2,3-Dimethylpyrazine

Base Information

• Chemical Name: 2,3-Dimethylpyrazine
• CAS No.: 5910-89-4
• Molecular Formula: C6H8N2
• Molecular Weight: 108.143
• Hs Code.: 29339990
• European Community (EC) Number: 227-630-0
• UNII: WHF7883D0V
• DSSTox Substance ID: DTXSID4064058
• Nikkaji Number: J45.570I
• Wikidata: Q27292638
• Metabolomics Workbench ID: 45820
• ChEMBL ID: CHEMBL96425
• Mol file: 5910-89-4.mol

Synonyms:2,3-dimethylpyrazine;2,3-DMP pyrazine

Chemical Property of 2,3-Dimethylpyrazine

Chemical Property:

• Appearance/Colour: clear yellow to orange liquid
• Vapor Pressure: 3.45mmHg at 25°C
• Melting Point: 11-13 °C
• Refractive Index: n20/D 1.507(lit.)
• Boiling Point: 158.1 °C at 760 mmHg
• PKA: 2.21±0.10(Predicted)
• Flash Point: 54.4 °C
• PSA: 25.78000
• Density: 0.997 g/cm³
• LogP: 1.09340
• Storage Temp.: Flammables area
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 108.068748264
• Heavy Atom Count: 8
• Complexity: 62.9

Purity/Quality:

99% ^*data from raw suppliers

2,3-Dimethylpyrazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, F, Xi
• Hazard Codes: Xn,F,Xi
• Statements: 10-22-37/38-41
• Safety Statements: 16-26-39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyrazines
• Canonical SMILES: CC1=NC=CN=C1C
• General Description: 2,3-Dimethylpyrazine is an alkylpyrazine derivative that serves as a key intermediate in zirconium-mediated reactions for synthesizing highly substituted alkylpyrazines, including alkenyl-, bromoalkyl-, and epoxyalkylpyrazines. Its reactivity in these transformations is influenced by steric and electronic effects, enabling regio- and stereoselective modifications to produce complex pyrazine derivatives.

Technology Process of 2,3-Dimethylpyrazine

There total 63 articles about 2,3-Dimethylpyrazine 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:

D-glucose (50-99-7) + H-Lys-Lys-OH hydrochloride (134276-45-2) → 1,4-pyrazine (290-37-9) + 2-Methylpyrazine (109-08-0) + 2,5-dimethyl-pyrazine (123-32-0) + 2,3-dimethylpyrazine (5910-89-4) + 2-ethyl-3,6-dimethylpyrazine (13360-65-1) + 2,6-dimethylpyrazine (108-50-9) + 2,3,5-trimethylpyrazine (14667-55-1) + 3-ethenyl-2,5-dimethylpyrazine (80935-98-4) + 2-ethyl-6-methylpyrazine (13925-03-6)

Guidance literature:

In water; at 130 ℃; for 2h; pH=8;

DOI:10.1021/jf903898t

Reference yield:

H-Lys-Lys-OH hydrochloride (134276-45-2) + 2-oxopropanal (78-98-8) → 2-Methylpyrazine (109-08-0) + 2,5-dimethyl-pyrazine (123-32-0) + 2,3-dimethylpyrazine (5910-89-4) + 2-ethyl-3,6-dimethylpyrazine (13360-65-1) + 2,6-dimethylpyrazine (108-50-9) + 3,5-dimethyl-2-(Z-1-propenyl)-pyrazine (55138-74-4) + 2,3,5-trimethylpyrazine (14667-55-1) + 3-ethenyl-2,5-dimethylpyrazine (80935-98-4) + 2-ethyl-3,5-dimethylpyrazine (13925-07-0) + 5-ethyl-2,3-dimethylpyrazine (15707-34-3)

Guidance literature:

In water; at 130 ℃; for 2h; pH=8;

DOI:10.1021/jf903898t

Reference yield:

D-glucose (50-99-7) + LysAla*hydrobromide (410538-35-1) → 1,4-pyrazine (290-37-9) + 2-Methylpyrazine (109-08-0) + 2,5-dimethyl-pyrazine (123-32-0) + 2,3-dimethylpyrazine (5910-89-4) + 2-ethyl-3,6-dimethylpyrazine (13360-65-1) + 2,6-dimethylpyrazine (108-50-9) + 2,3,5-trimethylpyrazine (14667-55-1) + 2-ethyl-6-methylpyrazine (13925-03-6) + 2-ethyl-5-methypyrazine (13360-64-0) + 5-ethyl-2,3-dimethylpyrazine (15707-34-3)

Guidance literature:

In water; at 130 ℃; for 2h; pH=8;

DOI:10.1021/jf903898t

upstream raw materials:

5,6-dimethylpyrazine-2,3-dicarboxylic acid

acetic acid

ethylenediamine

dimethylglyoxal

Downstream raw materials:

5,6-dimethyl-2-(1-pentenyl)pyrazine

2,3-bis<2-(4-chlorophenyl)ethenyl>pyrazine

2,3-Bis-[(E)-2-(4-nitro-phenyl)-vinyl]-pyrazine

2,4,6-Trimethyl-benzenesulfonate1-amino-2,3-dimethyl-pyrazin-1-ium;

Refernces

Zirconium-Mediated Reactions of Alkylpyrazines and Alkynes. Synthesis of Highly Substituted Alkylpyrazines

10.1021/jo00048a038

The research focuses on the synthesis of highly substituted alkylpyrazines using a zirconium-mediated reaction. The key chemicals involved include Cp2Zr(Me)(THF)+ (1), various alkylpyrazines such as 2,5-dimethylpyrazine and 2,3-dimethylpyrazine, and different alkynes like 1-pentyne, (trimethylsilyl)acetylene, and 1-(trimethylsilyl)propyne. The process involves a sequential one-pot addition of alkylpyrazines, alkynes, and a proton source to a solution of Cp2Zr(Me)(THF)+ in CH2Cl2, yielding (E)-alkenyl-substituted alkylpyrazines in excellent yields. The regio- and stereoselectivity observed in these reactions are attributed to steric and electronic effects. The resulting alkenylpyrazines can be further manipulated using conventional synthetic techniques to produce a variety of highly substituted alkylpyrazines, including tri- and tetrasubstituted alkylpyrazines, bromoalkylpyrazines, and epoxyalkylpyrazines.