Bis(2-chloroethyl)phosphoramidic dichloride
Overview
Description
Bis(2-chloroethyl)phosphoramidic dichloride is an organic phosphorus compound with the molecular formula C4H8Cl4NOP. It is a colorless to pale yellow liquid with a pungent odor and is known for its strong electrophilic properties. This compound is primarily used as a phosphorylating agent and catalyst in various chemical reactions .
Scientific Research Applications
Bis(2-chloroethyl)phosphoramidic dichloride has a wide range of applications in scientific research, including:
Chemistry: It is used as a phosphorylating agent in the synthesis of organophosphorus compounds.
Biology: It is employed in the modification of biomolecules, such as proteins and nucleic acids, to study their structure and function.
Medicine: It is investigated for its potential use in drug development, particularly in the synthesis of phosphorylated drugs.
Safety and Hazards
Bis(2-chloroethyl)phosphoramidic dichloride is classified as acutely toxic if swallowed, in contact with skin, or if inhaled . It can cause severe skin burns and eye damage, and may cause an allergic skin reaction . It is also suspected of causing cancer . Safety measures include avoiding dust formation, avoiding breathing mist, gas or vapours, avoiding contact with skin and eyes, using personal protective equipment, wearing chemical impermeable gloves, ensuring adequate ventilation, and removing all sources of ignition .
Mechanism of Action
Mode of Action
It is hypothesized that the compound may interact with its targets, leading to changes in cellular processes . More detailed studies are required to elucidate the precise mechanisms involved.
Biochemical Pathways
It is likely that the compound influences multiple pathways, leading to downstream effects that contribute to its overall action .
Pharmacokinetics
These properties play a crucial role in determining the bioavailability of the compound .
Result of Action
It is anticipated that the compound induces changes at the molecular and cellular levels, which contribute to its overall effects .
Action Environment
Environmental factors can significantly influence the action, efficacy, and stability of Bis(2-chloroethyl)phosphoramidic dichloride. Factors such as temperature, pH, and the presence of other molecules can affect the compound’s stability and activity .
Preparation Methods
Synthetic Routes and Reaction Conditions
Bis(2-chloroethyl)phosphoramidic dichloride can be synthesized through the chlorination of diethanolamine using thionyl chloride, resulting in the formation of N,N-bis(2-chloroethyl)amine hydrochloride. This intermediate is then condensed with phosphorus oxychloride to produce the final compound .
Industrial Production Methods
The industrial production of this compound follows a similar synthetic route, with careful control of reaction conditions to ensure high yield and purity. The process involves the use of large-scale reactors and precise temperature and pressure control to optimize the reaction .
Chemical Reactions Analysis
Types of Reactions
Bis(2-chloroethyl)phosphoramidic dichloride undergoes various types of chemical reactions, including:
Substitution Reactions: It reacts with nucleophiles such as alcohols, amines, and carboxylic acids to form corresponding phosphorylated products.
Hydrolysis: In the presence of water, it hydrolyzes to form bis(2-chloroethyl)phosphoric acid and hydrochloric acid.
Common Reagents and Conditions
Common reagents used in reactions with this compound include alcohols, amines, and carboxylic acids. The reactions typically occur under mild conditions, often at room temperature or slightly elevated temperatures, and may require the presence of a base to neutralize the generated hydrochloric acid .
Major Products Formed
The major products formed from reactions with this compound include phosphorylated alcohols, amines, and carboxylic acids. These products are valuable intermediates in the synthesis of various organic compounds .
Comparison with Similar Compounds
Similar Compounds
- Bis(2-chloroethyl)phosphoric acid
- Bis(2-chloroethyl)phosphoramide
- Bis(2-chloroethyl)phosphorothioate
Uniqueness
Bis(2-chloroethyl)phosphoramidic dichloride is unique due to its strong electrophilic properties and its ability to act as a versatile phosphorylating agent. Compared to similar compounds, it offers higher reactivity and selectivity in phosphorylation reactions, making it a valuable tool in both research and industrial applications .
Properties
IUPAC Name |
2-chloro-N-(2-chloroethyl)-N-dichlorophosphorylethanamine |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C4H8Cl4NOP/c5-1-3-9(4-2-6)11(7,8)10/h1-4H2 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
IQPMYTNILJQKBS-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
C(CCl)N(CCCl)P(=O)(Cl)Cl |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C4H8Cl4NOP |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID40155366 |
Source
|
| Record name | Phosphoramidic dichloride, bis(2-chloroethyl)- | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID40155366 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
258.9 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
CAS No. |
127-88-8 |
Source
|
| Record name | N,N-Bis(2-chloroethyl)phosphoramidic dichloride | |
| Source | CAS Common Chemistry | |
| URL | https://commonchemistry.cas.org/detail?cas_rn=127-88-8 | |
| Description | CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society. | |
| Explanation | The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated. | |
| Record name | Phosphoramidic dichloride, bis(2-chloroethyl)- | |
| Source | ChemIDplus | |
| URL | https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000127888 | |
| Description | ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system. | |
| Record name | 127-88-8 | |
| Source | DTP/NCI | |
| URL | https://dtp.cancer.gov/dtpstandard/servlet/dwindex?searchtype=NSC&outputformat=html&searchlist=64119 | |
| Description | The NCI Development Therapeutics Program (DTP) provides services and resources to the academic and private-sector research communities worldwide to facilitate the discovery and development of new cancer therapeutic agents. | |
| Explanation | Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source. | |
| Record name | Phosphoramidic dichloride, bis(2-chloroethyl)- | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID40155366 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
| Record name | Bis(2-chloroethyl)phosphoramidic Dichloride | |
| Source | European Chemicals Agency (ECHA) | |
| URL | https://echa.europa.eu/information-on-chemicals | |
| Description | The European Chemicals Agency (ECHA) is an agency of the European Union which is the driving force among regulatory authorities in implementing the EU's groundbreaking chemicals legislation for the benefit of human health and the environment as well as for innovation and competitiveness. | |
| Explanation | Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. | |
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Retrosynthesis Analysis
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Strategy Settings
| Precursor scoring | Relevance Heuristic |
|---|---|
| Min. plausibility | 0.01 |
| Model | Template_relevance |
| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
Feasible Synthetic Routes
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