118803-40-0

Basic information

• Product Name: (2-HYDROXYMETHYL-5-NITRO)BENZENEBORONIC ACID DEHYDRATE
• Synonyms: (2-HYDROXYMETHYL-5-NITRO)BENZENEBORONIC ACID DEHYDRATE;(2-HYDROXYMETHYL-5-NITRO)PHENYLBORONIC ACID, DEHYDRATE;1-HYDROXY-6-NITRO-2,1-BENZOXABOROLANE;2-Hydroxymethyl-5-nitrophenylboronic acid, dehydrated;2-Hydroxymethyl-5-nitrophenylboronic acid;2-HydroxyMethyl-5-nitrobenzeneboronic acid heMiester, 96%;6-Nitrobenzo[c][1,2]oxaborol-1(3H)-ol;2,1-Benzoxaborole, 1,3-dihydro-1-hydroxy-6-nitro-
• CAS NO: 118803-40-0
• Molecular Formula: C₇H₆BNO₄
• Molecular Weight: 178.94
• Product Categories: blocks;BoronicAcids;NitroCompounds
• Mol File: 118803-40-0.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 330.6±52.0 °C(Predicted)
• Appearance: /
• Density: 1.43±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility: Acetonitrile (Slightly), DMSO (Slightly)
• PKA: 5.90±0.20(Predicted)
• CAS DataBase Reference: (2-HYDROXYMETHYL-5-NITRO)BENZENEBORONIC ACID DEHYDRATE(CAS DataBase Reference)
• NIST Chemistry Reference: (2-HYDROXYMETHYL-5-NITRO)BENZENEBORONIC ACID DEHYDRATE(118803-40-0)
• EPA Substance Registry System: (2-HYDROXYMETHYL-5-NITRO)BENZENEBORONIC ACID DEHYDRATE(118803-40-0)

Safety Data

• Hazardous Substances Data: 118803-40-0(Hazardous Substances Data)

Usage

Description

(2-HYDROXYMETHYL-5-NITRO)BENZENEBORONIC ACID DEHYDRATE is an organic compound with the molecular formula C7H9BNO6?H2O. It is a derivative of benzeneboronic acid, featuring a hydroxymethyl group at the 2nd position and a nitro group at the 5th position. The dehydrated form of this compound is used in various applications due to its unique chemical properties.

Uses

Used in Chemical Synthesis:
(2-HYDROXYMETHYL-5-NITRO)BENZENEBORONIC ACID DEHYDRATE is used as a reactant/reagent for imprinted polymers, playing a crucial role in the synthesis of these materials. Its specific functional groups allow for the creation of polymers with tailored properties and high selectivity.
Used in Regioselective Modification:
In the field of organic chemistry, (2-HYDROXYMETHYL-5-NITRO)BENZENEBORONIC ACID DEHYDRATE serves as a protecting group for regioselective modification of polyfunctional substrates. This application is essential for controlling the reaction outcome and ensuring the formation of the desired product with a specific functional group or stereochemistry.
Used in Pharmaceutical Industry:
(2-HYDROXYMETHYL-5-NITRO)BENZENEBORONIC ACID DEHYDRATE can be utilized in the development of new drugs and drug candidates. Its unique structure and reactivity make it a valuable building block for the synthesis of complex molecules with potential therapeutic applications.
Used in Material Science:
The compound can also be employed in the development of new materials with specific properties, such as sensors, catalysts, or advanced polymers. Its ability to form stable complexes with various substrates makes it a promising candidate for these applications.

Upstream product

• 5735-41-1 3H-benzo[c][1,2]oxaborol-1-ol 
• 40138-16-7 2-formylbenzene boronic acid 
• 7697-37-2 nitric acid 
• 99-55-8 2-methyl-5-nitroaniline 
• 2096333-96-7 2-(2-(bromomethyl)-5-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1310-73-2 sodium hydroxide 
• 957062-84-9 4,4,5,5-tetramethyl-2-(2-methyl-5-nitrophenyl)-1,3,2-dioxaborolane 

Downstream Products

• 117098-94-9 (5-amino-2-hydroxymethylphenyl)boronic acid 

Relevant articles and documents

Protection of the Benzoxaborole Moiety: Synthesis and Functionalization of Zwitterionic Benzoxaborole Complexes

The synthesis and utility of three benzoxaborole protecting groups are reported. These protecting groups improve organic solubility and allow otherwise incompatible reactions (oxidations, substitutions, and mild reductions) to be achieved in the presence of the benzoxaborole moiety. 3-(N,N-Dimethylamino)-1-propanol was determined to be useful in one-step sequences and is readily cleaved upon workup. Two other groups, N-methylsalicylidenimine and 2-[1-(methylimino)ethyl]phenol, are suitable for multistep syntheses. Deprotection with mild aqueous acid allows for chromatography-free isolation of the benzoxaborole in high yields.

Synthesis and biological evaluation of arylphosphonium-benzoxaborole conjugates as novel anticancer agents

Arylphosphonium-benzoxaborole conjugates have been synthesized as potential mitochondria targeting anticancer agents. The synthesized compounds have been tested for their effects on cell viability in various solid tumor cell lines including breast cancer 4T1 and MCF-7, pancreatic cancer MIAPaCa-2 and colorectal adenocarcinoma WiDr. Compound 6c is designated as a lead compound for further studies due to its enhanced effects on cell viability in the above-mentioned cell lines. Seahorse Xfe96 based metabolic assays reveal that the lead candidate 6c inhibits mitochondrial respiration in 4T1 and WiDr cell lines as evidenced by the reduction of mitochondrial ATP production and increase in proton leak. Epiflourescent microscopy experiments also illustrate that 6c causes significant mitochondrial fragmentation in 4T1 and WiDr cells, morphologically consistent with programmed cell death. Our current studies illustrate that arylphosphonium-benzoxaborole conjugates have potential to be further developed as anticancer agents.

PROTECTIVE GROUPS AND METHODS FOR PROTECTING BENZOXABOROLES OR OXABOROLES

The present invention relates in part protective groups that can be used to reversibly protect benzoxaboroles and/or oxaboroles and yield the corresponding protected complexes. The invention further relates to the use of these protective groups to protect benzoxaboroles and/or oxaboroles.