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Phenyl phosphorodichloridate, 97% - CAS 770-12-7 - Formula C6H5Cl2O2P


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A10479
Phenyl phosphorodichloridate, 97%

CAS: 770-12-7 MDL: MFCD00002067  EINECS: 212-220-6
UN#:UN2922Hazard Class:8Packing Group:II
Alternate Name: Phenyl dichlorophosphate

 

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Chemical Properties

Formula: C6H5Cl2O2P  Flash point: 112°(233°F)
Formula weight: 210.98  Density: 1.415
Melting point: -1° Refractive Index: 1.5230
Boiling point: 241-243° Sensitivity: Moisture Sensitive

Literature References

Reagent for the preparation of phosphate diesters. The phenyl group is removable by hydrogenolysis: J. Am. Chem. Soc., 75, 4510 (1953).

Coupling reagent, e.g. in pyridine for the preparation of derivatives of sulfinic acids with alcohols, amines, thiols etc.: Synthesis, 937 (1980). Similarly, carboxylic acids in pyridine can be coupled with thiols to give thiocarboxylic acid S-esters: Can. J. Chem., 58, 2645 (1980), and with sodium azide in the presence of a phase-transfer catalyst to give acyl azides: Synth. Commun., 13, 289 (1983).

Reacts with the Li enolates of ß-diketones, in the presence of LiCl, to give ß-chloro-ɑß-enones: Can. J. Chem., 64, 520 (1986).

In combination with NaI, cleaves dialkyl ethers to iodides in high yield: Synth. Commun., 18, 119 (1988), and 1,3-dithianes and other dithioacetals to carbonyl groups: Tetrahedron Lett., 29, 5471 (1988).

In combination with Dimethyl­ sulfoxide, A13280, effects selective oxidation of alcohols to aldehydes or ketones with less ɑ-chlorination than the more usual Swern (Oxalyl­ chloride, A18012) system: J. Org. Chem., 52, 5621 (1987). Similarly, benzylamines have been converted to benzaldehydes: Synth. Commun., 19, 3407 (1989).

For a brief feature on uses of the reagent in synthesis, see: Synlett, 1651 (2004).


Applications

Reagent for preparation of phosphate diesters

Other References

Beilstein: 511863
UN#: UN2922
Harmonized Tariff Code:   2920.90

GHS Hazard and Precautionary Statements

Hazard Statements : H301-H310-H314-H318

Toxic if swallowed. Fatal in contact with skin. Causes severe skin burns and eye damage. Causes serious eye damage.

Precautionary Statements : P260-P301+P310-P303+P361+P353-P305+P351+P338-P361-P405-P501A

Do not breathe dust/fume/gas/mist/vapours/spray. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Remove/Take off immediately all contaminated clothing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

CorrosiveToxic

Risk & Safety

Risk Phrases: 22-27-34
Harmful if swallowed. Very toxic in contact with skin. Causes burns.
Safety Phrases: 26-28-36/37/39-45
In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label where possible).
Very Toxic
TSCA: Yes
RTECS: TD4393000