85199-06-0

Basic information

• Product Name: 2,5-Dimethylphenylboronic acid
• Synonyms: P-XYLENE-2-BORONIC ACID;RARECHEM AH PB 0089;RARECHEM AH PB 0196;CHEMBRDG-BB 4003297;AKOS BRN-0086;AKOS BRN-0066;2,5-DIMETHYLPHENYLBORONIC ACID;2,5-DIMETHYLBENZENEBORONIC ACID
• CAS NO: 85199-06-0
• Molecular Formula: C₈H₁₁BO₂
• Molecular Weight: 149.98
• Product Categories: blocks;BoronicAcids;Boric Acid;Heterocyclic Compounds;Boronic Acid;Aryl;Organoborons;B (Classes of Boron Compounds);Boronic Acids;Boronic Acids;Boronic Acids and Derivatives;Aryl Boronic Acids;Boronic Acids and Derivatives;Chemical Synthesis;Disubstituted Aryl Boronic Acids;Organometallic Reagents;Boronate Ester;Potassium Trifluoroborate
• Mol File: 85199-06-0.mol
• Article Data: 7

Chemical Properties

• Melting Point: 186-191 °C(lit.)
• Boiling Point: 305.1 °C at 760 mmHg
• Flash Point: 138.3 °C
• Appearance: white to light yellow crystal powder
• Density: 1.07 g/cm³
• Vapor Pressure: 0.000367mmHg at 25°C
• Refractive Index: 1.523
• Storage Temp.: 0-6°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 8.70±0.58(Predicted)
• BRN: 3241785
• CAS DataBase Reference: 2,5-Dimethylphenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Dimethylphenylboronic acid(85199-06-0)
• EPA Substance Registry System: 2,5-Dimethylphenylboronic acid(85199-06-0)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-22
• Safety Statements: 37/39-26-36/37
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 85199-06-0(Hazardous Substances Data)

Usage

Description

2,5-Dimethylphenylboronic acid is an organic compound with the chemical formula C8H11BO2. It is a white to light yellow crystalline powder that is soluble in water and has a characteristic aromatic smell. 2,5-Dimethylphenylboronic acid is a derivative of boronic acid, which is known for its unique chemical properties and reactivity.

Uses

Used in Pharmaceutical Industry:
2,5-Dimethylphenylboronic acid is used as a reactant for Friedel-Crafts alkylation and Suzuki-Miyaura coupling reactions. These reactions are widely employed in the synthesis of various pharmaceutical compounds, including antibiotics, anti-inflammatory drugs, and anticancer agents. The versatility of these reactions allows for the creation of a wide range of complex organic molecules with potential therapeutic applications.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2,5-Dimethylphenylboronic acid is used as a reactant for the Suzuki reaction, a type of cross-coupling reaction that forms carbon-carbon bonds. This reaction is particularly useful for the synthesis of complex organic molecules, such as natural products, pharmaceuticals, and advanced materials. The Suzuki reaction is known for its mild reaction conditions, high yields, and compatibility with a wide range of functional groups, making it a popular choice for chemists.
Used in Organic Chemistry Research:
2,5-Dimethylphenylboronic acid is also used as a research tool in organic chemistry. Its unique reactivity and properties make it an interesting subject for studying various chemical reactions and mechanisms. Researchers can use this compound to explore new synthetic routes, develop novel catalysts, and investigate the fundamental principles of organic chemistry.

InChI:InChI=1/C8H11BO2/c1-6-3-4-7(2)8(5-6)9(10)11/h3-5,10-11H,1-2H3

Upstream product

• 121-43-7 Trimethyl borate 
• 553-94-6 4-bromo-m-xylene 
• 11113-50-1 boric acid 
• 7732-18-5 water 
• 101436-74-2 bis-(2,5-dimethyl-phenyl)-mercury 
• 30897-86-0 2,5-dimethylphenylmagnesium bromide 
• 21022-98-0 (2,5-dimethylphenyl)dichloroborane 

