2,2'-Dichlorodiethyl ether supplier

Name
2,2'-Dichlorodiethyl ether
EINECS 203-870-1
CAS No. 111-44-4
Article Data47
CAS DataBase
Density 1.156 g/cm³
Solubility Slightly soluble. 1.72 g/100 mL
Melting Point -47 °C(lit.)
Formula C₄H₈Cl₂O
Boiling Point 178.7 °C at 760 mmHg
Molecular Weight 143.013
Flash Point 55 °C
Transport Information UN 1916 6.1/PG 2
Appearance colourless liquid
Safety 27-28-36/37-45-7/9-28A
Risk Codes 10-26/27/28-40-39/23/24/25-23/24/25-11
Molecular Structure
Hazard Symbols T,T+,F
Synonyms Ether,bis(2-chloroethyl) (8CI);1,1'-Oxybis[2-chloroethane];1,5-Dichloro-3-oxapentane;1-Chloro-2-(b-chloroethoxy)ethane;2-(2-Chloroethoxy)ethyl chloride;2-Chloroethyl ether;Bis(2-chloroethyl)ether;Bis(b-chloroethyl) ether;Chlorex;Di(b-Chloroethyl) ether;Di-2-chloroethyl ether;Diethylene glycol dichloride;Oxygenmustard;sym-Dichloroethyl ether;b,b'-Dichlorodiethyl ether;
PSA 9.23000
LogP 1.48060

Synthetic route

: 628-89-7
2-(2-Chloroethoxy)ethanol

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

Conditions

Conditions	Yield
With 2-chloro-1,3-dimethylimidazolinium chloride; triethylamine In dichloromethane at 20℃; for 17h; Chlorination;	92%
With hydrogenchloride; sulfuric acid; zinc(II) chloride at 95℃;

: 106-75-2
diethylene glycol bischloroformate

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

Conditions

Conditions	Yield
With hexabutylguanidinium chloride at 120℃; for 4h;	91%

: 111-46-6
diethylene glycol

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

Conditions

Conditions	Yield
With thionyl chloride Reflux;	86%
With thionyl chloride at 110℃;	84%
With pyridine; thionyl chloride In benzene for 20h; Heating;	35%

: 107-61-9
1,4-oxathiane-4,4-dioxide

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

Conditions

Conditions	Yield
With hydrogenchloride In water at 30℃; for 12h; Temperature;	81.3%

: 507-40-4
tert-butylhypochlorite

: 74-85-1
ethene

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

Conditions

Conditions	Yield
With 2-chloro-ethanol

: 10288-17-2
2-chloroethyl nitrite

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

Conditions

Conditions	Yield
With sulfuryl dichloride at 165℃;

: 74-85-1
ethene

A: 107-06-2
1,2-dichloro-ethane

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

Conditions

Conditions	Yield
With chlorine; 2-chloro-ethanol
With oxirane; chlorine
With oxirane; chlorine; 2-chloro-ethanol

: 507-40-4
tert-butylhypochlorite

: 74-85-1
ethene

: 107-07-3
2-chloro-ethanol

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

...Expand

: 107-07-3
2-chloro-ethanol

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

Conditions

Conditions	Yield
With sulfuric acid Entfernen das entstehende Wasser;
With sulfuryl dichloride at 165℃;
With sulfuric acid at 200 - 250℃;

: 123-91-1
1,4-dioxane

A: 638-56-2
1,11-dichloro-3,6,9-trioxaundecane

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

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

Conditions

Conditions	Yield
With titanium tetrachloride 1.) 20 deg C, 2.) 160 deg C, 5 d; Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 67-56-1
methanol

: 74-85-1
ethene

A: 627-42-9
2-chloroethyl methyl ether

B: 107-06-2
1,2-dichloro-ethane

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

D: 110-56-5
1,4-dichlorobutane

Conditions

Conditions	Yield
With hydrogenchloride at 5 - 10℃; under 45003.6 Torr; electrolysis;	A 47 % Chromat. B 31 % Chromat. C 17 % Chromat. D 6 % Chromat.

...Expand

: 74-85-1
ethene

A: 107-06-2
1,2-dichloro-ethane

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

C: 110-56-5
1,4-dichlorobutane

Conditions

Conditions	Yield
With hydrogenchloride In water; acetonitrile at 5 - 10℃; under 45003.6 Torr; electrolysis, further solvent methanol;	A 82 % Chromat. B 17 % Chromat. C 6 % Chromat.

