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A12751 Phenylselenenyl chloride, 98%

CAS Number
5707-04-0
Synonyms
Benzeneselenenyl chloride

Stock No. Size Price ($) Quantity Availability
A12751-06 5g 67.60
A12751-14 25g 262.00
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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
Storage & Sensitivity
Moisture Sensitive. Air Sensitive. Store under Nitrogen. Ambient temperatures.
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

Toxic if swallowed. Toxic if inhaled. May cause damage to organs through prolonged or repeated exposure.

Precautionary Statements: P260-P264b-P270-P271-P301+P310-P304+P340-P311-P314-P330-P501c

Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. 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. Get medical advice/attention if you feel unwell. Rinse mouth. Dispose of contents/ container to an approved waste disposal plant

Other References

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

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