628-39-7

Basic information

• Product Name: DIETHYLDISELENIDE
• Synonyms: diethyldiselenium;Diethyl perselenide;ethyldiselanylethane;DIETHYLDISELENIDE;diselenide,diethyl;ethyldiselenide;DiethyldiS34-0550;Diethyldiselenidelightyellowliq
• CAS NO: 628-39-7
• Molecular Formula: C₄H₁₀Se₂
• Molecular Weight: 216.04
• EINECS: 211-042-6
• Product Categories: organoselenides
• Mol File: 628-39-7.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 85°C 21mm
• Flash Point: 22°C
• Appearance: red-brown/liquid
• Density: 1,23 g/cm3
• Vapor Pressure: 0.489mmHg at 25°C
• Refractive Index: 1.476825
• Storage Temp.: below 5° C
• Sensitive: air sensitive, store cold
• CAS DataBase Reference: DIETHYLDISELENIDE(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYLDISELENIDE(628-39-7)
• EPA Substance Registry System: DIETHYLDISELENIDE(628-39-7)

Safety Data

• Statements: 23/25-33-50/53
• Safety Statements: 20/21-28-45
• RIDADR: 3283
• RTECS: JM9151750
• TSCA: No
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 628-39-7(Hazardous Substances Data)

Usage

Hazard

A poison by ingestion and skin contact. Low toxicity by inhalation. A moderate eye irritant.

InChI:InChI=1/C4H10Se2/c1-3-5-6-4-2/h3-4H2,1-2H3

Synthetic route

ethyl bromide (74-96-4) → diethyl diselenide (628-39-7)

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%

ethyl iodide (75-03-6) → diethyl diselenide (628-39-7)

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;

acetaldehyde (75-07-0) → diethyl diselenide (628-39-7)

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 (95494-85-2) → 2,5-bis-phenylselenophene (18782-55-3) + diethyl diselenide (628-39-7) + (1-ethylseleno)-1-phenylethene + (tris-ethylselanyl-vinyl)-benzene

Conditions	Yield
at 180℃; for 25h;	A n/a B n/a C 81% D n/a

n-butyl magnesium bromide (693-03-8) + (Z)-1,2-bis(ethylseleno)ethene (175538-67-7) → diethyl diselenide (628-39-7) + octane (111-65-9) + cis-5-decene (7433-78-5) + (Z)-ethyl-1-hexene-1-yl selenide

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

acetaldehyde (75-07-0) → 2,4,6-trimethyl-1,3,5-triselenane (15732-69-1) + diethyl diselenide (628-39-7)

Conditions	Yield
With bis(trimethylsilyl)selenide; boron trifluoride diethyl etherate In dichloromethane at 0℃; for 6h;	A 54% B n/a

(chloromethyl)trimethoxysilane (5926-26-1) + GENERIC INORGANIC CATION; ethaneselenolate → diethyl diselenide (628-39-7) + bis(trimethoxysilylmethyl) selenide (126912-03-6) + ethyl (trimethoxysilyl)methyl selenide + bis(trimethoxysilylmethyl)diselenide

Conditions	Yield
In tetrahydrofuran for 1.5h; Heating;	A n/a B n/a C n/a D 35%

bis-(1-bromo-vinyl) sulfoxide (17912-00-4) + divinyl selenide (57796-75-5) → diethyl diselenide (628-39-7) + di<2-(vinylseleno)vinyl> sulfoxide (136308-15-1)

Conditions	Yield
With ammonia; sodium for 0.666667h;	A 20% B 12%

diethyl sulfate (64-67-5) → diethyl diselenide (628-39-7)

Conditions	Yield
With disodium diselenide
With potassium diselenide

diethyl ether (60-29-7) → diethyl diselenide (628-39-7)

Conditions	Yield
With aluminum selenide at 250 - 300℃;

ethanol (64-17-5) → diethyl diselenide (628-39-7)

Conditions	Yield
With aluminum selenide at 250 - 300℃;

ethaneselenol (593-69-1) → diethyl diselenide (628-39-7)

Conditions	Yield
With air
With oxygen for 24h;

potassium ethyl sulfate (563-17-7) → diethyl diselenide (628-39-7)

