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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:
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

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

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.

related product

Product No.
Description
Pricing

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ2277
BCCG4682
BCCG0201
BCBG8412V
1451721

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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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