[ CAS No. 55864-87-4 ]

Name: Ethyl 4-nitro-1H-pyrazole-3-carboxylate
Brand: Ambeed
SKU: A232918
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COA GC NMR CNMR HPLC/UPLC LC-MS SDS

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Product Details of [ 55864-87-4 ]

CAS No. :	55864-87-4	MDL No. :	MFCD00195040
Formula :	C₆H₇N₃O₄	Boiling Point :	365°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	-
M.W :	185.14	Pubchem ID :	338416
Synonyms :

Computed Properties of [ 55864-87-4 ]

TPSA :Topological Polar Surface Area	-	H-Bond Acceptor Count :	-
XLogP3 :	-	H-Bond Donor Count :	-
SP3 :	-	Rotatable Bond Count :	-

Safety of [ 55864-87-4 ]

Signal Word:	Warning	Class	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 55864-87-4 ]

Upstream synthesis route of [ 55864-87-4 ]
Downstream synthetic route of [ 55864-87-4 ]

[ 55864-87-4 ] Synthesis Path-Upstream 1~3

1
[ 64-17-5 ]
[ 5334-40-7 ]
[ 55864-87-4 ]

Yield	Reaction Conditions	Operation in experiment
98%	Reflux	A solution of 4-nitro-1H-pyrazole-3-carboxylic acid (2.5 g, 15.9 mmol) in ethanolic HCl (38.3 mL, 1.25M) was refluxed overnight. All volatiles were removed to yield a whitesolid (2.9 g, 98percent) which was used without any further purification. MS: M=186.1 (M+H)⁺
98%	Reflux; Inert atmosphere	A solution of 4-nitro-lH-pyrazole-3-carboxylic acid (2.5 g, 15.9 mmol) in ethanolic HQ (38.3 mL, 1.25M) was refluxed overnight. All volatiles were removed to yield a white solid (2.9 g, 98 percent) which was used without any further purification.MS: M = 186.1 (M+H)⁺
96%	at 20℃; for 48.00 h;	Thionyl chloride (2.90 ml, 39.8 mmol) was slowly added to a mixture of 4-nitro-3- pyrazolecarboxylic acid (5.68 g, 36.2 mmol) in EtOH (100 ml) at ambient temperature and the mixture stirred for 48 h. The mixture was reduced in vacuo and EPO <DP n="124"/>dried through azeotrope with toluene to afford 4-nitro-lH-pyrazole-3-carboxylic acid ethyl ester as a white solid (6.42 g, 96percent). (¹H NMR (400 MHz, DMSOd₆) δ 14.4 (s, IH), 9.0 (S₅ IH)₃ 4.4 (q, 2H), 1.3 (t, 3H)).

96%	at 20℃; for 48.00 h;	1A. 4-Nitro-lH-pyrazole-3-carboxylic acid ethyl ester; OEtN-NHThionyl chloride (2.90 ml, 39.8 mmol) was slowly added to a mixture of 4-nitro-3-pyrazolecarboxylic acid (5.68 g, 36.2 mmol) in EtOH (100 ml) at ambienttemperature and the mixture stirred for 48 h. The mixture was reduced in vacuaand dried through azeotrope with toluene to afford 4-nitro-lH-pyrazole-3-carboxylic acid ethyl ester as a white solid (6.42 g, 96percent). (*H NMR (400 MHz,DMSO-d₆) 8 14.4 (s, 1H), 9.0 (s, 1H), 4.4 (q, 2H), 1.3 (t, 3H)).
96%	at 20℃; for 48.00 h;	Preparation VIII; Synthesis of 4-ammo-1H-pyrazole-3-carboxylic acid ethyl esterStep 1. 4-Nitro-1H-pyrazole-3-carboxylic acid ethyl esterThionyl chloride (2.90 ml, 39.8 mmol) was slowly added to a mixture of 4-nitro-3- pyrazolecarboxylic acid (5.68 g, 36.2 mmol) in EtOH (100 ml) at ambient temperature and the mixture stirred for 48 hours. The mixture was reduced in vacuo and dried through azeotrope with toluene to afford 4-nitro-1H-pyrazole-3- carboxylic acid ethyl ester as a white solid (6.42 g, 96percent). (¹H NMR (400 MHz, DMSO-d₆) δ 14.4 (s, IH), 9.0 (s, IH), 4.4 (q, 2H), 1.3 (t, 3H)).
96%	at 20℃; for 48.00 h;	Thionyl chloride (2.90 ml, 39.8 mmol) was slowly added to a mixture of 4-nitro-3-pyrazolecarboxylic acid (5.68 g, 36.2 mmol) in EtOH (100 ml) at ambient temperature and the mixture stirred for 48 h. The mixture was reduced in vacuo and dried through azeotrope with toluene to afford 4-nitro-1H-pyrazole-3-carboxylic acid ethyl ester as a white solid (6.42 g, 96percent). (¹H NMR (400 MHz, DMSO-d₆) D 14.4 (s, 1 H), 9.0 (s, 1 H), 4.4 (q, 2H), 1.3 (t, 3H)).
96%	at 20℃; for 48.00 h;	Thionyl chloride (2.90 ml, 39.8 mmol) was slowly added to a mixture of 4-nitro-3-pyrazolecarboxylic acid (5.68 g, 36.2 mmol) in EtOH (100 ml) at ambient temperature and the mixture stirred for 48 h. The mixture was reduced in vacuo and dried through azeotrope with toluene to afford 4-nitro-1H-pyrazole-3-carboxylic acid ethyl ester as a white solid (6.42 g, 96percent). (¹H NMR (400 MHz, DMSO-d₆) D 14.4 (s, 1 H), 9.0 (s, 1 H), 4.4 (q, 2H), 1.3 (t, 3H)).
96%	at 20℃; for 48.00 h;	Step 1. 4-Nitro-lH-pyrazole-3-carboxylic acid ethyl ester; Thionyl chloride (2.90 ml, 39.8 mmol) was slowly added to a mixture of 4-nitro-3- pyrazolecarboxylic acid (5.68 g, 36.2 mmol) in EtOH (100 ml) at ambient temperature and the mixture stirred for 48 hours. The mixture was reduced in vacuo and dried through azeotrope with toluene to afford 4-nitro-lH-pyrazole-3- carboxylic acid ethyl ester as a white solid (6.42 g, 96percent). (¹H NMR (400 MHz, DMSO-d₆) δ 14.4 (s, IH), 9.0 (s, IH), 4.4 (q, 2H), 1.3 (t, 3H)).

