173603-23-1

Basic information

• Product Name: CIS-1,2-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STILBENE
• Synonyms: (E)-STILBENEDIBORONIC ACID BIS(PINACOL) ESTER;(E)-ALPHA,BETA-STYRENEDIBORONIC ACID BIS(PINACOL) ESTER;CIS-1,2-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STILBENE;CIS-1,2-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STYRENE;CIS-2-PHENYLVINYL-1,2-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE);(E)-Phenyl-1,2-ethylenediboronic acid bis(pinacol) ester, 98%;(E)-alpha,beta-Styrenediboronicacid;(e)-à,á-styrenediboronic acid bis(pinacol) ester
• CAS NO: 173603-23-1
• Molecular Formula: C₂₀H₃₀B₂O₄
• Molecular Weight: 356.07
• Product Categories: Alkenyl Boronate Esters;Boronate Esters;Boronic Acids and Derivatives;Chemical Synthesis;Organometallic Reagents
• Mol File: 173603-23-1.mol
• Article Data: 16

Chemical Properties

• Melting Point: 69-73 °C(lit.)
• Boiling Point: 363.9 °C at 760 mmHg
• Flash Point: 173.9 °C
• Appearance: /
• Density: 1.03 g/cm³
• Vapor Pressure: 3.65E-05mmHg at 25°C
• Refractive Index: 1.498
• BRN: 8855562
• CAS DataBase Reference: CIS-1,2-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STILBENE(CAS DataBase Reference)
• NIST Chemistry Reference: CIS-1,2-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STILBENE(173603-23-1)
• EPA Substance Registry System: CIS-1,2-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STILBENE(173603-23-1)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 173603-23-1(Hazardous Substances Data)

Usage

General Description

CIS-1,2-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STILBENE is a chemical compound with the molecular formula C30H36B2O4. It is a boron-containing stilbene derivative that is used in various organic synthesis reactions. CIS-1,2-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STILBENE is known for its unique structure and is often used as a building block in the synthesis of advanced materials and pharmaceutical drugs. It has applications in the field of organic chemistry and material science, and its properties and reactivity make it a valuable tool for researchers and industrial chemists in the development of new compounds and materials.

InChI:InChI=1/C20H30B2O4/c1-17(2)18(3,4)24-21(23-17)14-16(15-12-10-9-11-13-15)22-25-19(5,6)20(7,8)26-22/h9-14H,1-8H3/b16-14-

Synthetic route

phenylacetylene (536-74-3) + bis(pinacol)diborane (73183-34-3) → (E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (173603-23-1)

Conditions	Yield
With gold In toluene at 100℃; for 1.5h; Catalytic behavior; Reagent/catalyst; Solvent; Time; Concentration; Green chemistry; diastereoselective reaction;	93%
With atomically dispersed Pt on beta-cyclodextrin-containing polymer In toluene at 100℃; for 2h; Reagent/catalyst; Temperature; Solvent;	93%
With Pd(1,3,4,5-tetramethylimidazol-2-ylidene)2(diphenylacetylene) In benzene at 20℃; for 3h; stereoselective reaction;	91%

bis(pinacol)diborane (73183-34-3) + 4,4,5,5-tetramethyl-2-phenylethynyl-[1,3,2]dioxaborolane (159087-45-3) → (E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (173603-23-1) + 2,2',2''-(2-phenylethene-1,1,2-triyl)tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Conditions	Yield
tetrakis(triphenylphosphine)platinum In toluene (N2); addn. of phenylethynylpinacolatoborane in react. mixt. of Pt(PPh3)4 and bis(pinacolato)diborane(4) in dry toluene; stirring overnight at 80°C;	A n/a B 0%

phenylacetylene (536-74-3) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-((E)-styryl)-[1,3,2]dioxaborolane (83947-56-2) + (E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (173603-23-1)

Conditions	Yield
With triphenylphosphine In toluene at 160℃; under 1125.11 Torr; for 1.5h; Inert atmosphere; stereoselective reaction;
With Pt(075 wtpercent)/CeO2 In toluene at 160℃; under 1125.11 Torr; for 0.7h; Inert atmosphere; stereoselective reaction;

phenylacetylene (536-74-3) → (E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (173603-23-1) + 2,2',2''-(2-phenylethene-1,1,2-triyl)tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Conditions	Yield
Multi-step reaction with 2 steps 1: HCl; (n-C4H9)Li / hexane; diethyl ether 2: tetrakis(triphenylphosphine)platinum / toluene View Scheme

