4-Nitropyrazole-3-carboxylic acid supplier

Name
4-Nitropyrazole-3-carboxylic acid
EINECS
CAS No. 5334-40-7
Article Data5
CAS DataBase
Density 1.84 g/cm³
Solubility
Melting Point 195°C
Formula C₄H₃N₃O₄
Boiling Point 509.596 °C at 760 mmHg
Molecular Weight 157.086
Flash Point 261.995 °C
Transport Information
Appearance White to off-white crystalline powder
Safety 26-37/39
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 4-nitro pyrazole-3-carboxylic acid;Pyrazole-3(or5)-carboxylic acid, 4-nitro- (6CI);Pyrazole-3-carboxylic acid, 4-nitro- (8CI);4-Nitro-1H-pyrazol-3-carboxylic acid;4-Nitro-1H-pyrazole-3-carboxylic acid;4-Nitropyrazole-3-carboxylic acid;4-Nitropyrazole-5-carboxylic acid;NSC 1411;
PSA 111.80000
LogP 0.53930

Synthetic route

: 1453-58-3
3-Methylpyrazole

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

Conditions

Conditions	Yield
With sodium dichromate; sulfuric acid; nitric acid 1.) 100 deg C, 4 h, 2.) 60 deg C, 10 h; Yield given. Multistep reaction;

: 67-56-1
methanol

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 138786-86-4
methyl 4-nitro-1H-pyrazole-3-carboxylate

Conditions

Conditions	Yield
Stage #1: methanol; 4-nitro-1H-pyrazole-3-carboxylic acid With acetyl chloride at 20℃; for 16h; Stage #2: With water; sodium hydrogencarbonate In methanol; ethyl acetate pH=8 - 9; Product distribution / selectivity;	100%
Stage #1: methanol; 4-nitro-1H-pyrazole-3-carboxylic acid With acetyl chloride Stage #2: With sodium hydrogencarbonate In methanol; water; ethyl acetate pH=8 - 9;	100%
With thionyl chloride at 0 - 20℃;	100%

: 67-56-1
methanol

: 7719-09-7
thionyl chloride

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 138786-86-4
methyl 4-nitro-1H-pyrazole-3-carboxylate

Conditions

Conditions	Yield
at 0 - 25℃; for 16 - 48h; Product distribution / selectivity;	99.5%

...Expand

: 67-56-1
methanol

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 138786-86-4
4-nitro-2H-pyrazole-3-carboxylic acid methyl ester

Conditions

Conditions	Yield
With thionyl chloride at 0 - 20℃; for 16.5h;	99%
With thionyl chloride at 0 - 20℃;	82%
With thionyl chloride at 0 - 35℃;	82%

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 138786-86-4
methyl 4-nitro-1H-pyrazole-3-carboxylate

Conditions

Conditions	Yield
With thionyl chloride In methanol at 70℃; for 5h;	99%
With thionyl chloride In methanol; toluene
With thionyl chloride In methanol
With thionyl chloride In methanol; toluene
In methanol; toluene

: 64-17-5
ethanol

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 55864-87-4
4-nitro-1H-pyrazole-3-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With hydrogenchloride Reflux;	98%
With hydrogenchloride Reflux; Inert atmosphere;	98%
With thionyl chloride at 20℃; for 2h; Cooling with ice;	98%

: 371-40-4
4-fluoroaniline

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 844443-71-6
4-nitro-1H-pyrazole-3-carboxylic acid (4-fluorophenyl)amide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 16h;	97%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 2h;	82%
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 20℃;
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 20℃;
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In DMF (N,N-dimethyl-formamide) at 20℃;

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 55864-87-4
4-nitro-1H-pyrazole-3-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With thionyl chloride In ethanol at 20℃; for 48h;	96%
Stage #1: ethanol With acetyl chloride at 0 - 20℃; for 0.5h; Stage #2: 4-nitro-1H-pyrazole-3-carboxylic acid at 20℃; for 48h;

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 65190-36-5
4-nitro-1H-pyrazole-3-carboxamide

