[1-[2-Bis(3,5-dimethylphenyl)phosphanylnaphthalen-1-yl]naphthalen-2-yl]-bis(3,5-dimethylphenyl)phosphane

Base Information

• Chemical Name: [1-[2-Bis(3,5-dimethylphenyl)phosphanylnaphthalen-1-yl]naphthalen-2-yl]-bis(3,5-dimethylphenyl)phosphane
• CAS No.: 145416-77-9
• Molecular Formula: C₅₂H₄₈P₂
• Molecular Weight: 734.901
• Hs Code.: 29310099
• European Community (EC) Number: 681-146-8,681-153-6,682-114-6
• Nikkaji Number: J1.535.409G,J2.376.180G,J986.374E
• Mol file: 145416-77-9.mol

Synonyms:135139-00-3;137219-86-4;(R)-DM-BINAP;(S)-DM-BINAP;145416-77-9;(R)-3,5-XYLYL-BINAP;DM-BINAP;(S)-(-)-2,2'-Bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl;[1-[2-bis(3,5-dimethylphenyl)phosphanylnaphthalen-1-yl]naphthalen-2-yl]-bis(3,5-dimethylphenyl)phosphane;(R)-2,2'-Bis(bis(3,5-dimethylphenyl)phosphino)-1,1'-binaphthalene;(R)-(+)-2,2'-BIS[DI(3,5-XYLYL)PHOSPHINO]-1,1'-BINAPHTHYL;2,2'-bis(di-3,5-xylylphosphino)-1,1'-binaphthyl;(R)-(+)-XYLBINAP;(S)-(-)-XYLBINAP;(R)-2,2'-Bis(di-3,5-xylylphosphino)-1,1'-binaphthyl;(R)-(+)-2,2'-Bis(di-3,5-xylylphosphino)-1,1'-binaphthyl;2,2'-bis[di(3,5-dimethylphenyl)phosphino]-1,1'-binaphthyl;(s)-2,2'-bis[bis(3,5-dimethylphenyl)phosphino]-1,1'-binaphthyl;2,2'-BIS[BIS(3,5-DIMETHYLPHENYL)PHOSPHINO]-1,1'-BINAPHTHYL;MFCD01630821;Phosphine, 1,1'-[(1R)-[1,1'-binaphthalene]-2,2'-diyl]bis[1,1-bis(3,5-dimethylphenyl)-;2,2'-bis(bis(3,5-dimethylphenyl)phosphino)-1,1'-binaphthyl;(S)-XYLYL-BINAP;SCHEMBL29122;DM-BINAP, 97%;MXGXXBYVDMVJAO-UHFFFAOYSA-N;(R)-(+)-2,2-Bis(di-3,5-Xylylphosphino)-1,1-Binaphthyl;AMY11706;AKOS015842419;SC11258;PHOSPHINE,1,1'-[[1,1'-BINAPHTHALENE]-2,2'-DIYL]BIS[1,1-BIS(3,5-DIMETHYLPHENYL)-;AS-71885;SY068476;SY071848;FT-0705449;X0070;X0071;D70872;E77594;F73426;A887748;J-006651;J-006985;J-008102;2,2'-Bis[bis(3,5-xylyl)phosphino]-1,1'-binaphthalene;(S)-2,2'-bis[di(3,5-xylyl)phosphino]-1,1'-binaphthyl;(S)-(-)-2,2'-Bis(di(3,5-xylyl)phosphino)-1,1'-binaphtyl;2,2'-BIS[DI(3,5-XYLYL)PHOSPHINO]-1,1'-BINAPHTHYL;(S)-(-)-2,2\'-Bis[di(3,5-xylyl)phosphino]-1,1\'-binaphthyl;(S)-2,2'-Bis(bis(3,5-dimethylphenyl)phosphino)-1,1'-binaphthalene;2,2'-Bis(bis(3,5-dimethylphenyl)phosphino)-1,1'-binaphthalene;(aR)-2,2'-Bis[bis(3,5-dimethylphenyl)phosphino]-1,1'-binaphthalene;(S)-(-)-2,2'-Bis(di-(3,5-dimethylphenyl)phosphino) -1,1'-binaphthyl ((S)-Xylyl-BINAP);(R)-2,2 inverted exclamation mark -Bis(di-3,5-xylylphosphino)-1,1 inverted exclamation mark -binaphthyl;(S)-2,2 inverted exclamation mark -Bis(di-3,5-xylylphosphino)-1,1 inverted exclamation mark -binaphthyl;{2'-[BIS(3,5-DIMETHYLPHENYL)PHOSPHANYL]-[1,1'-BINAPHTHALEN]-2-YL}BIS(3,5-DIMETHYLPHENYL)PHOSPHANE

