180519-09-9

Basic information

• Product Name: 3-(CHLOROMETHYL)-1,5-DIMETHYL-1H-PYRAZOLE
• Synonyms: 3-(CHLOROMETHYL)-1,5-DIMETHYL-1H-PYRAZOLE;3-(Chloromethyl)-1,5-dimethyl-1H-pyrazole 97%;3-(Chloromethyl)-1,5-dimethyl-1h-pyrazole ,97%
• CAS NO: 180519-09-9
• Molecular Formula: C6H9ClN2
• Molecular Weight: 144.6
• Mol File: 180519-09-9.mol

Chemical Properties

• Melting Point: 63 °C
• Boiling Point: 225.8°Cat760mmHg
• Flash Point: 90.4°C
• Appearance: /
• Density: 1.17g/cm³
• Vapor Pressure: 0.127mmHg at 25°C
• Refractive Index: 1.542
• CAS DataBase Reference: 3-(CHLOROMETHYL)-1,5-DIMETHYL-1H-PYRAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(CHLOROMETHYL)-1,5-DIMETHYL-1H-PYRAZOLE(180519-09-9)
• EPA Substance Registry System: 3-(CHLOROMETHYL)-1,5-DIMETHYL-1H-PYRAZOLE(180519-09-9)

Safety Data

• Hazard Codes: C
• Statements: 20/21/22-58-52
• Safety Statements: 16-3/7-36/37
• Hazardous Substances Data: 180519-09-9(Hazardous Substances Data)

Usage

Chemical Properties

White solid

InChI:InChI=1/C6H9ClN2/c1-5-3-6(4-7)8-9(5)2/h3H,4H2,1-2H3

Upstream product

• 4027-57-0 ethyl 5-methyl-1H-pyrazole-3-carboxylate 
• 153912-60-8 (1,5-dimethyl-1H-pyrazol-3-yl)methanol 
• 615-79-2 ethyl 2,4-diketopentanoate 
• 5744-51-4 ethyl 1,5-dimethyl-1H-pyrazole-3-carboxylate 

Downstream Products

• 1184869-53-1 (S)-benzofuran-5-ylmethyl 1-(diisobutylamino)-3-(4-((1,5-dimethyl-1H-pyrazol-3-yl)methoxy)phenyl)-1-oxopropan-2-ylcarbamate 

Relevant articles and documents

Pyrazole functionalized n-heterocyclic carbene ruthenium compound with anticancer activity and preparation method and application thereof

The invention discloses a pyrazole functionalized n-heterocyclic carbene ruthenium compound with anticancer activity and a preparation method and application thereof. The pyrazole functionalized n-heterocyclic carbene ruthenium compound is prepared by using 5-methyl-1-hydrogen-pyrazole ethyl formate through alkylation, reduction, chlorination, salt formation and metal exchange reaction, and the general formula of the pyrazole functionalized n-heterocyclic carbene ruthenium compound is [LRu(p-cymene)Cl](X) (L=pyrazole functionalized n-heterocyclic carbene ligand, and X is anions). In the cytotoxicity test of breast cancer cells (Bcap-37), intestinal cancer cells (LoVo), gastric cancer cells (SCG7901) and cisplatin-resistant gastric cancer cells (SCG7901-R), the n-heterocyclic carbene ruthenium compound can effectively inhibit cancer cell division and reproduction. The n-heterocyclic carbene ruthenium compound is variable in structure, convenient to synthesize, stable in performance, environmentally friendly, capable of stably existing in air for a long time, and promising in application prospect of pharmaceutical industry and fine chemical engineering industry.

Synthesis and enzyme inhibitory activities of some new pyrazole-based heterocyclic compounds

Three tridentate N,N-bis(3,5-dimethylpyrazol- 1-ylmethyl)-1-hydroxy-2- aminoethane (2), N,N-bis(3,5-dimethylpyrazol- 1-ylmethyl)-cyclohexylamine (3) and 2-[bis (1,5-dimethyl-1H-pyrazol-3-ylmethyl)amino]ethan-1-ol (4) are synthesized and spectroscopically characterized togetherwith 1-hydroxymethyl-3,5-dimethylpyrazole (1). These have been tested in inhibitory activities against various hyperactive enzymes like urease, β- glucuronidase, phosphodiesterase, α-chymotrypsin, acetylcholinesterase and butyrylcholinesterase. Compounds 1, 2 and 3 were found to be selective inhibitors of urease. Compound 4 was found to be selective inhibitor of butyrylcholinesterase. The nature of the junction between pyrazoles cycles determined the activities of these tripods. While the tripods are inactive towards urease or glucuronidase, they turn to be selective towards butyrylcholinesterase.

Stereoselective synthesis of 12,13-cyclopropyl-epothilone B and side-chain-modified variants

A general strategy has been devised for the stereoselective synthesis of 12,13-cyclopropyl-epothilone B and side-chain-modified variants thereof, which relies on late stage introduction of the heterocycle through Wittig olefination of ketone 14. Formation of the macrocycle was achieved through RCM-based ring closure and introduction of the cyclopropane moiety involved a highly selective Charette cyclopropanation of allylic alcohol 7.

5-lipoxygenase-activating protein (FLAP) inhibitors. Part 4: Development of 3-[3-tert-butylsulfanyl-1-[4-(6-ethoxypyridin-3-yl)benzyl]-5-(5-methylpyridin- 2-ylmethoxy)-1 H -indol-2-yl]-2,2-dimethylpropionic acid (AM803), a potent, oral, once daily FLAP inhibitor

The potent 5-lipoxygenase-activating protein (FLAP) inhibitor 3-[3-tert-butylsulfanyl-1-[4-(6-ethoxypyridin-3-yl)benzyl]-5-(5-methylpyridin-2- ylmethoxy)-1H-indol-2-yl]-2,2-dimethylpropionic acid 11cc is described (AM803, now GSK2190915). Building upon AM103 (1) (Hutchinson et al. J. Med Chem.2009, 52, 5803-5815; Stock et al. Bioorg. Med. Chem. Lett. 2010, 20, 213-217; Stock et al. Bioorg. Med. Chem. Lett.2010, 20, 4598-4601), SAR studies centering around the pyridine moiety led to the discovery of compounds that exhibit significantly increased potency in a human whole blood assay measuring LTB4 inhibition with longer drug preincubation times (15 min vs 5 h). Further studies identified 11cc with a potency of 2.9 nM in FLAP binding, an IC50 of 76 nM for inhibition of LTB4 in human blood (5 h incubation) and excellent preclinical toxicology and pharmacokinetics in rat and dog. 11cc also demonstrated an extended pharmacodynamic effect in a rodent bronchoalveolar lavage (BAL) model. This compound has successfully completed phase 1 clinical studies in healthy volunteers and is currently undergoing phase 2 trials in asthmatic patients.