17564-64-6

Basic information

• Product Name: N-(Chloromethyl)phthalimide
• Synonyms: AKOS BBS-00000871;2-(CHLOROMETHYL)-1H-ISOINDOLE-1,3(2H)-DIONE;TIMTEC-BB SBB000346;N-(CHLOROMETHYL)PHTHALIMIDE;1H-Isoindole-1,3(2H)-dione, 2-(chloromethyl)-;2-(chloromethyl)-1h-isoindole-3(2h)-dione;Chloromethylphthalimide;N-Chloromethyltrimellitimide
• CAS NO: 17564-64-6
• Molecular Formula: C₉H₆ClNO₂
• Molecular Weight: 195.6
• EINECS: 241-541-4
• Product Categories: Analytical Chemistry;Carboxyl Group Labeling Reagents for HPLC;HPLC Labeling Reagents;N-Substituted Maleimides, Succinimides & Phthalimides;N-Substituted Phthalimides;UV Detection (HPLC Labeling Reagents);Carbonyl Compounds;Cyclic Imides;Organic Building Blocks;API Intermediate
• Mol File: 17564-64-6.mol
• Article Data: 13

Chemical Properties

• Melting Point: 131-135 °C(lit.)
• Boiling Point: 305.2 °C at 760 mmHg
• Flash Point: 138.4 °C
• Appearance: white crystalline powder
• Density: 1.3228 (rough estimate)
• Refractive Index: 1.5790 (estimate)
• Storage Temp.: 2-8°C
• Solubility: chloroform: soluble50mg/mL
• PKA: -2.63±0.20(Predicted)
• Water Solubility: slightly soluble
• BRN: 140942
• CAS DataBase Reference: N-(Chloromethyl)phthalimide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(Chloromethyl)phthalimide(17564-64-6)
• EPA Substance Registry System: N-(Chloromethyl)phthalimide(17564-64-6)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-52/53-43-22
• Safety Statements: 26-36-37/39-61-45
• RIDADR: UN 2811 6.1 / PGIII
• WGK Germany: 3
• F: 9-21
• TSCA: Yes
• Hazardous Substances Data: 17564-64-6(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

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.

Purification Methods

Purify the imide by recrystallisation from EtOAc or CCl4 or via the 1:1 complex with pyridine [Sakellarios J Am Chem Soc 70 2822 1948, B.hme et al. Chem Ber 92 1258 1959]. [Beilstein 21/10 V 372.]

InChI:InChI=1/C9H6ClNO2/c10-5-11-8(12)6-3-1-2-4-7(6)9(11)13/h1-4H,5H2

Upstream product

• 118-29-6 2-(hydroxymethyl)-1H-isoindole-1,3(2H)-dione 
• 931-88-4 cis-Cyclooctene 
• 65417-83-6 pentyl phtalimidomethyl sulfide 
• 110-83-8 cyclohexene 
• 32637-30-2 N-(phenylthiomethyl)phthalimide 
• 52096-57-8 2-(Benzylthiomethyl)-1H-isoindole-1,3(2H)-dione 
• 6780-38-7 N-phthaloylglycine chloride 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 4702-13-0 N-phthaloylglycine 
• 5332-26-3 N-(bromomethyl)phtalimide 
• 550-44-7 N-methylphthalimide 
• 85-44-9 phthalic anhydride 
• 136918-14-4 phthalimide 
• 50-00-0 formaldehyd 

Downstream Products

• 318-49-0 2-(4-fluorobenzyl)isoindoline-1,3-dione 
• 101207-48-1 2-(4-methyl-3-nitrobenzyl)isoindoline-1,3-dione 
• 6119-96-6 dithiophosphoric acid O,O'-diethyl ester-S-phthalimidomethyl ester 
• 21244-24-6 2-[(4-methoxyphenyl)methyl]-1H-isoindole-1,3(2H)-dione 
• 172372-20-2 2-(2-methoxybenzyl)isoindoline-1,3-dione 
• 331729-64-7 2-(5-chloro-2-hydroxy-benzyl)isoindole-1,3-dione 
• 696-60-6 4-aminomethylphenol 
• 874014-36-5 N-(2,4-dimethyl-benzyl)-phthalimide 
• 2142-01-0 N-benzylphthalimide 
• 607-26-1 N,N'-ethylenediphthalimide 
• 134697-10-2 2-((4-nitrophenoxy)methyl)isoindoline-1,3-dione 
• 80381-84-6 N-(4,4-Diphenyl-4-hydroxy-2-butynyl)-N-phthalimidomethyl pyrrolidinium chloride 
• 150423-22-6 N-[4-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethoxy)-phenyl]-acetamide 
• 26990-24-9 acid chloride of S-butylphenylthiophosphonous acid 

Relevant articles and documents

Synthesis, α-glucosidase inhibition and molecular docking studies of novel thiazolidine-2,4-dione or rhodanine derivatives

A series of novel thiazolidine-2,4-dione or rhodanine derivatives (5a-5k, 6a-6k) were synthesized and evaluated for their α-glucosidase inhibitory activity. The majority of compounds exhibited potent inhibitory activity in the range of 5.44 ± 0.13 to 50.45 ± 0.39 μM, when compared to the standard drug acarbose (IC50 = 817.38 ± 6.27 μM). Among the compounds in the series, compounds 5k, 6a, 6b, 6e, 6h and 6k showed potent inhibitory potential with IC50 values of 20.95 ± 0.21, 16.11 ± 0.19, 7.72 ± 0.16, 7.91 ± 0.17, 6.59 ± 0.15 and 5.44 ± 0.13 μM, respectively. Compound 6k (IC50 = 5.44 ± 0.13 μM), containing chloro and rhodanine groups at the 2- and 4-positions of the phenyl ring respectively, was found to be the most active compound that inhibits α-glucosidase activity. Furthermore, molecular docking studies were performed to understand the binding interactions between the molecule and enzyme.

Aminomethylation of Michael acceptors: Complementary radical and polar approaches mediated by dialkylzincs

Phtalimidomethyl iodide and substituted maleimidomethyl iodide were used as radical precursors in dialkylzinc-mediated radical addition to diethyl fumarate. The reactions led stereoselectively to functionalized pyrrolizidines. The radical mechanism was supported by spin-trapping experiments and rationalized by theoretical calculations. Radical additions, on the one hand, and carbozincation followed by transmetalation with copper(I), on the other, were shown to be complementary methods to achieve the formal aminomethylation of activated unsaturated compounds. Copyright

NMR study of the tautomeric behavior of N -(α-Aminoalkyl)tetrazoles

N-(α-Aminoalkyl)tetrazoles exist in solution as equilibrium mixtures of N1 and N2 tautomers. The position of equilibrium depends significantly on the polarity of the solvent and the substituents in the tetrazole ring. Interconversion between individual tautomers is shown to proceed via tight ion-pair intermediates in which intramolecular recombination is faster than the intermolecular crossover since the latter probably requires solvent separation of ion-pair intermediates.