...Expand

: 74-85-1
ethene

A: 627-42-9
2-chloroethyl methyl ether

B: 107-06-2
1,2-dichloro-ethane

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

D: 110-56-5
1,4-dichlorobutane

Conditions

Conditions	Yield
With hydrogenchloride In methanol at 5 - 10℃; under 45003.6 Torr; electrolysis, further solvent aq. acetonitrile;	A 47 % Chromat. B 31 % Chromat. C 17 % Chromat. D 6 % Chromat.

...Expand

: 74-85-1
ethene

A: 107-06-2
1,2-dichloro-ethane

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

C: 107-07-3
2-chloro-ethanol

Conditions

Conditions	Yield
With hypochloric acid; chlorine In various solvent(s) at 25℃; for 0.00883333h; in tributyl phosphate, in a rotor-pulsation apparatus; Title compound not separated from byproducts;	A 11.9 % Spectr. B 14.4 % Spectr. C 42.1 % Spectr.
With hypochloric acid; chlorine In various solvent(s) at 25℃; for 0.00883333h; in tributyl phosphate, in a rotor pulsation apparatus; Title compound not separated from byproducts;	A 11.9 % Spectr. B 14.4 % Spectr. C 42.1 % Spectr.
With hypochloric acid; chlorine In various solvent(s) at 25℃; for 0.00883333h; Product distribution; dependence of yield of products on time of reaction in tributyl phosphate in a rotor-pulsation apparatus;	A 11.9 % Spectr. B 14.4 % Spectr. C 42.1 % Spectr.

...Expand

: 7664-93-9
sulfuric acid

: 107-07-3
2-chloro-ethanol

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

: 7791-25-5
sulfuryl dichloride

: 107-07-3
2-chloro-ethanol

A: 5411-48-3
sulfuric acid bis-(2-chloroethyl) ester

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

Conditions

Conditions	Yield
at 165℃;

...Expand

: 74-85-1
ethene

: 7782-50-5
chlorine

: 107-07-3
2-chloro-ethanol

A: 107-06-2
1,2-dichloro-ethane

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

Conditions

Conditions	Yield
at 15 - 20℃; Kinetics; unter Lichtausschluss;

...Expand

: 74-85-1
ethene

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

B ethylene chloride and ethylene chlorohydrin: ethylene chloride and ethylene chlorohydrin

Conditions

Conditions	Yield
With chlorine; sodium sulfate at 60℃;
With chlorine; sodium sulfate at 60℃;

: 74-85-1
ethene

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

B ethylene chloride and ethylene glycol-bis-<2-chloro-ethyl ether >: ethylene chloride and ethylene glycol-bis-<2-chloro-ethyl ether >

Conditions

Conditions	Yield
With 1,4-dioxane; polyethylene glycol chlorohydrin; chlorine; 2-chloro-ethanol at 25 - 35℃;
With 1,4-dioxane; chlorine at 20 - 25℃;
With polyethylene glycol mixture; chlorine

: 107-07-3
2-chloro-ethanol

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

B: 5197-62-6
2-[2-(chloroethoxy)ethoxy]ethanol

C: 628-89-7
2-(2-Chloroethoxy)ethanol

D: 107-06-2
1,2-dichloro-ethane

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

F HCl, water: HCl, water

Conditions

Conditions	Yield
at 150℃; for 5h; Product distribution; Kinetics; Rate constant; dependence of the products of ECH decomposition on temperature in sealed tube at 115, 130, 140, 150, 160 deg C;

...Expand

: 7791-25-5
sulfuryl dichloride

: 10288-17-2
2-chloroethyl nitrite

A: 13891-58-2
chloroethyl chlorosulfate

B: 5411-48-3
sulfuric acid bis-(2-chloroethyl) ester

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

...Expand

: 74-85-1
ethene

: 7782-50-5
chlorine

2-chloro-ethanone-(1): 2-chloro-ethanone-(1)

A: 107-06-2
1,2-dichloro-ethane

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

Conditions

Conditions	Yield
at 15 - 20℃; unter Lichtausschluss;

...Expand

: 123-91-1
1,4-dioxane

: 74-85-1
ethene

: 7782-50-5
chlorine

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

B: 107-06-2
1,2-dichloro-ethane

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

Conditions

Conditions	Yield
at 20 - 25℃; weniger als 1 Mol Chlor;
at 20 - 25℃; weniger als 1 Mol Chlor;