Conditions

Conditions	Yield
Stage #1: 4-nitro-1H-pyrazole-3-carboxylic acid With oxalyl dichloride In tetrahydrofuran at 25℃; for 0.5h; Stage #2: With ammonium hydroxide In tetrahydrofuran at 25℃; for 3h; Cooling with ice;	96%
Stage #1: 4-nitro-1H-pyrazole-3-carboxylic acid With thionyl chloride; N,N-dimethyl-formamide Stage #2: With ammonium hydroxide at 20℃;	57%

: 110-87-2
3,4-dihydro-2H-pyran

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 906087-80-7
4-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-3-carboxylic acid

Conditions

Conditions	Yield
With p-toluenesulfonic acid monohydrate In tetrahydrofuran at 20℃; for 16h;	95%
With toluene-4-sulfonic acid In tetrahydrofuran at 20℃;	95%
With toluene-4-sulfonic acid In tetrahydrofuran Inert atmosphere; Reflux;	93.2%

: 67-56-1
methanol

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 1166981-47-0
methyl 4-nitro-1H-pyrazole-3-carboxylate hydrochloride

Conditions

Conditions	Yield
With acetyl chloride	90%
With acetyl chloride at 0 - 20℃; for 24h;
With thionyl chloride at 20℃; Cooling with ice;

: 70261-82-4
4-[(4-methyl-1-piperazinyl)methyl]aniline

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 1308400-19-2
N-(4-((4-methylpiperazin-1-yl)methyl))phenyl-4-nitro-1H-pyrazole-3-carboxamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 24h;	88.2%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 24h;
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 24h;	11.1 g

: 95-54-5
1,2-diamino-benzene

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 825615-90-5
2-(4-nitro-1H-pyrazol-3-yl)-1H-benzoimidazole

Conditions

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine for 5h; Reflux; Inert atmosphere;	85%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 27h; Reflux;	69%
Stage #1: 1,2-diamino-benzene; 4-nitro-1H-pyrazole-3-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; Stage #2: With acetic acid Reflux;

: 87120-72-7
1-(tert-butoxycarbonyl)-4-aminopiperidine

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 844443-80-7
4-[(4-nitro-1H-pyrazole-3-carbonyl)amino]piperidine-1-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 16h;	84%
With 1-hydroxy-7-aza-benzotriazole; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 20℃;
With 1-hydroxy-7-aza-benzotriazole; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 20℃;

: 768-95-6
1-adamanthanol

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 1-(1-adamantyl)-3-carboxy-4-nitropyrazole

Conditions

Conditions	Yield
With phosphoric acid In acetic acid at 60℃; for 3h;	82%

: 57011-48-0
1,3-diazido 2-propanol

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 1,3-diazidopropan-2-yl 4-nitro-1H-pyrazole-3-carboxylate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Green chemistry;	78%

: 1453-58-3
3-Methylpyrazole

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

Conditions

Conditions	Yield
With sodium dichromate; sulfuric acid; nitric acid 1.) 100 deg C, 4 h, 2.) 60 deg C, 10 h; Yield given. Multistep reaction;

: 67-56-1
methanol

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 138786-86-4
methyl 4-nitro-1H-pyrazole-3-carboxylate

Conditions

Conditions	Yield
Stage #1: methanol; 4-nitro-1H-pyrazole-3-carboxylic acid With acetyl chloride at 20℃; for 16h; Stage #2: With water; sodium hydrogencarbonate In methanol; ethyl acetate pH=8 - 9; Product distribution / selectivity;	100%
Stage #1: methanol; 4-nitro-1H-pyrazole-3-carboxylic acid With acetyl chloride Stage #2: With sodium hydrogencarbonate In methanol; water; ethyl acetate pH=8 - 9;	100%
With thionyl chloride at 0 - 20℃;	100%

: 67-56-1
methanol

: 7719-09-7
thionyl chloride

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 138786-86-4
methyl 4-nitro-1H-pyrazole-3-carboxylate

Conditions

Conditions	Yield
at 0 - 25℃; for 16 - 48h; Product distribution / selectivity;	99.5%

