1H-Isoindole-1,3(2H)-dione, 2-(azidomethyl)-

Base Information

• Chemical Name: 1H-Isoindole-1,3(2H)-dione, 2-(azidomethyl)-
• CAS No.: 26964-88-5
• Molecular Formula: C₉H₆N₄O₂
• Molecular Weight: 202.172
• Mol file: 26964-88-5.mol

Synonyms:Phthalimide,N-(azidomethyl)- (7CI,8CI)

Chemical Property of 1H-Isoindole-1,3(2H)-dione, 2-(azidomethyl)-

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 87.13000
• Density: g/cm³
• LogP: 0.94106

Purity/Quality:

2-(azidomethyl)isoindoline-1,3-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1H-Isoindole-1,3(2H)-dione, 2-(azidomethyl)-

There total 4 articles about 1H-Isoindole-1,3(2H)-dione, 2-(azidomethyl)- 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: 96.0%

N-(chloromethyl)phthalimide (17564-64-6) → 2-(azidomethyl)isoindoline-1,3-dione (26964-88-5)

Guidance literature:

With sodium azide; In dimethyl sulfoxide; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1002/anie.201210126

Reference yield: 95.0%

N-(bromomethyl)phtalimide (5332-26-3) → 2-(azidomethyl)isoindoline-1,3-dione (26964-88-5)

Guidance literature:

With sodium azide; tetra-(n-butyl)ammonium iodide; In dichloromethane; water; for 24h; Reflux;

DOI:10.3184/174751916X14608096414015

Reference yield: 40.0%

N-phthaloylglycine (4702-13-0) → 2-(azidomethyl)isoindoline-1,3-dione (26964-88-5)

Guidance literature:

With phenylsulfonyl azide; dipotassium peroxodisulfate; silver fluoride; In water; acetonitrile; at 55 ℃; for 48h; under 760.051 Torr; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.orglett.5b02155

upstream raw materials:

N-(bromomethyl)phtalimide

N-(chloromethyl)phthalimide

N-phthaloylglycine

Refernces

• 1、 Zhang, Shaoguang,Zhang, Wen-Xiong,Xi, Zhenfeng. "Lewis acid catalyzed site-selective cycloadditions of 2,6- diazasemibullvalenes with isocyanides, azides, and diazo compounds for the synthesis of diaza- and triazabrexadiene derivatives". . . Retrieved 2013.
• 2、 Lieber,Thomas. "". . p. 144,145. Retrieved 1961.
• 3、 Assis, Shalom P. De O.,Da Silva, Moara T.,Da Silva, Filipe Torres,Sant’Anna, Mirella P.,De Albuquerque Tenório, Carolina M.B.,Brito Dos Santos, Caroline F.,Da Fonseca, Caíque S.M.,Seabra, Gustavo,Lima, Vera L.M.,De Oliveira, Ronaldo N.. "Design and Synthesis of Triazole-Phthalimide Hybrids with Anti-inflammatory Activity". . p. 96 - 105. Retrieved 2019/04/02.