Azetidine

Structural formula
General
Surname	Azetidine
other names	Trimethyleneimine Azacyclobutane
Molecular formula	C 3 H 7 N
Brief description	colorless liquid with a characteristic odor
External identifiers / databases
CAS number 503-29-7 EC number 207-963-8 ECHA InfoCard 100.007.240 PubChem 10422 ChemSpider 9993 Wikidata Q425376
properties
Molar mass	57.10 g mol −1
Physical state	liquid
density	0.85 g cm −3
Melting point	−83 ° C
boiling point	61-62 ° C
Vapor pressure	176 h Pa (19 ° C)
solubility	soluble in water
Refractive index	1.4287 (25 ° C)
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 225-314 P: 210-280-305 + 351 + 338-310
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Azetidine , also called trimethyleneimine , is the simplest nitrogen-containing saturated four-membered heterocycle . It forms the basic structure of the group of azetidines .

presentation

Azetidine can be obtained from the thermal reaction of 1,3-diaminopropane with hydrochloric acid .

${\displaystyle \mathrm {NH_{2}(CH_{2})_{3}NH_{2}\ {\xrightarrow {HCl}}\ C_{3}H_{7}N+\ NH_{3}} }$

properties

Azetidine is a colorless liquid with a boiling point of 61–62 ° C. It is a heterocyclic nitrogen base .

Reactions

The azetidine ring can be opened by nucleophiles . This enables the synthesis of terminal amines .

For example, react ethylenediamine with azetidine on palladium - catalyst under ring opening to give a triamine.

Web links

Commons : Azetidine  - Collection of pictures, videos, and audio files

Individual evidence

1. ↑ ^{a b c d e} data sheet azetidine (PDF) from Merck , accessed on August 20, 2015.
2. ↑ GM Day, WD S Motherwell, HL Ammon, SXM Boerrierter, RG della Valle, E. Venuti, A. Dzyabchenko, JD Dunitz, B. Schweizer, BP van Eijck, P. Erk in: Acta Crystallogr. Sect. B 2005, 61, 5, 511-527.
3. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-30.
4. ↑ ^{a b} Azetidine data sheet from Sigma-Aldrich , accessed on March 9, 2011 ( PDF ).
5. ^ Ladenburg, Sieber in: Chem. Ber. 1890, 23, 2727.
6. ↑ S.-I. Murahashi, N. Yoshimura, T. Tsumiyama, T. Kojima in: J. Am. Chem. Soc. 1983, 105, 15, 5002-5011.