Product Name

  • Name

    Diphenyl diselenide

  • EINECS 216-780-2
  • CAS No. 1666-13-3
  • Article Data348
  • CAS DataBase
  • Density 1.5570
  • Solubility insoluble in water
  • Melting Point 60 °C
  • Formula C12H10Se2
  • Boiling Point 377.343 °C at 760 mmHg
  • Molecular Weight 312.131
  • Flash Point 182.011 °C
  • Transport Information UN 3283 6.1/PG 2
  • Appearance yellow crystalline powder
  • Safety 20/21-28-45-60-61-28A
  • Risk Codes 23/25-33-50/53
  • Molecular Structure Molecular Structure of 1666-13-3 (Diphenyl diselenide)
  • Hazard Symbols ToxicT, DangerousN
  • Synonyms Phenyldiselenide (6CI,7CI,8CI);NSC 49763;
  • PSA 0.00000
  • LogP 0.96080

Synthetic route

Phenylselenyl chloride
5707-04-0

Phenylselenyl chloride

N,N,N'-tris(trimethylsilyl)benzamidine
24261-90-3

N,N,N'-tris(trimethylsilyl)benzamidine

A

diphenyl diselenide
1666-13-3

diphenyl diselenide

Conditions
ConditionsYield
In dichloromethane at 23℃; for 3h;A 100%
B 55%
iodoacetophenone
4636-16-2

iodoacetophenone

Benzeneselenol
645-96-5

Benzeneselenol

A

diphenyl diselenide
1666-13-3

diphenyl diselenide

B

acetophenone
98-86-2

acetophenone

Conditions
ConditionsYield
With potassium carbonate In ethanol for 0.25h; Product distribution; Ambient temperature; other iodomethyl ketones;A 100%
B 100%
1-[1-Phenyl-2-((2S,5R)-5-phenylselanylmethyl-tetrahydro-furan-2-yl)-ethyl]-1H-benzotriazole

1-[1-Phenyl-2-((2S,5R)-5-phenylselanylmethyl-tetrahydro-furan-2-yl)-ethyl]-1H-benzotriazole

A

diphenyl diselenide
1666-13-3

diphenyl diselenide

1-[2-((2S,5S)-5-Methyl-tetrahydro-furan-2-yl)-1-phenyl-ethyl]-1H-benzotriazole

1-[2-((2S,5S)-5-Methyl-tetrahydro-furan-2-yl)-1-phenyl-ethyl]-1H-benzotriazole

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene for 1.5h; Heating;A 100%
B 99%
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene for 1.5h; Heating;A 99%
B 98%
Phenylselenyl chloride
5707-04-0

Phenylselenyl chloride

Thallous Phenyl Selenide
72017-00-6

Thallous Phenyl Selenide

A

diphenyl diselenide
1666-13-3

diphenyl diselenide

B

thallous chloride

thallous chloride

Conditions
ConditionsYield
In diethyl ether for 0.00833333h; Ambient temperature;A 100%
B n/a
Benzoyl bromide
618-32-6

Benzoyl bromide

Thallous Phenyl Selenide
72017-00-6

Thallous Phenyl Selenide

A

diphenyl diselenide
1666-13-3

diphenyl diselenide

B

phenyl selenobenzoate
38447-68-6

phenyl selenobenzoate

Conditions
ConditionsYield
In diethyl ether for 1h;A 1%
B 99%
α-(phenylseleno)acetophenone
35050-01-2

α-(phenylseleno)acetophenone

A

diphenyl diselenide
1666-13-3

diphenyl diselenide

B

acetophenone
98-86-2

acetophenone

Conditions
ConditionsYield
With GLUTATHIONE In methanol Product distribution; Mechanism; 0.1 M phosphate buffer, pH=6.9; UV spectra;A 99%
B 64%
1-(naphthalen-2-yl)-2-(phenylselanyl)ethan-1-one
104755-33-1

1-(naphthalen-2-yl)-2-(phenylselanyl)ethan-1-one

A

diphenyl diselenide
1666-13-3

diphenyl diselenide

B

methyl 2-naphthyl ketone
93-08-3

methyl 2-naphthyl ketone

Conditions
ConditionsYield
With GLUTATHIONE In methanol Product distribution; Mechanism; 0.1 M phosphate buffer, pH=6.9;A 99%
B 91%
1-(4-nitrophenyl)-2-(phenylselanyl)ethan-1-one
104755-32-0