Conditions	Yield
With potassium diselenide

ethanol (64-17-5) + ethaneselenol (593-69-1) + ethylene dibromide (106-93-4) → diethyl diselenide (628-39-7)

ethyl iodide (75-03-6) + 1-(2-Chloro-ethylsulfanyl)-propyne (80637-16-7) → diethyl diselenide (628-39-7) + 1-ethylsulfanyl-propyne (13597-15-4)

Conditions	Yield
With lithium selenide In ammonia

ethylene dibromide (106-93-4) + Na salt of ethylseleno mercaptan → diethyl diselenide (628-39-7) + ethene (74-85-1)

ethaneselenol (593-69-1) + air → diethyl diselenide (628-39-7)

diethyl ether (60-29-7) + aluminium selenide → diethyl diselenide (628-39-7) + diethylselenium (627-53-2)

Conditions	Yield
at 300 - 350℃;

ethyl bromide (74-96-4) → diethyl diselenide (628-39-7) + diethyl-triselenide (107976-06-7) + diethyltrisulfane (3600-24-6) + C4H10S2Se

Conditions	Yield
With sodium hydroxide; selenium; sulfur; hydrazine hydrate In water at 52 - 56℃; Further byproducts given;

ethyl bromide (74-96-4) → Diethyl disulfide (110-81-6) + diethyl diselenide (628-39-7) + diethyl sulphide (352-93-2) + diethylselenium (627-53-2)

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 (74-96-4) → Diethyl disulfide (110-81-6) + diethyl diselenide (628-39-7) + diethylselenium (627-53-2) + ethyl ethylselenosulfenate (88890-93-1)

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 (74-96-4) → diethyl diselenide (628-39-7) + diethyl telluride (627-54-3) + diethyl ditelluride (26105-63-5) + C4H10SeTe

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 (628-39-7) + (2,3,4,6-tetra-O-benzyl-2-β-D-glucopyranosyl)tri-n-butylstannane → ethyl-2,3,4,6-tetra-O-benzyl-1-seleno-β-D-glucopyranoside

Conditions	Yield
With potassium fluoride; copper(l) chloride In 1,4-dioxane at 110℃; for 24h; Inert atmosphere; stereospecific reaction;	96%

diethyl diselenide (628-39-7) + bis[bis(trimethylsilyl)amido]stannylene → C16H46N2Se2Si4Sn

Conditions	Yield
In hexane at 20℃; for 1h; Inert atmosphere;	95%

diethyl diselenide (628-39-7) + bis[bis(trimethylsilyl)amino]germanium(II) (59863-12-6) → C16H46GeN2Se2Si4

Conditions	Yield
In hexane at 20℃; for 1h; Inert atmosphere;	93%

diethyl diselenide (628-39-7) + 1,3-di-tert-butyl-2,2-dimethyl-1,3,2,4-diazasilagermaetidine (84806-15-5) → [Me2Si(Nt-Bu2)Ge{SeEt}2]

Conditions	Yield
In hexane at 70℃; for 1h;	92%

diethyl diselenide (628-39-7) + methyl 2-(phenylethynyl)benzoate (33578-05-1) → 4-(ethylselanyl)-3-phenyl-1H-isochromen-1-one (1314961-26-6)

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%

ethyl bromide (74-96-4) → diethyl diselenide (628-39-7)

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%

ethyl iodide (75-03-6) → diethyl diselenide (628-39-7)

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;

acetaldehyde (75-07-0) → diethyl diselenide (628-39-7)

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 (95494-85-2) → 2,5-bis-phenylselenophene (18782-55-3) + diethyl diselenide (628-39-7) + (1-ethylseleno)-1-phenylethene + (tris-ethylselanyl-vinyl)-benzene

Conditions	Yield
at 180℃; for 25h;	A n/a B n/a C 81% D n/a

n-butyl magnesium bromide (693-03-8) + (Z)-1,2-bis(ethylseleno)ethene (175538-67-7) → diethyl diselenide (628-39-7) + octane (111-65-9) + cis-5-decene (7433-78-5) + (Z)-ethyl-1-hexene-1-yl selenide

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

acetaldehyde (75-07-0) → 2,4,6-trimethyl-1,3,5-triselenane (15732-69-1) + diethyl diselenide (628-39-7)

Conditions	Yield
With bis(trimethylsilyl)selenide; boron trifluoride diethyl etherate In dichloromethane at 0℃; for 6h;	A 54% B n/a

