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℃; |
Conditions | Yield |
---|---|
With hexabutylguanidinium chloride at 120℃; for 4h; | 91% |
Conditions | Yield |
---|---|
With thionyl chloride Reflux; | 86% |
With thionyl chloride at 110℃; | 84% |
With pyridine; thionyl chloride In benzene for 20h; Heating; | 35% |
Conditions | Yield |
---|---|
With hydrogenchloride In water at 30℃; for 12h; Temperature; | 81.3% |
Conditions | Yield |
---|---|
With 2-chloro-ethanol |
2-chloroethyl nitrite
3-oxa-1,5-dichloropentane
Conditions | Yield |
---|---|
With sulfuryl dichloride at 165℃; |
Conditions | Yield |
---|---|
With chlorine; 2-chloro-ethanol | |
With oxirane; chlorine | |
With oxirane; chlorine; 2-chloro-ethanol |
tert-butylhypochlorite
ethene
2-chloro-ethanol
3-oxa-1,5-dichloropentane
Conditions | Yield |
---|---|
With sulfuric acid Entfernen das entstehende Wasser; | |
With sulfuryl dichloride at 165℃; | |
With sulfuric acid at 200 - 250℃; |
1,4-dioxane
A
1,11-dichloro-3,6,9-trioxaundecane
B
1,2-bis(2-chloroethoxy)ethane
C
3-oxa-1,5-dichloropentane
Conditions | Yield |
---|---|
With titanium tetrachloride 1.) 20 deg C, 2.) 160 deg C, 5 d; Yield given. Multistep reaction. Yields of byproduct given; |
methanol
ethene
A
2-chloroethyl methyl ether
B
1,2-dichloro-ethane
C
3-oxa-1,5-dichloropentane
D
1,4-dichlorobutane
Conditions | Yield |
---|---|
With hydrogenchloride at 5 - 10℃; under 45003.6 Torr; electrolysis; | A 47 % Chromat. B 31 % Chromat. C 17 % Chromat. D 6 % Chromat. |
ethene
A
1,2-dichloro-ethane
B
3-oxa-1,5-dichloropentane
C
1,4-dichlorobutane
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. |
ethene
A
2-chloroethyl methyl ether
B
1,2-dichloro-ethane
C
3-oxa-1,5-dichloropentane
D
1,4-dichlorobutane
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. |
ethene
A
1,2-dichloro-ethane
B
3-oxa-1,5-dichloropentane
C
2-chloro-ethanol
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. |
sulfuryl dichloride
2-chloro-ethanol
A
sulfuric acid bis-(2-chloroethyl) ester
B
3-oxa-1,5-dichloropentane
Conditions | Yield |
---|---|
at 165℃; |
ethene
chlorine
2-chloro-ethanol
A
1,2-dichloro-ethane
B
3-oxa-1,5-dichloropentane
Conditions | Yield |
---|---|
at 15 - 20℃; Kinetics; unter Lichtausschluss; |
Conditions | Yield |
---|---|
With chlorine; sodium sulfate at 60℃; | |
With chlorine; sodium sulfate at 60℃; |
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 |
2-chloro-ethanol
A
1,4-dioxane
B
2-[2-(chloroethoxy)ethoxy]ethanol
C
2-(2-Chloroethoxy)ethanol
D
1,2-dichloro-ethane
E
3-oxa-1,5-dichloropentane
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; |
sulfuryl dichloride
2-chloroethyl nitrite
A
chloroethyl chlorosulfate
B
sulfuric acid bis-(2-chloroethyl) ester
C
3-oxa-1,5-dichloropentane
ethene
chlorine
A
1,2-dichloro-ethane
B
3-oxa-1,5-dichloropentane
Conditions | Yield |
---|---|
at 15 - 20℃; unter Lichtausschluss; |
1,4-dioxane
ethene
chlorine
A
1,2-bis(2-chloroethoxy)ethane
B
1,2-dichloro-ethane
C
3-oxa-1,5-dichloropentane
Conditions | Yield |
---|---|
at 20 - 25℃; weniger als 1 Mol Chlor; | |
at 20 - 25℃; weniger als 1 Mol Chlor; |
ethene
water
chlorine
A
1,2-dichloro-ethane
B
3-oxa-1,5-dichloropentane
C
2-chloro-ethanol
ethanol
ethene
chlorine
A
2-chloroethyl ethyl ether
B
1,2-dichloro-ethane
C
3-oxa-1,5-dichloropentane
D
2-chloro-ethanol
1,3-DIOXOLANE
A
bis(2-chloromethyl)ether
B
2-chloroethyl chloromethyl ether
C
3-oxa-1,5-dichloropentane
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℃; |
2-Methoxyethoxymethyl chloride
A
bis(2-chloromethyl)ether
B
methylene chloride
C
Dimethyl ether
D
chloromethyl methyl ether
E
1,2-dichloro-ethane
F
3-oxa-1,5-dichloropentane
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℃; |
3-oxa-1,5-dichloropentane
2,2'-diiodoethyl ether
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% |
ditosylethylenediamine
3-oxa-1,5-dichloropentane
N,N',N'',N'''-tetrakis(tolyl-p-sulphonyl)-1,10-dioxa-4,7,13,16-tetra-azacyclo-octadecane
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; |
