1,3,3-Trimethylindolinonaphthospirooxazine

Base Information

• Chemical Name: 1,3,3-Trimethylindolinonaphthospirooxazine
• CAS No.: 27333-47-7
• Molecular Formula: C22H20 N2 O
• Molecular Weight: 328.414
• Hs Code.: 29349990
• European Community (EC) Number: 404-480-6,625-544-1
• DSSTox Substance ID: DTXSID90344142
• Nikkaji Number: J134.913I
• ChEMBL ID: CHEMBL1483809
• Mol file: 27333-47-7.mol

Synonyms:27333-47-7;1,3,3-Trimethylindolinonaphthospirooxazine;1,3,3-trimethylspiro[indoline-2,3'-naphtho[2,1-b][1,4]oxazine];Photorome I;1',3',3'-trimethylspiro[benzo[f][1,4]benzoxazine-3,2'-indole];MLS000554429;SMR000146746;1,3,3-Trimethylspiro[indoline-2,3'-[3H]naphth[2,1-b][1,4]oxazine];1,3,3-trimethyl-1,3-dihydrospiro[indole-2,3'-naphtho[2,1-b][1,4]oxazine];Spironaphthooxazine;Photorom I;Variacrol Blue A;1,3-Dihydro-1,3,3-trimethylspiro(2H-indole-2,3'-[3H]-naphth[2,1-b][1,4]oxazine);1,3-dihydro-1,3,3-trimethylspiro[2h-indole-2,3'-[3h]-naphth[2,1-b][1,4]oxazine];1,3-Dihydro-1,3,3-trimethylspiro[2H-indole-2,3'-[3H]naphth[2,1-b][1,4]oxazine];ChemDiv1_028499;MixCom6_000691;Oprea1_240723;SCHEMBL80364;cid_594662;CHEMBL1483809;BDBM34690;HMS667P09;DTXSID90344142;HMS2286H11;BBL027797;MFCD00013318;STK832965;AKOS001584285;DS-3334;SB64217;CS-0153806;EU-0066753;FT-0638694;T1259;C74413;A855521;SR-01000394717;J-016738;SR-01000394717-1;1',3',3'-trimethylspiro[benzo[f][1,4]benzoxazine-3,2'-indoline];1,3,3-Trimethylindolinonaphthospirooxazine [Photochromic Compound];1,3,3-Trimethylindolinonaphthospirooxazine, [Photochromic Compound];1'',3'',3''-trimethylspiro[benzo[f][1,4]benzoxazine-3,2''-indole];1'',3'',3''-trimethylspiro[benzo[f][1,4]benzoxazine-3,2''-indoline];1,3,3-trimethylspiro[2H-indole-2,3'-3H-naphth[2,1-b][1,4]oxazine];1\',3\',3\'-trimethylspiro[benzo[f][1,4]benzoxazine-3,2\'-indole];Spiro[indoline-2,3'-[3H]naphth[2,1-b][1,4]oxazine], 1,3,3-trimethyl-;1,3-Dihydro-1,3,3-trimethylspiro[2H-indole-2,3'-3H-naphtho[2,1-b][1,4]oxazine];Spiro[2H-indole-2,3'-[3H]naphth[2,1-b][1,4]oxazine], 1,3-dihydro-1,3,3-trimethyl-;1,3-DIHYDRO-1,3,3-TRIMETHYLSPIRO[2H-INDOLE-2,3'-[3H]NAPHTH[2,1-B][1,4] OXAZINE];1,3,3-Trimethylspiro[indoline-2,3'-naphtho[2,1-b][1,4]oxazine];1,3-Dihydro-1,3,3-trimethylspiro[2H-indole-2,3'-[3H]naphth[2,1-b][1,4]oxazine], >=98.0% (HPLC)

Chemical Property of 1,3,3-Trimethylindolinonaphthospirooxazine

Chemical Property:

• Appearance/Colour: YELLOW OR TAN POWDER OR CRYSTALLINE POWDER
• Vapor Pressure: 2.8E-11mmHg at 25°C
• Melting Point: 126-128 ºC
• Boiling Point: 529.1 °C at 760 mmHg
• PKA: 3.26±0.40(Predicted)
• Flash Point: 273.8 °C
• PSA: 24.83000
• Density: 1.19
• LogP: 4.55900
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: soluble in Toluene,Benzene
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 328.157563266
• Heavy Atom Count: 25
• Complexity: 558

