| Identification | More | [Name]
12-Crown-4 | [CAS]
294-93-9 | [Synonyms]
12-CROWN-4
12-CROWN 4-ETHER
1,4,7,10-TETRAOXACYCLODODECANE
1,4,7,10-TETRAOXYCYCLODODECANE
CROWN ETHER/12-CROWN-4
LITHIUM IONOPHORE V
Eoct
Ethylene oxide cyclic tetramer
Crown
1,4,7,10-Tetraoxacyclododecane, 12-Crown-4 | [EINECS(EC#)]
206-036-5 | [Molecular Formula]
C8H16O4 | [MDL Number]
MFCD00005103 | [Molecular Weight]
176.21 | [MOL File]
294-93-9.mol |
| Chemical Properties | Back Directory | [Appearance]
clear colorless to slightly yellow liquid after | [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.)
| [Fp ]
>230 °F
| [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [form ]
Liquid After Melting | [color ]
Clear colorless to slightly yellow | [Specific Gravity]
1.115 (20℃) | [Water Solubility ]
MISCIBLE | [Sensitive ]
Air Sensitive | [BRN ]
1363064 | [InChI]
1S/C8H16O4/c1-2-10-5-6-12-8-7-11-4-3-9-1/h1-8H2 | [InChIKey]
XQQZRZQVBFHBHL-UHFFFAOYSA-N | [SMILES]
C1COCCOCCOCCO1 | [CAS DataBase Reference]
294-93-9(CAS DataBase Reference) | [NIST Chemistry Reference]
12-Crown-4(294-93-9) | [EPA Substance Registry System]
294-93-9(EPA Substance) |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS06 | [Signal word ]
Danger | [Hazard statements ]
H330 | [Precautionary statements ]
P304+P340+P310 | [Hazard Codes ]
T+,Xn,Xi | [Risk Statements ]
R26:Very Toxic by inhalation.
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S36/37:Wear suitable protective clothing and gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [RIDADR ]
UN 2810 | [WGK Germany ]
3
| [RTECS ]
XF0550000
| [F ]
3-9-23 | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29329995 | [Storage Class]
6.1A - Combustible acute toxic Cat. 1 and 2
very toxic hazardous materials | [Hazard Classifications]
Acute Tox. 1 Inhalation | [Toxicity]
LD50 oral in rat: 2830mg/kg |
| Hazard Information | Back Directory | [Chemical Properties]
clear colorless to slightly yellow liquid after | [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.
| [Uses]
An aprotic "solvent" for alkali metals, the sodium solution is a strong reducing agent | [Uses]
It serves as an aprotic "solvent" for alkali metals, the sodium solution is a strong reducing agent. | [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.] |
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