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Cas Database

73183-34-3

73183-34-3

Identification

  • Product Name:Bis(pinacolato)diboron

  • CAS Number: 73183-34-3

  • EINECS:-0

  • Molecular Weight:253.942

  • Molecular Formula: C12H24B2O4

  • HS Code:29349990

  • Mol File:73183-34-3.mol

Synonyms:Bis(pinacolato)diborane;4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane;Pinacol diborane;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn, IrritantXi

  • Hazard Codes:Xi,Xn

  • Signal Word:No signal word.

  • Hazard Statement:none

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:TRC
  • Product Description:Bis(pinacolato)diboron
  • Packaging:100g
  • Price:$ 275
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Bis(pinacolato)diboron >99.0%(GC)
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Bis(pinacolato)diboron >99.0%(GC)
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Bis(pinacolato)diboron >99.0%(GC)
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Bis(pinacolato)diboron >99.0%(GC)
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  • Manufacture/Brand:Synthonix
  • Product Description:Bis(pinacolato)diboron 99+%
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  • Manufacture/Brand:Synthonix
  • Product Description:Bis(pinacolato)diboron 99+%
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:Bis(pinacolato)diboron
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  • Manufacture/Brand:Biosynth Carbosynth
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  • Manufacture/Brand:Biosynth Carbosynth
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Relevant articles and documentsAll total 34 Articles be found

The complex reactivity of β-diketiminato magnesium(i) dimers towards pinacolborane: Implications for catalysis

Jones, Dafydd D. L.,Matthews, Aidan J. R.,Jones, Cameron

, p. 5785 - 5792 (2019)

Reactions between the borane, HBpin (pin = pinacolato), and three magnesium(i) dimers, [{(ArNacnac)Mg-}2] (ArNacnac = [(ArNCMe)2CH]-; Ar = xylyl (Xyl), mesityl (Mes) or 2,6-diethylphenyl (Dep)), have been carried out in 2:1, 5:1 and 20:1 ratios. In all cases, NMR spectroscopic studies have revealed complex mixtures of many known and novel products from these reactions. From extracts of the crude reaction mixtures, low yields of ten compounds, representing six different types of complexes between β-diketiminato magnesium fragments and boron containing ligands, have been isolated and crystallographically characterised. These include unprecedented examples of compounds in which the γ-carbon of the β-diketiminate ligand has been activated by boron hydride fragments. In addition, boryloxide (OBpin), borate ([B(pin)2]- or [(pin)BH2]-), B-O bond ruptured [pinBH2]-, a diborane(5) dianion, or BH3 have been shown to be incorporated into the isolated complexes. The complexity of the products of the reported reactions are discussed in light of recently published patents and papers which report that magnesium(i) dimers act as efficient catalysts, or as pre-catalysts to well defined catalysts, for the hydroboration of a variety of unsaturated substrates by HBpin. Our results strongly suggest that magnesium(i) dimers are not catalysts in these reactions, and that there are many more potential (pre-)catalysts that are generated in these reactions, than have previously been reported.

Hydroborative reduction of amides to amines mediated by La(CH2C6H4NMe2-: O)3

Gong, Mingliang,Guo, Chenjun,Luo, Yunjie,Xie, Hongzhen,Zhang, Fangcao

, p. 779 - 791 (2022/01/22)

The deoxygenative reduction of amides to amines is a great challenge for resonance-stabilized carboxamide moieties, although this synthetic strategy is an attractive approach to access the corresponding amines. La(CH2C6H4NMe2-o)3, a simple and easily accessible lanthanide complex, was found to be highly efficient not only for secondary and tertiary amide reduction, but also for the most challenging primary reduction with pinacolborane. This protocol exhibited good tolerance for many functional groups and heteroatoms, and could be applied to gram-scale synthesis. The active species in this catalytic cycle was likely a lanthanide hydride.

Selective electrocatalytic hydroboration of aryl alkenes

Zhang, Yahui,Zhao, Xiangyu,Bi, Ce,Lu, Wenqi,Song, Mengyuan,Wang, Dongdong,Qing, Guangyan

, p. 1691 - 1699 (2021/03/09)

Organoboron compounds are powerful precursors of value-added organic compounds in synthetic chemistry, and transition metal-catalysed borylation has always been dominant. To avoid toxic reagents and costs associated with metal catalysts, simpler, more eco

Hydroboration of terminal olefins with pinacolborane catalyzed by new 2-iminopyrrolyl iron(ii) complexes

Cruz, Tiago F. C.,Pereira, Laura C. J.,Waerenborgh, Jo?o C.,Veiros, Luís F.,Gomes, Pedro T.

