9-CHLORO-9-PHENYLXANTHENE Property

Melting point:

102-106 °C (lit.)

Boiling point:

387.1±42.0 °C(Predicted)

Density 

1.30±0.1 g/cm3(Predicted)

solubility 

chloroform: soluble25mg/mL, clear, yellow to orange

BRN 

237712

Safety

Safety Statements 

22-24/25

WGK Germany 

3

F 

8-10-21

HS Code 

2932990090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

9-CHLORO-9-PHENYLXANTHENE Chemical Properties,Usage,Production

Uses

9-Chloro-9-phenylxanthene was used in the preparation of (1S,5S,6R,8S)-6-[(allyloxycarbonyl)oxy]-5-(trifluoroacetamido)-8-[9′-(9′-phenylxanthenyl)oxy]-2-oxabicyclo(3.2.1)octane.

Purification Methods

A possible impurity is 9-hydroxy-9-phenylxanthene. If the material contains a lot of the hydroxy product, then boil 10g of it in CHCl3 (50mL) with redistilled acetyl chloride (1mL) until liberation of HCl is complete. Evaporation leaves the chlorophenylxanthene as the hydrochloride which on heating with *benzene loses HCl; and on adding pet ether prisms of chlorophenylxanthene separate and contain 0.5mol of *benzene. The *benzene-free compound is obtained on drying, and it melts to a colourless liquid. [Gomberg & Cone Justus Liebigs Ann Chem 370 142 1909.] The 9-phenylxanthyl group is called “pixyl” and is a good protecting group [Chattopadhyaya & Reese J Chem Soc, Chem Commun 639 1978, Beilstein 17 III/IV 1704.]