Product Name

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  • Name

    Diethyl ether

  • EINECS 200-467-2
  • CAS No. 60-29-7
  • Article Data681
  • CAS DataBase
  • Density 0.734 g/cm3
  • Solubility 69 g/L (20 °C) in water
  • Melting Point -116 °C
  • Formula C4H10O
  • Boiling Point 33.177 °C at 760 mmHg
  • Molecular Weight 74.1228
  • Flash Point -45 °C
  • Transport Information UN 1155 3/PG 1
  • Appearance Colourless liquid
  • Safety 9-16-29-33-45-36/37
  • Risk Codes 12-19-22-66-67-39/23/24/25-23/24/25
  • Molecular Structure Molecular Structure of 60-29-7 (Diethyl ether)
  • Hazard Symbols HighlyF+, HarmfulXn, ToxicT
  • Synonyms Ether(6CI);Ethyl ether (8CI);1,1'-Oxybisethane;3-Oxapentane;Anaesthetic ether;Anesthesia ether;Anesthetic ether;Diethyl oxide;Ethoxyethane;Ethyl oxide;NSC 100036;Pronarcol;Sulfuric ether;Ethyl ether;Ethane, 1,1'-oxybis-;
  • PSA 9.23000
  • LogP 1.04280

Synthetic route

ethanol
64-17-5

ethanol

diethyl ether
60-29-7

diethyl ether

Conditions
ConditionsYield
With reduced Sn/hydrotalcite catalyst at 250℃; under 25502.6 Torr; Catalytic behavior; Reagent/catalyst; Temperature; Pressure;99%
With SA5 at 199.84℃; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere;2.6%
With sulfuric acid at 130 - 140℃; Darstellung im grossen;
ethanol
64-17-5

ethanol

A

diethyl ether
60-29-7

diethyl ether

B

ethene
74-85-1

ethene

Conditions
ConditionsYield
With alumina at 449.84℃; Catalytic behavior; Reagent/catalyst; Temperature; Inert atmosphere; Overall yield = 100 %;A 0.1%
B 98.9%
C2I2O2Rh(1-)*C8H20N(1+); tetraethylammonium iodide; hydrogen iodide In water at 110℃; Product distribution / selectivity; Inert atmosphere; Autoclave;A 10%
B 50%
1-methyl-3-(propyl-3-sulfonyl)imidazolium trifluoromethanesulfonate; CF3O3S(1-)*CHF3O3S*C7H13N2O3S(1+) at 240 - 260℃; for 4h; Product distribution / selectivity;A n/a
B 12%
triethyloxonium tris(pentafluoroethyl)trifluorophosphate
945614-32-4

triethyloxonium tris(pentafluoroethyl)trifluorophosphate

1-ethyl-3-methyl-1H-imidazol-3-ium chloride
65039-09-0

1-ethyl-3-methyl-1H-imidazol-3-ium chloride

A

1-ethyl-3-methyl-imidazolium tris(pentafluoroethyl)trifluorophosphate
377739-43-0

1-ethyl-3-methyl-imidazolium tris(pentafluoroethyl)trifluorophosphate

B

diethyl ether
60-29-7

diethyl ether

C

chloroethane
75-00-3

chloroethane

Conditions
ConditionsYield
at 80℃; for 3h; Product distribution / selectivity;A 98.9%
B n/a
C n/a
triethyloxonium tris(pentafluoroethyl)trifluorophosphate
945614-32-4

triethyloxonium tris(pentafluoroethyl)trifluorophosphate

N,N,N',N',N'',N''-hexamethylguanidinium chloride
30388-20-6

N,N,N',N',N'',N''-hexamethylguanidinium chloride

A

hexamethylguanidinium tris(pentafluoroethyl)trifluorophosphate

hexamethylguanidinium tris(pentafluoroethyl)trifluorophosphate

B

diethyl ether
60-29-7

diethyl ether

C

chloroethane
75-00-3

chloroethane

Conditions
ConditionsYield
at 80℃; for 3h;A 98.9%
B n/a
C n/a
triethyloxonium tris(pentafluoroethyl)trifluorophosphate
945614-32-4

triethyloxonium tris(pentafluoroethyl)trifluorophosphate

1-ethyl-3-methylimidazolium hexafluorophosphate
155371-19-0

1-ethyl-3-methylimidazolium hexafluorophosphate

A

1-ethyl-3-methyl-imidazolium tris(pentafluoroethyl)trifluorophosphate
377739-43-0

