81831-68-7

Basic information

• Product Name: 2-(CHLOROMETHYL)-5-METHYLPYRAZINE
• Synonyms: 2-(CHLOROMETHYL)-5-METHYLPYRAZINE;Pyrazine, 2-(chloroMethyl)-5-Methyl-;2-Methyl-5-pyrazinylmethyl chloride;-5-methylpyrazine
• CAS NO: 81831-68-7
• Molecular Formula: C₆H₇ClN₂
• Molecular Weight: 142.59
• Mol File: 81831-68-7.mol

Chemical Properties

• Boiling Point: 212.8 °C at 760 mmHg
• Flash Point: 102.535 °C
• Appearance: /
• Density: 1.19 g/cm³
• Vapor Pressure: 0.247mmHg at 25°C
• Refractive Index: 1.53
• PKA: 1.01±0.10(Predicted)
• CAS DataBase Reference: 2-(CHLOROMETHYL)-5-METHYLPYRAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(CHLOROMETHYL)-5-METHYLPYRAZINE(81831-68-7)
• EPA Substance Registry System: 2-(CHLOROMETHYL)-5-METHYLPYRAZINE(81831-68-7)

Safety Data

• Hazardous Substances Data: 81831-68-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
2-(Chloromethyl)-5-methylpyrazine is utilized as a building block in the pharmaceutical industry for the synthesis of various drugs. Its unique structure allows for the creation of a wide range of medicinal compounds, contributing to the development of new therapeutic agents.
Used in Agrochemical Production:
In the agrochemical sector, 2-(Chloromethyl)-5-methylpyrazine serves as a key intermediate in the production of pesticides and other crop protection agents. Its chemical properties make it suitable for the formulation of effective and targeted agrochemicals.
Used in Flavoring Agent Manufacturing:
2-(Chloromethyl)-5-methylpyrazine is employed as a starting material in the creation of flavoring agents for the food and beverage industry. Its ability to impart specific tastes and aromas makes it a valuable component in the flavor chemistry.
Used in Organic Synthesis:
As a versatile building block, 2-(Chloromethyl)-5-methylpyrazine is used in organic synthesis across various chemical industries. Its reactivity and functional groups facilitate the production of a broad spectrum of fine chemicals for diverse applications.
Used in Biological Activity Research:
2-(Chloromethyl)-5-methylpyrazine is studied for its potential biological activities, such as antibacterial and antifungal properties. This research is crucial for identifying new compounds with therapeutic potential in the fields of medicine and agriculture.

InChI:InChI=1/C6H7ClN2/c1-5-3-9-6(2-7)4-8-5/h3-4H,2H2,1H3

Upstream product

• 61892-95-3 2-Hydroxymethyl-5-methylpyrazine 
• 123-32-0 2,5-dimethyl-pyrazine 

Downstream Products

• 105843-32-1 1-(2-methyl-5-pyrazinylmethyl)-2-(nitromethylene)imidazolidine 
• 98502-98-8 5-Benzyloxymethyl-2-methyl-pyrazine 1-oxide 
• 83056-60-4 2-ethoxymethyl-5-methylpyrazine-4-oxide 
• 83056-59-1 2-methoxymethyl-5-methylpyrazine-4-oxide 
• 5521-55-1 2-methylpyrazin-5-carboxylic acid 
• 952195-08-3 ethyl-(5-methyl-pyrazin-2-ylmethyl)-amine 

Relevant articles and documents

(2,5)Pyrazinophanes: Synthesis and Molecular Structure

The pseudoortho (4a) and the pseudogeminal (2,5)pyrazinophane (4b) have been synthesized via 1,6-Hofmann elimination of trimethylammonium hydroxide (2b) and dimerization of the generated 2,5-dihydro-2,5-bis(methylene)pyrazine (3).The molecular structures of both isomers, 4a and 4b, were determined by X-ray analysis.

Hederagenin compound H-X with anti-lung cancer effect and preparation method and application thereof

The invention provides a hederagenin compound H-X with an anti-tumor effect and a preparation method and application thereof. The structural general formula 1 is shown in the specifications. Most of the derivatives provided by the invention have obvious inhibition effects on tumor cells A549, MCF-7 and HepG2, and the compound hederagenin-2, 6-dimethylpyrazine (H-08) shows good selectivity betweentumors and normal conditions, especially on lung cancer A549 cells. The IC50 of the compound to A549, MCF-7, HepG2, MDCK and H9c2 is 3.45+/-0.59 muM, 8.73+/-1.49 muM, 8.71+/-0.38 muM, 14.11+/-0.04 muM, and 16.69+/-0.12 muM, the inhibition effect on A549 cells is similar to that of a positive drug cis-platinum (IC50 is 3.85+/-0.63 muM), but the toxicity on MDCK and H9c2 is obviously lower than thatof cis-platinum.

