(R)-(-)-N-(2,3-Epoxypropyl)phthalimide

Base Information

• Chemical Name: (R)-(-)-N-(2,3-Epoxypropyl)phthalimide
• CAS No.: 181140-34-1
• Molecular Formula: C11H9NO3
• Molecular Weight: 203.197
• Hs Code.: 29251900
• European Community (EC) Number: 629-091-0
• UNII: FN3ZN7ZHU8
• DSSTox Substance ID: DTXSID101045197
• Nikkaji Number: J3.151.503C
• Mol file: 181140-34-1.mol

Synonyms:181140-34-1;(R)-(-)-N-(2,3-Epoxypropyl)phthalimide;(R)-N-Glycidylphthalimide;(R)-2-(oxiran-2-ylmethyl)isoindoline-1,3-dione;(R)-(-)-Glycidyl phthalimide;2-[[(2R)-oxiran-2-yl]methyl]isoindole-1,3-dione;(R)-Glycidyl phthalimide;FN3ZN7ZHU8;N-(R)-Glycidylphthalimide;Glycidyl phthalimide, (R)-;1H-Isoindole-1,3(2H)-dione, 2-[(2R)-2-oxiranylmethyl]-;2-{[(2R)-oxiran-2-yl]methyl}-2,3-dihydro-1H-isoindole-1,3-dione;2-[(2R)-Oxiranylmethyl)-1H-isoindole-1,3-dione;2-[(2r)-oxiranylmethyl]-1h-isoindole-1,3-dione;1H-Isoindole-1,3(2H)-dione, 2-((2R)-2-oxiranylmethyl)-;MFCD04973349;UNII-FN3ZN7ZHU8;SCHEMBL767566;1H-Isoindole-1,3(2H)-dione, 2-[(2R)-oxiranylmethyl]-;(R)-2-(phthalimidomethyl)oxirane;DUILGEYLVHGSEE-SSDOTTSWSA-N;DTXSID101045197;CS-M0558;AC9490;(R)-N-(2,3-Epoxypropyl)phthalimide;AKOS015914626;N-(2(R), 3-Epoxypropyl)phthalimide;(R)-N-(2,3-epoxypropyl)-phthalimide;AS-69534;N-[(2R)-oxiran-2-ylmethyl]-phthalimide;G0327;EN300-3197329;A856048;J-011565;J-803035;Z1509549164;1H-Isoindole-1,3(2H)-dione,2-[(2R)-2-oxiranylmethyl]-;2-[(2R)-2-oxiranylmethyl]-1H-isoindole-1,3(2H)-dione;(R)-(-)-N-(2,3-Epoxypropyl)phthalimide, >=99.0% (GC)

Chemical Property of (R)-(-)-N-(2,3-Epoxypropyl)phthalimide

Chemical Property:

• Vapor Pressure: 5.38E-05mmHg at 25°C
• Melting Point: 101 °C
• Refractive Index: -10 ° (C=2.2, CHCl3)
• Boiling Point: 347.4 °C at 760 mmHg
• PKA: -2.24±0.20(Predicted)
• Flash Point: 163.9 °C
• PSA: 58.70000
• Density: 1.446 g/cm³
• LogP: 0.84030
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 203.058243149
• Heavy Atom Count: 15
• Complexity: 291

Purity/Quality:

98% ^*data from raw suppliers

N-(R)-GlycidylPhthalimide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(O1)CN2C(=O)C3=CC=CC=C3C2=O
• Isomeric SMILES: C1[C@H](O1)CN2C(=O)C3=CC=CC=C3C2=O
• Uses: (R)-N-Glycidylphthalimide is a reagent used for the simultaneous preparation of amino alcohol solvating agents as well as preparation of orally available anticoagulants. (R)-(-)-N-(2,3-Epoxypropyl)phthalimide may be used in the preparation of the following potential chiral solvating agents:2-[(2R)-2-hydroxy-3-[[(1R)-2-hydroxy-1-phenyl-ethyl]amino]propyl] isoindoline-1,3-dione2-[(2R)-2-hydroxy-3-[[(1R,2S)-2-hydroxyindan-1-yl]amino]propyl]isoindoline-1,3-dione2-[(2R)-2-hydroxy-3-[[(1R)-1-(hydroxymethyl)-propyl]amino]propyl] isoindoline-1,3-dione2-[(2R)-2-hydroxy-3-[[(1S)-1-phenylethyl]-amino]propyl]isoindoline-1,3-dione It may also be used in the synthesis of 2-((5R)-2-oxo-5-oxazolidinyl) methyl)-1H-isoindole-1,3 (2H)-dione.

Technology Process of (R)-(-)-N-(2,3-Epoxypropyl)phthalimide

There total 11 articles about (R)-(-)-N-(2,3-Epoxypropyl)phthalimide 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: 90.6%

2-[(2R)-3-bromo-2-hydroxypropyl]-1H-isoindole-1,3(2H)-dione (641617-21-2) → (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 18h; Product distribution / selectivity;

Reference yield: 89.0%

phthalimide (136918-14-4,85-41-6) + (R)-(-)-epichlorohydrin (51594-55-9,24969-06-0,13403-37-7) → (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1)

Guidance literature:

phthalimide; (R)-(-)-epichlorohydrin; With benzyltrimethylammonium chloride; In isopropyl alcohol; at 40 ℃; for 24h;

With potassium tert-butylate; In isopropyl alcohol; at 20 ℃; for 3h;

Reference yield: 86.0%

phthalimide (136918-14-4,85-41-6) + (R)-oxiranemethanol (57044-25-4) → (-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 - 25 ℃; for 18h;

DOI:10.1016/0957-4166(96)00198-X

upstream raw materials:

phthalimide

(R)-oxiranemethanol

(S)-epichlorohydrin

potassium phtalimide

Downstream raw materials:

2-oxo-5-phthalimidomethyl-tetrahydro-furan-3-carboxylic acid ethyl ester

2,2'-((2R,2'R)-((4-(3-oxomorpholino)phenyl)azadiyl)bis(2-hydroxypropane-3,1-diyl))bis(isoindoline-1,3-dione)

Refernces

• 1、 Tanaka, Koichi,Kawakita, Tomohiro,Morawiak, Maja,Urbanczyk-Lipkowska, Zofia. "A novel homochiral metal-organic framework with an expanded open cage based on (: R)-3,3′-bis(6-carboxy-2-naphthyl)-2,2′-dihydroxy-1,1′-binaphthyl: synthesis, X-ray structure and efficient HPLC enantiomer separation". . p. 487 - 493. Retrieved 2019/01/21.
• 2、 Pace, Vittorio,Hoyos, Pilar,Fernandez, Maria,Sinisterra, Jose V.,Alcantara, Andres R.. "2-Methyltetrahydrofuran as a suitable green solvent for phthalimide functionalization promoted by supported KF". supporting information; experimental part. p. 1380 - 1382. Retrieved 2010/09/05.