10108-61-9

Basic information

• Product Name: N-sec-butylphthalimide
• Synonyms: N-sec-butylphthalimide;1H-Isoindole-1,3(2H)-dione, 2-(1-methylpropyl)-;2-(1-methylpropyl)-1h-isoindole-3(2h)-dione;2-sec-butyl-isoindole-1,3-dione;n-sec-butyl-phthalimid;n-sek.butylftalimid;2-(sec-Butyl)isoindoline-1,3-dione
• CAS NO: 10108-61-9
• Molecular Formula: C₁₂H₁₃NO₂
• Molecular Weight: 203.23712
• EINECS: 233-295-1
• Mol File: 10108-61-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: 33-35 °C
• Boiling Point: 341.55°C (rough estimate)
• Flash Point: 126°C
• Appearance: /
• Density: 1.1255 (rough estimate)
• Vapor Pressure: 0.00097mmHg at 25°C
• Refractive Index: 1.5260 (estimate)
• Storage Temp.: 2-8°C
• PKA: -2.09±0.20(Predicted)
• CAS DataBase Reference: N-sec-butylphthalimide(CAS DataBase Reference)
• NIST Chemistry Reference: N-sec-butylphthalimide(10108-61-9)
• EPA Substance Registry System: N-sec-butylphthalimide(10108-61-9)

Safety Data

• Hazardous Substances Data: 10108-61-9(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthesis, p. 332, 1986 DOI: 10.1055/s-1986-31605

InChI:InChI=1/C12H13NO2/c1-3-8(2)13-11(14)9-6-4-5-7-10(9)12(13)15/h4-8H,3H2,1-2H3

Upstream product

• 108848-26-6 N-((S)-2-[1,3]dithiolan-2-yl-1-methyl-ethyl)-phthalimide 
• 1074-82-4 potassium phtalimide 
• 78-76-2 s-butyl bromide 
• 136918-14-4 phthalimide 
• 126114-17-8 O-2-Butyl-N,N'-dicyclohexylisourea 
• 33966-50-6 SEC-BUTYLAMINE 
• 26268-95-1 N-propionylphthalimide 
• 109722-87-4 N-methylsulfonylphthalimide 
• 1971-49-9 N-acetylphthalimide 
• 42945-18-6 2-(1-hydroxybutan-2-yl)isoindoline-1,3-dione 
• 66072-87-5 N-[1-(toluene-4-sulfonyloxymethyl)-propyl]-phthalimide 
• 85-44-9 phthalic anhydride 
• 98289-79-3 1-iodo-2-phthalimidobutane 
• 513-49-5 (S)-2-aminobutane 

Downstream Products

• 69338-48-3 N-sec-butyl-phthalamic acid 

Relevant articles and documents

Nucleophilic substitution of (alkoxymethylene)dimethylammonium chloride with potassium phthalimide; a convenient procedure for the synthesis of imides with inversion of configuration

Secondary alcohols are converted into their phthalimido derivatives with inversion of configuration via sequential reaction with (chloromethylene)dimethylammonium chloride and potassium phthalimide.

Synthesis and evaluation of some variants of the Nefkens' reagent

A series of N-substituted phthalimides have been prepared in an effort to explore synthetic variants of the Nefkens' reagent. Three N-acylphthalimides [R = -CH3, -CH2CH3, and -C(CH3) 3] were prepared and employed for the protection of a series of representative amines. In addition, an N-methanesulfonylphthalimide and N-(diethylphosphoryl)phthalimide were also prepared. It was determined that among the phthalimides that were prepared N-propanoylphthalimide was the most effective reagent for the protection reaction.

Nucleophilic Substitution Reactions of (Alkoxymethylene)dimethylammonium Chloride

The use of imidate esters as potential replacements for diethyl azodicarboxylate and triphenylphosphine in the Mitsunobu reaction is described. A series of secondary alcohols were allowed to react with (chloromethylene)dimethylammonium chloride, generated from dimethylformamide (DMF) and oxalyl chloride, to give imidate esters. Reaction of these salts with potassium benzoate or potassium phthalimide gave the products of SN2 substitution in excellent yields with clean inversion of stereochemistry. Optimization of reaction conditions is discussed as a means to increase the atom economy of the process by minimizing the quantity of nucleophile required.