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294-93-9

Basic Information
CAS No.: 294-93-9
Name: 12-Crown-4
Article Data: 16
Molecular Structure:
Molecular Structure of 294-93-9 (12-Crown-4)
Formula: C8H16O4
Molecular Weight: 176.213
Synonyms: 12-Crown-4-ether;Ethylene oxide cyclic tetramer;1,4,7,10-Tetraoxacyclododecane;
EINECS: 206-036-5
Density: 0.995 g/cm3
Melting Point: 16 °C(lit.)
Boiling Point: 254.874 °C at 760 mmHg
Flash Point: 120.063 °C
Solubility: miscible with water
Appearance: clear colorless to slightly yellow liquid
Hazard Symbols: VeryT+,HarmfulXn,IrritantXi
Risk Codes: 26-36/37/38-20/21/22
Safety: 28-36/37-45-26
Transport Information: UN 2810
PSA: 36.92000
LogP: 0.06640
Synthetic route

[Li(12-crown-4)][W(CO)5(P(CH(SiMe3)2)(OPh))]

536-74-3

phenylacetylene

333-27-7

methyl trifluoromethanesulfonate

A

294-93-9

(1,4,7,10-tetraoxacyclododecane)

B

1416967-44-6

[W(CO)5(P(CHCMePh)(CH(SiMe3)2)(OPh))]

Conditions
ConditionsYield
In tetrahydrofuran byproducts: LiOTf; under Ar, soln. of phenylacetylene (1.0 mmol) added to W complex in THF at -78°C, after 0.5 h of stirring, phenylacetylene added, mixt. heated at reflux for 2 h, cooled to ambient temp., MeOTf added; volatiles evapd. in vac. (ca. 0.01 mbar), raw product purified by columnchromy. (SiO2, -20°C, petroleum ether/Et2O, 10:1), product obtai ned from 2nd fraction, detd. by 1H NMR, 13C NMR, 31P NMR, 29Si NMR, IR, MS;A n/a
B 62%
107-21-1

ethylene glycol

112-26-5

1,2-bis(2-chloroethoxy)ethane

294-93-9

(1,4,7,10-tetraoxacyclododecane)

Conditions
ConditionsYield
With potassium hydroxide for 0.1h; microwave irradiation;37%
112-60-7

Tetraethylene glycol

294-93-9

(1,4,7,10-tetraoxacyclododecane)

Conditions
ConditionsYield
With cyanomethylenetributyl-phosphorane In benzene at 60℃; sealed vessel;30%
With p-toluenesulfonyl chloride; lithium tert-butoxide In tert-butyl alcohol Heating;27%
111-44-4

3-oxa-1,5-dichloropentane

111-46-6

diethylene glycol

294-93-9

(1,4,7,10-tetraoxacyclododecane)

Conditions
ConditionsYield
With lithium hydride In dimethyl sulfoxide Heating; different basis as 'template' agents, other solvents;24%
With lithium hydride In dimethyl sulfoxide Heating;24%
112-60-7

Tetraethylene glycol

A

294-93-9

(1,4,7,10-tetraoxacyclododecane)

B

33089-37-1

24-crown-8

C

71092-59-6

<36>crown-12

D

71092-61-0

48-Crown-16

Conditions
ConditionsYield
With potassium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane at 65℃; Further byproducts given;A 1.4%
B 23%
C 11%
D 4.3%
112-60-7

Tetraethylene glycol

111-46-6

diethylene glycol

A

294-93-9

(1,4,7,10-tetraoxacyclododecane)

B

17455-13-9

18-crown-6 ether

C

33089-37-1

24-crown-8

Conditions
ConditionsYield
With potassium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane at 60℃;A n/a
B 23%
C 3%
112-60-7

Tetraethylene glycol

A

294-93-9

(1,4,7,10-tetraoxacyclododecane)

B

33089-37-1

24-crown-8

Conditions
ConditionsYield
With sodium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane at 20℃;A 3%
B 12%

C8H16O4*K(1+)

294-93-9

(1,4,7,10-tetraoxacyclododecane)

Conditions
ConditionsYield
In methanol at 25℃; Equilibrium constant; enthalpy-entropy compensation for the complexation reactions of crown ethers with alkaline cations;

2C8H16O4*K(1+)