Downstream Products

• 856413-61-1 4-(2,5-dimethylphenyl)-2-methyl-3,5,6,7-tetrahydro-s-indacen-1(2H)-one 
• 613660-93-8 3-(2,5-dimethylphenyl)-5-[(2-methylpyrrolidin-1-yl)carbonyl]pyridine 
• 246219-76-1 methyl (S)-2-[3-(2-benzyloxy-1-methylethyl)-2-(3,5-dimethyl-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-methylpropanoate 
• 884738-28-7 4-bromo-3-cyano-5-(2.5-dimethylphenyl)-2-nitrothiophene 
• 1285147-54-7 C₁₅H₁₅BrO 
• 856413-66-6 4-(2,5-dimethylphenyl)-6-methyl-1,2,3,5-tetrahydro-s-indacene 
• 1341198-19-3 (CH₃)3CC₆H₄C₉H₅CH(CH₃)2Si(CH₃)2C₁₂H₉(CH₃)(C₆H₃(CH₃)2) 
• 1231645-94-5 4-(2,5-dimethylphenyl)-5-methylindene 
• 1537172-08-9 2-(3,3-difluoroallyl)-1,4-dimethylbenzene 
• 1537171-84-8 2-(1,1-difluoroallyl)-1,4-dimethylbenzene 

Relevant articles and documents

Exploiting Potential Inversion for Photoinduced Multielectron Transfer and Accumulation of Redox Equivalents in a Molecular Heptad

Photoinduced multielectron transfer and reversible accumulation of redox equivalents is accomplished in a fully integrated molecular heptad composed of four donors, two photosensitizers, and one acceptor. The second reduction of the dibenzo[1,2]dithiin acceptor occurs more easily than the first by 1.3 V, and this potential inversion facilitates the light-driven formation of a two-electron reduced state with a lifetime of 66 ns in deaerated CH3CN. The quantum yield for formation of this doubly charge-separated photoproduct is 0.5%. In acidic oxygen-free solution, the reduction product is a stable dithiol. Under steady-state photoirradiation, our heptad catalyzes the two-electron reduction of an aliphatic disulfide via thiolate-disulfide interchange. Exploitation of potential inversion for the reversible light-driven accumulation of redox equivalents in artificial systems is unprecedented and the use of such a charge-accumulated state for multielectron photoredox catalysis represents an important proof-of-concept.

Pyrene derivatives comprising heteroaryl amine group and organic light-emitting diode including the same

The present invention relates to a pyrene derivative represented by chemical formula A, and an organic light-emitting diode including the same. In the chemical formula A, substituents Z, Ar_1, Ar_2, R_1 to R_5, connecting groups L_1 and L_2, and X, m, p and q are the same as defined in a detailed description of the present invention.COPYRIGHT KIPO 2015

New phenyl-substituted PPV derivatives for polymer light-emitting diodes-synthesis, characterization and structure-property relationship study

Three new PPV derivatives with dialkoxyphenyl substituents, BEH2P-PPV, BEH3P-PPV, and BEH4P-PPV have been synthesized. The polymers were characterized by FT-IR, 1H NMR, and elemental analysis. The polymers possess excellent solubility, high molecular weights, high photoluminescence efficiencies and good thermal stability. The influence of substitution pattern on the formation of structural defects has been investigated by measuring the signal due to tolane-bisbenzyl moieties (TBB) in the proton NMR spectra. BEH2P-PPV with a steric phenyl group at the ortho-position on the side phenyl ring shows the lowest amount of TBB, which indicates suitable steric hindrance can be applied to suppress the formation of irregular head-to-head and tail-to-tail linkage in the polymer chains. In addition, the polarity of solvents used for the Gilch polymerization will also affect the amount of irregular structure in the polymers. Polar solvents such as THF will result in polymers with low TBB content. Energy level measurement from cyclic voltammetry revealed that the influences of the substitution pattern on the HOMOs and LUMOs are different. The three polymers possess similar HOMO energy levels while the LUMO of BEH4P-PPV is much higher than that of the other two polymers. Polymer light-emitting diodes fabricated from BEH2P-PPV, BEH3P-PPV, and BEH4P-PPV with the configuration of ITO/PEDOT/polymer/Ba/Al, emitted bright blue-green to green light with the maximum peaks at 496, 488, and 525 nm, respectively. The turn-on electric field and maximum external quantum efficiencies of the diodes are 0.30, 0.50, and 0.42 MV/cm and 0.37%, 0.66%, and 0.25% respectively. The quantum efficiency is mainly determined by the electron injection from the cathode. With the highest luminance, lowest turn-on electric field, and good quantum efficiency as well as negligible structural defects, BEH2P-PPV is the most promising material among the three polymers for polymer light-emitting diodes.