1,1'-Ferrocene diboronic acid pinacol ester

Base Information

• Chemical Name: 1,1'-Ferrocene diboronic acid pinacol ester
• CAS No.: 737776-93-1
• Molecular Formula: C22H32 B2 Fe O4
• Molecular Weight: 437.958
• Hs Code.: 29319090
• European Community (EC) Number: 679-570-3
• Mol file: 737776-93-1.mol

Synonyms:1,1'-Ferrocene diboronic acid pinacol ester;737776-93-1;1,1'-Ferrocenediboronic acid bis(pinacol) ester;1,1'-FERROCENEDIBORONIC ACID BIS(PINACOL) ESTER, 97%;AB25234;1,1'-Ferrocenediboronic acid bis(pinacol)ester,97%;1,1'-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ferrocene;98%

Chemical Property of 1,1'-Ferrocene diboronic acid pinacol ester

Chemical Property:

• Melting Point: 191 °C(lit.)
• PSA: 36.92000
• LogP: 4.31070
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 438.183605
• Heavy Atom Count: 29
• Complexity: 203

Purity/Quality:

97% ^*data from raw suppliers

1,1'-Bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ferrocene >98.0%(GC)(T) ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)[C]2[CH][CH][CH][CH]2.B1(OC(C(O1)(C)C)(C)C)[C]2[CH][CH][CH][CH]2.[Fe]

Technology Process of 1,1'-Ferrocene diboronic acid pinacol ester

There total 3 articles about 1,1'-Ferrocene diboronic acid pinacol ester 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: 79.0%

1,2-bis(dimethylamino)-1,2-dibora-[2]ferrocenophane (191734-85-7) + bis(pinacol)diborane (73183-34-3) → 1,1′-ferrocenediboronic acidbis(pinacol)ester (737776-93-1)

Guidance literature:

In n-heptane; under dry Ar using standard Schlenk or glove box techniques; soln. of ((C5H4)(BNMe2))2Fe (0.11 mmol) mixed with soln. of bis(pinacolato)diborane(0.11 mmol); refluxed (6 h); dried (vac.); residue extd. into hexane;

DOI:10.1002/ejic.200900772

Reference yield: 61.0%

ferrocene (102-54-5,55404-68-7) + bis(pinacol)diborane (73183-34-3) → (4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)ferrocene (112579-52-9) + 1,1′-ferrocenediboronic acidbis(pinacol)ester (737776-93-1)

Guidance literature:

With catalyst:(IrOMe(cod))2/4,4'-di-tBu-2,2'-bipy; In octane; under Ar; (Ir(OMe)(cod))2 (0.015 mmol), 4,4'-di-tert-butyl-2,2'-bipyridine (0.03 mmol), bis(pinacolato)diboron (6.0 mmol) placed in Schlenk tube; octane and ferrocene (2.0 mmol) added; mixt. refluxed at 126°C for 24 h; column chromy. (silica gel, cyclohexane/ethyl acetate);

DOI:10.1039/b403419h

Reference yield: 35.0%

1,2-bis(dimethylamino)-1,2-dibora-[2]ferrocenophane (191734-85-7) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 1,1′-ferrocenediboronic acidbis(pinacol)ester (737776-93-1)

Guidance literature:

In n-heptane; under dry Ar using standard Schlenk or glove box techniques; soln. of ((C5H4)(BNMe2))2Fe (0.21 mmol) added to soln. of pinacolborane (0.21 mmol); refluxed (ca. 2 h); dried (vac.); residue extd. into hexane; filtered; solvent removed (vac.);

DOI:10.1002/ejic.200900772

upstream raw materials:

ferrocene

bis(pinacol)diborane

1,2-bis(dimethylamino)-1,2-dibora-[2]ferrocenophane

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane