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New Chemicals Available for Industrial Research SUBJECT—PHEMYLPHOSPHORUS
ACID
CHLORIDES
SUMMARY OF PROPERTIES
Name
PHENYLPHOSPHORUS DICHLORIDE
PHENYLPHOSPHORUS OXYDICHLORIDE
Cl
Formula
PHENYLPHOSPHORUS THIODICHLORIDE
^ CI CeH5P = 0 "CI
CeH5P "CI
^Cl C6H5P = S "CI
Physical State Color
Liquid Colorless
Liquid Colorless
Liquid Colorless
Molecular Weight
179
195
211
Specific Gravity
1 . 3 1 9 ( 2 0 °C)
1 . 3 7 5 ( 2 0 °C)
1 . 3 7 6 (13°C)
1 . 5 5 6 (ND)
1.622
Refractive .Index
(ND)
Acidity
Acid
Acid
Acid
Hydrolysis
Fast
Fast
Very slow
Boiling Point
224.6°C (atm. )
258°C (atmTj
205°C (130 mm)
Melting Point
-55 °C
3.0 °C
Viscous at -70 °C
Solubility
Soluble in common inert org. solvents.
Soluble in common inert org. solvents.
Soluble in common inert org. solvents.
Solubility in Water
Reacts
Reacts
Reacts
Chemical Properties
Fumes in air. Hydrolyzes in water to form phenylphosphinic acid. 2 chlorine atoms reactive with alcohols, p h e nols, amines, and aidehydes. Adds oxygen, sulfur, and halogens. Intermediate in preparation of phosphinic acid derivatives and anti-oxidants. O i l additive.
Hydrolyzes in water to form phenylphos— phonic acid. Two r e active chlorine atoms capable of reacting with alcohols, p h e nols, and amines to form the corresponding esters and amides, Intermediate in preparation of plasticizers and oil-additives,
Decomposes slowly in water. Two reactive chlorine atoms capable of reacting with alcohols, phenols, and amines to form the corresponding neutral esters and amides. Intermediate for org. synthesis. Extreme pressure lubricant additive. Plasticizer intermediate.
Possible Uses:
C O M M E N T S — P h e n y l p h o s p h o r u s dichloride is a highly reactive acid chloride from which many derivatives containing trivalent phosphorus can be made. It should be handled with caution. Phenylphosphorus oxydichloride is a reactive acid chloride which is used as an intermediate in the preparation
NOTE—Because of present limitations in the supply of certain critical materials, samples of the above and other Victor Research Chemicals announced from time to time are not always available. Those that are will be sent promptly upon request. Others, for which research has established important uses in essential war production, are already available in commercial quantities.
of the phenylphosphonates. It reacts smoothly with a large number of compounds containing an active hydrogen. Phenylphosphorus thiodichloride is a less reactive acid chloride which will react directly with phenols to give phenylthiophosphonates.
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