38460-08-1

Usage

Uses

Used in Pharmaceutical Research:
1-(2-CHLORO-ETHYL)-3,5-DIMETHYL-1H-PYRAZOLE is used as a building block for the synthesis of various bioactive compounds, contributing to the development of new drugs.
Used in Agrochemical Production:
1-(2-CHLORO-ETHYL)-3,5-DIMETHYL-1H-PYRAZOLE is also utilized as a building block in the production of agrochemicals, indicating its potential applications in agriculture for pest control and crop protection.
It is important to handle 1-(2-CHLORO-ETHYL)-3,5-DIMETHYL-1H-PYRAZOLE with care and follow all safety protocols due to its potential health hazards if mishandled.

InChI:InChI=1/C7H11ClN2/c1-6-5-7(2)10(9-6)4-3-8/h5H,3-4H2,1-2H3

Upstream product

• 123-54-6 acetylacetone 
• 67-51-6 3,5-dimethyl-1H-pyrazole 
• 107-04-0 1-Bromo-2-chloroethane 
• 107-06-2 1,2-dichloro-ethane 

Downstream Products

• 131727-18-9 N-(phenyl)-N-[1-(2-(3,5-dimethyl-1H-pyrazol-1-yl)-ethyl)-4-methoxycarbonyl-4-piperidinyl]-propanamide 
• 131727-20-3 N-(phenyl)-N-[1-(2-(3,5-dimethyl-1H-pyrazol-1-yl)-ethyl)-4-methoxymethyl-4-piperidinyl]propanamide 
• 491837-90-2 1-[(P-diphenyl)-2-phosphinoethyl]-3,5-dimethylpyrazole 
• 847474-63-9 1-[2-(3,5-dimethylpyrazol-1-yl)ethyl]-3-(4-fluorobenzyl)-3H-imidazol-1-ium chloride 
• 847474-64-0 1-[2-(3,5-dimethylpyrazol-1-yl)ethyl]-3-(2,4,6-trimethylphenyl)-3H-imidazol-1-ium chloride 

Relevant academic research and scientific papers

New diorganoselenium(II) compounds and their behavior toward late transition metals

Hypervalent diorganoselenium(II) compounds of type 1-{2-[(2-(3,5-dimethyl- 4,5-dihydro-1H-pyrazol-1-yl)ethyl)selanyl]phenyl}-N,N-dialkylmethanamine, [2-(R2NCH2)C6H4][(3,5-dmpz)CH2CH 2]Se, [R = Me (1), Et (2), dmpz = dimethylpyrazole] were obtained by reacting 1-(2-bromoethyl)-3,5-dimethyl-1H-pyrazole [(3,5-dmpz)CH 2CH2Br] with alkali metal aryl selenolates of type [2-(R2NCH2)C6H4]SeM (R = Me, M = Na; R= Et, M = Li) in a 1:1 molar ratio. The coordination ability of species 1, as well as that of bis[2-(3,5-dimethyl-1H-pyrazol-1-yl)ethyl]selane, [(3,5-dmpz)CH2CH2]2Se (3) toward several late transition metals (Pd, Au, Ag) was investigated by reacting the neutral ligands 1 and 3 with PdCl2, AuCl(tht) and AgOTf in a 1:1 molar ratio. The neutral ligands 1-3, as well as thegold(I), silver(I) and palladium(II) adducts [2-(Me2-NCH2)C6H4][(3,5-dmpz)CH 2CH2)]SeAuCl (4), [(3,5-dmpz)CH2CH 2)]2SeAuCl (5), [2-(Me2NCH2)C 6H4][(3,5-dmpz)CH2CH2)]SeAgOTf (6), [(3,5-dmpz)CH2CH2)]2SeAgOTf (7) and [(3,5-dmpz)CH2CH2)]2SePdCl2 (8) were characterized by NMR spectroscopy (1H, 13C, 77Se) and mass spectrometry. The reaction between 1 and PdCl 2 in a 1:1 molar ratio resulted in the formation of a complex reaction mixture of which the species [2-(Me2NCH2)C 6H4SePdCl]2 (9) and 1-(2-chloroethyl)-3,5- dimethyl-1H-pyrazole [(3,5-dmpz)CH2-CH2Cl] were unambiguously identified. Single crystal X-ray diffraction studies revealed a monomeric structure with a distorted T-shaped coordination geometry of type (C,N)SeC for the neutral ligand 1 and supramolecular associations based on dimeric units in case of species 9 and 90.5CH2Cl20.5THF.

Synthesis of N-vinylpyrazoles

A method is proposed for the alkylation of pyrazoles with dichloroethane in water in the presence of the phase-transfer catalyst benzyltriethylammonium chloride (TEBAC). It was shown that dehydrochlorination of the corresponding N-(β-chloroethyl)pyrazoles in water under conditions of phase-transfer catalysis proceeds smoothly with the formation of N-vinylpyrazoles in 80-90% yield. 2005 Springer Science+Business Media, Inc.

