Conditions | Yield |
---|---|
With potassium hydroxide; selenium; hydrazine hydrate In water at 40 - 45℃; | 97% |
With potassium hydroxide; selenium(IV) oxide; hydrazine hydrate In water at 40 - 45℃; | 95% |
With disodium diselenide In N,N-dimethyl-formamide at 50℃; for 0.5h; | 88% |
Conditions | Yield |
---|---|
With disodium diselenide; tetrabutylammomium bromide In water for 0.05h; | 90% |
With potassium hydroxide; selenium; hydrazine hydrate In water at 60 - 70℃; | 89% |
With sodium hydroxide; selenium; hydrazine hydrate 1.) MeOH, 6 h; Multistep reaction; | |
With selenium; copper(II) oxide; potassium hydroxide In dimethyl sulfoxide at 90℃; Inert atmosphere; |
Conditions | Yield |
---|---|
With disodium diselenide; sodium hydrogen selenide; N,N-dimethyl-formamide In ethanol at 60 - 70℃; for 7h; | 90% |
1,2-bis(ethylseleno)-1-phenylethene
A
2,5-bis-phenylselenophene
B
diethyl diselenide
Conditions | Yield |
---|---|
at 180℃; for 25h; | A n/a B n/a C 81% D n/a |
n-butyl magnesium bromide
(Z)-1,2-bis(ethylseleno)ethene
A
diethyl diselenide
B
octane
C
cis-5-decene
Conditions | Yield |
---|---|
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether at 20℃; Further byproducts given; | A 145 mg B 226 mg C 78% D 42 mg |
Conditions | Yield |
---|---|
With bis(trimethylsilyl)selenide; boron trifluoride diethyl etherate In dichloromethane at 0℃; for 6h; | A 54% B n/a |
(chloromethyl)trimethoxysilane
A
diethyl diselenide
B
bis(trimethoxysilylmethyl) selenide
Conditions | Yield |
---|---|
In tetrahydrofuran for 1.5h; Heating; | A n/a B n/a C n/a D 35% |
bis-(1-bromo-vinyl) sulfoxide
divinyl selenide
A
diethyl diselenide
B
di<2-(vinylseleno)vinyl> sulfoxide
Conditions | Yield |
---|---|
With ammonia; sodium for 0.666667h; | A 20% B 12% |
Conditions | Yield |
---|---|
With disodium diselenide | |
With potassium diselenide |
Conditions | Yield |
---|---|
With aluminum selenide at 250 - 300℃; |
Conditions | Yield |
---|---|
With aluminum selenide at 250 - 300℃; |
Conditions | Yield |
---|---|
With air | |
With oxygen for 24h; |
Conditions | Yield |
---|---|
With potassium diselenide |
ethyl iodide
1-(2-Chloro-ethylsulfanyl)-propyne
A
diethyl diselenide
B
1-ethylsulfanyl-propyne
Conditions | Yield |
---|---|
With lithium selenide In ammonia |
Conditions | Yield |
---|---|
at 300 - 350℃; |
ethyl bromide
A
diethyl diselenide
B
diethyl-triselenide
C
diethyltrisulfane
Conditions | Yield |
---|---|
With sodium hydroxide; selenium; sulfur; hydrazine hydrate In water at 52 - 56℃; Further byproducts given; |
ethyl bromide
A
Diethyl disulfide
B
diethyl diselenide
C
diethyl sulphide
D
diethylselenium
Conditions | Yield |
---|---|
With sodium hydroxide; selenium; sulfur; hydrazine hydrate In water at 35℃; Product distribution; Further Variations:; Reagents; | A 29.7 % Chromat. B 36.2 % Chromat. C 2.2 % Chromat. D 5.5 % Chromat. |
ethyl bromide
A
Diethyl disulfide
B
diethyl diselenide
C
diethylselenium
D
ethyl ethylselenosulfenate
Conditions | Yield |
---|---|
With sodium hydroxide; selenium; sulfur; hydrazine hydrate In water at 35℃; Further byproducts given; | A 29.7 % Chromat. B 36.2 % Chromat. C 5.5 % Chromat. D 25.9 % Chromat. |
ethyl bromide
A
diethyl diselenide
B
diethyl telluride
C
diethyl ditelluride
Conditions | Yield |
---|---|
