N-(2-Bromoethyl)phthalimide

CAS NO.：574-98-1
Empirical Formula: C10H8BrNO2
Molecular Weight: 254.08
MDL number: MFCD00005902
EINECS: 209-379-9
SAFETY DATA SHEET (SDS)
Update Date: 2024-12-18 14:15:32

What is N-(2-Bromoethyl)phthalimide?

Chemical properties

white powder

The Uses of N-(2-Bromoethyl)phthalimide

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.]

Properties of N-(2-Bromoethyl)phthalimide

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 information for N-(2-Bromoethyl)phthalimide

Signal word	Danger
Pictogram(s)	Corrosion Corrosives GHS05
GHS Hazard Statements	H290:Corrosive to Metals H314:Skin corrosion/irritation
Precautionary Statement Codes	P234:Keep only in original container. P260:Do not breathe dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P280:Wear protective gloves/protective clothing/eye protection/face protection. P363:Wash contaminated clothing before reuse. P390:Absorb spillage to prevent material damage. P301+P330+P331:IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. P405:Store locked up. P406:Store in corrosive resistant/… container with a resistant inner liner.