1-(4-nitrophenyl)-2-(phenylselanyl)ethan-1-one

A

diphenyl diselenide
1666-13-3

diphenyl diselenide

B

(4-nitrophenyl)ethanone
100-19-6

(4-nitrophenyl)ethanone

Conditions
ConditionsYield
With GLUTATHIONE In methanol Product distribution; Mechanism; 0.1 M phosphate buffer, pH=6.9; differnt quantity of glutathione; relative reactivity to α-(phenylselenenyl)acetophenone;A 99%
B 87%
1-[1-Phenyl-2-((2S,5S)-5-phenylselanylmethyl-tetrahydro-furan-2-yl)-ethyl]-1H-benzotriazole

1-[1-Phenyl-2-((2S,5S)-5-phenylselanylmethyl-tetrahydro-furan-2-yl)-ethyl]-1H-benzotriazole

A

diphenyl diselenide
1666-13-3

diphenyl diselenide

1-[2-((2S,5R)-5-Methyl-tetrahydro-furan-2-yl)-1-phenyl-ethyl]-1H-benzotriazole

1-[2-((2S,5R)-5-Methyl-tetrahydro-furan-2-yl)-1-phenyl-ethyl]-1H-benzotriazole

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene for 1.5h; Heating;A 99%
B 98%
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene for 1.5h; Heating;A 98%
B 97%
(2S,3R)-2-Fluoro-3-hydroxy-5-phenyl-2-phenylselanyl-pentanoic acid ethyl ester

(2S,3R)-2-Fluoro-3-hydroxy-5-phenyl-2-phenylselanyl-pentanoic acid ethyl ester

A

diphenyl diselenide
1666-13-3

diphenyl diselenide

B

(Z)-ethyl 2-fluoro-5-phenylpent-2-enoate
211614-09-4

(Z)-ethyl 2-fluoro-5-phenylpent-2-enoate

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In 1,2-dichloro-ethane at 83℃; for 0.166667h;A 13%
B 99%
2-fluoro-3-hydroxy-2-phenylselanyl-3-(2,4,6-trimethyl-phenyl)-propionic acid ethyl ester

2-fluoro-3-hydroxy-2-phenylselanyl-3-(2,4,6-trimethyl-phenyl)-propionic acid ethyl ester

A

(Z)-2-Fluoro-3-(2,4,6-trimethyl-phenyl)-acrylic acid ethyl ester

(Z)-2-Fluoro-3-(2,4,6-trimethyl-phenyl)-acrylic acid ethyl ester

B

diphenyl diselenide
1666-13-3

diphenyl diselenide

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In 1,2-dichloro-ethane at 20℃; for 0.166667h;A 99%
B 31%
Se-phenyl butaneselenoate
109057-62-7

Se-phenyl butaneselenoate

diphenyl diselenide
1666-13-3

diphenyl diselenide

Conditions
ConditionsYield
With iodine In methanol at 20℃; for 4.5h;99%
Benzeneselenol
645-96-5

Benzeneselenol

Polymer; Monomer(s): 1,2,3-trichloropropane; sodium disulfide

Polymer; Monomer(s): 1,2,3-trichloropropane; sodium disulfide

A

1,2,3-propanetrithiol
4756-13-2

1,2,3-propanetrithiol

B

diphenyl diselenide
1666-13-3

diphenyl diselenide

Conditions
ConditionsYield
at 60 - 70℃; for 0.5h; Reduction; oxidation;A 5.4%
B 98.6%
at 100 - 120℃; for 5h; Reduction; oxidation;A 92.5%
B 95.6%
Benzeneselenol
645-96-5

Benzeneselenol

diphenyl diselenide
1666-13-3

diphenyl diselenide

Conditions
ConditionsYield
With dihydrogen peroxide In ethanol at 0℃; for 0.3h;98%
With dimethyl 2,3-dicyanofumarate In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;98%
With sodium perborate In ethanol at 20℃; for 6h;97%
iodobenzene
591-50-4

iodobenzene

diphenyl diselenide
1666-13-3

diphenyl diselenide

Conditions
ConditionsYield
With selenium; potassium hydroxide In dimethyl sulfoxide at 90℃; for 4h; Time; Solvent; Concentration;98%
With selenium; potassium hydroxide In water at 130℃; for 5h; Green chemistry;98%
With selenium; copper(II) oxide; potassium hydroxide In dimethyl sulfoxide at 90℃; for 1h; Inert atmosphere;96%
benzyl phenyl selenide
18255-05-5

