12-Crown-4 supplier | CasNO.294-93-9

Name
12-Crown-4
EINECS 206-036-5
CAS No. 294-93-9
Article Data16
CAS DataBase
Density 0.995 g/cm³
Solubility miscible with water
Melting Point 16 °C(lit.)
Formula C₈H₁₆O₄
Boiling Point 254.874 °C at 760 mmHg
Molecular Weight 176.213
Flash Point 120.063 °C
Transport Information UN 2810
Appearance clear colorless to slightly yellow liquid
Safety 28-36/37-45-26
Risk Codes 26-36/37/38-20/21/22
Molecular Structure
Hazard Symbols T+,Xn,Xi
Synonyms 12-Crown-4-ether;Ethylene oxide cyclic tetramer;1,4,7,10-Tetraoxacyclododecane;
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

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%

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%

...Expand

: 107-21-1
ethylene glycol

: 112-26-5
1,2-bis(2-chloroethoxy)ethane

: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

Conditions

Conditions	Yield
With potassium hydroxide for 0.1h; microwave irradiation;	37%

: 112-60-7
Tetraethylene glycol

: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

Conditions

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%

: 111-44-4
3-oxa-1,5-dichloropentane

: 111-46-6
diethylene glycol

: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

Conditions

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%

: 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

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%

...Expand

: 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

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

...Expand

: 112-60-7
Tetraethylene glycol

A: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

B: 33089-37-1
24-crown-8

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

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

: C8H16O4*C6H13N*H(1+)

A: 29384-28-9
cyclohexyl-ammonium cation

B: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

Conditions

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

: C8H16O4*C5H5N*H(1+)

A: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

B: 16969-45-2
pyridin-1-ium

Conditions

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

: C8H16O4*C4H4N2*H(1+)

A: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

B: 17009-97-1
1,2-diazineH+

Conditions

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

: 12-Crown-4 lithium perchlorate

: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

Conditions

Conditions	Yield
In acetone Equilibrium constant; various solvents (MeNO2, MeCN, propylene carbonate, MeOH, pyridine), complex formation between crown ethers and lithim ion, effect of solvent of the stability of complexes, 7Li NMR study;

: C8H16O4*2ClO4(1-)*2Li(1+)

: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

Conditions

Conditions	Yield
In nitromethane Equilibrium constant; various solvents (MeCN, propylene carbonate, Me2CO, MeOH, pyridine), complex formation between crown ethers and lithim ion, effect of solvent of the stability of complexes, formation of 1:1 and 1:2 complexes, 7Li NMR study;

: 1,4,7,10-Tetraoxa-cyclododecane; compound with GENERIC INORGANIC NEUTRAL COMPONENT

: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

Conditions

Conditions	Yield
With Iodine monochloride In benzene at 24.9℃; Equilibrium constant;

: C8H16O4*C10H15(1-)*C24BF20(1-)*Si(2+)

A: 123-91-1
1,4-dioxane

B: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

Conditions

Conditions	Yield
In dichloromethane-d2 for 480h;

: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

: Lu(N(SiMe3)2)3

: 18027-10-6
sodium trimethylsilanolate

: [Na((CH2CH2O)4)2](1+)*[Lu(N(Si(CH3)3)2)3(OSi(CH3)3)](1-)=[Na((CH2CH2O)4)2][Lu(N(Si(CH3)3)2)3(OSi(CH3)3)]

Conditions

Conditions	Yield
In hexane dry atm.; molar ratio 1:1:2, stirring (room temp., 6 h); filtn., washing (n-hexane), drying (vac.); elem. anal.;	100%

...Expand

: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

: 18027-10-6
sodium trimethylsilanolate

: tris(bis(trimethylsilyl)amido)europium(III)

: [Na((CH2CH2O)4)2](1+)*[Eu(N(Si(CH3)3)2)3(OSi(CH3)3)](1-)=[Na((CH2CH2O)4)2][Eu(N(Si(CH3)3)2)3(OSi(CH3)3)]

Conditions

Conditions	Yield
In hexane dry atm.; molar ratio 1:1:2, stirring (room temp., 6 h); filtn., washing (n-hexane), drying (vac.); elem. anal.;	100%

...Expand

: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

: tris(bis(trimethylsilyl)amido)ytterbium(III)