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) → (E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (173603-23-1) + 2,2',2''-(2-phenylethene-1,1,2-triyl)tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Conditions	Yield
Multi-step reaction with 2 steps 1: HCl; (n-C4H9)Li / hexane; diethyl ether 2: tetrakis(triphenylphosphine)platinum / toluene View Scheme

phenylacetylene (536-74-3) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 4,4,5,5-tetramethyl-2-(1-phenylvinyl)-1,3,2-dioxaborolane (143825-84-7) + 4,4,5,5-tetramethyl-2-styryl-[1,3,2]dioxaborolane (78782-27-1) + (E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (173603-23-1)

Conditions	Yield
With bis(1,5-cyclooctadiene)diiridium(I) dichloride; tert-butylisonitrile; carbon monoxide at 50℃; under 760.051 Torr;	A 26 %Spectr. B 15 %Spectr. C 51 %Spectr.

iodobenzene (591-50-4) + (E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (173603-23-1) → Triphenylethylene (58-72-0)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium hydroxide In tetrahydrofuran; water at 70℃; for 4h; Suzuki-Miyaura Coupling;	100%

(E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (173603-23-1) → (E)-2-(2-bromo-1-phenylvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1610462-62-8)

Conditions	Yield
With copper(ll) bromide In tetrahydrofuran; water at 70℃; for 1h;	98%

(E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (173603-23-1) → (E)-2-(2-iodo-1-phenylvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1610462-60-6)

Conditions	Yield
With iodine; sodium hydroxide In diethyl ether at 0℃; for 0.5h;	95%

methanol (67-56-1) + carbon monoxide (201230-82-2) + (E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (173603-23-1) → dimethyl 2-(phenyl)maleate (29576-99-6)

Conditions	Yield
With palladium diacetate; triphenylphosphine; p-benzoquinone at 20℃; under 760.051 Torr; for 24h;	93%

(E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (173603-23-1) → (R)-1-phenyl-1,2-ethanediol (16355-00-3)

Conditions	Yield
Stage #1: (E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) With hydrogen; di(norbornadiene)rhodium(I) tetrafluoroborate; (R)-1-[2-(2'-diphenylphosphinophenyl)-ferrocenyl]ethyldi[bis-(3,5-trifluoromethyl)phenyl]phosphine under 11400.8 Torr; Stage #2: With dihydrogen peroxide Product distribution / selectivity;	86%
Stage #1: (E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) With hydrogen; di(norbornadiene)rhodium(I) tetrafluoroborate; (R)-1-[2-(2'-diphenylphosphinophenyl)-ferrocenyl]ethyldi[bis-(3,5-trifluoromethyl)phenyl]phosphine under 11400.8 Torr; Stage #2: With sodium hydroxide; dihydrogen peroxide Product distribution / selectivity;	86%

2-iodo-benzo[1,2-b:4,3-b']dithiophene (70218-28-9) + (E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (173603-23-1) → C28H16S4

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; toluene for 8h; Suzuki coupling reaction; Heating;	73%

(E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (173603-23-1) → (E)-2-(2-chloro-1-phenylvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1610462-61-7)

Conditions	Yield
With copper dichloride In tetrahydrofuran; water at 70℃; for 1h;	62%

para-bromotoluene (106-38-7) + (E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (173603-23-1) → (CH3)4C2O2BC(C6H5)CHC6H4CH3 (1214265-11-8)

Conditions	Yield
With K2CO3; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In dimethylformamide 80°C, 16 h;	53%

naphthalene-1,8-diamine (479-27-6) + (E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (173603-23-1) → (E)-2,2'-(1-phenylethene-1,2-diyl)bis(2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine)

Conditions	Yield
In toluene at 120℃; for 48h; Sealed tube;	11%

(E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (173603-23-1) → 2,2'-(1-phenylethane-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (189885-64-1)

