14396-90-8

Basic information

• