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109-08-0

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109-08-0 Usage

Description

2-Methylpyrazine has an odor threshold in water variously reported at 60,000 or 105,000 ppb. May be prepared from the corresponding carboxylic acid; by catalytic dehydrogenation of 2-methyl-piperazine; by condensation of methylglyoxal with ethylenediamine.

Chemical Properties

Different sources of media describe the Chemical Properties of 109-08-0 differently. You can refer to the following data:
1. 2-Methylpyrazine has a nutty, cocoa, green, roasted, chocolate, meaty odor.
2. clear colorless to slightly yellow liquid

Occurrence

Reported found in bakery products, roasted barley, cocoa products, coffee, dairy products, cooked meats, peanuts, filberts, pecans, popcorn, potato chips, rum and whiskey, soy product, roasted filberts, roasted almonds, guava, papaya, asparagus, kohlrabi, baked and fried potato, milk, boiled egg, smoked fish, beer, coffee, sesame seed, rice, sukiyaki, buckwheat, sweet corn, corn tortillas, malt, wort, wild rice, okra, crayfish, clam, squid and maté.

Uses

Different sources of media describe the Uses of 109-08-0 differently. You can refer to the following data:
1. 2-Methylpyrazine is used as flavoring agents in bread fresh bread, butter, chocolate, chocolate cocoa, coffee, meat roasted, nut almond.
2. These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.

Preparation

From corresponding carboxylic acid; by catalytic dehydrogenation of 2-methyl-piperazine; by condensation of methylglyoxal with ethylenediamine

Aroma threshold values

Detection: 60 ppb to 100 ppm

Taste threshold values

Taste characteristics at 75 ppm: nutty, brown, musty, roasted and astringent

General Description

2-Methylpyrazine is an alkyl-substituted pyrazine used as a key intermediate in the synthesis of pyrazineamide, an anti-tubercular drug.

Safety Profile

Moderately toxic by ingestion and intraperitoneal routes. Mutation data reported. Flammable liquid when exposed to heat, sparks, or flame. Can react with oxidizing materials. To fight fire, use water spray, foam, dry chemical, CO2. When heated to decomposition it emits highly toxic fumes of NOx.

Purification Methods

Purify it via the picrate and distil the free base. The picrate has m133-134o(from EtOH). [Wiggins & Wise J Chem Soc 4780 1956, Beilstein 23 III/IV 911, 23/5 V 386.]

Check Digit Verification of cas no

The CAS Registry Mumber 109-08-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 9 respectively; the second part has 2 digits, 0 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 109-08:
(5*1)+(4*0)+(3*9)+(2*0)+(1*8)=40
40 % 10 = 0
So 109-08-0 is a valid CAS Registry Number.
InChI:InChI=1/C5H6N2/c1-5-4-6-2-3-7-5/h2-4H,1H3

109-08-0 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
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  • Detail
  • Alfa Aesar

  • (A14146)  2-Methylpyrazine, 99+%   

  • 109-08-0

  • 25g

  • 235.0CNY

  • Detail
  • Alfa Aesar

  • (A14146)  2-Methylpyrazine, 99+%   

  • 109-08-0

  • 100g

  • 792.0CNY

  • Detail
  • Alfa Aesar

  • (A14146)  2-Methylpyrazine, 99+%   

  • 109-08-0

  • 500g

  • 3659.0CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1223)  2-Methylpyrazine  pharmaceutiical secondary standard; traceable to PhEur

  • 109-08-0

  • PHR1223-500MG

  • 732.19CNY

  • Detail
  • Sigma-Aldrich

  • (Y0001376)  2-Methylpyrazine  European Pharmacopoeia (EP) Reference Standard

  • 109-08-0

  • Y0001376

  • 1,880.19CNY

  • Detail
  • Aldrich

  • (M75608)  2-Methylpyrazine  ≥99%

  • 109-08-0

  • M75608-25G

  • 293.67CNY

  • Detail
  • Aldrich

  • (M75608)  2-Methylpyrazine  ≥99%

  • 109-08-0

  • M75608-100G

  • 962.91CNY

  • Detail

109-08-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Methylpyrazine

1.2 Other means of identification

Product number -
Other names Pyrazine, methyl-

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:109-08-0 SDS

109-08-0Relevant articles and documents

Catalytic Synthesis Of Aziridine From 1,2-Diaminoethane

Anderson, A. A.,Simonyan, S. P.,Shimanskaya, M. V.

