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Published TCIMAIL newest issue No.198
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CAS RN: 73183-34-3 | Product Number: B1964
Bis(pinacolato)diboron
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Purity: >99.0%(GC)
Synonyms:
- 4,4,4',4',5,5,5',5'-Octamethyl-2,2'-bi-1,3,2-dioxaborolane
Product Documents:
| Size | Unit Price | Belgium | Japan* | Quantity |
|---|---|---|---|---|
| 1G |
€16.00
|
Contact Us | 16 |
|
| 5G |
€37.00
|
Contact Us | ≥100 |
|
| 25G |
€120.00
|
13 | ≥100 |
|
| 100G |
€352.00
|
Contact Us | ≥100 |
|
*Stock available in Belgium will be delivered in 1 to 3 days
*Stock available in Japan will be delivered in 1 to 2 weeks (excludes regulated items and dry ice shipments).
| Product Number | B1964 |
Purity / Analysis Method 
|
>99.0%(GC) |
| Molecular Formula / Molecular Weight | C__1__2H__2__4B__2O__4 = 253.94 |
| Physical State (20 deg.C) | Solid |
| Storage Temperature
|
Refrigerated (0-10°C) |
| Store Under Inert Gas | Store under inert gas |
| Condition to Avoid | Moisture Sensitive,Heat Sensitive |
| CAS RN | 73183-34-3 |
| Reaxys Registry Number | 7703552 |
| PubChem Substance ID | 87564847 |
| Merck Index (14) | 1300 |
| MDL Number | MFCD00799570 |
Specifications
| Appearance | White to Almost white powder to crystal |
| Purity(GC) | min. 99.0 % |
| Melting point | 135.0 to 142.0 °C |
| Solubility in Methanol | almost transparency |
Properties (reference)
| Melting Point | 138 °C |
| Solubility (soluble in) | Ethanol, Benzene, Methanol |
GHS
| Pictogram |
|
| Signal Word | Warning |
| Hazard Statements | H302 + H312 + H332 : Harmful if swallowed, in contact with skin or if inhaled. H315 : Causes skin irritation. H319 : Causes serious eye irritation. |
| Precautionary Statements | P261 : Avoid breathing dust. P264 : Wash skin thoroughly after handling. P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection/ hearing protection. P337 + P313 : If eye irritation persists: Get medical advice/ attention. P302 + P352 + P312 : IF ON SKIN: Wash with plenty of water. Call a POISON CENTER/doctor if you feel unwell. P304 + P340 + P312 : IF INHALED: Remove person to fresh air and keep comfortable for breathing. Call a POISON CENTER/doctor if you feel unwell. |
Related Laws:
Transport Information:
| HS Number | 2920907080 |
Application
TCI Practical Example: Diborylation of Alkynes with a Platinum Catalyst
Used Chemicals
Procedure
To a degassed solution of diphenylacetylene (100 mg, 0.561 mmol) and bis(pinacolato)diboron (144 mg, 0.567 mmol) in DMF (0.5 mL) and toluene (0.5 mL) was added Pt(PPh3)4 (2 mg, 0.25 mol%). The reaction mixture was heated to 80 °C for 24 hours. After this time, the reaction was diluted with toluene (10 mL) and washed with saturated aqueous NH4Cl (2 x 10 mL). The organic phase was dried over MgSO4 and concentrated under reduced pressure. Recrystallization from MeOH afforded 1 as a white solid (241 mg, 0.558 mmol, 99%).
Experimenter’s Comments
The reaction mixture was monitored by TLC (CH2Cl2:hexane = 2:1, Rf = 0.45).
Analytical Data（Compound 1）
1H NMR (400 MHz, CDCl3); δ 7.02-7.09 (m, 6H), 6.94-6.96 (m, 4H), 1.32 (s, 24H).
13C NMR (101 MHz, CDCl3); δ 141.3, 129.3, 127.4, 125.8, 84.1, 24.9.
Lead Reference
- Platinum(0)-catalyzed diboration of alkynes
Other References
- Divergent and Stereoselective Synthesis of Tetraarylethylenes from Vinylboronates
Application
TCI Practical Example: Miyaura-Ishiyama Borylation using Pd(OAc)2
Used Chemicals
Procedure
To the solution of 3-iodobenzalehyde (1.16 g, 5.00 mmol) in dry DMF (15.0 mL) were added potassium acetate (981 mg, 10.0 mmol), palladium(II) acetate (112 mg, 0.500 mmol, 10 mol%) and bis(pinacolato)diborane (1.27 g, 5.00 mmol). The reaction mixture was stirred at 80 ºC for 7 h. The reaction mixture was cooled to room temperature and quenched with H2O (15 mL) and saturated NH4Cl aq. (10 mL), then the mixture was extracted twice with hexane : EtOAc = 4 : 1. The combined organic layer was washed with H2O (50 mL) and brine (50 mL), dried over Na2SO4, and concentrated under reduced pressure to afford the crude product as a yellow oil. The crude product was purified by column chromatography on silica-gel (hexane → hexane : EtOAc = 1:1) to afford 3-formylphenylboronic acid pinacol ester as a yellow oil (500 mg, 2.15 mmol, 43%).
Experimenter's Comments
(1) DMF was dried over molecular sieves.