1-ethyl-3-methyl-imidazolium tris(pentafluoroethyl)trifluorophosphate

B

diethyl ether
60-29-7

diethyl ether

C

1-fluoroethane
353-36-6

1-fluoroethane

D

phosphorus pentafluoride
7647-19-0, 874483-74-6

phosphorus pentafluoride

Conditions
ConditionsYield
at 100℃; for 10h; Product distribution / selectivity;A 98.7%
B n/a
C n/a
D n/a
triethyloxonium bis(trifluoromethylsulfonyl)imide
945614-34-6

triethyloxonium bis(trifluoromethylsulfonyl)imide

1-cyano-4-N,N-dimethylaminopyridinium bromide
59016-54-5

1-cyano-4-N,N-dimethylaminopyridinium bromide

A

ethyl bromide
74-96-4

ethyl bromide

B

diethyl ether
60-29-7

diethyl ether

C

1-cyano-4-dimethylaminopyridinium bis(trifluoromethylsulfonyl)imide
945614-38-0

1-cyano-4-dimethylaminopyridinium bis(trifluoromethylsulfonyl)imide

Conditions
ConditionsYield
at 60℃; for 5h;A n/a
B n/a
C 98.2%
triethyloxonium bis(trifluoromethylsulfonyl)imide
945614-34-6

triethyloxonium bis(trifluoromethylsulfonyl)imide

1-ethyl-3-methyl-1H-imidazol-3-ium chloride
65039-09-0

1-ethyl-3-methyl-1H-imidazol-3-ium chloride

A

diethyl ether
60-29-7

diethyl ether

B

chloroethane
75-00-3

chloroethane

C

1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide
174899-82-2

1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide

Conditions
ConditionsYield
at 80℃; for 3h;A n/a
B n/a
C 97.9%
Dimethylphenylsilane
766-77-8

Dimethylphenylsilane

paracetaldehyde
123-63-7

paracetaldehyde

A

diethyl ether
60-29-7

diethyl ether

B

1,1,3,3-tetramethyl-1,3-diphenyldisiloxane
56-33-7

1,1,3,3-tetramethyl-1,3-diphenyldisiloxane

Conditions
ConditionsYield
With (pentamethylcyclopentadienyl)Ge(II)+B(ArF)4- In dichloromethane-d2 at 50℃; Catalytic behavior; Reagent/catalyst;A n/a
B 97%
ethyl acetate
141-78-6

ethyl acetate

A

diethyl ether
60-29-7

diethyl ether

B

ethoxytriethylsilane
597-67-1

ethoxytriethylsilane

Conditions
ConditionsYield
With triethylsilane; [CpW(CO)2(1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene)]B(C6F5)4 at 23℃; for 26h; Conversion of starting material;A 5.9%
B 96.3%
bis(pentamethylcyclopentadienyl)ytterbium(diethyl ether)

bis(pentamethylcyclopentadienyl)ytterbium(diethyl ether)

tetraethyldiphosphine disulfide
3790-23-6

tetraethyldiphosphine disulfide

A

((CH3)5C5)2Yb(S2P(C2H5)2)
115018-02-5

((CH3)5C5)2Yb(S2P(C2H5)2)

B

diethyl ether
60-29-7

diethyl ether

C

1,1,2,2-tetraethyldiphosphane
3040-63-9

1,1,2,2-tetraethyldiphosphane

D

tetraethyldiphosphane monosulfide

tetraethyldiphosphane monosulfide

Conditions
ConditionsYield
In toluene stirring, 2 h, under N2; concn., cooling to -10°C; elem. anal.;A 96%
B n/a
C n/a
D n/a
triethyloxonium tris(pentafluoroethyl)trifluorophosphate
945614-32-4

triethyloxonium tris(pentafluoroethyl)trifluorophosphate

1-decyl-3-methylimidazol-3-ium chloride

1-decyl-3-methylimidazol-3-ium chloride

A

diethyl ether
60-29-7

diethyl ether

B

chloroethane
75-00-3

chloroethane

C

1-decyl-3-methylimidazolium tris(pentafluoroethyl)trifluorophosphate
916807-26-6

1-decyl-3-methylimidazolium tris(pentafluoroethyl)trifluorophosphate

Conditions
ConditionsYield
at 80℃; for 3h;A n/a
B n/a
C 96%
methyldiphenylsilane
776-76-1

methyldiphenylsilane

paracetaldehyde
123-63-7

paracetaldehyde

A

diethyl ether
60-29-7

diethyl ether

B

1,3-Dimethyl-1,1,3,3-tetraphenyldisiloxan
807-28-3

1,3-Dimethyl-1,1,3,3-tetraphenyldisiloxan

Conditions
ConditionsYield
With (pentamethylcyclopentadienyl)Ge(II)+B(ArF)4- In dichloromethane-d2 at 50℃; Catalytic behavior;A n/a
B 96%
triethyloxonium tris(pentafluoroethyl)trifluorophosphate
945614-32-4