...Expand

: 74-85-1
ethene

: 7732-18-5
water

: 7782-50-5
chlorine

A: 107-06-2
1,2-dichloro-ethane

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

C: 107-07-3
2-chloro-ethanol

...Expand

: 64-17-5
ethanol

: 74-85-1
ethene

: 7782-50-5
chlorine

A: 628-34-2
2-chloroethyl ethyl ether

B: 107-06-2
1,2-dichloro-ethane

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

D: 107-07-3
2-chloro-ethanol

...Expand

: 62516-55-6
sulfurous acid bis-(2-chloro-ethyl ester)

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

B SO2: SO2

: 646-06-0
1,3-DIOXOLANE

A: 542-88-1
bis(2-chloromethyl)ether

B: 1462-33-5
2-chloroethyl chloromethyl ether

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

Conditions

Conditions	Yield
Stage #1: 1,3-DIOXOLANE With dichloromethane; tungsten(VI) chloride In Chloroform-D at 20℃; for 192h; Stage #2: With water In Chloroform-D at -20℃;

...Expand

: 3970-21-6
2-Methoxyethoxymethyl chloride

A: 542-88-1
bis(2-chloromethyl)ether

B: 74-87-3
methylene chloride

C: 115-10-6
Dimethyl ether

D: 107-30-2
chloromethyl methyl ether

E: 107-06-2
1,2-dichloro-ethane

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

Conditions

Conditions	Yield
Stage #1: 2-Methoxyethoxymethyl chloride With dichloromethane; tungsten(VI) chloride In Chloroform-D at 20℃; for 12h; Stage #2: With water In Chloroform-D at -20℃;

...Expand

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

: 34270-90-1
2,2'-diiodoethyl ether

Conditions

Conditions	Yield
With sodium iodide In acetone for 120h; Heating / reflux;	100%
With sodium iodide In acetone for 72h; Heating;	81%
With sodium iodide In acetone for 72h; Reflux; Darkness;	81%

: 4403-78-5
ditosylethylenediamine

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

: 93274-33-0
N,N',N'',N'''-tetrakis(tolyl-p-sulphonyl)-1,10-dioxa-4,7,13,16-tetra-azacyclo-octadecane

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide 170 deg C, 5 h; cool, 12 h;	100%
With potassium carbonate In N,N-dimethyl-formamide for 5h; Heating;	78%
With potassium carbonate In N,N-dimethyl-formamide at 5 - 170℃; for 30h;	15%
With potassium carbonate In N,N-dimethyl-formamide at 170℃; for 12h;	14.3%
With potassium carbonate In N,N-dimethyl-formamide at 170℃; for 5h; Yield given;

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

: bis-(2-chloro-ethyl)-ether ; compound with boron chloride

Conditions

Conditions	Yield
With boron trichloride at -78 - 0℃;	100%

: 104-47-2
p-methoxybenzylnitrile

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

: 3648-78-0
4-(4-methoxyphenyl)tetrahydro-2H-pyran-4-carbonitrile

Conditions

Conditions	Yield
Stage #1: p-methoxybenzylnitrile With sodium hydride In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 0.5h; Stage #2: 3-oxa-1,5-dichloropentane In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 2.33333h;	100%
Stage #1: p-methoxybenzylnitrile With sodium hydroxide In N,N-dimethyl-formamide for 0.5h; Stage #2: 3-oxa-1,5-dichloropentane In N,N-dimethyl-formamide at 80 - 100℃; for 5h;	69%
With sodium hydride In N,N-dimethyl-formamide; mineral oil Cooling with ice;	64%
With NaH In dimethyl sulfoxide

: 140-29-4
phenylacetonitrile

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

: 1202-81-9
4-phenyltetrahydro-2H-pyran-4-carbonitrile

Conditions

Conditions	Yield
With sodium hydride; sodium iodide In dimethyl sulfoxide; mineral oil at 20℃; for 12h; Inert atmosphere; Sealed tube;	99%
With sodium amide; toluene

: 91925-82-5
3,5-dihydroxy-4-(phenylmethoxy)benzoic acid methyl ester

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

: 1034343-25-3
methyl 4-O-benzyl-3,5-di-O-methoxymethylgallate

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1h; Inert atmosphere;	99%

: 67-51-6
3,5-dimethyl-1H-pyrazole

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

: 85650-02-8
1,1'-(2,2'-oxybis(ethane-2,1-diyl))bis(3,5-dimethyl-1H-pyrazole)