Conditions	Yield
With bis(norbornadiene)rhodium(l)tetrafluoroborate; (R)-Walphos (W001); hydrogen In toluene under 15001.2 Torr; for 24h;
With hydrogen In toluene at 130℃; under 5250.53 Torr; for 13h;

(E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (173603-23-1) → 2-fluoroacetophenone (450-95-3) + 2,2-difluoro-1-phenylethanone (395-01-7)

Conditions	Yield
Stage #1: (E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) With sodium hydroxide; Selectfluor In acetonitrile at 25℃; for 15h; Stage #2: With sodium hydroxide In acetonitrile

cyclohexylamine (108-91-8) + (E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (173603-23-1) → C14H17F2N

Conditions	Yield
Stage #1: (E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) With sodium hydrogencarbonate; Selectfluor In acetonitrile at 20℃; for 15h; Stage #2: cyclohexylamine With montmorillonite K-10 In acetonitrile at 25℃; for 15h; Further stages.;	19 % Spectr.

N-butylamine (109-73-9) + (E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (173603-23-1) → C12H15F2N

Conditions	Yield
Stage #1: (E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) With sodium hydrogencarbonate; Selectfluor In acetonitrile at 20℃; for 15h; Stage #2: N-butylamine With montmorillonite K-10 In acetonitrile at 25℃; for 15h; Further stages.;	33 % Spectr.

isopropylamine (75-31-0) + (E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (173603-23-1) → N-(2,2-difluoro-1-phenylethylidene)isopropylamine (914801-74-4) + 2,2-difluoro-1-phenylethanone (395-01-7)

Conditions	Yield
Stage #1: (E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) With sodium hydrogencarbonate; Selectfluor In acetonitrile at 20℃; for 15h; Stage #2: isopropylamine With montmorillonite K-10 In acetonitrile at 25℃; for 15h; Further stages.;	A 27 % Spectr. B 1 % Spectr.

(E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (173603-23-1) → (2R)-2,2'-(1-phenylethane-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (1198172-00-7)

Conditions	Yield
With C32H12BF24(1-)*C56H70IrNO7P(1+); hydrogen In dichloromethane at 20℃; under 37503.8 Torr; for 2h; optical yield given as %ee; enantioselective reaction;

(E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (173603-23-1) → (E)-1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-phenylethene (562098-10-6)

Conditions	Yield
With tris[2-phenylpyridinato-C2,N]iridium(III) In acetonitrile for 16h; Sealed tube; Inert atmosphere; UV-irradiation;

naphthalene-1,8-diamine (479-27-6) + (E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (173603-23-1) → C28H24B2N4

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene / 48 h / 120 °C / Sealed tube 2: 2-(2,6-iPr2−C6H3NCMe)-6-(C(Me)N-((S)-(CH(CH3)C(CH3)2CH2−))−(C5H3N)Co); hydrogen / benzene-d6 / 24 h / 23 °C / 3040.2 Torr / Sealed tube; Glovebox View Scheme

Upstream product

• 536-74-3 phenylacetylene 
• 73183-34-3 bis(pinacol)diborane 
• 159087-45-3 4,4,5,5-tetramethyl-2-phenylethynyl-[1,3,2]dioxaborolane 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 

Downstream Products

• 450-95-3 2-fluoroacetophenone 
• 395-01-7 2,2-difluoro-1-phenylethanone 
• 914801-74-4 N-(2,2-difluoro-1-phenylethylidene)isopropylamine 
• 16355-00-3 (R)-1-phenyl-1,2-ethanediol 
• 1214265-11-8 (CH₃)4C₂O₂BC(C₆H₅)CHC₆H₄CH₃ 
• 29576-99-6 dimethyl 2-(phenyl)maleate 
• 1198172-00-7 (2R)-2,2'-(1-phenylethane-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 
• 1610462-60-6 (E)-2-(2-iodo-1-phenylvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1610462-61-7 (E)-2-(2-chloro-1-phenylvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1610462-62-8 (E)-2-(2-bromo-1-phenylvinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 58-72-0 Triphenylethylene 
• 562098-10-6 (E)-1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-phenylethene 

Relevant articles and documents

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