454185-98-9

Basic information

• Product Name: (4-METHOXYCARBONYLMETHYLPHENYL)BORONIC ACID PINACOL ESTER
• Synonyms: Methyl [4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetate;Benzeneacetic acid, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, methyl ester;methyl 2-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetate;[4-(Methoxycarbonyl)methyl]benzeneboronicacidpinacolester;Methyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl);(4-METHOXYCARBONYLMETHYLPHENYL)BORONIC ACID PINACOL ESTER;Methyl 2-(4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate
• CAS NO: 454185-98-9
• Molecular Formula: C₁₅H₂₁BO₄
• Molecular Weight: 276.14
• Mol File: 454185-98-9.mol
• Article Data: 26

Chemical Properties

• Boiling Point: 363°C at 760 mmHg
• Flash Point: 173.4°C
• Appearance: /
• Density: 1.07g/cm³
• Vapor Pressure: 1.86E-05mmHg at 25°C
• Refractive Index: 1.497
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: soluble in Methanol
• CAS DataBase Reference: (4-METHOXYCARBONYLMETHYLPHENYL)BORONIC ACID PINACOL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (4-METHOXYCARBONYLMETHYLPHENYL)BORONIC ACID PINACOL ESTER(454185-98-9)
• EPA Substance Registry System: (4-METHOXYCARBONYLMETHYLPHENYL)BORONIC ACID PINACOL ESTER(454185-98-9)

Safety Data

• Hazardous Substances Data: 454185-98-9(Hazardous Substances Data)

Usage

Uses

(4-Methoxycarbonylmethyl)phenylboronic acid pinacol ester

InChI:InChI=1/C15H21BO4/c1-14(2)15(3,4)20-16(19-14)12-8-6-11(7-9-12)10-13(17)18-5/h6-9H,10H2,1-5H3

Upstream product

• 34837-84-8 4-fluorobenzeneacetic acid methyl ester 
• 73183-34-3 bis(pinacol)diborane 
• 101-41-7 benzeneacetic acid methyl ester 
• 41841-16-1 (4-bromo-phenyl)-acetic acid methyl ester 
• 67-56-1 methanol 
• 128376-64-7 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde 
• 70290-37-8 (4-methylsulfanyl-phenyl)-acetic acid methyl ester 
• 1878-68-8 2-(4-bromophenyl)-acetic acid 
• 797755-07-8 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetic acid 
• 14199-15-6 Methyl 4-hydroxyphenylacetate 
• 147283-85-0 (4-Trifluoromethanesulfonyloxy-phenyl)-acetic acid methyl ester 

Downstream Products

• 917024-79-4 (4'-{1-ethyl-1-[4-((E)-3-ethyl-3-hydroxy-1-pentenyl)-3-methylphenyl]propyl}-2'-methylbiphenyl-4-yl)acetic acid methyl ester 
• 1228103-47-6 2-(4-(4-(3-(t-butyldimethylsiloxy)phenylamino)thieno[3,2-d]pyrimidin-6-yl)phenyl)ethanol 
• 1228103-48-7 4-(4-(3-(t-butyldimethylsiloxy)phenylamino)thieno[3,2-d]pyrimidin-6-yl)phenethyl methanesulfonate 
• 1228103-49-8 N-(3-(t-butyldimethylsiloxy)phenyl)-6-(4-(2-morpholinoethyl)phenyl)thieno[3,2-d]pyrimidin-4-amine 
• 1228103-50-1 2-(4-(4-(3-hydroxyphenylamino)thieno[3,2-d]pyrimidin-6-yl)phenyl)acetic acid 
• 1228101-38-9 2-(4-(4-(3-hydroxyphenylamino)thieno[3,2-d]pyrimidin-6-yl)phenyl)-1-(4-methylpiperazin-1-yl)ethanone 
• 885681-52-7 methyl [4-(5-hydroxy-2-pyridinyl)phenyl]acetate 
• 701271-66-1 tert-butyl 4-({6-[4-(2-methoxy-2-oxoethyl)phenyl]pyridin-3-yl}sulfonyl)tetrahydro-2H-pyran-4-carboxylate 
• 454186-06-2 8-{4-[2-(ethoxycarbonyl-methyl-amino)-ethyl]-2-nitro-phenoxy}-1-[4-(2-isopropoxy-5-methoxycarbonyl-phenoxy)-benzyl]-6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester 

Relevant articles and documents

Photo-induced thiolate catalytic activation of inert Caryl-hetero bonds for radical borylation

Substantial effort is currently being devoted to obtaining photoredox catalysts with high redox power. Yet, it remains challenging to apply the currently established methods to the activation of bonds with high bond dissociation energy and to substrates with high reduction potentials. Herein, we introduce a novel photocatalytic strategy for the activation of inert substituted arenes for aryl borylation by using thiolate as a catalyst. This catalytic system exhibits strong reducing ability and engages non-activated Caryl–F, Caryl–X, Caryl–O, Caryl–N, and Caryl–S bonds in productive radical borylation reactions, thus expanding the available aryl radical precursor scope. Despite its high reducing power, the method has a broad substrate scope and good functional-group tolerance. Spectroscopic investigations and control experiments suggest the formation of a charge-transfer complex as the key step to activate the substrates.

Pd-Catalyzed Site-Selective Borylation of Simple Arenes via Thianthrenation?

Site-selective borylation of simple arenes was realized in one pot via an electrophilic thianthrenation/Pd-catalyzed borylation sequence. The key to achieve this operatically simple process is the use of Pd catalysis, which could tolerate the solvent and acidic conditions used in the thianthrenation step. This protocol features mild conditions, broad functional group tolerance, and simple manipulations, and is suitable for late-stage functionalization of a wide range of pharmaceuticals and complex bioactive molecules.

Rhodium-Catalyzed ipso-Borylation of Alkylthioarenes via C-S Bond Cleavage

Rhodium-catalyzed transformation of alkyl aryl sulfides into arylboronic acid pinacol esters via C-S bond cleavage is reported. In combination with transition-metal-catalyzed sulfanyl group-guided regioselective C-H borylation reactions of alkylthioarenes, this method allows the synthesis of a diverse range of multisubstituted arenes.