...Expand

: 67-56-1
methanol

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 138786-86-4
4-nitro-2H-pyrazole-3-carboxylic acid methyl ester

Conditions

Conditions	Yield
With thionyl chloride at 0 - 20℃; for 16.5h;	99%
With thionyl chloride at 0 - 20℃;	82%
With thionyl chloride at 0 - 35℃;	82%

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 138786-86-4
methyl 4-nitro-1H-pyrazole-3-carboxylate

Conditions

Conditions	Yield
With thionyl chloride In methanol at 70℃; for 5h;	99%
With thionyl chloride In methanol; toluene
With thionyl chloride In methanol
With thionyl chloride In methanol; toluene
In methanol; toluene

: 64-17-5
ethanol

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 55864-87-4
4-nitro-1H-pyrazole-3-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With hydrogenchloride Reflux;	98%
With hydrogenchloride Reflux; Inert atmosphere;	98%
With thionyl chloride at 20℃; for 2h; Cooling with ice;	98%

: 371-40-4
4-fluoroaniline

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 844443-71-6
4-nitro-1H-pyrazole-3-carboxylic acid (4-fluorophenyl)amide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 16h;	97%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 2h;	82%
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 20℃;
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 20℃;
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In DMF (N,N-dimethyl-formamide) at 20℃;

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 55864-87-4
4-nitro-1H-pyrazole-3-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With thionyl chloride In ethanol at 20℃; for 48h;	96%
Stage #1: ethanol With acetyl chloride at 0 - 20℃; for 0.5h; Stage #2: 4-nitro-1H-pyrazole-3-carboxylic acid at 20℃; for 48h;

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 65190-36-5
4-nitro-1H-pyrazole-3-carboxamide

Conditions

Conditions	Yield
Stage #1: 4-nitro-1H-pyrazole-3-carboxylic acid With oxalyl dichloride In tetrahydrofuran at 25℃; for 0.5h; Stage #2: With ammonium hydroxide In tetrahydrofuran at 25℃; for 3h; Cooling with ice;	96%
Stage #1: 4-nitro-1H-pyrazole-3-carboxylic acid With thionyl chloride; N,N-dimethyl-formamide Stage #2: With ammonium hydroxide at 20℃;	57%

: 110-87-2
3,4-dihydro-2H-pyran

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 906087-80-7
4-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-3-carboxylic acid

Conditions

Conditions	Yield
With p-toluenesulfonic acid monohydrate In tetrahydrofuran at 20℃; for 16h;	95%
With toluene-4-sulfonic acid In tetrahydrofuran at 20℃;	95%
With toluene-4-sulfonic acid In tetrahydrofuran Inert atmosphere; Reflux;	93.2%

: 67-56-1
methanol

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 1166981-47-0
methyl 4-nitro-1H-pyrazole-3-carboxylate hydrochloride

Conditions

Conditions	Yield
With acetyl chloride	90%
With acetyl chloride at 0 - 20℃; for 24h;
With thionyl chloride at 20℃; Cooling with ice;

: 70261-82-4
4-[(4-methyl-1-piperazinyl)methyl]aniline

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 1308400-19-2
N-(4-((4-methylpiperazin-1-yl)methyl))phenyl-4-nitro-1H-pyrazole-3-carboxamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 24h;	88.2%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 24h;
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 24h;	11.1 g

: 95-54-5
1,2-diamino-benzene

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 825615-90-5
2-(4-nitro-1H-pyrazol-3-yl)-1H-benzoimidazole

Conditions

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine for 5h; Reflux; Inert atmosphere;	85%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 27h; Reflux;	69%
Stage #1: 1,2-diamino-benzene; 4-nitro-1H-pyrazole-3-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; Stage #2: With acetic acid Reflux;

: 87120-72-7
1-(tert-butoxycarbonyl)-4-aminopiperidine

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 844443-80-7
4-[(4-nitro-1H-pyrazole-3-carbonyl)amino]piperidine-1-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 16h;	84%
With 1-hydroxy-7-aza-benzotriazole; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 20℃;
With 1-hydroxy-7-aza-benzotriazole; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 20℃;

