392847
4,5-Dimethoxy-2-nitrobenzyl alcohol
98%
Synonym(s):
6-Nitroveratryl alcohol
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About This Item
Linear Formula:
O2NC6H2(OCH3)2CH2OH
CAS Number:
Molecular Weight:
213.19
Beilstein:
1880093
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Assay
98%
mp
145-148 °C (lit.)
functional group
hydroxyl
nitro
SMILES string
COc1cc(CO)c(cc1OC)[N+]([O-])=O
InChI
1S/C9H11NO5/c1-14-8-3-6(5-11)7(10(12)13)4-9(8)15-2/h3-4,11H,5H2,1-2H3
InChI key
WBSCOJBVYHQOFB-UHFFFAOYSA-N
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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).
Application
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:
It may be used in the synthesis of the following:
- 1-[[(chlorocarbonyl)oxy]methyl]-4,5-dimethoxy-2-nitrobenzene
- bis(4,5-dimethoxy-2-nitrophenyl)ethylene glycol, a photolabile protecting group
- optically-sensitive monomer
- nitroveratryl (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-phenylcarbonate
- 6-nitroveratryloxycarbonyl chloride (NVOCCl), a reagent used in the protection of amino function in amino sugars
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Andrew A Brown et al.
Langmuir : the ACS journal of surfaces and colloids, 25(3), 1744-1749 (2009-01-10)
The use of photolabile protecting groups (PGs) as a means to create latent hydrophilic surfaces is presented. Naturally hydrophobic PGs, based on o-nitrobenzyl chemistry, are used on polymer side chains, poised for cleavage upon exposure to UV light. Removal of
Peptide backbone mutagenesis of putative gating hinges in a potassium ion channel.
Yasuo Nagaoka et al.
Chembiochem : a European journal of chemical biology, 9(11), 1725-1728 (2008-06-11)
Novel photosensitive polyimide precursor based on polyisoimide using an amine photogenerator.
Mochizuki A, et al.
Macromolecules, 28(1), 365-369 (1995)
Photosensitive protecting groups of amino sugars and their use in glycoside synthesis. 2-nitrobenzyloxycarbonylamino and 6-nitroveratryloxycarbonylamino derivatives.
Amit B, et al.
The Journal of Organic Chemistry, 39(2), 192-196 (1974)
Nadezda Fomina et al.
Journal of the American Chemical Society, 132(28), 9540-9542 (2010-06-24)
A new light-sensitive polymer containing multiple light-sensitive triggering groups along the backbone and incorporating a quinone-methide self-immolative moiety was developed and formulated into nanoparticles encapsulating a model pharmaceutical Nile Red. Triggered burst release of the payload upon irradiation and subsequent
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