A

294-93-9

(1,4,7,10-tetraoxacyclododecane)

B

C8H16O4*K(1+)

Conditions
ConditionsYield
In methanol at 25℃; Equilibrium constant; enthalpy-entropy compensation for the complexation reactions of crown ethers with alkaline cations;

C8H16O4*C3H9N*H(1+)

A

294-93-9

(1,4,7,10-tetraoxacyclododecane)

B

145384-53-8

trimethylammonium

Conditions
ConditionsYield
Thermodynamic data; enthalpy and entropy changes for the complex dissociation reaction: ΔH0D, ΔS0D;
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Specification

The 12-Crown-4, with the CAS registry number 294-93-9, is also known as Ethylene oxide cyclic tetramer. It belongs to the product categories of Crown Ethers; Functional Materials; Macrocycles for Host-Guest Chemistry. Its EINECS number is 206-036-5. This chemical's molecular formula is C8H16O4 and molecular weight is 176.21. What's more, its systematic name is 1,4,7,10-tetraoxacyclododecane. It is a crown ether and is used for complexing with lithium ion.

Physical properties of 12-Crown-4 are: (1)# of Rule of 5 Violations: 0; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 12.561; (5)ACD/KOC (pH 7.4): 12.561; (6)#H bond acceptors: 4; (7)#H bond donors: 0; (8)#Freely Rotating Bonds: 0; (9)Polar Surface Area: 36.92 Å2; (10)Index of Refraction: 1.404; (11)Molar Refractivity: 43.315 cm3; (12)Molar Volume: 177.057 cm3; (13)Polarizability: 17.171×10-24cm3; (14)Surface Tension: 31.295 dyne/cm; (15)Density: 0.995 g/cm3; (16)Flash Point: 120.063 °C; (17)Enthalpy of Vaporization: 47.243 kJ/mol; (18)Boiling Point: 254.874 °C at 760 mmHg; (19)Vapour Pressure: 0.027 mmHg at 25°C.

Preparation: this chemical can be prepared by ethane-1,2-diol and 1,2-bis-(2-chloro-ethoxy)-ethane by microwave irradiation. This reaction will need reagent aq. KOH with the reaction time of 6 min. The yield is about 37%.

12-Crown-4 can be prepared by ethane-1,2-diol and 1,2-bis-(2-chloro-ethoxy)-ethane by microwave irradiation

Uses of 12-Crown-4: it can be used to produce 2-phenylethynyl-1,4,7,10tetraoxa-cyclododecane by heating. It will need reagent AIBN and solvent acetonitrile with the reaction time of 3 hours. The yield is about 70%.

12-Crown-4 can be used to produce 2-phenylethynyl-1,4,7,10tetraoxa-cyclododecane by heating

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. It is harmful by inhalation, in contact with skin and if swallowed, and it is very toxic by inhalation. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing and gloves. After contact with skin, you must wash immediately with plenty of ... (to be specified by the manufacturer). In case of accident or if you feel unwell, you need seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: C1COCCOCCOCCO1
(2)Std. InChI: InChI=1S/C8H16O4/c1-2-10-5-6-12-8-7-11-4-3-9-1/h1-8H2
(3)Std. InChIKey: XQQZRZQVBFHBHL-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 1290mg/kg (1290mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Drug and Chemical Toxicology. Vol. 8, Pg. 451, 1985.
mouse LD50 oral 3150mg/kg (3150mg/kg) BEHAVIORAL: TREMOR

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Toxicology and Applied Pharmacology. Vol. 44, Pg. 263, 1978.
rabbit LD50 skin 4530uL/kg (4.53mL/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

BEHAVIORAL: ATAXIA
National Technical Information Service. Vol. OTS0536186,
rat LC50 inhalation 27ppm/4H (27ppm) PERIPHERAL NERVE AND SENSATION: SENSORY CHANGE INVOLVING PERIPHERAL NERVE

LIVER: OTHER CHANGES
National Technical Information Service. Vol. OTS0536186-1,
rat LD50 intraperitoneal 1550mg/kg (1550mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Drug and Chemical Toxicology. Vol. 8, Pg. 451, 1985.
rat LD50 oral 2830mg/kg (2830mg/kg) BEHAVIORAL: TREMOR Drug and Chemical Toxicology. Vol. 1, Pg. 339, 1978.