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392847

Sigma-Aldrich

4,5-Dimethoxy-2-nitrobenzyl alcohol

98%

Sinonimo/i:

6-Nitroveratryl alcohol

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About This Item

Formula condensata:
O2NC6H2(OCH3)2CH2OH
Numero CAS:
1016-58-6
Peso molecolare:
213.19
Beilstein:
1880093
Numero CE:
213-806-4
Numero MDL:
MFCD00014701
Codice UNSPSC:
12352100
ID PubChem:
24864489
NACRES:
NA.22

Saggio

98%

Punto di fusione

145-148 °C (lit.)

Stringa SMILE

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
WBSCOJBVYHQOFB-UHFFFAOYSA-N

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Descrizione generale

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).

Applicazioni

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

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

Certificati d'analisi (COA)

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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
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)
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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Chembiochem : a European journal of chemical biology, 11(5), 653-663 (2010-02-27)
We have implemented a noninvasive optical method for the fast control of protein activity in a live zebrafish embryo. It relies on releasing a protein fused to a modified estrogen receptor ligand binding domain from its complex with cytoplasmic chaperones
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