triethyloxonium tris(pentafluoroethyl)trifluorophosphate

trityl chloride
76-83-5

trityl chloride

A

diethyl ether
60-29-7

diethyl ether

B

chloroethane
75-00-3

chloroethane

C

tritylium tris(pentafluoroethyl)trifluorophosphate

tritylium tris(pentafluoroethyl)trifluorophosphate

Conditions
ConditionsYield
at 80℃; for 10h;A n/a
B n/a
C 93.6%
triethyloxonium tris(pentafluoroethyl)trifluorophosphate
945614-32-4

triethyloxonium tris(pentafluoroethyl)trifluorophosphate

1-cyano-4-N,N-dimethylaminopyridinium bromide
59016-54-5

1-cyano-4-N,N-dimethylaminopyridinium bromide

A

ethyl bromide
74-96-4

ethyl bromide

B

diethyl ether
60-29-7

diethyl ether

C

1-cyano-4-dimethylaminopyridinium tris(pentafluoroethyl)trifluorophosphate
945614-37-9

1-cyano-4-dimethylaminopyridinium tris(pentafluoroethyl)trifluorophosphate

Conditions
ConditionsYield
at 60℃; for 5h;A n/a
B n/a
C 93.2%
N-(n-hexyl)-N-methylpyrrolidinium chloride

N-(n-hexyl)-N-methylpyrrolidinium chloride

triethyloxonium tris(pentafluoroethyl)trifluorophosphate
945614-32-4

triethyloxonium tris(pentafluoroethyl)trifluorophosphate

A

diethyl ether
60-29-7

diethyl ether

B

chloroethane
75-00-3

chloroethane

C

1-hexyl-1-methylpyrrolidinium tris(pentafluoroethyl)trifluorophosphate
945614-40-4

1-hexyl-1-methylpyrrolidinium tris(pentafluoroethyl)trifluorophosphate

Conditions
ConditionsYield
at 80℃; for 3h;A n/a
B n/a
C 93%
Diethyl carbonate
105-58-8

Diethyl carbonate

A

diethyl ether
60-29-7

diethyl ether

B

ethanol
64-17-5

ethanol

Conditions
ConditionsYield
With NaX faujasite at 180 - 240℃; for 6h;A 93%
B 5%
ethene
74-85-1

ethene

acetic acid
64-19-7

acetic acid

A

diethyl ether
60-29-7

diethyl ether

B

ethanol
64-17-5

ethanol

C

ethyl acetate
141-78-6

ethyl acetate

Conditions
ConditionsYield
Stage #1: acetic acid With water at 92.4℃;
Stage #2: ethene; cesium nitrate; tungstophosphoric acid; water; mixture of, dried, tabletted at 92.4 - 194.4℃; under 6750.68 Torr; Product distribution / selectivity; Gas phase;
A 3.2%
B 3.6%
C 92.7%
With water; cesium nitrate; tungstophosphoric acid; water; mixture of, dried, tabletted at 92.4 - 165℃; under 6750.68 Torr; Product distribution / selectivity; Gas phase;A 3%
B 3.4%
C 91.5%
With water; lithium nitrate; silica; tungstophosphoric acid; water; mixture of, heated at 150 C at 102.2 - 165℃; under 6750.68 Torr; Product distribution / selectivity; Gas phase;A 2.2%
B 5%
C 90.1%
With water; lithium nitrate; silica; tungstosilicic acid; water; mixture of, heated at 150 C at 102.2 - 165℃; under 6750.68 Torr; Conversion of starting material; Gas phase;A 4.7%
B 7.6%
C 87.7%
ethene
74-85-1

ethene

acrylic acid
79-10-7

acrylic acid

A

diethyl ether
60-29-7

diethyl ether

B

ethanol
64-17-5

ethanol

C

ethyl acrylate
140-88-5

ethyl acrylate

Conditions
ConditionsYield
With water; cesium nitrate; tungstophosphoric acid; water; mixture of, dried, tabletted at 85.6 - 165℃; under 2250.23 Torr; Product distribution / selectivity; Gas phase;A 3.5%
B 4.3%
C 91.8%
ethanol
64-17-5

ethanol

1,3-bis(p-nitrophenyl)-2-thia-1,3-diazaallene
15148-19-3

1,3-bis(p-nitrophenyl)-2-thia-1,3-diazaallene

A

diethyl ether
60-29-7

diethyl ether

B

diethyl sulphite
623-81-4

diethyl sulphite

C

4-nitro-aniline
100-01-6

4-nitro-aniline

Conditions
ConditionsYield
With copper dichloride for 24h; Product distribution; Ambient temperature; other reagent;A 93.6 % Chromat.
B 70%
C 91%
triethyloxonium tris(pentafluoroethyl)trifluorophosphate
945614-32-4

triethyloxonium tris(pentafluoroethyl)trifluorophosphate

1-ethyl-3-methylimidazolium tetrafluoroborate
143314-16-3

1-ethyl-3-methylimidazolium tetrafluoroborate

A

1-ethyl-3-methyl-imidazolium tris(pentafluoroethyl)trifluorophosphate
377739-43-0

