(4R)-2-Hydroxy-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinan 2-oxide

Base Information

• Chemical Name: (4R)-2-Hydroxy-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinan 2-oxide
• CAS No.: 98674-80-7
• Molecular Formula: C11H15 O4 P
• Molecular Weight: 242.211
• Hs Code.: 2934999090
• European Community (EC) Number: 628-971-1
• DSSTox Substance ID: DTXSID70431387
• Nikkaji Number: J1.068.981C,J1.896.641G
• Wikidata: Q76414512
• Mol file: 98674-80-7.mol

Synonyms:98674-80-7;(4R)-2-Hydroxy-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinan 2-oxide;(+)-Phencyphos;(2R,4R)-5,5-Dimethyl-2-hydroxy-4-phenyl-1,3,2-dioxaphosphorinan 2-oxide;(4R)-2-hydroxy-5,5-dimethyl-4-phenyl-1,3,2lambda5-dioxaphosphinane 2-oxide;SCHEMBL3525309;SCHEMBL17942169;DTXSID70431387;PSZSDCWNBXVDFG-SNVBAGLBSA-N;(R)-(-)-2-Hydroxy-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinane 2-oxide;AKOS015913461;(2R,4R)-5,5-Dimethyl-2-hydroxy-4-phenyl-1,3,2dioxaphosphorinan 2-oxide;(4R)-2-Hydroxy-4alpha-phenyl-5,5-dimethyl-1,3,2-dioxaphosphorinane-2-one;(4R)-2-Hydroxy-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphinane 2-oxide;(4R)-2-Hydroxy-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphinane2-oxide;(2R,4R)-5,5-DIMETHYL-2-HYDROXY-4-PHENYL-1,3,2-DIOXAPHOSPHORINAN2-OXIDE;(4R)-2-Hydroxy-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinan 2-oxide, 98%

Chemical Property of (4R)-2-Hydroxy-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinan 2-oxide

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 224-227 °C(lit.)
• Refractive Index: 1.538
• Boiling Point: 344.4°Cat760mmHg
• Flash Point: 162.1°C
• PSA: 65.57000
• Density: 1.27g/cm³
• LogP: 2.90110
• Storage Temp.: 2-8°C
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 242.07079595
• Heavy Atom Count: 16
• Complexity: 296

Purity/Quality:

98%,99%, ^*data from raw suppliers

(4R)-2-Hydroxy-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinan 2-oxide 98% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(COP(=O)(OC1C2=CC=CC=C2)O)C
• Isomeric SMILES: CC1(COP(=O)(O[C@@H]1C2=CC=CC=C2)O)C
• Uses: (4R)-2-Hydroxy-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinan 2-oxide can be used:As a reactant in the phosphoalkoxylation of aromatic enones.As a chiral resolving agent in the resolution of amino acids, amines, and amino alcohols.

Technology Process of (4R)-2-Hydroxy-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinan 2-oxide

There total 10 articles about (4R)-2-Hydroxy-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinan 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:

(R)-(-)-2-chloro-4-(phenyl)-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one → (R)-(-)-5,5-dimethyl-2-hydroxy-4-phenyl-1,3,2-dioxaphosphorinane 2-oxide (98674-80-7)

Guidance literature:

With sodium hydroxide; at 90 ℃; for 1h;

Reference yield:

2-chloro-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinane 2-oxide (98675-02-6) → (-)-2-hydroxy-2-oxo-5,5-dimethyl-4-(R)-phenyl-1,3,2-dioxaphosphorinane (98674-80-7)

Guidance literature:

2-chloro-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinane 2-oxide; With sodium hydroxide; at 95 ℃;

With (1S, 2S)-(+)-2-amino-1-phenyl-1, 3-propanediol; Further stages.;

DOI:10.1021/ja004084n

Reference yield:

1-phenyl-2,2-dimethyl-1,3-propanediol (33950-46-8,98674-79-4) → (-)-2-hydroxy-2-oxo-5,5-dimethyl-4-(R)-phenyl-1,3,2-dioxaphosphorinane (98674-80-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: POCl₃; Et₃N / CH₂Cl₂ / 3 h / Heating

2.1: aq. NaOH / 95 °C

2.2: (+)-2-amino-1-phenyl-1,3-propanediol

With sodium hydroxide; triethylamine; trichlorophosphate; In dichloromethane; 2.2: racemate resolution;

DOI:10.1021/ja004084n

upstream raw materials:

5,5-dimethyl-2-hydroxy-4-phenyl-1,3,2-dioxaphosphorinane 2-oxide

1-phenyl-2,2-dimethyl-1,3-propanediol

benzaldehyde

2-chloro-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinane 2-oxide

Downstream raw materials:

(-)-(R)-2-chloro-2-oxo-5,5-dimethyl-4-(R)-phenyl-1,3,2-dioxaphosphorinane

(2R,4S)-(+)-5,5 dimethyl-2--4-phenyl-1,3-dioxane

(2R,4S)-(+)-5,5-dimethyl-4-phenyl-2-(1-methyl-trans-2-phenylcyclopropyl)-1,3-dioxane

(2R,4S)-(+)-5,5-dimethyl-4-phenyl-2-(trans-2-phenylcyclopropyl)-1,3-dioxane

Refernces

• 1、 Cullis,Fawcett,Griffith,Harger,Lee. "Mechanism and stereochemistry of diphosphate formation from dioxaphosphorinanes: A critical reassessment". . p. 4147 - 4154. Retrieved 2007/10/03.