38521-06-1

Basic information

• Product Name: 2-Mercaptopyrazine
• Synonyms: 2-Mercaptopyrazine;pyrazine-2(1H)-thione;2-Mercaptopyrazine 97% (HPLC)
• CAS NO: 38521-06-1
• Molecular Formula: C₄H₄N₂S
• Molecular Weight: 112.15
• Product Categories: API intermediates;Pyrazines
• Mol File: 38521-06-1.mol

Chemical Properties

• Melting Point: 207-213°C
• Boiling Point: 191.3oC at 760 mmHg
• Flash Point: 69.5oC
• Appearance: /
• Density: 1.3g/cm3
• Vapor Pressure: 0.519mmHg at 25°C
• Refractive Index: 1.662
• Storage Temp.: 2-8°C
• PKA: 8.44±0.20(Predicted)
• CAS DataBase Reference: 2-Mercaptopyrazine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Mercaptopyrazine(38521-06-1)
• EPA Substance Registry System: 2-Mercaptopyrazine(38521-06-1)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 38521-06-1(Hazardous Substances Data)

Usage

Uses

Used in Food and Beverage Industry:
2-Mercaptopyrazine is used as a flavoring agent for adding a savory, roasted, and nutty aroma to food and beverages, enhancing the sensory experience for consumers.
Used in Perfume and Fragrance Industry:
In the production of perfumes and fragrances, 2-Mercaptopyrazine serves as an additive that imparts a unique and distinctive odor, contributing to the complexity and appeal of scent compositions.
Used in Pharmaceutical Applications:
2-Mercaptopyrazine has been studied for its potential pharmaceutical uses, particularly for its antimicrobial and antioxidant properties, indicating its possible role in the development of new therapeutic agents.

InChI:InChI=1/C4H4N2S/c7-4-3-5-1-2-6-4/h1-3H,(H,6,7)

Upstream product

• 14508-49-7 2-chloropyrazin 
• 147032-16-4 2-(4-Methoxybenzylthio)pyrazine 

Downstream Products

• 164352-89-0 2-(allylthio)pyrazine 
• 21948-70-9 2-(methylthio)pyrazine 
• 96129-41-8 2-(2-phenylethynyl)pyrazine 

Relevant articles and documents

Metalation of t-Butyl Sulfoxides, Sulfones and Sulfonamides of Pyridazine and Pyrazine. Metalation of Diazines. XX

In the pyridazine series, the use of tert-butylsulfinyl and tert-butylsulfonyl as ortho directing groups for metalation has been tested. Various functionalized products were obtained in good yields. In the case of 3-tert-burylsulfinyl-6-methoxypyridazine, the metalation was regioselective in ortho to the sulfinyl group. The metalation of 2-tert-butylsulfinyl and 2-tert-butylsulfonylpyrazine gave low to moderate yields. Synthesis of diazinesulfonamides were improved and the metalation of N-tert-butylsulfonamidopyrazine was achieved.

A novel hexanuclear silver(I) complex with photoluminescence properties

A hexanuclear complex of d10–d10transition metal with organosulfur ligand, Ag6(py2t)6(py2t?=?pyrazine-2-thiol), has been synthesized using diffusion methodology at room temperature. Crystal structure was revealed using single crystal X-ray diffraction and data indicate that the complex synthesized containing Ag–Ag bonds in the silver cluster. The density function theory (DFT) calculation was performed to investigate the molecular orbital and photoluminescence potential. The photoluminescence properties of the complex have been further investigated, and a favorable fluorescence property was observed from the complex.