(chloromethyl)trimethoxysilane (5926-26-1) + GENERIC INORGANIC CATION; ethaneselenolate → diethyl diselenide (628-39-7) + bis(trimethoxysilylmethyl) selenide (126912-03-6) + ethyl (trimethoxysilyl)methyl selenide + bis(trimethoxysilylmethyl)diselenide

Conditions	Yield
In tetrahydrofuran for 1.5h; Heating;	A n/a B n/a C n/a D 35%

bis-(1-bromo-vinyl) sulfoxide (17912-00-4) + divinyl selenide (57796-75-5) → diethyl diselenide (628-39-7) + di<2-(vinylseleno)vinyl> sulfoxide (136308-15-1)

Conditions	Yield
With ammonia; sodium for 0.666667h;	A 20% B 12%

diethyl sulfate (64-67-5) → diethyl diselenide (628-39-7)

Conditions	Yield
With disodium diselenide
With potassium diselenide

diethyl ether (60-29-7) → diethyl diselenide (628-39-7)

Conditions	Yield
With aluminum selenide at 250 - 300℃;

ethanol (64-17-5) → diethyl diselenide (628-39-7)

Conditions	Yield
With aluminum selenide at 250 - 300℃;

ethaneselenol (593-69-1) → diethyl diselenide (628-39-7)

Conditions	Yield
With air
With oxygen for 24h;

potassium ethyl sulfate (563-17-7) → diethyl diselenide (628-39-7)

Conditions	Yield
With potassium diselenide

ethanol (64-17-5) + ethaneselenol (593-69-1) + ethylene dibromide (106-93-4) → diethyl diselenide (628-39-7)

ethyl iodide (75-03-6) + 1-(2-Chloro-ethylsulfanyl)-propyne (80637-16-7) → diethyl diselenide (628-39-7) + 1-ethylsulfanyl-propyne (13597-15-4)

Conditions	Yield
With lithium selenide In ammonia

ethylene dibromide (106-93-4) + Na salt of ethylseleno mercaptan → diethyl diselenide (628-39-7) + ethene (74-85-1)

ethaneselenol (593-69-1) + air → diethyl diselenide (628-39-7)

diethyl ether (60-29-7) + aluminium selenide → diethyl diselenide (628-39-7) + diethylselenium (627-53-2)

Conditions	Yield
at 300 - 350℃;

ethyl bromide (74-96-4) → diethyl diselenide (628-39-7) + diethyl-triselenide (107976-06-7) + diethyltrisulfane (3600-24-6) + C4H10S2Se

Conditions	Yield
With sodium hydroxide; selenium; sulfur; hydrazine hydrate In water at 52 - 56℃; Further byproducts given;

ethyl bromide (74-96-4) → Diethyl disulfide (110-81-6) + diethyl diselenide (628-39-7) + diethyl sulphide (352-93-2) + diethylselenium (627-53-2)

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 (74-96-4) → Diethyl disulfide (110-81-6) + diethyl diselenide (628-39-7) + diethylselenium (627-53-2) + ethyl ethylselenosulfenate (88890-93-1)

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 (74-96-4) → diethyl diselenide (628-39-7) + diethyl telluride (627-54-3) + diethyl ditelluride (26105-63-5) + C4H10SeTe

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 (628-39-7) + (2,3,4,6-tetra-O-benzyl-2-β-D-glucopyranosyl)tri-n-butylstannane → ethyl-2,3,4,6-tetra-O-benzyl-1-seleno-β-D-glucopyranoside

Conditions	Yield
With potassium fluoride; copper(l) chloride In 1,4-dioxane at 110℃; for 24h; Inert atmosphere; stereospecific reaction;	96%

diethyl diselenide (628-39-7) + bis[bis(trimethylsilyl)amido]stannylene → C16H46N2Se2Si4Sn

Conditions	Yield
In hexane at 20℃; for 1h; Inert atmosphere;	95%

diethyl diselenide (628-39-7) + bis[bis(trimethylsilyl)amino]germanium(II) (59863-12-6) → C16H46GeN2Se2Si4

Conditions	Yield
In hexane at 20℃; for 1h; Inert atmosphere;	93%

diethyl diselenide (628-39-7) + 1,3-di-tert-butyl-2,2-dimethyl-1,3,2,4-diazasilagermaetidine (84806-15-5) → [Me2Si(Nt-Bu2)Ge{SeEt}2]

