4,5-Dimethoxy-2-nitrobenzyl carbonochloridate

Base Information

• Chemical Name: 4,5-Dimethoxy-2-nitrobenzyl carbonochloridate
• CAS No.: 42855-00-5
• Molecular Formula: C10H10ClNO6
• Molecular Weight: 275.645
• Hs Code.: 2918999090
• European Community (EC) Number: 628-811-0
• DSSTox Substance ID: DTXSID70195538
• Nikkaji Number: J1.622.316F
• Wikidata: Q83068514
• Mol file: 42855-00-5.mol

Synonyms:((nitroveratryl)oxy)chlorocarbamate;NVOC-Cl

Chemical Property of 4,5-Dimethoxy-2-nitrobenzyl carbonochloridate

Chemical Property:

• Appearance/Colour: UN 3261 8/PG 2
• Vapor Pressure: 1.72E-06mmHg at 25°C
• Melting Point: 125 °C (dec.)(lit.)
• Refractive Index: 1.545
• Boiling Point: 396.4 °C at 760 mmHg
• Flash Point: 193.5 °C
• PSA: 90.58000
• Density: 1.399 g/cm³
• LogP: 3.01060
• Storage Temp.: 2-8°C
• Sensitive.: Moisture & Light Sensitive
• Water Solubility.: Soluble in methanol, acetone. Reacts with water.
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 275.0196647
• Heavy Atom Count: 18
• Complexity: 307

Purity/Quality:

98%,99%, ^*data from raw suppliers

4,5-Dimethoxy-2-nitrobenzylCarbonochloridate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-37
• Safety Statements: 26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=C(C=C(C(=C1)COC(=O)Cl)[N+](=O)[O-])OC
• Uses: 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. 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.

Technology Process of 4,5-Dimethoxy-2-nitrobenzyl carbonochloridate

There total 4 articles about 4,5-Dimethoxy-2-nitrobenzyl carbonochloridate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

phosgene (75-44-5) + 6-nitroveratryl alcohol (1016-58-6) → nitroveratryloxycarbonyl chloride (42855-00-5)

Guidance literature:

In tetrahydrofuran; toluene; at 0 ℃; for 4h;

DOI:10.1002/(SICI)1522-2675(19990609)82:6<888::AID-HLCA888>3.0.CO;2-5

Reference yield: 74.0%

bis(trichloromethyl) carbonate (32315-10-9) + 6-nitroveratryl alcohol (1016-58-6) → nitroveratryloxycarbonyl chloride (42855-00-5)

Guidance literature:

With pyridine; In dichloromethane; for 0.166667h;

Reference yield:

6-nitroveratryl alcohol (1016-58-6) → nitroveratryloxycarbonyl chloride (42855-00-5)

Guidance literature:

With bis(trichloromethyl) carbonate; In dichloromethane; at 0 - 20 ℃; for 12h; Inert atmosphere;

DOI:10.1021/acs.joc.5b01668

upstream raw materials:

phosgene

6-nitroveratryl alcohol

bis(trichloromethyl) carbonate

Downstream raw materials:

(S)-2-(4,5-Dimethoxy-2-nitro-benzyloxycarbonylamino)-3-(5-hydroxy-1H-indol-3-yl)-propionic acid

C₁₈H₂₆N₂O₈S₂

Refernces

• 1、 Duttagupta, Indranil,Misra, Debojyoti,Bhunya, Sourav,Paul, Ankan,Sinha, Surajit. "Cis-Trans Conformational Analysis of δ-Azaproline in Peptides". . p. 10585 - 10604. Retrieved 2015/11/18.
• 2、 Shin, Dong-Sik,Lee, Yoon-Sik. "Synthesis of pentafluorophenyl esters of nitroveratryloxycarbonyl-protected amino acids". experimental part. p. 3307 - 3310. Retrieved 2010/03/05.