2-Chloro-1,3,2-dioxaphospholane 2-oxide

Base Information

• Chemical Name: 2-Chloro-1,3,2-dioxaphospholane 2-oxide
• CAS No.: 6609-64-9
• Molecular Formula: C2H4ClO3P
• Molecular Weight: 142.479
• Hs Code.: 29209090
• European Community (EC) Number: 229-560-6
• UNII: 7EBS5ZK92N
• DSSTox Substance ID: DTXSID70216292
• Nikkaji Number: J185.646D,J641.418D
• Wikidata: Q72449691
• Mol file: 6609-64-9.mol

Synonyms:6609-64-9;2-Chloro-1,3,2-dioxaphospholane-2-oxide;2-Chloro-1,3,2-dioxaphospholane 2-oxide;2-Chloro-2-oxo-1,3,2-dioxaphospholane;Ethylene Chlorophosphate;2-chloro-1,3,2lambda5-dioxaphospholane 2-oxide;C2H4ClO3P;7EBS5ZK92N;EINECS 229-560-6;1,3,2-Dioxaphospholane, 2-chloro-, 2-oxide;MFCD00043138;Ethylene cycl-chlorophosphate;Ethyl enechlorophosphate;UNII-7EBS5ZK92N;SCHEMBL169101;C2-H4-Cl-O3-P;SBMUNILHNJLMBF-UHFFFAOYSA-;DTXSID70216292;BBL100363;STL554157;AKOS015850823;2-chloro-1,3,2-dioxaphospholan-2-oxide;AS-14467;FT-0611683;1,3,2-Dioxaphospholane,2-chloro-, 2-oxide;2-chloro-1,3,2lambda5-dioxaphospholan-2-one;A23562;EN300-266546;2-Chloro-1,3,2-dioxaphospholane-2-oxide, tech.;Q-200255;2-chloro-1,3-dioxa-2$l^{5}-phosphacyclopentane 2-oxide;Ethylene cycl-chlorophosphate (2-chloro-2-oxo-1,3,2-dioxaphospholane)

Chemical Property of 2-Chloro-1,3,2-dioxaphospholane 2-oxide

Chemical Property:

• Appearance/Colour: clear colourless liquid
• Vapor Pressure: 49.3mmHg at 25°C
• Melting Point: 12-14 °C
• Refractive Index: n20/D 1.45(lit.)
• Boiling Point: 96.7 °C at 760 mmHg
• Flash Point: >230 °F
• PSA: 45.34000
• Density: 1.52 g/cm³
• LogP: 1.38010
• Storage Temp.: −20°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: Miscible with water and chloroform.
• XLogP3: 0
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 141.9586587
• Heavy Atom Count: 7
• Complexity: 104

Purity/Quality:

99% ^*data from raw suppliers

2-Chloro-1,3,2-dioxaphospholane 2-oxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 14-34
• Safety Statements: 26-36/37/39-45-8-25-27

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COP(=O)(O1)Cl
• Uses: 2-Chloro-1,3,2-dioxaphospholane-2-oxide is used in the synthesis of α-naphthylphosphorylcholine as a method to detect phospholipase C activity. Ethylene chlorophosphate is used in the syntheses of 2-methacryloyoxyethylphophocholine, phosphatidylcholines, 2',3'-O-16-hentriacontanyliden-adenosine-5'-phosphocholine and hexadecylphosphocholine. It is also involved the synthesis of alpha-naphthylphosphorylcholine, which is used to detect phospholipase C activity. It is an important reactant for the synthesis of a zwitterionic silane, UV-polymerizable lipids utilizing Chabrier reaction and block copolymers of poly(aliphatic ester) clickable polyphosphoester. 2-Chloro-1,3,2-dioxaphospholane 2-oxide may be used in the synthesis of: 2-methacryloyloxyethylphosphorylcholinemiltefosine (hexadecylphosphocholine, MT) analogsphosphoric acid 2-trimethylamino-ethyl ester undec-10-enyl esteruridine nucleolipid, (2′,3′-O-16-hentriacontanyliden-uridine-5′-phosphocholine, PUPC)adenosine nucleoamphiphile, (2′,3′-O-16-hentriacontanyliden-adenosine-5′-phosphocholine, PAPC)structurally related phospholipids which are either conformationally restricted or flexiblephosphatidylcholines

Technology Process of 2-Chloro-1,3,2-dioxaphospholane 2-oxide

There total 6 articles about 2-Chloro-1,3,2-dioxaphospholane 2-oxide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

ethylene glycol (107-21-1) → 2-Chloro-2-oxo-1,3,2-dioxaphospholane (6609-64-9)

Guidance literature:

With trichlorophosphate; In dichloromethane; at 0 ℃; for 14h;

Reference yield: 86.3%

2-chloro-1,3,2-dioxaphospholan (822-39-9) → 2-Chloro-2-oxo-1,3,2-dioxaphospholane (6609-64-9)

Guidance literature:

With oxygen; In benzene; at 50 ℃; for 24h; Inert atmosphere;

Reference yield: 85.0%

2-chloro-1,3,2-dioxaphospholan (822-39-9) → poly(D,L-lactide-co-ethylene methyl phosphate) + 2-Chloro-2-oxo-1,3,2-dioxaphospholane (6609-64-9)

Guidance literature:

upstream raw materials:

2-chloro-1,3,2-dioxaphospholan

ethylene glycol

4,8,14,18,23,26,28,31,32-nonamethoxy-35-hydroxypillar[5]arene

2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane

Downstream raw materials:

N-p-Tolyl-aethylenphosphoroamidat

(1-Methyl-2-phenyl-ethyl)-(2-oxo-2λ⁵-[1,3,2]dioxaphospholan-2-yl)-amine

2-(2-Methoxy-phenoxy)-[1,3,2]dioxaphospholane 2-oxide

N-Phenyl-aethylen-phosphoroamidat

Refernces

Regiospecific Opening of Glycidyl Derivatives Mediated by Boron Trifluoride. Asymmetric Synthesis of Ether-Linked Phospholipids

10.1021/jo00280a034

The research focuses on the asymmetric synthesis of unnatural, cytotoxic ether-linked phospholipids, which are biologically active molecules with potential antitumor activity. The key step in this synthesis involves the highly regio- and stereospecific nucleophilic opening of glycidyl derivatives using boron trifluoride etherate as a catalyst, yielding enantiomeric excess of over 94%. The study successfully developed a short and efficient method to produce enantiomerically pure 1-O-alkyl-2-O-methyl-sn-glycero-3-phosphocholine (5a) and 3-O-alkyl-2-O-methyl-1-sn-glycero-phosphocholine (5b) from optically active glycidyl derivatives, which can be used to study the mechanism of cytotoxic activity and tumor specificity of these anti-neoplastic agents. The chemicals used in the process include p-toluenesulfonate and tert-butyldiphenylsilyl ether derivatives of (R)- and (S)-glycidol, 1-hexadecanol, and various reagents for the subsequent steps of the synthesis, such as methyl triflate, potassium superoxide, and 2-chloro-2-oxo-1,3,2-dioxaphospholane.