36640-39-8

Basic information

• Product Name: 3-(4-chlorophenyl)-1-phenyl-1H-pyrazole-4-methanol
• Synonyms: 3-(4-chlorophenyl)-1-phenyl-1H-pyrazole-4-methanol;[3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-4-yl]methanol(SALTDATA: FREE)
• CAS NO: 36640-39-8
• Molecular Formula: C₁₆H₁₃ClN₂O
• Molecular Weight: 284.74022
• EINECS: 253-145-9
• Mol File: 36640-39-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 482.9°Cat760mmHg
• Flash Point: 245.8°C
• Appearance: /
• Density: 1.25g/cm³
• Vapor Pressure: 3.9E-10mmHg at 25°C
• Refractive Index: 1.634
• CAS DataBase Reference: 3-(4-chlorophenyl)-1-phenyl-1H-pyrazole-4-methanol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-chlorophenyl)-1-phenyl-1H-pyrazole-4-methanol(36640-39-8)
• EPA Substance Registry System: 3-(4-chlorophenyl)-1-phenyl-1H-pyrazole-4-methanol(36640-39-8)

Safety Data

• Hazardous Substances Data: 36640-39-8(Hazardous Substances Data)

Usage

Description

3-(4-chlorophenyl)-1-phenyl-1H-pyrazole-4-methanol, commonly known as JWH-018, is a synthetic cannabinoid and psychoactive chemical compound. It functions as a potent agonist for the cannabinoid receptors in the brain, eliciting effects akin to those of THC, the primary psychoactive component in marijuana.

Uses

Used in Recreational Drug Industry:
JWH-018 is utilized as a recreational drug, often marketed under the monikers "Spice" or "K2". It is typically consumed via smoking for its euphoric and psychoactive properties, providing users with an experience similar to that of marijuana.
However, it is important to note that JWH-018 is associated with a variety of negative health effects, including the potential for addiction and adverse psychiatric reactions. Due to these risks and its potential for abuse, JWH-018 is classified as a controlled substance in many jurisdictions, indicating a need for caution and regulation in its use.

InChI:InChI=1/C16H13ClN2O/c17-14-8-6-12(7-9-14)16-13(11-20)10-19(18-16)15-4-2-1-3-5-15/h1-10,20H,11H2

Upstream product

• 36663-00-0 1-phenyl-3-(4-chlorophenyl)-4-pyrazolecarboxaldehyde 
• 99-91-2 para-chloroacetophenone 
• 100-63-0 phenylhydrazine 
• 57845-08-6 p-chloroacetophenone phenylhydrazone 
• 59-88-1 phenylhydrazine hydrochloride 

Downstream Products

• 55432-06-9 4-(chloromethyl)-3-(4-chlorophenyl)-1-phenyl-1H-pyrazole 
• 55432-07-0 1-phenyl-3-(p-chlorophenyl)-pyrazol-4-acetonitrile 
• 53808-88-1 lonazolac 
• 36663-00-0 1-phenyl-3-(4-chlorophenyl)-4-pyrazolecarboxaldehyde 

Relevant articles and documents

Novel Aryl Substituted Pyrazoles as Small Molecule Inhibitors of Cytochrome P450 CYP121A1: Synthesis and Antimycobacterial Evaluation

Three series of biarylpyrazole imidazole and triazoles are described, which vary in the linker between the biaryl pyrazole and imidazole/triazole group. The imidazole and triazole series with the short -CH2- linker displayed promising antimycobacterial activity, with the imidazole-CH2- series (7) showing low MIC values (6.25-25 μg/mL), which was also influenced by lipophilicity. Extending the linker to -C(O)NH(CH2)2- resulted in a loss of antimycobacterial activity. The binding affinity of the compounds with CYP121A1 was determined by UV-visible optical titrations with KD values of 2.63, 35.6, and 290 μM, respectively, for the tightest binding compounds 7e, 8b, and 13d from their respective series. Both binding affinity assays and docking studies of the CYP121A1 inhibitors suggest type II indirect binding through interstitial water molecules, with key binding residues Thr77, Val78, Val82, Val83, Met86, Ser237, Gln385, and Arg386, comparable with the binding interactions observed with fluconazole and the natural substrate dicyclotyrosine.

Design, synthesis and biological evaluation of (1,3-diphenyl-1H-pyrazol-4-yl) methyl benzoate derivatives as potential BRAFV600E inhibitors

A series of (1,3-diphenyl-1H-pyrazol-4-yl) methyl benzoate derivatives (6a-10d) were designed, synthesized and evaluated as BRAFV600E inhibitors. Biological evaluation assays indicated that compound 10a showed the most potent inhibitory activity against A375, WM266.4 and BRAFV600Ein vitro with IC50 values of 1.36 μM, 0.94 μM and 0.11 μM respectively compared with the positive compound vemurafenib. Furthermore, compound 10a showed highly selective BRAFV600E inhibitory activity in vitro. A docking simulation displayed that compound 10a could tightly bind the crystal structure of BRAFV600E at the active site. 3D-QSAR would provide a guideline to design and optimize more potent and positive BRAFV600E inhibitors based on the (1,3-diphenyl-1H-pyrazol-4-yl) methyl benzoate derivatives skeleton.

A mild procedure for the preparation of 3-aryl-4-formylpyrazoles

A variety of 3-aryl-4-formylpyrazoles can be easily prepared in good yields from the corresponding methyl ketones, upon treatment with 2,4,6-trichloro[1,3, 5]triazine in N,N-dimethyl formamide at room temperature. This kind of pyrazole can constitute new building blocks for combinatorial chemistry.