1016-58-6

Basic information

• Product Name: 4,5-DIMETHOXY-2-NITROBENZYL ALCOHOL
• Synonyms: RARECHEM AL BD 0187;TIMTEC-BB SBB009964;LABOTEST-BB LT00847721;6-NITROVERATRYL ALCOHOL;4,5-DIMETHOXY-2-NITROBENZYL ALCOHOL;4,5-Dimethoxy-2-nitrobenzyl alcohol 98%;6-NITROVERATRYL ALCOHOL 98+%;4,5-Dimethoxy-2-nitrobenzyl alcohol, 98+%
• CAS NO: 1016-58-6
• Molecular Formula: C₉H₁₁NO₅
• Molecular Weight: 213.19
• EINECS: 213-806-4
• Product Categories: Benzhydrols, Benzyl & Special Alcohols;Alcohols;Building Blocks;C9 to C10;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 1016-58-6.mol
• Article Data: 19

Chemical Properties

• Melting Point: 145-148 °C(lit.)
• Boiling Point: 383.9 °C at 760 mmHg
• Flash Point: 186 °C
• Appearance: white to light yellow crystal powder
• Density: 1.307 g/cm³
• Vapor Pressure: 1.4E-06mmHg at 25°C
• Refractive Index: 1.558
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 13.59±0.10(Predicted)
• Water Solubility: Soluble in water.
• Sensitive: Light Sensitive
• BRN: 1880093
• CAS DataBase Reference: 4,5-DIMETHOXY-2-NITROBENZYL ALCOHOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-DIMETHOXY-2-NITROBENZYL ALCOHOL(1016-58-6)
• EPA Substance Registry System: 4,5-DIMETHOXY-2-NITROBENZYL ALCOHOL(1016-58-6)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 8
• HazardClass: IRRITANT
• Hazardous Substances Data: 1016-58-6(Hazardous Substances Data)

Usage

Description

4,5-Dimethoxy-2-nitrobenzyl alcohol, also known as 6-Nitroveratryl Alcohol, is a 2-nitrobenzyl alcohol derivative. It is an oxidation product of veratryl (3,4-dimethoxybenzyl) alcohol by lignin peroxidase, which is isolated from Phanerochaete chrysosporium. 4,5-DIMETHOXY-2-NITROBENZYL ALCOHOL is characterized by its white to light yellow crystal powder appearance.

Uses

Used in Organic Synthesis:
4,5-Dimethoxy-2-nitrobenzyl alcohol is used as a reagent for the protection of alcohols, specifically as ethers that can be cleaved by photolysis involving intramolecular rearrangement to derivatives of o-nitrosobenzaldehyde. These derivatives are readily cleaved by hydrolysis, making this compound a valuable asset in organic synthesis.
Used in Pharmaceutical Industry:
4,5-Dimethoxy-2-nitrobenzyl alcohol serves as a pharmaceutical intermediate, playing a crucial role in the development and synthesis of various pharmaceutical compounds.
Used in Photochemistry:
4,5-DIMETHOXY-2-NITROBENZYL ALCOHOL is also utilized as photochemical protecting groups in organic synthesis, which is essential for controlling the reactivity of certain functional groups during chemical reactions.
Used in Synthesis of Photolabile Monomers and Ligands:
4,5-Dimethoxy-2-nitrobenzyl alcohol (6-nitroveratryl alcohol) is a suitable reagent used in the synthesis of 4,5-dimethoxy-2-nitrobenzyl methacrylate, a photolabile monomer, and 2-(4-((4-(4,5-dimethoxy-2-nitrobenzyloxy)phenyl)cyclohexylidene)methyl)phenoxy)-N,N-dimethylethanamine, a caged cyclofen-OH ligand. These compounds are essential in various applications, such as controlled drug release and molecular switches.
Used in Synthesis of Photolabile Protecting Groups:
The compound is also used in the synthesis of several photolabile protecting groups, such as 1-[[(chlorocarbonyl)oxy]methyl]-4,5-dimethoxy-2-nitrobenzenebis(4,5-dimethoxy-2-nitrophenyl)ethylene glycol, nitroveratryl (NV) protected α-hydroxyacetic acid (αG) (NV-αG-OH), and 4,5-dimethoxy-2-nitrobenzyl p-nitro-phenylcarbonate. These protecting groups are vital in the synthesis of various biologically active molecules and pharmaceutical compounds.
Used in Amino Sugars Protection:
4,5-Dimethoxy-2-nitrobenzyl alcohol is also used in the synthesis of 6-nitroveratryloxycarbonyl chloride (NVOCCl), a reagent employed in the protection of amino functions in amino sugars. This application is crucial for the synthesis of complex carbohydrates and their derivatives, which have significant biological importance.

