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Cas Database

1482-82-2

1482-82-2

Identification

  • Product Name:Diselenide,bis(phenylmethyl)

  • CAS Number: 1482-82-2

  • EINECS:

  • Molecular Weight:340.185

  • Molecular Formula: C14H14Se2

  • HS Code:29310099

  • Mol File:1482-82-2.mol

Synonyms:Benzyldiselenide (6CI,7CI,8CI);Bis(phenylmethyl)diselenide;Dibenzyl diselenide;Dibenzyldiselenium;NSC 44641;NSC 49764;

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Safety information and MSDS view more

  • Pictogram(s):ToxicT, DangerousN

  • Hazard Codes:T,N

  • Signal Word:Danger

  • Hazard Statement:H301 Toxic if swallowedH331 Toxic if inhaled H373 May cause damage to organs through prolonged or repeated exposure H410 Very toxic to aquatic life with long lasting effects

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:TRC
  • Product Description:Dibenzyl Diselenide
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Dibenzyl Diselenide >95.0%(T)
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:1,2-Dibenzyldiselane 95+%
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  • Product Description:1,2-Dibenzyldiselane 95+%
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  • Product Description:1,2-Dibenzyldiselane 95+%
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  • Manufacture/Brand:Crysdot
  • Product Description:1,2-Dibenzyldiselane 97%
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  • Manufacture/Brand:Crysdot
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:Dibenzyl diselenide
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:Dibenzyl diselenide
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Relevant articles and documentsAll total 86 Articles be found

Reactions of selenobenzamide and alkyl halides. Synthesis of dialkyl selenides and diselenides

Zhang, Xiao-Bo,Ruan, Ming-De,Fan, Wei-Qiang

, p. 4665 - 4670 (1996)

In the absence of base, the reaction of selenobenzamide with alkyl halides gives the dialkyl diselenides as the major product. While the reaction of selenobenzamide and an alkyl halide is carried out in a 1:2 molar ratio and in the presence of strong base, the dialkyl selenides predominate.

-

Gladysz,J.A. et al.

, p. 1204 - 1208 (1978)

-

Chemoselective synthesis of fuctionalized diselenides

Salama,Bernard

, p. 5711 - 5714 (1995)

The action of LiEt3BH or DIBAL-H on various functionalized selenocyanates was proven to be an efficient means to establish chemoselectively the diselenide bond, under very mild conditions. The mechanism was shown to involve a selenophilic hydri

-

Lewicki,J.W. et al.

, p. 2672 - 2676 (1978)

-

A convenient one-pot synthesis of dibenzyl diselenides under microwave irradiation conditions

Wang, Jin-Xian,Bai, Lin,Li, Wenbo,Hu, Yulai

, p. 325 - 332 (2000)

A simple, rapid and efficient method for the synthesis of dibenzyl diselenides under microwave irradiation is reported. The effect of microwave irradiation power, times and solvent on the reaction is investigated.

A77Se NMR study of elemental selenium reduction using NaBH4

Oliveira, Alfredo Ricardo Marques De,Piovan, Leandro,Simonelli, Fabio,Barison, Anderson,Santos, Maria De Fatima C.,De Mello, Murilo Belini Marcondes

, p. 54 - 59 (2016)

Alkylation or arylation of selenide or diselenide anions is a well-established method to obtain organoselenium compounds. Nevertheless, detecting inorganic selenium anions using77Se NMR is still a challenge. In a previous work, alkylation of Na2Se was found sometimes to yield a mixture of organyl selenides/diselenides in variable amounts. In the literature, this mixture is sometimes attributed to the oxidation of an intermediate alkyl selenol during the extraction. To understand this process, a series of experiments using77Se NMR were performed. It was clear from the77Se NMR experiments that NaHSe-and Se22- formation was very dependent on the NaBH4stoichiometry used. After alkylation, alkyl selenol and dialkyl diselenide were identified, proving they were not formed during the extraction step. As a result, alkyl selenols, dialkyl selenides or dialkyl diselenides with a high purity degree were obtained. To achieve high purity and selectivity of the organoselenium compound, the stoichiometric ratio between Se0/NaBH4has to be carefully measured.