With sodium hydroxide; tellurium; sulfur; hydrazine hydrate In water at 35℃; Further byproducts given; | A 43.7 % Chromat. B 3.5 % Chromat. C 30.3 % Chromat. D 1.03 % Chromat. |
diethyl diselenide
Conditions | Yield |
---|---|
With potassium fluoride; copper(l) chloride In 1,4-dioxane at 110℃; for 24h; Inert atmosphere; stereospecific reaction; | 96% |
Conditions | Yield |
---|---|
In hexane at 20℃; for 1h; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
In hexane at 20℃; for 1h; Inert atmosphere; | 93% |
diethyl diselenide
1,3-di-tert-butyl-2,2-dimethyl-1,3,2,4-diazasilagermaetidine
Conditions | Yield |
---|---|
In hexane at 70℃; for 1h; | 92% |
diethyl diselenide
methyl 2-(phenylethynyl)benzoate
4-(ethylselanyl)-3-phenyl-1H-isochromen-1-one
Conditions | Yield |
---|---|
With Oxone In ethanol for 0.666667h; Sonication; regioselective reaction; | 90% |
With tetrabutylammonium tetrafluoroborate In acetonitrile at 20℃; for 0.0833333h; Electrochemical reaction; Green chemistry; | 89% |
Stage #1: diethyl diselenide With iron(III) chloride In dichloromethane at 20℃; for 0.333333h; Stage #2: methyl 2-(phenylethynyl)benzoate In dichloromethane at 20℃; for 18h; regioselective reaction; | 85% |
Conditions | Yield |
---|---|
With potassium hydroxide; selenium; hydrazine hydrate In water at 40 - 45℃; | 97% |
With potassium hydroxide; selenium(IV) oxide; hydrazine hydrate In water at 40 - 45℃; | 95% |
With disodium diselenide In N,N-dimethyl-formamide at 50℃; for 0.5h; | 88% |
Conditions | Yield |
---|---|
With disodium diselenide; tetrabutylammomium bromide In water for 0.05h; | 90% |
With potassium hydroxide; selenium; hydrazine hydrate In water at 60 - 70℃; | 89% |
With sodium hydroxide; selenium; hydrazine hydrate 1.) MeOH, 6 h; Multistep reaction; | |
With selenium; copper(II) oxide; potassium hydroxide In dimethyl sulfoxide at 90℃; Inert atmosphere; |
Conditions | Yield |
---|---|
With disodium diselenide; sodium hydrogen selenide; N,N-dimethyl-formamide In ethanol at 60 - 70℃; for 7h; | 90% |
1,2-bis(ethylseleno)-1-phenylethene
A
2,5-bis-phenylselenophene
B
diethyl diselenide
Conditions | Yield |
---|---|
at 180℃; for 25h; | A n/a B n/a C 81% D n/a |
n-butyl magnesium bromide
(Z)-1,2-bis(ethylseleno)ethene
A
diethyl diselenide
B
octane
C
cis-5-decene
Conditions | Yield |
---|---|
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether at 20℃; Further byproducts given; | A 145 mg B 226 mg C 78% D 42 mg |
Conditions | Yield |
---|---|
With bis(trimethylsilyl)selenide; boron trifluoride diethyl etherate In dichloromethane at 0℃; for 6h; | A 54% B n/a |
(chloromethyl)trimethoxysilane
A
diethyl diselenide
B
bis(trimethoxysilylmethyl) selenide
Conditions | Yield |
---|---|
In tetrahydrofuran for 1.5h; Heating; | A n/a B n/a C n/a D 35% |
bis-(1-bromo-vinyl) sulfoxide
divinyl selenide
A
diethyl diselenide
B
di<2-(vinylseleno)vinyl> sulfoxide
Conditions | Yield |
---|---|
With ammonia; sodium for 0.666667h; | A 20% B 12% |
Conditions | Yield |
---|---|
With disodium diselenide | |
With potassium diselenide |
Conditions | Yield |
---|---|
With aluminum selenide at 250 - 300℃; |
Conditions | Yield |
---|---|
With aluminum selenide at 250 - 300℃; |
Conditions | Yield |
---|---|
With air | |
With oxygen for 24h; |