InChI:InChI=1/C9H11NO5/c1-14-8-3-6(5-11)7(10(12)13)4-9(8)15-2/h3-4,11H,5H2,1-2H3

Upstream product

• 20357-25-9 6-nitroveratraldehyde 
• 165811-64-3 4,5-dimethoxy-2-nitrobenzyl 2-aminoacetate hydrochloride 
• 1236141-68-6 C₂₄H₃₁N₃O₁₀ 
• 121-33-5 vanillin 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 93-03-8 (3,4-dimethoxyphenyl)methanol 

Downstream Products

• 119137-01-8 Anthracen-2-yl-carbamic acid 4,5-dimethoxy-2-nitro-benzyl ester 
• 132018-90-7 N-Boc-L-aspartic acid α-tert-butyl β-6-nitroveratryl diester 
• 123330-63-2 [(2-{2-[2-(Bis-carboxymethyl-amino)-phenoxy]-ethoxy}-phenyl)-(4,5-dimethoxy-2-nitro-benzyloxycarbonylmethyl)-amino]-acetic acid 
• 53413-67-5 6-nitroveratrylbromide 
• 20357-25-9 6-nitroveratraldehyde 
• 119137-07-4 4,5-dimethoxy-2-nitrosobenzaldehyde 
• 15862-94-9 1-(chloromethyl)-4,5-dimethoxy-2-nitrobenzene 
• 97207-55-1 4,5-Dimethoxy-2-nitrobenzyl methyl ether 
• 188174-23-4 (2-amino-4,5-dimethoxyphenyl)methanol 
• 220643-47-0 6-{1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl}-hex-5-ynoic acid 4,5-dimethoxy-2-nitro-benzyl ester 
• 42855-00-5 nitroveratryloxycarbonyl chloride 
• 302346-96-9 (4,5-dimethoxy-2-nitrophenyl)methyl O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)-O-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 185062-90-2 nitroveratryloxycarbonyl-4-(nitroveratrylcarboxy)phenylalanine t-butyl ester 
• 457612-04-3 succinic acid mono(4,5-dimethoxy-2-nitrobenzyl) ester 

Relevant articles and documents

Cascade photocaging of diazeniumdiolate: A novel strategy for one and two photon triggered uncaging with real time reporting

We report a new strategy, viz. cascade photocaging, for protecting diethylamine diazeniumdiolate (O2-position), a light sensitive molecule. Upon photolysis, the cascade photocage at first releases the light activatable linker (latent fluorophore) O2-caged diazeniumdiolate, which undergoes spontaneous 1,8-elimination, triggering the release of the diazeniumdiolate anion and the fluorophore.

Metal–Organic Framework-Encapsulated CoCu Nanoparticles for the Selective Transfer Hydrogenation of Nitrobenzaldehydes: Engineering Active Armor by the Half-Way Injection Method

A novel armor-type composite of metal–organic framework (MOF)-encapsulated CoCu nanoparticles with a Fe3O4 core (Fe3O4@SiO2-NH2-CoCu@UiO-66) has been designed and synthesized by the half-way injection method, which successfully serves as an efficient and recyclable catalyst for the selective transfer hydrogenation. In this half-way injection approach, the pre-synthetic Fe3O4@SiO2-NH2-CoCu was injected into the UiO-66 precursor solution halfway through the MOF budding period. The formed MOF armor could play a role of providing significant additional catalytic sites besides CoCu nanoparticles, protecting CoCu nanoparticles, and improving the catalyst stability, thus facilitating the selective transfer hydrogenation of nitrobenzaldehydes into corresponding nitrobenzyl alcohols in high selectivity (99 %) and conversion (99 %) rather than nitro group reduction products. Notably, this method achieves the precise assembly of a MOF-encapsulated composite, and the ingenious combination of MOF and nanoparticles exhibits excellent catalytic performance in the selective hydrogen transfer reaction, implementing a “1+1>2” strategy in catalysis.

Photocaged and Mixed Photocaged Bioreversible-Protected ATP Derivatives as Tools for the Controlled Release of ATP

Adenosine triphosphate (ATP) is known as the universal energy source for cellular processes, in addition, ATP also plays an important role in inflammation and cell signaling. Extracellular ATP binds to purinergic receptors and initiates further immune responses. To investigate these processes in-depth and to understand the complex mechanism of purinergic signaling, chemical tools are necessary. Here we present the synthesis of different photocaged ATP derivatives and the investigation of the light-induced release of ATP depending on the different synthesized photocleavable protecting groups based on the 2-nitrobenzyl moiety. Furthermore, we also present the synthesis of a mixed protected ATP-derivative as an example for a novel class of lipophilically caged nucleoside triphosphates. This new type of compounds is protected with a highly lipophilic non-toxic bio-removable acyloxybenzyl group and a photocleavable group. This combination may allow both passive cell uptake and controlled release of ATP by irradiation with non-harmful UV light.