1-ethyl-3-methyl-imidazolium tris(pentafluoroethyl)trifluorophosphate

B

diethyl ether
60-29-7

diethyl ether

C

1-fluoroethane
353-36-6

1-fluoroethane

D

boron trifluoride
7637-07-2

boron trifluoride

Conditions
ConditionsYield
at 100℃; for 10h; Product distribution / selectivity;A 90.3%
B n/a
C n/a
D n/a
diethyl ether
60-29-7

diethyl ether

hexafluoro-3-oxatricyclo<3.2.0.02,4>hept-6-ene
74415-68-2

hexafluoro-3-oxatricyclo<3.2.0.02,4>hept-6-ene

A

1-fluoroethane
353-36-6

1-fluoroethane

B

pentafluoro-2-ethoxycyclohexa-2,5-dienone

pentafluoro-2-ethoxycyclohexa-2,5-dienone

Conditions
ConditionsYield
for 2160h; Ambient temperature;A 100%
B 75%
for 2160h; Yields of byproduct given;A n/a
B 21%
diethyl ether
60-29-7

diethyl ether

A

1-fluoroethane
353-36-6

1-fluoroethane

B

pentafluoro-2-ethoxycyclohexa-2,5-dienone

pentafluoro-2-ethoxycyclohexa-2,5-dienone

Conditions
ConditionsYield
With hexafluoro-3-oxatricyclo<3.2.0.02,4>hept-6-ene for 2160h; Ambient temperature;A 100%
B 75%
diethyl ether
60-29-7

diethyl ether

trifluoroacetyl triflate
68602-57-3

trifluoroacetyl triflate

A

ethyl trifluoroacetate,
383-63-1

ethyl trifluoroacetate,

B

trifluoromethanesulfonic acid ethyl ester
425-75-2

trifluoromethanesulfonic acid ethyl ester

Conditions
ConditionsYield
at 0℃;A 100%
B 100%
diethyl ether
60-29-7

diethyl ether

2,3-bis(dimethylsilyl)-1,1,4,4-tetramethyl-1,4-disila-1,4-dihydronaphthalene

2,3-bis(dimethylsilyl)-1,1,4,4-tetramethyl-1,4-disila-1,4-dihydronaphthalene

[2,3-bis(dimethylsilyl)-1,1,4,4-tetramethyl-1,4-disila-1,4-dihydronaphthalenato]bis[(diethyl ether)lithium(I)]

[2,3-bis(dimethylsilyl)-1,1,4,4-tetramethyl-1,4-disila-1,4-dihydronaphthalenato]bis[(diethyl ether)lithium(I)]

Conditions
ConditionsYield
With lithium at 20℃; for 20h; Reduction;100%
diethyl ether
60-29-7

diethyl ether

2,3,6,7-tetrakis(dimethylsilyl)-1,1,4,4,5,5,8,8-octamethyl-1,4,5,8-tetrasila-1,4,5,8-tetrahydroanthracene

2,3,6,7-tetrakis(dimethylsilyl)-1,1,4,4,5,5,8,8-octamethyl-1,4,5,8-tetrasila-1,4,5,8-tetrahydroanthracene

[2,3,6,7-tetrakis(dimethylsilyl)-1,1,4,4,5,5,8,8-octamethyl-1,4,5,8-tetrasila-1,4,5,8-tetrahydroanthracenato]tetrakis[(diethyl ether)lithium(I)]

[2,3,6,7-tetrakis(dimethylsilyl)-1,1,4,4,5,5,8,8-octamethyl-1,4,5,8-tetrasila-1,4,5,8-tetrahydroanthracenato]tetrakis[(diethyl ether)lithium(I)]

Conditions
ConditionsYield
With lithium at 20℃; for 20h; Reduction;100%
diethyl ether
60-29-7

diethyl ether

2-(trifluoromethyl)phenol
444-30-4

2-(trifluoromethyl)phenol

1,4-bis(bromomethyl)-2,5-dibromobenzene
35335-16-1

1,4-bis(bromomethyl)-2,5-dibromobenzene

1,4-dibromo-2,5-bis(2-trifluoromethylphenoxymethyl)benzene
474330-25-1

1,4-dibromo-2,5-bis(2-trifluoromethylphenoxymethyl)benzene

Conditions
ConditionsYield
With sodium hydroxide; potassium carbonate In dichloromethane; acetone100%
4-[[[4-[4-(ethyloxycarbonyl)-1-piperazinyl]phenyl]amino]carbonyl]-1-t-butyloxycarbonyl-piperidine
193902-67-9

