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173603-23-1

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Basic Information
CAS No.: 173603-23-1
Name: CIS-1,2-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STILBENE
Article Data: 16
Molecular Structure:
Molecular Structure of 173603-23-1 (CIS-1,2-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STILBENE)
Formula: C20H30B2O4
Molecular Weight: 356.078
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;
Density: 1.03 g/cm3
Melting Point: 69-73 °C(lit.)
Boiling Point: 363.9 °C at 760 mmHg
Flash Point: 173.9 °C
Safety: 24/25
PSA: 36.92000
LogP: 4.33280
Related products
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With palladium diacetate; triphenylphosphine; p-benzoquinone at 20℃; under 760.051 Torr; for 24h;93%
...Expand
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Specification

The 1,3,2-Dioxaborolane,2,2'-[(1E)-1-phenyl-1,2-ethenediyl]bis[4,4,5,5-tetramethyl-, with the CAS registry number 173603-23-1, has the systematic name of 2,2'-[(E)-1-phenylethene-1,2-diyl]bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane). And the molecular formula of the chemical is C20H30B2O4. What's more, while dealing with this chemical, you should avoid contacting with skin and eyes.

The characteristics of 1,3,2-Dioxaborolane,2,2'-[(1E)-1-phenyl-1,2-ethenediyl]bis[4,4,5,5-tetramethyl- are as followings: (1)#H bond acceptors: 4; (2)#H bond donors: 0; (3)#Freely Rotating Bonds: 3; (4)Polar Surface Area: 36.92 Å2; (5)Index of Refraction: 1.498; (6)Molar Refractivity: 101.11 cm3; (7)Molar Volume: 344.6 cm3; (8)Polarizability: 40.08×10-24cm3; (9)Surface Tension: 32.7 dyne/cm; (10)Density: 1.03 g/cm3; (11)Flash Point: 173.9 °C; (12)Enthalpy of Vaporization: 58.6 kJ/mol; (13)Boiling Point: 363.9 °C at 760 mmHg; (14)Vapour Pressure: 3.65E-05 mmHg at 25°C. 

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: O1B(OC(C)(C)C1(C)C)/C(c2ccccc2)=C\B3OC(C)(C)C(O3)(C)C
(2)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-
(3)InChIKey: VQWACXAYGMFHOQ-PEZBUJJGBX