Azetidine hydrochloride Chemical Properties

Melting point:

>300 °C(lit.)

Flash point:

152 °C

storage temp. 

Inert atmosphere,2-8°C

form 

powder to crystal

color 

White to Almost white

Water Solubility 

Soluble in water (103.8°C at 760 mmHg).

Sensitive 

Hygroscopic

InChI

InChI=1S/C3H7N.ClH/c1-2-4-3-1;/h4H,1-3H2;1H

InChIKey

HGQULGDOROIPJN-UHFFFAOYSA-N

SMILES

C1CNC1.Cl

CAS DataBase Reference

36520-39-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

RIDADR 

UN1325

WGK Germany 

3

HazardClass 

IRRITANT, HYGROSCOPIC

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

Azetidine hydrochloride Usage And Synthesis

Chemical Properties

White powder

Uses

Basic building block for synthesizing azetidines.1,2

Uses

Azetidine hydrochloride is a building block for azetidine synthesis and a pharmaceutical intermediate.

Uses

Azetidine hydrochloride is a four-membered ring nitrogen-containing heterocycle. Useful building block in the synthesis of polypeptides and other nitrogen containing compounds with potential biological properties.

General Description

Azetidine derivatives are an essential class of aza-heterocyclic compounds with various biological activities and have been widely used as building blocks in pharmacological research. Although azetidine has the simplest structure, it is only commercially available in small quantities and at a high price. In addition, this compound is hard to synthesize for several reasons, such as cyclization of the four-membered ring, stability of the ring, and low boiling point[1].

Synthesis

Under nitrogen protection, 1,1-dicyanoethylene (500 mg, 4.2 mmol, 1.0 eq.) was dissolved in 5.0 mL of toluene in a 50 mL round bottom flask. Polymethylhydrosiloxane (PMHS, 1.0 mL, 16.8 mmol, 4.0 eq.) and tetraisopropyl titanate (Ti(Oi-Pr)4, 1.3 mL, 4.3 mmol, 1.0 eq.) were added sequentially. The reaction mixture was heated at 100 °C for 24 h. The reaction solution was observed to change from colorless to dark purple. After completion of the reaction, it was cooled to room temperature, the dark purple solution was diluted with 30 mL of toluene and hydrolyzed by adding 1 M aqueous hydrochloric acid (15 mL, 3.6 eq.) for 4 hours until the color of the solution changed from dark purple to yellow. The crude product was concentrated under reduced pressure and the resulting solid was collected by filtration and washed with 60 mL of pentane. Subsequently, the solid was dissolved in chloroform and filtered through a Celite pad. Finally, the filtrate was concentrated under reduced pressure to give the hydrochloride form of the target compound 3p.

References

[1] Jian Sun, Qi Sun, S. Gong. “A Novel Strategy for the Synthesis of Azetidine.” Advanced Materials Research 6 1 (2013): 135–138.

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