12-Crown-4 Chemical Properties

Melting point:

16 °C (lit.)

Boiling point:

61-70 °C/0.5 mmHg (lit.)

Density 

1.089 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.463(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

Liquid After Melting

Specific Gravity

1.115 (20℃)

color 

Clear colorless to slightly yellow

Water Solubility 

MISCIBLE

Sensitive 

Air Sensitive

BRN 

1363064

CAS DataBase Reference

294-93-9(CAS DataBase Reference)

NIST Chemistry Reference

12-Crown-4(294-93-9)

EPA Substance Registry System

1,4,7,10-Tetraoxacyclododecane (294-93-9)

Safety Information

Hazard Codes 

T+,Xn,Xi

Risk Statements 

26-36/37/38-20/21/22

Safety Statements 

28-36/37-45-36-26

RIDADR 

UN 2810

WGK Germany 

3

RTECS 

XF0550000

F 

3-9-23

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29329995

Toxicity

LD50 oral in rat: 2830mg/kg

MSDS

• Language:English Provider:1,4,7,10-Tetraoxacyclododecane
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

12-Crown-4 Usage And Synthesis

Chemical Properties

clear colorless to slightly yellow liquid after

Uses

It serves as an aprotic "solvent" for alkali metals, the sodium solution is a strong reducing agent.

Uses

12-Crown-4 can be used as:

• A promoter in the synthesis of poly(diethylsiloxane) (PDES) from monomer hexaethylcyclotrisiloxane using NaOH as a catalyst via anionic ring-opening polymerization.
• As an additive in the preparation of triarylmethane derivatives by palladium-catalyzed cross coupling reaction of aryl bromides with diarylmethane derivatives.
• A phase transfer catalyst in organic synthesis.

Definition

ChEBI: A crown ether that is cyclododecane in which the carbon atoms at positions 1, 4, 7 and 10 have been replaced by oxygen atoms.

Synthesis Reference(s)

Tetrahedron Letters, 15, p. 4029, 1974 DOI: 10.1016/S0040-4039(01)92075-1

General Description

12-Crown-4 is a crown ether generally used as a ligand in coordination chemistry. It is also known as lithium ionophore because of its strong chelating property specific to lithium cation.

Purification Methods

The distilled crude product has to be recrystallised from pentane at -20o to remove acyclic material. It is then dried over P2O5. It complexes Li. [Anet et al. Acta Chem Scand 27 3395 1973, Beilstein 19/11 V 334.]

12-Crown-4(294-93-9)Related Product Information

• 1,7-DIAZA-12-CROWN-4,4,10-DIAZA-12-CROWN 4-ETHER
• BIS[(12-CROWN-4)METHYL] DODECYLMETHYLMALONATE
• 2-(HYDROXYMETHYL)-12-CROWN 4-ETHER
• Tetraaza 12-crown-4
• 1-AZA-12-CROWN 4-ETHER,1-AZA-12-CROWN-4,AZA-12-CROWN-4,aza-12-crown-499.5+%
• BENZO-12-CROWN-4,BENZO-12-CROWN 4-ETHER,Benzo-12-crown-4, 99+%,BENZO-12-CROWN-4 98+%
• 1-aza-12-crown-5
• TETRAAZA-12-CROWN-4-1,4,7,10-TETRAACETIC ACID,TETRAAZA-12-CROWN-4 TETRAACETIC ACID AMMONIUM SALT (SEE 2923)
• TETRAAZA-12-CROWN-4 TETRAHYDROCHLORIDE
• CYCLODODECANE
• N-METHYLAZA-12-CROWN-4
• 4-TERT-BUTYL-CALIX[4]ARENE-CROWN-4-COMPLEX
• 1-BENZYL-1-AZA-12-CROWN-4,N-BENZYLAZA-12-CROWN-4
• TETRAAZA-12-CROWN-4 TETRAHYDROGENSULFATE
• 12-Crown-4
• Cyclohexyl-12-crown-4
• Tetraaza 12-crown-4-tetraacetic acid derivative
• BIS[(12-CROWN-4)METHYL] 2,2-DIDODECYLMALONATE