(chloroselanyl)benzene

• ChemBase ID: 146519
• Molecular Formular: C6H5ClSe
• Molecular Mass: 191.5169
• Monoisotopic Mass: 191.92449884
• SMILES: c1ccc(cc1)[Se]Cl
• Canonical SMILES: Cl[Se]c1ccccc1
• InChI: InChI=1S/C6H5ClSe/c7-8-6-4-2-1-3-5-6/h1-5H
• InChIKey: WJCXADMLESSGRI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (chloroselanyl)benzene
• IUPAC Traditional name: (chloroselanyl)benzene
• Synonyms: Phenylselenenyl chloride; Benzeneselenenyl chloride; Benzeneselenyl chloride; Phenylselenyl chloride; 苯基硒氯; 苯硒酰氯; 苯基氯化硒

Database IDs

• CAS Number: 5707-04-0
• EC Number: 227-196-2
• MDL Number: MFCD00000478
• Beilstein Number: 1237091
• PubChem SID: 24851046; 162240714; 24887412
• PubChem CID: 21928

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.384
• LogD (pH = 7.4): 2.384
• Log P: 2.384
• Molar Refractivity: 44.7255 cm^3
• Polarizability: 12.243166 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 59-62 °C; 59-62 °C(lit.); 60-65°C
• Boiling Point: 120 °C/20 mmHg(lit.); 120°C/20mm

Safety Information

• Storage Warning: Air & Moisture Sensitive
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: 2928; UN2928
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; II
• Risk Statements: 23/25-33-34-50/53; 23/25-33-50/53
• Safety Statements: 20/21-28-45-60-61
• TSCA Listed: 否
• GHS Pictograms: GHS05; GHS06; GHS08; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H290-H301 + H331-H373-H410; H301-H331-H373-H400-H410
• GHS Precautionary statements: P260-P261-P301+P310-P321-P405-P501A; P261-P273-P301 + P310-P311-P501
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2928 6.1/PG 2

Product Information

• Purity: ≥97.0% (AT); 98%
• Grade: purum
• Linear Formula: C6H5SeCl

DETAILS

Sigma Aldrich - 183342

Packaging
1, 10, 50 g in glass bottle
Application
Synthon for 2-amino alcohols.1 Versatile reagent in organic synthesis.2,3,4

Sigma Aldrich - 79138

Other Notes
A phenylselenylating agent, review1

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 ?-diketones, see: Org. Synth. Coll., 6, 23 (1988):
  
• ?-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 ɑ?-unsaturated carbonyl compounds and nitriles byselenoxide elimination, see: Org. React., 44, 1 (1993).
• Reacts with alkenylboronic acids in ionic liquids to give (Z) and (E) vinyl selenides: Tetrahedron Lett., 43, 373 (2002).
• 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):