7101-31-7

Basic information

• Product Name: Dimethyldiselenide
• Synonyms: (CH3Se)2;1,2-Dimethyldiselane;Diselenide, dimethyl;Methyldiselanylmethane;Dimethyl perdiselenide;Dimethyl perselenide;Dimethyldiselenium;Dimethyldiselenide,99+%
• CAS NO: 7101-31-7
• Molecular Formula: C₂H₆Se₂
• Molecular Weight: 187.99
• EINECS: 230-410-7
• Product Categories: Pharmaceutical Intermediates;Classes of Metal Compounds;Se (Selenium) Compounds;Semimetal Compounds
• Mol File: 7101-31-7.mol
• Article Data: 34

Chemical Properties

• Melting Point: -82.2 °C
• Boiling Point: 155-157 °C(lit.)
• Flash Point: 140 °F
• Appearance: /liquid
• Density: 1.987 g/mL at 25 °C(lit.)
• Vapor Pressure: 3.34mmHg at 25°C
• Refractive Index: n20/D 1.6388(lit.)
• Storage Temp.: 0-6°C
• Water Solubility: Reacts with water.
• Sensitive: Air & Moisture Sensitive
• Stability: Stable. Combustible. Incompatible with strong oxidizing agents, strong acids.
• CAS DataBase Reference: Dimethyldiselenide(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethyldiselenide(7101-31-7)
• EPA Substance Registry System: Dimethyldiselenide(7101-31-7)

Safety Data

• Hazard Codes: T,N
• Statements: 23/24/25-50/53-33-23/25
• Safety Statements: 23-36/37/39-45-61-60-28A-20/21-28
• RIDADR: UN 2929 6.1/PG 2
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 7101-31-7(Hazardous Substances Data)

Usage

Chemical Properties

orange liquid with a very unpleasant smell

Uses

Dimethyl diselenide is a powerful reagent used for identification of distonic radical cations

General Description

Dimethyl diselenide is a volatile selenium species and its determination in biological samples by HPLC-inductively coupled argon plasma mass spectrometry was reported. Selenium alkylation with dimethyl diselenide was reported by solid-phase microextraction gas chromatography-mass spectrometry.

InChI:InChI=1/C2H6Se2/c1-3-4-2/h1-2H3

Synthetic route

selenothiobenzoic acid Se-methyl ester (136970-32-6) + dimethyl amine (124-40-3) → dimethyl diselenide (7101-31-7) + N,N-dimethylthiobenzamide (15482-60-7)

Conditions	Yield
In dichloromethane	A n/a B 100%

1-Methylselanyl-2-phenyl-ethanethione (136970-31-5) + dimethyl amine (124-40-3) → dimethyl diselenide (7101-31-7) + N,N-dimethyl-2-phenylethanethioamide (17709-95-4)

Conditions	Yield
In dichloromethane	A n/a B 100%

(4-Methoxy-phenyl)-methylselanyl-methanethione (136992-18-2) + dimethyl amine (124-40-3) → dimethyl diselenide (7101-31-7) + 4-methoxy-N,N-dimethylbenzenecarbothioamide (15482-63-0)

Conditions	Yield
In dichloromethane	A n/a B 100%

methaneseleninic acid (28274-57-9) + dimedone (126-81-8) → dimethyl diselenide (7101-31-7)

Conditions	Yield
In d(4)-methanol for 0.5h;	100%

methyl iodide (74-88-4) → dimethyl diselenide (7101-31-7)

Conditions	Yield
With potassium hydroxide; selenium; hydrazine hydrate In water at 30 - 32℃;	98%
With potassium hydroxide; selenium(IV) oxide; hydrazine hydrate In water at 30 - 32℃;	95%
With selenium; sodium tetrahydroborate In ethanol; N,N-dimethyl-formamide for 1h;	82%

1-(4-methylphenyl)-1,1-bis(methylseleno)ethane (103971-57-9) → dimethyl diselenide (7101-31-7) + 1-Methyl-4-(1-methylselanyl-ethyl)-benzene (75155-29-2)

Conditions	Yield
With methyl selenide; zinc(II) chloride In dichloromethane for 15h; Ambient temperature;	A n/a B 95%

dimethyl sulfate (77-78-1) → dimethyl diselenide (7101-31-7)

Conditions	Yield
With sodium hydroxide; selenium; tetrabutylammomium bromide; hydrazine hydrate In water at 15 - 20℃;	90%
With potassium hydroxide; selenium; sodium hydrogensulfite In water Heating;	73%
With sodium hydroxide; selenium; hydrazine hydrate In water 1.) room temp., 7 h, 2) 15 --> 20 deg C;	69%
With sodium hydroxide; selenium; rongalite In water

methyl bromide (74-83-9) → dimethyl diselenide (7101-31-7)

Conditions	Yield
With sodium hydroxide; selenium; hydrazine hydrate In N,N-dimethyl-formamide 1.) room temp., 6 h;	88%
With disodium diselenide

methyl selenide (6486-05-1) → dimethyl diselenide (7101-31-7)

Conditions	Yield
With sodium perborate In ethanol at 20℃; for 5h;	86%
With potassium hydroxide; dihydrogen peroxide 2.) ether, 0 deg C, 4 h; Yield given. Multistep reaction;

dimethyl sulfate (77-78-1) → dimethyl diselenide (7101-31-7) + dimethyl triselenide (22009-80-9)

Conditions	Yield
With selenium; sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h;	A 72% B n/a

methyl iodide (74-88-4) → dimethylselenide (593-79-3) + dimethyl diselenide (7101-31-7)

Conditions	Yield
With potassium hydroxide; selenium; hydrazine hydrate at 35 - 40℃;	A 67% B 12%

methyl iodide (74-88-4) → dimethyl diselenide (7101-31-7) + dimethyl triselenide (22009-80-9)

Conditions	Yield
With selenium; sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h;	A 60% B n/a

diiodomethane (75-11-6) → dimethyl diselenide (7101-31-7) + N,N-diethyl selenoformamide

Conditions	Yield
With selenium; sodium hydride; diethylamine In N,N,N,N,N,N-hexamethylphosphoric triamide at 120℃; for 3h;	A n/a B 48%

diiodomethane (75-11-6) + diethylamine (109-89-7) → dimethyl diselenide (7101-31-7) + N,N-diethyl selenoformamide

Conditions	Yield
With selenium; sodium hydride In N,N,N,N,N,N-hexamethylphosphoric triamide at 120℃; for 3h;	A n/a B 48%

diethylamine (109-89-7) + 1,1-dibromomethane (74-95-3) → dimethyl diselenide (7101-31-7) + N,N-diethyl selenoformamide

Conditions	Yield
With selenium; sodium hydride In N,N,N,N,N,N-hexamethylphosphoric triamide at 130℃; for 3h;	A n/a B 47%

1,1-dibromomethane (74-95-3) → dimethyl diselenide (7101-31-7) + N,N-diethyl selenoformamide

Conditions	Yield
With selenium; sodium hydride; diethylamine In N,N,N,N,N,N-hexamethylphosphoric triamide at 130℃; for 3h;	A n/a B 47%

dichloromethane (75-09-2) → dimethyl diselenide (7101-31-7) + N,N-diethyl selenoformamide

Conditions	Yield
With selenium; sodium hydride; diethylamine In N,N,N,N,N,N-hexamethylphosphoric triamide at 120℃; for 4h;	A n/a B 40%

dichloromethane (75-09-2) + diethylamine (109-89-7) → dimethyl diselenide (7101-31-7) + N,N-diethyl selenoformamide

Conditions	Yield
With selenium; sodium hydride In N,N,N,N,N,N-hexamethylphosphoric triamide at 120℃; for 4h;	A n/a B 40%

dimethyl sulfoxide (67-68-5) → dimethylsulfide (75-18-3) + dimethyl diselenide (7101-31-7) + Dimethyldisulphide (624-92-0) + dimethylselenenyl sulfide (41884-42-8)

Conditions	Yield
With potassium hydroxide; selenium; water at 110℃; for 6h; Further byproducts given;	A 8.2% B 0.2% C 3.3% D 0.5%
With potassium hydroxide; selenium; water at 110℃; for 6h; Further byproducts given;	A 8.2% B 0.2% C 3.3% D 0.2%

dimethyl sulfoxide (67-68-5) → dimethylsulfide (75-18-3) + dimethyl diselenide (7101-31-7) + Dimethyldisulphide (624-92-0) + methyl methylthiomethyl selenide (70873-58-4)

Conditions	Yield
With potassium hydroxide; selenium; water at 110℃; for 6h; Further byproducts given;	A 8.2% B 0.2% C 3.3% D 0.1%

tetrachloromethane (56-23-5) + methyl selenide (6486-05-1) → dimethyl diselenide (7101-31-7) + trimethyl orthoselenoformate (66622-20-6)

