133730-34-4

Basic information

• Product Name: 2,4-Dimethoxybenzeneboronic acid
• Synonyms: RARECHEM AH PB 0099;AKOS BRN-0063;2,4-DIMETHOXYPHENYLBORONIC ACID;2,4-DIMETHOXYBENZENEBORONIC ACID;2,4-DIMETHOXYBENZENEBORONIC ACID,98+%;2,4-Dimethoxyphenylboronic Acid (contains varying amounts of Anhydride);2,4-Dimethoxyphenylboronic acid ,98%;2,4-Dimethoxybenzeneboronic acid,97%
• CAS NO: 133730-34-4
• Molecular Formula: C₈H₁₁BO₄
• Molecular Weight: 181.98
• EINECS: -0
• Product Categories: blocks;BoronicAcids;Substituted Boronic Acids;Boronic acids;Boronic Acid;Alkoxy;Aryl;Organoborons;B (Classes of Boron Compounds);Boronic Acids;Boronic Acids and Derivatives;Aryl Boronic Acids;Boronic Acids and Derivatives;Chemical Synthesis;Disubstituted Aryl Boronic Acids;Organometallic Reagents
• Mol File: 133730-34-4.mol
• Article Data: 10

Chemical Properties

• Melting Point: 125-127 °C(lit.)
• Boiling Point: 361.1 °C at 760 mmHg
• Flash Point: 172.2 °C
• Appearance: white to beige or pink moist powder
• Density: 1.19 g/cm³
• Vapor Pressure: 7.61E-06mmHg at 25°C
• Refractive Index: 1.517
• Storage Temp.: 0-6°C
• Solubility: soluble in Methanol
• PKA: 8.98±0.58(Predicted)
• BRN: 4744213
• CAS DataBase Reference: 2,4-Dimethoxybenzeneboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dimethoxybenzeneboronic acid(133730-34-4)
• EPA Substance Registry System: 2,4-Dimethoxybenzeneboronic acid(133730-34-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26-36/37-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 133730-34-4(Hazardous Substances Data)

Usage

Description

2,4-Dimethoxybenzeneboronic acid is an organic compound with the chemical formula C8H11BO4, featuring a boron atom bonded to a benzene ring with two methoxy groups at the 2nd and 4th positions. It is a white to beige or pink moist powder and is known for its reactivity in various chemical reactions.

Uses

Used in Pharmaceutical Industry:
2,4-Dimethoxybenzeneboronic acid is used as a reactant for Suzuki-Miyaura and Negishi couplings, which are essential in the synthesis of complex organic molecules, including those with pharmaceutical applications. These coupling reactions facilitate the formation of carbon-carbon bonds, enabling the creation of a wide range of bioactive compounds.
Used in Chemical Synthesis:
2,4-Dimethoxybenzeneboronic acid is used as a reactant in metal-catalyzed Suzuki-Miyaura cross-coupling reactions, which are crucial for the synthesis of various organic compounds. It is particularly useful in the preparation of hydroxy(trimethoxy)phenanthrene by cross-coupling with bromo(benzyloxy)methoxybenzaldehyde, followed by condensation and debenzylation reactions.
Used in Material Science:
In the field of material science, 2,4-Dimethoxybenzeneboronic acid is used to synthesize 2,4-dimethoxy-1-(trifluoromethyl)benzene via Cu-catalyzed trifluoromethylation reactions. This synthesized compound can be utilized in the development of new materials with specific properties, such as enhanced stability or reactivity.
Overall, 2,4-Dimethoxybenzeneboronic acid is a versatile compound with applications in various industries, including pharmaceuticals, chemical synthesis, and material science, due to its reactivity and ability to form complex organic molecules through different coupling reactions.

InChI:InChI=1/C8H11BO4/c1-12-6-3-4-7(9(10)11)8(5-6)13-2/h3-5,10-11H,1-2H3

Upstream product

• 17715-69-4 1-Bromo-2,4-dimethoxybenzene 
• 151-10-0 1,3-Dimethoxybenzene 
• 1033691-64-3 C₈H₉BF₃O₂^(1-) 
• 688-74-4 boric acid tributyl ester 
• 138109-49-6 2,4-dimethoxyphenylmagnesium bromide 
• 5419-55-6 Triisopropyl borate 
• 67-56-1 methanol 
• 55124-35-1 diisopropylamine borane 

