3-Chloromethyl-5-nitrosalicylaldehyde

Base Information

• Chemical Name: 3-Chloromethyl-5-nitrosalicylaldehyde
• CAS No.: 16644-30-7
• Molecular Formula: C8H6 Cl N O4
• Molecular Weight: 215.593
• NSC Number: 221280
• UNII: ZX3AXU63T2
• DSSTox Substance ID: DTXSID10168105
• Wikidata: Q72454436
• Mol file: 16644-30-7.mol

Synonyms:3-Chloromethyl-5-nitrosalicylaldehyde;16644-30-7;3-(chloromethyl)-2-hydroxy-5-nitrobenzaldehyde;Salicylaldehyde, 3-chloromethyl-5-nitro-;Benzaldehyde, 3-(chloromethyl)-2-hydroxy-5-nitro-;NSC 221280;BRN 1879465;MFCD00191331;NSC-221280;NSC221280;3-(Chloromethyl)-5-nitrosalicylaldehyde;ZX3AXU63T2;WLN: WNR DQ CVH E1G;SCHEMBL4349087;DTXSID10168105;AMY20708;AKOS022181158;AS-10149;SY112080;2,3-Cresotaldehyde, alpha-chloro-5-nitro-;LS-144125;FT-0637392;2-Hydroxy-3-(chloromethyl)-5-nitrobenzaldehyde;3-(chloromethyl)-2-hydroxy-5-nitro-benzaldehyde;A810738

Chemical Property of 3-Chloromethyl-5-nitrosalicylaldehyde

Chemical Property:

• Vapor Pressure: 4.37E-06mmHg at 25°C
• Melting Point: 92°C
• Boiling Point: 372.8°Cat760mmHg
• PKA: 4.37±0.50(Predicted)
• Flash Point: 179.3°C
• Density: 1.55g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 214.9985354
• Heavy Atom Count: 14
• Complexity: 230

Purity/Quality:

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

3-Chloromethyl-5-nitrosalicylaldehyde ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C=C(C(=C1CCl)O)C=O)[N+](=O)[O-]

Technology Process of 3-Chloromethyl-5-nitrosalicylaldehyde

There total 4 articles about 3-Chloromethyl-5-nitrosalicylaldehyde 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: 80.0%

5-Nitrosalicylaldehyde (97-51-8) → 3-(chloromethyl)-2-hydroxy-5-nitrobenzaldehyde (16644-30-7)

Guidance literature:

aluminium trichloride; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; chloromethyl methyl ether;

Reference yield: 78.0%

chloromethyl methyl ether (107-30-2) + 5-Nitrosalicylaldehyde (97-51-8) → 3-(chloromethyl)-2-hydroxy-5-nitrobenzaldehyde (16644-30-7)

Guidance literature:

With aluminum (III) chloride; for 3h; Inert atmosphere; Reflux;

DOI:10.1039/c9tb02733e

Reference yield:

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) → 3-(chloromethyl)-2-hydroxy-5-nitrobenzaldehyde (16644-30-7)

Guidance literature:

Multi-step reaction with 2 steps

1: various solvent(s)

2: 71 percent / AlCl₃

With aluminium trichloride; In various solvent(s);

DOI:10.1002/ejoc.200500681

upstream raw materials:

chloromethyl methyl ether

5-Nitrosalicylaldehyde

4-nitro-phenol

Downstream raw materials:

3-methacryloxymethyl-5-nitrothiosalicylaldehyde

3-methacryloxymethyl-2-S-(N,N-dimethylthiocarbamoyl)-5-nitrosalicylaldehyde

3-methacryloxymethyl-2-O-(N,N-dimethylthiocarbamoyl)-5-nitrosalicylaldehyde

C₁₆H₂₅N₅O₄

Refernces

• 1、 Ajiro, Hiroharu,Ando, Tsuyoshi,Murase, Nobuo. "Synthesis of spiropyran with methacrylate at the benzopyran moiety and control of the water repellency and cell adhesion of its polymer film". . p. 1489 - 1495. Retrieved 2020/03/06.
• 2、 Roxburgh, Craig J.,Sammes, Peter G.. "Synthesis of some new substituted photochromic N,N′-bis(spiro[1- benzopyran-2,2′-indolyl])diazacrown systems with substituent control over ion chelation". . p. 1050 - 1056. Retrieved 2007/10/03.