1072-91-9

Basic information

• Product Name: 1,3,5-Trimethylpyrazole
• Synonyms: 1,3,5-Trimethylpyrazole ,98%;1,3,5,-Trimethylpyrazole,99%;1,3,5-TriMethylpyrazole, 97+%;1,3,5-Trimethyl-1H-pyrazole98%;VITAS-BB TBB000655;1H-Pyrazole, 1,3,5-trimethyl-;Pyrazole, 1,3,5-trimethyl-;1,3,5-TRIMETHYL-1H-PYRAZOLE
• CAS NO: 1072-91-9
• Molecular Formula: C₆H₁₀N₂
• Molecular Weight: 110.16
• EINECS: 1312995-182-4
• Product Categories: Pyrazoles;Pyrazoles & Triazoles;Nucleotides and Nucleosides;Bases & Related Reagents;Nucleotides;Pyrazoles & Triazoles;Building Blocks;Heterocyclic Building Blocks
• Mol File: 1072-91-9.mol

Chemical Properties

• Melting Point: 38-41 °C(lit.)
• Boiling Point: 168-170 °C
• Flash Point: 93 °F
• Appearance: White low-melting solid
• Density: 0.93
• Vapor Pressure: 3.17mmHg at 25°C
• Refractive Index: 1.4589
• Storage Temp.: Room temperature.
• Solubility: soluble in Methanol
• PKA: 3.30±0.10(Predicted)
• BRN: 110515
• CAS DataBase Reference: 1,3,5-Trimethylpyrazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5-Trimethylpyrazole(1072-91-9)
• EPA Substance Registry System: 1,3,5-Trimethylpyrazole(1072-91-9)

Safety Data

• Hazard Codes: Xi,F
• Statements: 10-36/37/38
• Safety Statements: 16-26-36
• RIDADR: UN 1325 4.1/PG 3
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 1072-91-9(Hazardous Substances Data)

Usage

Chemical Properties

White Low-Mekting Solid

Synthesis Reference(s)

Canadian Journal of Chemistry, 71, p. 410, 1993 DOI: 10.1139/v93-060

InChI:InChI=1/C6H10N2/c1-5-4-8(3)7-6(5)2/h4H,1-3H3

Upstream product

• 60-34-4 methylhydrazine 
• 123-54-6 acetylacetone 
• 67-51-6 3,5-dimethyl-1H-pyrazole 
• 67-56-1 methanol 
• 1118-66-7 4-Aminopent-3-en-2-one 
• 343866-85-3 3-acetyl-4-(t-butylamino)-3-penten-2-one 
• 616-38-6 carbonic acid dimethyl ester 
• 123-91-1 1,4-dioxane 
• 102-85-2 tri-n-butyl phosphite 
• 10025-83-9 iridium (III) chloride 
• 74-88-4 methyl iodide 
• 56-23-5 tetrachloromethane 
• 55458-67-8 1,3-dimethyl-1H-pyrazole-5-carbonyl chloride 
• 98298-63-6 1,3,5-trimethylpyrazole-4-carboxylic acid chloride 