An efficient and practical method for the selective synthesis of sodium diselenide and diorganyl diselenides through selenium reduction

Lim, Yoo Jin,Shin, Na Hye,Kim, Chorong,Kim, Ye Eun,Cho, Hyunsung,Park, Myung-Sook,Lee, Sang Hyup

, (2020)

Studies on an efficient and practical method for the selective synthesis of diorganyl diselenides over diorganyl selenides are presented. Considering the discrepancies between reports on organoselenium compounds, we wanted to establish a tolerable synthetic method for diorganyl diselenides and investigate their characteristics. We optimized reaction conditions for sodium diselenide preparation using selenium, NH2NH2·H2O, and NaOH and, by treating the obtained sodium diselenide with various alkyl or aryl halides, achieved the selective synthesis of diorganyl diselenides in modest to good yields (57–88%) with good reproducibility. We further studied the mechanistic implication, the effects of solvent changes, and the stability of diorganyl diselenides.

Improved method for the synthesis of organic diselenides from organic halides under atmospheric pressure

Chen, Yahong,Tian, Fengshou,Song, Maoping,Lu, Shiwei

, p. 2687 - 2692 (2007)

An improved approach to the synthesis of organic diselenides is reported. The process involves the reaction of organic halides with selenium, carbon monoxide, and water under atmospheric pressure in the presence of an inorganic base, sodium hydroxide, to afford organic diselenides in good yields. Copyright Taylor & Francis Group, LLC.

A synthetic method for diselenides under phase-transfer conditions

Hu, Xubo,Tian, Zhenjiao,Lu, Xueran,Chen, Yuanyin

, p. 553 - 557 (1997)

Diselenides were easily prepared in high yields by the alkylation of sodium diselenide on halides in water under phase-transfer conditions.

First example of selenium transfer reaction of primary selenoamides and selenourea. Novel synthesis of dialkyl diselenides from alkyl halides

Ming-De, Ruan,Hua-Rong, Zhao,Wei-Qiang, Fan,Xun-Jun, Zhou

, p. 19 - 24 (1995)

As selenium transfer reagents, arylselenoamides react with a variety of alkyl halides in ethanol under mild conditions to give dialkyl diselenides in excellent yields.Similarly, alkyl halides treated with selenourea form dialkyl diselenides.The possible mechanism is discussed. Keywords: Selenium; Selenoamides; Diselenides; Selenourea; Alkyl halide

Selenocyanation using a combined reagent of triphenylphosphine and selenocyanogen. A new and simple synthesis of alkyl selenocyanates and symmetrical alkyl diselenides from alcohols

Tamura,Adachi,Kawasaki,Kita

, p. 2251 - 2252 (1979)

A novel reagent Ph3SeCN)2, easily prepared by adding an equimolar amount of tri-phenylphosphine to selenocyanogen solution in methylene chloride and tetrahydrofuran reacts below -60° with primary alcohols to produce directly the corr

Structure of "bis(methoxymagnesium)diselenide": A reagent for the introduction of selenium into organic molecules

Sathyamurthy, Rajashree,Brumaghim, Julia L.,Vanderveer, Donald G.

, p. 109 - 117 (2007)

The reaction of magnesium and selenium in dry methanol has been reported to yield a reagent tentatively identified as bis(methoxymagnesium) diselenide. The dark red-brown solution obtained from this reaction yielded red crystals that crystallized in the monoclinic space group C2/c, a=17.391(4) A, b=15.823(3) A, c=21.626(4) A, β=110.71(3)°, V=5566.5(19) A3, Z=4, R=0.0350, wR2=0.0850 for 4930 reflections. X-ray crystallographic analysis of this reagent showed it to be dodecamethanol-tetramethoxy-di(μ4-hydroxy)tetra(μ3- methoxy)hexamagnesium hexaselenide, Mg6(μ4-OH) 2(μ3-OCH3)4(OCH3) 4(CH3OH)12]Se6·2CH 3OH (1), not the bis(methoxymagnesium) diselenide as previously described. The structure of 1 is composed of six magnesium ions and six bridging oxygen-containing ligands in a face-sharing cubic arrangement.

-

Lewicki,J.W. et al.

, p. 552 (1976)

-

A convenient method for the preparation of dialkylditellurides and dialkyldiselenides

Li,Bao,Lue,Zhou

, p. 799 - 806 (1991)

Dialkylditellurides 3 and dialkyldiselenides 4 were prepared in high yields and in a one-pot procedure by the reduction of elemental tellurium and selenium with phenyl hydrazine in basic medium (NaOH/DMF) followed by treatment with organohalides.

Chu et al.

, p. 4905 (1975)

Highly efficient one-step conversion of selenol esters into symmetrical diselenides in the presence of elemental iodine in methanolic solution

Movassagh, Barahman,Moradi, Mona

, p. 154 - 157 (2010)

A facile, efficient, and convenient procedure has been developed for the direct conversion of selenol esters into the corresponding diselenides in the presence of elemental iodine at room temperature.