: 18027-10-6
sodium trimethylsilanolate

: [Na((CH2CH2O)4)2](1+)*[Yb(N(Si(CH3)3)2)3(OSi(CH3)3)](1-)=[Na((CH2CH2O)4)2][Yb(N(Si(CH3)3)2)3(OSi(CH3)3)]

Conditions

Conditions	Yield
In hexane dry atm.; molar ratio 1:1:2, stirring (room temp., 6 h); filtn., washing (n-hexane), drying (vac.); elem. anal.;	100%

...Expand

: tris(bis(trimethylsilyl)amido)samarium(III)

: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

: 18027-10-6
sodium trimethylsilanolate

: [Na((CH2CH2O)4)2](1+)*[Sm(N(Si(CH3)3)2)3(OSi(CH3)3)](1-)=[Na((CH2CH2O)4)2][Sm(N(Si(CH3)3)2)3(OSi(CH3)3)]

Conditions

Conditions	Yield
In hexane dry atm.; molar ratio 1:1:2, stirring (room temp., 6 h); filtn., washing (n-hexane), drying (vac.); elem. anal.;	100%

...Expand

: 109-99-9
tetrahydrofuran

: 109-72-8, 29786-93-4
n-butyllithium

: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

: C12H20B10

: C12H19B10(1-)*Li(1+)*2C4H8O*2C8H16O4

Conditions

Conditions	Yield
Stage #1: tetrahydrofuran; n-butyllithium; C12H20B10 Stage #2: (1,4,7,10-tetraoxacyclododecane) In tetrahydrofuran	100%

...Expand

: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

: [Li(THF)3][UO2(N(SiHMe2)tBu)3]

: [Li(12-crown-4)2][UO2(N(SiHMe2)tBu)3]

Conditions

Conditions	Yield
In tetrahydrofuran for 1h;	100%

: 7787-47-5
beryllium(II) chloride

: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

: [(BeCl)([12]crown-4)]Cl

Conditions

Conditions	Yield
In dichloromethane at 20℃; Inert atmosphere; Schlenk technique;	100%

: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

: C36H30Be3

: 591-51-5
phenyllithium

: C16H32Li2O8(2+)*2C18H15Be(1-)

Conditions

Conditions	Yield
Stage #1: (1,4,7,10-tetraoxacyclododecane); C36H30Be3; phenyllithium In benzene-d6 Stage #2: In benzene-d6 at 80℃;	100%

...Expand

: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

: C36H30Be3

: C14H21BeO4(1+)*C18H15Be(1-)

Conditions

Conditions	Yield
Stage #1: (1,4,7,10-tetraoxacyclododecane); C36H30Be3 In benzene-d6 Stage #2: In benzene-d6 Heating;	100%

: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

: {Na}{(4,5-bis(diisopropylphosphino)-2,7,9,9-tetramethyl-9H-acridin-10-ide)Ni(CO)}

: {Na(12-crown-4)2}{(4,5-bis(diisopropylphosphino)-2,7,9,9-tetramethyl-9H-acridin-10-ide)Ni(CO)}

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;	99%

: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

: 851576-85-7
[W(carbonyl)5([bis(trimethylsilyl)methyl]cyanophosphane)]

: 594-19-4
tert.-butyl lithium

: 947333-61-1
[(OC)5WP(CH(SiMe3)2)CNLi(12-crown-4)]

Conditions

Conditions	Yield
In diethyl ether; hexane under Ar; soln. of t-BuLi in n-hexane added dropwise at -80°C to stirred soln. of W complex in Et2O and 12-crown-4; warmed slowly to roomtemp. for 3.5 h; solvent removed under vac.; washed with Et2O and n-pentane; dried under reduced pressure; elem. anal.;	98.3%

...Expand

: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

: 1277179-18-6
(Si(o-C6H4PiPr2)3)Fe[(CO)Na(THF)3]

: [(Na(12-crown-4)2][(Si(o-C6H4PiPr2)3)Fe(CO)]

Conditions

Conditions	Yield
In tetrahydrofuran (Schlenk or glovebox, N2) the soln. of 12-crown-4 in THF was added dropwise to a soln. of complex in THF, stirred for 30 min at room temp.; filtered, volatiles were removed under vac., the solid was washed with pentane; elem. anal.;	98%

: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

: (4,5-bis(diisopropylphosphino)-2,7,9,9-tetramethyl-9H-acridin-10-ide)Ni-μ-CO2-Na*THF

: {Na(12-crown-4)2}{(4,5-bis(diisopropylphosphino)-2,7,9,9-tetramethyl-9H-acridin-10-ide)Ni(CO2)}