Conditions | Yield |
---|---|
With potassium diselenide |
ethyl iodide
1-(2-Chloro-ethylsulfanyl)-propyne
A
diethyl diselenide
B
1-ethylsulfanyl-propyne
Conditions | Yield |
---|---|
With lithium selenide In ammonia |
Conditions | Yield |
---|---|
at 300 - 350℃; |
ethyl bromide
A
diethyl diselenide
B
diethyl-triselenide
C
diethyltrisulfane
Conditions | Yield |
---|---|
With sodium hydroxide; selenium; sulfur; hydrazine hydrate In water at 52 - 56℃; Further byproducts given; |
ethyl bromide
A
Diethyl disulfide
B
diethyl diselenide
C
diethyl sulphide
D
diethylselenium
Conditions | Yield |
---|---|
With sodium hydroxide; selenium; sulfur; hydrazine hydrate In water at 35℃; Product distribution; Further Variations:; Reagents; | A 29.7 % Chromat. B 36.2 % Chromat. C 2.2 % Chromat. D 5.5 % Chromat. |
ethyl bromide
A
Diethyl disulfide
B
diethyl diselenide
C
diethylselenium
D
ethyl ethylselenosulfenate
Conditions | Yield |
---|---|
With sodium hydroxide; selenium; sulfur; hydrazine hydrate In water at 35℃; Further byproducts given; | A 29.7 % Chromat. B 36.2 % Chromat. C 5.5 % Chromat. D 25.9 % Chromat. |
ethyl bromide
A
diethyl diselenide
B
diethyl telluride
C
diethyl ditelluride
Conditions | Yield |
---|---|
With sodium hydroxide; tellurium; sulfur; hydrazine hydrate In water at 35℃; Further byproducts given; | A 43.7 % Chromat. B 3.5 % Chromat. C 30.3 % Chromat. D 1.03 % Chromat. |
diethyl diselenide
Conditions | Yield |
---|---|
With potassium fluoride; copper(l) chloride In 1,4-dioxane at 110℃; for 24h; Inert atmosphere; stereospecific reaction; | 96% |
Conditions | Yield |
---|---|
In hexane at 20℃; for 1h; Inert atmosphere; | 95% |
Conditions | Yield |
---|---|
In hexane at 20℃; for 1h; Inert atmosphere; | 93% |
diethyl diselenide
1,3-di-tert-butyl-2,2-dimethyl-1,3,2,4-diazasilagermaetidine
Conditions | Yield |
---|---|
In hexane at 70℃; for 1h; | 92% |
diethyl diselenide
methyl 2-(phenylethynyl)benzoate
4-(ethylselanyl)-3-phenyl-1H-isochromen-1-one
Conditions | Yield |
---|---|
With Oxone In ethanol for 0.666667h; Sonication; regioselective reaction; | 90% |
With tetrabutylammonium tetrafluoroborate In acetonitrile at 20℃; for 0.0833333h; Electrochemical reaction; Green chemistry; | 89% |
Stage #1: diethyl diselenide With iron(III) chloride In dichloromethane at 20℃; for 0.333333h; Stage #2: methyl 2-(phenylethynyl)benzoate In dichloromethane at 20℃; for 18h; regioselective reaction; | 85% |
Conditions | Yield |
---|---|
With tri-n-butyl-tin hydride In various solvent(s) under 0.0750075 Torr; Reduction; | 89% |
With ethanol; sodium |
Conditions | Yield |
---|---|
In chloroform-d1 at 20℃; for 9h; Inert atmosphere; Irradiation; | 88% |
diethyl diselenide
25,27-bis(2-chloroethoxy)-26,28-dihydroxy-5,11,17,23-tetra(tert-butyl)calix[4]arene
Conditions | Yield |
---|---|
With sodium hydroxide; potassium borohydride; ethanol In tetrahydrofuran for 8h; Substitution; Heating; | 87% |
Conditions | Yield |
---|---|
Stage #1: diethyl diselenide With sulfuryl dichloride In dichloromethane at -196 - -20℃; for 0.5h; Stage #2: With antimonypentachloride In dichloromethane at -78℃; for 0.166667h; Stage #3: adamantylidene-adamantane In dichloromethane at -40 - 0℃; for 2h; | 87% |
diethyl diselenide
Conditions | Yield |
---|---|
