, 0.52 v/v) was slowly added dropwise over 180 min. After the dropwise addition, the reaction mixture was gradually warmed to 18-25 °C and stirred overnight. After confirming the completion of the reaction by 1H NMR (d6-DMSO), the reaction mixture was concentrated at 40-45 °C under reduced pressure. The residue was treated with toluene (3 x 2.250 L, 3 x 2 v/v) and concentrated under reduced pressure at the same temperature to afford methyl 4-nitro-1H-pyrazole-3-carboxylate as an off-white solid (1.210 kg, 99.5% yield). In another experiment, 4-nitro-1H-pyrazole-3-carboxylic acid (1.00 kg, 6.37 mol, 1.0 eq.) and methanol (8.00 L, 8.0 v/v) were added to a flanged flask fitted with a mechanical stirrer, condenser and thermometer. The suspension was cooled to 0-5 °C under nitrogen protection and thionyl chloride (0.52 L, 7.12 mol, 0.52 v/v) was slowly added at this temperature. The mixture was gradually warmed to 15-25 °C over 16-24 h and the completion of the reaction was confirmed by 1H NMR (d6-DMSO). The reaction mixture was concentrated under reduced pressure at 35-45 °C and the residue was treated with toluene (2.00 L, 2.0 v/v) and the solvent was removed under reduced pressure at the same temperature. This process was repeated twice to give the final methyl 4-nitro-1H-pyrazole-3-carboxylate as an off-white solid (1.071 kg, 98.3% yield). In a small-scale experiment, thionyl chloride (2.90 mL, 39.8 mmol) was slowly added to a methanol (100 mL) solution of 4-nitro-1H-pyrazole-3-carboxylic acid (5.68 g, 36.2 mmol) at room temperature and the mixture was stirred for 48 hours. Upon completion of the reaction, the mixture was concentrated under reduced pressure and residual water was removed by azeotropy with toluene to afford methyl 4-nitro-1H-pyrazole-3-carboxylate as a white solid.1H NMR (400 MHz, DMSO-d6) δ 14.4 (s, 1H), 8.9 (s, 1H), 3.9 (s, 3H). Finally, 4-nitro-1H-pyrazole-3-carboxylic acid (1.350 kg, 8.59 mol, 1.0 eq.) and methanol (10.80 L, 8.0 v/v) were added to a flanged flask fitted with a mechanical stirrer, condenser and thermometer. The suspension was cooled to 0-5 °C under nitrogen protection and thionyl chloride (0.702 L, 9.62 mol, 0.52 v/v) was slowly added at this temperature. The mixture was gradually warmed to 15-25 °C over 16-24 h and the completion of the reaction was confirmed by 1H NMR (d6-DMSO). The reaction mixture was concentrated under reduced pressure at 35-45 °C and the residue was treated with toluene (2.70 L, 2.0 v/v) and the solvent was removed under reduced pressure at the same temperature. This procedure was repeated twice to give methyl 4-nitro-1H-pyrazole-3-carboxylate as an off-white solid (1.467 kg, 99.8% yield).1H NMR (d6-DMSO) was consistent with the structure and no entrapped solvent was detected.

References

[1] Patent: US2009/156582, 2009, A1. Location in patent: Page/Page column 28
[2] Patent: EP1847531, 2007, A1. Location in patent: Page/Page column 40
[3] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 10, p. 979 - 984
[4] Patent: CN107652293, 2018, A. Location in patent: Paragraph 0099; 0100; 0101
[5] Patent: WO2006/77426, 2006, A2. Location in patent: Page/Page column 71-73; 96-97

1H-Pyrazole-3-carboxylic acid, 4-nitro-, methyl ester Preparation Products And Raw materials

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View Lastest Price from 1H-Pyrazole-3-carboxylic acid, 4-nitro-, methyl ester manufacturers

Honest Joy Holdings Limited

Product: Methyl 4-nitro-1h-pyrazole-3-carboxylate 138786-86-4
Price: US $0.00/KG
Min. Order: 1KG
Purity: 98.2%
Supply Ability: 100 tons
Release date: 2022-01-26

Career Henan Chemical Co

Product: 1H-Pyrazole-3-carboxylic acid, 4-nitro-, methyl ester 138786-86-4
Price: US $1.00/kg
Min. Order: 1kg
Purity: 98%
Supply Ability: 200KG
Release date: 2018-12-23

138786-86-4, 1H-Pyrazole-3-carboxylic acid, 4-nitro-, methyl esterRelated Search:

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4-Nitro-1H-pyrazole-3-carboxylic acid Methyl ester

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1H-PYRAZOLE-5-CARBOXYLIC ACID 4-NITRO- METHYL ESTER

Methyl 4-Nitropyrazole-3-carboxylate

methyl 4-nitro-2H-pyrazole-3-carboxylate

methyl 4-nitro-4H-pyrazole-3-carboxylate

1H-Pyrazole-3-carboxylic acid, 4-nitro-, methyl ester (9CI, ACI)

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Methyl 4-nitro-1H-pyrazol-3-carboxylate

138786-86-4