Chemical Property of [1-[2-Bis(3,5-dimethylphenyl)phosphanylnaphthalen-1-yl]naphthalen-2-yl]-bis(3,5-dimethylphenyl)phosphane

Chemical Property:

• Appearance/Colour: Pale yellow crystalline powder
• Melting Point: 254-259 °C
• PSA: 27.18000
• LogP: 11.64360
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 14.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 7
• Exact Mass: 734.32312553
• Heavy Atom Count: 54
• Complexity: 999

Purity/Quality:

98% ^*data from raw suppliers

2,2'-Bis(di-3,5-xylylphosphino)-1,1'-binaphthyl 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:
• Hazard Codes: R36/37/38:
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=CC(=C1)P(C2=C(C3=CC=CC=C3C=C2)C4=C(C=CC5=CC=CC=C54)P(C6=CC(=CC(=C6)C)C)C7=CC(=CC(=C7)C)C)C8=CC(=CC(=C8)C)C)C

Technology Process of [1-[2-Bis(3,5-dimethylphenyl)phosphanylnaphthalen-1-yl]naphthalen-2-yl]-bis(3,5-dimethylphenyl)phosphane

There total 15 articles about [1-[2-Bis(3,5-dimethylphenyl)phosphanylnaphthalen-1-yl]naphthalen-2-yl]-bis(3,5-dimethylphenyl)phosphane 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: 96.0%

2,2'-bis[di-(3,5-dimethylphenyl)phosphoryl]-1,1'-binaphthyl (137219-84-2,137219-85-3,137244-17-8) → 2,2'-bis[di(3,5-dimethylphenyl)phosphino]-1,1'-binaphthyl (137219-86-4,145416-77-9,135139-00-3)

Guidance literature:

With trichlorosilane; triethyl phosphite; In tetrahydrofuran; toluene; at 100 ℃; for 2h;

DOI:10.1021/ol048227c

Reference yield: 84.7%

(R)-(-)-1,1'-bi-2-naphthol triflate (128544-05-8,128575-34-8,141807-44-5,126613-06-7) + bis-(3,5-dimethylphenyl)chlorophosphine (74289-57-9) → 2,2'-bis[di(3,5-dimethylphenyl)phosphino]-1,1'-binaphthyl (137219-86-4,145416-77-9,135139-00-3)

Guidance literature:

With magnesium; In N,N-dimethyl-formamide; at 110 ℃; for 12.5h;

Reference yield: 75.0%

bis(3,5-dimethylphenyl)bromophosphine (1342819-37-7) + 2,2'-dibromo-1,1'-binaphthyl (74866-28-7,86688-08-6,150024-49-0) → 2,2'-bis[di(3,5-dimethylphenyl)phosphino]-1,1'-binaphthyl (137219-86-4,145416-77-9,135139-00-3)

Guidance literature:

2,2'-dibromo-1,1'-binaphthyl; With iodine; magnesium; In tetrahydrofuran; toluene; at 60 - 75 ℃; for 4h; Inert atmosphere;

bis(3,5-dimethylphenyl)bromophosphine; In tetrahydrofuran; toluene; at 60 ℃; for 3h;

DOI:10.1002/chem.201101467

upstream raw materials:

(S)-2,2'-bis((trifluoromethanesulfonyl)oxy)-1,1'-binaphthyl

5-bromo-1,3-xylene

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

bis(3,5-dimethylphenyl)phosphine oxide

Downstream raw materials:

(S)-2,2'-bis-1,1'-binaphthyl

[RuCl(p-cymene)((S)-xylbinap)]Cl

[Cl2Ru((R)-2,2'-bis(3,5-xylylphosphino)-1,1'-binaphthyl)(κN3-1-methylbenzimidazole)2]

Refernces

• 1、 Yu, Jeongjae,Armstrong, Daniel W.,Ryoo, Jae Jeong. "Synthesis of new C3 symmetric amino acid- and aminoalcohol-containing chiral stationary phases and application to HPLC enantioseparations". . p. 74 - 84. Retrieved 2017/12/26.
• 2、 -. "NOVEL RUTHENIUM COMPLEX AND PROCESS FOR PRODUCING OPTICALLY ACTIVE ALCOHOL COMPOUND USING SAME AS CATALYST". Paragraph 0064. . Retrieved 2014/03/21.