, p. 1134 - 1141 (1993)

The contact conversion of 1,2-diaminoethane over a tungsten trioxide catalyst at 240-580 deg C has been studied by an impulse chromatographic method.The basic reaction path under these conditions is unimolecular deaminocyclization to give aziridine (31-35percent).Piperazine and triethylenediamine, products of bi- and trimolecular deaminocyclization, are present as products.The deamination process is accompanied by coupled dehydrogenation and hydrogenolysis reactions.Addition of the acid anhydrides SiO2, P2O5 and B2O3 to the catalyst increases its activity but has onlyanegligible affect on the activation energy of the process.

Effective utilization of glycerol for the synthesis of 2-methylpyrazine over ZnO-ZnCr2O4 catalyst

Venugopal,Sarkari,Naveen Kumar,Kotesh Kumar,Syed John,Krishna Reddy,Hari Padmasri

, p. 387 - 393 (2014)

Bioglycerol an inevitable by-product in the production of biodiesel was effectively utilized for the synthesis of 2-methylpyrazine (2-MP) by vapour phase dehydrocyclization with ethylenediamine over ZnO-ZnCr2O 4(Zn-Cr-O) mixed oxides

Volatile Compounds Generated from Thermal Reaction of Methionine and Methionine Sulfoxide with or without Glucose

Yu, Tung-Hsi,Ho, Chi-Tang

, p. 1641 - 1646 (1995)

Methionine and methionine sulfoxide were mixed with or without glucose in distilled water, individually.These solutions were heated in closed sample cylinders at 180 deg C for 1 h.The volatile compounds generated were extracted using methylene chloride and analyzed by GC and GC-MS.Pyrazine compounds, especially 2,5-dimethyl-, 2-ethyl-5-methyl-, trimethyl-, and methylpyrazines were the predominant compounds among those generated from thermal interactions of glucose and methionine or methionine sulfoxide.The formation of methional or those compounds derived for methional was found to be more favorable from the thermal degradation of methionine, whereas the formation of dimethyl polysulfides, especially dimethyl disulfide and dimethyl trisulfide, was found to be more favorable from the thermal degradation of methionine sulfoxide.Glucose was found to have a catalytic effect on the formation of volatile compounds from the thermal degradation of methionine or methionine sulfoxide.Keywords: Methionine; methionine sulfoxide; methional; methyl sulfides; volatiles

Catalytic synthesis of 2-methylpyrazine over Cr-promoted copper based catalyst via a cyclo-dehydrogenation reaction route

Jing, Fangli,Zhang, Yuanyuan,Luo, Shizhong,Chu, Wei,Zhang, Hui,Shi, Xinyu

, p. 621 - 630 (2010)

The cyclo-dehydrogenation of ethylene diamine and propylene glycol to 2-methylpyrazine was performed under the atmospheric conditions at 380°C. The Cr-promoted Cu-Zn/Al 2O 3 catalysts were prepared by impregnation method and characterized by ICP-AES, N 2 adsorption/desorption, XRD, XPS, N 2O chemisorption, TPR and NH3-TPD techniques. The amorphous chromium species existing in Cu-Zn-Cr/Al 2O 3 catalyst enhanced the dispersion of active component Cu, promoted the reduction of catalyst. Furthermore, the catalytic performance was significantly improved. The acidity of the catalyst played an important role in increasing the 2-MP selectivity. To optimize the reaction parameters, influences of different chromium content, reaction temperature, liquid hourly space velocity (LHSV), reactants molar ratio and time on stream on the product pattern were studied. The results demonstrated that addition of chromium promoter revealed satisfying catalytic activity, stability and selectivity of 2-methylpyrazine. Indian Academy of Sciences.

