Ferrocenemetaboric acid

Base Information

• Chemical Name: Ferrocenemetaboric acid
• CAS No.: 12152-94-2
• Molecular Formula: C10H11BFeO2
• Molecular Weight: 273.672
• Hs Code.: 29319090
• European Community (EC) Number: 235-272-1
• Mol file: 12152-94-2.mol

Synonyms:Ferrocenemetaboric acid;cyclopenta-1,3-diene;cyclopenta-1,3-dien-1-ylboronic acid;iron(2+);(dihydroxyboranyl)ferrocene;EINECS 235-272-1;STK332032;AKOS003618119;NSC 119337;F0280

Chemical Property of Ferrocenemetaboric acid

Chemical Property:

• Vapor Pressure: 0.00113mmHg at 25°C
• Melting Point: 145-150 °C (dec.)(lit.)
• Boiling Point: 267.1 °C at 760 mmHg
• Flash Point: 115.3 °C
• PSA: 40.46000
• LogP: 0.55620
• Solubility.: slightly sol. in Ether
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 230.020145
• Heavy Atom Count: 14
• Complexity: 129

Purity/Quality:

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

Ferroceneboronic acid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: B(C1=CC=C[CH-]1)(O)O.[CH-]1C=CC=C1.[Fe+2]
• Uses: Redox-acitce electrochemical probe to monitor interactions involving sugarsReactant involved in:Synthesis of ferrocene-appended subporphyrins for electrochemical property studiesSynthesis of catalysts for polymerization of olefinsSuzuki-coupling reaction with organic triflatesCatalytic ortho-lithiation

Technology Process of Ferrocenemetaboric acid

There total 2 articles about Ferrocenemetaboric acid 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: 60.0%

ferrocene (102-54-5,55404-68-7) + boric acid tributyl ester (688-74-4) → 1,1′-ferrocenediboronic acid (12152-94-2,32841-83-1)

Guidance literature:

With potassium hydroxide; n-butyllithium; In diethyl ether; (under N2); addn. of n-BuLi and TMEDA to a stirred soln. of ferrocene in Et2O at room temp., stirred for 6 h, dropwise addn. of the suspn. to a stirred and cooled (-78°C) soln. of borate in Et2O, stirred for 12 h at room temp., hydrolysis (KOH); extg. of the organic layer with KOH, combined aq. layers are acidified with H2SO4, filtn., washing (H2O), drying (P4O10, 0.10mbar), extg. (Et2O);

DOI:10.1016/0022-328X(93)83196-3

Reference yield:

ferrocene (102-54-5,55404-68-7) + boric acid tributyl ester (688-74-4) + potassium hydroxide → 1,1′-ferrocenediboronic acid (12152-94-2,32841-83-1)

Guidance literature:

ferrocene; With n-butyllithium; N,N,N,N,-tetramethylethylenediamine;

boric acid tributyl ester;

potassium hydroxide; With sulfuric acid;

DOI:10.1002/ejic.202100898

Reference yield: 90.0%

1,1′-ferrocenediboronic acid (12152-94-2,32841-83-1) + iodobenzene (591-50-4) → 1,1'-diphenylferrocene

Guidance literature:

With sodium hydroxide; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); In 1,2-dimethoxyethane; water; (under N2); refluxed with vigorous stirring for 6 d; addn. of CHCl3 and water, organic layer is separated, washed with water and dried (MgSO4), solvent removed, column chromy. (silica gel, toluene/hexane (1:5)), crystn. from petroleum ether, monitored by NMR;

DOI:10.1016/0022-328X(93)83196-3

upstream raw materials:

ferrocene

boric acid tributyl ester

Downstream raw materials:

ferrocene

(S)-1,1'-(1,1'-binaphthyl-2,2'-diyl)ferrocene

1,1'-bisnaphthalene

[Fe(η5-C5H4-C6H4-4-C5H4N)2]

Refernces

• 1、 Anson, Christopher E.,Barani, Elham,Bayer, Lea,Breher, Frank,Fink, Karin,Frank, Nils,Powell, Annie K.,Wagner, Hanna E.. "Asymmetrically Difunctionalized 1,1′-Ferrocenyl Metalloligands and Their Transition Metal Complexes". . . Retrieved 2022/01/20.