Diethyl chloromethylphosphonate
Diethyl chloromethylphosphonate (CAS: 3167-63-3) is a reactive organophosphorus compound with the linear formula ClCH2PO(OC2H5)2 and a molecular weight of 186.57 g/mol. It serves as a versatile building block in organic synthesis, particularly in C-C bond formation and olefination reactions. Its utility extends to the preparation of various cyclic compounds and phosphorylated intermediates.
- IUPAC
- Chloromethylphosphonic acid diethyl ester,NSC 67753
- Synonyms
- Chloromethylphosphonic acid diethyl esterDiethyl (chloromethyl)phosphonate
Alkylation Reactions
This compound participates in subsequent alkylation steps following nucleophilic substitution, enabling the introduction of phosphonate groups into organic molecules. It is also employed in one-pot alkylation-boration sequences of alpha-haloalkylphosphonates.
Synthesis of Cyclic Derivatives
Diethyl chloromethylphosphonate is instrumental in synthesizing cyclopentane and pyrrolidine derivatives through regioselective insertion reactions. Furthermore, it facilitates the formation of P-containing cyclopropanes via phosphorylation.
Horner-Wadsworth-Emmons Reagents
As a key component in Wadsworth-Emmons reactions, it is utilized for the efficient synthesis of alkenes from carbonyl compounds, playing a vital role in olefination chemistry.
Carbenoid Insertion Reactions
Its reactivity profile allows for ring expansion of zircnacycles through carbenoid insertion, showcasing its application in complex organic transformations.
| Molecular weight | 186.57 |
|---|---|
| Linear formula | ClCH2PO(OC2H5)2 |
| Assay | 97% |
| Boiling point | 109-110 °C/10 mmHg(lit.) |
| Density | 1.2 g/mL at 25 °C(lit.) |
| Refractive index | n20/D 1.437(lit.) |
| Application | Reactant involved in:• Subsequent alkylation after nucleophilic substitution1• One-pot alkylation-boration of α-haloalkylphosphonates2• Synthesis of cyclpentane and pyrrolidine derivatives via regioselective insertion reactions3• Phosphorylation leading to P-containing cyclopropanes4• Wadsworth-Emmons reactions5• Ring expansion of zircnacycles via carbenoid insertion6 |
Hazard statements
- H315Causes skin irritation
- H319Causes serious eye irritation
- H335May cause respiratory irritation
Precautionary statements
- P261Avoid breathing dust, fume, gas or vapours
- P305IF IN EYES
| Protective equipment | Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter |
|---|---|
| Flash point | 86 °C / 186.8 °F |
| Transport (UN / ADR) | NA 1993 / PGIII |
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 26-36 |
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is Diethyl chloromethylphosphonate primarily used for?
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Diethyl chloromethylphosphonate (CAS: 3167-63-3) is primarily used as a reactant in various organic synthesis applications, including alkylation, olefination (Horner-Wadsworth-Emmons reactions), and the synthesis of cyclic compounds.
What are the CAS number and formula for Diethyl chloromethylphosphonate?
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The CAS number for Diethyl chloromethylphosphonate is 3167-63-3, and its linear formula is ClCH2PO(OC2H5)2.
What grade and purity does Tech Serve Solutions supply for Diethyl chloromethylphosphonate?
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Tech Serve Solutions supplies Diethyl chloromethylphosphonate with a minimum assay of 97%. This product is intended for research and chemical synthesis purposes and is not represented as USP, BP, EP, or pharmacopoeia grade.
How should Diethyl chloromethylphosphonate be handled safely?
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Diethyl chloromethylphosphonate is classified with GHS07 signal word 'Warning' and carries hazard statements H315 (Causes skin irritation), H319 (Causes serious eye irritation), and H335 (May cause respiratory irritation). Appropriate personal protective equipment, including eyeshields, gloves, and suitable respiratory protection (e.g., type ABEK respirator filter), should be used. Handle in a well-ventilated area.
How is Diethyl chloromethylphosphonate packed, shipped, and exported?
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Diethyl chloromethylphosphonate is typically packed in compliance with international shipping regulations (ADR/RID/IMDG/IATA) and is available for global export by Tech Serve Solutions.
How can I request a quote or sample of Diethyl chloromethylphosphonate?
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To request a quote or a sample of Diethyl chloromethylphosphonate, please contact our sales team through the website or by phone, providing your specific requirements.
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