(S)-2-(3-chloro-2-hydroxypropyl)isoindoline-1,3-dione

Base Information

• Chemical Name: (S)-2-(3-chloro-2-hydroxypropyl)isoindoline-1,3-dione
• CAS No.: 148857-42-5
• Molecular Formula: C11H10ClNO3
• Molecular Weight: 239.658
• UNII: F5WWW7SGG3
• Nikkaji Number: J1.053.588C
• Mol file: 148857-42-5.mol

Synonyms:148857-42-5;(S)-2-(3-chloro-2-hydroxypropyl)isoindoline-1,3-dione;2-[(2S)-3-Chloro-2-hydroxypropyl]-1H-isoindole-1,3(2H)-dione;2-[(2S)-3-chloro-2-hydroxypropyl]isoindole-1,3-dione;2-[(2S)-3-chloro-2-hydroxypropyl]-2,3-dihydro-1H-isoindole-1,3-dione;F5WWW7SGG3;SCHEMBL5214602;KBRVYEPWGIQEOF-SSDOTTSWSA-N;CS-M0559;YFA85742;(s)-1-phthalimido-3-chloro-2-propanol;(S)-1-Phthlimido-3-chloro-2-propanol;CS-13655;EN300-226336;2-(3-Chloro-2-hydroxypropyl)isoindoline-1,3-dione, (S)-;1H-Isoindole-1,3(2H)-dione, 2-[(2S)-3-chloro-2-hydroxypropyl]-

Chemical Property of (S)-2-(3-chloro-2-hydroxypropyl)isoindoline-1,3-dione

Chemical Property:

• Boiling Point: 405.4±35.0 °C(Predicted)
• PKA: 13.25±0.20(Predicted)
• PSA: 57.61000
• Density: 1.444±0.06 g/cm3(Predicted)
• LogP: 0.82020
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 239.0349209
• Heavy Atom Count: 16
• Complexity: 284

Purity/Quality:

99% ^*data from raw suppliers

2-[(2S)-3-Chloro-2-hydroxypropyl]-1H-isoindole-1,3(2H)-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=O)N(C2=O)CC(CCl)O
• Isomeric SMILES: C1=CC=C2C(=C1)C(=O)N(C2=O)C[C@@H](CCl)O
• Uses: 2-[(2S)-3-Chloro-2-hydroxypropyl]-1H-isoindole-1,3(2H)-dione is used to prepare Diplogelasinospora grovesii IMI 171018, new whole cell biocatalyst for stereoselective reduction of ketones.

Technology Process of (S)-2-(3-chloro-2-hydroxypropyl)isoindoline-1,3-dione

There total 7 articles about (S)-2-(3-chloro-2-hydroxypropyl)isoindoline-1,3-dione 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: 86.0%

phthalimide (136918-14-4,85-41-6) + epichlorohydrin (106-89-8,24969-06-0,13403-37-7) → 2-oxiranylmethylisoindole-1,3-dione (5455-98-1) + 2-(3-chloro-2-hydroxypropyl)-1H-isoindole-1,3(2H)-dione (19667-37-9,34839-11-7,148857-42-5,148857-44-7)

Guidance literature:

With potassium fluoride on basic alumina; In 2-methyltetrahydrofuran; for 3h; chemoselective reaction; Inert atmosphere; Reflux;

DOI:10.1039/c0gc00113a

Reference yield: 83.0%

phthalimide (136918-14-4,85-41-6) + (R)-(-)-epichlorohydrin (51594-55-9,24969-06-0,13403-37-7) → (S)-N-glycidylphthalimide (161596-47-0) + 2-((S)-3-chloro-2-hydroxypropyl)isoindoline-1,3-dione (148857-42-5)

Guidance literature:

With potassium fluoride on basic alumina; In 2-methyltetrahydrofuran; for 3h; stereospecific reaction; Inert atmosphere; Reflux;

DOI:10.1039/c0gc00113a

Reference yield: 21.0%

2-oxiranylmethylisoindole-1,3-dione (5455-98-1) + 4-chlorobenzaldehyde (104-88-1) → 2-(3-chloro-2-hydroxypropyl)-1H-isoindole-1,3(2H)-dione (19667-37-9,34839-11-7,148857-42-5,148857-44-7) + 2-chloro-1-(4-chlorophenyl)ethanol (6378-66-1)

Guidance literature:

2-oxiranylmethylisoindole-1,3-dione; 4-chlorobenzaldehyde; With Chloroiodomethane; In 2-methyltetrahydrofuran; at -78 ℃; for 0.0333333h;

With methyllithium; In 2-methyltetrahydrofuran; diethyl ether; at -78 ℃; for 1h;

DOI:10.1039/d0ob02407d

upstream raw materials:

phthalimide

epichlorohydrin

(R)-(-)-epichlorohydrin

(S)-epichlorohydrin

Downstream raw materials:

N,N'-(2-hydroxy-propanediyl)-bis-phthalimide

1-amino-3-(dimethylamino)propan-(2RS)-2-ol

1-amino-3-diethylamino-propan-2-ol

N-(3-anilino-2-hydroxy-propyl)-phthalimide

Refernces

• 1、 Babu, Meruva Suresh,Raghunadh, Akula,Ramulu, Konda,Dahanukar, Vilas H.,Syam Kumar, Unniaran K.,Dubey, P. Kumar. "A practical and enantiospecific synthesis of (-)-(R)- and (+)-(S)-piperidin-3-ols". . p. 1507 - 1515. Retrieved 2015/02/19.
• 2、 -. "PROCESS FOR THE PREPARATION OF CHIRAL GLYCIDYLPHTHALIMIDE IN HIGHLY OPTICAL PURITY". Page/Page column 8-9. . Retrieved 2008/06/13.