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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:
Molecular Weight:
213.19
Beilstein:
1880093
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

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:
  • 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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