Conditions

Conditions	Yield
Stage #1: 3,5-dimethyl-1H-pyrazole With potassium hydroxide In dimethyl sulfoxide at 80℃; for 1h; Stage #2: 3-oxa-1,5-dichloropentane In dimethyl sulfoxide at 80℃; Further stages.;	98%

: 16466-61-8
1,2-bis(t-butyloxycarbonyl)hydrazine

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

: 243973-69-5
1,4,5-oxadiazepane-4,5-dicarboxylic acid di-tert-butyl ester

Conditions

Conditions	Yield
Stage #1: 1,2-bis(t-butyloxycarbonyl)hydrazine With sodium hydride In N,N-dimethyl-formamide at -3 - 20℃; for 2.13333h; Stage #2: 3-oxa-1,5-dichloropentane In N,N-dimethyl-formamide at -3 - 20℃; Temperature;	97.1%

: 1704-62-7
1-O-Dimethylaminoethyl-ethylenglykol

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

: C16H38N2O5(2+)*2Cl(1-)

Conditions

Conditions	Yield
In acetonitrile at 60℃; for 24h;	97%

: 104-94-9
4-methoxy-aniline

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

: 955095-74-6
4-(4-methoxyhenyl)morpholine nitric acid salt

Conditions

Conditions	Yield
Stage #1: 4-methoxy-aniline; 3-oxa-1,5-dichloropentane With tetrabutylammomium bromide; sodium hydroxide for 8h; Heating; Stage #2: With nitric acid at 0 - 5℃; for 12h;	97%

: 106-41-2
4-bromo-phenol

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

: 72659-52-0
C16H16Br2O3

Conditions

Conditions	Yield
With sodium hydroxide In dimethyl sulfoxide at 90℃; for 24h;	96%

: 135420-00-7
(4-fluoromethyl-phenyl)-acetonitrile

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

: 473706-10-4
4-(4-fluorophenyl)tetrahydro-2H-pyran-4-carbonitrile

Conditions

Conditions	Yield
With sodium hydride In diethyl ether; dimethyl sulfoxide at 5 - 30℃;	96%

: 616-47-7
1-methyl-1H-imidazole

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

: 1-methyl-3-(2-[2-(1-methyl-1H-imidazol-3-ium-3-yl)ethyloxy]ethyl)-1H-imidazol-3-ium dichloride

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 120℃; for 3h;	96%
In acetonitrile at 100℃; for 48h; Inert atmosphere;	90%

: 153843-74-4
1,3-dihydroxy-4-iodo-2-nitrobenzene

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

: 1155368-39-0
1-iodo-2,4-bis(methoxymethoxy)-3-nitrobenzene

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 1.5h;	96%

: 124-38-9
carbon dioxide

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

: 29943-42-8
Tetrahydro-4H-pyran-4-one

Conditions

Conditions	Yield
With cesium iodide In ethanol; water at 90℃; under 8250.83 Torr; Temperature; Pressure;	95.9%

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

: 88-75-5
2-hydroxynitrobenzene

: 54533-65-2
1,5-bis(o-nitrophenoxy)-3-oxapentane

Conditions

Conditions	Yield
With 15-crown-5; sodium carbonate In N,N-dimethyl-formamide at 140℃; for 5h;	95%
With potassium carbonate In dimethyl sulfoxide at 130℃; for 6h;	85%
With potassium carbonate In N,N-dimethyl-formamide

: 107-15-3
ethylenediamine

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

: 2038-03-1
4-(2-AMINOETHYL)MORPHOLINE

Conditions

Conditions	Yield
With sodium carbonate In acetonitrile for 24h; Heating;	95%

: 3179-63-3
3-Dimethylamino-1-propanol

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

: C14H34N2O3(2+)*2Cl(1-)

Conditions

Conditions	Yield
In acetonitrile at 60℃; for 24h;	95%

: 29430-29-3
2-Benzoyl-hydrazin-1-carbonsaeuremethylester

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

: N-methoxycarbonyl-N'-benzoyl[1,4,5]-oxadiazepane

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl acetamide; N,N-dimethyl-formamide at 0 - 20℃;	95%

: 29366-73-2
2,4-diamino-6-(4-nitrophenyl)-1,3,5-triazine

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

: 4,4'-(6-(4-nitrophenyl)-1,3,5-triazine-2,4-diyl)dimorpholine

Conditions

Conditions	Yield
Stage #1: 2,4-diamino-6-(4-nitrophenyl)-1,3,5-triazine With sodium hydride In N,N-dimethyl acetamide at 55 - 60℃; for 0.166667h; Inert atmosphere; Stage #2: 3-oxa-1,5-dichloropentane In N,N-dimethyl acetamide for 4.5h; Reagent/catalyst; Temperature; Inert atmosphere;	94.6%
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 65℃; Thermodynamic data; Solvent; Reagent/catalyst; Concentration; Temperature; Inert atmosphere; Green chemistry;	77%