Degradation Products Fromed from Glucosamine in Water

Shu, Chi-Kuen

, p. 1129 - 1131 (1998)

An aqueous solution of glucosamine hydrochloride was heated to 150 °C for 5 min under different pH conditions. The reaction product mixture obtained was analyzed by GC/MS. It was found that the major products formed were furfurals, especially at pH = 4 and 7. At pH = 8.5, additional flavor components were generated, including pyrazines, 3-hydroxypyridines, pyrrole-2-carboxaldehyde, furans, acetol, and several other compounds. Of the components identified, it is worthwhile to note the formation of pyrazine and methylpyrazine as major components at pH = 8.5. It is proposed that a retro-aldol condensation plays an important role in the formation of the intermediates, α-aminoacetaldehyde (I) and α-amino propanal (II). As a result, self-condensation of I generates pyrazine and combination of I and II generates methylpyrazine. In addition, it is also interesting to note the formation of 3-hydroxypyridines and pyrrole-2-carboxaldehyde. It is suggested that both groups of compounds are derived from furfurals. As the ammonia is liberated from glucosamine, it initiates the ring-opening of furfurals to form 5-amino-2-keto-3-pentenals. Intramolecular condensations of these intermediates between the amino group and the carbonyl groups lead to the formation of 3-hydroxypyridines and pyrrole-2-carboxalhyde.

Vapor phase synthesis of methylpyrazine using aqueous glycerol and ethylenediamine over ZnCr2O4 catalyst: Elucidation of reaction mechanism

Sarkari, Reema,Anjaneyulu, Chatla,Krishna, Vankudoth,Kishore, Ramineni,Sudhakar, Medak,Venugopal, Akula

, p. 1067 - 1070 (2011)

A novel method has been developed for the synthesis of methylpyrazine (MP) by using aqueous glycerol and ethylenediamine (EDA) over Zn-Cr catalyst derived from hydrotalcite precursors. The X-ray diffraction analysis of the oven-dried Zn-Cr samples synthesized at various pH ranging from 7 to 11 showed hydrotalcite phase whereas the calcined catalysts displayed ZnO and ZnCr2O 4 phases. The cyclisation activity of Zn-Cr catalyst prepared at pH ~ 9 demonstrated 99.4% conversion of EDA and 94% of glycerol with ~ 72% selectivity to MP at a reaction temperature of 400 °C. This process demonstrates direct utilization of bio-glycerol for the synthesis of MP.

SYNTHESIS OF NITROGEN CONTAINING HETEROCYCLES OVER COPPER CHROMITE

Meksh, P.A.,Anderson, A.A.,Shimanska, M.

, p. 822 - 828 (1994)

The reactions of 1,2-diaminopropane, 1-amino-2-propanol, 1-amino-2-ethanol, and N-(β-aminoethyl)-1,2-diaminoethane in the gas phase over copper chromite have been investigated with the objective of synthesising nitrogen containing heterocycles.At 240-360

Synthesis of 2-methylpyrazine on ternary oxide catalysts

Kagarlitskii,Krichevskii,Balpanov

, p. 1093 - 1095 (2005)

Synthesis of 2-methylpyrazine by cyclocondensation of ethylenediamine with 1,2-propylene glycol in the presence of zinc-molybdenum-chromium catalysts was studied.