benzyl phenyl selenide

A

diphenyl diselenide
1666-13-3

diphenyl diselenide

B

1,1'-(1,2-ethanediyl)bisbenzene
103-29-7

1,1'-(1,2-ethanediyl)bisbenzene

Conditions
ConditionsYield
at 600℃; under 20 Torr;A 98%
B 92%
phenyl trimethylsilyl selenide
33861-17-5

phenyl trimethylsilyl selenide

A

trimethylsilyl iodide
16029-98-4

trimethylsilyl iodide

B

diphenyl diselenide
1666-13-3

diphenyl diselenide

Conditions
ConditionsYield
With iodineA 98%
B 96%
benzeneseleninic acid
6996-92-5

benzeneseleninic acid

Benzeneselenol
645-96-5

Benzeneselenol

diphenyl diselenide
1666-13-3

diphenyl diselenide

Conditions
ConditionsYield
In ethanol at 0℃; for 1h;98%
benzoyl chloride
98-88-4

benzoyl chloride

Thallous Phenyl Selenide
72017-00-6

Thallous Phenyl Selenide

A

diphenyl diselenide
1666-13-3

diphenyl diselenide

B

phenyl selenobenzoate
38447-68-6

phenyl selenobenzoate

Conditions
ConditionsYield
In diethyl ether for 2.5h;A 1%
B 98%
Thallous Phenyl Selenide
72017-00-6

Thallous Phenyl Selenide

acetyl chloride
75-36-5

acetyl chloride

A

acetyl phenyl selenide
38447-66-4

acetyl phenyl selenide

B

diphenyl diselenide
1666-13-3

diphenyl diselenide

Conditions
ConditionsYield
In diethyl ether for 1h;A 98%
B 1%
aniline
62-53-3

aniline

Se-phenyl 4-methylbenzenecarboselenothioate
120449-42-5

Se-phenyl 4-methylbenzenecarboselenothioate

A

diphenyl diselenide
1666-13-3

diphenyl diselenide

B

4-methylthiobenzanilide
20199-06-8

4-methylthiobenzanilide

Conditions
ConditionsYield
In hexane for 24h; Heating;A 98%
B 68%
2-phenylethanol
60-12-8

2-phenylethanol

1,2-diphenyl-1-phenylseleno-2-ethanone
224627-22-9

1,2-diphenyl-1-phenylseleno-2-ethanone

A

phenyl benzyl ketone
451-40-1

phenyl benzyl ketone

B

diphenyl diselenide
1666-13-3

diphenyl diselenide

C

(2-phenyl-ethyl) phenyl selenide
65275-36-7

(2-phenyl-ethyl) phenyl selenide

Conditions
ConditionsYield
With tributylphosphine In benzene for 4h; Ambient temperature;A 98%
B 8%
C 72%
p-tolyl benzeneselenosulfonate
68819-94-3

p-tolyl benzeneselenosulfonate

Triethylgerman
1188-14-3

Triethylgerman

A

triethylgermyl p-toluenesulfonate
98039-53-3

triethylgermyl p-toluenesulfonate

B

diphenyl diselenide
1666-13-3

diphenyl diselenide

Conditions
ConditionsYield
With air; 2,2'-azobis(isobutyronitrile) In not givenA 93%
B 98%
piperidine
110-89-4

piperidine

Se-phenyl 4-methylbenzenecarboselenothioate
120449-42-5

Se-phenyl 4-methylbenzenecarboselenothioate

A

diphenyl diselenide
1666-13-3

diphenyl diselenide

B

piperidinium 4-methylbenzenecarbodithiolate
42967-76-0

piperidinium 4-methylbenzenecarbodithiolate

Conditions
ConditionsYield
In hexane at 20℃; for 0.5h;A 97%
B 31%
Phenylselenyl chloride
5707-04-0

Phenylselenyl chloride

phenyl trimethylsilyl selenide
33861-17-5

phenyl trimethylsilyl selenide

A

chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

B

diphenyl diselenide
1666-13-3

diphenyl diselenide

Conditions
ConditionsYield
In acetonitrile at 9℃;A 97%
B 93%
Acetyl bromide
506-96-7

