25773-40-4

Basic information

• Product Name: 2-Isopropyl-3-methoxypyrazine
• Synonyms: 3-isopropyl-2-methoxypyrazine;Pyrazine, 2-methoxy-3-(1-methylethyl)-;2-METHOXY-3-ISOPROPYLPYRAZINE;2-METHOXY-3,5,6-ISOPROPYL PYRAZINE;2-METHOXY-3-(1-METHYLETHYL)PYRAZINE;FEMA 3358;FEMA NUMBER 3358;3-ISOPROPYL-2-METHOXYPYRAZINE 97+%
• CAS NO: 25773-40-4
• Molecular Formula: C₈H₁₂N₂O
• Molecular Weight: 152.19
• EINECS: 247-256-1
• Product Categories: Pyrazines;Pyrazine;Heterocyclic Compounds;Alkoxypyrazines;Mono- & Polyalkylpyrazines;Building Blocks;Heterocyclic Building Blocks;500 Series Drinking Water Methods;Chromatography;Drinking WaterEPA;Environmental Standards;Odor Standards
• Mol File: 25773-40-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 120-125 °C (20 mmHg)
• Flash Point: 152 °F
• Appearance: colorless clear liquid
• Density: 0.996 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.274mmHg at 25°C
• Refractive Index: n20/D 1.494(lit.)
• Storage Temp.: room temp
• PKA: 0.81±0.10(Predicted)
• CAS DataBase Reference: 2-Isopropyl-3-methoxypyrazine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Isopropyl-3-methoxypyrazine(25773-40-4)
• EPA Substance Registry System: 2-Isopropyl-3-methoxypyrazine(25773-40-4)

Safety Data

• Hazard Codes: Xi,T,F
• Statements: 36/37/38-39/23/24/25-23/24/25-11
• Safety Statements: 26-36/37/39-24/25-45-36/37-16-7-36/37/38
• RIDADR: UN 1230 3/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 25773-40-4(Hazardous Substances Data)

Usage

Description

2-Isopropyl-3-methoxypyrazine is a taste and odor compound that has been identified through headspace solid-phase microextraction (SPME) coupled with gas chromatography-mass spectrometry. It is characterized by its clear, colorless liquid appearance.

Uses

Used in Flavor and Fragrance Industry:
2-Isopropyl-3-methoxypyrazine is used as an additive for enhancing the flavor and aroma of various products. Its unique odor profile contributes to the overall sensory experience of the products it is added to, making it a valuable component in the creation of diverse scents and tastes.
Used in Analytical Chemistry:
2-Isopropyl-3-methoxypyrazine is utilized as a reference compound in the field of analytical chemistry. Its distinct chemical properties and odor characteristics make it a useful tool for calibrating and validating analytical instruments, such as gas chromatography-mass spectrometry systems, ensuring accurate and reliable results in chemical analysis.
Used in Research and Development:
In the research and development sector, 2-Isopropyl-3-methoxypyrazine serves as a key compound for studying the effects of various factors on taste and odor perception. Its use in experimental settings helps scientists better understand the underlying mechanisms of these sensory experiences and develop innovative solutions for improving product quality and consumer satisfaction.

InChI:InChI=1/C8H12N2O/c1-6(2)7-8(11-3)10-5-4-9-7/h4-6H,1-3H3

Synthetic route

2-hydroxy-3-isopropyl-pyrazine (25680-59-5) + methyl iodide (74-88-4) → 2-Isopropyl-3-methoxypyrazine (25773-40-4)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; for 48h;	89%

2-amino-3-methylbutanamide hydrochloride (93169-29-0) → 2-Isopropyl-3-methoxypyrazine (25773-40-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / NaOH / methanol; H2O / -35 - 20 °C 2: 89 percent / NaH / tetrahydrofuran / 48 h / 20 °C View Scheme

methanol (67-56-1) + 2-chloro-3-isopropyl-pyrazine (57674-20-1) → 2-Isopropyl-3-methoxypyrazine (25773-40-4)

Conditions	Yield
With sodium acetate

2-hydroxy-3-isopropyl-pyrazine (25680-59-5) → 2-Isopropyl-3-methoxypyrazine (25773-40-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: trichlorophosphate 2: sodium acetate View Scheme

2-Isopropyl-3-methoxypyrazine (25773-40-4) → C8H10N2O2 + C8H12N2O2 + C9H14N2O2 + C8H12N2O3 + C8H12N2O4 + C9H14N2O4 + 2-hydroxy-3-isopropyl-pyrazine (25680-59-5) + 2-(1-hydroxy-1-methylethyl)-3-methoxypyrazine (38346-80-4)

Conditions	Yield
With titanium(IV) oxide In water for 0.5h; Kinetics; Catalytic behavior; Irradiation;

...Expand

trifluoromethane sulfonyl chloride (421-83-0) + 2-Isopropyl-3-methoxypyrazine (25773-40-4) → C9H11F3N2O

Conditions	Yield
With dipotassium hydrogenphosphate; C46H91N3O4 In acetonitrile at 25℃; for 24h; UV-irradiation;	8 %Spectr.

Upstream product

• 67-56-1 methanol 
• 57674-20-1 2-chloro-3-isopropyl-pyrazine 
• 25680-59-5 2-hydroxy-3-isopropyl-pyrazine 
• 93169-29-0 2-amino-3-methylbutanamide hydrochloride 
• 74-88-4 methyl iodide 

Downstream Products

• 25680-59-5 2-hydroxy-3-isopropyl-pyrazine 
• 38346-80-4 2-(1-hydroxy-1-methylethyl)-3-methoxypyrazine 

Relevant articles and documents

1H-pyrrole-2,4-dicarbonyl-derivatives and their use as flavoring agents

The present invention primarily relates to 1H-pyrrole-2,4-dicarbonyl-derivatives of Formula (I) wherein R1, R2, R3, Z. Z' and J are as defined in the description, to mixtures thereof and to the use thereof as flavoring agents. The compounds in accordance with the present invention are suitable for producing, imparting, or intensifying an umami flavor. The invention further relates to flavoring mixtures, compositions for oral consumption as well as ready-to-eat, ready-to-use and semifinished products, comprising an effective amount of the compound of Formula (I) or of a mixture of compounds of Formula (I) and to specific methods for producing, imparting, modifying and/or intensifying specific flavor impressions.

New insights into the synthesis and characterization of 2-methoxy-3-alkylpyrazines and their deuterated isotopologues

A previously described synthetic route for preparation of 2-methoxy-3-alkylprazines (MPs) based on condensation of glyoxal with an α-amino acid amide, followed by methylation with iodomethane yields 3-alkyl-1-methyl-1H-pyrazin-2-ones (N-methyl derivatives), rather than the designated 2-methoxy-3-alkylpyrazines (O-methyl derivatives). Despite similar nuclear magnetic resonance and mass spectral properties, gas chromatographic (GC) retention indices differ significantly, indicating chemical difference. With the example of 3-sec-butyl-1-methyl-1H-pyrazin-2-one and its 3-sec-butyl-1-[2H3]methyl-1H-pyrazin-2-one isotopologue, the position of the methyl group introduced could be assigned unambiguously, using heteronuclear multiple bond correlation (HMBC) NMR experiments. For future characterization, the spectroscopic (NMR, EI+MS) as well as GC retention index data on two stationary phases of the most aroma relevant MPs and their deuterated isotopologues are summarized. Copyright