2,5-Dimethylpyrazine

Base Information

• Chemical Name: 2,5-Dimethylpyrazine
• CAS No.: 123-32-0
• Molecular Formula: C6H8N2
• Molecular Weight: 108.143
• Hs Code.: 29339990
• European Community (EC) Number: 204-618-3
• NSC Number: 49139
• UNII: V99Y0MUY1Q
• DSSTox Substance ID: DTXSID6047652
• Nikkaji Number: J2.009E
• Wikidata: Q27161950
• Metabolomics Workbench ID: 46911
• ChEMBL ID: CHEMBL94709
• Mol file: 123-32-0.mol

Synonyms:2,5-dimethylpyrazine;2,5-DMP;2,6-dimethylpyrazine

Chemical Property of 2,5-Dimethylpyrazine

Chemical Property:

• Appearance/Colour: clear colorless to pale yellow liquid
• Vapor Pressure: 3.98mmHg at 25°C
• Melting Point: 15 °C
• Refractive Index: n20/D 1.502(lit.)
• Boiling Point: 155 °C at 760 mmHg
• PKA: 2.21±0.10(Predicted)
• Flash Point: 63.9 °C
• PSA: 25.78000
• Density: 0.997 g/cm³
• LogP: 1.09340
• Storage Temp.: Store below +30°C.
• Sensitive.: Hygroscopic
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.6
• 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:

98%min ^*data from raw suppliers

2,5-Dimethylpyrazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 22-36/37/38-R22
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyrazines
• Canonical SMILES: CC1=CN=C(C=N1)C
• Uses: 2,5-Dimethyl pyrazine is used for blending food, nuts and beverage flavors. 2,5-Dimethylpyrazine is used as a reagent in the synthesis of bone-targeted proteasome inhibitors for multiple myeloma (MM). 2,5-Dimethylpyrazine is also used in the preparation of 3-Methyl-2,5-bis-(2-hydroxyethyl)pyrazine (M295340); a degredation product of Clavulanic Acid (C563750) which is a β-lactamase inhibitor, typically added to amoxicillin to increase its effectiveness.

Technology Process of 2,5-Dimethylpyrazine

There total 113 articles about 2,5-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: 49.0%

2,5-dimethyl-3-chloropyrazine (95-89-6) + diethylzinc (557-20-0) → 2,5-dimethyl-pyrazine (123-32-0) + 2-ethyl-3,6-dimethylpyrazine (13360-65-1)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In N,N-dimethyl-formamide; Heating;

DOI:10.3987/R-1987-09-2449

Reference yield: 25.0%

2,5-dimethyl-3-chloropyrazine (95-89-6) → 2,5-dimethyl-pyrazine (123-32-0) + 2-ethyl-3,6-dimethylpyrazine (13360-65-1)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; diethylzinc; potassium carbonate; In N,N-dimethyl-formamide; Heating;

DOI:10.3987/R-1987-09-2449

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

upstream raw materials:

3,6-dimethyl-pyrazine-2-carboxylic acid

acetic acid

AlaOEt

3-amino-2-propanol

Downstream raw materials:

2-acetyl-3,5,6-trimethylpyrazine

2,5-diacetyl-3,6-dimethylpyrazine

2,5-pyrazinedicarboxylic acid

diethyl pyrazine-2,5-dicarboxylate

Refernces

Iridium-Catalyzed C-Alkylation of Methyl Group on N-Heteroaromatic Compounds using Alcohols

10.1021/acs.orglett.0c02635

The study presents the development of a catalytic system for the C-alkylation of N-heterocyclic compounds, such as pyridine, pyrimidine, pyrazine, quinoline, quinoxaline, and isoquinoline, using alcohols. The process is based on a hydrogen-borrowing approach and utilizes [Cp*IrCl2]2 as the catalyst precursor, combined with potassium t-butoxide and 18-crown-6-ether. This method is environmentally friendly as it only produces water as a byproduct. The researchers optimized the reaction conditions and demonstrated the system's versatility by applying it to various substrates, achieving good to excellent yields. The study also proposed a possible reaction mechanism involving three steps: hydrogen transfer from alcohol to iridium catalyst, cross-aldol-type condensation, and transfer hydrogenation. The developed catalytic system is expected to contribute to the synthesis of pharmaceuticals and functional materials.

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.