Ethylene chlorophosphate 95%Min Colorless to pale yellow liquid RC00089

Manufacturer: Hangzhou Royalchem Co.,LTD.

Website:  www.cnroyalchem.com

Ethylene Chlorophosphate (CAS 6609-64-9)

1. Chemical Identification

CAS Registry Number:  6609-64-9

Systematic Name:   2-Chloro-1,3,2-dioxaphospholane 2-oxide  (IUPAC)

Common Names:

Ethylene Chlorophosphate

2-Chloro-2-oxo-1,3,2-dioxaphospholane

Ethylene Phosphorochloridate

2-Chloro-1,3,2-dioxaphospholan-2-one

Molecular Formula:  C₂H₄ClO₂P

Structure:

A 5-membered cyclic ester (dioxaphospholane ring) formed by ethylene glycol and phosphoryl chloride (POCl₃).

Contains a highly reactive  P-Cl bond  and a  cyclic phosphate ester  structure.

2. Physical and Chemical Properties

Appearance:  Typically a colorless to pale yellow liquid.

Odor:  Sharp, pungent odor (often described as similar to POCI3).

Molecular Weight:  126.48 g/mol

Density:  ~1.5 g/cm³ (estimated, typically denser than water).

Boiling Point:  Approximately  45-50 °C (10 mmHg)  -  Distills under reduced pressure  due to thermal instability/reactions at higher temperatures.

Melting Point:  Not typically reported/used; handled as a liquid.

Solubility:

Highly soluble  in common organic solvents (dichloromethane, chloroform, ether, THF, benzene, acetonitrile).

Reacts violently with water  (hydrolysis).

Reactivity:

Highly Moisture-Sensitive:  Reacts vigorously with water, alcohols, amines, etc., releasing HCl.  Requires strict anhydrous handling.

Corrosive:  Causes severe skin burns and eye damage.

Lachrymator:  Vapors cause eye irritation/tearing.

Reacts with Nucleophiles:  Undergoes nucleophilic substitution at phosphorus (e.g., with amines to form phosphoramidates, alcohols to form phosphate esters).

Thermal Instability:  May decompose upon heating or distillation at atmospheric pressure, potentially releasing POCl₃ and other products.

3. Handling and Storage

Handling:

Mandatory:  Use ONLY in a well-ventilated  fume hood .

Personal Protective Equipment (PPE):  Chemical-resistant gloves (nitrile, neoprene), safety goggles or face shield, lab coat/apron, and appropriate respiratory protection if vapor levels are significant.

Inert Atmosphere:  Handle under an inert gas atmosphere (dry nitrogen or argon) using Schlenk-line or glovebox techniques.

Dry Techniques:  Use anhydrous solvents and ensure all glassware is thoroughly dried.

Avoid Contact:  Prevent contact with skin, eyes, clothing, and moisture.

Storage:

Store in  tightly sealed, air-tight containers  under an  inert atmosphere  (N² or Ar).

Store below room temperature (e.g., 2-8°C / 35-46°F) to minimize decomposition.

Keep away from moisture, heat, sparks, open flames, and incompatible materials (water, strong bases, alcohols, amines, oxidizers).

Packaging:  Typically supplied in glass ampules, sealed bottles, or cylinders under inert gas (common sizes: 1g, 5g, 10g, 25g, 100g, 1kg).

4. Hazards

GHS Hazard Statements:

H290:  May be corrosive to metals.

H302:  Harmful if swallowed.

H314:  Causes severe skin burns and eye damage.

H317:  May cause an allergic skin reaction.

H330:  Fatal if inhaled.

H335:  May cause respiratory irritation.

H410:  Very toxic to aquatic life with long-lasting effects.

Principal Hazards:  Corrosive, Toxic, Moisture-Sensitive, Lachrymator, Environmental Hazard.

5. Applications (Primary Use)

Ethylene Chlorophosphate is primarily used as a  highly reactive synthetic intermediate  in organophosphorus chemistry due to its strained ring and reactive P-Cl bond. Key applications include:

Flame Retardant Precursor:  Synthesis of cyclic phosphate esters used as flame retardants/additives in polymers and textiles (e.g., Trisdichloropropyl phosphate (TDCPP) precursor).

Agrochemical Intermediates:  Building block for cyclic phosphonate/phosphoramidate insecticides, herbicides, or plant growth regulators.

Chemical Intermediate:  Production of cyclic phosphites, phosphonates, phosphoramidates, and other functionalized phosphorus compounds via reactions with nucleophiles (ROH, RNH₂).

Lithium Battery Electrolyte Additives:  Precursor to cyclic phosphate additives (like ethylene ethylphosphate) used to improve stability and performance.

Phosphorylation Reagent:  Useful for introducing the cyclic phosphate moiety in organic synthesis.

6. Stability and Reactivity

Stability:  Thermally unstable at elevated temperatures and atmospheric pressure.  Unstable in air/moisture.

Incompatible Materials:  Water, Steam, Moist Air, Strong Bases, Alcohols, Amines, Oxidizing Agents, Metals.

Hazardous Decomposition Products:  Hydrogen chloride (HCl), Phosphorus oxides (e.g., POCl₃), carbon monoxide (CO), carbon dioxide (CO₂) upon heating or combustion.

7. First Aid Measures

Inhalation:  Move to fresh air. Administer oxygen if breathing is difficult. Seek immediate medical attention.

Skin Contact:  Remove contaminated clothing. Wash skin immediately with copious soap and water for at least 15 minutes. Seek IMMEDIATE medical attention.

Eye Contact:  Rinse cautiously with water for at least 15 minutes, lifting upper and lower eyelids. Seek IMMEDIATE medical attention.

Ingestion:  Do  NOT  induce vomiting. Rinse mouth with water. Seek IMMEDIATE medical attention.  Never give anything by mouth to an unconscious person.

8. Disposal

Dispose of as  hazardous waste  in accordance with all applicable local, regional, national, and international regulations.

Small Quantities:  May be carefully hydrolyzed under controlled, cold conditions with copious amounts of water in a fume hood, followed by neutralization of the acidic solution (HCl/H₃PO₄) before disposal.  This must ONLY be performed by trained personnel with appropriate PPE and precautions.

Key Summary Points

Highly reactive, moisture-sensitive cyclic organophosphorus reagent (P-Cl bond).

Requires strict anhydrous and inert atmosphere handling (fume hood, gloves, goggles).

Corrosive and toxic (severe burns, harmful inhalation/ingestion).

Crucial intermediate for synthesizing flame retardants, agrochemicals, and specialty phosphorus compounds.

Distills under reduced pressure.