, p. 3347 - 3360 (2019/07/10)

Four paramagnetic 14-electron tetracoordinated Fe(ii) complexes of 5-substituted-2-iminopyrrolyl ligands of the type [Fe{κ2N,N′-5-R-NC4H2-2-C(H)N(2,6-iPr2-C6H3)}(Py)Cl], with R = 2,6-Me2-C6H3 (1a), 2,4,6-iPr3-C6H2 (1b), 2,4,6-Ph3-C6H3 (1c) and CPh3 (1d), were synthesized in moderate yields by reacting the respective 5-substituted-2-iminopyrrolyl potassium salts KLa-d with FeCl2(Py)4 in toluene. Complexes 1a-d were characterized by 1H NMR, FTIR spectroscopies, elemental analysis and by the Evans method, the corresponding effective magnetic moments showing a high-spin electronic nature. X-ray diffraction studies on complexes 1a and 1c showed distorted tetrahedral coordination geometries. Complexes 1a-c, activated with K(HBEt3), were efficient catalyst systems for the hydroboration of several terminal alkenes with pinacolborane in good to high yields (50-90%). This system mainly yielded the respective anti-Markovnikov addition products, except when styrenes were used. A screening of the hydroboration of styrene catalyzed by complexes 1a-c activated with K(HBEt3) showed that the selectivity in the Markovnikov product increased with increasing steric bulkiness of the R group, exhibiting selectivities up to 91%. Additionally, the stoichiometric reaction of complex 1b with K(HBEt3) over 30 minutes yielded the mixture of hydride species 2 and 22 (mixture I). On the other hand, when reacting the same components over 16 h, the Fe(i) complex 3 was also identified in the mixture, in addition to 2 + 22 (mixture II). These mixtures were characterized in solution by the Evans method and in the solid state by elemental analysis, 57Fe M?ssbauer and FTIR spectroscopies, compounds 22 and 3 being also analyzed by X-ray diffraction. These results suggest that the corresponding catalytic cycle follows the borane oxidative addition route to a Fe(i) species.

Deoxygenative Borylation of Secondary and Tertiary Alcohols

Friese, Florian W.,Studer, Armido

supporting information, p. 9561 - 9564 (2019/06/21)

Two different approaches for the deoxygenative radical borylation of secondary and tertiary alcohols are presented. These transformations either proceed through a metal-free silyl-radical-mediated pathway or utilize visible-light photoredox catalysis. Readily available xanthates or methyl oxalates are used as radical precursors. The reactions show broad substrate scope and high functional-group tolerance, and are conducted under mild and practical conditions.

Process route upstream and downstream products

Process route

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

ethylbenzene
100-41-4,27536-89-6

ethylbenzene

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

4,4,5,5-tetramethyl-2-phenethyl-1,3,2-dioxaborolane
165904-22-3

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

Conditions
Conditions Yield
With tetrabutylammonium tetrafluoroborate; In tetrahydrofuran; acetonitrile; at 20 ℃; for 3h; Inert atmosphere; Schlenk technique; Glovebox; Electrochemical reaction;
31 %Chromat.
30 %Chromat.
7 %Chromat.
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

ethylbenzene
100-41-4,27536-89-6

ethylbenzene

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

4,4,5,5-tetramethyl-2-(1-phenyl-ethyl)-[1,3,2]dioxaborolane
174090-36-9

4,4,5,5-tetramethyl-2-(1-phenyl-ethyl)-[1,3,2]dioxaborolane

4,4,5,5-tetramethyl-2-phenethyl-1,3,2-dioxaborolane
165904-22-3

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

Conditions
Conditions Yield
With tetrabutylammonium tetrafluoroborate; In tetrahydrofuran; acetonitrile; at 40 ℃; for 3h; Inert atmosphere; Schlenk technique; Glovebox; Electrochemical reaction;
42 %Chromat.
8 %Chromat.
22 %Chromat.
10 %Chromat.
2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

para-chlorobenzoic acid
74-11-3

para-chlorobenzoic acid

pinacolboronic acid
25240-59-9

pinacolboronic acid

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

biphenyl-4-carboxylic acid
92-92-2

biphenyl-4-carboxylic acid

Conditions
Conditions Yield
With water; In water-d2; at 27 ℃; for 24h; Inert atmosphere;
50%
49%
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
Conditions Yield
trans-chloro(dinitrogen)bis(tri-isopropylphosphine)rhodium(I); In benzene; 1 M or 1/3 M soln. heated at 140°C for 58 h; various condns. various yield;
20%
7%
C<sub>18</sub>H<sub>29</sub>B<sub>2</sub>O<sub>4</sub><sup>(1-)</sup>*Li<sup>(1+)</sup>*0.125C<sub>12</sub>H<sub>24</sub>B<sub>2</sub>O<sub>4</sub>

C18H29B2O4(1-)*Li(1+)*0.125C12H24B2O4

tris(pentafluorophenyl)borate
1109-15-5

tris(pentafluorophenyl)borate

Li[(hydride)B(pentafluorophenyl)3]

