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

Base Information

• Chemical Name: Spiro[2H-1-benzopyran-2,2'-[2H]indole], 1',3'-dihydro-1',3',3'-trimethyl-
• CAS No.: 1485-92-3
• Deprecated CAS: 157542-71-7
• Molecular Formula: C19H19 N O
• Molecular Weight: 277.36
• Hs Code.: 2934999090
• NSC Number: 206174
• DSSTox Substance ID: DTXSID50883683
• Nikkaji Number: J208.965C
• Mol file: 1485-92-3.mol

Synonyms:1485-92-3;1,3,3-Trimethylindolinobenzopyrylospiran;Spiro[2H-1-benzopyran-2,2'-[2H]indole], 1',3'-dihydro-1',3',3'-trimethyl-;1',3',3'-trimethylspiro[chromene-2,2'-indole];1,3,3-Trimethylindolinobenzospiropyran;1,3,3-Trimethylindolinobenzopyrylspiran;1,3,3-Trimethylbenzoindolinopyranospiran;NSC 206174;Trimethylindolinobenzopyrylospiran;98%;Spiro(2H-1-benzopyran-2,2'-indoline), 1',3',3'-trimethyl-;Spiro(2H-1-benzopyran-2,2'-(2H)indole), 1',3'-dihydro-1',3',3'-trimethyl-;1',3',3'-trimethylspiro[chromene-2,2'-indoline];C19H19NO;1',3',3'-trimethyl-1',3'-dihydrospiro[chromene-2,2'-indole];1,3,3-Trimethylindolinobenzopyrylospiran [Photochromic Compound];NSC206174;ChemDivAM_000656;ChemDiv1_019899;Oprea1_091264;Oprea1_597619;SCHEMBL389213;HMS643I11;DTXSID50883683;1,3,3-Trimethylindolinobenzopyrylospiran[Photochromic Compound];1,3-Trimethylindolinobenzospiropyran;1,3-Trimethylindolinobenzopyrylspiran;MFCD00059174;STK833113;1,3-Trimethylbenzoindolinopyranospiran;AKOS000513791;NSC-206174;AS-73047;CS-0313696;FT-0750506;T0344;T71803;J-008491;1,3,3-Trimethylspiro[indoline-2,2'-[2H-1]benzopyran];1/',3/',3/'-Trimethylspiro[chromene-2,2/'-indole];1',3',3'-trimethylspiro-[2h-1-benzopyran-2,2'-indoline];1',3',3'-Trimethylspiro[1(2H)-benzopyran-2,2'-indoline];1,3,3-Trimethylindolinobenzopyrylospiran, [Photochromic Compound]

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

Chemical Property:

• Melting Point: 92 °C
• Boiling Point: 408.7°Cat760mmHg
• PKA: 3.39±0.40(Predicted)
• Flash Point: 120.1°C
• PSA: 12.47000
• Density: 1.18g/cm³
• LogP: 4.28110
• Solubility.: slightly sol. in Methanol
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 277.146664230
• Heavy Atom Count: 21
• Complexity: 443

Purity/Quality:

98%,99%, ^*data from raw suppliers

1,3,3-Trimethylindolinobenzopyrylospiran [Photochromic Compound] ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2=CC=CC=C2N(C13C=CC4=CC=CC=C4O3)C)C

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

There total 17 articles about Spiro[2H-1-benzopyran-2,2'-[2H]indole], 1',3'-dihydro-1',3',3'-trimethyl- 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: 97.0%

1,3,3-Trimethyl-2-methyleneindoline (118-12-7) + salicylaldehyde (90-02-8) → 1',3',3'-trimethylspiro(2H-1-benzopyran-2,2'-indoline) (1485-92-3)

Guidance literature:

In ethanol; for 5h; Reflux;

DOI:10.1021/acs.joc.6b01193

Reference yield: 81.0%

1,2,3,3-tetramethyl-3H-indolium iodide (5418-63-3) + salicylaldehyde (90-02-8) → 1',3',3'-trimethylspiro(2H-1-benzopyran-2,2'-indoline) (1485-92-3)

Guidance literature:

With cholin hydroxide; In water; at 80 ℃; for 1h; Reagent/catalyst; Solvent; Time; Temperature;

DOI:10.1080/00397911.2017.1395053

Reference yield: 47.0%

1,3,3-Trimethyl-2-methyleneindoline (118-12-7) + salicylaldehyde (90-02-8) → 1',3',3'-trimethylspiro(2H-1-benzopyran-2,2'-indoline) (1485-92-3) + 1',3',3'-trimethyl-4-(1,3,3-trimethyl-2,3-dihydro-indol-2-ylmethyl)-1',3'-dihydro-spiro[chromene-2,2'-indole] (17487-80-8)

Guidance literature:

In ethanol; for 0.25h; Irradiation;

DOI:10.1080/00397919508010795

upstream raw materials:

1,3,3-Trimethyl-2-methyleneindoline

salicylaldehyde

1,3,3-trimethyl-2-(2-buten-1-ylidene)indoline

ethanol

Refernces

• 1、 Swansburg, Susan,Buncel, Erwin,Lemieux, Robert P.. "Thermal racemization of substituted indolinobenzospiropyrans: Evidence of competing polar and nonpolar mechanisms". . p. 6594 - 6600. Retrieved 2000.
• 2、 Levin, Peter P.,Belikov, Nikolay E.,Levina, Irina I.,Tatikolov, Alexander S.,Khodonov, Andrey A.,Khudyakov, Igor V.. "New stable colored complex of Al3+ with 1',3',3'-trimethylspiro[2H-1-benzopyran-2,2'-indoline] (BIPS)". . . Retrieved 2019.
• 3、 Keum, Sam-Rok,Lee, Ki-Bong,Kazmaier, Peter M.,Manderville, Richard A.,Buncel, Erwin. "Thermo- and Photochromic Dyes: Spiro(indolinebenzopyrans) 2. - Detailed Assignment of the 1H NMR Spectra and Structural Aspects of the Closed Form of 1,3,3-Trimethylspiro(indoline-2,2'-benzopyrans)". . p. 1128 - 1131. Retrieved 1992.
• 4、 Rastogi, Shiva K.,Zhao, Zhenze,Gildner, M. Brenton,Shoulders, Ben A.,Velasquez, Tara L.,Blumenthal, Madeleine O.,Wang, Lei,Li, Xiaopeng,Hudnall, Todd W.,Betancourt, Tania,Du, Liqin,Brittain, William J.. "Synthesis, optical properties and in vitro cell viability of novel spiropyrans and their photostationary states". . . Retrieved 2021/01/06.
• 5、 -. "Spiropyrans and spirooxazines and preparation method thereof". Paragraph 0074; 0077; 0078; 0079. . Retrieved 2019/01/22.