2-Methylpyrazine

Base Information

• Chemical Name: 2-Methylpyrazine
• CAS No.: 109-08-0
• Molecular Formula: C5H6N2
• Molecular Weight: 94.116
• Hs Code.: 29339990
• European Community (EC) Number: 203-645-8
• NSC Number: 49138,30412
• UNII: RVC6500U9C
• DSSTox Substance ID: DTXSID4047620
• Nikkaji Number: J1.501F
• Wikidata: Q27161158
• Metabolomics Workbench ID: 45887
• ChEMBL ID: CHEMBL479791
• Mol file: 109-08-0.mol

Synonyms:2-METHYLPYRAZINE;109-08-0;Methylpyrazine;Pyrazine, methyl-;Pyrazine, 2-methyl-;2-METHYL PYRAZINE;2-Methyl-1,4-diazine;2-methyl-pyrazine;FEMA No. 3309;methyl-pyrazine;CCRIS 2927;EINECS 203-645-8;NSC 30412;UNII-RVC6500U9C;AI3-36550;RVC6500U9C;DTXSID4047620;CHEBI:89015;NSC-30412;NSC-49138;pyrazine, 2-methyl;WLN: T6N DNJ B1;MFCD00006142;methyl pyrazine;5-methylpyrazine;monomethylpyrazine;5-methyl pyrazine;NSC30412;Pirazina, 2-metil-;METHYL-2-PYRAZINE;2- methyl-1,4-diazine;2-Methylpyrazine, >=99%;CHEMBL479791;2-METHYLPYRAZINE [FCC];2-METHYLPYRAZINE [FHFI];DTXCID2027620;FEMA 3309;AMY23232;NSC49138;Tox21_303776;AKOS009156584;AC-3331;HY-W067358;LS-2959;2-Methylpyrazine, >=99%, FCC, FG;NCGC00188126-01;NCGC00357068-01;10-98-0;AS-13593;CAS-109-08-0;CS-0059136;FT-0613074;M0736;EN300-40909;D73175;Q-100051;Q27161158;F8889-9211;Z415628164;2-Methylpyrazine, European Pharmacopoeia (EP) Reference Standard;2-Methylpyrazine, Pharmaceutical Secondary Standard;Certified Reference Material

Chemical Property of 2-Methylpyrazine

Chemical Property:

• Appearance/Colour: clear colorless to slightly yellow liquid
• Vapor Pressure: 9.69mmHg at 25°C
• Melting Point: -29 ºC
• Refractive Index: n20/D 1.504(lit.)
• Boiling Point: 135.1 ºC at 760 mmHg
• PKA: 1.45(at 27℃)
• Flash Point: 50 ºC
• PSA: 25.78000
• Density: 1.021 g/cm³
• LogP: 0.78500
• Storage Temp.: Flammables area
• Water Solubility.: Fully miscible in water.
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 94.053098200
• Heavy Atom Count: 7
• Complexity: 54

Purity/Quality:

99%min ^*data from raw suppliers

2-Methylpyrazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,Xi,F
• Statements: 10-22-36/37/38
• Safety Statements: 26-36-16

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyrazines
• Canonical SMILES: CC1=NC=CN=C1
• 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.
• Uses: 2-Methylpyrazine is used as flavoring agents in bread fresh bread, butter, chocolate, chocolate cocoa, coffee, meat roasted, nut almond. 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.

Technology Process of 2-Methylpyrazine

There total 116 articles about 2-Methylpyrazine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

3-amino-2-propanol (78-96-6,1674-56-2) → 1,4-pyrazine (290-37-9) + 2-Methylpyrazine (109-08-0) + 2,5-dimethyl-pyrazine (123-32-0) + 2-ethyl-3,6-dimethylpyrazine (13360-65-1) + 2,3,5-trimethylpyrazine (14667-55-1) + 1-aminoethyl-2-methylaziridine

Guidance literature:

With copper chromite; at 180 ℃; for 0.333333h; Product distribution; var. temp.; other aminoalcohols;

DOI:10.1007/BF01169640

Reference yield:

