2-Chloro-1-(4-nitrophenyl)ethanol

Base Information

• Chemical Name: 2-Chloro-1-(4-nitrophenyl)ethanol
• CAS No.: 13407-16-4
• Molecular Formula: C8H8 Cl N O3
• Molecular Weight: 201.609
• Hs Code.: 2906299090
• DSSTox Substance ID: DTXSID00401614
• Nikkaji Number: J2.242.447E
• Mol file: 13407-16-4.mol

Synonyms:2-chloro-1-(4-nitrophenyl)ethanol;13407-16-4;Benzenemethanol, alpha-(chloromethyl)-4-nitro- (9CI);alpha-Chloromethyl-4-nitrobenzenemethanol;2-chloro-1-(4-nitrophenyl)ethan-1-ol;p-nitrophenylchloromethylcarbinol;SCHEMBL1108434;DTXSID00401614;AKOS005374676;EN300-1964945

Chemical Property of 2-Chloro-1-(4-nitrophenyl)ethanol

Chemical Property:

• PSA: 66.05000
• LogP: 2.39020
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 201.0192708
• Heavy Atom Count: 13
• Complexity: 175

Purity/Quality:

99% ^*data from raw suppliers

α-Chloromethyl-4-nitrobenzenemethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(CCl)O)[N+](=O)[O-]
• Uses: α-Chloromethyl-4-nitrobenzenemethanol is a reagent used in the synthesis of monocyclic nitroimidazole analogs of econazole which have antitubercular activity.

Technology Process of 2-Chloro-1-(4-nitrophenyl)ethanol

There total 7 articles about 2-Chloro-1-(4-nitrophenyl)ethanol 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: 86.0%

Chloroiodomethane (593-71-5) + 4-nitrobenzaldehdye (555-16-8) → α-(chloromethyl)-4-nitrobenzyl alcohol (13407-16-4,216160-44-0)

Guidance literature:

Chloroiodomethane; With TurboGrignard; In tetrahydrofuran; at -78 ℃; for 0.166667h; Inert atmosphere;

4-nitrobenzaldehdye; In tetrahydrofuran; at -78 - 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.tetlet.2012.10.132

Reference yield: 74.0%

p-Nitrophenyloxirane (6388-74-5,38201-14-8,71884-55-4) → α-(chloromethyl)-4-nitrobenzyl alcohol (13407-16-4,216160-44-0)

Guidance literature:

With lithium chloride; copper dichloride; In tetrahydrofuran; at 20 ℃; Inert atmosphere;

DOI:10.1021/ja805128x

Reference yield:

2-chloro-1-(4-nitrophenyl)ethanone (34006-49-0) → α-(chloromethyl)-4-nitrobenzyl alcohol (13407-16-4,216160-44-0)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 20 ℃;

DOI:10.1021/jo802350f

upstream raw materials:

hydrogenchloride

2-bromo-1-(4-nitro-phenyl)-1-nitryloxy-ethane

p-Nitrophenyloxirane

2-chloro-1-(4-nitrophenyl)ethanone

Downstream raw materials:

(S)-2-chloro-1-(4-nitrophenyl)ethanol

(R)-2-chloro-1-(4-nitrophenyl)ethanol

2-(2-methoxy-4-nitro-1H-imidazol-1-yl)-1-(4-nitrophenyl)ethanol

2-(2-bromo-4-nitro-1H-imidazol-1-yl)-1-(4-nitrophenyl)ethanol

Refernces

• 1、 Von Keutz, Timo,Cantillo, David,Kappe, C. Oliver. "Organomagnesium Based Flash Chemistry: Continuous Flow Generation and Utilization of Halomethylmagnesium Intermediates". supporting information. p. 7537 - 7541. Retrieved 2020/10/12.
• 2、 Nishimura, Rodolfo H.V.,Toledo, Fabiano T.,Lopes, Jo?o L.C.,Clososki, Giuliano C.. "Efficient synthesis of chlorohydrins using ClCH2MgCl·LiCl". . p. 287 - 290. Retrieved 2013/02/23.