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
• Uses: NitroBIPS is used as a photochromic dye which can be incorporated in poly(vinylalcohol)(PVA) by electro-spinning to form PVA-spiropyran nanofibres. It has photo-responsive behaviour that may be useful in optical data storage applications. It can be used to dope liquid crystal to develop a coloured scattering device that is dual responsive and allows the initiation of electrohydrodynamic instabilities(EHDI). Addition of NitroBIPS can modify the transparency from 100% to 16%, providing a shielding effect which can be used for smart window applications. It may also be used to enhance the adhesion property of polystyrene(PS) on the glass substrate by improving the shear strength by a factor of 7.

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:

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

4-Nitro-6-[2-[1,3,3-trimethyl-1,3-dihydro-indol-(2E)-ylidene]-eth-(E)-ylidene]-cyclohexa-2,4-dienone

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

5-Nitrosalicylaldehyde

Refernces

• 1、 Shiraishi, Yasuhiro,Yamamoto, Kohei,Sumiya, Shigehiro,Hirai, Takayuki. "Spiropyran as a reusable chemosensor for selective colorimetric detection of aromatic thiols". . p. 12137 - 12142. Retrieved 2014.
• 2、 Basnar,Mujagic,Andrews,Roch,Schrenk,Strasser. "Light induced tuning of quantum cascade lasers". . . Retrieved 2010.
• 3、 Schomburg,Wark,Rohlfing,Schulz-Ekloff,Woehrle. "Photochromism of spiropyran in molecular sieve voids: Effects of host-guest interaction on isomer status, switching stability and reversibility". . p. 2014 - 2021. Retrieved 2001.
• 4、 Santos, Cerize S.,Miller, Allyson C.,Pace, Tamara C. S.,Morimitsu, Kentaro,Bohne, Cornelia. "Photochromism of a spiropyran and a diarylethene in bile salt aggregates in aqueous solution". . p. 11319 - 11328. Retrieved 2014.
• 5、 Cola?o, Melwin,Carletta, Andrea,Van Gysel, Mégane,Robeyns, Koen,Tumanov, Nikolay,Wouters, Johan. "Direct Access by Mechanochemistry or Sonochemistry to Protonated Merocyanines: Components of a Four-State Molecular Switch". . p. 520 - 526. Retrieved 2018.
• 6、 Seki, Takahiro,Ichimura, Kunihiro. "Effect of the Phase Transition of a Bilayer Membrane on the Thermal Decolouration of a U.V.-irradiated Indolinospirobenzopyran". . p. 1187 - 1188. Retrieved 1987.
• 7、 Garg, Shubham,Schwartz, Heidi,Kozlowska, Mariana,Kanj, Anemar Bruno,Müller, Kai,Wenzel, Wolfgang,Ruschewitz, Uwe,Heinke, Lars. "Conductance Photoswitching of Metal–Organic Frameworks with Embedded Spiropyran". . p. 1193 - 1197. Retrieved 2019.
• 8、 Lyubimov, A. V.,Marevtsev, V. S.,Ermakova, V. D.,Cherkashin, M. I.. "PHOTOCHROMIC PROPERTIES OF 1,3,3-TRIMETHYL-6'-NITROSPIRO(INDOLINO-2,2'-BENZOTHIOPYRAN) IN POLYMERIC FILMS". . p. 1380 - 1383. Retrieved 1985.
• 9、 Ramesh, V.,Labes, M. M.. "Influence of Disc-Rod-Sphere Phase Transitions in Nematic Lyotropics on a Unimolecular Isomerization Reaction". . p. 3228 - 3231. Retrieved 1987.
• 10、 Laptev,Lukin,Belikov,Zvezdin,Demina,Barachevsky,Varfolomeev,Khodonov,Shvets. "Synthesis and studies of photochromic properties of spirobenzopyran carboxy derivatives and their model compounds as potential markers". . p. 2026 - 2035. Retrieved 2014.