3-Acetylpyridine Chemical Properties

Melting point:

11-13 °C (lit.)

Boiling point:

220 °C (lit.)

Density 

1.102 g/mL at 25 °C (lit.)

vapor pressure 

0.3Pa at 20℃

FEMA 

3424 | 3-ACETYLPYRIDINE

refractive index 

n20/D 1.534(lit.)

Flash point:

302 °F

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Liquid

pka

pK1: 3.256(+1) (25°C)

Specific Gravity

1.102

color 

Clear colorless to yellow

PH

6.5-7.5 (H2O, 20℃)

Odor

at 1.00 % in dipropylene glycol. sweet nutty dry hawthorn phenolic woody popcorn

Odor Type

nutty

Water Solubility 

SOLUBLE IN HOT WATER

Merck 

14,6116

JECFA Number

1316

BRN 

107751

InChIKey

WEGYGNROSJDEIW-UHFFFAOYSA-N

LogP

0.34 at 13℃

CAS DataBase Reference

350-03-8(CAS DataBase Reference)

NIST Chemistry Reference

Ethanone, 1-(3-pyridinyl)-(350-03-8)

EPA Substance Registry System

Ethanone, 1-(3-pyridinyl)- (350-03-8)

Safety Information

Hazard Codes 

T,Xi,Xn

Risk Statements 

25-36/38-36/37/38-20/21/22

Safety Statements 

45-37/39-28A-26-36

RIDADR 

UN 2810 6.1/PG 3

WGK Germany 

3

RTECS 

OB5425000

F 

8-10

Hazard Note 

Irritant

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

II

HS Code 

29333999

Toxicity

LD50 orl-rat: 46 mg/kg JACTDZ 1,681,92

MSDS

• Language:English Provider:Methyl 3-pyridyl ketone
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-Acetylpyridine Usage And Synthesis

Identification

Description

A colorless liquid with sweet, nutty, popcorn-like aroma.

Regulatory Status

CoE: Used provisionally. Bev.: 2 ppm; Food: 3 ppm
FDA: n/a
FDA (other): n/a
JECFA: ADI: Acceptable. No safety concern at current levels of intake when used as a flavoring agent (2004).

Usage

Reported uses (ppm): (FEMA, 1994)

Natural occurrence

Reported found in roasted filberts, beer, brandy, coffee, malt and wheaten bread.

Aroma

Powerful, almost choking, Cigar-tobaccotype odor, which becomes pleasant only at extreme dilution, then also more typical tobacco-like. In certain types of flower bases, substitutes for flower absolutes, etc. this chemical can produce interesting and desirable effects, Lily, Jasmin, Tuberose, etc. are types of floral fragrances that may benefit from this effect.

Chemical Properties

A colorless liquid with sweet, nutty, popcorn-like aroma

Chemical Properties

clear colorless to yellow liquid

Occurrence

Reported found in roasted filberts, beer, brandy, coffee, malt and wheaten bread.

Uses

3-Acetylpyridine used as an intermediate for the synthesis of risedronate sodium, inhibitor of bone resorption. It is also used in perfumery.

Uses

Used in the fragrance industry and as an intermediate in the synthesis of a number of clinical drugs, including Imatinib, Mesylate, Metyrapone, Telithromycin, and Ridogrel. An analog of nicotinamide that competes for incorporation into NAD. It has been used to chemically lesion the inferior olive nucleus, thereby eliminating climbing fibers within the cerebellar cortex.

Production Methods

Produced from Ethyl nicotinate and Ethyl acetoacetate, in principle by hydrolysis of Aceto acetylpyridine.

Definition

It is a nicotinic acidantagonist.

Preparation

Dry distillation of calcium nicotinate with calcium acetate.

Safety Profile

Poison by ingestion. Moderately toxic by intraperitoneal routeMutation data reported. A flammable liquid. When heated to decomposition emits toxic fumes of NOx,. See also KETONES

Purification Methods

It is purified by dissolving in HCl, extracting with Et2O to remove the possible impurity of nicotinic acid, basified with NaOH and extracted with Et2O. The dried extract is filtered, evaporated and the residual oil is distilled. If the NMR spectrum indicates further impurities, then convert it to the phenylhydrazone (m 137o, yellow needles from EtOH). This is hydrolysed with HCl [Engler & Kiby Chem Ber 22 597 1889], the phenylhydrazine HCl is removed by filtration, NaNO2 is added, the solution is basified with aqueous NaOH and extracted with Et2O as before and distilled at atmospheric pressure to give 3-acetylpyridine as a colourless oil. Purification can also be achieved by shaking with 50% aqueous KOH, extracting with Et2O, drying the extract and distilling it at atmospheric pressure or in vacuo. [Kloetzel & Chubb J Am Chem Soc 79 4226 1957.] The hydrochloride has m 180-181o (from MeOH/EtOH), the picrate has m 133.8-134.8o (from H2O), and the phenylhydrazone has m 137o (129-130o)(needles, from EtOH) [Webb & Webb J Am Chem Soc 71 2285 1949]. The ketoxime has m 112o (from EtOH or *C6H6). [Strong & McElvain J Am Chem Soc 55 816 1933, Kolloff & Hunter J Am Chem Soc 63 490 1941, Beilstein 21/7 V 394.]

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