143697-03-4

Basic information

• Product Name: (4-METHYL-2-NITRO)BENZENEBORONIC ACID
• Synonyms: (4-METHYL-2-NITRO)BENZENEBORONIC ACID;(4-METHYL-2-NITROPHENYL)BORONIC ACID
• CAS NO: 143697-03-4
• Molecular Formula: C₇H₈BNO₄
• Molecular Weight: 180.95
• Product Categories: blocks;BoronicAcids
• Mol File: 143697-03-4.mol

Chemical Properties

• Melting Point: 240-244
• Boiling Point: 382.8 °C at 760 mmHg
• Flash Point: 185.3 °C
• Appearance: /
• Density: 1.33 g/cm³
• Vapor Pressure: 1.53E-06mmHg at 25°C
• Refractive Index: 1.563
• Storage Temp.: Keep Cold
• CAS DataBase Reference: (4-METHYL-2-NITRO)BENZENEBORONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (4-METHYL-2-NITRO)BENZENEBORONIC ACID(143697-03-4)
• EPA Substance Registry System: (4-METHYL-2-NITRO)BENZENEBORONIC ACID(143697-03-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 143697-03-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(4-METHYL-2-NITRO)BENZENEBORONIC ACID is used as a key reagent in Suzuki-Miyaura cross-coupling reactions for the formation of carbon-carbon bonds. Its boronic acid functional group allows for the efficient formation of these bonds, which are crucial in the synthesis of complex organic molecules.
Used in Medicinal Chemistry:
(4-METHYL-2-NITRO)BENZENEBORONIC ACID is used as a precursor in the synthesis of pharmaceuticals and agrochemicals. Its unique reactivity and the presence of the nitro group enable the introduction of this functional group into more complex molecules, contributing to the development of novel therapeutic agents and agrochemicals.
Used in the Synthesis of Complex Molecules:
(4-METHYL-2-NITRO)BENZENEBORONIC ACID is used as a versatile building block in the synthesis of complex organic molecules. Its reactivity and the presence of the nitro group allow for the introduction of this functional group into more complex structures, facilitating the development of innovative compounds with potential applications in various fields.

InChI:InChI=1/C7H8BNO4/c1-5-2-3-6(8(10)11)7(4-5)9(12)13/h2-4,10-11H,1H3

Upstream product

• 5326-39-6 4-iodo-3-nitrotoluene 
• 121-43-7 Trimethyl borate 

Relevant articles and documents

Promoting reductive tandem reactions of nitrostyrenes with Mo(CO)6 and a palladium catalyst to produce 3 h -indoles

The combination of Mo(CO)6 and 10 mol % of palladium acetate catalyzes the transformation of 2-nitroarenes to 3H-indoles through a tandem cyclization-[1,2] shift reaction of in situ generated nitrosoarenes. Mo(CO)6 appears to have dual roles in this transformation: generate CO and promote C-N bond formation to increase the yield of the N-heterocycle product.

MACROCYCLIC INHIBITORS OF HEPATITIS C VIRUS

Inhibitors of HCV replication of formula (I) and the N-oxides, salts, or stereoisomers thereof, wherein each dashed line (represented by ------) represents an optional double bond; X is N, CH and where X bears a double bond it is C; R1 is -OR6, -NH-SO2R7; R2 is hydrogen, and where X is C or CH, R2 may also be C1-6alkyl; R3 is hydrogen, C1-6alkyl, C1-6alkoxyC1-6alkyl, or C3-7cycloalkyl; n is 3, 4, 5, or 6; R4 and R5 independently from one another are hydrogen, halo, hydroxy, nitro, cyano, carboxyl, C1-6alkyl, C1-6alkoxy, C1-6alkoxyC1-6alkyl, C1-6alkylcarbonyl, C1-6alkoxy- carbonyl, amino, azido, mercapto, C1-6alkylthio, polyhaloC1-6alkyl, aryl or Het; W is aryl or Het; R6 is hydrogen; aryl; Het; C3-7cycloalkyl optionally substituted with C1-6alkyl; or C1-6alkyl optionally substituted with C3-7cycloalkyl, aryl or with Het; R7 is aryl; Het; C3-7cycloalkyl optionally substituted with C1-6alkyl; or C1-6alkyl optionally substituted with C3-7cycloalkyl, aryl or with Het; aryl is phenyl or naphthyl, each optionally substituted with 1-3 substituents; Het is a 5 or 6 membered saturated, partially unsaturated or completely unsaturated heterocyclic ring containing 1 - 4 heteroatoms each independently selected from N, O or S, and optionally substituted with 1 -3 substituents; pharmaceutical compositions containing compounds (I) and processes for preparing compounds (I). Bioavailable combinations of the inhibitors of HCV of formula (I) with ritonavir are also provided.

A facile and convenient synthesis of functionalized ortho- nitrophenylboronic acids

A variety of ortho-nitrophenylboronic acids bearing functional groups such as cyano, nitro, halo, α-bromomethyl, and ester were prepared in good yields via I-Mg exchange followed by quenching with trimethyl borate. All reagents employed in this procedure are commercially available and were used without further purification, and the procedure can be executed in about an hour.