Synthesis and characterization of some symmetrical substituted 1-(2-chloroethyl)pyrazole-based chalcogenides

The present paper describes the synthesis of some symmetrical substituted 1-(2-chloroethyl) pyrazole-based dichalcogenides and monochalcogenides by reacting different 3,4,5-trisubstituted 1-(2-chloroethyl) pyrazole derivatives with in situ prepared Na2E2 (E = S, Se, Te) and sodium hydrogen selenide, respectively. All compounds were fully characterized by different spectroscopic techniques, namely, IR, 1H, 13C, 77Se nuclear magnetic resonance, and mass spectrometry. X-ray crystal structure determination of 1,2-bis(2-(4-bromo-3,5-dimethyl-1H-pyrazol-1-yl)ethyl)diselane (10b) reveals intermolecular Se·N·H interactions between two molecules.

Synthesis and structural characterization of metal complexes based on pyrazole/imidazolium chlorides

A series of imidzoalium salt, L ? HCl, for the potentially bidentate pyrazole/N-heterocyclic carbene was synthesized. Reactions of a 2:1 mixture between L ? HCl bearing bulky N-substitution and Ag2O produced Ag(L)Cl, whereas a novel compound with unique stoichiometry AgL 2(AgCl)0.5Cl was produced from L ? HCl bearing N-methyl group under identical condition. Reactions of L ? HCl with PdCl2 produced zwitterionic PdIICl3L ? H. Selected structural determinations on L ? HCl, Ag(L)Cl, AgL 2(AgCl)0.5Cl, and PdIICl3L ? H revealed intriguing crystal chemistry in which the less-stable gauche rotamers were obtained exclusively. A preliminary application of the zwitterionic complexes, PdIICl3L ? H, in Heck coupling reaction of aryl bromide with n-butyl acrylate shows effective activity.

Synthesis of a new potentially hemilabile ligand: 1-[2-(diphenylphosphanyl)ethyl]-3,5-dimethylpyrazole, and comparison of its bonding properties with the related 1-[2-(ethylamino)ethyl]-3,5-dimethylpyrazole ligand toward RhI

The new ligand 1-[2-(diphenylphosphanyl)ethyl]-3,5-dimethylpyrazole (2) has been prepared by the reaction of 1-(chloroethyl)-3,5-dimethylpyrazole and PPh2Li. The bidentate N,N ligand 1-[2-(ethylamino)ethyl]-3,5-dimethylpyrazole (1) and 2 react with [Rh(COD)(THF)2][BF4] to give [Rh-(COD)(1)][BF4] (3) and [Rh(COD)(2)][BF4] (4), respectively. Substitution of 1,5-cyclooctadiene with carbon monoxide in the latter complexes generates [Rh(CO)2(1)][BF4] (5) and [Rh(CO)2(2)][BF4] (6), respectively. Treatment of Rh(COD)(THF)2][BF4] with two equivalent amounts of 2 results in the complex [Rhf2)2][BF4] (7), which converts to [Rh(CO)(2)2][BF4] (8) on reaction with carbon monoxide. Ligand 2 in complex 8 exhibits a hemilabile character. The single-crystal X-ray structures of 3, 4, and 7 are reported. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

New 1-(heterocyclylalkyl)-4-(propionanilido)-4-piperidinyl methyl ester and methylene methyl ether analgesics

A series of new 1-(heterocyclyalkyl)-4-(propionanilido)-4-piperidinyl methyl esters and methylene methyl ethers have been synthesized and pharmacologically evaluated. In the mouse hot-plate test, the majority of compounds exhibited an analgesia (ED50 1 mg/kg) superior to that of morphine. These studies revealed a pharmacological accommodation for many more structurally diverse and far bulkier aromatic ring systems than the corresponding components of the arylethyl groups of the prototypic methyl ester (carfentanil, 2) and methylene methyl ether (sufentanil, 3 and alfentanil, 4) 4-propionanilido analgesics. Compound 9A (methyl 1-[2-(1H-pyrazol-1-yl)-ethyl]-4-[(1-oxopropyl) phenylamino]-4-piperidinecarboxylate), which exhibited appreciable μ-opioid receptor affinity, was a more potent and short-acting analgesic, than alfentanil with less respiratory depression in the rat. On the other hand, the phthalimides 57A and 57B, which exhibited negligible affinity for opioid receptors associated with the mediation of nociceptive transmission (i.e., μ-, κ-, and δ-subtypes), displayed analgesic efficacy in all antinociception tests. In addition, while 57B, compared to clinical opioids, showed a superior recovery of motor coordination after regaining of righting reflex from full anesthetic doses in the rat rotorod test, 57A showed significantly less depression of cardiovascular function at supraanalgesic doses in the isoflurane-anesthetized rat.

ALKYLATION OF AZOLES USING beta -FUNCTIONAL ALKYL HALIDES UNDER CONDITIONS OF PHASE TRANSFER CATALYSIS.

The objective of this study was to develop a convenient synthetic method for direct N-alkylation of pyrazole (I), 3(5)-methylpyrazole (II), 3,5-dimethylpyrazole (III), 1,2,4-triazole (IV), and tetrazole (V) using beta -functional alkyl halides under conditions of two-phase catalysis and with high product yields. This investigation was stimulated by the fact that the desired reaction products are intermediates in the synthesis of an important class of compounds, vinylazole, as well as of various pharmaceutical agents. It is found that depending on the acidity of the azole, alkylation with dichloroethane can be accompanied by beta -elimination. The effect of solvent on the course of alkylation reactions using dichloroethane has also been studied, and revealed that the reactions occur via the intermediacy of ion pairs rather than free anions.