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).[1]
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[2] and 2-(4-((4-(4,5-dimethoxy-2-nitrobenzyloxy)phenyl)cyclohexylidene)methyl)phenoxy)-N,N-dimethylethanamine, a caged cyclofen-OH ligand.[3]
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[4]
- bis(4,5-dimethoxy-2-nitrophenyl)ethylene glycol, a photolabile protecting group[5]
- optically-sensitive monomer[6]
- 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)[7]
- 4,5-dimethoxy-2-nitrobenzyl p-nitro-phenylcarbonate[8]
- 6-nitroveratryloxycarbonyl chloride (NVOCCl), a reagent used in the protection of amino function in amino sugars[9]
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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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
Bis (4, 5-dimethoxy-2-nitrophenyl) ethylene glycol: a new and efficient photolabile protecting group for aldehydes and ketones.
Kantevari S, et al.
Tetrahedron, 61(24), 5849-5854 (2005)
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)
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
Novel photosensitive polyimide precursor based on polyisoimide using an amine photogenerator.
Mochizuki A, et al.
Macromolecules, 28(1), 365-369 (1995)
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