The Convenient Syntheses of Organoselenium Reagents

Syper, Ludwig,Mlochowski, Jacek

, p. 439 - 442 (1984)

-

-

Rogers,Campbell

, p. 2039 (1947)

-

Aqueous phase preparation method of dialkyl diselenide ether compound

-

Paragraph 0062-0066, (2021/11/21)

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.

Lead optimization generates selenium-containing miconazole CYP51 inhibitors with improved pharmacological profile for the treatment of fungal infections

Xu, Hang,Yan, Zhong-zuo,Guo, Meng-bi,An, Ran,Wang, Xin,Zhang, Rui,Mou, Yan-hua,Hou, Zhuang,Guo, Chun

, (2021/03/16)

A series of selenium-containing miconazole derivatives were identified as potent antifungal drugs in our previous study. Representative compound A03 (MIC = 0.01 μg/mL against C.alb. 5314) proved efficacious in inhibiting the growth of fungal pathogens. However, further study showed lead compound A03 exhibited potential hemolysis, significant cytotoxic effect and unfavorable metabolic stability and was therefore modified to overcome these drawbacks. In this article, the further optimization of selenium-containing miconazole derivatives resulted in the discovery of similarly potent compound B17 (MIC = 0.02 μg/mL against C.alb. 5314), exhibiting a superior pharmacological profile with decreased rate of metabolism, cytotoxic effect and hemolysis. Furthermore, compound B17 showed fungicidal activity against Candida albicans and significant effects on the treatment of resistant Candida albicans infections. Meanwhile, compound B17 not only could reduce the ergosterol biosynthesis pathway by inhibiting CYP51, but also inhibited biofilm formation. More importantly, compound B17 also shows promising in vivo efficacy after intraperitoneal injection and the PK study of compound B17 was evaluated. In addition, molecular docking studies provide a model for the interaction between the compound B17 and the CYP51 protein. Overall, we believe that these selenium-containing miconazole compounds can be further developed for the potential treatment of fungal infections.

Synthesis of unsymmetrical glycosyl diselenides by the treatment of symmetrical diselenides with glycosyl selenocyanates

Manna, Tapasi,Misra, Anup Kumar,Rana, Abhijit

, (2021/08/03)

A novel reaction condition has been developed for the synthesis of unsymmetrical glycosyl diselenide derivatives in excellent yield by the reaction of glycosyl selenocyanates as selenol surrogates with symmetrical diselenides in the presence of hydrazine monohydrate at room temperature. The reaction metal-free condition is reasonably fast, simple, non-malodorous and suitable for scale-up.

Hydrolysis-Based Small-Molecule Hydrogen Selenide (H2Se) Donors for Intracellular H2Se Delivery

Bolton, Sarah G.,Chouinard, Julie E.,Garcia, Arman C.,Golledge, Stephen L.,Newton, Turner D.,Pluth, Michael D.,Zakharov, Lev N.

, p. 19542 - 19550 (2021/11/23)

Hydrogen selenide (H2Se) is a central metabolite in the biological processing of selenium for incorporation into selenoproteins, which play crucial antioxidant roles in biological systems. Despite being integral to proper physiological function, this reactive selenium species (RSeS) has received limited attention. We recently reported an early example of a H2Se donor (TDN1042) that exhibited slow, sustained release through hydrolysis. Here we expand that technology based on the P-Se motif to develop cyclic-PSe compounds with increased rates of hydrolysis and function through well-defined mechanisms as monitored by 31P and 77Se NMR spectroscopy. In addition, we report a colorimetric method based on the reaction of H2Se with NBD-Cl to generate NBD-SeH (λmax = 551 nm), which can be used to detect free H2Se. Furthermore, we use TOF-SIMS (time of flight secondary ion mass spectroscopy) to demonstrate that these H2Se donors are cell permeable and use this technique for spatial mapping of the intracellular Se content after H2Se delivery. Moreover, these H2Se donors reduce endogenous intracellular reactive oxygen species (ROS) levels. Taken together, this work expands the toolbox of H2Se donor technology and sets the stage for future work focused on the biological activity and beneficial applications of H2Se and related bioinorganic RSeS.

