N-(Chloromethyl)phthalimide Property

Melting point:

131-135 °C (lit.)

Boiling point:

305.2±25.0 °C(Predicted)

Density 

1.3228 (rough estimate)

refractive index 

1.5790 (estimate)

storage temp. 

2-8°C

solubility 

chloroform: soluble50mg/mL

form 

powder to crystal

pka

-2.63±0.20(Predicted)

color 

White to Almost white

Water Solubility 

slightly soluble

BRN 

140942

InChI

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

InChIKey

JKGLRGGCGUQNEX-UHFFFAOYSA-N

SMILES

C1(=O)C2=C(C=CC=C2)C(=O)N1CCl

CAS DataBase Reference

17564-64-6(CAS DataBase Reference)

NIST Chemistry Reference

N-(chloromethyl)phthalimide(17564-64-6)

EPA Substance Registry System

1H-Isoindole-1,3(2H)-dione, 2-(chloromethyl)- (17564-64-6)

Safety

Hazard Codes 

Xi,Xn

Risk 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

HS Code 

29251995

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H315Causes skin irritation

H317May cause an allergic skin reaction

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

N-(Chloromethyl)phthalimide Chemical Properties,Usage,Production

Chemical Properties

white crystalline powder

Uses

N-(Chloromethyl)phthalimide 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.

Application

N-(Chloromethyl)phthalimide is a chlorine derivative of Phthalimide. Phthalimide and its derivatives are essential compounds in diverse fields. In pharmaceuticals, they are used as an intermediate material. In the medical field, they are used to synthesize compounds with antimicrobial activity, androgens, and other agents for treating tumor necrosis factor. Certain phthalimide derivatives are used as herbicides and to reduce bacterial contamination. They are widely used in industries to produce pesticides, plastics, resins, and surfactants. The N-substitution of the Phthalimide has a hypsochromic effect on color change and better color yields on poly fabrics because of the electron-donating property of the methyl group and the higher hydrophobicity of Phthalimide. Its chlorine derivative is used as an intermediate for producing medicine, pharmacy, dyes, pesticides, fire retardants, and photocopying chemicals. In particular, N-(bromomethyl)phthalimide and N-(chloromethyl)phthalimide play a vital role in anti-inflammatory, analgesic, and hypolipidimic activities[1].

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.]

References

[1] V. Balachandran , S. Rajeswari, S. Lalitha . “Density functional theory, comparative vibrational spectroscopic studies, NBO, HOMO–LUMO analyses and thermodynamic functions of N-(bromomethyl)phthalimide and N-(chloromethyl)phthalimide.” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 91 (2012): Pages 146-157.