Downstream Products

• 131575-57-0 4-(2,4-Dimethoxyphenyl)-2H-1-benzopyran-2-one 
• 1025908-97-7 6-benzyloxy-5-(2,4-dimethoxy-phenyl)-4-methoxy-benzo[1,3]dioxole 
• 1026057-62-4 4-(2-benzyl-benzo[b]thiophen-3-yl)-5'-bromo-2'',4''-dimethoxy-[1,1';3',1'']terphenyl-4'-ol 
• 1067228-95-8 2-(2,4-dimethoxy-phenyl)-4-methoxy-6-methyl-5-nitro-pyrimidine 
• 733776-45-9 6-(2,4-dimethoxyphenyl)nicotinic acid 
• 108474-22-2 2',4'-dimethoxy-biphenyl-4-carboxylic acid 
• 862168-13-6 4-chloro-6-(2,4-dimethoxy-phenyl)-pyrimidin-2-ylamine 
• 796843-31-7 4-benzyloxy-5,2',4'-trimethoxy-biphenyl-2-carbaldehyde 

Relevant articles and documents

Magnesium promoted autocatalytic dehydrogenation of amine borane complexes: A reliable, non-cryogenic, scalable access to boronic acids

Owing to the unusual reactivity of dialkylamine-borane complexes, a methodology was developed to simply access boronic acids. The intrinsic instability of magnesium aminoborohydride was tweaked into a tandem dehydrogenation borylation sequence. Proceeding via an autocatalytic cycle, amineborane dehydrogenation was induced by a variety of Grignard reagents. Overall, addition of the organomagnesium species onto specially designed dialkylamine-borane complexes led to a variety of boronic acids in high yields. In addition, the reaction can be performed under Barbier conditions, on a large scale.

PATCH FOR ANTI-DERMATOPHYTOSIS

A patch for nails or skin for prevention or treatment of dermatophytosis, containing a layer including a pressure sensitive adhesive layer and a compound represented by the formula: wherein R1 represents hydrogen, C1-16 alkyl, or trifluoromethyl; R2 represents hydrogen, C1-6 alkyl, halogen, —COO(C1-6 alkyl), or (CH2)1-3COOR; R3 represents hydrogen, C1-6 alkyl, amino, trifluoromethyl, or OR; R4 represents hydroxyl; R5 represents hydrogen, C1-6 alkyl, hydroxyl, or halogen; R6 represents hydrogen, C1-6 alkyl, trifluoromethyl, halogen, amino, —NRaRb, nitro, hydroxy-C1-6 alkyl, —CONRaRb, —COO(C1-6 alkyl), —COOH, —(CH2)1-3COOR, or ORa (Ra and Rb each represents hydrogen, C1-6 alkyl, or C1-6 acyl); R7 represents hydrogen, C1-6 alkyl, —OR, or halogen; R8 represents hydrogen, C1-6 alkyl, hydroxyl, amino, or nitro; and R represents hydrogen or C1-6 alkyl; or a salt thereof.

TOPICAL LIQUID AGENT FOR THE TREATMENT OF DERMATOPHYTOSIS

A topical liquid agent for a nail and/or skin for prevention or treatment of dermatophytosis comprises a film-forming agent and a compound represented by the formula: wherein R1 represents hydrogen, C1-6 alkyl, or trifluoromethyl, R2 represents hydrogen, C1-6 alkyl, halogen, —COO(C1-6 alkyl), or (CH2)1-3COOR where R represents hydrogen or C1-6 alkyl, R3 represents hydrogen, C1-6 alkyl, amino, trifluoromethyl, or OR where R represents hydrogen or C1-6 alkyl, R4 represents hydroxyl, R5 represents hydrogen, C1-6 alkyl, hydroxyl, or halogen, R6 represents hydrogen, C1-6 alkyl, trifluoromethyl, halogen, amino, —NRaRb, nitro, hydroxy-C1-6 alkyl, —CONRaRb, —COO(C1-6 alkyl), —COOH, —(CH2)1-3COOR, or ORa where R represents hydrogen or C1-6 alkyl, Ra and Rb each represent hydrogen, C1-6 alkyl, or C1-6 acyl, R7 represents hydrogen, C1-6 alkyl, —OR where R represents hydrogen or C1-6 alkyl, or halogen, R8 represents hydrogen, C1-6 alkyl, hydroxyl, amino, or nitro, or a salt thereof.