Acetyl bromide

Thallous Phenyl Selenide
72017-00-6

Thallous Phenyl Selenide

A

acetyl phenyl selenide
38447-66-4

acetyl phenyl selenide

B

diphenyl diselenide
1666-13-3

diphenyl diselenide

Conditions
ConditionsYield
In diethyl ether for 1h;A 97%
B 1%
tert-butyl phenyl selenide
22233-90-5

tert-butyl phenyl selenide

diphenyl diselenide
1666-13-3

diphenyl diselenide

Conditions
ConditionsYield
sodium perchlorate In acetonitrile97%
phenylselenium trichloride
42572-42-9

phenylselenium trichloride

diphenyl diselenide
1666-13-3

diphenyl diselenide

Conditions
ConditionsYield
With sodium L-ascorbate In methanol; water for 24h;97%
trans-2-<1-(Phenylseleno)benzyl>cyclohexanol
83845-68-5, 83915-67-7

trans-2-<1-(Phenylseleno)benzyl>cyclohexanol

A

diphenyl diselenide
1666-13-3

diphenyl diselenide

B

2-hydroxybenzylidenecyclohexane
34492-42-7

2-hydroxybenzylidenecyclohexane

Conditions
ConditionsYield
With N-chloro-succinimide; 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene 1.) 1h 0 deg C, 2.) 7h room temperature;A 40%
B 97%
Thallous Phenyl Selenide
72017-00-6

Thallous Phenyl Selenide

1-chloroacetophenone
532-27-4

1-chloroacetophenone

A

α-(phenylseleno)acetophenone
35050-01-2

α-(phenylseleno)acetophenone

B

diphenyl diselenide
1666-13-3

diphenyl diselenide

Conditions
ConditionsYield
In diethyl ether for 10h;A 97%
B 1%
diphenyl diselenide
1666-13-3

diphenyl diselenide

benzyl chloride
100-44-7

benzyl chloride

benzyl phenyl selenide
18255-05-5

benzyl phenyl selenide

Conditions
ConditionsYield
With RhCl(PPh3)3; hydrogen; triethylamine In tetrahydrofuran at 50℃; under 760 Torr; for 24h;100%
With ruthenium trichloride; zinc In N,N-dimethyl-formamide at 100℃; for 1h;98%
Stage #1: diphenyl diselenide With 1-butyl-3-methylimidazolium Tetrafluoroborate; zinc at 20℃; Inert atmosphere;
Stage #2: benzyl chloride at 20℃; Inert atmosphere;
93%
diphenyl diselenide
1666-13-3

diphenyl diselenide

1-dodecylbromide
143-15-7

1-dodecylbromide

dodecyl phenyl selenide
42066-69-3

dodecyl phenyl selenide

Conditions
ConditionsYield
With indium(III) bromide; zinc In N,N-dimethyl-formamide at 100℃; for 1h;100%
With ruthenium trichloride; zinc In N,N-dimethyl-formamide at 100℃; for 1h;98%
With RhCl(PPh3)3; hydrogen; triethylamine In tetrahydrofuran at 50℃; under 760 Torr; for 24h;97%
pent-4-enoic acid
591-80-0

pent-4-enoic acid

diphenyl diselenide
1666-13-3

diphenyl diselenide

5-phenylselanylmethyl-dihydro-furan-2-one
65234-93-7

5-phenylselanylmethyl-dihydro-furan-2-one

Conditions
ConditionsYield
With copper(I) trifluoromethanesulfonate benzene; calcium carbonate In dichloromethane at 30℃; for 8h;100%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 30℃;95%
With carbon tetrabromide In dichloromethane for 4h; Irradiation;95%
cyclohexane
110-82-7

cyclohexane

diphenyl diselenide
1666-13-3

diphenyl diselenide

phenylselenocyclohexane
22233-91-6

phenylselenocyclohexane

Conditions
ConditionsYield
With 4-tert-butylpyridine; hydrogen sulfide; oxygen; iron(II) chloride In acetonitrile for 4h; Ambient temperature;100%
With 4-tert-butylpyridine; 2-Picolinic acid; dihydrogen peroxide; triphenylphosphine; iron(II) chloride In acetonitrile at 0℃;99%
With di-tert-butyl peroxide at 120℃; for 18h; Reagent/catalyst;96%
(cyclopent-2-eneyl)acetic acid
13668-61-6

