Azetidine Chemical Properties

Melting point:

-70°C

Boiling point:

61-62 °C(lit.)

Density 

0.847 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.432(lit.)

Flash point:

−5 °F

storage temp. 

Store below +30°C.

pka

11.29(at 25℃)

form 

Liquid

color 

Clear colorless

Water Solubility 

miscible

Sensitive 

Moisture Sensitive/Air Sensitive

BRN 

102384

InChI

1S/C3H7N/c1-2-4-3-1/h4H,1-3H2

InChIKey

HONIICLYMWZJFZ-UHFFFAOYSA-N

SMILES

C1CNC1

CAS DataBase Reference

503-29-7(CAS DataBase Reference)

NIST Chemistry Reference

Azetidine(503-29-7)

EPA Substance Registry System

Azetidine (503-29-7)

Safety Information

Hazard Codes 

F,C

Risk Statements 

11-34

Safety Statements 

16-26-36/37/39-45

RIDADR 

UN 2733 3/PG 2

WGK Germany 

3

F 

2-10

TSCA 

TSCA listed

HazardClass 

3.1

PackingGroup 

I

HS Code 

29339990

Storage Class

3 - Flammable liquids

Hazard Classifications

Eye Dam. 1
Flam. Liq. 2
Skin Corr. 1B

MSDS

• Language:English Provider:Trimethylene imine
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Azetidine Usage And Synthesis

Chemical Properties

clear colorless liquid

Uses

suzuki reaction

Uses

Azetidine is involved in a high yielding palladium-catalyzed cross-coupling reaction with aryl bromides. Further, it is used in Ullmann type coupling reaction with iodonitroflourenes. In addition to this, it reacts with bis-(3-amino-propyl)-amine to prepare N,N'-bis-(3-amino-propyl)-propanediyldiamine using palladium as a catalyst.

Definition

ChEBI: Azetidine is a saturated organic heteromonocyclic parent, a member of azetidines and an azacycloalkane.

General Description

Phototransformations of azetidine radical cations in freonic matrices under the action of light with λ = 436nm has been investigated. The IR spectrum of azetidine in solid argon matrices has been measured.

Synthesis

To a 1-liter conical flask was added 4.0 mol of azetidine hydrochloride and 280 g of water, and the mixture was stirred at 20 degrees Celsius until the solid was dissolved, then to a 2-liter four-necked round-bottomed flask was added 230 g of water to which was added with stirring 459.4 g ( 6.96 mol ) of potassium hydroxide, and at the end of the exothermic addition of KOH, the solution was heated to 95 degrees Celsius and maintained at 95 degrees Celsius, an aqueous solution of azetidine hydrochloride ( 11 ) was added to the hot KOH /aqueous solution, controlling the rate of addition, and completing the addition within 3 hours. After completion of the reaction, the target product, heteroazetidine, is obtained by slowly distilling and purifying the target compound.

Purification Methods

Azetidine is a flammable, hygroscopic liquid smelling of ammonia, which absorbs CO2 from air and should be kept under Argon. Purify it by drying it over solid KOH and distilling it through a short Vigreux column (p 11) at atmospheric pressure (under Argon) and keeping the pot temperature below 210o. It is moisture sensitive. The hydrochloride M 93.6 has m > 300o and the hydroiodide has m 146.5o(from EtOH). The N-Me derivative has m 112o(from *C6H6/pet ether), and the Nphenylcarbamoyl derivative has m 189-190o(from EtOH). [Searles et al. J Am Chem Soc 7 8 4917 1956, Beilstein 20 H 2, 20 I 3, 20 II 3, 20 III/IV 53, 20/1 V 136.]

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