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392847

Sigma-Aldrich

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:
1016-58-6
Molecular Weight:
213.19
Beilstein:
1880093
EC Number:
213-806-4
MDL number:
MFCD00014701
UNSPSC Code:
12352100
PubChem Substance ID:
24864489
NACRES:
NA.22

Assay

98%

mp

145-148 °C (lit.)

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:
  • 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
Alan R Katritzky et al.
The Journal of organic chemistry, 68(23), 9100-9104 (2003-11-08)
Molecules were prepared with substituted nitrobenzyl groups covalently bonded to N-(4-hydroxy-3-methoxybenzyl)acetamide (2) by ether or carbonate linkages. These compounds decomposed under irradiation at 363 nm. Those with carbonate linkages decomposed at slower rates than those with ether linkages. Molecules with
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)
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