Stage #1: diethyl diselenide With sodium tetrahydroborate In tetrahydrofuran at 0 - 20℃; for 1.25h; Inert atmosphere; Stage #2: 10-chloro-5,5-difluoro-3,7-dimethyl-5H-4λ4,5λ4-dipyrrolo[1,2-c:2',1'-f ][1,3,2]diazaborinine In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; | 87% |
Conditions | Yield |
---|---|
With bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 20℃; for 5h; regioselective reaction; | 83% |
Diethyldiselenide is an organic compound with the formula C4H10Se2, and its systematic name is the same with the product name. With the CAS registry number 628-39-7, it is also named as Diselenide, diethyl. It belongs to the product category of Organoselenides. Its EINECS number is 211-042-6. In addition, the molecular weight is 216.04. Its classification code is Skin / Eye Irritant. This chemical should be sealed and stored below the temperature of 5 °C. Moreover, it should be protected from oxides.
Physical properties of Diethyldiselenide are: (1)ACD/LogP: 3.22; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.22; (4)ACD/LogD (pH 7.4): 3.22; (5)ACD/BCF (pH 5.5): 164.89; (6)ACD/BCF (pH 7.4): 164.89; (7)ACD/KOC (pH 5.5): 1344.87; (8)ACD/KOC (pH 7.4): 1344.87; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Flash Point: 74.252 °C; (13)Enthalpy of Vaporization: 41.757 kJ/mol; (14)Boiling Point: 199.164 °C at 760 mmHg; (15)Vapour Pressure: 0.49 mmHg at 25°C.
Preparation of Diethyldiselenide: this chemical can be prepared by bromoethane at the temperature of 50 °C. This reaction will need reagent Na2Se2 and solvent dimethylformamide with the reaction time of 30 min. The yield is about 88%.
Uses of Diethyldiselenide: it can be used to produce 3-ethylselanyl-propene at the temperature of 50 °C. It will need reagents ytterbium powder, TMSCl and solvent tetrahydrofuran with the reaction time of 2 hours. The yield is about 60%.
When you are using this chemical, please be cautious about it as the following:
This chemical is toxic by inhalation and if swallowed. It is very toxic to aquatic organisms as it may cause long-term adverse effects in the aquatic environment. This substance has a danger of cumulative effects. When using it, you must not eat, drink or smoke. After contact with skin, you need to wash immediately with plenty of ... (to be specified by the manufacturer). In case of accident or if you feel unwell, you should seek medical advice immediately (show the label where possible).
You can still convert the following datas into molecular structure:
(1)SMILES: [Se]([Se]CC)CC
(2)Std. InChI: InChI=1S/C4H10Se2/c1-3-5-6-4-2/h3-4H2,1-2H3
(3)Std. InChIKey: OMAWWKIPXLIPDE-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rabbit | LCLo | skin | 8600ug/kg (8.6mg/kg) | SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" | National Technical Information Service. Vol. OTS0555235, |
rat | LCLo | inhalation | 2200mg/m3/45M (2200mg/m3) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES BEHAVIORAL: EXCITEMENT | National Technical Information Service. Vol. OTS0555235, |
rat | LD50 | oral | 90mg/kg (90mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) SKIN AND APPENDAGES (SKIN): HAIR: OTHER | National Technical Information Service. Vol. OTS0555235, |
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