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5707-04-0 - Phenylselenenyl chloride, 98% - Benzeneselenenyl chloride - A12751 - Alfa Aesar

A12751 Phenylselenenyl chloride, 98%

CAS Number
5707-04-0
Synonyms
Benzeneselenenyl chloride

Size Price ($) Quantity Availability
5g 65.10
25g 255.44
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Phenylselenenyl chloride, 98%

MDL
MFCD00000478
EINECS
227-196-2

Chemical Properties

Formula
C6H5ClSe
Formula Weight
191.52
Melting point
60-65°
Boiling Point
120°/20mm
Sensitivity
Air & Moisture Sensitive
Solubility
Soluble in methanol.

Applications

Phenylselenenyl chloride is used in the preparation of (cyclobut-1-enylselanyl)benzene. It is an important versatile reagent used in organic synthesis. Further, it serves as a useful synthon for 2-amino alcohols.

Notes

Moisture sensitive. Incompatible with strong bases, strong oxidizing agents and strong alkalis.

Literature References

ɑ-Phenylselenoketones can be prepared, e.g. by reaction of Li enolates with phenylselenenyl halides, and conversion to the corresponding unsaturated ketones by selenoxide elimination: J. Am. Chem. Soc., 97, 5434 (1975). Oxidizing agents include H2O2, mCPBA or periodate. For application to ß-diketones, see: Org. Synth. Coll., 6, 23 (1988):

ß-Keto lactones undergo a similar sequence to give unsaturated lactones: J. Org. Chem., 46, 2920 (1981). -Lactones can be converted to dihydrofurans and thence to furans: J. Org. Chem., 40, 542 (1975). Similarly, cyclohexenones can be aromatized to phenols by selenenylation of the enolate and oxidation with mCPBA: Tetrahedron Lett., 23, 51 (1982). For a comprehensive review of the preparation of ɑß-unsaturated carbonyl compounds and nitriles byselenoxide elimination, see: Org. React., 44, 1 (1993).

Adds to alkenes to give trans-chloroselenylated dervatives via a selenium bridged cation: J. Org. Chem., 39, 428 (1974); Tetrahedron Lett., 4977 (1978). Also widely applied in cyclization of various molecules containing olefinic double bonds, e.g. unsaturated alcohols undergo seleno-etherification: J. Am. Chem. Soc., 102, 3784 (1980); Tetrahedron Lett., 31, 5917 (1990).

δ-Unsaturated ketones undergo cyclofunctionalization, providing access to vic-functionalized cyclopropanes and oxygenated heterocycles: Synlett, 965 (1994):

Reacts with alkenylboronic acids in ionic liquids to give (Z) and (E) vinyl selenides: Tetrahedron Lett., 43, 373 (2002).

Tancock, J.; Wirth, T. Selenium-Mediated Synthesis of Tetrasubstituted Naphthalenes through Rearrangement. Molecules 2015, 20 (6), 10866-10872.

U. A. Kshirsagar. Recent developments in the chemistry of quinazolinone alkaloids. Org. Biomol. Chem. 2015, 13 (36), 9336-9352.

GHS Hazard and Precautionary Statements

Hazard Statements: H301-H331-H373-H400-H410

Toxic if swallowed. Toxic if inhaled. May cause damage to organs through prolonged or repeated exposure. Very toxic to aquatic life. Very toxic to aquatic life with long lasting effects.

Precautionary Statements: P260-P261-P273-P301+P310-P304+P340-P311-P321-P405-P403+P233-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Avoid breathing dust/fume/gas/mist/vapours/spray. Avoid release to the environment. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Call a POISON CENTER or doctor/physician. Specific treatment (see label). Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
1237091
Hazard Class
6.1
Packing Group
II
Harmonized Tariff Code
2931.90
TSCA
No

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