Inhibition of lipopolysaccharide-induced inducible nitric oxide synthase expression by a novel compound, mercaptopyrazine, through suppression of nuclear factor-kappaB binding to DNA

Macrophage cells in response to cytokines and endotoxins produced a large amount of nitric oxide (NO) by expression of inducible nitric oxide synthase (iNOS), resulting in acute or chronic inflammatory disorders including septic hypotension and atherosclerosis. In the present study, we investigated the effect and the mechanism of mercaptopyrazine (MP) in the induction of iNOS and NO production as a culminating factor for several inflammatory disorders. Pretreatment of MP alleviated the mortality of endotoxemic mice receiving a lethal bolus of lipopolysaccharide (LPS), which was associated with the reduced levels of serum nitrite/nitrate and IL-1β. In RAW264.7 mouse macrophage cells, MP (300 μM) inhibited both protein and mRNA levels of iNOS stimulated by LPS/interferon-γ (IFNγ) up to 50%. The nuclear factor-kappa B (NF-κB)-driven transactivation was also suppressed by MP to the same degree. Treatment of MP reduced the binding of NF-κB to the oligonucleotides containing NF-κB consensus sequence, while it did not affect the translocation of NF-κB to nuclear. Suppression of NF-κB activity by MP was completely reversed by a reducing agent, dithiothreitol, implying that MP might oxidize the sulfhydryl group(s) of DNA binding domain of NF-κB. In conclusion, MP would be one of interesting candidates or chemical moieties of iNOS expression inhibitor via specific suppression of NF-κB binding to DNA, and be useful as a chemopreventive agent or a therapeutic against iNOS-associated inflammatory diseases.

Silver-organic frameworks containing ethynediide or ethynide with ancillary oligo-α-sulfanylpyrazinyl and dimethylsulfoxide ligands

Five new silver(I)-organic frameworks containing ethynediide or alkyl and aryl ethynide, together with newly designed oligo-α-sulfanylpyrazinyl ligands, namely, [(Ag2C2)2(AgCF 3COO)11(L1)(μ2-DMSO) 3(DMSO)5]·1/4H2O (L1 = 2,6-bis(pyridin-2-ylthio)pyrazine, 1), [(Ag2C 2)2(AgCF3COO)11(L 2)(μ2-DMSO)5(DMSO)3] ·1/4H2O (L2 = 2-(pyrazin-2-ylthio)-6-(pyridin-2-ylthio)pyrazine, 2), [(AgCi - C tBu)2(AgCF3COO)5(L 3)(DMSO)3(H2O)] (L3 = 2,6-bis(pyrazin-2-ylthio)pyrazine, 3), [(AgCi - CPh)4(AgCF 3COO)2(L3)(DMSO)2] ·DMSO·1/2H2O (4), and [(AgCi - CC6H4Cl-3)4(AgCF 3COO)2(L3)(DMSO)]·H2O (5), have been synthesized and characterized by X-ray crystallography. Isomorphous complexes 1 and 2 feature an infinite coordination chain composed of (C 2)2Ag15 clusters alternatively linked by L 1 or L2 ligands; weak intermolecular C- H···F hydrogen bonding between adjacent infinite chains results in a three-dimensional supramolecular network. Complex 3 exhibits a coordination layer structure composed of (tBuC2) 2Ag7 aggregates. Compounds 4 and 5 are nearly isostructural, each possessing a ladder-like chain with a centrosymmetric (arylC2)8Ag12 cluster as its structure building unit. With the assistance of weak intermolecular hydrogen bonds, three-dimensional and two-dimensional supramolecular architectures were generated in 4 and 5, respectively. The diverse coordination modes of oligo-α-sulfanylpyrazinyl ligands Ln (n = 1, 2, 3) account for the variable framework dimensionalities observed for 1-5. Notably, complexes 3-5 provide the first examples of extended, conformationally flexible N-donor ancillary ligands incorporated into silver alkyl and aryl ethynide systems. In addition, complexes 1-5 display ligand-based photoluminescence.

