N-(2-Bromoethyl)phthalimide Chemical Properties

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

InChI

InChI=1S/C10H8BrNO2/c11-5-6-12-9(13)7-3-1-2-4-8(7)10(12)14/h1-4H,5-6H2

InChIKey

CHZXTOCAICMPQR-UHFFFAOYSA-N

SMILES

C1(=O)C2=C(C=CC=C2)C(=O)N1CCBr

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

Risk Statements 

36/37/38

Safety Statements 

24/25

WGK Germany 

3

TSCA 

Yes

HS Code 

29251995

MSDS

• Language:English Provider:N-(2-Bromoethyl)phthalimide
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

N-(2-Bromoethyl)phthalimide Usage And Synthesis

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

reaction suitability

reagent type: cross-linking reagent

Synthesis

In a 250 mL two-necked round-bottomed flask, 50 mmol of 3-hydroxy-1H-isoindol-1-one, 150 mmol of 1,2-dibromoethane, 2.0 g of tetrabutylammonium bromide (TBAB) as a phase-transfer catalyst, and 120 mL of dimethylformamide (DMF) were sequentially added. The reaction mixture was heated to 50-80 °C and maintained at this temperature for 5 h, during which the progress of the reaction was monitored by thin-layer chromatography (TLC) [unfolding reagent ratio: petroleum ether:ethyl acetate = 5:1 (v/v)]. After completion of the reaction, the solvent was removed by distillation under reduced pressure. Ice water was added to the residue and a large white solid was precipitated, which was filtered, washed and dried. The resulting solid was transferred to a 250 mL dry round bottom flask and recrystallized by adding 30 mL of methanol. After cooling to room temperature, the crystals were precipitated, and after filtration and drying, 10.3 g of white solid product was obtained in 81% yield.

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.]

References

[1] Journal of Heterocyclic Chemistry, 2008, vol. 45, # 5, p. 1371 - 1375
[2] Dalton Transactions, 2013, vol. 42, # 44, p. 15735 - 15747
[3] Patent: CN105237451, 2016, A. Location in patent: Paragraph 0051; 0055; 0056; 0057; 0058
[4] Journal of Medicinal Chemistry, 2006, vol. 49, # 26, p. 7826 - 7835
[5] Journal of Organometallic Chemistry, 2018, vol. 868, p. 154 - 163

N-(2-Bromoethyl)phthalimide(574-98-1)Related Product Information

• N-(3-BROMOPROPYL)PHTHALIMIDE
• N-Methylphthalimide
• Succinimide
• Bismaleimide
• Potassium phthalimide
• 4-Aminophthalimide
• 4-Nitrophthalimide
• 3-Nitrophthalimide
• N-Hydroxyphthalimide
• O-Phthalimide
• DIALIFOS
• Isoindoline
• BROMO 2-DEOXY-2-N-PHTHALIMIDO-3,4,6-TRI-O-ACETYL-A, B-D-GLUCOPYRANOSIDE
• (S)-N-(1-BROMO-2-PROPYL)PHTHALIMIDE
• N-(2-Bromoethyl)phthalimide
• 2-(2-bromoethyl)-5-nitro-2,3-dihydro-1H-isoindole-1,3-dione
• 2-(2-bromoethyl)-4-nitro-1H-isoindole-1,3(2H)-dione
• SPECS AJ-333/25116002