(R)-(-)-1,1'-BINAPHTHYL-2,2'-DIOXYCHLOROPHOSPHINE

Base Information

• Chemical Name: (R)-(-)-1,1'-BINAPHTHYL-2,2'-DIOXYCHLOROPHOSPHINE
• CAS No.: 137156-22-0
• Molecular Formula: C₂₀H₁₂ClO₂P
• Molecular Weight: 350.741
• Mol file: 137156-22-0.mol

Synonyms:(R)-(-)-1,1'-BINAPHTHYL-2,2'-DIOXYCHLOROPHOSPHINE;(S)-(+)-1,1'-BINAPHTHYL-2,2'-DIOXYCHLOROPHOSPHINE;(S)-(+)-Chlorodinaphthol[2,1-d:1',2'-f][1,3,2]dioxaphosphepin,min.97%;(S)-(+)-4-CHLORODINAPHTHOL[2,1-D:1'',2''-F][1,3,2]DIOXAPHOSPHEPIN, MIN. 97%

Chemical Property of (R)-(-)-1,1'-BINAPHTHYL-2,2'-DIOXYCHLOROPHOSPHINE

Chemical Property:

• Boiling Point: 518.5±19.0 °C(Predicted)
• PSA: 32.05000
• LogP: 6.89690
• Sensitive.: moisture sensitive

Purity/Quality:

98%Min ^*data from raw suppliers

(S)-(+)-4-Chlorodinaphthol[2,1-d:1',2'-f][1,3,2]dioxaphosphepin, min. 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (R)-(-)-1,1'-BINAPHTHYL-2,2'-DIOXYCHLOROPHOSPHINE

There total 3 articles about (R)-(-)-1,1'-BINAPHTHYL-2,2'-DIOXYCHLOROPHOSPHINE 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%

1,1'-bi-2-naphthol (602-09-5) → binaphthol chlorophosphite (137156-22-0,171878-71-0,155613-52-8)

Guidance literature:

With water; phosphorus trichloride; for 5h; Heating;

Reference yield:

(R)-1,1'-Bi-2-naphthol (18531-94-7) → binaphthol chlorophosphite (137156-22-0,171878-71-0,155613-52-8)

Guidance literature:

With triethylamine; phosphorus trichloride; In toluene; at -60 - 20 ℃; for 2.25h;

DOI:10.1002/1521-3765(20010202)7:3<671::AID-CHEM671>3.0.CO;2-M

Reference yield:

(S)-[1,1']-binaphthalenyl-2,2'-diol (18531-99-2) → binaphthol chlorophosphite (137156-22-0,171878-71-0,155613-52-8)

Guidance literature:

With triethylamine; phosphorus trichloride; In tetrahydrofuran; at -40 ℃;

DOI:10.1039/c39910001292

upstream raw materials:

(S)-[1,1']-binaphthalenyl-2,2'-diol

1,1'-bi-2-naphthol

(R)-1,1'-Bi-2-naphthol

Downstream raw materials:

(+/-)-2-(1,3-bis(diphenylphosphino)-2-propoxy)dinaphtho[2,1-d:4,3-f]-1,3-dioxa-2-phosphepin

(R)-2'-diphenylphosphino-6-vibyl-1,1'-binaphthalen-2-yl (S)-1,1'-binaphthalene-2,2'-diyl phosphite

(2'R,4'S,5'R)-2-[(5'-vinylquinuclidyl-2')methoxy]dinaphtho[2,1-d:1',2'-f](1,3,2) dioxaphosphepine

(2'R)-2-(2'-dibenzylamino-3'-methyl-butoxy)dinaphtho[2,1-d:1',2'-f](1,3,2)dioxaphosphepine

Refernces

• 1、 Yan, Ming,Xu, Qian-Yong,Chan, Albert S.C.. "Asymmetric hydrocyanation of olefins catalyzed by chiral diphosphite-nickel complexes". . p. 845 - 849. Retrieved 2000.
• 2、 Bredikhin,Bredikhina,Nigmatzyanov. "On the use of seven-membered phosphorous heterocycles based on 2,2′-dihydroxy-1,1′-binaphthalene and 1,4:3,6-dianhydro-D-mannitol in the 31P NMR analysis of the enantiomeric composition of chiral alcohols". . p. 411 - 416. Retrieved 1998.
• 3、 Korch, Katerina M.,Watson, Donald A.. "Total Synthesis of (±)-Impatien A via Aza-Heck Cyclization". supporting information. p. 7285 - 7289. Retrieved 2021/09/14.
• 4、 Moritz, Jan-Ole,Chakrabortty, Soumyadeep,Bernd H. Mu.ller,Spannenberg, Anke,Kamer, Paul C. J.. "P-chirogenic diphosphazanes with axially chiral substituents and their use in rh-catalyzed asymmetric hydrogenation". . p. 14537 - 14544. Retrieved 2020/12/29.