1,1,2,2-Tetrakis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethene CAS#: 1660996-72-4; 凯望编码 (ChemWhat Code): 1491394

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

英文名1,1,2,2-Tetrakis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethene
IUPAC Name4,4,5,5-tetramethyl-2-[4-[1,2,2-tris[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethenyl]phenyl]-1,3,2-dioxaborolane 
分子结构structure of 1,1,2,2-Tetrakis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethene CAS 1660996-72-4
CAS编号 1660996-72-4
别名1,1,2,2-Tetrakis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethene
1660996-72-4
YSZC726
MFCD31700765
4,4,5,5-tetramethyl-2-[4-[1,2,2-tris[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethenyl]phenyl]-1,3,2-dioxaborolane
AS-85909
CS-0110315
E74367
2,2′,2”,2”’-(1,1,2,2-Ethenetetrayltetra-4,1-phenylene)tetrakis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)
分子式C50H64B4O8
分子量836.3 
InChIInChI=1S/C50H64B4O8/c1-43(2)44(3,4)56-51(55-43)37-25-17-33(18-26-37)41(34-19-27-38(28-20-34)52-57-45(5,6)46(7,8)58-52)42(35-21-29-39(30-22-35)53-59-47(9,10)48(11,12)60-53)36-23-31-40(32-24-36)54-61-49(13,14)50(15,16)62-54/h17-32H,1-16H3
InChI KeyIMKQIUDDYPXPIU-UHFFFAOYSA-N
SMILESB1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)C(=C(C3=CC=C(C=C3)B4OC(C(O4)(C)C)(C)C)C5=CC=C(C=C5)B6OC(C(O6)(C)C)(C)C)C7=CC=C(C=C7)B8OC(C(O8)(C)C)(C)C 

Physical Data

No data available

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Temperature (NMR Spectroscopy), °C Frequency (NMR Spectroscopy), MHz
Chemical shifts, Spectrum1Hchloroform-d124.84
Chemical shifts, Spectrum1Hchloroform-d1
Chemical shifts1Hchloroform-d1400
Chemical shifts1Hchloroform-d1300
Chemical shifts1Hchloroform-d1400
Chemical shifts1Hchloroform-d1
Chemical shifts13Cchloroform-d1
1,1,2,2-Tetrakis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethene CAS#: 1660996-72-4 NMRNMR of 1,1,2,2-Tetrakis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethene CAS 1660996-72-4
Description (IR Spectroscopy)Solvent (IR Spectroscopy)
Bandspotassium bromide
Bands, Spectrum

Route of Synthesis (ROS)

Route of Synthesis (ROS) of 1,1,2,2-Tetrakis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethene CAS 1660996-72-4
Route of Synthesis (ROS) of 1,1,2,2-Tetrakis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethene CAS 1660996-72-4
ConditionsYield
Stage #1: 1,1,2,2-tetrakis(4-bromophenyl)ethene; bis(pinacol)diborane With potassium acetate In 1,4-dioxane for 1h; Inert atmosphere;
Stage #2: With (1,1′-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane Inert atmosphere;

Experimental Procedure
5.1 (1) Preparation of tetrakis (pinacol borate) tetraphenylene
Put tetrabromotetraphenylethylene (0.1mmol), bipinacol borate (1.0mmol), potassium acetate (1mmol) into the 1,4-dioxane solvent single-neck bottle equipped with 30mL, pass nitrogen 60 minute. Weigh 1,1′-bisdiphenylphosphinoferrocene palladium dichloride, put it into the above-mentioned single-necked flask, and let it pass nitrogen for half an hour. Continue heating to reflux in a nitrogen atmosphere overnight, cool the reaction system, pour the reaction solution into a beaker containing 500 mL of water, and extract with dichloromethane. The organic phase was collected and dried, mixed with silica gel, and sampled by dry method, and purified by column using dichloromethane/methanol (volume ratio of 10:1) as a developing solvent to obtain the intermediate tetrakis (pinacol borate) tetraphenyl Ethylene, 85% yield.		85%
With (1,1′-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane Inert atmosphere; Reflux;

Experimental Procedure
5.1 (1) Preparation of tetrakis (pinacol borate) tetraphenylene
Put tetrabromotetraphenylethylene (0.1mmol), bipinacol borate (1.0mmol), potassium acetate (1mmol) into the 1,4-dioxane solvent single-neck bottle equipped with 30mL, pass nitrogen 60 minute. Weigh 1,1′-bisdiphenylphosphinoferrocene palladium dichloride, put it into the above-mentioned single-necked flask, and let it pass nitrogen for half an hour. Continue heating to reflux in a nitrogen atmosphere overnight, cool the reaction system, pour the reaction solution into a beaker containing 500 mL of water, and extract with dichloromethane. The organic phase was collected and dried, mixed with silica gel, and sampled by dry method, and purified by column using dichloromethane/methanol (volume ratio of 10:1) as a developing solvent to obtain the intermediate tetrakis (pinacol borate) tetraphenyl Ethylene, 85% yield.		85%
With dichloro(1,1′-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 110℃; for 72h; Inert atmosphere;83%

Safety and Hazards

GHS Hazard StatementsNot Classified

Other Data

TransportationUnder the room temperature and away from light
HS Code
StorageUnder the room temperature and away from light
Shelf Life1 year
Market Price
Druglikeness
Lipinski rules component
分子量836.297
logP-14.8
HBA8
HBD0
Matching Lipinski Rules2
Veber rules component
Polar Surface Area (PSA)73.84
Rotatable Bond (RotB)8
Matching Veber Rules2
Use Pattern
1,1,2,2-Tetrakis(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethene has important applications in the field of materials science. It serves as a starting material for the synthesis of organic semiconductor materials, fluorescent materials, and light-emitting diode materials. By modifying and functionalizing its structure, the optical, electronic, and conductivity properties of materials can be controlled, enabling their use in optoelectronic devices, light sensors, organic solar cells, and other fields.

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