Conditions	Yield
reagiert als Natriumsalz;

potassium methyl sulfate (562-54-9) → dimethyl diselenide (7101-31-7)

Conditions	Yield
With potassium diselenide

sodium methyl sulfate (512-42-5) → dimethylselenide (593-79-3) + dimethyl diselenide (7101-31-7)

Conditions	Yield
With phosphorus pentaselenide

dimethyl sulfate (77-78-1) → dimethylselenide (593-79-3) + dimethyl diselenide (7101-31-7)

Conditions	Yield
With potassium diselenide; water
With disodium diselenide; water at 100℃;

methyl selenide (6486-05-1) + methaneseleninic acid (28274-57-9) → dimethyl diselenide (7101-31-7)

Conditions	Yield
Yield given. Multistep reaction;

2,2-bis(methylseleno)undecane (66030-43-1) → dimethyl diselenide (7101-31-7) + methyl nonyl ketone (112-12-9)

Conditions	Yield
With sulfuric acid at 20℃; for 0.5h; Yield given;
With sulfuric acid at 20℃; for 0.5h; transformation of selenoacetals to carbonyl compounds;

trimethylsulphonium iodide (2181-42-2) → dimethyl diselenide (7101-31-7)

Conditions	Yield
With sodium hydroxide; selenium; hydrazine hydrate 1.) 6 h, room temperature, water, 2.) room temperature, water; Yield given. Multistep reaction;

α-(methylseleno)-p-nitrostyrene (76573-17-6) → dimethyl diselenide (7101-31-7) + methyl selenide (6486-05-1) + (methylseleno)acetal of p-nitroacetophenone + O,Se-dimethylacetal of p-nitroacetophenone

Conditions	Yield
With sulfuric acid In methanol
With sulfuric acid In methanol Title compound not separated from byproducts;
With sulfuric acid In methanol Title compound not separated from byproducts;

C5H12SeTe (120157-91-7) → dimethyl diselenide (7101-31-7) + dibutyl ditelluride (77129-69-2)

dimethyl diselenide (7101-31-7) + C42H64B2N4 → C33H42BN2Se2

Conditions	Yield
In benzene-d6 at 20℃;	100%

dimethyl diselenide (7101-31-7) + 1,3-dibromo-5-methoxy-2-((4-methoxyphenyl)ethynyl)benzene → (3-bromo-5-methoxy-2-((4-methoxyphenyl)ethynyl)phenyl)(methyl)selane

Conditions	Yield
Stage #1: 1,3-dibromo-5-methoxy-2-((4-methoxyphenyl)ethynyl)benzene With n-butyllithium In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere; Stage #2: dimethyl diselenide In tetrahydrofuran at -78 - 20℃; for 3h; Inert atmosphere;	100%

dimethyl diselenide (7101-31-7) + 2-Fluoro-4-(trifluoromethyl)benzaldehyde (89763-93-9) → 2-(methylselanyl)-4-(trifluoromethyl)benzaldehyde

Conditions	Yield
Stage #1: dimethyl diselenide With 1,4-dithiothreitol In N,N-dimethyl-formamide at 25℃; for 0.5h; Inert atmosphere; Stage #2: 2-Fluoro-4-(trifluoromethyl)benzaldehyde In N,N-dimethyl-formamide at 25℃; for 0.25h; Inert atmosphere; Stage #3: With 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 25℃; for 0.25h; Inert atmosphere;	100%

dimethyl diselenide (7101-31-7) + ethene (74-85-1) → 1-bromo-2-(methylseleno)ethane (76573-12-1)

Conditions	Yield
With bromine In dichloromethane at 0℃;	99%

dimethyl diselenide (7101-31-7) → C2H6S2Se2

Conditions	Yield
With α,α-diphenylbenzenemethanesulfenyl chloride In chloroform at 20℃; for 0.0833333h;	98%

dimethyl diselenide (7101-31-7) + chloroacetic acid ethyl ester (105-39-5) → ethyl 2-(methylselanyl)acetate (80920-09-8)

Conditions	Yield
With sodium tetrahydroborate In ethanol at 0℃; for 1h;	98%

dimethyl diselenide (7101-31-7) + uracil (66-22-8) → 5-(methylselanyl)pyrimidine-2,4(1H,3H)-dione

