N-(4-Bromobutyl)phthalimide Chemical Properties

Melting point:

76-80 °C (lit.)

Boiling point:

165-170°C 1mm

Density 

1.5271 (rough estimate)

refractive index 

1.6320 (estimate)

Flash point:

165-170°C/1mm

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

-2.15±0.20(Predicted)

form 

Powder

color 

White to light brown

Water Solubility 

Soluble in ethanol. Insoluble in water.

BRN 

164119

InChIKey

UXFWTIGUWHJKDD-UHFFFAOYSA-N

CAS DataBase Reference

5394-18-3(CAS DataBase Reference)

NIST Chemistry Reference

N-(4-bromobutyl)phthalimide(5394-18-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29251995

MSDS

• Language:English Provider:2-(4-Bromobutyl)-1H-isoindole-1,3(2H)-dione
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

N-(4-Bromobutyl)phthalimide Usage And Synthesis

Chemical Properties

white crystalline powder

Uses

N-(4-Bromobutyl)phthalimide is used in organic synthesis and the production of pharmaceutical. It can react with 1-phenyl-piperazine to get N-[4-(4-phenyl-piperazin-1-yl)-butyl]-phthalimide. It is a useful synthesis reagent used to synthesize B-cyclodextrin derivatives.

reaction suitability

reagent type: cross-linking reagent
reagent type: linker

Synthesis

General procedure for the synthesis of N-(4-bromobutyl)phthalimide from 1,4-dibromobutane and 3-hydroxy-1H-isoindol-1-one: phthalimide (148 mg, 1 mmol), 1,4-dibromobutane (1.080 g, 5 mmol) and potassium carbonate (276 mg, 2 mmol) were added to acetone (3 mL) and the reaction mixture was refluxed for 2 hours. After completion of the reaction, it was cooled to room temperature and the reaction mixture was purified by column chromatography using petroleum ether: acetone (40:1) as eluent to afford N-(4-bromobutyl)phthalimide (260 mg, 92% yield) as a white solid.

References

[1] Journal of Organic Chemistry, 2004, vol. 69, # 18, p. 6094 - 6099
[2] Angewandte Chemie - International Edition, 2018, vol. 57, # 6, p. 1532 - 1536
[3] Angew. Chem., 2018, vol. 130, # 6, p. 1548 - 1552,5
[4] European Journal of Medicinal Chemistry, 2018, vol. 145, p. 74 - 85
[5] Journal of the Chinese Chemical Society, 2013, vol. 60, # 12, p. 1431 - 1436

N-(4-Bromobutyl)phthalimide(5394-18-3)Related Product Information

• N-Hydroxyphthalimide
• Succinimide
• 4-Nitrophthalimide
• 4-Aminophthalimide
• 3-Nitrophthalimide
• O-Phthalimide
• Bismaleimide
• N-Methylphthalimide
• N-(4-BROMOPHENYL)METHANESULFONAMIDE, 97%
• N-(2-Hydroxyethyl)acrylamide, HEAA
• POLY(ISOBUTYLENE-CO-ISOPRENE), BROMINATED
• (R)-5-PHTHALIMIDO-2-BROMOVALERIC ACID
• N-(4-BROMOBUTOXY)PHTHALIMIDE
• Polyamideimide
• 2-(4-BROMOPENTYL)-1H-ISIONDOLE-1,3(2H)DIONE
• DIALIFOS
• 2-(4-BROMO-3-OXOBUTYL)-1H-ISOINDOLE-1,3(2H)-DIONE
• 2-(4-BROMOBUTYL)-5-NITRO-1H-ISOINDOLE-1,3(2H)-DIONE