Isoindoline

Base Information

• Chemical Name: Isoindoline
• CAS No.: 496-12-8
• Molecular Formula: C8H9N
• Molecular Weight: 119.166
• Hs Code.: 29339980
• European Community (EC) Number: 628-708-0
• UNII: 4G7B55YCK6
• DSSTox Substance ID: DTXSID20964291
• Nikkaji Number: J6.088G
• Wikipedia: Isoindoline
• Wikidata: Q2598923
• ChEMBL ID: CHEMBL118475
• Mol file: 496-12-8.mol

Synonyms:Isoindoline;496-12-8;2,3-dihydro-1H-isoindole;1H-Isoindole, 2,3-dihydro-;2-Azaindan;1,3-dihydro-2H-isoindole;CHEMBL118475;MFCD00605324;iso-indoline;Isoindoline, 97%;1,2-dihydroisoindole;1,3-dihydroisoindole;D07SYG;SCHEMBL10612;4G7B55YCK6;LCZC2613;SCHEMBL2764305;DTXSID20964291;BCP01139;BDBM50052887;STK077165;AKOS000283835;CCG-358143;CS-W011212;MB01342;AC-20744;AM803955;SY006104;TS-01612;A7388;FT-0651501;I0751;EN300-50619;A812770;A820653;J-650387;Q-101965;Q2598923;W-202822;F2158-0930

Chemical Property of Isoindoline

Chemical Property:

• Appearance/Colour: COLORLESS TO ORANGE TO BROWN LIQUID
• Vapor Pressure: 0.338mmHg at 25°C
• Melting Point: 17 °C(lit.)
• Refractive Index: n20/D 1.57(lit.)
• Boiling Point: 199.6 °C at 760 mmHg
• PKA: 9.26±0.20(Predicted)
• Flash Point: 75.8 °C
• PSA: 12.03000
• Density: 1.04 g/cm³
• LogP: 1.61860
• Storage Temp.: 2-8°C
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 119.073499291
• Heavy Atom Count: 9
• Complexity: 88.7

Purity/Quality:

99%, ^*data from raw suppliers

Isoindoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C2=CC=CC=C2CN1
• Description: Isoindoline can be considered as the “hydrogenated sister” of isoindole which is widespread in nature as heterocyclic core of alkaloids and antibiotics.
• Uses: Isoindolinone and isoindoline pigments are high quality products. They are used in general and high grade industrial paints including original automobile and automotive refinishes, in plastics and for spin dyeing, and in high grade printing inks, especially for metal deco, laminated plastic sheets, and in printing inks for bank notes and securities. Isoindoline is used to make a chiral diamine catalyst from L-proline for the asymmetric acylation of alcohols.1

Technology Process of Isoindoline

There total 47 articles about Isoindoline 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%

2(toluene-p-sulphonyl)isoindoline (32372-83-1) → isoindoline (496-12-8)

Guidance literature:

With hydrogen bromide; propionic acid; phenol; for 2h; Inert atmosphere; Reflux;

DOI:10.1016/j.ica.2010.05.061

Reference yield: 85.0%

N-(2-furylmethyl)-N-(prop-2-en-1-yl)amine (53175-33-0) → isoindoline (496-12-8)

Guidance literature:

With hydrogenchloride; sodium hydrogencarbonate; 1.) ether, 90 deg C, 32 h, 2.) H₂O;

Reference yield: 84.0%

N-benzylisoindoline (35180-14-4) → isoindoline (496-12-8)

Guidance literature:

With palladium on activated charcoal; hydrogen; In methanol;

upstream raw materials:

oxisoindole

phthalimide

1H-2,3-benzoxazin-1-one

1-chlorophthalazine

Downstream raw materials:

(E)-3-(2,3-dihydro-1H-2-isoindolyl)-1,3-diphenyl-2-propen-1-one

N-(2-hydroxyethyl)isoindoline

2-[{1-[(3-Methylphenyl)carbonyl]-4-piperidyl}methyl]-2,3-dihydro-1H-isoindole hydrochloride

N-(4-Chlorophenyl)-1 ,3-dihydro-2H-isoindole-2-carbothioamide

Refernces

• 1、 Xia, Yuehan,Yu, Mingcheng,Zhao, Yunpeng,Xia, Li,Huang, Yafei,Sun, Nannan,Song, Meiqi,Guo, Huimin,Zhang, Yunyi,Zhu, Di,Xie, Qiong,Wang, Yonghui. "Discovery of tetrahydroquinolines and benzomorpholines as novel potent RORγt agonists". . . Retrieved 2020/12/04.
• 2、 Lu, Cong,Su, Zhishan,Jing, Dong,Jin, Songyang,Xie, Lijuan,Li, Liangrui,Zheng, Ke. "Intramolecular Reductive Cyclization of o-Nitroarenes via Biradical Recombination". supporting information. p. 1438 - 1443. Retrieved 2019/03/07.