67975-91-1

Usage

Type of Compound

Derivative of boronic acid

Composition

Consists of a boron atom, oxygen atoms, and a chlorine atom

Industrial Applications

Used in various industrial and research applications

Role in Organic Synthesis

Commonly used as a reagent, particularly in the formation of carbon-carbon and carbon-heteroatom bonds

Utilization in Production

Employed in the production of pharmaceuticals, agrochemicals, and advanced materials

Potential Applications

Fields of polymer science, catalysis, and material science due to its unique chemical properties

Safety Precaution

Should be handled with care, as it can be hazardous if not used properly

Upstream product

• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 71-43-2 benzene 
• 142-61-0 Hexanoyl chloride 
• 35718-08-2 propargyl chloroformate 
• 98-88-4 benzoyl chloride 

Downstream Products

• 458532-84-8 2-chloro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyridine 
• 781640-95-7 2,4,6-tris[bis(trimethylsilyl)methyl]phenyl(mesityl)chlorosilylpinacolborane 
• 1195-66-0 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1048692-97-2 2-cyclohexylamino-4,4,5,5-tetramethyl-1,3-dioxaborolane 
• 1130728-55-0 2,4-dimethyl-3,6-dioxocyclohexa-1,4-dienylboronic acid 
• 1130728-74-3 3,5-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohexa-2,5-diene-1,4-dione 
• 1130728-72-1 2-(3,6-dimethoxy-2,4-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Relevant academic research and scientific papers

The phosphinoboration of acyl chlorides

This investigation examines the reactivity of phosphinoboronate esters Ph2PBpin (pin = 1,2-O2C2Me4) and Ph2PBcat (cat = 1,2-O2C6H4), as well as other phosphinoboron species, with various aryl and aliphatic acyl chlorides. These reactions proceed smoothly to give acyl phosphines of the type RC(O)PR′2 along with loss of a boron-chloride compound. In some cases, a second equivalent of the phosphinoboron species can add to the CO double bond at elevated temperatures to give the corresponding diphosphines RC(OBR′′2)(PR′2)2. These ambiphilic diphosphines behave like substituted (1,1-bis(diphenylphosphino)methane) derivatives in a reaction of PhC(OBpin)(PPh2)2 (2a) with (η5-C9H7)Rh(η2-coe)2 (coe = cis-cyclooctene) affording the indenyl rhodium complex (η5-C9H7)Rh(PhC(OBpin)(PPh2)2) (3a) where the phosphines are bound to the metal centre in a κ2-P,P bidentate manner.

Cationic dihydride boryl and dihydride silyl osmium(IV) NHC complexes: A marked diagonal relationship

The complex [OsCl(η6-p-cymene)(IPr)]OTf (1; IPr = 1,3-bis(2,6-diisopropylphenyl)imidazolylidene, OTf = trifluoromethanesulfonate) reacts with pinacolborane (HBpin) and catecholborane (HBcat) to give the dihydride boryl osmium(IV) derivatives [OsH2(Bpin)(η6- p-cymene)(IPr)]OTf (2) and [OsH2(Bcat)(η6-p-cymene) (IPr)]OTf (3), which undergo hydrolysis to afford the trihydride [OsH 3(η6-p-cymene)(IPr)]OTf (4). In agreement with the boron-silicon diagonal relationship, complex 1 also reacts with silanes, HSiR3. The reactions lead to the dihydride silyl species [OsH 2(SiR3)(η6-p-cymene)(IPr)]OTf (SiR 3 = SiPh3 (5), SiEt3 (6), SiHPh2 (7)), which also undergo hydrolysis to yield 4. Complexes 2 and 5 have been characterized by X-ray diffraction analysis. Their four-legged piano-stool geometries with transoid hydride ligands are similar. In solution, the arene rotates over the remaining four ligands. The activation barrier of the process depends upon the size of the boryl or silyl groups. The nature of the Os-B and Os-Si interactions has been investigated by means of computational methods. Both of them are σ bonds with small or negligible π back-donation from the metal to the ligands.