N-(2-Bromoethyl)phthalimide Property

Melting point:

80-83 °C (lit.)

Boiling point:

318 °C

Density 

1.6254 (rough estimate)

refractive index 

1.6320 (estimate)

storage temp. 

Sealed in dry,Room Temperature

pka

-2.35±0.20(Predicted)

form 

Crystalline Powder

color 

White to slightly pink or beige

Water Solubility 

insoluble

BRN 

148736

CAS DataBase Reference

574-98-1(CAS DataBase Reference)

NIST Chemistry Reference

N-(beta-bromoethyl)phthalimide(574-98-1)

EPA Substance Registry System

1H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)- (574-98-1)

Safety

Risk Statements 

36/37/38

Safety Statements 

24/25

WGK Germany 

3

TSCA 

Yes

HS Code 

29251995

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H290May be corrosive to metals

H314Causes severe skin burns and eye damage

Precautionary statements

P234Keep only in original container.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P363Wash contaminated clothing before reuse.

P390Absorb spillage to prevent material damage.

P405Store locked up.

P406Store in corrosive resistant/… container with a resistant inner liner.

N-(2-Bromoethyl)phthalimide Chemical Properties,Usage,Production

Chemical Properties

white powder

Uses

N-(2-Bromoethyl)phthalimide is an intermediate used in organic synthesis. It can react with phenyl magnesium bromide to get 2-(2-bromo-ethyl)-3-hydroxy-3-phenyl-isoindolin-1-one.

Synthesis Reference(s)

Journal of the American Chemical Society, 71, p. 2425, 1949 DOI: 10.1021/ja01175a052
Organic Syntheses, Coll. Vol. 1, p. 119, 1941

Purification Methods

The following is to be carried out in an efficient FUME HOOD. Dissolve the compound (180g) in CS2 (500 mL) by refluxing for 15minutes (to cause the separation of the most likely impurity, 1,2-diphthalimidoethane), filter and evaporate under reduced pressure. The product forms light tan crystals (m 78-80o). Recrystallise it from EtOH (charcoal) [the compound (50g) is dissolved in hot 75% EtOH (200mL), boiled for ca 10 minutes, carbon is added (5g, Norite), filter and cool to 0o], to give white crystals (40g) which can be recrystallised (m 80-81o); and further recrystallisation gives m 82-83o. [Salzberg & Supniewski Org Synth Coll Vol I 119 1932, Landini & Rolla Synthesis 389 1976, Beilstein 21/10 V 275.]