Conditions	Yield
With dihydrogen peroxide; sodium iodide In dimethyl sulfoxide at 50℃; for 3h; Schlenk technique;	98%
With dihydrogen peroxide; sodium iodide In dimethyl sulfoxide at 50℃;	91%

dimethyl diselenide (7101-31-7) → C2H6S3Se2

Conditions	Yield
With α,α-diphenylbenzenemethanesulfenyl chloride In chloroform at 20℃; for 0.0833333h;	96%

dimethyl diselenide (7101-31-7) + 2,2'-O-anhydro-1-<5'-O-(4,4'-dimethoxytrityl)-β-D-arabinofuranosyl>uracil (173170-12-2) → 5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-2'-Se-methoxyuridine (393802-82-9)

Conditions	Yield
Stage #1: dimethyl diselenide With sodium tetrahydroborate In tetrahydrofuran; ethanol Stage #2: 2,2'-O-anhydro-1-<5'-O-(4,4'-dimethoxytrityl)-β-D-arabinofuranosyl>uracil In tetrahydrofuran; ethanol at 20℃; for 3h; Further stages.;	96%
With sodium tetrahydroborate In tetrahydrofuran; ethanol at 20℃; for 2h;	92%

2-chloromethyl-3-chloroprop-1-ene (1871-57-4) + dimethyl diselenide (7101-31-7) → 3-methylseleno-2-methyl-selenomethyl-1-propene (188245-07-0)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide	95%
With sodium hydride 1.) DMF, 20 deg C, 1 h, 2.) DMF, 20 deg C, 2 h; Yield given. Multistep reaction;

(pentamethylcyclopentadienyl)(dicarbonyl)iridium(I) (32660-96-1) + dimethyl diselenide (7101-31-7) → (C5(CH3)5)Ir(CO)(SeCH3)2 (217181-11-8)

Conditions	Yield
In tetrahydrofuran byproducts: CO; Irradiation (UV/VIS); Ar-atmosphere; irradiation of equimolar amts. (15°C, 40 min); evapn. (vac.), chromy. (SiO2, CH2Cl2/pentane=1:1), recrystn. (CHCl3/hexane, -25°C);	95%

dimethyl diselenide (7101-31-7) + benzaldehyde (100-52-7) → 4-(methylselanyl)benzaldehyde (35729-40-9)

Conditions	Yield
Stage #1: dimethyl diselenide With sodium tetrahydroborate In ethanol at 20℃; for 0.333333h; Inert atmosphere; Stage #2: benzaldehyde In ethanol at 150℃; for 2h;	95%

dimethyl diselenide (7101-31-7) + 2-nitro-4-methoxybenzoic acid (33844-21-2) → (4-methoxy-2-nitrophenyl)(methyl)selane

Conditions	Yield
With 1,10-Phenanthroline; oxygen; copper diacetate; potassium carbonate In toluene at 150℃; under 760.051 Torr; for 24h; Schlenk technique; Sealed tube;	95%
With 1,10-Phenanthroline; oxygen; copper diacetate; potassium carbonate In toluene at 140℃; for 24h;	85%

dimethyl diselenide (7101-31-7) + (E)-methyl 2-(azidomethyl)-5-phenylpent-2-en-4-ynoate (1228932-02-2) → methyl 5-(methylselanyl)-6-phenylnicotinate

Conditions	Yield
With copper dichloride In acetonitrile at 0℃; for 1h;	95%

dimethyl diselenide (7101-31-7) + N6-benzoyl-2',3'-O-isopropylidene-5'-O-(triethylsilyl)adenosine (292642-43-4) → N6-benzoyl-2',3'-O-isopropylidene-8-(methylseleno)-5'-O-(triethylsilyl)adenosine

Conditions	Yield
With 4-toluenesulfonyl azide; lithium diisopropyl amide In tetrahydrofuran; hexane at -78 - 0℃;	94%

dimethyl diselenide (7101-31-7) + 3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propanol methanesulfonate → 5-(3-(methylselanyl)propyl)-10,11-dihydro-5H-dibenzo[b,f]azepine (1425793-98-1)

Conditions	Yield
Stage #1: dimethyl diselenide With sodium tetrahydroborate; ethanol In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 3-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)propanol methanesulfonate In tetrahydrofuran at 20℃; for 0.666667h; Inert atmosphere;	94%

