4-nitro-2-[(E)-2'-(1'',3'',3''-trimethyl-3H'''-2''-indoliumyl)-1'-ethenyl]-1-phenolate

Base Information

• Chemical Name: 4-nitro-2-[(E)-2'-(1'',3'',3''-trimethyl-3H'''-2''-indoliumyl)-1'-ethenyl]-1-phenolate
• CAS No.: 18457-95-9
• Molecular Formula: C₁₉H₁₈N₂O₃
• Molecular Weight: 322.364
• Mol file: 18457-95-9.mol

Synonyms:4-nitro-2-[(E)-2'-(1'',3'',3''-trimethyl-3H'''-2''-indoliumyl)-1'-ethenyl]-1-phenolate

Chemical Property of 4-nitro-2-[(E)-2'-(1'',3'',3''-trimethyl-3H'''-2''-indoliumyl)-1'-ethenyl]-1-phenolate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-nitro-2-[(E)-2'-(1'',3'',3''-trimethyl-3H'''-2''-indoliumyl)-1'-ethenyl]-1-phenolate

There total 12 articles about 4-nitro-2-[(E)-2'-(1'',3'',3''-trimethyl-3H'''-2''-indoliumyl)-1'-ethenyl]-1-phenolate 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:

1,3',3'-trimethyl-6-nitrospiro(indoline-2,2'-[2H]benzopyran) (1498-88-0) → 4-nitro-2-[(E)-2'-(1'',3'',3''-trimethyl-3H'''-2''-indoliumyl)-1'-ethenyl]-1-phenolate (18457-95-9)

Guidance literature:

In dimethyl sulfoxide; at 25 ℃; Thermodynamic data; Equilibrium constant; ΔG, ΔS, ΔH;

DOI:10.1021/ja00241a052

Reference yield:

2,3,3-trimethylindoleniune (1640-39-7) → 4-nitro-2-[(E)-2'-(1'',3'',3''-trimethyl-3H'''-2''-indoliumyl)-1'-ethenyl]-1-phenolate (18457-95-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: acetonitrile / 3 h / Reflux; Inert atmosphere

2.1: potassium hydroxide / water / 0.17 h / 20 °C

2.2: 15 h / 20 °C / Reflux; Inert atmosphere

3.1: methanol; water / 0.83 h / 45 °C / UV-irradiation

With potassium hydroxide; In methanol; water; acetonitrile;

DOI:10.1039/c0cp00140f

Reference yield:

1,2,3,3-tetramethyl-3H-indolium iodide (5418-63-3) → 4-nitro-2-[(E)-2'-(1'',3'',3''-trimethyl-3H'''-2''-indoliumyl)-1'-ethenyl]-1-phenolate (18457-95-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium hydroxide / water / 0.17 h / 20 °C

1.2: 15 h / 20 °C / Reflux; Inert atmosphere

2.1: methanol; water / 0.83 h / 45 °C / UV-irradiation

With potassium hydroxide; In methanol; water;

DOI:10.1039/c0cp00140f

upstream raw materials:

1,3',3'-trimethyl-6-nitrospiro(indoline-2,2'-[2H]benzopyran)

merocyanine

1’,3’-dihydro-1’,3’,3’-trimethyl-6-nitrospiro[2H-1-benzopyran-2,2’-(2H)-indole]

2,3,3-trimethylindoleniune

Downstream raw materials:

1,3',3'-trimethyl-6-nitrospiro(indoline-2,2'-[2H]benzopyran)

1’,3’-dihydro-1’,3’,3’-trimethyl-6-nitrospiro[2H-1-benzopyran-2,2’-(2H)-indole]

Refernces

• 1、 Zhi,Baba,Hashimoto,Fujishima. "Multi-functional electro-optical molecular device. The photoelectrochemical behavior of spirobenzopyrans in dimethylformamide". . p. 32 - 39. Retrieved 1995.
• 2、 Drummond, Calum J.,Furlong, D. Neil. "Photochromism of a Surface-active Spirobenzopyran Moiety in Dioxane-Water Mixtures and Self-assembled Surfactant Aggregates". . p. 3613 - 3621. Retrieved 1990.
• 3、 Sato, Hiroyasu,Matsuzaki, Akiyoshi,Nishio, Satoru,Yoshimi, Motohiro,Yamamoto, Katsutoshi,Tomioka, Hideo. "A Raman spectroscopic study of merocyanine aggregates of a 15N-isotopomer of 6-Nitro-1′,3′,3′-trimethylspiro[2H-1-benzopyran-2,2′- indoline]. A direct evidence for the association through the NO2-bridges". . p. 715 - 716. Retrieved 1996.
• 4、 Kortekaas,Chen,Jacquemin,Browne. "Proton-Stabilized Photochemically Reversible E/ Z Isomerization of Spiropyrans". . p. 6423 - 6430. Retrieved 2018/06/08.
• 5、 Rogers, Robert A.,Rodier, Allison R.,Stanley, Jake A.,Douglas, Nick A.,Li, Xiaopeng,Brittain, William J.. "A study of the spiropyran-merocyanine system using ion mobility-mass spectrometry: Experimental support for the cisoid conformation". supporting information. p. 3424 - 3426. Retrieved 2014/03/21.