4-[[[4-[4-(ethyloxycarbonyl)-1-piperazinyl]phenyl]amino]carbonyl]-1-t-butyloxycarbonyl-piperidine

diethyl ether
60-29-7

diethyl ether

4-[[[4-[4-(ethyloxycarbonyl)-1-piperazinyl]phenyl]amino]carbonyl]piperidine
193902-68-0

4-[[[4-[4-(ethyloxycarbonyl)-1-piperazinyl]phenyl]amino]carbonyl]piperidine

Conditions
ConditionsYield
In 1,4-dioxane; hydrogenchloride100%
diethyl ether
60-29-7

diethyl ether

phenol
108-95-2

phenol

2-phenoxytetrahydropyran
4203-50-3

2-phenoxytetrahydropyran

Conditions
ConditionsYield
With hydrogenchloride In 3,4-dihydro-2H-pyran100%
oxalyl dichloride
79-37-8

oxalyl dichloride

diethyl ether
60-29-7

diethyl ether

3,3-diphenylpropan-1-ol
20017-67-8

3,3-diphenylpropan-1-ol

3,3-diphenylpropanal
4279-81-6

3,3-diphenylpropanal

Conditions
ConditionsYield
With dimethyl sulfoxide; triethylamine In dichloromethane100%
2-(2-ethyl-benzofuran-3-yl)-propionic acid
63606-55-3

2-(2-ethyl-benzofuran-3-yl)-propionic acid

diethyl ether
60-29-7

diethyl ether

2-(2-ethyl-benzofuran-3-yl)-propionamide
63606-56-4

2-(2-ethyl-benzofuran-3-yl)-propionamide

Conditions
ConditionsYield
In thionyl chloride100%
diethyl ether
60-29-7

diethyl ether

N,N-dimethyl-o-toluidine
609-72-3

N,N-dimethyl-o-toluidine

2-(dimethylamino)benzyllithium
64308-58-3

2-(dimethylamino)benzyllithium

Conditions
ConditionsYield
With n-butyllithium In hexane100%
With n-butyllithium In hexane
diethyl ether
60-29-7

diethyl ether

trans-dichloro(ethylene)(2,4,6-trimethylpyridine)platinum
52341-13-6, 12264-20-9

trans-dichloro(ethylene)(2,4,6-trimethylpyridine)platinum

trans-dichloro(diethyl ether)(2,4,6-trimethylpyridine)platinum(II)
91068-18-7

trans-dichloro(diethyl ether)(2,4,6-trimethylpyridine)platinum(II)

Conditions
ConditionsYield
In diethyl ether byproducts: ethylene; Irradiation (UV/VIS);100%
In diethyl ether Irradiation (UV/VIS); the Pt-complex dissolved in Et2O was introduced into a muffshaped Schlenk tube surrounding a 125-W medium-pressure mercury lamp, Philips HPK 125, irradn. for 15 min at room temp., λ<310 nm was eliminated by Pyrex filter; the solvent was removed under reduced pressure at -30°C, the solid was recrystd. at -30°C in pentane-CH2Cl2;95%
diethyl ether
60-29-7

diethyl ether

dimethylgallium tetrahydroborate

dimethylgallium tetrahydroborate

(CH3)2GaBH4(CH3CH2)2O
326903-59-7

(CH3)2GaBH4(CH3CH2)2O

Conditions
ConditionsYield
In diethyl ether (high vac. line); condensing gallium complex in an ampoule with Et2O, warming to room temp. over a period of 30 min; fractionation, collection in a trap at -30°C;100%
diethyl ether
60-29-7

diethyl ether

[(C5H4N)C(CH3)(CH2N(C6H2(CH3)3))2]Zr(CH3)2
293764-40-6

[(C5H4N)C(CH3)(CH2N(C6H2(CH3)3))2]Zr(CH3)2

methyllithium
917-54-4

methyllithium

[C5H4NC(CH3)(CH2NC6H2(CH3)3)2]Zr(methyl)3[Li*diethyl ether]
486413-21-2

[C5H4NC(CH3)(CH2NC6H2(CH3)3)2]Zr(methyl)3[Li*diethyl ether]

