• Name

  CIS-1,2-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STILBENE

• EINECS
• CAS No. 173603-23-1
• Article Data16
• CAS DataBase
• Density 1.03 g/cm³
• Solubility
• Melting Point 69-73 °C(lit.)
• Formula C₂₀H₃₀B₂O₄
• Boiling Point 363.9 °C at 760 mmHg
• Molecular Weight 356.078
• Flash Point 173.9 °C
• Transport Information
• Appearance
• Safety 24/25
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms 1,3,2-Dioxaborolane,2,2'-(1-phenyl-1,2-ethenediyl)bis[4,4,5,5-tetramethyl-, (E)-;2,2'-[(E)-1-phenylethene-1,2-diyl]bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane);(E)-Phenyl-1,2-ethylenediboronic acid bis(pinacol) ester;
• PSA 36.92000
• LogP 4.33280

Synthetic route

536-74-3

phenylacetylene

73183-34-3

bis(pinacol)diborane

173603-23-1

(E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Conditions

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%

73183-34-3

bis(pinacol)diborane

159087-45-3

4,4,5,5-tetramethyl-2-phenylethynyl-[1,3,2]dioxaborolane

A

173603-23-1

(E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

B

2,2',2''-(2-phenylethene-1,1,2-triyl)tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Conditions

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%

...Expand

536-74-3

phenylacetylene

73183-34-3

bis(pinacol)diborane

A

83947-56-2

4,4,5,5-tetramethyl-2-((E)-styryl)-[1,3,2]dioxaborolane

B

173603-23-1

(E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Conditions

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;

...Expand

536-74-3

phenylacetylene

A

173603-23-1

(E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

B

2,2',2''-(2-phenylethene-1,1,2-triyl)tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Conditions

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

61676-62-8

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

A

173603-23-1

(E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

B

2,2',2''-(2-phenylethene-1,1,2-triyl)tris(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Conditions

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

536-74-3

phenylacetylene

25015-63-8

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

A

143825-84-7

4,4,5,5-tetramethyl-2-(1-phenylvinyl)-1,3,2-dioxaborolane

B

78782-27-1

4,4,5,5-tetramethyl-2-styryl-[1,3,2]dioxaborolane

C

173603-23-1

(E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Conditions

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.

...Expand

591-50-4

iodobenzene

173603-23-1

(E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

58-72-0

Triphenylethylene

Conditions

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

173603-23-1

(E)-2,2′-(1-phenylethene-1,2-diyl)bis(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

Conditions

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

173603-23-1

(E)-2,2′-(1-phenylethene-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

Conditions

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

67-56-1

methanol

201230-82-2

carbon monoxide

173603-23-1

(E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

29576-99-6

dimethyl 2-(phenyl)maleate

Conditions

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

...Expand

173603-23-1

(E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

16355-00-3

(R)-1-phenyl-1,2-ethanediol

Conditions

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%

70218-28-9

2-iodo-benzo[1,2-b:4,3-b']dithiophene

173603-23-1

(E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

C28H16S4

Conditions

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

173603-23-1

(E)-2,2′-(1-phenylethene-1,2-diyl)bis(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

Conditions

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

106-38-7

para-bromotoluene

173603-23-1

(E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

1214265-11-8

(CH3)4C2O2BC(C6H5)CHC6H4CH3

Conditions

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

479-27-6

naphthalene-1,8-diamine

173603-23-1

(E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

(E)-2,2'-(1-phenylethene-1,2-diyl)bis(2,3-dihydro-1H-naphtho[1,8-de][1,3,2]diazaborinine)

Conditions

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

173603-23-1

(E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

189885-64-1

2,2'-(1-phenylethane-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Conditions

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;

173603-23-1

(E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

A

450-95-3

2-fluoroacetophenone

B

395-01-7

2,2-difluoro-1-phenylethanone

Conditions

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

108-91-8

cyclohexylamine

173603-23-1

(E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

C14H17F2N

Conditions

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.

109-73-9

N-butylamine

173603-23-1

(E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

C12H15F2N

Conditions

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.

75-31-0

isopropylamine

173603-23-1

(E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

A

914801-74-4

N-(2,2-difluoro-1-phenylethylidene)isopropylamine

B

395-01-7

2,2-difluoro-1-phenylethanone

Conditions

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.

...Expand

173603-23-1

(E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

1198172-00-7

(2R)-2,2'-(1-phenylethane-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

Conditions

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;

173603-23-1

(E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

562098-10-6

(E)-1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-phenylethene

Conditions

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

479-27-6

naphthalene-1,8-diamine

173603-23-1

(E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

C28H24B2N4

Conditions

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

1,3,2-Dioxaborolane,2,2'-[(1E)-1-phenyl-1,2-ethenediyl]bis[4,4,5,5-tetramethyl- Specification