Downstream Products

• 2644-93-1 1,3,5-trimethyl-1H-pyrazole-4-carbaldehyde 
• 1360571-25-0 1,3,5-trimethyl-4-(phenylthio)-1H-pyrazole 
• 637336-33-5 N-{4-[3-cyclopropyl-methyl-1-(2-fluorobenzyl)-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl]-phenyl}-N-methyl-2-oxo-2-(1,3,5-trimethyl-1H-pyrazol-4-yl)-acetamide 
• 1356914-66-3 C₁₁H₁₈N₂OS₂ 
• 1219035-03-6 4-(4-nitrophenyl)-1,3,5-trimethylpyrazole 
• 1179669-63-6 2-(1,3,5-trimethylpyrazol-4-yl)benzaldehyde 
• 1183805-72-2 4-(1,3,5-trimethylpyrazol-4-yl)benzaldehyde 
• 1179889-87-2 4-(1,3,5-trimethylpyrazol-4-yl)acetophenone 
• 1219035-07-0 4-[4-(dimethylamino)phenyl]-1,3,5-trimethylpyrazole 
• 1219035-08-1 4-[3,5-bis(trifluoromethyl)phenyl]-1,3,5-trimethylpyrazole 
• 1219035-02-5 4-(4-trifluoromethylphenyl)-1,3,5-trimethylpyrazole 
• 1219035-01-4 methyl 4-(1,3,5-trimethylpyrazol-4-yl)benzoate 
• 1219035-10-5 2-(1,3,5-trimethylpyrazol-4-yl)benzonitrile 
• 1175945-62-6 4-(1,3,5-trimethylpyrazol-4-yl)benzonitrile 

Relevant articles and documents

Transition Metal-Catalyzed N-Alkylation of NH Groups of Azoles with Alcohols

Azoles containing acidic NH-group react with various alcohols in the presence of catalytic amount of ruthenium-, rhodium-, and iridium- trialkylphosphite complexes to give the corresponding N-alkylated azoles in good to excellent yields.

Simple, efficient and convenient synthesis of pyrroles and pyrazoles using zeolites

A convenient heterogeneous catalytic methodology for the synthesis of Pyrroles and Pyrazoles by an intermolecular reaction of γ or β-diketones with primary amines or hydrazine derivatives over zeolites are described.

Pyrazolium- versus imidazolium-based ionic liquids: Structure, dynamics and physicochemical properties

Ionic liquids (ILs) composed of two different pyrazolium cations with dicyanamide and bis(trifluoromethanesulfonyl)imide anions have been synthesized and characterized by NMR, Kamlet-Taft solvatochromic parameters, conductivity and rheological measurements, as well as ab initio calculations. Density functional calculations for the two pyrazolium cations, 1-butyl-2- methylpyrazolium [bmpz] and 1-butyl-2,3,5-trimethylpyrazolium [bm 3pz], provide a full picture of their conformational states. Homo- and heteronuclear NOE show aggregation motives sensitive to steric hindrance and the anions' nature. Self-diffusion coefficients D for the anion and the cation have been measured by pulsed field gradient spin-echo NMR (PGSE-NMR). The ionic diffusivity is influenced by their chemical structure and steric hindrance, giving the order Dcation > Danion for all of the examined compounds. The measured ion diffusion coefficients, viscosities, and ionic conductivity follow the Vogel-Fulcher-Tammann (VFT) equation for the temperature dependencies, and the best-fit parameters have been determined. Solvatochromic parameters indicate an increased ion association upon going from bis(trifluoromethanesulfonyl)imide to dicyanamide-based pyrazolium salts, as well as specific hydrogen bond donor capability of H atoms on the pyrazolium ring. All of these physical properties are compared to those of an analogous series of imidazolium-based ILs.

Synthesis and reactivity of (pyrazol-1-yl)acyl iron complexes

Abstract Treatment of 1-methyl-3,5-dialkylpyrazoles with n-BuLi, and subsequently with iron carbonyl and iodine yielded (pyrazol-1-yl)acyl iron complexes CH2(CO) (3,5-R2Pz)Fe(CO)3I (R = Me or Pri, Pz = pyrazol-1-yl). Reaction of CH2(CO) (3,5-Me2Pz)Fe(CO)3I with PhSNa gave a dimeric complex [CH2(CO) (3,5-Me2Pz)Fe(CO)2(SPh)]2, while similar reactions of CH2(CO) (3,5-R2Pz)Fe(CO)3I with PySNa (Py = 2-pyridyl) gave mononuclear complexes CH2(CO) (3,5-R2Pz)Fe(CO)2(SPy), which exhibited an isomerization in solution. Treatment of the dimeric complex with PPh3 at room temperature resulted in the decomposition of the starting material. Furthermore, this dimeric complex readily underwent reductive elimination to generate CH2(COSPh) (3,5-Me2Pz) when heated at relatively low temperature, and thermal decomposition reaction to give PhSSPh in refluxing toluene solution. Reaction of mononuclear complexes with PPh3 caused one carbonyl to be replaced by phosphine ligand to give complexes CH2(CO) (3,5-R2Pz)Fe(CO) (PPh3) (SPy). All these acyl iron complexes were fully characterized by IR and NMR spectroscopy, and their structures were unambiguously determined by X-ray crystallography.

