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420069

Sigma-Aldrich

4,5-Dimethoxy-2-nitrobenzyl chloroformate

97%, for peptide synthesis

Synonym(s):

6-Nitroveratryl chloroformate, 6-Nitroveratryloxycarbonyl chloride, NVOC chloride, NVOC-Cl

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About This Item

Linear Formula:
ClCO2CH2C6H2(OCH3)2NO2
CAS Number:
42855-00-5
Molecular Weight:
275.64
Beilstein/REAXYS Number:
2389168
MDL number:
MFCD00143507
UNSPSC Code:
12352101
PubChem Substance ID:
24866307
NACRES:
NA.22

product name

4,5-Dimethoxy-2-nitrobenzyl chloroformate, 97%

assay

97%

form

powder

mp

125 °C (dec.) (lit.)

application(s)

peptide synthesis

storage temp.

2-8°C

SMILES string

COc1cc(COC(Cl)=O)c(cc1OC)[N+]([O-])=O

InChI

1S/C10H10ClNO6/c1-16-8-3-6(5-18-10(11)13)7(12(14)15)4-9(8)17-2/h3-4H,5H2,1-2H3

InChI key

RWWPKIOWBQFXEE-UHFFFAOYSA-N

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Application

4,5-Dimethoxy-2-nitrobenzyl chloroformate (NVOC-Cl) is a photolabile protecting reagent, commonly used in peptide or nucleotide synthesis to protect amines and hydroxyl groups. General applications are:
  • Preparation of inactive, caged protein conjugates which can be activated by irradiating near-ultraviolet light.
  • Solid-phase synthesis of base-sensitive S-acylthioethyl (SATE)-prooligonucleotides.
  • Modification of surface properties by introducing photocleavable NVOC moiety into chitosan to control cell attachment.

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Description
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pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificates of Analysis (COA)

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Photoremovable protecting groups in organic synthesis.
Pillai V R
Synthesis, 1980(01), 1-26 (1980)
Photocleavable protecting groups as nucleobase protections allowed the solid-phase synthesis of base-sensitive SATE-prooligonucleotides.
Alvarez K, et al.
The Journal of Organic Chemistry, 64(17), 6319-6328 (1999)
A general and efficient route for chemical aminoacylation of transfer RNAs.
Robertson S A, et al.
Journal of the American Chemical Society, 113(7), 2722-2729 (1991)
Nan Cheng et al.
Journal of colloid and interface science, 361(1), 71-78 (2011-06-18)
An approach to control cell adhesion using a photocleavable molecule on chitosan has been developed and studied. Photocleavable 4,5-dimethoxy-2-nitrobenzyl chloroformate (NVOC) was introduced into chitosan to control the surface properties. The two UV illuminations with a photomask controlled the cleavage
Photolabile protecting groups for nucleosides: Synthesis and photodeprotection rates.
Hasan A, et al.
Tetrahedron, 53(12), 4247-4264 (1997)
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