N-(Chloromethyl)phthalimide

Base Information

• Chemical Name: N-(Chloromethyl)phthalimide
• CAS No.: 17564-64-6
• Molecular Formula: C9H6ClNO2
• Molecular Weight: 195.605
• Hs Code.: 29251995
• European Community (EC) Number: 241-541-4
• NSC Number: 29558
• UNII: N45CYY145E
• DSSTox Substance ID: DTXSID3027790
• Nikkaji Number: J26.866F
• Wikidata: Q72454656
• ChEMBL ID: CHEMBL369138
• Mol file: 17564-64-6.mol

Synonyms:17564-64-6;N-(Chloromethyl)phthalimide;2-(Chloromethyl)isoindoline-1,3-dione;N-Chloromethylphthalimide;Chloromethylphthalimide;1H-Isoindole-1,3(2H)-dione, 2-(chloromethyl)-;N-Chloromethyltrimellitimide;2-(Chloromethyl)-1H-isoindole-1,3(2H)-dione;2-(chloromethyl)isoindole-1,3-dione;Phthalimide, N-(chloromethyl)-;Phthalimide, N-chloromethyl-;MFCD00005898;CCRIS 7991;EINECS 241-541-4;NSC 29558;N45CYY145E;DTXSID3027790;NSC-29558;N-CHLOROMETHYL PHTHALIMIDE;NSC29558;N-(Chloromethyl)phthalimide[for HPLC Labeling];UNII-N45CYY145E;N-(chloromethyl) phthalimide;SCHEMBL31402;2-(chloromethyl)-2,3-dihydro-1H-isoindole-1,3-dione;CHEMBL369138;DTXCID807790;PHTHALIMIDOMETHYL CHLORIDE;JKGLRGGCGUQNEX-UHFFFAOYSA-;N-(Chloromethyl)phthalimide, 97%;Tox21_200731;BBL100147;STL511907;1H-Isoindole-1, 2-(chloromethyl)-;AKOS000120605;CS-W015714;SB66096;NCGC00248814-01;NCGC00258285-01;AM808142;BS-15659;SY048393;CAS-17564-64-6;LS-188474;A5504;FT-0637566;EN300-18273;2-(Chloromethyl)-1H-isoindole-1,3(2H)-dione #;W-107845

Chemical Property of N-(Chloromethyl)phthalimide

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 131-135 °C
• Refractive Index: 1.5790 (estimate)
• Boiling Point: 305.2 °C at 760 mmHg
• PKA: -2.63±0.20(Predicted)
• Flash Point: 138.4 °C
• PSA: 37.38000
• Density: 1.448 g/cm³
• LogP: 1.41680
• Storage Temp.: 2-8°C
• Solubility.: chloroform: soluble50mg/mL
• Water Solubility.: slightly soluble
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 195.0087061
• Heavy Atom Count: 13
• Complexity: 230

Purity/Quality:

99% ^*data from raw suppliers

N-(Chloromethyl)phthalimide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-52/53-43-22
• Safety Statements: 26-36-37/39-61-45

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Other Nitrogen Rings
• Canonical SMILES: C1=CC=C2C(=C1)C(=O)N(C2=O)CCl
• Uses: It is used as an agrochemical and medicine intermediates and is used in organic synthesis. Microporous membranes prepared from chemically modified polysulfone, which is a derivative of this compound have better streaming potential.

Technology Process of N-(Chloromethyl)phthalimide

There total 36 articles about N-(Chloromethyl)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: 93.0%

2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione (118-29-6) → N-(chloromethyl)phthalimide (17564-64-6)

Guidance literature:

With thionyl chloride; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; for 2.5h;

DOI:10.1016/j.tet.2012.11.074

Reference yield: 90.0%

phthalimide (136918-14-4,85-41-6) + formaldehyd (50-00-0,30525-89-4,61233-19-0) → N-(chloromethyl)phthalimide (17564-64-6)

Guidance literature:

phthalimide; formaldehyd; In water; Heating;

With thionyl chloride; In dichloromethane; N,N-dimethyl-formamide; at 20 ℃; Further stages.;

DOI:10.1002/jhet.5570440435

Reference yield: 90.0%

N-phthaloylglycine (4702-13-0) → N-(chloromethyl)phthalimide (17564-64-6)

Guidance literature:

With tert-butylhypochlorite; silver triflate-bis(1,10-phenanthroline) complex; In acetonitrile; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1021/ja210361z

upstream raw materials:

2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione

N-phthaloylglycine chloride

styrene

pentyl phtalimidomethyl sulfide

Downstream raw materials:

2-(4-fluorobenzyl)isoindoline-1,3-dione

2-(4-methyl-3-nitrobenzyl)isoindoline-1,3-dione

dithiophosphoric acid O,O'-diethyl ester-S-phthalimidomethyl ester

2-[(4-methoxyphenyl)methyl]-1H-isoindole-1,3(2H)-dione

Refernces

• 1、 Huang, Zhongyan,Xu, Jiaxi. "Efficient synthesis of N-protected 1-substituted homotaurines from a xanthate and olefins". . p. 1050 - 1056. Retrieved 2013/02/23.
• 2、 Wang, Zhentao,Zhu, Lin,Yin, Feng,Su, Zhongquan,Li, Zhaodong,Li, Chaozhong. "Silver-catalyzed decarboxylative chlorination of aliphatic carboxylic acids". experimental part. p. 4258 - 4263. Retrieved 2012/04/10.