(S)-3-(tert-butyl)-4-(2,6-di methoxyphenyl)-2,3-dihyd robenzo[d][1,3]oxaphosph ole

Base Information

• Chemical Name: (S)-3-(tert-butyl)-4-(2,6-di methoxyphenyl)-2,3-dihyd robenzo[d][1,3]oxaphosph ole
• CAS No.: 1373432-09-7
• Molecular Formula: C₁₉H₂₃O₃P
• Molecular Weight: 330.364
• Hs Code.: 2931499090
• Mol file: 1373432-09-7.mol

Synonyms:

Chemical Property of (S)-3-(tert-butyl)-4-(2,6-di methoxyphenyl)-2,3-dihyd robenzo[d][1,3]oxaphosph ole

Chemical Property:

• Boiling Point: 422.1±45.0 °C(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

97%, 99%ee ^*data from raw suppliers

(S)-3-(t-Butyl)-4-(2,6-dimethoxyphenyl)-2,3-dihydrobenzo[d][1,3]oxaphosphole, min. 97% (S)-BI-DIME min. 97% (S)-BI-DIME ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-(tert-butyl)-4-(2,6-di methoxyphenyl)-2,3-dihyd robenzo[d][1,3]oxaphosph ole

There total 14 articles about (S)-3-(tert-butyl)-4-(2,6-di methoxyphenyl)-2,3-dihyd robenzo[d][1,3]oxaphosph ole 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%

(R)-3-(tert-butyl)-4-(2,6-dimethoxyphenyl)-2,3 dihydrobenzo[d][1,3]oxaphosphole-3-oxide (1373432-34-8) → (S)-3-tert-butyl-4-(2,6-dimethoxyphenyl)-2,3-dihydrobenzo[d][1,3]oxaphosphole (1246888-90-3,1338454-03-7,1373432-09-7)

Guidance literature:

With titanium(IV) isopropylate; In tetrahydrofuran; at 70 ℃; for 16h; stereospecific reaction; Inert atmosphere;

DOI:10.1039/c3cc46009f

Reference yield: 90.0%

(S)-3-(tert-butyl)-4-(2,6-dimethoxyphenyl)-2H-benzo[d][1,3]oxaphosphole 3-oxide (1338453-99-8) → (R)-BIDIME (1246888-90-3,1338454-03-7,1373432-09-7)

Guidance literature:

With titanium(IV) isopropylate; In tetrahydrofuran;

DOI:10.1021/jacs.5b03760

Reference yield: 85.0%

3-(t-butyl)-4-(2,6-dimethoxyphenyl)-2,3-dihydrobenzo[d][1,3]oxaphosphole-3-oxide (1246888-86-7) → rac-3-(tert-butyl)-4-(2,6-dimethoxyphenyl)-2,3-dihydrobenzo[d][1,3]oxaphosphole (1246888-90-3,1338454-03-7,1373432-09-7)

Guidance literature:

3-(t-butyl)-4-(2,6-dimethoxyphenyl)-2,3-dihydrobenzo[d][1,3]oxaphosphole-3-oxide; With titanium(IV) isopropylate; In tetrahydrofuran; at 20 ℃; Reflux;

With sodium hydroxide; In tetrahydrofuran; at 60 ℃;

DOI:10.1002/anie.201002404

upstream raw materials:

3-(t-butyl)-4-(2,6-dimethoxyphenyl)-2,3-dihydrobenzo[d][1,3]oxaphosphole-3-oxide

tert-butyl(2,6-dimethoxyphenyl)(methyl)phosphine oxide

(2,6-dimethoxyphenyl)lithium

racemic 3-tert-butyl-2,3-dihydrobenzo[d][1,3]oxaphosphol-4-ol oxide

Refernces

• 1、 Handa, Sachin,Andersson, Martin P.,Gallou, Fabrice,Reilly, John,Lipshutz, Bruce H.. "HandaPhos: A General Ligand Enabling Sustainable ppm Levels of Palladium-Catalyzed Cross-Couplings in Water at Room Temperature". supporting information. p. 4914 - 4918. Retrieved 2016/04/26.
• 2、 Sieber, Joshua D.,Qu, Bo,Rodríguez, Sonia,Haddad, Nizar,Grinberg, Nelu,Lee, Heewon,Song, Jinhua J.,Yee, Nathan K.,Senanayake, Chris H.. "Synthesis of P-Chiral Dihydrobenzooxaphospholes Through Negishi Cross-Coupling". . p. 729 - 736. Retrieved 2016/01/25.