: 98-54-4
para-tert-butylphenol

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

: 109879-29-0
1,5-Bis(4-t-butylphenoxy)-3-oxapentane

Conditions

Conditions	Yield
With potassium hydroxide In butan-1-ol for 18h; Heating;	94%
With sodium hydroxide at 180 - 190℃;

: 71676-29-4, 101833-22-1
ethyl 4,6-O-benzylidene-α-D-glucopyranoside

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

: ethyl 4,6-O-benzylidene-2,3-bis-O-[(2-chloroethoxy)ethyl]-α-D-glucopyranoside

Conditions

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In water at 20℃; for 9h;	94%

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

: 24345-74-2
1,5-diazido-3-oxapentane

Conditions

Conditions	Yield
With sodium azide; tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide at 90℃; for 48h;	93%
With sodium azide In N,N-dimethyl-formamide for 17h; Heating;	62.8%
With sodium azide; choline chloride In N,N-dimethyl-formamide at 95℃; Rate constant; var. phase transfer catalysts;
With sodium azide; cetyltributylphosphonium bromide; potassium iodide for 17h; Heating; Yield given;
With sodium azide; cetylpyridinium chloride; potassium iodide In water for 20h; Heating / reflux;

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

: 109776-90-1
2,2,2-trichloro-1-fluoroethyl 2-chloroethyl ether

Conditions

Conditions	Yield
With sulfur tetrafluoride; hydrogen fluoride; chlorine at 80℃; for 5h; Product distribution; other temperature, stainless-steel autoclave, other ratio of reagents;	93%
With sulfur tetrafluoride; hydrogen fluoride; chlorine at 80℃; for 5h; stainless-steel autoclave;	93%

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

: C22H18F6N2O5

: C26H24F6N2O6

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃; Cycloaddition;	93%

: 21715-90-2
endo-N-hydroxy-5-norbornene-2,3-dicarboxyimide

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

: 3-oxapentane-1,5-dioxy-endo-2',3'-dicarboxydiimidenorbornene

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 2h;	92%
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 22h; Gabriel Amine Synthesis;	64.5 g

: 21715-90-2
N-hydroxy-5-norbornene-2,3-dicarboximide

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

: C22H24N2O7

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 24h;	92%

: 1120-24-7
N,N-dimethyldecylamine

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

: diethyl ether-α,ω-didecyldimethylammonium chloride

Conditions

Conditions	Yield
In acetonitrile for 24h; Menshutkin Reaction; Heating;	92%
With sodium carbonate In isopropyl alcohol at 55 - 83℃; for 8h;

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

: 41381-89-9
2-(4-phenylthiazol-2-yl)acetonitrile

: 1314886-95-7
4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-carbonitrile

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide; mineral oil Cooling with ice;	92%

2,2'-Dichlorodiethyl ether Consensus Reports

IARC Cancer Review: Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 (1987),p. 56.(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) ; Animal Sufficient Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 9 (1975),p. 117.(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. On Community Right-To-Know List. On EPA Extremely Hazardous Substances List.

2,2'-Dichlorodiethyl ether Standards and Recommendations

OSHA PEL: TWA 5 ppm; STEL 10 ppm (skin)
ACGIH TLV: TWA 5 ppm; STEL 10 ppm (skin); Not Classifiable as a Human Carcinogen
DFG MAK: 10 ppm (59 mg/m³)
DOT Classification: 6.1; Label: Poison, Flammable Liquid

2,2'-Dichlorodiethyl ether Analytical Methods

For occupational chemical analysis use NIOSH: sym-Dichloroethyl Ether, 1004.

2,2'-Dichlorodiethyl ether Specification

The CAS registry number of Dichloroethyl ether is 111-44-4. The IUPAC name is 1-chloro-2-(2-chloroethoxy)ethane. Its EINECS registry number is 203-870-1. In addition, the molecular formula is C₄H₈Cl₂O and the molecular weight is 143.01. It is a kind of colourless liquid and belongs to the classes of Industrial/Fine Chemicals; Halogen compounds; A-BAlphabetic; Alpha Sort; B; BI - BZ; Volatiles/Semivolatiles.

