42855-00-5

Basic information

• Product Name: 6-NITROVERATRYL CHLOROFORMATE
• Synonyms: NVOC CHLORIDE;NVOC-CL;6-NITROVERATRYL CHLOROFORMATE;6-NITROVERATRYLOXYCARBONYL CHLORIDE;4,5-DIMETHOXY-2-NITROBENZYL CHLOROFORMATE;Chloroformic acid 6-nitroveratryl ester~4,5-Dimethoxy-2-nitrobenzyl chloroformate~NVOC-Cl;4,5-Dimethoxy-2-nitrobenzylchloroformate~NVOC-Cl;Chloroformicacid6-nitroveratrylester
• CAS NO: 42855-00-5
• Molecular Formula: C₁₀H₁₀ClNO₆
• Molecular Weight: 275.64
• Mol File: 42855-00-5.mol
• Article Data: 7

Chemical Properties

• Melting Point: 125 °C (dec.)(lit.)
• Boiling Point: 396.4 °C at 760 mmHg
• Flash Point: 193.5 °C
• Appearance: UN 3261 8/PG 2
• Density: 1.399 g/cm³
• Vapor Pressure: 1.72E-06mmHg at 25°C
• Refractive Index: 1.545
• Storage Temp.: 2-8°C
• Water Solubility: Soluble in methanol, acetone. Reacts with water.
• Sensitive: Moisture & Light Sensitive
• BRN: 2389168
• CAS DataBase Reference: 6-NITROVERATRYL CHLOROFORMATE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-NITROVERATRYL CHLOROFORMATE(42855-00-5)
• EPA Substance Registry System: 6-NITROVERATRYL CHLOROFORMATE(42855-00-5)

Safety Data

• Hazard Codes: C
• Statements: 34-37
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 10-21
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 42855-00-5(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 42855-00-5 differently. You can refer to the following data:
1. 4,5-Dimethoxy-2-nitrobenzyl chloroformate is used as a reagent for protection of amines, for use in N-protection of bases in nucleotide synthesis, photochemical protecting groups in organic synthesis. It is used as pharmaceutical intermediate.
2. 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.

InChI:InChI=1/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

Upstream product

• 75-44-5 phosgene 
• 1016-58-6 6-nitroveratryl alcohol 
• 32315-10-9 bis(trichloromethyl) carbonate 

Downstream Products

• 217176-96-0 N-<(4,5-dimethoxy-2-nitrobenzyloxy)carbonyl>-L-isoleucine 
• 869318-01-4 (S)-2-(4,5-Dimethoxy-2-nitro-benzyloxycarbonylamino)-3-(4-hydroxy-phenyl)-propionic acid cyanomethyl ester 
• 935458-06-3 N-(6-nitroveratryloxycarbonyl)-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(S)-tyrosine cyanomethyl ester 
• 935457-98-0 N-(6-nitroveratryloxycarbonyl)-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(S)-tyrosine cyanomethyl ester 
• 243657-07-0 6-N-(6-nitroveratryloxycarbonyl)-2'-deoxyadenosine 
• 135997-57-8 α-NVOC-tyrosine 
• 864288-93-7 [2-(4,5-dimethoxy-2-nitro-benzyloxycarbonylamino)-ethylamino]-acetic acid tert-butyl ester 

Relevant articles and documents

Oligonucleotide promoted peptide bond formation using a tRNA mimicking approach

TransferRNA's role in protein translation is the prime example of an Informational Leaving Group (ILG). A simplified model produced oligophenylalanine with a modified uracil as an ILG in the presence of specific oligonucleotides. Our preliminary studies contribute to the importance of hybrid species in bridging the gap between peptides and nucleic acids.

NOVEL SEMI-SYNTHETIC GLYCOPEPTIDES AS ANTIBACTERIAL AGENTS

Semi-synthetic glycopeptides having antibacterial activity are described, in particular, the semi-synthetic glycopeptides described herein are made by chemical modification of the a glycopeptide (Compound A, Compound B, Compound H or Compound C) or the monosaccharide made by hydrolyzing the disaccharide moiety of the amino acid-4 of the parent glycopeptide in acidic medium to give the amino acid-4 monosaccharide; conversion of the monosaccharide to the amino-sugar derivative; acylation of the amino substituent on the amino acid-4 amino-substituted sugar moiety on these scaffolds with certain acyl groups; conversion of the amide group in amino acid-3 on these scaffolds to various acylamide, acylsulfonamide, acylsulfonylurea derivatives; aminomethylation with substituent containing sulfonamide or acylsulfonamide group on amino acid-7 through Mannich reaction; and conversion of the acid moiety on the macrocyclic ring of these scaffolds to certain substituted amides. Also provided are methods for the synthesis of the compounds, pharmaceutical compositions containing the compounds, and methods of use of the compounds for the treatment and/or prophylaxis of diseases, especially bacterial infections.

Model Compounds of Caged Capsaicin: Design, Synthesis, and Photoreactivity

Molecules were prepared with substituted nitrobenzyl groups covalently bonded to N-(4-hydroxy-3-methoxybenzyl)acetamide (2) by ether or carbonate linkages. These compounds decomposed under irradiation at 363 nm. Those with carbonate linkages decomposed at