Pyridine-triphenylborane

Base Information

• Chemical Name: Pyridine-triphenylborane
• CAS No.: 971-66-4
• Molecular Formula: C23H20BN
• Molecular Weight: 321.229
• Hs Code.: 2933399090
• DSSTox Substance ID: DTXSID20448581
• Mol file: 971-66-4.mol

Synonyms:pyridine triphenylborane

Chemical Property of Pyridine-triphenylborane

Chemical Property:

• Vapor Pressure: 0.000104mmHg at 25°C
• Melting Point: 214-215 °C (decomp)
• Boiling Point: 348 °C at 760 mmHg
• Flash Point: 161.1 °C
• PSA: 8.39000
• LogP: 3.28440
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 321.1688798
• Heavy Atom Count: 25
• Complexity: 233

Purity/Quality:

99% ^*data from raw suppliers

Triphenyl(pyridin-1-ium-1-yl)borate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3.C1=CC=NC=C1

Technology Process of Pyridine-triphenylborane

There total 13 articles about Pyridine-triphenylborane 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: 85.0%

sodium tetraphenyl borate (143-66-8) + copper(ll) bromide (7789-45-9) → triphenylborane pyridine complex (971-66-4) + tetraphenyl-boric acid ; copper (I)-salt (14637-33-3)

Guidance literature:

With pyridine; In 1,2-dimethoxyethane; byproducts: NaBr, biphenyl; CuBr2 added to NaBPh4 soln.; mixt. stirred at 25°C for 48 h; DME removed in vac.; residue extd. under N2 with hexane and diethyl ether; pyridine added to combined extracts; Ph3B*pyridine ppt. filtered and recrystd.; identified by m.p. and IR spectrum; filtrate evapd. to give biphenyl; further extn. of reactn. residue by THF; ext. evapd. under N2 to give CuBPh4;

DOI:10.1016/0022-328X(94)87003-9

Reference yield: 83.0%

bis(η5-1,2,4-tri-tert-butylcyclopentadienyl)U(O)(pyridine) (863607-63-0) + triphenylborane (960-71-4) → triphenylborane pyridine complex (971-66-4) + bis(1,2,4-tri-tert-butylcyclopentadienyl)uranium oxide (863607-65-2)

Guidance literature:

In toluene; (N2); addn. of a soln. of boron compd. in toluene to a soln. of uranium complex in toluene at room temp., stirring for 2 h; rvapn., extn. with pentane, filtration, concn., cooling to -20°C,filtration; elem. anal.;

DOI:10.1021/om050406q

Reference yield: 75.0%

pyridine (110-86-1) + bromobenzene (108-86-1,52753-63-6) + boron trifluoride diethyl etherate (109-63-7) → triphenylborane pyridine complex (971-66-4)

Guidance literature:

bromobenzene; boron trifluoride diethyl etherate; With magnesium; In tetrahydrofuran; Inert atmosphere; Reflux;

pyridine; In tetrahydrofuran; at 40 ℃; for 3h; Inert atmosphere;

DOI:10.1002/cjoc.201200775

upstream raw materials:

pyridine

(2,2,6,6-tetramethylpiperidino)2AlI(pyridine)

sodium tetraphenyl borate

silver tetraphenylborate

Downstream raw materials:

4-methoxylbiphenyl

2-methoxy-1,1'-biphenyl

3-methoxybiphenyl

biphenyl

Refernces

• 1、 Wolf, William J.,Lin, Tzu-Pin,Grubbs, Robert H.. "Examining the Effects of Monomer and Catalyst Structure on the Mechanism of Ruthenium-Catalyzed Ring-Opening Metathesis Polymerization". supporting information. p. 17796 - 17808. Retrieved 2019/11/11.
• 2、 Yang, Minghua,Gu, Yongbing,Wang, Yan,Zhao, Xiyu,Yan, Guobing. "Palladium-catalyzed suzuki-miyaura type coupling reaction of aryl halides with triphenylborane-pyridine". . p. 2581 - 2586,6. Retrieved 2020/09/16.