: 768-95-6
1-adamanthanol

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 1-(1-adamantyl)-3-carboxy-4-nitropyrazole

Conditions

Conditions	Yield
With phosphoric acid In acetic acid at 60℃; for 3h;	82%

: 57011-48-0
1,3-diazido 2-propanol

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 1,3-diazidopropan-2-yl 4-nitro-1H-pyrazole-3-carboxylate

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Green chemistry;	78%

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 304897-49-2
4-(4-tert-butoxycarbonyl-piperazino-methyl)-aniline

: C20H26N6O5

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 12h;	76%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 24h;

: 67-56-1
methanol

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 74-88-4
methyl iodide

: 400877-57-8
1-methyl-4-nitro-1H-pyrazole-3-carboxylic acid methyl ester

Conditions

Conditions	Yield
Stage #1: methanol; 4-nitro-1H-pyrazole-3-carboxylic acid With thionyl chloride at 0 - 20℃; Stage #2: methyl iodide With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃;	75%

...Expand

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 116008-52-7
4-amino-1H-pyrazole-3-carboxylic acid

Conditions

Conditions	Yield
With iron(III) chloride hexahydrate; pyrographite; hydrazine hydrate In water for 30h; Reflux;	75%

: 75-31-0
isopropylamine

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 906087-45-4
N-isopropyl-4-nitro-1H-pyrazole-3-carboxamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 16h;	70%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 16h;	70%

: 6232-11-7
methyl 4-(aminomethyl)benzoate hydrochloride

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: methyl 4-((4-nitro-1H-pyrazole-3-carboxamido)methyl)benzoate

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 12h;	65%

: C12H17N3O

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: C16H16N6O3

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃;	63%

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 36805-97-7
N,N-dimethylformamide di-tert-butyl acetal

: tert-butyl 4-nitro-1H-pyrazole-3-carboxylate

Conditions

Conditions	Yield
at 100℃; for 12h; Inert atmosphere;	63%

: 121588-79-2
methoxycyclohexanamine hydrochloride

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: N-((1r,4r)-4-methoxycyclohexyl)-4-nitro-1H-pyrazole-3-carboxamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 16h; Inert atmosphere;	62%

: 825619-02-1
4-morpholin-4-ylmethylbenzene-1,2-diamine

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 825619-29-2
4-((2-(4-nitro-1H-pyrazol-3-yl)-1H-benzo[d]imidazole-5-yl)methyl)morpholine

Conditions

Conditions	Yield
Stage #1: 4-morpholin-4-ylmethylbenzene-1,2-diamine; 4-nitro-1H-pyrazole-3-carboxylic acid With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide at 20℃; for 24h; Stage #2: With acetic acid for 3h; Product distribution / selectivity; Heating / reflux;	61%
Stage #1: 4-morpholin-4-ylmethylbenzene-1,2-diamine; 4-nitro-1H-pyrazole-3-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 24h; Stage #2: With acetic acid for 3h; Reflux;	61%
Stage #1: 4-morpholin-4-ylmethylbenzene-1,2-diamine; 4-nitro-1H-pyrazole-3-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 24h; Stage #2: With acetic acid for 3h; Product distribution / selectivity; Heating / reflux;	61%

: 137-07-5
2-amino-benzenethiol

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 1607441-38-2
2-(4-nitro-1H-pyrazol-3-yl)-benzothiazole

Conditions

Conditions	Yield
Stage #1: 4-nitro-1H-pyrazole-3-carboxylic acid With oxalyl dichloride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 2-amino-benzenethiol In tetrahydrofuran; N,N-dimethyl-formamide at 100℃; for 1h;	61%
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine for 5h; Reflux; Inert atmosphere;

: 1254229-47-4
4-[(diethylamino)methyl]benzene-1,2-diamine

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 1254229-50-9
N-ethyl-N-{[2-(4-nitro-1H-pyrazol-3-yl)-1H-benzo[d]imidazol-5-yl]methyl}ethanamine