Purity/Quality:

98%, ^*data from raw suppliers

1,3,3-Trimethylspiro[indoline-2,3''-naphtho[2,1-b][1,4]oxazine] ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(C2=CC=CC=C2N(C13C=NC4=C(O3)C=CC5=CC=CC=C54)C)C
• Uses: Photorome I is a photochromic dye that can be used as a smart colorant for a variety of applications which include optical switches, printing materials, and ophthalmic lenses.

Technology Process of 1,3,3-Trimethylindolinonaphthospirooxazine

There total 18 articles about 1,3,3-Trimethylindolinonaphthospirooxazine 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: 89.0%

1,2,3,3-tetramethyl-3H-indolium iodide (5418-63-3) + 1-Nitroso-2-naphthol (131-91-9) → 1,3,3-trimethylspiro[indoline-2,3'-naphtho[2,1-b](1,4)-oxazine] (27333-47-7)

Guidance literature:

1,2,3,3-tetramethyl-3H-indolium iodide; With cholin hydroxide; In water; at 80 ℃; for 0.333333h; Green chemistry;

1-Nitroso-2-naphthol; In water; at 80 ℃; for 0.666667h; Green chemistry;

DOI:10.1080/00397911.2019.1694690

Reference yield: 75.0%

1,3,3-Trimethyl-2-methyleneindoline (118-12-7) + 1-amino-2-naphthol (2834-92-6) → 1,3,3-trimethylspiro[indoline-2,3'-naphtho[2,1-b](1,4)-oxazine] (27333-47-7)

Guidance literature:

With sodium hydrogencarbonate; magnesium sulfate; In dimethyl sulfoxide; toluene; at 80 ℃; for 12h;

DOI:10.1016/S0040-4020(97)00640-6

Reference yield: 67.0%

1,3,3-Trimethyl-2-methyleneindoline (118-12-7) + 1-Nitroso-2-naphthol (131-91-9) → 1,3,3-trimethylspiro[indoline-2,3'-naphtho[2,1-b](1,4)-oxazine] (27333-47-7)

Guidance literature:

at 110 ℃; for 0.2h; microwave irradiation;

DOI:10.1081/SCC-120027269

upstream raw materials:

1,3,3-Trimethyl-2-methyleneindoline

1-Nitroso-2-naphthol

1-[(Z)-1,3,3-Trimethyl-1,3-dihydro-indol-(2Z)-ylidenemethylimino]-1H-naphthalen-2-one

merocyanine

Downstream raw materials:

1,3,3-trimethylindoline carboxylic acid

1-amino-2-naphthol

3,3-dimethyloxindole

1,3,3-trimethyl-1,3-dihydro-2H-indol-2-one

Refernces

• 1、 Rys,Weber,Wu. "Light-induced change of the molecular charge in a spironaphthoxazine compound". . p. 1828 - 1833. Retrieved 1993.
• 2、 Buntinx, Guy,Poizat, Olivier,Foley, Sarah,Sliwa, Michel,Alo?se, Stéphane,Lokshin, Vladimir,Samat, André. "Sub-picosecond transient absorption spectroscopy of substituted photochromic spironaphthoxazine compounds". . p. 305 - 312. Retrieved 2011.
• 3、 Yamaguchi, Takeo,Tamaki, Takashi,Kawanishi, Yuji,Seki, Takahiro,Sakuragi, Masako. "The pH Control of the Decolouration Rate of Spironaphthoxazine Derivatives". . p. 867 - 869. Retrieved 1990.
• 4、 Vajekar, Shailesh N.,Shankarling, Ganapati S.. "Highly efficient green synthesis of the photochromic spironaphthoxazines using an eco-friendly choline hydroxide catalyst". supporting information. p. 338 - 347. Retrieved 2019/12/03.
• 5、 -. "Spirooxazine photochromic compound". Paragraph 0058; 0060; 0061; 0063. . Retrieved 2019/01/24.