Reference： [1] Patent: US2011/306589, 2011, A1. Location in patent: Page/Page column 45
[2] Patent: WO2011/154327, 2011, A1. Location in patent: Page/Page column 118
[3] Patent: WO2006/70198, 2006, A1. Location in patent: Page/Page column 122-123
[4] Patent: WO2006/3440, 2006, A1. Location in patent: Page/Page column 147
[5] Patent: WO2006/77414, 2006, A1. Location in patent: Page/Page column 142
[6] Patent: WO2006/77424, 2006, A1. Location in patent: Page/Page column 186
[7] Patent: WO2006/77425, 2006, A1. Location in patent: Page/Page column 186
[8] Patent: WO2006/77428, 2006, A1. Location in patent: Page/Page column 163
[9] Patent: WO2008/7123, 2008, A2. Location in patent: Page/Page column 111
[10] Journal of Medicinal Chemistry, 2008, vol. 51, # 16, p. 4986 - 4999
[11] Patent: WO2005/37797, 2005, A1. Location in patent: Page/Page column 271-272

2
[ 5334-40-7 ]
[ 55864-87-4 ]

Yield	Reaction Conditions	Operation in experiment
96%	With thionyl chloride In ethanol at 20℃; for 48.00 h;	Thionyl chloride (2.90 ml, 39.8 mmol) was slowly added to a mixture of 4-nitro-3- pyrazolecarboxylic acid (5.68 g, 36.2 mmol) in EtOH (100 ml) at ambient temperature and the mixture stirred for 48 h. The mixture was reduced in vacuo and dried through azeotrope with toluene to afford 4-nitro-1H-pyrazole-3-carboxylic acid ethyl ester as a white solid (6.42 g, 96percent). (¹H NMR (400 MHz, DMSO-d₆) δ 14.4 (s, 1H), 9.0 (s, 1H), 4.4 (q, 2H), 1.3 (t, 3H)).

Reference： [1] Patent: WO2005/12256, 2005, A1. Location in patent: Page/Page column 184
[2] Patent: WO2007/23105, 2007, A1. Location in patent: Page/Page column 63-64

3
[ 75-36-5 ]
[ 5334-40-7 ]
[ 55864-87-4 ]

Reference： [1] Patent: US2005/197340, 2005, A1. Location in patent: Page/Page column 68

[ 55864-87-4 ] Synthesis Path-Downstream 1~10

1
[ 55864-87-4 ]
[ 106-96-7 ]
[ 503821-47-4 ]

Reference： [1]Archiv der Pharmazie,2002,vol. 335,p. 339 - 346
[2]Medicinal Chemistry Research,2002,vol. 11,p. 333 - 344

2
[ 110-87-2 ]
[ 55864-87-4 ]
C₁₁H₁₅N₃O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88.4%	With toluene-4-sulfonic acid; In tetrahydrofuran; at 80℃; for 16h;	To a mixture of A32 (5.45 g, 29.4 mmol, 1 eq) and 3,4-dihydro-2H-pyran (7.43 g, 88.3 mmol, 8.07 mL, 3 eq) in THE (40 mL) was added TsOH (507 mg, 2.94 mmol, 0.1 eq). The resulting mixture was stirred at 80 C for 16 hours to give a yellow solution. TLC (PE/EtOAc = 3/1) showed the reaction was completed. The reaction mixture was quenched with H20 (100 mL) and extracted with EtOAc (50 mL x 2). The organic layer were washed with brine (20 mL x 3), dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to give a residue. The residue was purified by silica gel column chromatography (Si02, PE/EtOAc = 3:1) to give 7.01 g (yield: 88.4%) of A37 as a yellow oil.

Reference： [1]Patent: WO2019/229251,2019,A1.Location in patent: Page/Page column 66

3
[ 55864-87-4 ]
C₁₁H₁₆F₃N₃O₂ [ No CAS ]