3-(4-chloro-3-methylphenyl)-1H-pyrazole-5-carboxylic acid

Base Information

• Chemical Name: 3-(4-chloro-3-methylphenyl)-1H-pyrazole-5-carboxylic acid
• CAS No.: 113342-32-8
• Molecular Formula: C₁₁H₉ClN₂O₂
• Molecular Weight: 236.658
• DSSTox Substance ID: DTXSID30398189
• Wikidata: Q82200039
• Mol file: 113342-32-8.mol

Synonyms:113342-32-8;3-(4-chloro-3-methylphenyl)-1H-pyrazole-5-carboxylic acid;5-(4-CHLORO-3-METHYLPHENYL)-1H-PYRAZOLE-3-CARBOXYLIC ACID;SCHEMBL13883208;DTXSID30398189;D85321;EN300-1965710;1h-pyrazole-3-carboxylic acid,5-(4-chloro-3-methylphenyl)-

Chemical Property of 3-(4-chloro-3-methylphenyl)-1H-pyrazole-5-carboxylic acid

Chemical Property:

• XLogP3: 2.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 236.0352552
• Heavy Atom Count: 16
• Complexity: 275

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=CC(=C1)C2=NNC(=C2)C(=O)O)Cl

Technology Process of 3-(4-chloro-3-methylphenyl)-1H-pyrazole-5-carboxylic acid

There total 2 articles about 3-(4-chloro-3-methylphenyl)-1H-pyrazole-5-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

4-(4-chloro-3-methylphenyl)-2,4-dioxobutyric acid ethyl ester (475471-20-6) → 5-(4-chloro-3-methylphenyl)-1-H-pyrazole-3-carboxylic acid (113342-32-8)

Guidance literature:

4-(4-chloro-3-methylphenyl)-2,4-dioxobutyric acid ethyl ester; With hydrazine hydrate; In ethanol; for 1.5h; Heating;

With sodium hydroxide; In ethanol; for 1.5h; Heating;

DOI:10.1002/jlcr.952

Reference yield:

4-chloro-3-methylacetophenone (37074-39-8) → 5-(4-chloro-3-methylphenyl)-1-H-pyrazole-3-carboxylic acid (113342-32-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium t-butoxide; lithium diisopropylamide / tetrahydrofuran; heptane; diethyl ether / 0.92 h / -78 °C

1.2: 68 percent / tetrahydrofuran; heptane; diethyl ether / 72 h / 20 °C

2.1: hydrazine monohydrate / ethanol / 1.5 h / Heating

2.2: NaOH / ethanol / 1.5 h / Heating

With potassium tert-butylate; hydrazine hydrate; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; ethanol; n-heptane;

DOI:10.1002/jlcr.952

Reference yield:

5-(4-chloro-3-methylphenyl)-1-H-pyrazole-3-carboxylic acid (113342-32-8) → 5-(4-chloro-3-methyl-phenyl)-1H-pyrazole-3-carbonyl chloride (877994-55-3)

Guidance literature:

With thionyl chloride; In toluene; for 1.25h; Heating;

DOI:10.1002/jlcr.952

upstream raw materials:

4-(4-chloro-3-methylphenyl)-2,4-dioxobutyric acid ethyl ester

4-chloro-3-methylacetophenone

Downstream raw materials:

5-(4-chloro-3-methyl-phenyl)-1H-pyrazole-3-carbonyl chloride

N-[(1S)-endo-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl]-5-(4-chloro-3-methyl-phenyl)-1-H-pyrazole-3-carboxamide