Spiro[2H-1-benzopyran-2,2'-[2H]indole], 1',3'-dihydro-1',3',3'-trimethyl-6-nitro-

Base Information

• Chemical Name: Spiro[2H-1-benzopyran-2,2'-[2H]indole], 1',3'-dihydro-1',3',3'-trimethyl-6-nitro-
• CAS No.: 1498-88-0
• Deprecated CAS: 81558-16-9
• Molecular Formula: C19H18 N2 O3
• Molecular Weight: 322.364
• Hs Code.: 29349990
• European Community (EC) Number: 216-102-5
• NSC Number: 206176
• DSSTox Substance ID: DTXSID70871845
• Nikkaji Number: J52.339I
• Mol file: 1498-88-0.mol

Synonyms:1',3',3'-trimethyl-6-nitroindolene-2-spiro-2-benzopyran;1,3,3-trimetylindolino-6-nitro benzopyrylospiran;6-NO2-BIPS;TMINBPS;TNSB

Chemical Property of Spiro[2H-1-benzopyran-2,2'-[2H]indole], 1',3'-dihydro-1',3',3'-trimethyl-6-nitro-

Chemical Property:

• Melting Point: 32°C
• Refractive Index: 1.6140 (estimate)
• Boiling Point: 476.3°Cat760mmHg
• PKA: 2.41±0.40(Predicted)
• Flash Point: 241.9°C
• PSA: 58.29000
• Density: 1.31g/cm³
• LogP: 4.71250
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 322.13174244
• Heavy Atom Count: 24
• Complexity: 555

Purity/Quality:

98%, ^*data from raw suppliers

1'',3'',3''-Trimethyl-6-nitrospiro[chromene-2,2''-indoline] ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2=CC=CC=C2N(C13C=CC4=C(O3)C=CC(=C4)[N+](=O)[O-])C)C
• General Description: Based on the provided literature abstracts, **1,3,3-trimethylindolino-6'-nitrobenzopyrylospiran** is a photochromic spiropyran compound that exhibits reversible isomerization between a colorless spirocyclic form and a colored merocyanine form under light or thermal stimulation. It serves as a sensitive probe for hydrogen bonding interactions due to its decoloration kinetics, which correlate with the hydrogen-bonding character of the surrounding medium. Additionally, it functions as a reusable chemosensor for aromatic thiols, undergoing selective isomerization in the dark and reversible reversion under visible light. 1,3,3-TRIMETHYLINDOLINO-6'-NITROBENZOPYRYLOSPIRAN also demonstrates thermal enantiomerization and equilibration with its merocyanine form, with distinct energy barriers for these processes. Its photochromic properties have been exploited in applications such as tuning quantum cascade lasers via UV-induced absorbance changes.

Technology Process of Spiro[2H-1-benzopyran-2,2'-[2H]indole], 1',3'-dihydro-1',3',3'-trimethyl-6-nitro-

There total 42 articles about Spiro[2H-1-benzopyran-2,2'-[2H]indole], 1',3'-dihydro-1',3',3'-trimethyl-6-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: 93.0%

1,2,3,3-tetramethyl-3H-indolium iodide (5418-63-3) + 5-Nitrosalicylaldehyde (97-51-8) → 1,3',3'-trimethyl-6-nitrospiro(indoline-2,2'-[2H]benzopyran) (1498-88-0)

Guidance literature:

With cholin hydroxide; In water; at 80 ℃; for 1h; Green chemistry;

DOI:10.1080/00397911.2017.1395053

Reference yield: 91.0%

1,3,3-Trimethyl-2-methyleneindoline (118-12-7) + 5-Nitrosalicylaldehyde (97-51-8) → 1,3',3'-trimethyl-6-nitrospiro(indoline-2,2'-[2H]benzopyran) (1498-88-0) + C31H33N3O3

Guidance literature:

In ethanol; for 0.25h; Irradiation;

DOI:10.1080/00397919508010795

Reference yield: 89.0%

1,3,3-Trimethyl-2-methyleneindoline (118-12-7) + 5-Nitrosalicylaldehyde (97-51-8) → 1,3',3'-trimethyl-6-nitrospiro(indoline-2,2'-[2H]benzopyran) (1498-88-0)

Guidance literature:

In ethanol; for 8h; Reflux;

DOI:10.1016/j.dyepig.2010.10.006

upstream raw materials:

1,3,3-Trimethyl-2-methyleneindoline

5-Nitrosalicylaldehyde

2-(1,3,3-trimethylindolenylindene)ethenal

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

Downstream raw materials:

2-(2-hydroxy-5-nitro-styryl)-1,3,3-trimethyl-3H-indolium betaine

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

C₂₀H₁₈N₃O₃^(1-)

(S)-6-nitro-1',3',3'-trimethylspiro[2H-1-benzopyran-2,2'-indoline]