(cyclopent-2-eneyl)acetic acid

diphenyl diselenide
1666-13-3

diphenyl diselenide

(3aα,6a,6aα)-hexahydro-6-(phenylseleno)-2H-cyclopentafuran-2-one
65234-92-6

(3aα,6a,6aα)-hexahydro-6-(phenylseleno)-2H-cyclopentafuran-2-one

Conditions
ConditionsYield
With copper(I) trifluoromethanesulfonate benzene; calcium carbonate In dichloromethane at 30℃; for 7.5h; other acids;100%
With copper(I) trifluoromethanesulfonate benzene; calcium carbonate In dichloromethane at 30℃; for 7.5h;100%
With iodine In acetonitrile at 20℃; for 16h; regioselective reaction;81%
With iodosylbenzene In dichloromethane at 20℃;72%
With ammonium persulfate In acetonitrile at 70℃; for 2h;70%
diphenyl diselenide
1666-13-3

diphenyl diselenide

phenylselenium trichloride
42572-42-9

phenylselenium trichloride

Phenylselenyl chloride
5707-04-0

Phenylselenyl chloride

Conditions
ConditionsYield
In tetrachloromethane at 20℃; for 2h;100%
diphenyl diselenide
1666-13-3

diphenyl diselenide

trans-2-(2-phenylethynyl)-1-cyclohexanol
82031-71-8, 82032-02-8, 138907-21-8

trans-2-(2-phenylethynyl)-1-cyclohexanol

C20H20Se

C20H20Se

Conditions
ConditionsYield
With tributylphosphine In tetrahydrofuran100%
diphenyl diselenide
1666-13-3

diphenyl diselenide

6-benzyloxy-4-methyl-4Z-hexen-1-ol p-toluenesulfonate
73454-44-1

6-benzyloxy-4-methyl-4Z-hexen-1-ol p-toluenesulfonate

(Z)-6-benzyloxy-4-methyl-1-phenylseleno-4-hexene
73454-48-5

(Z)-6-benzyloxy-4-methyl-1-phenylseleno-4-hexene

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol for 2h; Ambient temperature;100%
diphenyl diselenide
1666-13-3

diphenyl diselenide

C16H25ClHgO2
81752-94-5

C16H25ClHgO2

(4aR,8aS)-5,5,8a-Trimethyl-2-methylene-6-phenylselanyl-decahydro-naphthalene-1-carboxylic acid methyl ester

(4aR,8aS)-5,5,8a-Trimethyl-2-methylene-6-phenylselanyl-decahydro-naphthalene-1-carboxylic acid methyl ester

Conditions
ConditionsYield
In benzene for 0.216667h; Irradiation;100%
diphenyl diselenide
1666-13-3

diphenyl diselenide

(1R,4aR,8aS)-5,5,8a-Trimethyl-2-oxo-6-phenylselanyl-decahydro-naphthalene-1-carboxylic acid methyl ester
106625-45-0, 115927-80-5

(1R,4aR,8aS)-5,5,8a-Trimethyl-2-oxo-6-phenylselanyl-decahydro-naphthalene-1-carboxylic acid methyl ester

Conditions
ConditionsYield
In benzene for 0.216667h; Irradiation;100%
diphenyl diselenide
1666-13-3

diphenyl diselenide

C17H27ClHgO4
98264-20-1

C17H27ClHgO4

(1'R,4'aS,8'aR)-5',5',8'a-Trimethyl-6'-phenylselanyl-octahydro-spiro[[1,3]dioxolane-2,2'-naphthalene]-1'-carboxylic acid methyl ester
98264-21-2, 98303-05-0, 124377-25-9

(1'R,4'aS,8'aR)-5',5',8'a-Trimethyl-6'-phenylselanyl-octahydro-spiro[[1,3]dioxolane-2,2'-naphthalene]-1'-carboxylic acid methyl ester

Conditions
ConditionsYield
In benzene for 0.216667h; Irradiation;100%
diphenyl diselenide
1666-13-3

diphenyl diselenide

Conditions
ConditionsYield
In benzene for 0.216667h; Irradiation;100%
diphenyl diselenide
1666-13-3

diphenyl diselenide

Tellurobenzoic acid Te-(4-fluoro-phenyl) ester
143565-02-0

Tellurobenzoic acid Te-(4-fluoro-phenyl) ester

phenyl selenobenzoate
38447-68-6

phenyl selenobenzoate

Conditions
ConditionsYield
In benzene at 8℃; for 1.5h; Irradiation;100%
In benzene at 8℃; for 1.5h; Mechanism; Irradiation; other acyl tellurides; other radical traps; other termolysis conditions;100%
In benzene at 8℃; for 1.5h; Irradiation;93%
diphenyl diselenide
1666-13-3

diphenyl diselenide

10-bromo-isoborneol

10-bromo-isoborneol

(1S,2R,4R)-7,7-Dimethyl-1-phenylselanylmethyl-bicyclo[2.2.1]heptan-2-ol
156832-25-6

