Production Method 1

17900-68-4

947-95-5

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride

Reference

Aminomethylene derivatives of azoles. V. Reaction of aminomethylene derivatives with phosphorus oxychloride

Kvitko, I. Ya.; Porai-Koshits, B. A., Zhurnal Obshchei Khimii, 1966, 2(1), 169-73

Production Method 2

17364-41-9

947-95-5

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride Solvents: Dimethyl carbonate

Reference

Halogenation in carbonate diester solvents

, Japan, , ,

Production Method 3

141-97-9

947-95-5

Reaction Conditions

1.1 Solvents: Methanol ;  3 h, reflux
1.2 Reagents: Phosphorus oxychloride ;  1 h, 90 °C

Reference

Synthesis and antifungal activity of 2-heterocyclylbenzimidazole derivatives

Chen, Lan; Wei, Ningning; Gao, Jie; Zhou, Wenming, Nongyaoxue Xuebao, 2011, 13(5), 448-452

Production Method 4

947-95-5

Reaction Conditions

1.1 Catalysts: Aluminum chloride Solvents: Dichloromethane

Reference

A facile method for the preparation and cleavage of 1,1-diacetates of aldehydes

Sabitha, Gowravaram; Abraham, Sunny; Ramalingam, T.; Yadav, J. S., Journal of Chemical Research, 2002, (3), 144-146

Production Method 5

89-25-8

947-95-5

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride Solvents: Dimethylformamide ;  0 - 10 °C; 3 - 4 h, 90 - 100 °C

Reference

Synthesis and biological activities of novel 1,2,4-triazole thiones and bis(1,2,4-triazole thiones) containing phenylpyrazole and piperazine moieties

Wang, Bao-Lei; Zhang, Li-Yuan; Zhan, Yi-Zhou; Zhang, Yan; Zhang, Xiao; et al, Journal of Fluorine Chemistry, 2016, 184, 36-44

Production Method 6

942-32-5

947-95-5

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride ;  0 - 5 °C; 30 min, 0 - 5 °C
1.2 0 - 5 °C; 1 h, 5 - 120 °C

Reference

Design, synthesis, DFT study and antifungal activity of pyrazolecarboxamide derivatives

Mu, Jin-Xia; Shi, Yan-Xia; Yang, Ming-Yan; Sun, Zhao-Hui; Liu, Xing-Hai; et al, Molecules, 2016, 21(1),

Production Method 7

89-25-8

947-95-5

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride
1.2 Solvents: Dimethylformamide ;  cooled; 2 h, 80 - 85 °C
1.3 Reagents: Potassium carbonate Solvents: Water ;  neutralized, cooled

Reference

The tert-amino effect in heterocyclic chemistry: synthesis of new fused pyrazolinoquinolizine and 1,4-oxazinopyrazoline derivatives

Prajapati, Dipak; Borah, Kalyan Jyoti, Beilstein Journal of Organic Chemistry, 2007, 3,

Production Method 8

89-25-8

947-95-5

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride ;  0 °C
1.2 85 °C

Reference

New pyrazolyl-dibenzo[b,e][1,4]diazepinones: room temperature one-pot synthesis and biological evaluation

Brahmbhatt, Gaurangkumar C.; Sutariya, Tushar R.; Atara, Hiralben D.; Parmar, Narsidas J.; Gupta, Vivek K.; et al, Molecular Diversity, 2020, 24(2), 355-377

Production Method 9

1131-17-5

947-95-5

Reaction Conditions

1.1 Reagents: Trifluoroacetic acid ;  6 h, reflux
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  neutralized

Reference

Chemoselective and regiospecific formylation of 1-phenyl-1H-pyrazoles through the Duff reaction

de Oliveira, C. H. A.; Mairink, L. M.; Pazini, F.; Liao, L. M.; de Oliveira, A. L.; et al, Synthetic Communications, 2013, 43(12), 1633-1639