Conditions

Conditions	Yield
Stage #1: 4-[(diethylamino)methyl]benzene-1,2-diamine; 4-nitro-1H-pyrazole-3-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 24h; Stage #2: With acetic acid for 3h; Reflux;	57.8%

: 496-72-0
4-methyl-1,2-diaminobenzene

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 1254229-49-6
5-methyl-2-(4-nitro-1H-pyrazol-3-yl)-1H-benzo[d]imidazole

Conditions

Conditions	Yield
Stage #1: 4-methyl-1,2-diaminobenzene; 4-nitro-1H-pyrazole-3-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 24h; Stage #2: With acetic acid for 3h; Reflux;	57.3%

: 67-56-1
methanol

: 824-94-2
p-methoxybenzyl chloride

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 896467-74-6
methyl 1-(4-methoxybenzyl)-4-nitro-1H-pyrazole-3-carboxylate

Conditions

Conditions	Yield
Stage #1: methanol; 4-nitro-1H-pyrazole-3-carboxylic acid With thionyl chloride Stage #2: p-methoxybenzyl chloride With potassium carbonate In acetonitrile	56%

...Expand

: 4-(((4aR,7aR)-tetrahydro-2H-[1,4]dioxino[2,3-c]pyrrol-6(3H)-yl)methyl)benzene-1,2-diamine

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: (4aR,7aR)-6-((2-(4-nitro-1H-pyrazol-3-yl)-1H-benzo[d]imidazol-5-yl)methyl)hexahydro-2H-[1,4] dioxino[2,3-c]pyrrole

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 20℃;	54%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 20℃;

: 100-39-0
benzyl bromide

: 5334-40-7
4-nitro-1H-pyrazole-3-carboxylic acid

: 1355011-61-8
benzyl 1-benzyl-4-nitro-1H-pyrazole-3-carboxylate

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 1.5h;	51%

4-Nitropyrazole-3-carboxylic acid Chemical Properties

IUPAC Name: 4-Nitro-1H-pyrazole-5-carboxylic acid
Systematic of 1H-Pyrazole-3-carboxylicacid, 4-nitro- (CAS NO.5334-40-7): Akos b000132 ; 4-Nitro-1h-pyrazole-3-carboxylic acid ; 4-Nitro-1h-pyrazol-3-ylcarboxylic acid ; 4-Nitro-3-pyrazolecarboxylic acid ; 4-Nitropyrazole-3-carboxylic acid ; Timtec-bb sbb001727 ; 3-Carboxy-4-nitro-1H-pyrazole
CAS NO: 5334-40-7
Molecular Formula of 1H-Pyrazole-3-carboxylicacid, 4-nitro- (CAS NO.5334-40-7): C₄H₃N₃O₄
Molecular Weight: 157.0843
Molecular Structure:

Melting Point: 195°C
H bond acceptors: 7
H bond donors: 2
Freely Rotating Bonds: 2
Polar Surface Area: 89.94 Å²
Index of Refraction: 1.679
Molar Refractivity: 32.25 cm³
Molar Volume: 85.3 cm³
Surface Tension: 113.5 dyne/cm
Density of 1H-Pyrazole-3-carboxylicacid, 4-nitro- (CAS NO.5334-40-7): 1.84 g/cm³
Flash Point: 262 °C
Enthalpy of Vaporization: 82.15 kJ/mol
Boiling Point: 509.6 °C at 760 mmHg
Vapour Pressure: 3.3E-11 mmHg at 25°C

4-Nitropyrazole-3-carboxylic acid Safety Profile

Hazard Codes: Irritant Xi
Risk Statements: 20/21/22-36/37/38
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 22-36/37/39-26
S22: Do not breathe dust.
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
HazardClass: IRRITANT

Product Name

4-Nitropyrazole-3-carboxylic acid

Synthetic route

4-Nitropyrazole-3-carboxylic acid Chemical Properties

4-Nitropyrazole-3-carboxylic acid Safety Profile

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