(1S,2R,4R)-7,7-Dimethyl-1-phenylselanylmethyl-bicyclo[2.2.1]heptan-2-ol

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol Heating;100%
With sodium tetrahydroborate In ethanol for 6h; Heating;100%
diphenyl diselenide
1666-13-3

diphenyl diselenide

benzyl bromide
100-39-0

benzyl bromide

benzyl phenyl selenide
18255-05-5

benzyl phenyl selenide

Conditions
ConditionsYield
With sodium dihydrogenphosphate; zinc In water; acetonitrile for 1h;100%
With indium In tetrahydrofuran; water at 25℃; for 24h;98%
Stage #1: diphenyl diselenide With zinc In acetonitrile at 65℃; for 1h;
Stage #2: benzyl bromide In water; acetonitrile at 65℃; for 0.2h;
98%
diphenyl diselenide
1666-13-3

diphenyl diselenide

ethyl iodide
75-03-6

ethyl iodide

ethyl phenyl selenide
17774-38-8

ethyl phenyl selenide

Conditions
ConditionsYield
With dipotassium hydrogenphosphate; zinc In water; acetonitrile for 1h;100%
With dipotassium hydrogenphosphate; zinc In water; acetonitrile for 1h; Product distribution; Further Variations:; Reaction partners; Reagents; Solvents;100%
With sodium tetrahydroborate In acetonitrile for 0.0833333h; pH=7; pH-value;100%
diphenyl diselenide
1666-13-3

diphenyl diselenide

chloroacetic acid ethyl ester
105-39-5

chloroacetic acid ethyl ester

ethyl 2-(phenylselanyl)acetate
51364-94-4

ethyl 2-(phenylselanyl)acetate

Conditions
ConditionsYield
Stage #1: diphenyl diselenide With sodium tetrahydroborate In ethanol at 0℃; for 0.166667h; Inert atmosphere;
Stage #2: chloroacetic acid ethyl ester In ethanol for 1h; Inert atmosphere;
100%
Stage #1: diphenyl diselenide With sodium tetrahydroborate; ethanol at 0 - 25℃; for 1h;
Stage #2: chloroacetic acid ethyl ester at 25℃; for 2h;
98%
Stage #1: diphenyl diselenide With sodium tetrahydroborate In ethanol for 0.166667h;
Stage #2: chloroacetic acid ethyl ester In ethanol at 50 - 55℃; for 0.75h;
94%
diphenyl diselenide
1666-13-3

diphenyl diselenide

1-phenyl-2-bromoethane
103-63-9

1-phenyl-2-bromoethane

(2-phenyl-ethyl) phenyl selenide
65275-36-7

(2-phenyl-ethyl) phenyl selenide

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol for 2h; Ambient temperature;100%
With zinc In N,N-dimethyl-formamide at 100℃; for 2h; Inert atmosphere;94%
With indium iodide In dichloromethane at 20℃; for 1h;89%
With sodium tetrahydroborate In ethanol; 1,2-dichloro-ethane at 20℃; Reduction; alkylation;79%
With triphenylphosphine; 1-pentyl-3-methylimidazolium bromide at 75℃; for 5.5h;75%
diphenyl diselenide
1666-13-3

diphenyl diselenide

allyl bromide
106-95-6

allyl bromide

allyl phenyl selenide
14370-82-2

allyl phenyl selenide

Conditions
ConditionsYield
With sodium dihydrogenphosphate; zinc In water; acetonitrile for 1h;100%
With sodium tetrahydroborate; ethanol In tetrahydrofuran at 0℃; for 0.416667h; Inert atmosphere;98%
Stage #1: diphenyl diselenide With indium iodide; 1-butyl-3-methylimidazolium Tetrafluoroborate at 20℃; for 0.0833333h; Inert atmosphere;
Stage #2: allyl bromide at 20℃;
97%
diphenyl diselenide
1666-13-3

