5519-42-6

Basic information

• Product Name: 3,4,5-Trimethylpyrazole
• Synonyms: 3,4,5-Trimethylpyrazole;3,4,5-trimethyl-1H-pyrazole(SALTDATA: FREE);3,4,5-Trimethyl-1H-pyrazole AldrichCPR
• CAS NO: 5519-42-6
• Molecular Formula: C₆H₁₀N₂
• Molecular Weight: 110.157
• Mol File: 5519-42-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 138.5°C
• Boiling Point: 216.48°C (rough estimate)
• Flash Point: 107.2°C
• Appearance: /
• Density: 0.9473 (estimate)
• Vapor Pressure: 0.0585mmHg at 25°C
• Refractive Index: 1.4768 (estimate)
• PKA: 16.07±0.50(Predicted)
• CAS DataBase Reference: 3,4,5-Trimethylpyrazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,5-Trimethylpyrazole(5519-42-6)
• EPA Substance Registry System: 3,4,5-Trimethylpyrazole(5519-42-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 5519-42-6(Hazardous Substances Data)

Usage

General Description

3,4,5-Trimethylpyrazole, also known as TMP, is a chemical compound with the molecular formula C7H10N2. It is a colorless and odorless liquid at room temperature and is commonly used as a corrosion inhibitor and stabilizer for liquid hydrocarbon fuels. TMP is also utilized as an additive in aviation gasoline to prevent icing in aircraft fuel systems. Additionally, it functions as a solvent and is used in the production of pharmaceuticals and dyes. The compound is flammable and should be handled with caution, and exposure to TMP can cause irritation to the skin, eyes, and respiratory system.

InChI:InChI=1/C6H10N2/c1-4-5(2)7-8-6(4)3/h1-3H3,(H,7,8)

Upstream product

• 7647-01-0 hydrogenchloride 
• 89851-91-2 4-methoxy-3,3,5-trimethyl-3H-pyrazole 1-oxide 
• 89641-59-8 4-chloro-3,3,5-trimethyl-3H-pyrazole 1-oxide 
• 130478-84-1 2,2-Dichloro-1-phenyl-3-(3,4,5-trimethyl-pyrazol-1-yl)-propane-1,3-dione 
• 77287-34-4 formamide 
• 13809-09-1 1-picryl-3,4,5-trimethylpyrazole 
• 6075-97-4 1‐(2,4‐dinitrophenyl)‐3,4,5‐trimethyl‐1H‐pyrazole 
• 64-17-5 ethanol 

Downstream Products

• 23147-78-6 1-Benzyl-3,4,5-trimethylpyrazol 
• 18601-62-2 {1-(3,4,5-trimethyl)pyrazolyl}borane 
• 1333-74-0 hydrogen 
• 75-50-3 trimethylamine 

Relevant articles and documents

Rhodium(III)-Catalyzed Selective Monoarylation of β or γ C(sp3)-H Bonds Assisted by a Trimethylpyrazole Group

The selective arylation of unactivated β or challenging γ primary and secondary β-C(sp3)-H bonds has been developed with a Cp*Rh(III) catalyst assisted by a trimethylpyrazole group. A rarely reported six-membered rhodacycle has been identified in rhodium-catalyzed C(sp3)-H activation reactions. Preliminary mechanistic studies have revealed that a concerted metalation-deprotonation pathway might be involved in the C-H activation step.

A Study on the Reactions of some Ketenes with 1-Aroyl-1H-pyrazoles

1-Aroyl-3,4,5-trimethyl-1H-pyrazoles (1a-c) react with diphenylketene (DPK) to afford the enol esters (2); this was confirmed by X-ray analysis.From the reaction of the pyrazoles (1) with dichloroketene (DCK) the pyrazolylpropanediones (3) are isolated, whereas from the reaction with dimethylketene (DMK) both the enol esters (2) and the pyrazolylpropanediones (3) were obtained.The hydrolysis of the products (3) was also studied.The corresponding pyrazolylpropanediones (10) and the enol esters (11) or their degradation products (12) were isolated from the reactions of the pyrazoles (1a-c) with some mixed anhydrides (9) in the presence of triethylamine.The structure of (10e) has also been confirmed by X-ray crystallography.Plausible schemes accounting for the formation of the products involving as a common step the quaternization of N-1 are envisaged.