N-(3-BROMOPROPYL)PHTHALIMIDE Chemical Properties

Melting point:

72-74 °C(lit.)

Boiling point:

361℃

Density 

1.578

refractive index 

1.6320 (estimate)

Flash point:

172℃

storage temp. 

Inert atmosphere,Room Temperature

solubility 

<1g/l

form 

Crystalline Powder or Crystals

pka

-2.21±0.20(Predicted)

color 

White to light beige

BRN 

157547

InChI

InChI=1S/C11H10BrNO2/c12-6-3-7-13-10(14)8-4-1-2-5-9(8)11(13)15/h1-2,4-5H,3,6-7H2

InChIKey

VKJCJJYNVIYVQR-UHFFFAOYSA-N

SMILES

C1(=O)C2=C(C=CC=C2)C(=O)N1CCCBr

CAS DataBase Reference

5460-29-7(CAS DataBase Reference)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

29251900

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

N-(3-BROMOPROPYL)PHTHALIMIDE Usage And Synthesis

Chemical Properties

white powder

Uses

N-(3-Bromopropyl)phthalimide is used in synthesis of several organic compounds including that of flavonoid derivatives which act as selective ABCC1 modulators with potential use as pharmacological tools for investigation of the role of ABCC1. It is also used in the synthesis of Hederagenin which is a triterpene template for the development of new antitumor compounds.

reaction suitability

reagent type: cross-linking reagent

Synthesis

In 50 mL of DMF, 0.025 mol of phthalimide potassium salt, 0.10 mol of 1,3-dibromopropane and 0.5 g of TBAB were added and the reaction was carried out at 70°C for 2.0 hours. After completion of the reaction, the mixture was cooled to room temperature, poured into ice water and extracted with ethyl acetate. The organic phase was sequentially washed with water, dried, concentrated and allowed to stand overnight to give 5.91 g of N-(3-bromopropyl)phthalimide as a white solid with a melting point of 70-73°C and a yield of 88.3%.

Purification Methods

Place it in a Soxhlet and extract it with Et2O, whereby the bis-phthalimido impurity is not extracted. Evaporate the Et2O and recrystallise the residue from EtOH, aqueous EtOH or pet ether. [Gabriel & Weiner Chem Ber 21 2669 1888, Gaudry Can J Chem 31 1060 1953, Beilstein 21/10 V 1277.]

References

[1] Patent: CN107382980, 2017, A. Location in patent: Paragraph 0035; 0036; 0037; 0038
[2] Patent: CN107540647, 2018, A. Location in patent: Paragraph 0049-0051
[3] European Journal of Medicinal Chemistry, 2018, vol. 149, p. 69 - 78
[4] Chemistry - A European Journal, 2014, vol. 20, # 6, p. 1530 - 1538
[5] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 7, p. 1223 - 1227

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