3-oxa-1,5-dichloropentane
Conditions | Yield |
---|---|
With boron trichloride at -78 - 0℃; | 100% |
p-methoxybenzylnitrile
3-oxa-1,5-dichloropentane
4-(4-methoxyphenyl)tetrahydro-2H-pyran-4-carbonitrile
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 |
phenylacetonitrile
3-oxa-1,5-dichloropentane
4-phenyltetrahydro-2H-pyran-4-carbonitrile
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 |
3,5-dihydroxy-4-(phenylmethoxy)benzoic acid methyl ester
3-oxa-1,5-dichloropentane
methyl 4-O-benzyl-3,5-di-O-methoxymethylgallate
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1h; Inert atmosphere; | 99% |
3,5-dimethyl-1H-pyrazole
3-oxa-1,5-dichloropentane
1,1'-(2,2'-oxybis(ethane-2,1-diyl))bis(3,5-dimethyl-1H-pyrazole)
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% |
1,2-bis(t-butyloxycarbonyl)hydrazine
3-oxa-1,5-dichloropentane
1,4,5-oxadiazepane-4,5-dicarboxylic acid di-tert-butyl ester
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% |
Conditions | Yield |
---|---|
In acetonitrile at 60℃; for 24h; | 97% |
4-methoxy-aniline
3-oxa-1,5-dichloropentane
4-(4-methoxyhenyl)morpholine nitric acid salt
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% |
Conditions | Yield |
---|---|
With sodium hydroxide In dimethyl sulfoxide at 90℃; for 24h; | 96% |
(4-fluoromethyl-phenyl)-acetonitrile
3-oxa-1,5-dichloropentane
4-(4-fluorophenyl)tetrahydro-2H-pyran-4-carbonitrile
Conditions | Yield |
---|---|
With sodium hydride In diethyl ether; dimethyl sulfoxide at 5 - 30℃; | 96% |
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 120℃; for 3h; | 96% |
In acetonitrile at 100℃; for 48h; Inert atmosphere; | 90% |
1,3-dihydroxy-4-iodo-2-nitrobenzene
3-oxa-1,5-dichloropentane
1-iodo-2,4-bis(methoxymethoxy)-3-nitrobenzene
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 1.5h; | 96% |
Conditions | Yield |
---|---|
With cesium iodide In ethanol; water at 90℃; under 8250.83 Torr; Temperature; Pressure; | 95.9% |
3-oxa-1,5-dichloropentane
2-hydroxynitrobenzene
1,5-bis(o-nitrophenoxy)-3-oxapentane
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 |
Conditions | Yield |
---|---|
With sodium carbonate In acetonitrile for 24h; Heating; | 95% |
Conditions | Yield |
---|---|
In acetonitrile at 60℃; for 24h; | 95% |
2-Benzoyl-hydrazin-1-carbonsaeuremethylester
3-oxa-1,5-dichloropentane
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl acetamide; N,N-dimethyl-formamide at 0 - 20℃; | 95% |
2,4-diamino-6-(4-nitrophenyl)-1,3,5-triazine
3-oxa-1,5-dichloropentane
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% |
para-tert-butylphenol
3-oxa-1,5-dichloropentane
1,5-Bis(4-t-butylphenoxy)-3-oxapentane
Conditions | Yield |
---|---|
With potassium hydroxide In butan-1-ol for 18h; Heating; | 94% |
With sodium hydroxide at 180 - 190℃; |
ethyl 4,6-O-benzylidene-α-D-glucopyranoside
3-oxa-1,5-dichloropentane
Conditions | Yield |
---|---|
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In water at 20℃; for 9h; | 94% |
3-oxa-1,5-dichloropentane
1,5-diazido-3-oxapentane
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; |
3-oxa-1,5-dichloropentane
2,2,2-trichloro-1-fluoroethyl 2-chloroethyl ether
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% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 60℃; Cycloaddition; | 93% |
endo-N-hydroxy-5-norbornene-2,3-dicarboxyimide
3-oxa-1,5-dichloropentane
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 |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 24h; | 92% |
Conditions | Yield |
---|---|
In acetonitrile for 24h; Menshutkin Reaction; Heating; | 92% |
With sodium carbonate In isopropyl alcohol at 55 - 83℃; for 8h; |
3-oxa-1,5-dichloropentane
2-(4-phenylthiazol-2-yl)acetonitrile
4-(4-phenylthiazol-2-yl)tetrahydro-2H-pyran-4-carbonitrile
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide; mineral oil Cooling with ice; | 92% |
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%.
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. |
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