2-Pentylpyridine

2-Pentylpyridine Property

Boiling point:

102-107 °C (lit.)

Density 

0.897 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.488(lit.)

FEMA 

3383 | 2-PENTYLPYRIDINE

Flash point:

175 °F

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

clear liquid

pka

6.01±0.10(Predicted)

Specific Gravity

0.902

color 

Colorless to Light yellow

Odor

at 0.10 % in propylene glycol. fatty tallow green pepper mushroom herbal

Odor Type

fatty

biological source

synthetic

JECFA Number

1313

BRN 

2772

LogP

3.31

CAS DataBase Reference

2294-76-0(CAS DataBase Reference)

NIST Chemistry Reference

Pyridine, 2-pentyl-(2294-76-0)

EPA Substance Registry System

2-Pentylpyridine (2294-76-0)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29333990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H227Combustible liquid

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

2-Pentylpyridine Chemical Properties,Usage,Production

Chemical Properties

2-Pentylpyridine has a tallowy-like odor.

Occurrence

Reported as occurring in shallow-fried beef and as a steam-volatile component in roasted Spanish peanut. Also reported found in bell pepper, black sesame seeds, roast turkey, fried chicken, fried beef, cooked beef, mutton, lamb fat, roasted filberts, toasted oats and coriander seed.

Uses

flavors and fragrances

Definition

ChEBI: 2-Pentylpyridine is a member of pyridines.

Preparation

By alkylation of 2-pycollyl lithium; by hydrogenation of 2-pentenyl pyridine.

Aroma threshold values

Detection: 0.6 ppb. Aroma characteristics at 0.1%: strong fresh green vegetative, peppery, mushroom, herbal and oily.

Taste threshold values

Taste characteristics at 1 ppm: green pepper vegetative, mushroom-like, musty, oily, meaty and MSG-like.

Synthesis

GENERAL STEPS: A THF solution (3 mL) of MnCl2-(THF)1.6 (3 mol%, 3 mg, 0.012 mmol) was added to a 20 mL scintillation vial in an inert atmosphere glove box. Subsequently, 2-chloropyridine (0.41 mmol, 1 eq.) was added as an electrophilic reagent, as well as the internal standard homotrimethylbenzene (0.41 mmol, 1 eq.). After stirring for 5 minutes at room temperature, 1-pentylmagnesium chloride Grignard reagent solution (1.2-2.6 eq.) was slowly added dropwise and the reaction continued to be stirred at room temperature. Upon completion of the reaction, the mixture was removed from the glove box and the reaction was quenched with saturated K2CO3 solution (3 mL) and EtOAc (3 mL). The organic layer was separated and the aqueous phase was further extracted with EtOAc (3 x 3 mL). The combined organic phases were dried with MgSO4, filtered and concentrated. The crude product was purified by silica gel column chromatography to afford the target product 2-pentylpyridine.

Purification Methods

Dry it with NaOH for several days, then distil it from CaO under reduced pressure, taking the middle fraction and redistilling it. The picrate has m 72-72.8o (from EtOH). [Beilstein 20 III/IV 2835.] 3-n-Pentylpyridine, purified as the 2-isomer, has b 110-112o/20mm, 224-226o/748mm, and the picrate has m 79.5-80o(from EtOH). [Beilstein 20 III/IV 2835.]

References

[1] Synlett, 2018, vol. 29, # 13, p. 1700 - 1706