(S)-(-)-4-(2-CHLOROPHENYL)-2-HYDROXY-5,5-DIMETHYL-1,3,2-DIOXAPHOSPHORINANE 2-OXIDE

Base Information

• Chemical Name: (S)-(-)-4-(2-CHLOROPHENYL)-2-HYDROXY-5,5-DIMETHYL-1,3,2-DIOXAPHOSPHORINANE 2-OXIDE
• CAS No.: 98674-86-3
• Molecular Formula: C11H14 ClO4 P
• Molecular Weight: 276.657
• Hs Code.: 2919900090
• Mol file: 98674-86-3.mol

Synonyms:1,3,2-Dioxaphosphorinane,4-(2-chlorophenyl)-2-hydroxy-5,5-dimethyl-, 2-oxide, (S)-;(-)-Chlocyphos;(S)-(-)-4-(2-Chlorophenyl)-2-hydroxy-5,5-dimethyl-1,3,2-dioxaphosphorinane-2-oxide;

Chemical Property of (S)-(-)-4-(2-CHLOROPHENYL)-2-HYDROXY-5,5-DIMETHYL-1,3,2-DIOXAPHOSPHORINANE 2-OXIDE

Chemical Property:

• Vapor Pressure: 9.59E-06mmHg at 25°C
• Melting Point: 228-234 °C(lit.)
• Refractive Index: 1.552
• Boiling Point: 357.9°C at 760 mmHg
• Flash Point: 170.3°C
• PSA: 65.57000
• Density: 1.37g/cm³
• LogP: 3.55450
• Storage Temp.: 2-8°C

Purity/Quality:

99.9% ^*data from raw suppliers

(4S)-(-)-4-(2-Chlorophenyl)-5,5-dimethyl-2-hydroxy-1,3,2-dioxaphosphinane 2-oxide ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Use Description: (S)-(-)-4-(2-CHLOROPHENYL)-2-HYDROXY-5,5-DIMETHYL-1,3,2-DIOXAPHOSPHORINANE 2-OXIDE, often referred to as Evans' oxazolidinone, is a versatile compound with significant applications in various fields. In the field of organic chemistry, it serves as a chiral auxiliary, facilitating asymmetric synthesis and the creation of enantiomerically pure compounds. This is particularly valuable in pharmaceutical research and development, where the control of chirality is crucial for drug efficacy and safety. Additionally, it plays a role in medicinal chemistry, enabling the synthesis of novel drug candidates and agrochemicals with improved stereoselectivity. Its utility also extends to the synthesis of complex natural products, aiding in the discovery of new bioactive compounds. Overall, Evans' oxazolidinone plays a pivotal role in advancing asymmetric synthesis and the development of chiral molecules across various scientific disciplines, with its applications ranging from drug discovery to the synthesis of bioactive compounds.

Technology Process of (S)-(-)-4-(2-CHLOROPHENYL)-2-HYDROXY-5,5-DIMETHYL-1,3,2-DIOXAPHOSPHORINANE 2-OXIDE

There total 8 articles about (S)-(-)-4-(2-CHLOROPHENYL)-2-HYDROXY-5,5-DIMETHYL-1,3,2-DIOXAPHOSPHORINANE 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:

(S)-(-)-2-chloro-4-(2-chlorophenyl)-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one → (S)-(-)-4-(2-chlorophenyl)-5,5-dimethyl-2-hydroxy-1,3,2-dioxaphosphorinane-2-oxide (98674-86-3)

Guidance literature:

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

Reference yield:

2-chloro-benzaldehyde (89-98-5) → (S)-(-)-4-(2-chlorophenyl)-5,5-dimethyl-2-hydroxy-1,3,2-dioxaphosphorinane-2-oxide (98674-86-3)

Guidance literature:

Multi-step reaction with 4 steps

1: KOH / ethanol / 5 h / 50 - 60 °C

2: POCl₃, triethylamine / CH₂Cl₂ / 3 h / Heating

3: aq. NaOH / 0.25 h / 90 - 95 °C

With potassium hydroxide; sodium hydroxide; triethylamine; trichlorophosphate; In ethanol; dichloromethane;

DOI:10.1021/jo00223a018

Reference yield:

(+)-4-(2-chlorophenyl)-dihydro-2-hydroxy-5,5-dimethyl-4H-1,3,2-dioxaphosphorin-2-oxide (98634-28-7) → (S)-(-)-4-(2-chlorophenyl)-5,5-dimethyl-2-hydroxy-1,3,2-dioxaphosphorinane-2-oxide (98674-86-3) + (R)-(+)-4-(2-chlorophenyl)-5,5-dimethyl-2-hydroxy-1,3,2-dioxaphosphorinane 2-oxide

Guidance literature:

With barium(II) acetate; In methanol; Solvent; Reagent/catalyst; Resolution of racemate;

DOI:10.1021/ac403686a

upstream raw materials:

(+)-4-(2-chlorophenyl)-dihydro-2-hydroxy-5,5-dimethyl-4H-1,3,2-dioxaphosphorin-2-oxide

2-chloro-benzaldehyde

1-(2'-chlorophenyl)-2,2-dimethyl-1,3-dihydroxy-propane

4-(2-chlorophenyl)-2-chloro-5,5-dimethyl-1,3,2-dioxaphosphorinan 2-oxide

Downstream raw materials:

(S)-7-methoxy-N-propyl-1,2,3,4-tetrahydronaphthalen-2-amine

(5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)propylamine

(2S,4S)-(-)-4-(2-chlorophenyl)-5,5 dimethyl-2--1,3-dioxane

(2S,4S)-(-)-4-(2-chlorophenyl)-5,5-dimethyl-2-(1-methyl-trans-2-phenylethenyl)-1,3-dioxane

Refernces

• 1、 -. "A method for preparing chiral ring phosphoric acid (by machine translation)". . . Retrieved 2017/03/18.
• 2、 Hoeve, Wolter ten,Wynberg, Hans. "The Design of Resolving Agents. Chiral Cyclic Phosphoric Acids". . p. 4508 - 4514. Retrieved 2007/10/02.