CAS RN: 1295-35-8 | Product Number: B3095
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|Purity / Analysis Method||>97.0%(T)|
|Molecular Formula / Molecular Weight||C__1__6H__2__4Ni = 275.06|
|Physical State (20 deg.C)||Solid|
|Store Under Inert Gas||Store under inert gas|
|Condition to Avoid||Light Sensitive,Air Sensitive,Heat Sensitive|
|Packaging and Container||5G-Ampules (View image)|
|Reaxys Registry Number||11341079|
|PubChem Substance ID||354333940|
|Appearance||Light yellow to Brown powder to crystal|
|Purity(Chelometric Titration)||min. 97.0 %|
|Melting Point||60 °C(dec.)|
|Hazard Statements||H372 : Causes damage to organs through prolonged or repeated exposure.
H317 : May cause an allergic skin reaction.
H334 : May cause allergy or asthma symptoms or breathing difficulties if inhaled.
H350 : May cause cancer.
H228 : Flammable solid.
|Precautionary Statements||P260 : Do not breathe dust/ fume/ gas/ mist/ vapours/ spray.
P210 : Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking.
P201 : Obtain special instructions before use.
P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection.
P370 + P378 : In case of fire: Use dry sand, dry chemical or alcohol-resistant foam to extinguish.
P308 + P313 : IF exposed or concerned: Get medical advice/ attention.
P304 + P340 : IF INHALED: Remove person to fresh air and keep comfortable for breathing.
Conversion of Amides to Esters by the Nickel-catalysed Activation of Amide C–N Bonds
A Two-step Approach to Achieve Secondary Amide Transamidation Enabled by Nickel Catalysis
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.
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