1,3-di-tert-butyl-2,2-dimethyl-1,3,2,4-diazasilagermaetidine (84806-15-5) + dimethyl diselenide (7101-31-7) → [Me2Si(Nt-Bu2)Ge{SeMe}2]

Conditions	Yield
In hexane at 70℃; for 1h;	94%

dimethyl diselenide (7101-31-7) + dichloromethane (75-09-2) → bis(methylselanyl)methane (56051-03-7)

Conditions	Yield
With sodium hydroxide; hydrazine hydrate; tetraethylammonium chloride In N,N-dimethyl-formamide	93%

dimethyl diselenide (7101-31-7) → bis(methylseleno) sulfide

Conditions	Yield
With tritylsulfenyl chloride In chloroform at 20℃; for 0.166667h;	93%

dimethyl diselenide (7101-31-7) + N,N-dimethyl-2-(2-phenylethynyl)aniline (54655-08-2) → 1-methyl-3-(methylselanyl)-2-phenyl-1H-indole (1346165-05-6)

Conditions	Yield
With iodine; iron In acetonitrile at 80℃; for 3h; Inert atmosphere;	93%

1,2,3,3-tetrachlorocyclopropene (6262-42-6) + dimethyl diselenide (7101-31-7) → C6H9Se3(1+)*Cl6Sb(1-)

Conditions	Yield
With antimony(III) chloride In dichloromethane at 20℃;	92%

Upstream product

• 512-42-5 sodium methyl sulfate 
• 74-83-9 methyl bromide 
• 6486-05-1 methyl selenide 
• 28274-57-9 methaneseleninic acid 
• 66030-43-1 2,2-bis(methylseleno)undecane 
• 2181-42-2 trimethylsulphonium iodide 
• 67-68-5 dimethyl sulfoxide 
• 120157-91-7 C₅H₁₂SeTe 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 75-11-6 diiodomethane 
• 75-09-2 dichloromethane 
• 35450-20-5 (methylseleno)dimethylborane 
• 1227476-15-4 Azobenzene 

Downstream Products

• 55021-76-6 Methyl-propyl-selenid 
• 28274-57-9 methaneseleninic acid 
• 75772-21-3 1-chloro-4-<(methylseleno)methyl>benzene 
• 84451-35-4 1,2-bis(methylseleno)benzene 
• 35167-28-3 vinyl phenyl selenide 
• 93370-41-3 Allyl-methyl-selenid 
• 144090-34-6 trans-1,2-bis(methylseleno)cyclohexane 
• 120041-65-8 methyl(2,4,6-tri-t-butylphenyl)-selenide 
• 88141-36-0 Methyl 2,4,6-triisopropylphenyl selenide 
• 50499-86-0 2,3,6,7-tetramethoxyselenananthrene 
• 5925-78-0 benzyl methyl selenide 
• 101-81-5 Diphenylmethane 
• 51678-24-1 2,4-diphenylselenophene 

Relevant articles and documents

Vibrational spectra and structure of dimethyl diselenide and dimethyl diselenide-d6

The vibrational behavior of the dimethyl diselenide and dimethyl diselenide-rfe molecules has been studied in the infrared region (4000-70 cm-1) and by Raman shifts (4000-50 cm-1). The molecule has been found to belong to point group C2. The fundamental vibrations, with the exception of the methyl torsions, have been assigned and supported by a normal-coordinate analysis.

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.

Continuous Electrochemical Synthesis of Iso-Coumarin Derivatives from o-(1-Alkynyl) Benzoates under Metal- and Oxidant-Free

A non-oxidant and metal-free strategy for synthesizing iso-coumarin by using a continuous electrochemical microreactor to initiate an oxidative cyclization reaction of o-(1-alkynyl) benzoate and radicals. This efficient and clean continuous electrosynthesis method not only avoids the complicated gas protection operation and production of by-products in the batch processes, but also help to overcome the difficulty that batch metal catalysis and electrocatalysis are difficult to scale up, and has the potential for pilot-scale experiment.

Preparation method of high-purity selenomethionine

The invention discloses a preparation method of high-purity selenomethionine. The method comprises following steps: (1), synthesis of the dimethyl diselenide; (2), purification of dimethyl diselenide;(3), synthesis of crude selenomethionine sodium salt; and (4), purification of crude selenomethionine sodium salt. The yield of selenium in the selenomethionine prepared with the preparation method is larger than or equal to 80%, the selenomethionine content is larger than or equal to 99.5%, and the economic benefits are significant.