Li[(hydride)B(pentafluorophenyl)3]

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
Conditions Yield
With hydrogen; at 20 ℃; for 12h; under 3000.3 Torr;
73%
52%
71%
ethene
74-85-1

ethene

C<sub>18</sub>H<sub>29</sub>B<sub>2</sub>O<sub>4</sub><sup>(1-)</sup>*Li<sup>(1+)</sup>*0.125C<sub>12</sub>H<sub>24</sub>B<sub>2</sub>O<sub>4</sub>

C18H29B2O4(1-)*Li(1+)*0.125C12H24B2O4

tris(pentafluorophenyl)borate
1109-15-5

tris(pentafluorophenyl)borate

C<sub>26</sub>H<sub>16</sub>B<sub>2</sub>F<sub>15</sub>O<sub>2</sub><sup>(1-)</sup>*Li<sup>(1+)</sup>

C26H16B2F15O2(1-)*Li(1+)

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
Conditions Yield
at 20 ℃; for 12h; under 45004.5 Torr;
64%
C<sub>18</sub>H<sub>29</sub>B<sub>2</sub>O<sub>4</sub><sup>(1-)</sup>*Li<sup>(1+)</sup>*0.125C<sub>12</sub>H<sub>24</sub>B<sub>2</sub>O<sub>4</sub>

C18H29B2O4(1-)*Li(1+)*0.125C12H24B2O4

tris(pentafluorophenyl)borate
1109-15-5

tris(pentafluorophenyl)borate

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

Li[(hydride)B(pentafluorophenyl)3]

Li[(hydride)B(pentafluorophenyl)3]

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole
24388-23-6

2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
Conditions Yield
at 20 ℃; for 12h;
73%
41%
80%
dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane
185990-03-8

dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane

dimethyl(phenyl)((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxy)silane
1349697-23-9

dimethyl(phenyl)((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxy)silane

dimethylphenylsilanol
5272-18-4

dimethylphenylsilanol

1,1,3,3-tetramethyl-1,3-diphenyldisiloxane
56-33-7

1,1,3,3-tetramethyl-1,3-diphenyldisiloxane

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
Conditions Yield
With Au-TiO2; In dichloromethane; at 25 ℃; for 2h;
2,3-dimethyl-2,3-butane diol
76-09-5

2,3-dimethyl-2,3-butane diol

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
Conditions Yield
With tetrakis(dimethylamido)diborane; In diethyl ether; at 20 ℃; for 18h; Conversion of starting material;
100%
With tetrakis(dimethylamido)diborane; at 50 - 100 ℃; for 0.616667h; Conversion of starting material;
94.2%
With tetrakis(dimethylamido)diborane; In n-heptane; at 40 - 98 ℃; for 0.6h; Conversion of starting material;
90.5%
With tetrakis(dimethylamido)diborane; In 1,4-dioxane; at 40 - 100 ℃; for 0.683333h; Conversion of starting material;
90%
With tetrakis(dimethylamido)diborane; In dichloromethane; at 20 ℃; for 18h; Conversion of starting material;
87.5%
With tetrakis(dimethylamido)diborane; In toluene; at 20 - 105 ℃; for 1h;
84%
With tetrakis(tetrahydropyrrole)boron;
83%
With tetrakis(dimethylamido)diborane; In dimethyl sulfoxide; at 80 - 110 ℃; for 18.2h; Conversion of starting material;
57.8%
With tetrakis(dimethylamido)diborane; In acetic acid butyl ester; at 80 - 110 ℃; for 18.2h; Conversion of starting material;
49.9%
Multi-step reaction with 2 steps
1: 2,6-di-tert-butyl-4-methyl-phenol / dichloromethane / -10 - 0 °C / Inert atmosphere
2: C25H36FeN2Si / 10 h / Inert atmosphere; Reflux
With 2,6-di-tert-butyl-4-methyl-phenol; C25H36FeN2Si; In dichloromethane;
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

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

bis(pinacol)diborane
73183-34-3

bis(pinacol)diborane

Conditions
Conditions Yield
With C25H36FeN2Si; for 10h; Inert atmosphere; Reflux;
62%
With C3H10B(1-)*K(1+); In neat (no solvent); at 25 ℃; for 16h; Inert atmosphere; Schlenk technique;
44%
With platinum on aluminium oxide; for 48h; Heating;
With catalyst: Rh or Pd or Pt on alumina; In not given; Soxlet reactor, HBPin distilled in presence of catalyst: Rh/alumina for 20 h or Pd/alumina for 40 h or Pt/alumina for 20 h;
With carbonylhydrido[6-(di-tert-butylphosphinomethylene)-2-(N,N-diethylaminomethyl)-1,6-dihydropyridine]ruthenium(II); In tetrahydrofuran; 1,4-dioxane; for 18h; Reflux;
10 %Chromat.

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