1,3-Bis((di-tert-butylphosphino)methyl)benzene

Base Information

• Chemical Name: 1,3-Bis((di-tert-butylphosphino)methyl)benzene
• CAS No.: 149968-36-5
• Molecular Formula: C24H44 P2
• Molecular Weight: 394.561
• European Community (EC) Number: 813-340-7
• DSSTox Substance ID: DTXSID10400537
• Nikkaji Number: J644.881J
• Wikidata: Q72445575
• Mol file: 149968-36-5.mol

Synonyms:149968-36-5;1,3-Bis((di-tert-butylphosphino)methyl)benzene;1,3-bis(di-t-butylphosphinomethyl)benzene;1,3-BIS(DI-TERT-BUTYLPHOSPHINOMETHYL)BENZENE;ditert-butyl-[[3-(ditert-butylphosphanylmethyl)phenyl]methyl]phosphane;PCP pincer;MFCD01630850;SCHEMBL1465904;DTXSID10400537;VNLHPVUKSKTUPA-UHFFFAOYSA-N;ZFA96836;m-Xylylenebis(ditert-butylphosphine);Phosphine, [1,3-phenylenebis(methylene)]bis[bis(1,1-dimethylethyl)-;AKOS016009993;CS-W011712;SC11543;BP-12159;1,3-bis(di-t-butylphos-phinomethyl)benzene;FT-0733038;F17087;1,3-bis((ditertiarybutylphosphino)methyl)benzene;A884211;1,3-Bis(di-tert-butylphosphinomethyl)benzene, 97%;J-008649;[1,3-Phenylenebis(methylene)]bis(di-tert-butylphosphane);1,3-BIS(DI-T-BUTYLPHOSPHINOMETHYL)BENZENE;PCP PINCER

Chemical Property of 1,3-Bis((di-tert-butylphosphino)methyl)benzene

Chemical Property:

• Melting Point: 68-75°C
• Boiling Point: 459.3±38.0 °C(Predicted)
• PSA: 27.18000
• LogP: 8.84440
• Sensitive.: air sensitive
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 8
• Exact Mass: 394.29182540
• Heavy Atom Count: 26
• Complexity: 357

Purity/Quality:

98%,99%, ^*data from raw suppliers

1,3-Bis(di-t-butylphosphinomethyl)benzene, 99% ^*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: CC(C)(C)P(CC1=CC(=CC=C1)CP(C(C)(C)C)C(C)(C)C)C(C)(C)C

Technology Process of 1,3-Bis((di-tert-butylphosphino)methyl)benzene

There total 5 articles about 1,3-Bis((di-tert-butylphosphino)methyl)benzene 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: 76.0%

di(tert-butyl)chlorophosphine (13716-10-4) + 1,3-bis-(bromomethyl)benzene (626-15-3) → 1,3-bis[(di-tert-butylphosphino)methyl]benzene (149968-36-5)

Guidance literature:

di(tert-butyl)chlorophosphine; 1,3-bis-(bromomethyl)benzene; In acetonitrile; at 100 ℃; for 15h; Inert atmosphere;

With magnesium; In acetonitrile; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/acs.organomet.5b00671

Reference yield: 42.0%

((C4H9)2PCH2)2C6H3PtClC(2)H2Cl(1+)*B((CF3)2C6H3)4(1-)=((C4H9)2PCH2)2C6H3PtClC(2)H2ClB((CF3)2C6H3)4 (415707-43-6) + hydrogen (1333-74-0) → (2,6-bis[(di-t-butylphosphino)methyl]phenyl)chloroplatinum + ((C4H9)2PCH2)2C6H3PtH2(1+)*B((CF3)2C6H3)4(1-)=((C4H9)2PCH2)2C6H3PtH2B((CF3)2C6H3)4 (415707-41-4) + 1,3-bis[(di-tert-butylphosphino)methyl]benzene (149968-36-5)

Guidance literature:

In dichloromethane-d2; byproducts: Pt; the soln. in CD2Cl2 was left under H2 (4 atm.) at 22°C for 12 d; not sepd., detected by NMR spectra;

DOI:10.1021/om0108651

Reference yield: 31.0%

((C4H9)2PCH2)2C6H3PtH2(1+)*CF3SO3(1-)=((C4H9)2PCH2)2C6H3PtH2CF3SO3 (415707-44-7) + hydrogen (1333-74-0) → (2,6-bis[(di-t-butylphosphino)methyl]phenyl)chloroplatinum + ((C4H9)2PCH2)2C6H3PtCF3SO3 (415707-45-8) + 1,3-bis[(di-tert-butylphosphino)methyl]benzene (149968-36-5)

Guidance literature:

In dichloromethane-d2; byproducts: Pt; the soln. in CD2Cl2 was left under H2 (4 atm.) at 22°C for 12 d; not sepd., detected by NMR spectra;

DOI:10.1021/om0108651

upstream raw materials:

((C₄H₉)2PCH₂)2C₆H₃PtH₂⁽¹⁺⁾*CF₃SO₃^(1-)=((C₄H₉)2PCH₂)2C₆H₃PtH₂CF₃SO₃

hydrogen

((C₄H₉)2PCH₂)2C₆H₃PtClC⁽²⁾H₂Cl⁽¹⁺⁾*B((CF₃)2C₆H₃)4^(1-)=((C₄H₉)2PCH₂)2C₆H₃PtClC⁽²⁾H₂ClB((CF₃)2C₆H₃)4

di(tert-butyl)chlorophosphine

Downstream raw materials:

m-C₆H₄(CH₂(t-Bu)2PNH)2

[RuCl(C₆H₃(CH₂P(C(CH₃)3)2)2)(P(C₆H₅)3)]

[(C₆H₃(CH₂P(C(CH₃)3)2)(CH₂P(C(CH₃)3)(C(CH₃)2CH₂)))RhH]

(2,6-bis[(di-tert-butylphosphino)methyl]phenyl)PdPh

Refernces

• 1、 Ahrens, Alexander,Donslund, Bjarke S.,Gausas, Laurynas,Kristensen, Steffan K.,Skrydstrup, Troels,Sun, Hongwei. "Practical Gas Cylinder-Free Preparations of Important Transition Metal-Based Precatalysts Requiring Gaseous Reagents". supporting information. p. 2300 - 2307. Retrieved 2021/09/28.