| Identification | More | [Name]
N-(4-Bromobutyl)phthalimide | [CAS]
5394-18-3 | [Synonyms]
2-(4-BROMOBUTYL)-1H-ISOINDOLE-1,3(2H)-DIONE
2-(4-BROMOBUTYL)ISOINDOLINE-1,3-DIONE
AKOS 92204
N-(4-BROMOBUTYL)PHTHALIMIDE
1H-Isoindole-1,3(2H)-dione, 2-(4-bromobutyl)-
1-Phthalimido-4-bromobutane
4-Bromobutylphthalimide
N-(omega-Bromobutyl)phthalimide
Phthalimide, N-(4-bromobutyl)-
N-(4-Bromobutyl)phthalimide, 98+%
2-(4-Bromobutyl)isoindole-1,3-dione
2-(4-Bromobutyl)-2H-isoindole-1,3-dione
N-(4-Brompobutyl)phthalimide | [EINECS(EC#)]
226-401-2 | [Molecular Formula]
C12H12BrNO2 | [MDL Number]
MFCD00005905 | [Molecular Weight]
282.13 | [MOL File]
5394-18-3.mol |
| Chemical Properties | Back Directory | [Appearance]
white crystalline powder | [Melting point ]
76-80 °C (lit.) | [Boiling point ]
165-170°C 1mm | [density ]
1.5271 (rough estimate) | [refractive index ]
1.6320 (estimate) | [Fp ]
165-170°C/1mm | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
Chloroform (Slightly), Methanol (Slightly) | [form ]
Powder | [pka]
-2.15±0.20(Predicted) | [color ]
White to light brown | [Water Solubility ]
Soluble in ethanol. Insoluble in water. | [BRN ]
164119 | [InChI]
1S/C12H12BrNO2/c13-7-3-4-8-14-11(15)9-5-1-2-6-10(9)12(14)16/h1-2,5-6H,3-4,7-8H2 | [InChIKey]
UXFWTIGUWHJKDD-UHFFFAOYSA-N | [SMILES]
O=C1N(CCCCBr)C(C2=CC=CC=C21)=O | [CAS DataBase Reference]
5394-18-3(CAS DataBase Reference) | [NIST Chemistry Reference]
N-(4-bromobutyl)phthalimide(5394-18-3) |
| Hazard Information | Back Directory | [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 |
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