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Thermo Scientific Chemicals
Phenylselenenyl bromide, 98%
CAS: 34837-55-3 | C6H5BrSe | 235.981 g/mol
化学物質識別子
CAS34837-55-3
IUPAC Name(phenylselanyl)bromane
Molecular FormulaC6H5BrSe
InChI KeyLCEFEIBEOBPPSJ-UHFFFAOYSA-N
SMILESBr[Se]C1=CC=CC=C1
さらに表示
仕様
スペックシート
スペックシートIdentification (FTIR)Conforms
Appearance (Color)Dark purple
Assay (Titration ex Bromide)≥97.5 to ≤102.5%
FormCrystals or powder or crystalline powder or fused solid
Employed in the synthesis of enones by selenenylation of α-cyano ketones with lithium naphthalenide. Phenylselenyl bromide was used in the preparation of exo-2-methyl-7-phenylselenyl-octahydro-8-oxa-2,7b-diaza-dicyclopenta[a,e]pentalene-1,3-dione and endo-2-methyl-7-phenylselanyl-octahydro-8-oxa-2,7b-diaza-dicyclopenta[a,e]pentalene-1,3-dione.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
Employed in the synthesis of enones by selenenylation of α-cyano ketones with lithium naphthalenide. Phenylselenyl bromide was used in the preparation of exo-2-methyl-7-phenylselenyl-octahydro-8-oxa-2,7b-diaza-dicyclopenta[a,e]pentalene-1,3-dione and endo-2-methyl-7-phenylselanyl-octahydro-8-oxa-2,7b-diaza-dicyclopenta[a,e]pentalene-1,3-dione.
Solubility
Soluble in toluene, very faint turbidity.
Notes
Moisture Sensitive. Store away from air and water/moisture. Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Store away from oxidizing agent.
Employed in the synthesis of enones by selenenylation of α-cyano ketones with lithium naphthalenide. Phenylselenyl bromide was used in the preparation of exo-2-methyl-7-phenylselenyl-octahydro-8-oxa-2,7b-diaza-dicyclopenta[a,e]pentalene-1,3-dione and endo-2-methyl-7-phenylselanyl-octahydro-8-oxa-2,7b-diaza-dicyclopenta[a,e]pentalene-1,3-dione.
Solubility
Soluble in toluene, very faint turbidity.
Notes
Moisture Sensitive. Store away from air and water/moisture. Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Store away from oxidizing agent.
RUO – Research Use Only
General References:
- Ali Dondas H, et al. X= Y-ZH Systems as potential 1, 3-dipoles. Part 52: Fused-ring forming electrophile induced oxime→nitrone→ cycloaddition cascades. Tetrahedron Lett.2001,57(32), 7035-7045.
- Derek H.R. Barton; George Bashiardes; Jean-Louis Fourrey . Studies on the oxidation of hydrazones with iodine and with phenylselenenyl bromide in the presence of strong organic bases; an improved procedure for the synthesis of vinyl iodides and phenyl-vinyl selenides. Tetrahedron,1988, 44(1), 147-162.
- Reagent for the introduction of the phenylseleno group. Compare following entry (phenylselenenyl chloride) and Diphenyl diselenide, A13919.
- Addition to alkenes gives the kinetic product at low temperature in THF but the thermodynamic product at room temperature in acetonitrile: J. Org. Chem., 42, 2950 (1977):