Conditions	Yield
In hexane at 70℃; for 1h;	92%

diethyl diselenide (628-39-7) + methyl 2-(phenylethynyl)benzoate (33578-05-1) → 4-(ethylselanyl)-3-phenyl-1H-isochromen-1-one (1314961-26-6)

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%

diethyl diselenide (628-39-7) → ethaneselenol (593-69-1)

Conditions	Yield
With tri-n-butyl-tin hydride In various solvent(s) under 0.0750075 Torr; Reduction;	89%
With ethanol; sodium

diethyl diselenide (628-39-7) + 1,2-diisocyanobenzene (94217-36-4) → 2,3-bis(ethylselanyl)quinoxaline

Conditions	Yield
In chloroform-d1 at 20℃; for 9h; Inert atmosphere; Irradiation;	88%

diethyl diselenide (628-39-7) + 25,27-bis(2-chloroethoxy)-26,28-dihydroxy-5,11,17,23-tetra(tert-butyl)calix[4]arene (189296-97-7) → C52H72O4Se2

Conditions	Yield
With sodium hydroxide; potassium borohydride; ethanol In tetrahydrofuran for 8h; Substitution; Heating;	87%

diethyl diselenide (628-39-7) + adamantylidene-adamantane (30541-56-1) → C22H33Se(1+)*Cl6Sb(1-)

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 (628-39-7) + 10-chloro-5,5-difluoro-3,7-dimethyl-5H-4λ4,5λ4-dipyrrolo[1,2-c:2',1'-f ][1,3,2]diazaborinine → 10-(ethylselanyl)-5,5-difluoro-3,7-dimethyl-5H-4λ4,5λ4-dipyrrolo[1,2-c:2',1'-f ][1,3,2]diazaborinine

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%

diethyl diselenide (628-39-7) + coumarin (91-64-5) → 3-(ethylselanyl)-2H-chromen-2-one

Conditions	Yield
With bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 20℃; for 5h; regioselective reaction;	83%

Upstream product

• 593-69-1 ethaneselenol 
• 60-29-7 diethyl ether 
• 5926-26-1 (chloromethyl)trimethoxysilane 
• 74-96-4 ethyl bromide 
• 693-03-8 n-butyl magnesium bromide 
• 175538-67-7 (Z)-1,2-bis(ethylseleno)ethene 
• 106-93-4 ethylene dibromide 
• 75-07-0 acetaldehyde 
• 75-03-6 ethyl iodide 
• 80637-16-7 1-(2-Chloro-ethylsulfanyl)-propyne 
• 17912-00-4 bis-(1-bromo-vinyl) sulfoxide 
• 57796-75-5 divinyl selenide 
• 64-17-5 ethanol 
• 563-17-7 potassium ethyl sulfate 

Downstream Products

• 593-69-1 ethaneselenol 
• 950894-26-5 (Z)-1-(ethylseleno)-1,4-diphenylbut-1-en-3-yne 
• 1159428-91-7 C₁₁H₁₇NSe 
• 135250-00-9 Se-ethyl selenobenzoate 
• 463944-47-0 benzyl ethyl selenide 
• 1314961-26-6 4-(ethylselenyl)-3-phenyl-1H-isochromen-1-one 
• 1332697-99-0 3-(ethylselenyl)-2-phenyl-4H-chromen-4-one 
• 1350262-07-5 C₁₆H₁₄OS 
• 1393806-31-9 (1S,2S)-1-(ethylselanyl)-N,N-dimethyl-1-phenylpropan-2-amine 
• 1422018-00-5 4-(ethylselenyl)-3,5-diphenylisoxazole 
• 80920-14-5 2-(ethylselanyl)-1-phenylethan-1-one 

Relevant articles and documents

Aqueous phase preparation method of dialkyl diselenide ether compound

The method comprises the following steps: taking the compound represented by the formula (II) as a reaction raw material and I as a reaction raw material, and taking water or ethanol as a solvent under Se 40 - 75 °C conditions to obtain the reaction liquid to obtain the dialkyl diselenium ether compound shown in the formula (II KOH). The reaction is short in reaction time, does not need a metal catalyst, uses water as a solvent, and belongs to green and environment-friendly reaction. Economy, high efficiency, green, environmental protection.

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