Influence of acid-base sites on ZnO-ZnCr2O4 catalyst during dehydrocyclization of aqueous glycerol and ethylenediamine for the synthesis of 2-methylpyrazine: Kinetic and mechanism studies

Venugopal, Akula,Sarkari, Reema,Anjaneyulu, Chatla,Krishna, Vankudoth,Kumar, Mandari Kotesh,Narender, Nama,Padmasri, Aytam Hari

, p. 398 - 409 (2014)

The physicochemical characteristics of ZnO-ZnCr2O4 (Zn-Cr-O) mixed oxides were determined by adsorption and spectroscopic methods. The catalytic activities of Zn-Cr-O was investigated for dehydrocyclization of ethylenediamine and aqu

Glycerol catalytic cyclocondensation with ethanediamine to pyrazinyl compounds over the modified SiO2-Al2O3

Liu, Chuanqi,Xu, Chenghua,Xia, Tongwei,Guo, Yan,Liu, Jianying

, p. 377 - 382 (2012)

The Fe, Zn, and Mn-modified SiO2-Al2O3 catalysts for the glycerol vapor-phase cyclocondensation with ethanediamine (ED) to 2-pyrazinemethanol (2-PMol) and 2-methylpyrazine (2-MP) in a fixed-bed system were prepared by coprecipitation and characterized by N2 adsorption-desorption, X-ray powder diffraction, and NH3 temperature-programmed desorption (NH3-TPD) in the present work. The results showed that the Mn-modified SiO2-Al2O3 catalyst with a SiO2/Al2O3 molar ratio 15.84 and 6% Mn gave the highest catalytic activity for formation of 2-PMol (53.1%) and 2-MP (42.9%). Mn species could cause the modulation of the acidic species of catalysts, improving the glycerol cyclocondensation with ED to 2-PMol, and also acted as the catalytic centers for the hydrodehydration of 2-PMol to 2-MP. However, too many strong acidic sites could lead to ED self-cyclocondensation to form a by-product pyrazine. The optimum temperature was tested to be 380°C for the cyclocondensation over a 6%Mn-SiO2-Al2O 3 catalyst.

Comparison of pyrazines formation in methionine/glucose and corresponding Amadori rearrangement product model

Cui, Heping,Deng, Shibin,Hayat, Khizar,Ho, Chi-Tang,Zhai, Yun,Zhang, Qiang,Zhang, Xiaoming

, (2022/03/07)

The generation of pyrazines in a binary methionine/glucose (Met/Glc) mixture and corresponding methionine/glucose-derived Amadori rearrangement product (MG-ARP) was studied. Quantitative analyses of pyrazines and methional revealed that MG-ARP generated more methional compared to Met/Glc, whereas lower content and fewer species of pyrazines were observed in the MG-ARP model. Comparing the availability of α-dicarbonyl compounds generated from the Met/Glc model, methylglyoxal (MGO) was a considerably effective α-dicarbonyl compound for the formation of pyrazines during MG-ARP degradation, but glyoxal (GO) produced from MG-ARP did not effectively participate in the corresponding formation of pyrazines due to the asynchrony on the formation of GO and recovered Met. Diacetyl (DA) content was not high enough to form corresponding pyrazines in the MG-ARP model. The insufficient interaction of precursors and rapid drops in pH limited the formation of pyrazines during MG-ARP degradation. Increasing reaction temperature could reduce the negative inhibitory effect by promoting the content of precursors.

Application of a reusable Co-based nanocatalyst in alcohol dehydrogenative coupling strategy: Synthesis of quinoxaline and imine scaffolds

Panja, Dibyajyoti,Paul, Bhaskar,Balasubramaniam, Bhuvaneshwari,Gupta, Raju K.,Kundu, Sabuj

, (2020/01/21)

A nitrogen doped carbon supported cobalt catalyzed efficient synthesis of imines and quinoxaline motifs is reported. Co(OAc)2-Phen/Carbon-800 (Co-phen/C-800) showed the superior reactivity compared to other materials prepared at different temperature, in the synthesis of quinoxalines by the coupling between diamines and diols. Moreover, applying the transfer hydrogenation and acceptorless dehydrogenative coupling strategy, imines and quinoxaline derivatives were synthesized from the nitro compounds. The practical applicability of this protocol was demonstrated by the gram-scale synthesis and the reusability of the catalyst upto 8th cycle. Furthermore, several kinetic experiments were carried out to realize the probable mechanism.

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