N -Hydroxyphthalimide/benzoquinone-catalyzed chlorination of hydrocarbon C-H bond using N -chlorosuccinimide

The direct chlorination of C-H bonds has received considerable attention in recent years. In this work, a metal-free protocol for hydrocarbon C-H bond chlorination with commercially available N-chlorosuccinimide (NCS) catalyzed by N-hydroxyphthalimide (NHPI) with 2,3-dicyano-5,6-dichlorobenzoquinone (DDQ) functioning as an external radical initiator is presented. Aliphatic and benzylic substituents and also heteroaromatic ones were found to be well tolerated. Both the experiments and theoretical analysis indicate that the reaction goes through a process wherein NHPI functions as a catalyst rather than as an initiator. On the other hand, the hydrogen abstraction of the C-H bond conducted by a PINO species rather than the highly reactive N-centered radicals rationalizes the high chemoselectivity of the monochlorination obtained by this protocol as the latter is reactive towards the C(sp3)-H bonds of the monochlorides. The present results could hold promise for further development of a nitroxy-radical system for the highly selective functionalization of the aliphatic and benzylic hydrocarbon C-H.

NOVEL TETRAZOLE COMPOUNDS AND THEIR USE IN THE TREATMENT OF TUBERCULOSIS

The invention relates to a compound of Formula (I) or a pharmaceutically acceptable salt thereof and their use in therapy, for example in the treatment of mycobacterial infections or in the treatment of diseases caused by mycobacterium, such as tuberculosis.

Design, synthesis, and cytotoxic analysis of novel hederagenin–pyrazine derivatives based on partial least squares discriminant analysis

Hederagenin (He) is a novel triterpene template for the development of new antitumor compounds. In this study, 26 new He–pyrazine derivatives were synthetized in an attempt to develop potent antitumor agents; they were screened for in vitro cytotoxicity against tumor and non-tumor cell lines. The majority of these derivatives showed much stronger cytotoxic activity than He. Remarkably, the most potent was compound 9 (half maximal inhibitory concentration (IC50) was 3.45 ± 0.59 μM), which exhibited similar antitumor activities against A549 (human non-small-cell lung cancer) as the positive drug cisplatin (DDP; IC50 was 3.85 ± 0.63 μM), while it showed lower cytotoxicity on H9c2 (murine heart myoblast; IC50 was 16.69 ± 0.12 μM) cell lines. Compound 9 could induce the early apoptosis and evoke cell-cycle arrest at the synthesis (S) phase of A549 cells. Impressively, we innovatively introduced the method of cluster analysis modeled as partial least squares discriminant analysis (PLS-DA) into the structure–activity relationship (SAR) evaluation, and SAR confirmed that pyrazine had a profound effect on the antitumor activity of He. The present studies highlight the importance of pyrazine derivatives of He in the discovery and development of novel antitumor agents.

He pyrrole testsamine synonym, preparation method and its application

The invention relates to the field of medicinal chemistry and particularly relates to picotamide analogues (I), a preparation method and a pharmaceutical composition containing the picotamide analogues, wherein R represents hydrogen, 3, 5, 6- trimethyl, 5-methyl or 6-methyl. The picotamide analogues provided by the invention can be used for treating or preventing thromboembolic diseases.

SUBSTITUTED XANTHINES AND METHODS OF USE THEREOF

Compounds, compositions and methods are described for inhibiting the TRPC5 ion channel and disorders related to TRPC5.

SUBSTITUTED XANTHINES AND METHODS OF USE THEREOF

Compounds, compositions and methods are described for inhibiting the TRPC5 ion channel and disorders related to TRPC5.

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.

(2,6)- and (2,5)Pyrazinophanes: Synthesis and Molecular Structure

The title compounds 1-3 and their methyl derivatives 4-7 were synthesized either by photolytic sulfur extrusion from the corresponding 2,11-dithiapyrazinophanes 24-26 or by Hofmann 1,6-elimination of the appropriate trimethylammonium hydroxides followed by dimerization of the generated 2,5-dihydro-2,5-dimethylene-pyrazines. α-Chlorination of the methylpyrazines 8-10 with N-chlorosuccinimide gave the required precursors 11, 12, 14, 17, and 18.The results of the X-ray structure determinations for 1-4 and 7 which indicate an unequivocal isomer assignment are discussed with regard to steric strain in these molecules.The electronic spectra of the pyrazinophanes 1-7 are reported and compared with those of the parent methylpyrazines.