Conditions
ConditionsYield
In diethyl ether N2; addn. of methyllithium as 4.4 M ether soln. to ether suspn. of Zr complex at -30° C, stirring at room temp. for 10 min; filtration through Celite, drying the filtrate in vac.; elem. anal.;100%
diethyl ether
60-29-7

diethyl ether

bis[bis(pentamethylcyclopentadienyl)(μ-hydride)yttrium]

bis[bis(pentamethylcyclopentadienyl)(μ-hydride)yttrium]

benzene-d6
1076-43-3

benzene-d6

A

((CH3)5C5)2Y(OC2H5)
165269-59-0

((CH3)5C5)2Y(OC2H5)

B

((CH3)5C5)2Y(D)((C2H5)2O)

((CH3)5C5)2Y(D)((C2H5)2O)

Conditions
ConditionsYield
In diethyl ether; benzene-d6 byproducts: ethane; N2-atmosphere; room temp. (20 min);A 100%
B n/a
diethyl ether
60-29-7

diethyl ether

[La(η5-C5(CH3)5)H]2
98720-39-9

[La(η5-C5(CH3)5)H]2

((CH3)5C5)2La(OC2H5)(O(C2H5)2)
165269-60-3

((CH3)5C5)2La(OC2H5)(O(C2H5)2)

Conditions
ConditionsYield
In benzene-d6 byproducts: ethane; N2-atmosphere; room temp. (10 min); evapn. (vac.);100%
diethyl ether
60-29-7

diethyl ether

supersilylgallium dichloride, dimer

supersilylgallium dichloride, dimer

supersilylgallium dichloride-diethyl ether (1/1)

supersilylgallium dichloride-diethyl ether (1/1)

Conditions
ConditionsYield
In dichloromethane (inert conditions); removal of volatiles (vac.);100%
lithium aluminium tetrahydride
16853-85-3

lithium aluminium tetrahydride

diethyl ether
60-29-7

diethyl ether

Gallium trichloride
13450-90-3

Gallium trichloride

gallane etherate

gallane etherate

Conditions
ConditionsYield
In diethyl ether (N2), GaCl3 in Et2O added dropwise to soln. of LiAlH4 in Et2O at 0°C, stirred at 0°C for 2 h; stored overnight at -20°C, filtered cold, evapd. at -78°C;100%
diethyl ether
60-29-7

diethyl ether

C20H30O6

C20H30O6

A

(1S,3aR,5S,5'S,6R,6a'R)-2,2'-dimethyl-5'-(2-methyl-1,3-dioxolan-4-yl)dihydro-3a'H-3-oxaspiro[bicyclo[3.2.0.]heptane-6,6'-furo[2,3-d][1,3]dioxole]
1244773-04-3

(1S,3aR,5S,5'S,6R,6a'R)-2,2'-dimethyl-5'-(2-methyl-1,3-dioxolan-4-yl)dihydro-3a'H-3-oxaspiro[bicyclo[3.2.0.]heptane-6,6'-furo[2,3-d][1,3]dioxole]

B

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With copper(II) bis(trifluoromethanesulfonate); benzene Inert atmosphere; Irradiation;A 65%
B 100%
diethyl ether
60-29-7

diethyl ether

bis(trimethylsilyl)-trifluoromethylsulfonium tetrakis(pentafluorophenyl)borate
1235436-62-0

bis(trimethylsilyl)-trifluoromethylsulfonium tetrakis(pentafluorophenyl)borate

diethyl(trimethylsilyl)oxonium tetrakis(pentafluorophenyl)borate

diethyl(trimethylsilyl)oxonium tetrakis(pentafluorophenyl)borate

Conditions
ConditionsYield
react. bis(trimethylsilyl)-trifluoromethylsulfonium tetrakis(pentafluorophenyl)borate with Et2O;100%
methyl magnesium iodide
917-64-6

methyl magnesium iodide

benzophenone
119-61-9

benzophenone

diethyl ether
60-29-7

diethyl ether

C18H23IMgO2

C18H23IMgO2

Conditions
ConditionsYield
at 20℃; for 12h;100%
methyl magnesium iodide
917-64-6

methyl magnesium iodide

diethyl ether
60-29-7

diethyl ether

acetophenone
98-86-2

acetophenone

C13H21IMgO2

C13H21IMgO2

Conditions
ConditionsYield
at 20℃; for 12h;100%
diethyl ether
60-29-7

diethyl ether

Cp*Ru(μ-SnC4Et4)2RuCp*

Cp*Ru(μ-SnC4Et4)2RuCp*

lithium
7439-93-2

lithium

[Li(Et2O)]2[Cp*Ru(μ-SnC4Et4)2RuCp*]

[Li(Et2O)]2[Cp*Ru(μ-SnC4Et4)2RuCp*]

