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

Chemical Properties

white to light yellow crystal powde

Uses

Different sources of media describe the Uses of 1016-58-6 differently. You can refer to the following data:
1. 4,5-Dimethoxy-2-nitrobenzyl alcohol, is used as Reagent for the protection of alcohols, etc., as ethers which can be cleaved by photolysis involving intramolecular rearrangement to derivatives of o-nitrosobenzaldehyde, which are readily cleaved by hydrolysis. It is also used as photochemical protecting groups in organic synthesis. It is also used as a pharmaceutical intermediate.
2. 4,5-Dimethoxy-2-nitrobenzyl alcohol (6-nitroveratryl alcohol) is 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.It may be used in the synthesis of the following:1-[[(chlorocarbonyl)oxy]methyl]-4,5-dimethoxy-2-nitrobenzenebis(4,5-dimethoxy-2-nitrophenyl)ethylene glycol, a photolabile protecting groupoptically-sensitive monomernitroveratryl (NV) protected α-hydroxyacetic acid (αG) (NV-αG-OH), required in the preparation of nitroveratryl (NV) protected cyanomethyl (CM) ester of α-hydroxyacetic acid (αG) (NV-αG-CM)4,5-dimethoxy-2-nitrobenzyl p-nitro-phenylcarbonate6-nitroveratryloxycarbonyl chloride (NVOCCl), a reagent used in the protection of amino function in amino sugars

General Description

4,5-Dimethoxy-2-nitrobenzyl alcohol (6-Nitroveratryl Alcohol) is 2-nitrobenzyl alcohol derivative. It has been reported to be one of the oxidation products of veratryl (3,4-dimethoxybenzyl) alcohol by lignin peroxidase (isolated from Phanerochaete chrysosporium).

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

Downstream Products

• 42855-00-5 nitroveratryloxycarbonyl chloride 
• 457612-05-4 glutaric acid mono-(4,5-dimethoxy-2-nitrobenzyl) ester 
• 188541-09-5 3-triethoxysilylpropyl-N-(4,5-dimethoxy-2-nitrobenzyloxycarbonyl)amine 
• 851597-72-3 4,5-dimethoxy-2-nitrobenzyl 2,3,5-tri-O-benzoyl-β-D-ribofuranoside 
• 1345834-32-3 4,5-dimethoxy-2-nitrobenzyl-N-succinimidyl carbonate 
• 1345834-30-1 (4,5-dimethoxy-2-nitrophenyl)methyl N-[(4-{[5-({4-[({[(4,5-dimethoxy-2-nitrophenyl)methoxy]carbonyl}amino)methanimidoyl]phenyl}amino)pentyl]amino}phenyl)carboximidoyl]carbamate 
• 1353745-56-8 4,5-dimethoxy-2-nitrobenzyl 2-(tert-butoxycarbonylamino)acetate 
• 123642-54-6 (4,5-dimethoxy-2-nitrophenyl)methyl 4butanoate 
• 165811-64-3 4,5-dimethoxy-2-nitrobenzyl 2-aminoacetate hydrochloride 
• 1331781-80-6 4,5-dimethoxy-2-nitrobenzyl 4-iodobenzoate 
• 1331781-81-7 4,5-dimethoxy-2-nitrobenzyl 4-trimethylsilylethynylbenzoate 
• 1331781-82-8 4,5-dimethoxy-2-nitrobenzyl 4-ethynylbenzoate 
• 1413643-96-5 4,5-dimethoxy-2-nitrobenzyl oleate 
• 1413644-53-7 4,5-dimethoxy-2-nitrobenzyl [methyl(oleoyl)amino]acetate 

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.