diphenyl diselenide

1-chloro-2,4-dinitro-benzene
97-00-7

1-chloro-2,4-dinitro-benzene

(2,4-dinitrophenyl)(phenyl)selane
67516-66-9

(2,4-dinitrophenyl)(phenyl)selane

Conditions
ConditionsYield
With borax; N-Acetylcysteine In methanol; water for 1h; Ambient temperature;100%
With sodium hydroxide; cetyltrimethylammonim bromide; Aminoiminomethanesulfinic acid In tetrahydrofuran for 4h; Heating;87%
With sodium hydroxide; Aminoiminomethanesulfinic acid; cetyltrimethylammonim bromide In tetrahydrofuran; water for 4h; Heating;87%
Stage #1: diphenyl diselenide With sodium tetrahydroborate In ethanol Inert atmosphere;
Stage #2: 1-chloro-2,4-dinitro-benzene In ethanol; dimethyl sulfoxide for 12h; Reflux; Inert atmosphere;
diphenyl diselenide
1666-13-3

diphenyl diselenide

isopropyl bromide
75-26-3

isopropyl bromide

(phenylseleno)-2-propane
22233-89-2

(phenylseleno)-2-propane

Conditions
ConditionsYield
With sodium tetrahydroborate In 1,2-dimethoxyethane at 20℃; for 12h; Inert atmosphere;100%
With indium iodide In dichloromethane at 20℃; for 1h;80%
With N,N,N,N,N,N-hexamethylphosphoric triamide; samarium diiodide In tetrahydrofuran for 3h; Heating;78%
With triphenylphosphine; 1-pentyl-3-methylimidazolium bromide at 75℃; for 6h;72%
diphenyl diselenide
1666-13-3

diphenyl diselenide

(1S,6R,8R,10S)-8-(3-Chloropropyl)-10-methoxy-3,3,9,9-tetramethyl-2,4,7-trioxabicyclo[4.4.0]decane
259735-93-8

(1S,6R,8R,10S)-8-(3-Chloropropyl)-10-methoxy-3,3,9,9-tetramethyl-2,4,7-trioxabicyclo[4.4.0]decane

(1S,6R,8R,10S)-10-Methoxy-3,3,9,9-tetramethyl-8-(3-phenylselenylpropyl)-2,4,7-trioxabicyclo[4.4.0]decane
259735-94-9

(1S,6R,8R,10S)-10-Methoxy-3,3,9,9-tetramethyl-8-(3-phenylselenylpropyl)-2,4,7-trioxabicyclo[4.4.0]decane

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol for 0.666667h; Substitution; Heating;100%
diphenyl diselenide
1666-13-3

diphenyl diselenide

tert-Butyl iodide
558-17-8

tert-Butyl iodide

tert-butyl phenyl selenide
22233-90-5

tert-butyl phenyl selenide

Conditions
ConditionsYield
With zinc In acetonitrile for 0.0833333h; pH=14; Barbier Coupling Reaction;100%
With zinc In dichloromethane at 20℃; for 5h;87%
With indium iodide In dichloromethane at 20℃; for 0.416667h;85%
diphenyl diselenide
1666-13-3

diphenyl diselenide

cinnamyl chloride
2687-12-9

cinnamyl chloride

cinnamyl phenyl selenide
17417-76-4

cinnamyl phenyl selenide

Conditions
ConditionsYield
With potassium dihydrogenphosphate; zinc In water; acetonitrile for 1h;100%
diphenyl diselenide
1666-13-3

diphenyl diselenide

[4-(tert-butyldimethylsiloxy)-5-methoxy-3-(3',7'-dimethyl-6'-epoxy-2'-octenyl)benzyloxy]-tert-butyldimethylsilane
474970-91-7

[4-(tert-butyldimethylsiloxy)-5-methoxy-3-(3',7'-dimethyl-6'-epoxy-2'-octenyl)benzyloxy]-tert-butyldimethylsilane

[4-(tert-butyldimethylsiloxy)-5-methoxy-3-(3',7'-dimethyl-7'-hydroxy-6'-phenylselenyl-2'-octenyl)benzyloxy]-tert-butyldimethylsilane
474970-93-9

[4-(tert-butyldimethylsiloxy)-5-methoxy-3-(3',7'-dimethyl-7'-hydroxy-6'-phenylselenyl-2'-octenyl)benzyloxy]-tert-butyldimethylsilane

