562098-10-6

Basic information

• Product Name: 1,3,2-Dioxaborolane, 2,2'-[(1Z)-1-phenyl-1,2-ethenediyl]bis[4,4,5,5-tetramethyl-
• CAS NO: 562098-10-6
• Molecular Formula: C20H30B2O4
• Molecular Weight: 356.078
• Mol File: 562098-10-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1,3,2-Dioxaborolane, 2,2'-[(1Z)-1-phenyl-1,2-ethenediyl]bis[4,4,5,5-tetramethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,2-Dioxaborolane, 2,2'-[(1Z)-1-phenyl-1,2-ethenediyl]bis[4,4,5,5-tetramethyl-(562098-10-6)
• EPA Substance Registry System: 1,3,2-Dioxaborolane, 2,2'-[(1Z)-1-phenyl-1,2-ethenediyl]bis[4,4,5,5-tetramethyl-(562098-10-6)

Safety Data

• Hazardous Substances Data: 562098-10-6(Hazardous Substances Data)

Usage

Chemical structure

The compound has a boron atom and a phenyl group, with a 1,3,2-dioxaborolane ring and a 1,2-ethenediyl bridge connecting two 4,4,5,5-tetramethyl groups.

Use in organic synthesis

It is commonly used as a reagent in various chemical reactions, particularly in the synthesis of complex molecules.

Versatility

The compound is known for its ability to undergo reactions with a wide range of organic compounds, making it a valuable tool in organic chemistry.

Stability

It is known for its stability, which makes it suitable for use in laboratory settings.

Low toxicity

The compound is relatively low in toxicity, making it a popular choice for use in research and development.

Applications

It is used in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and materials.

Safety

As with any chemical compound, it is important to follow proper safety protocols when handling and using 1,3,2-Dioxaborolane, 2,2'-[(1Z)-1-phenyl-1,2-ethenediyl]bis[4,4,5,5-tetramethylto minimize the risk of exposure or harm.

Upstream product

• 536-74-3 phenylacetylene 
• 73183-34-3 bis(pinacol)diborane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 3240-11-7 Phenylacetylene-d1 
• 173603-23-1 (E)-2,2′-(1-phenylethene-1,2-diyl)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) 

Downstream Products

• 1519954-04-1 methyl 2-dibenzylamino-4-(4,4,4,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-phenylbut-3-enoate 
• 1519954-24-5 methyl 2-dibenzylamino-4-(4-nitrophenyl)-4-phenylbut-3-enoate 
• 1519954-21-2 methyl 4-(4-methylphenyl)-2-(morpholino)-4-phenylbut-3-enoate 

Relevant articles and documents

Hydroboration of Terminal Alkenes and trans-1,2-Diboration of Terminal Alkynes Catalyzed by a Manganese(I) Alkyl Complex

A MnI-catalyzed hydroboration of terminal alkenes and a 1,2-diboration of terminal alkynes with pinacolborane (HBPin) is described. For alkenes, anti-Markovnikov hydroboration takes place; for alkynes the reaction proceeds with excellent trans-1,2-selectivity. The most active pre-catalyst is bench-stable alkyl bisphosphine MnI complex fac-[Mn(dippe)(CO)3(CH2CH2CH3)]. The catalytic process is initiated by migratory insertion of a CO ligand into the Mn–alkyl bond to yield an acyl intermediate, which undergoes B?H bond cleavage of HBPin (for alkenes) and rapid C?H bond cleavage (for alkynes), forming the active MnI boryl and acetylide catalysts [Mn(dippe)(CO)2(BPin)] and [Mn(dippe)(CO)2(C≡CR)], respectively. A broad variety of aromatic and aliphatic alkenes and alkynes was efficiently and selectively borylated. Mechanistic insights are provided based on experimental data and DFT calculations revealing that an acceptorless reaction is operating involving dihydrogen release.

Regio- and stereocontrolled access to ?-boronated unsaturated amino esters and derivatives from (z)-alkenyl 1,2-bis(boronates)

The Borono-Mannich reaction of (Z)-1-alkene-1,2-diboronic esters proceeded regioselectively at the terminal C-B bond to afford (E)-?-boronated unsaturated amino esters in good yields. These compounds were then subjected to Suzuki couplings for the creatio

Synthesis and characterization of platinum(II)-Bis(boryl) catalyst precursors for diboration of alkynes and diynes: Molecular structures of cis-[(PPh3)2Pt(B-4-Butcat)2], cis-[(PPh3)2Pt(Bcat)2], cis-[(dppe)Pt(Bcat)2], cis-[(dppb)Pt(Bcat)2]

The reactions of the B-B-bonded compounds B2(cat)2 (cat = 1,2-O2C6H4) (1a), B2(4-But-cat)2 (1b), and B2(OCMe2CMe2O)2 (1c) with the Pt(0)-bis(phosphine) complex [(PPh3)2Pt(η-C2H4)] (4) via oxidative addition of the B-B bond yield cis-bis(boryl) Pt(II) complexes. The molecular structures of cis-[(PPh3)2Pt(Bcat)2]·C 6D6 (3a) and cis-[(PPh3)2Pt(B-4-Butcat)2] (3b) were determined by single-crystal X-ray diffraction. Reaction of 3a with 1 equiv of the bidentate phosphine dppe (Ph2PCH2CH2PPh2) or dppb (Ph2P(CH2)4PPh2) proceeds smoothly in toluene to give cis-[(dppe)Pt(Bcat)2] (5a) and cis-[(dppb)Pt(Bcat)2] (5b), respectively, which have also been characterized by X-ray diffraction. Compounds 3a,b and 4 are highly active catalyst precursors for the diboration of alkynes and 1,3-diynes. X-ray crystal structures of (E)-(4-MeOC6H4)C(Bcat)=CH(Bcat) (10c), (Z)-(C6H5)C(Bcat)=C(C6H5)(Bcat) (10e), and (Z,Z)-(4-MeOC6H4)C(Bcat)=C(Bcat)C(Bcat)=C(4-MeOC 6H4)(Bcat) (14a) confirm the cis stereochemistry of the boron substituents in three representative cases, namely, products of the catalyzed diboration of the terminal alkyne 4-MeOC6H4C=CH, the internal alkyne PhC=CPh, and the tetraboration of the diyne 4,4′-MeOC6H4C=CC=CC6H4OMe. The presence of the C=CSiMe3 moiety in catalytic reactions gives rise to additional products other than those derived from the diboration of the alkyne group. Metathetical reactions involving the diboron reagent and products derived from C-Si bond cleavage give rise to novel tris(boronate esters) as a result of the subsequent diboration of the C=CB(OR2) moieties formed by this competing process. The absence of catalytic activity using compound 5a, the extremely low activity of 5b, and the strong decrease in activity of 3b in the presence of added PPh3 suggests that phosphine dissociation is a critical step in the catalytic pathway.