Production Method 10

89-25-8

947-95-5

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride

Reference

The Vilsmeier reaction of fully conjugated carbocycles and heterocycles

Jones, Gurnos; Stanforth, Stephen P., Organic Reactions (Hoboken, 1997, 49,

Production Method 11

89-25-8

947-95-5

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride

Reference

Syntheses of heterocyclic 2-(tert-butylthio)aldehydes

Becher, Jan; Olesen, Preben H.; Knudsen, Niels A.; Toftlund, Hans, Sulfur Letters, 1986, 4(5), 175-83

Production Method 12

89-25-8

947-95-5

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride ;  < 10 °C
1.2 10 °C → 90 °C; 1 h, 90 °C
1.3 Reagents: Water

Reference

Synthesis and biological activity of 4-(N-p-trifluoromethylphenyl) aminomethyl 5-substituted phenylthio pyrazole derivatives

Shi, Dabin; Xu, Yingshu; Liu, Jingzi; Ouyang, Guiping, Huaxue Tongbao, 2010, 73(12), 1139-1142

Production Method 13

89-25-8

947-95-5

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride Solvents: Dimethylformamide ;  0 °C; 2 h, 100 °C; 100 °C → rt
1.2 Solvents: Water ;  cooled

Reference

Discovery of Novel Pyrazolo[3,4-b]Pyridine Derivatives with Dual Activities of Vascular Remodeling Inhibition and Vasodilation for the Treatment of Pulmonary Arterial Hypertension

Hu, Liqing ; Li, Lijun; Chang, Qi; Fu, Songsen; Qin, Jia; et al, Journal of Medicinal Chemistry, 2020, 63(19), 11215-11234

Production Method 14

56694-49-6

947-95-5

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride Solvents: Dimethylformamide ;  0 - 5 °C; 30 min, 0 - 5 °C
1.2 1.5 h, 5 °C → 100 °C
1.3 Solvents: Water ;  cooled

Reference

Synthesis of Spirooxindole Analogs Tethered Pyrazole Scaffold as Acetylcholinesterase Inhibitors

Shahidul Islam, Mohammad; Al-Majid, Abdullah Mohammed; Azam, Mohammad; Prakash Verma, Ved; Barakat, Assem ; et al, ChemistrySelect, 2021, 6(48), 14039-14053

Production Method 15

89-25-8

947-95-5

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride Solvents: Dimethylformamide ;  0 - 5 °C; 30 min, 0 - 5 °C
1.2 2 h, 5 °C → 100 °C

Reference

Design, synthesis, and biological evaluation of amide imidazole derivatives as novel metabolic enzyme CYP26A1 inhibitors

Sun, Bin; Liu, Kai; Han, Jing; Zhao, Li-yu; Su, Xiao; et al, Bioorganic & Medicinal Chemistry, 2015, 23(20), 6763-6773

Production Method 16

89-25-8

947-95-5

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride ;  0 - 5 °C
1.2 0 - 5 °C; 1 h, 5 °C → reflux; cooled
1.3 Reagents: Water ;  0 °C

Reference

Preparation of imidazole amide derivatives for treating and/or preventing cancer and proliferative diseases

, China, , ,

Production Method 17

89-25-8

947-95-5

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride ;  0 - 5 °C; 30 min, 0 - 5 °C
1.2 1 h, 5 °C → 120 °C

Reference

Synthesis and biological evaluation of 3-phenyl-3-aryl carboxamido propanoic acid derivatives as small molecule inhibitors of retinoic acid 4-hydroxylase (CYP26A1)

Zhao, Dongmei; Sun, Bin; Ren, Jinhong; Li, Fengrong; Song, Shuai; et al, Bioorganic & Medicinal Chemistry, 2015, 23(6), 1356-1365

Production Method 18

89-25-8

947-95-5

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride ;  rt → 10 °C; 3 h, 10 °C → 90 °C; 90 °C → rt