IMPROVED MODULATORS OF HEC1 ACTIVITY AND METHODS THEREFOR

Compounds, compositions, and methods for modulation of Hec1/Nek2 interaction are provided. Such compounds disrupt Nek2/Hec1 binding and may be useful as chemotherapeutic agents for neoplastic diseases

Oxazoles and their agricultural compositions

A compound having the formula R--S(O)n CH2 CH2 CH=CF2, wherein R is a phenyl group or a heterocyclic group selected from furyl, thienyl, isoxazolyl, isothiazolyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, 1,2,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-oxadiazolyl, 1,3,4-thidiazolyl, tetrazolyl, pyridyl, pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,3,4-triazinyl, and 1,3,5-triazinyl groups, said phenyl or heterocyclic group being optionally substituted by optionally substituted alkyl, optionally substituted alkenyl, alkynyl, cycloalkyl, alkylcycloalkyl, alkoxy, alkenyloxy, alkynyloxy, hydroxyalkyl, alkoxyalkyl, optionally substituted aryl, optionally substituted arylalkyl, optionally substituted heteroaryl, optionally substituted heteroarylalkyl, optionally substituted aryloxy, optionally substituted arylalkoxy, optionally substituted aryloxyalkyl, optionally substituted heteroaryloxy, optionally substituted heteroarylalkoxy, optionally substituted heteroaryloxyalkyl, haloalkyl, haloalkenyl, haloalkynyl, haloalkoxy, haloalkenyloxy, haloalkynyloxy, halogen, hydroxy, cyano, nitro, --NR7R8, --NR7COR8, --NR7CSR8, --NR7SO2R8, --N(SO2R7)(SO2R8), --COR7, --CONR7R8, -alkylCONR7R8, --CR7NR8, --COOR7, --OCOR7, --SR7, --SOR7, --SO2R7, -alkylSR7, -alkylSOR7, -alkylSO2R7, --OSO2R7, --SO2NR7R8, --CSNR7R8, --SiR7R8R9, --OCH2CO2R7, --OCH2CH2CO2R7, --CONR7SO2R8, -alkylCONR7SO2R8, --NHCONR7R8, --NHCSNR7R8, or an adjacent pair of R1, R2, R3, R4, R5 and R6 when taken together form a fused 5- or 6-membered carbocyclic or heterocyclic ring; R7, R8 and R9 are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, alkynyl, optionally substituted aryl or optionally substituted arylalkyl, haloalkyl, haloalkenyl, haloalkynyl, halogen or hydroxy.

Chemopreventive compounds and a preparation method and use thereof

Disclosed herein is a compound having formula (I), wherein R 1 represents a hydrogen atom or a C 1-3 alkyl group; and R 2 represents phenyl and furanyl group, or a group represented by the formula: --C(R a) C(R b)(R c), wherein R a, R b, and R c, being the same or different from each other, means hydrogen atom or methyl or phenyl group. The present invention further provides a method for preparing the compound (I) and a composition comprising as an active ingredient the compound (I). The compound (I) of the present invention can effectively inhibit the expression of enzymes involved in phase I reaction while activating the expression of enzymes involved in phase II reaction, thereby can be advantageously used to protect liver from being injured by various chemicals.

Studies on Pyrazines. Part 25. Lewis Acid-promoted Deoxidative Thiation of Pyrazine N-Oxides: New Protocol for the Synthesis of 3-Substituted Pyrazinethiols

Reaction of 3-substituted pyrazine 1-oxides eith p-methoxytoluene-α-thiol in the presence of diethylcarbamoyl chloride in refluxing acetonitrile gave the corresponding 3-substituted 2-(methoxybenzylthio)pyrazines.Based on these yields, the ease of substitution is remarkably affected by nucleophilicity of the N-oxide oxygen.Addition of zinc bromide to the reaction mixture increased the yields of thiation products of 3-methyl-, 3-phenyl-, 3-(N-butylcarbamoyl)-, 3-methoxycarbonyl- and the parent pyrazine 1-oxides, but their regioselectivies were rather low.The Lewis acid-mediated reaction of 3-methoxypyrazine 1-oxide gave a different major product, the 2,6-isomer.Conversion of the sulfides to pyrazinethiols was accomplished by mercuriation and successive reduction.This debenzylation was also found to be dependent on the electron density in the pyrazine-ring.

A DIRECT SYNTHESIS OF HETEROCYCLIC THIOLS

Heterocyclic thiols (thiones) are conveniently synthesized in good yields by the reaction of heterocyclic halides with sodium thiosulfate.The reaction requires the presence of acid, either added or liberated during the reaction, to hydrolyze the intermediate thiosulfate to thiol.