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere;	98%

: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

: C42H51CrLi2O3

: C30H25Cr(2-)*2C12H24LiO5(1+)

Conditions

Conditions	Yield
In tetrahydrofuran at 0℃; Solvent; Inert atmosphere; Schlenk technique;	98%

: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

: [Na(tetrahydrofuran)x][(Mo(N[i-Pr](3,5-C6H3Me2)3)2N]

: 7727-37-9
nitrogen

A: 394246-98-1
[Mo(N[i-Pr](3,5-C6H3Me2)3N]

B: [Na(12-crown-4)2][(Mo(N[i-Pr](3,5-C6H3Me2)3)N2]

Conditions

Conditions	Yield
In not given at 25°C? 1 atm and in the presence of crown ether (2 equiv. per Na);	A n/a B 97%

...Expand

: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

: C24H48LiP2Si4(1-)*4C4H8O*Li(1+)

: C12H24PSi2(1-)*2C8H16O4*Li(1+)

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; Glovebox;	97%

: tin(II) trifluoromethanesulfonate

: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

: bis([12]crown-4)tin(II) triflate

Conditions

Conditions	Yield
In tetrahydrofuran standard inert-atmosphere techniques; soln. of (12)crown-4 (0.943 mmol) added to soln. of Sn(OTf)2 (0.479 mmol), stiired for 2 h; solvent removed (in vac.), washed with pentane; elem. anal.;	96%

: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

: Ba((N,N-dimethylamino)diboranato)2(diethyl ether)(x)

: bis[(N,N-dimethylamino)diboranato](12-crown-4) barium(II)

Conditions

Conditions	Yield
In diethyl ether under Ar atm. using Schlenk techniques; to soln. of Ba complex in Et2O was added Lewis base; mixt. stirred overnight; solid filtered; washed (pentane); dried under vac.; elem. anal.;	96%

: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

: 40949-94-8
potassium hexamethylsilazane

: C28H68K2N2O8Si4

Conditions

Conditions	Yield
In toluene Inert atmosphere; Schlenk technique;	96%

: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

: C36H54FeGaN2P3(1-)*C12H24NaO3(1+)

: C36H54FeGaN2P3(1-)*C16H32NaO8(1+)

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 2h;	96%

: 3262-89-3
triphenylboroxine

: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

: 7732-18-5
water

: lithium pyrazolide

: Li[Li(tetrahydrofuran)(phenyl(pyrazolyl)B(μ-O)(μ-OB(phenyl)O)B(pyrazolyl)phenyl)]*(12-crown-4)*2H2O

Conditions

Conditions	Yield
In tetrahydrofuran (N2); using Schlenk techniques; stirring of mixt. of Li(pz) (2 equiv.), Ph3B3O3 (1 equiv.) and 12-crown-4 (2 equiv.) in THF at room temp. for 30min; addn. of hexane; cooling to -5°C overnight; crystn.; rinsing withhexane; drying under reduced pressure;	95%

...Expand

: 109-99-9
tetrahydrofuran

: 3262-89-3
triphenylboroxine

: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

: lithium pyrazolide

: C8H16LiO4(1+)*C28H29B3LiN4O4(1-)

Conditions

Conditions	Yield
for 0.5h;	95%

...Expand

: 7782-49-2
selenium

: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

: C44H69ClLiLuO3Si2

: 630-19-3
pivalaldehyde

: C37H53ClLuOSeSi2(1-)*Li(1+)*2C8H16O4

Conditions

Conditions	Yield
Stage #1: C44H69ClLiLuO3Si2; pivalaldehyde In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; Stage #2: selenium In tetrahydrofuran Inert atmosphere; Stage #3: (1,4,7,10-tetraoxacyclododecane) In tetrahydrofuran for 1h; Inert atmosphere;	95%

...Expand

: 294-93-9
(1,4,7,10-tetraoxacyclododecane)

: 174090-55-2
uranium(III) tris(1,3-bis-(trimethylsilyl)cyclopentadienyl)

: 7440-23-5
sodium

: [Na(12-crown-4)2][(C5H3(SiMe3)2)3U]

Conditions

Conditions	Yield
In tetrahydrofuran for 0.5h; Glovebox; Inert atmosphere; Schlenk technique;	95%

...Expand

12-Crown-4 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.

Product Name

12-Crown-4

Synthetic route

12-Crown-4 Specification

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