Skip to Content
Merck
All Photos(2)

Key Documents

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

Sign Into View Organizational & Contract Pricing


About This Item

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

Pricing and availability is not currently available.

Product Name

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

Quality Level

assay

97%

form

powder

mp

125 °C (dec.) (lit.)

application(s)

peptide synthesis

functional group

chloro
nitro

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

Looking for similar products? Visit Product Comparison Guide

Compare Similar Items

View Full Comparison

Show Differences

1 of 4

This Item
663956778001694274
technique(s)

bio NMR: suitable

technique(s)

bio NMR: suitable

technique(s)

bio NMR: suitable

technique(s)

bio NMR: suitable

assay

95% (CP)

assay

97% (CP)

assay

97% (CP)

assay

97% (CP)

isotopic purity

99 atom % 13C, 98 atom % 15N

isotopic purity

98 atom % 13C, 98 atom % 15N

isotopic purity

99 atom % 13C, 98 atom % 15N

isotopic purity

99 atom % 13C, 98 atom % 15N

form

solid

form

solid

form

solid

form

solid

storage temp.

−20°C

storage temp.

−20°C

storage temp.

-

storage temp.

2-8°C

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.[1][2][3] General applications are:
  • Preparation of inactive, caged protein conjugates which can be activated by irradiating near-ultraviolet light.[4]
  • Solid-phase synthesis of base-sensitive S-acylthioethyl (SATE)-prooligonucleotides.[5]
  • Modification of surface properties by introducing photocleavable NVOC moiety into chitosan to control cell attachment.[6]

related product

Product No.
Description
Pricing

pictograms

Corrosion

signalword

Danger

hcodes

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


  • Choose from one of the most recent versions:

    Certificates of Analysis (COA)

    Lot/Batch Number

    Don't see the Right Version?

    If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

    Already Own This Product?

    Find documentation for the products that you have recently purchased in the Document Library.

    Visit the Document Library

    Customers Also Viewed

    Photolabile protecting groups for nucleosides: Synthesis and photodeprotection rates.
    Hasan A, et al.
    Tetrahedron, 53(12), 4247-4264 (1997)
    Photoremovable protecting groups in organic synthesis.
    Pillai V R
    Synthesis, 1980(01), 1-26 (1980)
    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)
    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)
    P Roy et al.
    The Journal of cell biology, 153(5), 1035-1048 (2001-05-31)
    The broad aim of this work was to explore the feasibility of using light-directed perturbation techniques to study cell locomotion. Specifically, a caged form of thymosin beta4 (Tbeta4) was photoactivated in a defined local region of locomoting fish scale keratocytes

    Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

    Contact Technical Service