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Ethyl dichlorophosphate

CAS#[1498-51-7]
G-codeGEO-01336
EC number216-099-0
Molecular formulaC2H5Cl2O2P
Molecular weight162.94
Synonyms

Dichlorophosphoric acid O-ethyl ester ; Ethyl phosphorodichloridate ; ethoxyphosphonoyl dichloride ; Dichloroethoxyphosphine oxide

Structure of Ethyl dichlorophosphate
General description

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Regulatory Information

Transport InformationTOXIC LIQUID, CORROSIVE, ORGANIC, N.O.S. UN2927 6.1 (8)/ PG II
GHS pictogram
GHS05_corrosiveGHS06_toxic
Signal WordDanger
Hazard Statements
H301 - H311 - H314 - H330

H301 – Toxic if swallowed
H311 – Toxic in contact with skin
H314 – Causes severe skin burns and eye damage
H330 – Fatal if inhaled

Precautionary Statements
P260 - P280 - P312 - P301+310 - P301+330+331 - P302+350 - P304+340 - P305+351+338 - P312

P260 – Do not breathe dust/fume/gas/mist/vapours/spray:
P280 – Wear protective gloves/protective clothing/eye protection/face protection:
P301+310 – IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician
P301+330+331 – IF SWALLOWED: Rinse mouth. Do NOT induce vomiting
P302+350 – IF ON SKIN: Gently wash with soap and water
P304+340 – IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P305+351+338 – IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
P312 – Call a POISON CENTER or doctor/physician if you feel unwell:

Documents
Safety Data Sheet

Product categorization

Main category

Description

Ethyl dichlorophosphate is a highly reactive electrophile suitable for important nucleophilic …

Show full description
Ethyl dichlorophosphate [1498-51-7] or ethyl phosphorodichloridate is a colorless oily liquid with the boiling point of 58-62 °C/10 mmHg.[1] It is strongly irritating to skin and very toxic by ingestion, inhalation, or by skin absorption due to the inhibition of acetylcholinesterase (IC50 400 nm).[2] It can be easily prepared from phosphoryl chloride by treatment with 1 equivalent of ethanol in the presence of triethylamine.[3]

Application of Ethyl dichlorophosphate:

It is a highly reactive electrophile suitable for important nucleophilic additions, it can be used in preparation of various  nucleoside phosphate and phosphonate prodrugs.[4] It was recently used as a starting material in the synthesis of phosphinanes and azaphosphinanes as potent and selective inhibitors of activated thrombin-activatable fibrinolysis inhibitor (TAFIa) as a promising therapeutic option to treat patients with pulmonary embolism or ischemic stroke by accelerating blood vessel recanalization and improving patient outcome.[5]

Product categorization (Chemical groups):

Main category: _______________________________________________________________________
[1] Z. J. He, Y. M. Wang, C. C. Tang Phosphorus Sulfur Silicon Relat. Elem. 1997, 127 (1), 59. doi:10.1080/10426509708040496 [2] Y. Segall, G. B. Quistad, S. E. Sparks, J. E. Casida Chem. Res. Toxicol. 2003, 16 (3), 350. doi:10.1021/tx020094l [3] S. Jones, D. Selitsianos Tetrahedron Asymmetry, 2005, 16 (18), 3128. doi:10.1016/j.tetasy.2005.08.025 [4] U. Pradere, E. C. Garnier-Amblard, S. J. Coats, F. Amblard, R. F. Schinazi Chem. Rev. 2014, 114, 9154. doi:10.1021/cr5002035 [5] A. P. Schaffner, P. Sansilvestri-Morel, N. Despaux, E. Ruano, T. Persigand, A. Rupin, P. Mennecier, M. O. Vallez, E. Raimbaud, P. Desos, P. Gloanec J. Med. Chem. 2021, 64 (7), 3897. doi:10.1021/acs.jmedchem.0c02072

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