2-(2-hydroxy-2-phenylpropyl)pyrazine (108246-76-0) → 2-Methylpyrazine (109-08-0) + 1-Phenylethanol (98-85-1,13323-81-4) + 2-Methyl-1,5-diphenyl-1,5-pentanedione (47074-06-6) + acetophenone (98-86-2)

Guidance literature:

DOI:10.1021/ja01530a036

Reference yield:

D-Glucose (2280-44-6) + L-alanin (56-41-7,25191-17-7,18875-37-1) → 2-Methylpyrazine (109-08-0) + 2,5-dimethyl-pyrazine (123-32-0) + 2-ethyl-3,6-dimethylpyrazine (13360-65-1) + 2,6-dimethylpyrazine (108-50-9) + 2-ethyl-6-methylpyrazine (13925-03-6) + 2-ethyl-5-methypyrazine (13360-64-0)

Guidance literature:

In various solvent(s); at 180 ℃; for 0.116667h; Product distribution; Mechanism; other amino acids (also 13C-labeled); also fructose;

DOI:10.1021/jf00059a009

upstream raw materials:

2-methylpyrazin-5-carboxylic acid

acetic acid

5-methyl-pyrazine-2,3-dicarboxylic acid

glucose

Downstream raw materials:

1-(4-methoxyphenyl)-2-(2-pyrazinyl)ethanol

3-methylpyrazin-2(1H)-one

(RS)-2-methylpiperazine

pyrazinecarboxaldehyde

Refernces

• 1、 Hurd et al.. "-". . p. 4515,4517. Retrieved 1962.
• 2、 Scalone, Gustavo Luis Leonardo,Cucu, Tatiana,De Kimpe, Norbert,De Meulenaer, Bruno. "Influence of Free Amino Acids, Oligopeptides, and Polypeptides on the Formation of Pyrazines in Maillard Model Systems". . p. 5364 - 5372. Retrieved 2015.
• 3、 Balpanov,Krichevskii,Kagarlitskii. "Binary oxide systems in catalytic synthesis of 2-methylpyrazine from 1,2-propylene glycol and ethylenediamine". . p. 2125 - 2127. Retrieved 2001.
• 4、 Teodorescu,Slabu,Pavel,Z?voianu. "A comparative study on the catalytic activity of ZnAl, NiAl, and CoAl mixed oxides derived from LDH obtained by mechanochemical method in the synthesis of 2-methylpyrazine". . . Retrieved 2020.
• 5、 Vernin, Gaston,Metzger, Jacques,Boniface, Christian,Murello, Marie-Helene,Siouffi, Antoine,et al.. "Kinetics and thermal degradation of the fructose-methionine Amadori intermediates. GC-MS/SPECMA data bank identification of volatile aroma compounds". . p. 15 - 30. Retrieved 1992.
• 6、 Hou, Jindou,Luo, Wen.,Luo, Shizhong,Lin, Chao,Liu, Ping,Liao, Xuemei,Jing, Fangli,Li, Xiaopeng. "Facile synthesis of CuMAl (M = Cr, Mn, Zn, and Co) with highly dispersed Cu and tailorable surface acidity for efficient 2-methylpyrazine synthesis". . p. 48662 - 48669. Retrieved 2017.
• 7、 Isagulyants, G. V.,Gitis, K. M.,Myasnikov, V. A.,Neumoeva, G. E.. "DEHYDROGENATION OF PIPERAZINE INTO PYRAZINE ON ALUMINA-PLATINUM CATALYSTS". . p. 1340 - 1345. Retrieved 1990.
• 8、 Kagarlitskii,Krichevskii,Amirkhanova. "Catalytic synthesis of pyrazinamide from 2,5-dimethylpyrazine". . p. 381 - 383. Retrieved 1999.
• 9、 Gitis, K. M.,Neumoeva, G. E.,Isagulyants, G. V.. "Pt/Al2O3 CATALYSTS IN THE SYNTHESIS OF NITROGEN HETEROCYCLES. CATALYTIC SYNTHESIS OF PYRAZINES". . p. 1308 - 1315. Retrieved 1993.
• 10、 Shu, Chi-Kuen. "Pyrazine formation from serine and threonine". . p. 4332 - 4335. Retrieved 1999.