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CAS No.: | 294-93-9 |
---|---|
Name: | 12-Crown-4 |
Article Data: | 16 |
Molecular Structure: | |
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: | T+,Xn,Xi |
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 |
phenylacetylene
methyl trifluoromethanesulfonate
A
(1,4,7,10-tetraoxacyclododecane)
B
[W(CO)5(P(CHCMePh)(CH(SiMe3)2)(OPh))]
Conditions | Yield |
---|---|
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% |
ethylene glycol
1,2-bis(2-chloroethoxy)ethane
(1,4,7,10-tetraoxacyclododecane)
Conditions | Yield |
---|---|
With potassium hydroxide for 0.1h; microwave irradiation; | 37% |
Conditions | Yield |
---|---|
With cyanomethylenetributyl-phosphorane In benzene at 60℃; sealed vessel; | 30% |
With p-toluenesulfonyl chloride; lithium tert-butoxide In tert-butyl alcohol Heating; | 27% |
Conditions | Yield |
---|---|
With lithium hydride In dimethyl sulfoxide Heating; different basis as 'template' agents, other solvents; | 24% |
With lithium hydride In dimethyl sulfoxide Heating; | 24% |
Tetraethylene glycol
A
(1,4,7,10-tetraoxacyclododecane)
B
24-crown-8
C
<36>crown-12
D
48-Crown-16
Conditions | Yield |
---|---|
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% |
Tetraethylene glycol
diethylene glycol
A
(1,4,7,10-tetraoxacyclododecane)
B
18-crown-6 ether
C
24-crown-8
Conditions | Yield |
---|---|
With potassium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane at 60℃; | A n/a B 23% C 3% |
Conditions | Yield |
---|---|
With sodium hydroxide; p-toluenesulfonyl chloride In 1,4-dioxane at 20℃; | A 3% B 12% |
(1,4,7,10-tetraoxacyclododecane)
Conditions | Yield |
---|---|
In methanol at 25℃; Equilibrium constant; enthalpy-entropy compensation for the complexation reactions of crown ethers with alkaline cations; |
Conditions | Yield |
---|---|
In methanol at 25℃; Equilibrium constant; enthalpy-entropy compensation for the complexation reactions of crown ethers with alkaline cations; |
Conditions | Yield |
---|---|
Thermodynamic data; enthalpy and entropy changes for the complex dissociation reaction: ΔH0D, ΔS0D; |
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%.
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%.
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. |