Description

N-(4-Bromobutyl)phthalimide (CAS No. 5394-18-3) is a high-purity organic compound with the molecular formula C₁₂H₁₂BrNO₂. This white to off-white crystalline solid is a versatile intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and specialty materials. Its IUPAC name, 2-(4-bromobutyl)isoindole-1,3-dione, reflects its phthalimide-protected bromobutyl functionality, which is highly reactive in nucleophilic substitution reactions. With a molecular weight of 282.13 g/mol, it is soluble in common organic solvents like DMF, DMSO, and THF, but insoluble in water. This compound is ideal for researchers requiring a reliable building block for the synthesis of complex molecules, including active pharmaceutical ingredients (APIs) and functionalized polymers. Store in a cool, dry place, protected from light and moisture to ensure stability.

Properties

• CAS Number: 5394-18-3
• Complexity: 269
• IUPAC Name: 2-(4-bromobutyl)isoindoline-1,3-dione
• InChI: 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
• InChI Key: UXFWTIGUWHJKDD-UHFFFAOYSA-N
• Exact Mass: 281.00514
• Molecular Formula: C12H12BrNO2
• Molecular Weight: 282.13
• SMILES: C1=CC=C2C(=C1)C(=O)N(C2=O)CCCCBr
• Topological: 37.4
• Monoisotopic Mass: 281.00514
• Synonyms: N-(4-Bromobutyl)phthalimide, 5394-18-3, 1H-Isoindole-1,3(2H)-dione, 2-(4-bromobutyl)-, 2-(4-Bromobutyl)-1H-isoindole-1,3(2H)-dione, NSC 575, EINECS 226-401-2, DTXSID40202228, DTXCID40124719, 226-401-2, 2-(4-Bromobutyl)isoindoline-1,3-dione, 2-(4-bromobutyl)isoindole-1,3-dione, MFCD00005905, n-(4-bromobutyl) phthalimide, n-(4-bromobutyl)-phthalimide, 2-(4-bromobutyl)-2,3-dihydro-1H-isoindole-1,3-dione, NSC575, 1-Phthalimido-4-bromobutane; 2-(4-Bromobutyl)-1H-isoindole-1,3(2H)-dione; 2-(4-Bromobutyl)isoindole-1,3-dione; 2-(4-Bromobutyl)phthalimide; 4-Bromobutylphthalimide; NSC 575, N-bromobutylphthalimide, 4-phathalimido bromobutane, 4-phthalimidobutyl bromide, N-(4bromobutyl)phthalimide, N-4-bromobutyl phthalimide, N-4-bromobutyl-phthalimide, N-(4-bromobutyl)phtalimide, N-(4-bromobutyl)phthalimid, 1-Phthalimido-4-bromobutane, SCHEMBL14468, N-(4-bromo-butyl)phthalimide, CHEMBL288310, N-[4-(bromo)butyl]phthalimide, SCHEMBL27473685, UXFWTIGUWHJKDD-UHFFFAOYSA-, N-(4-Bromobut-1-yl)phthalimide, NSC-575, Phthalimide, N-(4-bromobutyl)-, N-(.omega.-Bromobutyl)phthalimide, STR07112, N-(4-Bromobutyl)phthalimide, 98%, SBB070936, AKOS000280838, CS-W018541, FB32709, SB66090, 2-(4-Bromo-butyl)-isoindole-1,3-dione, AC-19618, BP-12758, SY017611, 2-(4-bromobutyl)isoindole-1,3(2H)dione, DB-052432, 2-(4-bromobutyl)benzo[c]azoline-1,3-dione, B1394, NS00022334, EN300-16984, F12368, 2-(4-bromobutyl)-1H-isoindole-1.3(2H)-dione, 2-(4-bromobutyl)-1h -isoindole-1,3(2h)-dione, SR-01000035765, 2-(4-Bromobutyl)-1H-isoindole-1,3(2H)-dione #, SR-01000035765-1, InChI=1/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

Application

N-(4-Bromobutyl)phthalimide is widely used as a key intermediate in organic synthesis, particularly for introducing the 4-bromobutyl moiety into target molecules. It is employed in the preparation of pharmaceuticals, such as GABA receptor modulators and other bioactive compounds. Additionally, it serves as a precursor for the synthesis of functionalized polymers and dendrimers. Researchers also utilize it in cross-coupling reactions and as a building block for advanced material science applications.

Safety and Hazards

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (95.5%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Skin Irrit. 2 (100%)
• Eye Irrit. 2A (100%)
• STOT SE 3 (95.5%)

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