Reference

Synthesis of pyrazole oxime esters

Xiao, Hui-quan; Ouyang, Gui-ping; Sun, Xu-dong; Yao, Xian-dong; Bao, Gao-qiang; et al, Hecheng Huaxue, 2005, 13(6), 600-602

Production Method 19

89-25-8

947-95-5

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride

Reference

Synthesis, Characterization, Antitubercular Activity, and Molecular Docking Studies of Pyrazolylpyrazoline-Clubbed Triazole and Tetrazole Hybrids

Zala, Mayursinh ; Vora, Jwalant J.; Khedkar, Vijay M., ACS Omega, 2023, 8(23), 20262-20271

Production Method 20

89-25-8

947-95-5

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride ;  1 h, 90 °C

Reference

Chemoselective Synthesis of 5-Alkylamino-1H-pyrazole-4-carbaldehydes by Cesium- and Copper-Mediated Amination

Orrego-Hernandez, Jessica; Cobo, Justo; Portilla, Jaime, European Journal of Organic Chemistry, 2015, 2015(23), 5064-5069

5-Chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde Raw materials

• Ethyl acetoacetate
• 3-Methyl-1-phenyl-1H-pyrazol-5-ol
• 3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazole-4-carbaldehyde
• 5-Chloro-3-methyl-1-phenylpyrazole
• Edaravone
• 3,4-Dimethyl-1-phenyl-1H-pyrazol-5(4H)-one
• 4H-Pyrazol-4-one, 1,5-dihydro-3-methyl-1-phenyl-

5-Chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde Preparation Products

• 5-Chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde (947-95-5)

• 1. Emerging investigators
  Polym. Chem., 2015,6, 5501-5502
• 2. Excimer–monomer switch: a reaction-based approach for selective detection of fluoride?
  Qiao Song,Angela Bamesberger,Lingyun Yang,Haley Houtwed,Haishi Cao Analyst, 2014,139, 3588-3592
• 3. Embedding heteroatoms: an effective approach to create porphyrin-based functional materials
  Norihito Fukui,Keisuke Fujimoto,Hideki Yorimitsu,Atsuhiro Osuka Dalton Trans., 2017,46, 13322-13341
• 4. Evolved polymerases facilitate selection of fully 2′-OMe-modified aptamers?
  Zhixia Liu,Tingjian Chen,Floyd E. Romesberg Chem. Sci., 2017,8, 8179-8182
• 5. Evolution of important glucosinolates in three common Brassica vegetables during their processing into vegetable powder and in vitro gastric digestion
  Nan Fu,Naphaporn Chiewchan,Xiao Dong Chen Food Funct., 2020,11, 211-220

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Azoles Phenylpyrazoles
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Azoles Pyrazoles Phenylpyrazoles

• 188047-58-7(1H-Pyrazole-4-carbonyl chloride, 5-chloro-3-methyl-1-phenyl-)
• 350997-70-5(5-Chloro-3-methyl-1-(4-methylphenyl)-1H-pyrazole-4-carbaldehyde)
• 370561-61-8(5-chloro-1-(2-chlorophenyl)-3-methyl-1H-pyrazole-4-carbaldehyde)
• 77509-93-4(5-chloro-1-(4-chlorophenyl)-3-methyl-1H-pyrazole-4-carbaldehyde)
• 62574-33-8(Methanone, (5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)phenyl-)
• 1140-38-1(5-Chloro-3-methyl-1-phenyl-1H-pyrazole-4-carboxylic acid)
• 377767-11-8(5-chloro-1-(4-fluorophenyl)-3-methyl-1H-pyrazole-4-carbaldehyde)
• 5499-67-2(5-chloro-1,3-diphenyl-1h-pyrazole-4-carbaldehyde)
• 176387-54-5(1H-Pyrazole-4-carboxaldehyde, 5-chloro-1-phenyl-3-propyl-)
• 139347-65-2(5-chloro-1-phenyl-3-(propan-2-yl)-1H-pyrazole-4-carbaldehyde)