Conditions
ConditionsYield
at 20℃; for 1h; Inert atmosphere;100%
diethyl ether
60-29-7

diethyl ether

Ce(decafluorodiphenylamide)3

Ce(decafluorodiphenylamide)3

Ce(decafluorodiphenylamide)3(diethyl ether)2
1445605-48-0

Ce(decafluorodiphenylamide)3(diethyl ether)2

Conditions
ConditionsYield
for 0.5h; Inert atmosphere;100%
chloro(1,5-cyclooctadiene)rhodium(I) dimer

chloro(1,5-cyclooctadiene)rhodium(I) dimer

diethyl ether
60-29-7

diethyl ether

(R,Rb)-[1,1'-binaphthalene]-2,2'-diyl(2'-methoxy-[1,1'-binaphthalen]-2-yl)phosphonite
1365891-80-0, 1365891-81-1

(R,Rb)-[1,1'-binaphthalene]-2,2'-diyl(2'-methoxy-[1,1'-binaphthalen]-2-yl)phosphonite

[RhCl((R,R)-C41H27O3P)(η4-cod)]*(C2H5)2O
1436385-41-9

[RhCl((R,R)-C41H27O3P)(η4-cod)]*(C2H5)2O

Conditions
ConditionsYield
In dichloromethane for 0.5h; Inert atmosphere; Schlenk technique;100%
diethyl ether
60-29-7

diethyl ether

bis(3,5-di-tert-butyl-2-phenol)amine trilithium salt

bis(3,5-di-tert-butyl-2-phenol)amine trilithium salt

tantalum pentachloride
7721-01-9

tantalum pentachloride

(bis(3,5-di-tert-butyl-2-phenol)amine-3H)TaCl2(Et2O)

(bis(3,5-di-tert-butyl-2-phenol)amine-3H)TaCl2(Et2O)

Conditions
ConditionsYield
In toluene Inert atmosphere; Glovebox;100%
morpholine
110-91-8

morpholine

diethyl ether
60-29-7

diethyl ether

N-ethylmorpholine;
100-74-3

N-ethylmorpholine;

Conditions
ConditionsYield
With alumina at 270℃; under 760.051 Torr; Inert atmosphere; Gas phase; Green chemistry;100%
diethyl ether
60-29-7

diethyl ether

Mo2[μ-κ2-PhB(N-2,6-iPr2C6H3)2]2

Mo2[μ-κ2-PhB(N-2,6-iPr2C6H3)2]2

[(tetrahydrofuran)2K18-C-6]2[Mo2{μ-κ2-PhB(2,6-iPr2C6H3)2}2]

[(tetrahydrofuran)2K18-C-6]2[Mo2{μ-κ2-PhB(2,6-iPr2C6H3)2}2]

[(Et2O)K18-C-6][Mo2{μ-κ2-PhB(N-2,6-iPr2C6H3)2}2]

[(Et2O)K18-C-6][Mo2{μ-κ2-PhB(N-2,6-iPr2C6H3)2}2]

Conditions
ConditionsYield
at -35 - 20℃; Inert atmosphere;100%
diethyl ether
60-29-7

diethyl ether

ethylene dibromide
106-93-4

ethylene dibromide

magnesium bromide diethyl etherate
29858-07-9

magnesium bromide diethyl etherate

Conditions
ConditionsYield
With magnesium Heating;100%

Diethyl ether History

   Alchemist Raymundus Lullus is credited with discovering the compound in 1275 AD, although there is no contemporary evidence of this. 
   Ethyl ether (CAS NO.60-29-7) was first synthesized in 1540 by Valerius Cordus, who called it "oil of sweet vitriol" (oleum dulcis vitrioli)—the name was because it was originally discovered by distilling a mixture of ethanol and sulfuric acid (then known as oil of vitriol)—and noted some of its medicinal properties. At about the same time, Theophrastus Bombastus von Hohenheim, better known as Paracelsus, discovered ether's analgesic properties. In 1730 ,August Siegmund Frobenius gave the name ether  to the substance  .

Diethyl ether Consensus Reports

IARC Cancer Review: Animal No Adequate Data IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 , 1987,p. 93.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Diethyl ether Standards and Recommendations

OSHA PEL: TWA 400 ppm; STEL 500 ppm
ACGIH TLV: TWA 400 ppm; STEL 500 ppm
DFG MAK: 400 ppm (1200 mg/m3)
DOT Classification:  3; Label: Flammable Liquid

Diethyl ether Analytical Methods

For occupational chemical analysis use NIOSH: Ethyl Ether, 1610.

Diethyl ether Specification

The Ethyl ether with CAS registry number of 60-29-7 is also known as Diethyl ether. The IUPAC name is Ethoxyethane. It belongs to product categories of Refrigerants; Anhydrous Solvents; Synthetic Organic Chemistry; Chemistry. Its EINECS registry number is 200-467-2. In addition, the formula is C4H10O and the molecular weight is 74.12. This chemical is a colourless liquid and should be cool and dry place away from oxidizing agents.

