2-(2-Hydroxyethyl)pyridine

2-(2-Hydroxyethyl)pyridine Property

Melting point:

-8--7°C

Boiling point:

114-116 °C/9 mmHg (lit.)

Density 

1.093 g/mL at 25 °C (lit.)

vapor pressure 

1.16-14.1Pa at 25℃

refractive index 

n20/D 1.537(lit.)

Flash point:

199 °F

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Soluble in Chloroform (Slightly), Methanol (Slightly).

form 

Liquid

pka

14.49±0.10(Predicted)

color 

Clear yellow to brown

PH

8-9 (100g/l, H2O, 20℃)

Water Solubility 

soluble

Sensitive 

Hygroscopic

BRN 

111205

LogP

0.38

CAS DataBase Reference

103-74-2(CAS DataBase Reference)

NIST Chemistry Reference

2-Pyridineethanol(103-74-2)

EPA Substance Registry System

2-Pyridineethanol (103-74-2)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-24/25

WGK Germany 

2

RTECS 

UT2970450

F 

3

TSCA 

Yes

HS Code 

29333999

Hazardous Substances Data

103-74-2(Hazardous Substances Data)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H319Causes serious eye irritation

Precautionary statements

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.

P337+P313IF eye irritation persists: Get medical advice/attention.

2-(2-Hydroxyethyl)pyridine Chemical Properties,Usage,Production

Chemical Properties

clear yellow to brown liquid

Uses

2-Pyridineethanol is a metabolite of the anti-vertigo drug Betahistine (B324000).

Uses

2-(2-Hydroxyethyl)pyridine is a metabolite of the anti-vertigo drug Betahistine. It acts as a reagent for protection of the 5'-phosphate of nucleotides as 2-pyridylethyl (Pet) esters. It is used for carboxyl protection of amino acids. It is also used to cleave such groups as Boc and Fmoc, and also to hydrogenolysis. It was used to prepare mononuclear nickel(II) acetate.

General Description

2-(2-pyridyl)ethanol derivatives react with the aryl and alkenyl chlorides (palladium-catalyzed reactions) that result in the substitution of the chloro moieties with a 2-pyridylmethyl group.

Synthesis

The general procedure for the synthesis of 2-hydroxyethylpyridine from 2-chloromethylpyridine and formaldehyde is as follows: a two-necked Schlenk flask equipped with a magnetic stirring bar and a septum is heated under high vacuum with a hot air gun (ca. 400 °C) for 10 minutes. After cooling to room temperature, the flask was rinsed with argon (3 times). Zinc powder (654 mg, 2.0 equiv, 10.0 mmol) and THF (20 mL) were added sequentially. 1,2-dibromoethane (5 mol%) was added and the reaction mixture was heated to boiling. After cooling to room temperature, chlorotrimethylsilane (1 mol %) was added and the mixture was heated again to boiling. The flask was cooled to room temperature again, a solution of 2-chloromethylpyridine (633 mg, 5.0 mmol, 1 eq.) in THF (10 mL) was added and heated at 70 °C for 2 hours and then cooled to room temperature. Paraformaldehyde (450 mg, 3.0 eq, 15.0 mmol) was slowly added at room temperature and the flask was heated at 70 °C again for 6 hours. The reaction solution was cooled to room temperature and saturated NH4Cl solution was added. The phases were separated and the aqueous layer was extracted with ethyl acetate (100 mL). The organic layers were combined, washed sequentially with water (20 mL) and brine (10 mL) and dried over Na2SO4. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography using cyclohexane or cyclohexane/ethyl acetate as eluent to give 2-hydroxyethylpyridine (510 mg, 83%) as a colorless liquid.

References

[1] Synthetic Communications, 2017, vol. 47, # 10, p. 968 - 974