(2) Completion of the reaction was confirmed by TLC (hexane : EtOAc = 1 : 1, Rf = 0.30) and GC.
Analytical Data（3-Formylphenylboronic Acid Pinacol Ester）
1H NMR (400 MHz, CDCl3); δ 10.1 (s, 1H), 8.30 (s, 1H), 8.06 (d, J = 4.0 Hz, 1H), 7.99 (ddd, J = 1.6, 1.8, 7.8 Hz, 1H), 7.53 (t, J = 8.0 Hz, 1H), 1.37 (s, 12H).
Lead Reference
- The bulky side chain of antillatoxin is important for potent toxicity: rational design of photoresponsive cytotoxins based on SAR studies
Application
Ni/Cu-Catalyzed Defluoroborylation of Fluoroarenes
Typical procedure (R = 4-Ph):
To a solution of 4-fluorobiphenyl (34.0 mg, 0.2 mmol, 1 eq.), bis(pinacolato)diboron (102 mg, 0.402 mmol, 2.0 eq.), copper iodide (7.6 mg, 0.04 mmol, 0.20 eq.), and cesium fluoride (91.0 mg, 0.6 mmol, 3.0 eq.) in toluene (0.5 mL) is added a solution of bis(1,5-cyclooctadiene)nickel(0) (5.1 mg, 0.02 mmol, 0.10 eq.) and tricyclohexylphosphine (28 mg, 99.8 µmol, 0.50 eq.) in toluene (0.5 mL) at room temperature. After stirring for 1 min at the same temperature, the mixture is heated at 80 °C with stirring for 20 h. After cooling to room temperature, saturated aqueous ammonium chloride (ca. 3 mL) is added to the mixture followed by extraction with EtOAc (ca. 3 mL × 3). The combined organic extract is dried over Na2SO4, and the filtrate is concentrated under reduced pressure. The residue is purified by preparative TLC (solvent: benzene/acetic acid = 20/1) to give 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl (55.6 mg, 0.198 mmol, 99% yield) as a colorless solid.
To a solution of 4-fluorobiphenyl (34.0 mg, 0.2 mmol, 1 eq.), bis(pinacolato)diboron (102 mg, 0.402 mmol, 2.0 eq.), copper iodide (7.6 mg, 0.04 mmol, 0.20 eq.), and cesium fluoride (91.0 mg, 0.6 mmol, 3.0 eq.) in toluene (0.5 mL) is added a solution of bis(1,5-cyclooctadiene)nickel(0) (5.1 mg, 0.02 mmol, 0.10 eq.) and tricyclohexylphosphine (28 mg, 99.8 µmol, 0.50 eq.) in toluene (0.5 mL) at room temperature. After stirring for 1 min at the same temperature, the mixture is heated at 80 °C with stirring for 20 h. After cooling to room temperature, saturated aqueous ammonium chloride (ca. 3 mL) is added to the mixture followed by extraction with EtOAc (ca. 3 mL × 3). The combined organic extract is dried over Na2SO4, and the filtrate is concentrated under reduced pressure. The residue is purified by preparative TLC (solvent: benzene/acetic acid = 20/1) to give 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl (55.6 mg, 0.198 mmol, 99% yield) as a colorless solid.
References
Application
C-H Borylation of Arenes
Typical Procedure:
A 25 mL-flask assembled a magnetic stirring bar, a septum inlet, and a condenser is charged with chloro(1,5-cyclooctadiene)iridium(I) dimer (10.1 mg, 0.015 mmol), 2,2’-bipyridyl (4.7 mg, 0.03 mmol), and bis-(pinacolato)diboron (254.0 mg, 1.0 mmol) and then flushed with nitrogen. An arene (60 mmol) is added, and the mixture is stirred at 80 °C for 16 h. The reaction mixture is analyzed by GC and GC mass spectroscopy. The product is extracted with benzene, washed with brine, and dried over MgSO4. Kugelrohr distillation gives analytically pure samples.
A 25 mL-flask assembled a magnetic stirring bar, a septum inlet, and a condenser is charged with chloro(1,5-cyclooctadiene)iridium(I) dimer (10.1 mg, 0.015 mmol), 2,2’-bipyridyl (4.7 mg, 0.03 mmol), and bis-(pinacolato)diboron (254.0 mg, 1.0 mmol) and then flushed with nitrogen. An arene (60 mmol) is added, and the mixture is stirred at 80 °C for 16 h. The reaction mixture is analyzed by GC and GC mass spectroscopy. The product is extracted with benzene, washed with brine, and dried over MgSO4. Kugelrohr distillation gives analytically pure samples.
References
- Mild iridium-catalyzed borylation of arenes. High turnover numbers, room temperature reactions, and isolation of a potential intermediate
Application
Diastereoselective Synthesis of Homoallyic Alcohols by Diboron-Promoted Coupling of Dienes and Aldehydes
References
- Diastereoselective Construction of Functionalized Homoallylic Alcohols by Ni-Catalyzed Diboron-Promoted Coupling of Dienes and Aldehydes
PubMed Literature
Product Articles
[TCIMAIL No.101] for Suzuki Cross-Coupling Reaction[Research Articles] Ni/Cu-Catalyzed Defluoroborylation of Fluoroarenes
Product Documents (Note: Some products will not have analytical charts available.)
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