2-Isobutyl-3-methoxypyrazine

Base Information

• Chemical Name: 2-Isobutyl-3-methoxypyrazine
• CAS No.: 24683-00-9
• Molecular Formula: C9H14N2O
• Molecular Weight: 166.223
• Hs Code.: 29339900
• European Community (EC) Number: 246-402-1
• UNII: S327O0T12O
• DSSTox Substance ID: DTXSID9051907
• Nikkaji Number: J126.472I
• Wikipedia: 3-Isobutyl-2-methoxypyrazine
• Wikidata: Q15633924
• Metabolomics Workbench ID: 45161
• ChEMBL ID: CHEMBL97355
• Mol file: 24683-00-9.mol

Synonyms:2-isobutyl-3-methoxypyrazine;2-methoxy-3-isobutylpyrazine;3-isobutyl-2-methoxypyrazine

Chemical Property of 2-Isobutyl-3-methoxypyrazine

Chemical Property:

• Appearance/Colour: Clear colourless liquid
• Melting Point: 107oC
• Refractive Index: n20/D 1.49(lit.)
• Boiling Point: 210.8 °C at 760 mmHg
• PKA: 0.80±0.10(Predicted)
• Flash Point: 80 °C
• PSA: 35.01000
• Density: 1g/cm³
• LogP: 1.68370
• Storage Temp.: 2-8°C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 166.110613074
• Heavy Atom Count: 12
• Complexity: 128

Purity/Quality:

99% ^*data from raw suppliers

2-Isobutyl-3-methoxypyrazine >97.0%(GC)(T) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, T, F
• Hazard Codes: Xi,T,F
• Statements: 36/37/38-39/23/24/25-23/24/25-11
• Safety Statements: 26-36-24/25-45-36/37-16-7

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC1=NC=CN=C1OC
• Description: 2-Isobutyl-3-methoxypyrazine has an extremely powerful odor with a reported threshold value of 2 parts per trillion in water. Diluted water solutions exhibit a characteristic odor of green bell peppers. May be synthesized by condensation of leucine amide with glyoxal, followed by methylation with CH2H2.
• Uses: 2-Isobutyl-3-methoxypyrazine has been employed as a model odorant molecule during an electrochemical assay for the detection of odorant molecules based on a rat odorant-binding protein (rOBP3).

Technology Process of 2-Isobutyl-3-methoxypyrazine

There total 6 articles about 2-Isobutyl-3-methoxypyrazine 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: 89.0%

2-hydroxy-3-isobutyl-pyrazine (25680-53-9) + methyl iodide (74-88-4) → 2-isobutyl-3-methoxypyrazine (24683-00-9)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 20 ℃; for 48h;

DOI:10.1002/jlcr.664

Reference yield:

D,L-leucine amide hydrochloride → 2-isobutyl-3-methoxypyrazine (24683-00-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / NaOH / methanol; H₂O / -35 - 20 °C

2: 89 percent / NaH / tetrahydrofuran / 48 h / 20 °C

With sodium hydroxide; sodium hydride; In tetrahydrofuran; methanol; water;

DOI:10.1002/jlcr.664

Reference yield:

sodium methylate (124-41-4) + 3-sec-butyl-2-chloropyrazine (57674-17-6) → 2-isobutyl-3-methoxypyrazine (24683-00-9)

Guidance literature:

In methanol;

DOI:10.1016/j.tet.2010.01.088

upstream raw materials:

2-hydroxy-3-isobutyl-pyrazine

methyl iodide

sodium methylate

3-sec-butyl-2-chloropyrazine

Refernces

• 1、 -. "1H-pyrrole-2,4-dicarbonyl-derivatives and their use as flavoring agents". . . Retrieved 2015/03/03.
• 2、 Schmarr,Sang,Ganss,Koschinski,Meusinger. "New insights into the synthesis and characterization of 2-methoxy-3-alkylpyrazines and their deuterated isotopologues". scheme or table. p. 438 - 440. Retrieved 2012/07/13.