2-(4-Nitrophenyl)-4,5-dihydro-1,3-thiazole

Base Information

• Chemical Name: 2-(4-Nitrophenyl)-4,5-dihydro-1,3-thiazole
• CAS No.: 2518-13-0
• Molecular Formula: C9H8 N2 O2 S
• Molecular Weight: 208.241
• NSC Number: 159304
• DSSTox Substance ID: DTXSID20303606
• Nikkaji Number: J424.046D
• Wikidata: Q82048973
• Mol file: 2518-13-0.mol

Synonyms:2-(4-nitrophenyl)-4,5-dihydro-1,3-thiazole;2518-13-0;2-{4-nitrophenyl}-4,5-dihydro-1,3-thiazole;thiazole, 4,5-dihydro-2-(4-nitrophenyl)-;NSC159304;SCHEMBL5778004;DTXSID20303606;MJKNSOPAEQZIEG-UHFFFAOYSA-N;AKOS024328759;NSC-159304;2-(4-Nitrophenyl)-4,5-dihydrothiazole;AL-182/11625010

Chemical Property of 2-(4-Nitrophenyl)-4,5-dihydro-1,3-thiazole

Chemical Property:

• Vapor Pressure: 1.95E-05mmHg at 25°C
• Boiling Point: 373.2°Cat760mmHg
• Flash Point: 179.5°C
• Density: 1.43g/cm³
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 208.03064868
• Heavy Atom Count: 14
• Complexity: 254

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CSC(=N1)C2=CC=C(C=C2)[N+](=O)[O-]

Technology Process of 2-(4-Nitrophenyl)-4,5-dihydro-1,3-thiazole

There total 15 articles about 2-(4-Nitrophenyl)-4,5-dihydro-1,3-thiazole 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: 94.0%

2-mercaptoethylamine hydrochloride (156-57-0) + 1H-1,2,3-benzotriazol-1-yl-4-nitrophenylmethanone (4231-71-4) → 2-(4-nitrophenyl)-4,5-dihydro-1,3-thiazole (2518-13-0)

Guidance literature:

2-mercaptoethylamine hydrochloride; 1H-1,2,3-benzotriazol-1-yl-4-nitrophenylmethanone; With triethylamine; In chloroform; at 80 ℃; for 0.166667h; under 206.859 - 517.148 Torr; microwave irradiation;

With thionyl chloride; In chloroform; at 80 ℃; for 0.0333333h; microwave irradiation;

DOI:10.1021/jo0355092

Reference yield: 92.0%

Cysteamine (60-23-1) + 4-nitrobenzonitrile (619-72-7) → 2-(4-nitrophenyl)-4,5-dihydro-1,3-thiazole (2518-13-0)

Guidance literature:

With 1-butyl-3-methylimidazolium tribromide; at 100 ℃; for 0.0666667h;

DOI:10.1080/10426507.2011.618816

Reference yield: 90.0%

2-mercaptoethylamine hydrochloride (156-57-0) + 4-nitrobenzonitrile (619-72-7) → 2-(4-nitrophenyl)-4,5-dihydro-1,3-thiazole (2518-13-0)

Guidance literature:

With tetrakis(μ2-α-methacrylate-O,O')-bis(H2O)-dicopper(II); sodium acetate; at 80 ℃; for 5h; Neat (no solvent);

DOI:10.1002/ejoc.201101786

upstream raw materials:

4-nitro-benzoic acid-(2-bromo-ethylamide)

4-nitrobenzimidic acid methyl ester

2-mercaptoethylamine hydrochloride

1H-1,2,3-benzotriazol-1-yl-4-nitrophenylmethanone

Downstream raw materials:

4-(4,5-dihydrothiazol-2-yl)aniline

2-(4-nitrophenyl)thiazole

5-(4-nitro-phenyl)-6-(toluene-4-sulfonyloxy)-4-thia-1-aza-bicyclo[3.2.0]heptan-7-one

Refernces

• 1、 Zarei, Zeinab,Akhlaghinia, Batool. "Cu(II) immobilized on Fe3O4@Agarose nanomagnetic catalyst functionalized with ethanolamine phosphate–salicylaldehyde schiff base: A magnetically reusable nanocatalyst for preparation of 2-substituted imidazolines, oxazolines, and thiazolines". . p. 170 - 191. Retrieved 2018/02/17.
• 2、 Li, Xiangnan,Li, Cheng,Yin, Bing,Li, Cong,Liu, Ping,Li, Jianli,Shi, Zhen. "DDQ-induced dehydrogenation of heterocycles for c-c double bond formation: Synthesis of 2-thiazoles and 2-oxazoles". supporting information. p. 1408 - 1411. Retrieved 2013/07/26.