[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.: 135139-00-3
• Molecular Formula: C₅₂H₄₈P₂
• Molecular Weight: 734.901
• 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: 135139-00-3.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:

• Melting Point: 189-193 °C
• Boiling Point: 825.347 °C at 760 mmHg
• Flash Point: 485.279 °C
• PSA: 27.18000
• LogP: 11.64360
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility.: Insoluble in water
• 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

(S)-(-)-2,2''-Bis[di-(3,5-dimethylphenyl)phosphino]-1,1''-binaphthyl ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:
• Hazard Codes: R36/37/38:
• Statements: R36/37/38:
• Safety Statements: S26-36/37/39:

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
• Uses: Catalyst for:Asymmetric hydrogenation of benzophenoneRegio- and stereoselective preparation of axially chiral arylnaphthalene derivatives via rhodium-catalyzed [2+2+2] cycloaddition of diynes with naphthalenepropynoic acid derivatives in the presence of chiral biaryl bisphosphine ligandsRegiodivergent rhodium-catalyzed [(2+2)+2] carbocyclization of 1,6-enynes with Me propiolatesLigand controlled regioselective and stereoselective desymmetrizing rhodium-catalyzed allylic arylation of meso cyclopentene dicarbonates with arylboronic acids to form regioisomeric arylcyclopentenolsPlatinum(II) complex-catalyzed enantioselective aldol reaction with ketene silyl acetals in DMF at room temperatureStereoselective preparation of chiral N,O-biaryls via Rh-catalyzed [2+2+2] cycloaddition of conjugate ynamides with diynes

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:

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

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

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

{RuI((S)-2,2'-bis(bis(3,5-dimethylphenyl)phosphino)-1,1'-binaphthyl)(p-cymene)}I

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.