4,5-Dimethoxy-2-nitrobenzyl alcohol

Base Information

• Chemical Name: 4,5-Dimethoxy-2-nitrobenzyl alcohol
• CAS No.: 1016-58-6
• Molecular Formula: C9H11NO5
• Molecular Weight: 213.19
• Hs Code.: 29094990
• European Community (EC) Number: 213-806-4
• DSSTox Substance ID: DTXSID50144044
• Nikkaji Number: J217.140F
• Wikidata: Q72468144
• Mol file: 1016-58-6.mol

Synonyms:4,5-Dimethoxy-2-nitrobenzyl alcohol;1016-58-6;6-Nitroveratryl alcohol;(4,5-dimethoxy-2-nitrophenyl)methanol;Benzenemethanol, 4,5-dimethoxy-2-nitro-;EINECS 213-806-4;2-nitro-4,5-dimethoxybenzyl alcohol;4,5-Dimethoxy-2-nitrobenzenemethanol;MFCD00014701;3,4-Dimethoxy-6-nitrobenzyl alcohol;6-nitroveratrylalcohol;SCHEMBL67755;DTXSID50144044;AMY41415;BCP11712;4,5-dimethoxy 2-nitrobenzyl alcohol;AKOS009116292;AC-26188;AS-15876;SY069707;4,5-Dimethoxy-2-nitrobenzyl alcohol, 98%;CS-0104904;D4811;FT-0617191;A22392;EN300-1841144;J-000464

Chemical Property of 4,5-Dimethoxy-2-nitrobenzyl alcohol

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 1.4E-06mmHg at 25°C
• Melting Point: 145-148 °C(lit.)
• Refractive Index: 1.558
• Boiling Point: 383.9 °C at 760 mmHg
• PKA: 13.59±0.10(Predicted)
• Flash Point: 186 °C
• PSA: 84.51000
• Density: 1.307 g/cm³
• LogP: 1.62750
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive.: Light Sensitive
• Water Solubility.: Soluble in water.
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 213.06372245
• Heavy Atom Count: 15
• Complexity: 217

Purity/Quality:

98%,99%, ^*data from raw suppliers

4,5-Dimethoxy-2-nitrobenzyl Alcohol ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Aromatics (Nitrogen)
• Canonical SMILES: COC1=C(C=C(C(=C1)CO)[N+](=O)[O-])OC
• Uses: 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. 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

Technology Process of 4,5-Dimethoxy-2-nitrobenzyl alcohol

There total 7 articles about 4,5-Dimethoxy-2-nitrobenzyl alcohol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

6-nitroveratraldehyde (20357-25-9) → 6-nitroveratryl alcohol (1016-58-6)

Guidance literature:

With sodium tetrahydroborate; In methanol; dichloromethane; at 0 - 20 ℃; for 12h;

DOI:10.1016/j.ejmech.2016.03.049

Reference yield:

(3,4-dimethoxyphenyl)methanol (93-03-8) → 6-nitroveratryl alcohol (1016-58-6)

Guidance literature:

With nitric acid; acetic anhydride; at 0 - 20 ℃; for 6h;

Reference yield:

vanillin (121-33-5,8014-42-4) → 6-nitroveratryl alcohol (1016-58-6)

Guidance literature:

Multi-step reaction with 3 steps

1: potassium carbonate / acetone / 17 h / Reflux

2: nitric acid / 2 h / 0 - 20 °C

3: sodium tetrahydroborate / ethanol / 4 h / 20 °C

With sodium tetrahydroborate; nitric acid; potassium carbonate; In ethanol; acetone;

DOI:10.1039/c7cc04635a

upstream raw materials:

6-nitroveratraldehyde

4,5-dimethoxy-2-nitrobenzyl 2-aminoacetate hydrochloride

C₂₄H₃₁N₃O₁₀

vanillin

Downstream raw materials:

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

nitroveratryloxycarbonyl chloride

succinic acid mono(4,5-dimethoxy-2-nitrobenzyl) ester

diisopropyl-phosphoramidous acid tert-butyl ester 4,5-dimethoxy-2-nitro-benzyl ester

Refernces

• 1、 Matinkhoo, Kaveh,Pryyma, Alla,Wong, Antonio A. W. L.,Perrin, David M.. "Synthesis and evaluation of “Ama-Flash”, a photocaged amatoxin prodrug for light-activated RNA Pol II inhibition and cell death". . p. 9558 - 9561. Retrieved 2021.
• 2、 Da Costa, Laurène,Roche, Manon,Scheers, Els,Coluccia, Antonio,Neyts, Johan,Terme, Thierry,Leyssen, Pieter,Silvestri, Romano,Vanelle, Patrice. "VP1 crystal structure-guided exploration and optimization of 4,5-dimethoxybenzene-based inhibitors of rhinovirus 14 infection". . p. 453 - 462. Retrieved 2016.