C- and N-amidotrichloroethylation of azoles

1H-Pyrazoles, triazoles, and imidazoles in reaction with ethoxycarbonylimine and arylsulfonylimines of chloral yield addition products, corresponding 1-(1-amidotrichloroethyl)azoles. Derivatives of 1-alkylpyrazoles and pyrazolones react with chloral 4-chl

PRODUCING METHOD OF NITROGEN-CONTAINING ORGANIC COMPOUND

A hydrazine-carbon dioxide-binding compound or hydrazine derivatives 2 carbonyl group react with a compound having one or more nitrogen-containing organic for preparing the compounds of relates to method.

N-methylation of nitrogen-containing heterocycles with dimethyl carbonate

Reactivity of dimethyl carbonate, the environmentally friendly reagent, as methylating agent for nitrogen-containing heterocyclic compounds has been studied. Reactions of imidazole, pyrazole, pyrrole, morpholine, and piperazine with dimethyl carbonate to afford N-methylated products were reported. The reactions were carried out with neither catalyst nor solvent at a temperature range of 110-170°C under atmospheric pressure. Copyright Taylor & Francis, Inc.

Monomethylation of nitrogeneous heterocycles

A process for the monomethylation of nitrogenous heterocycles having at least one nitrogen atom bonded to a hydrogen atom by reacting the nitrogenous heterocycle with dimethyl carbonate at a temperature of between 100° and 200° C. and a pressure of between 0.93×105 Pa and 1.07×105 Pa while methanol produced during the reaction is distilled off as it is formed.

Heterocyclic-substituted alkylamide acat inhibitors

Pharmaceutically useful compounds having ACAT inhibitory activity of the formula wherein n is 0, 1, or 2, for X other than tetrazole and n = 2 then R2 = R3 = H; R1 is phenyl, substituted phenyl, naphthyl, substituted naphthyl, a heteroaromatic group or a hydrocarbon group having from one to 18 carbon atoms; R2 and R3 are hydrogen, halo, hydroxy, alkyl, alkenyl, cycloalkyl, phenyl, substituted phenyl, a heteroaryl, or form a spiroalkyl group; x is a 5-membered heteromonocyclic group containing at least one to four heteroatoms selected from the group consisting of isothiazole, oxazole, thiazole, imidazole, furan, thiophene, pyrrole, tetrazole, 1,2,3-triazole, 1,2,4-oxadiazole, 1,3,4-oxadiazole, 1,3,4-thiadiazole, 1,2,4-triazole, and 1,2,4-oxadiazole said heteromonocyclic group being unsubstituted or substituted at any available position along the ring,

Scope and limitations in the regioselective synthesis of 1,3,5-trisubstituted pyrazoles from β-amino enones and hydrazine derivatives. 13C-chemical shift prediction rules for 1,3,5-trisubstituted pyrazoles

β-amino enones react with hydrazine derivatives to give regioselectively 1,3,5-trisubstituted pyrazoles. The synthetic method only presents limitations when the β-substituent of the enone and the hydrazine substituent are bulky or possess an electron withdrawing character. Comparison of the 13C-NMR spectra of the seventy pyrazoles allowed us to estimate a 13C-chemical shift prediction rule for 1,3,5-trisubstituted pyrazoles, with deviations of less than ± 1 ppm.