Physical properties about this chemical are: (1)ACD/LogP: 1.19; (2)ACD/LogD (pH 5.5): 1.19; (3)ACD/LogD (pH 7.4): 1.19 ; (4)#H bond acceptors: 1; (5)#Freely Rotating Bonds: 4; (6)Polar Surface Area: Å²; (7)Index of Refraction: 1.431; (8)Molar Refractivity: 32.02 cm³; (9)Molar Volume: 123.6 cm³; (10)Polarizability: 12.69 ×10^-24cm³; (11)Surface Tension: 29.3 dyne/cm; (12)Density: 1.156 g/cm³; (13)Flash Point: 55 °C; (14)Enthalpy of Vaporization: 39.8 kJ/mol; (15)Boiling Point: 178.7 °C at 760 mmHg; (16)Vapour Pressure: 1.32 mmHg at 25°C.

Preparation of Dichloroethyl ether: it can be prepared by 2,2'-oxy-bis-ethanol. This reaction will need reagent SOCl₂ and pyridine and solvent benzene. The reaction time is 20 hours by heating. The yield is about 35%.

Uses of Dichloroethyl ether: it can be used as solvent of fat, oil, wax, rubber, tar, asphalt, resin and ethyl cellulose. And it is used in the preparation of coating, soil pesticides and dry lotion. In addition, it can be used in organic synthesis and gas chromatography fixed liquid. What's more, it can react with 2-amino-ethanol to get 2-morpholin-4-yl-ethanol. This reaction will need reagent Na₂CO₃ and solvent acetonitrile. The reaction time is 48 hours by heating. The yield is about 83%.

Dichloroethyl ether can react with 2-amino-ethanol to get 2-morpholin-4-yl-ethanol.

When you are using this chemical, please be cautious about it as the following:
This chemical is highly flammable and has danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed. There is limited evidence of a carcinogenic effect. During using it, wear suitable protective clothing and gloves. If the clothing all contaminate it, you should take off the clothing immediately. If it contact with skin, you should wash immediately with plenty of soap-suds. In case of accident or if you feel unwell, seek medical advice immediately (show label where possible). After using it, keep container tightly closed and in a well-ventilated place.

You can still convert the following datas into molecular structure:
(1)SMILES: ClCCOCCCl
(2)InChI: InChI=1/C4H8Cl2O/c5-1-3-7-4-2-6/h1-4H2
(3)InChIKey: ZNSMNVMLTJELDZ-UHFFFAOYAN

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
guinea pig	LC50	inhalation	500ppm/1H (500ppm)		"Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 541, 1986.
guinea pig	LD50	skin	300mg/kg (300mg/kg)		Journal of Industrial Hygiene and Toxicology. Vol. 30, Pg. 63, 1948.
mammal (species unspecified)	LD50	oral	112mg/kg (112mg/kg)		Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 39(4), Pg. 86, 1974.
mouse	LC50	inhalation	650mg/m³/2H (650mg/m³)		"Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 45, 1982.
mouse	LD50	oral	209mg/kg (209mg/kg)	SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Acute Toxicity Data. Journal of the American College of Toxicology, Part B. Vol. 1, Pg. 163, 1992.
rabbit	LD50	oral	126mg/kg (126mg/kg)		"Patty's Industrial Hygiene and Toxicology," 3rd rev. ed., Clayton, G.D., and F.E. Clayton, eds., New York, John Wiley & Sons, Inc., 1978-82. Vol. 3 originally pub. in 1979; pub. as 2n rev. ed. in 1985.Vol. 2A, Pg. 2518, 1981.
rabbit	LD50	skin	90mg/kg (90mg/kg)		"Patty's Industrial Hygiene and Toxicology," 3rd rev. ed., Clayton, G.D., and F.E. Clayton, eds., New York, John Wiley & Sons, Inc., 1978-82. Vol. 3 originally pub. in 1979; pub. as 2n rev. ed. in 1985.Vol. 2A, Pg. 2518, 1981.
rat	LC50	inhalation	330mg/m³/4H (330mg/m³)		"Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 45, 1982.
rat	LD50	oral	75mg/kg (75mg/kg)		Journal of Industrial Hygiene and Toxicology. Vol. 30, Pg. 63, 1948.

Product Name

2,2'-Dichlorodiethyl ether

Synthetic route

2,2'-Dichlorodiethyl ether Consensus Reports

2,2'-Dichlorodiethyl ether Standards and Recommendations

2,2'-Dichlorodiethyl ether Analytical Methods

2,2'-Dichlorodiethyl ether Specification

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