Synthesis of Dibenzylic Diselenides from Elemental Selenium and Benzylic Quaternary Ammonium Salts

Chen, Feng,Li, Fuhai,Zeng, Qingle

, p. 5605 - 5608 (2021/11/11)

Abstract: Substituted dibenzyl diselenides are synthesized in good yields (74–91 %) by SN2 nucleophilic substitution of benzylic trimethylammonium salts and diselenide dianion (Se2?), in situ generated from elemental selenium, under

Process route upstream and downstream products

Process route

dibenzyl selenoxide
25862-08-2

dibenzyl selenoxide

dibenzyl selenide
1842-38-2

dibenzyl selenide

dibenzyl diselenide
1482-82-2

dibenzyl diselenide

benzaldehyde
100-52-7

benzaldehyde

Conditions
Conditions Yield
In benzene; at 20 ℃; for 2h; Irradiation;
benzyl bromide
100-39-0

benzyl bromide

diethylamine
109-89-7

diethylamine

dibenzyl diselenide
1482-82-2

dibenzyl diselenide

N,N-diethylselenobenzamide
72864-65-4

N,N-diethylselenobenzamide

benzaldehyde
100-52-7

benzaldehyde

Conditions
Conditions Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; selenium; sodium hydride; for 3h; Ambient temperature; Irradiation;
1%
25%
14%
benzylidene dichloride
98-87-3

benzylidene dichloride

diethylamine
109-89-7

diethylamine

dibenzyl diselenide
1482-82-2

dibenzyl diselenide

N,N-diethylselenobenzamide
72864-65-4

N,N-diethylselenobenzamide

benzaldehyde
100-52-7

benzaldehyde

Conditions
Conditions Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; selenium; sodium hydride; at 120 ℃; for 3h; Product distribution; Mechanism; other dihalomethane derivatives; other amines; var. temp. and reaction times; also with sonication;
41%
15%
dibenzylselenium dichloride

dibenzylselenium dichloride

dibenzyl diselenide
1482-82-2

dibenzyl diselenide

benzaldehyde
100-52-7

benzaldehyde

Conditions
Conditions Yield
methanol
67-56-1

methanol

dibenzyl selenide
1842-38-2

dibenzyl selenide

benzyl methyl ether
538-86-3

benzyl methyl ether

dibenzyl diselenide
1482-82-2

dibenzyl diselenide

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

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

Conditions
Conditions Yield
With naphthalene-1,4-dicarbonitrile; Quantum yield; Mechanism; Product distribution; Irradiation; energy data, ΔGET, electron transfer equilibrium constant;
73%
5%
18%
With naphthalene-1,4-dicarbonitrile; for 6h; Ambient temperature; Irradiation;
18 % Chromat.
73 % Chromat.
dibenzyl selenide
1842-38-2

dibenzyl selenide

benzyl methyl ether
538-86-3

benzyl methyl ether

dibenzyl diselenide
1482-82-2

dibenzyl diselenide

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

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

Conditions
Conditions Yield
With naphthalene-1,4-dicarbonitrile; In methanol; for 6h; Ambient temperature; Irradiation;
73 % Chromat.
18 % Chromat.
methanol
67-56-1

methanol

dibenzyl selenide
1842-38-2

dibenzyl selenide

benzyl methyl ether
538-86-3

benzyl methyl ether

dibenzyl diselenide
1482-82-2

dibenzyl diselenide

Conditions
Conditions Yield
With naphthalene-1,4-dicarbonitrile; Quantum yield; Irradiation;
methanol
67-56-1

methanol

N-benzyl-N-p-toluenesulfonylhydrazine
18440-49-8

N-benzyl-N-p-toluenesulfonylhydrazine

benzyl methyl ether
538-86-3

benzyl methyl ether

dibenzyl diselenide
1482-82-2

dibenzyl diselenide

benzyl 4-methylbenzenesulfinate
13146-13-9

benzyl 4-methylbenzenesulfinate

p-tolyl benzeneselenosulfonate
68819-94-3

p-tolyl benzeneselenosulfonate

Conditions
Conditions Yield
for 0.166667h; Mechanism; Ambient temperature;
benzyl bromide
100-39-0

benzyl bromide

CH<sub>3</sub>SSe<sup>(1-)</sup>*Na<sup>(1+)</sup>

CH3SSe(1-)*Na(1+)

Dimethyldisulphide
624-92-0

Dimethyldisulphide

dibenzyl diselenide
1482-82-2

dibenzyl diselenide

CH<sub>3</sub>SSeCH<sub>2</sub>C<sub>6</sub>H<sub>5</sub>

CH3SSeCH2C6H5

Conditions
Conditions Yield
In N,N-dimethyl acetamide; at 20 ℃; Product distribution;
29 % Spectr.
14 % Spectr.
57 % Spectr.
diethyl ether
60-29-7,927820-24-4

diethyl ether

water
7732-18-5

water

benzyl chloride
100-44-7

benzyl chloride

dibenzyl disulphide
150-60-7

dibenzyl disulphide

dibenzyl diselenide
1482-82-2

dibenzyl diselenide

Conditions
Conditions Yield

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