Conditions
ConditionsYield
With sodium tetrahydroborate100%
Stage #1: diphenyl diselenide With sodium tetrahydroborate In ethanol at 0℃; for 0.4h;
Stage #2: [4-(tert-butyldimethylsiloxy)-5-methoxy-3-(3',7'-dimethyl-6'-epoxy-2'-octenyl)benzyloxy]-tert-butyldimethylsilane In ethanol at 0℃; for 48h; Further stages.;
100%
diphenyl diselenide
1666-13-3

diphenyl diselenide

1-(5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-4-ethoxy-1H-pyrimidin-2-one
661463-96-3

1-(5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-4-ethoxy-1H-pyrimidin-2-one

1-(5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-4-ethoxy-6-phenylseleno-1H-pyrimidin-2-one

1-(5-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-4-ethoxy-6-phenylseleno-1H-pyrimidin-2-one

Conditions
ConditionsYield
With lithium hexamethyldisilazane In tetrahydrofuran at -80℃; for 1h;100%

Diphenyl diselenide Chemical Properties

Molecular Formula: C12H10Se2
Molar mass: 312.1278 g/mol
EINECS: 216-780-2
Flash Point: 182 °C
Boiling Point: 377.3 °C at 760 mmHg
Vapour Pressure: 1.48E-05 mmHg at 25°C
Product categories of Bis(phenylselenide) (1666-13-3): Pharmaceutical Intermediates;Classes of Metal Compounds;Aromatic Phenylacetic Acids and Derivatives;Semimetal Compounds
Structure of Bis(phenylselenide) (1666-13-3):
             
H-Bond Donor: 0
H-Bond Acceptor: 0
IUPAC Name: Phenyldiselanylbenzene
Canonical SMILES: C1=CC=C(C=C1)[Se][Se]C2=CC=CC=C2
InChI: InChI=1S/C12H10Se2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10H 
InChIKey: YWWZCHLUQSHMCL-UHFFFAOYSA-N

Diphenyl diselenide Uses

 Bis(phenylselenide) (1666-13-3) has been used for the synthesis of Allyl alcohol , Allyl ether , Ethyl acetate , and α, β-Unsaturated carbonyl compounds .

Diphenyl diselenide Toxicity Data With Reference

1.    

ivn-mus LD50:28 mg/kg

    CSLNX*    U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#05657 .

You can see actual entry in RTECS for complete information about Bis(phenylselenide) (1666-13-3).

Diphenyl diselenide Consensus Reports

Reported in EPA TSCA Iventory. Selenium and its compounds are on the Community Right-To-Know List.

Diphenyl diselenide Safety Profile

Poison by intravenous route. See also SELENIUM COMPOUNDS. When heated to decomposition it emits toxic fumes of Se.
 

Hazard Codes: T,N
Risk Statements:
23:  Toxic by inhalation
25:  Toxic if swallowed
33:  Danger of cumulative effects
50:  Very Toxic to aquatic organisms
53:  May cause long-term adverse effects in the aquatic environment
Safety Statements:
20:  When using, do not eat or drink
21:  When using, do not smoke
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
28A     After contact with skin, wash immediately with plenty of water.
39:  Wear eye/face protection
45:  In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
60:  This material and/or its container must be disposed of as hazardous waste
61:  Avoid release to the environment. Refer to special instructions safety data sheet

Diphenyl diselenide Standards and Recommendations

OSHA PEL: TWA 0.2 mg(Se)/m3
ACGIH TLV: TWA 0.2 mg(Se)/m3
DFG MAK: 0.1 mg(Se)/m3

Diphenyl diselenide Specification

 Bis(phenylselenide) (1666-13-3) also can be called Diphenyl diselenide ; Phenyl diselenide (8CI) ; Diphenyldiselenide ; Diselenide, diphenyl ; Diselane, 1,2-diphenyl- .It is hazardous,so the first aid measures and others should be known.Such as: When on the skin: first,should  flush skin with plenty of water immediatelyfor at least 15 minutes while removing contaminated clothing. Secondly,Get shoesmedical aid . Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids.Then get medical aid soon.While ,it's Inhaled: Remove from exposure and move to fresh air immediately.Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid.Then you have the ingesting of the product : Wash mouth out with water,and get medical aid immediately.
In addition, Bis(phenylselenide) (1666-13-3)  is not compatible with incompatible materials,and you must not take it with reducing agents, halogens, and incompatible materials. And also prevent it to broken down into hazardous decomposition products: selenium/selenium oxides,carbon dioxide,carbon monoxide.

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