2-Propylpyrazine Chemical Properties

Boiling point:

65 °C (12 mmHg)

Density 

0.975

refractive index 

1.492-1.494

FEMA 

3961 | PROPYLPYRAZINE

Flash point:

56 °C

storage temp. 

Sealed in dry,Room Temperature

form 

clear liquid

pka

1.70±0.10(Predicted)

color 

Colorless to Light yellow

Specific Gravity

0.9700

Odor

at 0.10 % in dipropylene glycol. green vegetable nutty

Odor Type

green

JECFA Number

763

LogP

1.24

CAS DataBase Reference

18138-03-9(CAS DataBase Reference)

NIST Chemistry Reference

Pyrazine, 2-(n-propyl)-(18138-03-9)

EPA Substance Registry System

Pyrazine, propyl- (18138-03-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

37/38-41-36/37/38

Safety Statements 

24/25-39-26-36

RIDADR 

UN 1993C 3 / PGIII

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:ACROS

2-Propylpyrazine Usage And Synthesis

Application

2-Propylpyrazine is an organic synthesis intermediate and a pharmaceutical intermediate that can be used in laboratory research and development processes and chemical production processes.

Chemical Properties

clear very slightly yellow liquid

Chemical Properties

2-Propylpyrazine has a green, vegetable odor.

Occurrence

Reported found in roasted coffee beans.

Definition

ChEBI: Propylpyrazine is a member of pyrazines.

Aroma threshold values

Detection: 300 ppb

Synthesis

The general procedure for the synthesis of 2-propylpyrazine from 2-chloropyrazine and propylmagnesium chloride was as follows: first, 8.0 mL of 2-chloropyrazine, 1.58 g of iron acetylacetonate (Fe(acac)3), and 100 mL of tetrahydrofuran (THF) were added to a stirred round-bottomed flask. The mixture was stirred under nitrogen protection to form a red solution. The flask was cooled in an ice water bath for 10 minutes. Subsequently, 49 mL of n-propylmagnesium chloride was slowly added and the solution turned dark purple. After 1.5 hours of reaction, an additional 10 mL of n-propylmagnesium chloride was added over 10 minutes. after 20 minutes, 5 mL of n-propylmagnesium chloride continued to be added. After stirring for about 30 minutes, 22 mL of saturated aqueous ammonium chloride (NH4Cl) was added over 7 minutes. After an additional 7 mL of NH4Cl was added, stirring was stopped and the mixture was allowed to stand at room temperature under nitrogen protection overnight. After addition of 125 mL of ethyl acetate (EtOAc) and 450 mL of water, the mixture was filtered through a polypropylene filter and transferred to a partition funnel. The organic and aqueous phases were separated and the aqueous phase was extracted twice with 125 mL of EtOAc. The organic phase was combined and filtered through Celite. Subsequently, it was concentrated using a rotary evaporator at 200 mbar and 40 °C. The fractions were purified by short-range distillation and Vigreux column distillation (200 mbar, 90-110 °C) to give 9.0 g (82.4% yield) of 2-n-propylpyrazine. The purity of the final product was confirmed by HPLC analysis using an Elipse XDB-C8 column (4.6 × 150 mm, 5 μm) with a mobile phase of 60:40 acetonitrile/water (containing 1% trifluoroacetic acid) at a flow rate of 1 mL/min, a column temperature of 35 °C, and a retention time of 3.0 minutes.

References

[1] Patent: WO2010/107969, 2010, A1. Location in patent: Page/Page column 6-7
[2] Journal of the American Chemical Society, 1992, vol. 114, # 13, p. 5269 - 5280
[3] Organic Process Research and Development, 2015, vol. 19, # 7, p. 806 - 811

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