Physical properties about Ethyl ether are: (1)ACD/LogP: 1.04; (2)ACD/LogD (pH 5.5): 1.041; (3)ACD/LogD (pH 7.4): 1.041; (4)ACD/BCF (pH 5.5): 3.638; (5)ACD/BCF (pH 7.4): 3.638; (6)ACD/KOC (pH 5.5): 87.722; (7)ACD/KOC (pH 7.4): 87.722; (8)#H bond acceptors: 1; (9)#Freely Rotating Bonds: 2; (10)Polar Surface Area: 9.23Å2; (11)Index of Refraction: 1.361; (12)Molar Refractivity: 22.326 cm3; (13)Molar Volume: 100.925 cm3; (14)Surface Tension: 19.09 dyne/cm; (15)Density: 0.734 g/cm3; (16)Enthalpy of Vaporization: 26.52 kJ/mol; (17)Boiling Point: 33.177 °C at 760 mmHg; (18)Vapour Pressure: 566.752 mmHg at 25 °C.

Preparation of Ethyl ether. Firstly, mix ethanol (95%) and concentrated sulfuric acid (98%) with ratio of 1:1 and heat the reaction mixture to 83 °C. Then pass into ethanol vapor and stir the mixture at 120-125 °C. After the reaction, gaseous product is washed through sodium hydroxide solution, saturated solution of sodium bisulfite and distilled water at atmospheric pressure. At last, product is obtained by collecting fraction of 33.5-34.5 °C.

Ethyl ether is prepared by reaction of ethanol (95%) and concentrated sulfuric acid (98%).

Uses of Ethyl ether: it is important anesthetic in medicine. Besides, it is used as analytical reagent for nickel, potassium, magnesium and other analysis. What's more, it is used as solvent, cleaning agent and also used in medicine, electronic and other industries. For example, it is used to produce benzoic acid ethyl ester by reaction with benzoyl chloride. The reaction needs catalyst anhydrous cobalt(II) chloride and solvent acetonitrile at ambient temperature for 8 hours. The tield is about 49%.

The chemical is used to produce benzoic acid ethyl ester by reaction with benzoyl chloride.

When you are using this chemical, please be cautious about it. As a chemical, it is extremely flammable and may form explosive peroxides. What's more, it has danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed. Besides, its repeated exposure may cause skin dryness or cracking vapours may cause drowsiness and dizziness. During using it, wear suitable protective clothing and gloves and do not empty into drains. Keep container in a well-ventilated place and away from sources of ignition. In case of accident or if you feel unwell seek medical advice immediately. It is necessary to take precautionary measures against static discharges.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: CCOCC
2. InChI: InChI=1S/C4H10O/c1-3-5-4-2/h3-4H2,1-2H3
3. InChIKey: RTZKZFJDLAIYFH-UHFFFAOYSA-N

The toxicity data is as follows: 

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LCLo inhalation 76000ppm (76000ppm)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1294, 1935.
frog LDLo subcutaneous 24gm/kg (24000mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1295, 1935.
guinea pig LDLo intraperitoneal 2gm/kg (2000mg/kg)   American Industrial Hygiene Association Journal. Vol. 35, Pg. 21, 1974.
human TCLo inhalation 200ppm (200ppm) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION Journal of Industrial Hygiene and Toxicology. Vol. 25, Pg. 282, 1943.
man LDLo oral 260mg/kg (260mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
mouse LC50 inhalation 31000ppm/30M (31000ppm) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Experimental Animals. Jikken Dobutso Iho. Vol. 34, Pg. 379, 1985.
mouse LD50 intraperitoneal 2420mg/kg (2420mg/kg)   Proceedings of the Western Pharmacology Society. Vol. 27, Pg. 511, 1984.
mouse LD50 intravenous 996mg/kg (996mg/kg)   Journal of Pharmaceutical Sciences. Vol. 67, Pg. 566, 1978.
mouse LDLo subcutaneous 8mg/kg (8mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1295, 1935.
rabbit LCLo inhalation 106000ppm (106000ppm)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1294, 1935.
rabbit LD50 skin > 20mL/kg (20mL/kg)   American Industrial Hygiene Association Journal. Vol. 23, Pg. 95, 1962.
rat LCLo inhalation 32000ppm/4H (32000ppm)   American Industrial Hygiene Association Journal. Vol. 23, Pg. 95, 1962.
rat LD50 oral 1215mg/kg (1215mg/kg)   Toxicology and Applied Pharmacology. Vol. 19, Pg. 699, 1971.

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