Benzaldehyde, 4-(bromomethyl)-3-nitro-

Base Information

• Chemical Name: Benzaldehyde, 4-(bromomethyl)-3-nitro-
• CAS No.: 155526-65-1
• Molecular Formula: C8H6BrNO3
• Molecular Weight: 244.045
• DSSTox Substance ID: DTXSID50472233
• Wikidata: Q82301046
• Mol file: 155526-65-1.mol

Synonyms:Benzaldehyde, 4-(bromomethyl)-3-nitro-;155526-65-1;SCHEMBL6355056;DTXSID50472233

Chemical Property of Benzaldehyde, 4-(bromomethyl)-3-nitro-

Chemical Property:

• Melting Point: 74.5-75.5 °C(Solv: ethyl ether (60-29-7))
• Boiling Point: 344.0±32.0 °C(Predicted)
• PSA: 62.89000
• Density: 1.713±0.06 g/cm3(Predicted)
• LogP: 2.82540
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 242.95311
• Heavy Atom Count: 13
• Complexity: 204

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C=O)[N+](=O)[O-])CBr

Technology Process of Benzaldehyde, 4-(bromomethyl)-3-nitro-

There total 4 articles about Benzaldehyde, 4-(bromomethyl)-3-nitro- 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: 78.6%

4-(bromomethyl)benzaldehyde (51359-78-5) → 4-(bromomethyl)-3-nitrobenzaldehyde (155526-65-1)

Guidance literature:

With sulfuric acid; potassium nitrate; In chloroform; at 0 ℃; for 2.75h;

DOI:10.1002/ejoc.200700972

Reference yield:

terephthalaldehyde, (623-27-8) → 4-(bromomethyl)-3-nitrobenzaldehyde (155526-65-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 25.2 g / H₂ / 10percent Pd/C / ethanol; H₂O / 3 h / 760 Torr / Ambient temperature

2: 82 percent / 48percent aq. HBr / toluene / 2 h / Heating

3: 74 percent / KNO₃, H₂SO₄ / 4 h / Ambient temperature

With sulfuric acid; hydrogen bromide; hydrogen; potassium nitrate; palladium on activated charcoal; In ethanol; water; toluene;

DOI:10.1021/ja953578v

Reference yield:

4-(hydroxylmethyl)benzaldehyde (52010-97-6) → 4-(bromomethyl)-3-nitrobenzaldehyde (155526-65-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / 48percent aq. HBr / toluene / 2 h / Heating

2: 74 percent / KNO₃, H₂SO₄ / 4 h / Ambient temperature

With sulfuric acid; hydrogen bromide; potassium nitrate; In toluene;

DOI:10.1021/ja953578v

upstream raw materials:

4-(bromomethyl)benzaldehyde

4-cyanobenzyl bromide

terephthalaldehyde,

4-(hydroxylmethyl)benzaldehyde

Downstream raw materials:

2-{[2-(4-tert-Butoxy-3-tert-butoxycarbonylamino-butyl)-5-decyl-phenyl]-methyl-amino}-3-methyl-butyric acid 2,5-dioxo-pyrrolidin-1-yl ester

2-{[2-(2-tert-Butoxycarbonylamino-3-hydroxy-propyl)-5-decyl-phenyl]-methyl-amino}-3-methyl-butyric acid benzyl ester

Refernces

• 1、 Lin, Weiying,Peng, Daiwei,Wang, Bin,Long, Lingliang,Guo, Cancheng,Yuan, Jinbin. "A model for light-triggered porphyrin anticancer prodrugs based on an o-nitrobenzyl photolabile group". supporting information; experimental part. p. 793 - 796. Retrieved 2009/04/11.
• 2、 Endo, Yasuyuki,Ohno, Michihiro,Hirano, Masaaki,Itai, Akiko,Shudo, Koichi. "Synthesis, conformation, and biological activity of teleocidin mimics, benzolactams. A clarification of the conformational flexibility problem in structure-activity studies of teleocidins". . p. 1841 - 1855. Retrieved 2007/10/03.