4-(Hydroxymethyl)-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane 1-oxide

Base Information

• Chemical Name: 4-(Hydroxymethyl)-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane 1-oxide
• CAS No.: 5301-78-0
• Molecular Formula: C5H9O5P
• Molecular Weight: 180.097
• Hs Code.: 2909499000
• European Community (EC) Number: 610-937-2
• DSSTox Substance ID: DTXSID20201057
• Nikkaji Number: J1.567.766J
• Wikidata: Q72514671
• Mol file: 5301-78-0.mol

Synonyms:5301-78-0;4-(Hydroxymethyl)-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane 1-oxide;Pentaerythritol phosphate alcohol;2,6,7-TRIOXA-1-PHOSPHABICYCLO2.2.2OCTANE-4-METHANOL, 1-OXIDE;2,6,7-Trioxa-1-phosphabicyclo[2.2.2]octane-4-methanol 1-oxide;CN 1137;BRN 1951494;Pentaerythritol, cyclic phosphate (1:1);2,6,7-Trioxa-1-phosphabicyclo[2.2.2]octane-4-methanol, 1-oxide;(1-oxo-2,6,7-trioxa-1lambda5-phosphabicyclo[2.2.2]octan-4-yl)methanol;4-Hydroxymethyl-2,6,7-trioxa-1-phosphabicyclo(2.2.2)octane-1-oxide;Pentaerythritol, cyclic phosphate (1:1) (8CI);2,6,7-Trioxa-1-phosphabicyclo(2.2.2)octane-4-methanol, 1-oxide;C5H9O5P;SCHEMBL5555604;DTXSID20201057;AMY39356;BCP05526;MFCD17976574;AKOS005137996;AKOS037643204;CS-W017234;GC10184;AS-10520;LS-157659;FT-0689985;H1548;A852093;J-513744;1-Oxo-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane-4-methanol;(1-Oxo-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octan-4-yl)methanol;(1-oxo-2,6,7-trioxa-15-phosphabicyclo[2.2.2]octan-4-yl)methanol;2,6,7-Trioxa-1-phosphabicyclo[2,2,2]octane-4-methanol, 1-oxide;2,6,7-Trioxa-1-phosphabicyclo[2.2.2]octane-4-methanol,1-oxide;4-(hydroxymethyl)-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane-1-one;4-Hydroxymethyl-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane 1-Oxide;4-(HYDROXYMETHYL)-2,6,7-TRIOXA-1??-PHOSPHABICYCLO[2.2.2]OCTAN-1-ONE;4-(HYDROXYMETHYL)-2,6,7-TRIOXA-1-PHOSPHABICYCLO[2.2.2]OCTANE 1-OXIDE;PENTAERYTHRITOL PHOSPHATE ALCOHOL

Chemical Property of 4-(Hydroxymethyl)-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane 1-oxide

Chemical Property:

• Vapor Pressure: 0.000872mmHg at 25°C
• Melting Point: 209-212 °C
• Refractive Index: 1.502
• Boiling Point: 270.9 °C at 760 mmHg
• PKA: 13.70±0.10(Predicted)
• Flash Point: 117.6 °C
• PSA: 74.80000
• Density: 1.53 g/cm³
• LogP: 0.15020
• XLogP3: -1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 180.01876038
• Heavy Atom Count: 11
• Complexity: 184

Purity/Quality:

98%, ^*data from raw suppliers

4-Hydroxymethyl-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane 1-Oxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2(COP(=O)(O1)OC2)CO
• Uses: suzuki reaction 4-(Hydroxymethyl)-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane 1-Oxide is flame retardant; used in preparation method of green environmental protection polymer hard wall decoration material.

Technology Process of 4-(Hydroxymethyl)-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane 1-oxide

There total 2 articles about 4-(Hydroxymethyl)-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane 1-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: 95.0%

Pentaerythritol (115-77-5) → 4-(hydroxymethyl)-1-oxido-2,6,7-trioxa-1-phosphabicyclo [2.2.2] octane (5301-78-0)

Guidance literature:

With trichlorophosphate;

DOI:10.1080/10426500701807491

Reference yield: 85.0%

Pentaerythritol (115-77-5) + trichlorophosphate (10025-87-3,12599-09-6,63736-95-8,39380-77-3) → 4-(hydroxymethyl)-1-oxido-2,6,7-trioxa-1-phosphabicyclo [2.2.2] octane (5301-78-0)

Guidance literature:

In 1,4-dioxane; at 20 - 95 ℃; Inert atmosphere; Reflux; Large scale;

Reference yield: 93.1%

P,P-dichlorophenylphosphine oxide (824-72-6) + 4-(hydroxymethyl)-1-oxido-2,6,7-trioxa-1-phosphabicyclo [2.2.2] octane (5301-78-0) → C16H21O11P3

Guidance literature:

With 1-hexyl-3-methylimidazolium hydrogen sulphate; In acetonitrile; at 80 ℃; for 4h; Solvent; Reagent/catalyst; Temperature;

upstream raw materials:

Pentaerythritol

trichlorophosphate

Downstream raw materials:

1-oxo-4-chlorocarbonyl-1-phospha-2,6,7-trioxabicyclo[2.2.2]octane

Benzoic acid 1-oxo-2,6,7-trioxa-1λ⁵-phospha-bicyclo[2.2.2]oct-4-ylmethyl ester

(1-oxido-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octan-4-yl)methyl 4-methylbenzenesulfonate

Refernces

• 1、 Jia, Puyou,Zhang, Meng,Hu, Lihong,Feng, Guodong,Zhou, Yonghong. "Synthesis of novel caged phosphate esters and their flame retardant effect on poly(vinyl chloride) blends". . p. 1220 - 1222. Retrieved 2015.
• 2、 Zhang, Yi. "Synthesis and characterization of PEDSCD and its application as a flame retardant in epoxy resins". . p. 34849 - 34859. Retrieved 2021/12/02.
• 3、 Sheng, Xijun,Zhou, Yuan,Zhang, Shasha,Peng, Hao,He, Hongwu. "Synthesis and Biological Activity of 4-[(Substituted Phenoxyacetoxy)methyl]-2,6,7-trioxa-1-phosphabicyclo[2.2.2]octane-1-one". . p. 165 - 170. Retrieved 2017/02/03.