3',3'-Dimethyl-6-nitro-spiro[2H-1-benzopyran-2,2'-indoline]-1'-ethanol

Base Information

• Chemical Name: 3',3'-Dimethyl-6-nitro-spiro[2H-1-benzopyran-2,2'-indoline]-1'-ethanol
• CAS No.: 16111-07-2
• Molecular Formula: C20H20N2O4
• Molecular Weight: 352.39
• Hs Code.: 29339900
• Mol file: 16111-07-2.mol

Synonyms:Spiro[2H-1-benzopyran-2,2'-indoline]-1'-ethanol,3',3'-dimethyl-6-nitro- (8CI);3',3'-Dimethyl-1'-(b-hydroxyethyl)-6-nitrospiro[2H-1-benzopyran-2,2'-indoline];

Chemical Property of 3',3'-Dimethyl-6-nitro-spiro[2H-1-benzopyran-2,2'-indoline]-1'-ethanol

Chemical Property:

• Melting Point: 164-165 °C
• Boiling Point: 540.311 °C at 760 mmHg
• PKA: 14.46±0.10(Predicted)
• Flash Point: 280.57 °C
• PSA: 78.52000
• Density: 1.366 g/cm³
• LogP: 4.07500
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

98%, ^*data from raw suppliers

1-(2-Hydroxyethyl)-3,3-dimethylindolino-6’-nitrobenzopyrylospiran ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3',3'-Dimethyl-6-nitro-spiro[2H-1-benzopyran-2,2'-indoline]-1'-ethanol

There total 10 articles about 3',3'-Dimethyl-6-nitro-spiro[2H-1-benzopyran-2,2'-indoline]-1'-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: 90.0%

(R/S)-9,9,9a-trimethyl-2,3,9,9a-tetrahydrooxazolo[3,2-a]indole (36508-00-6) + 5-Nitrosalicylaldehyde (97-51-8) → 2-(3',3'-dimethyl-6-nitro-3'H-spiro[chromene-2,2'-indol]-1'-yl)-ethanol (16111-07-2)

Guidance literature:

With silica gel; In neat (no solvent); at 100 ℃; for 0.166667h; Sealed tube;

DOI:10.1021/acs.joc.5b00282

Reference yield: 89.34%

2,3,3-trimethylindoleniune (1640-39-7) + 5-Nitrosalicylaldehyde (97-51-8) + 2-bromoethanol (540-51-2) → 2-(3',3'-dimethyl-6-nitro-3'H-spiro[chromene-2,2'-indol]-1'-yl)-ethanol (16111-07-2)

Guidance literature:

2,3,3-trimethylindoleniune; 2-bromoethanol; In acetonitrile; for 24h; Reflux; Inert atmosphere;

With potassium hydroxide; In water; at 20 ℃; for 0.5h;

5-Nitrosalicylaldehyde; In ethanol; for 3h; Reflux; Inert atmosphere;

DOI:10.1021/ma5001157

Reference yield: 88.0%

2,3,3-trimethyl-N-hydroxyethylindole + 5-Nitrosalicylaldehyde (97-51-8) → 2-(3',3'-dimethyl-6-nitro-3'H-spiro[chromene-2,2'-indol]-1'-yl)-ethanol (16111-07-2)

Guidance literature:

With piperidine; In ethanol; for 0.166667h; Ambient temperature; Irradiation;

DOI:10.1080/00397919808004964

upstream raw materials:

(R/S)-9,9,9a-trimethyl-2,3,9,9a-tetrahydrooxazolo[3,2-a]indole

5-Nitrosalicylaldehyde

2-(3,3-dimethyl-2-methylene-2,3-dihydro-1H-indol-1-yl)-1-ethanol

C₆H₄C(CH₃)2NCH₂CH₂OHCOCHCHC₆H₃NO₂

Downstream raw materials:

6-[2-[1-(2-Hydroxy-ethyl)-3,3-dimethyl-1,3-dihydro-indol-(2Z)-ylidene]-eth-(Z)-ylidene]-4-nitro-cyclohexa-2,4-dienone

1-(β-methacryloxyethyl)-3,3-dimethyl-6'-nitrospiro(indoline-2,2'-<2H>benzopyran)

Refernces

• 1、 Silvi, Serena,Constable, Edwin C.,Housecroft, Catherine E.,Beves, Jonathon E.,Dunphy, Emma L.,Tomasulo, Massimiliano,Raymo, Franisco M.,Credi, Alberto. "Photochemical switching of luminescence and singlet oxygen generation by chemical signal communication". . p. 1484 - 1486. Retrieved 2009.
• 2、 Friedle, Simone,Thomas III, Samuel W.. "Controlling contact electrification with photochromic polymers". . p. 7968 - 7971. Retrieved 2010.
• 3、 Valova,Barachevsky,Khuzin,Tuktarov. "Negative Photochromism of Solutions of Functionalized Spiropyrans in a Water—Acetonitrile Mixture". . p. 1783 - 1786. Retrieved 2019.
• 4、 Zhu, Ming-Qiang,Zhang, Guo-Feng,Hu, Zhe,Aldred, Matthew P.,Li, Chong,Gong, Wen-Liang,Chen, Tao,Huang, Zhen-Li,Liu, Shiyong. "Reversible fluorescence switching of spiropyran-conjugated biodegradable nanoparticles for super-resolution fluorescence imaging". . p. 1543 - 1552. Retrieved 2014.
• 5、 Gonzalez De Los S, Eduardo A.,Lozano G, Ma. Josefina. "Novel syntheses of bis-spiropyran photochromic compounds using ultrasound II". . p. 4035 - 4041. Retrieved 1998.
• 6、 Mouraki, Alireza,Alinejad, Zeinab,Sanjabi, Samira,Salehi-Mobarakeh, Hamid,Mahdavian, Ali Reza. "Magneto-responsive photochromic acrylic copolymer nanoparticles: An investigation into the mutual interactions and photoisomerization kinetics". . . Retrieved 2021.
• 7、 Raymo, Francisco M.,Giordani, Silvia,White, Andrew J. P.,Williams, David J.. "Digital processing with a three-state molecular switch". . p. 4158 - 4169. Retrieved 2003.
• 8、 Gouda, Chinmayananda,Barik, Debashis,Maitra, Chandrima,Liang, Kai-Chieh,Ho, Feng-Cheng,Srinivasadesikan, Venkatesan,Chandran, Sarala,Wu, Shu-Pao,Lin, Ming-Chang,Lin, Hong-Cheu. "Application of stimuli-responsive FRET behavior toward cyanide detection in a photo-switchable [2]pseudorotaxane polymer containing the BODIPY donor and the merocyanine acceptor". supporting information. p. 2321 - 2333. Retrieved 2021/03/06.
• 9、 -. "Covalent organic framework material with spiropyrane molecular switch and preparation method and application". . . Retrieved 2020/05/01.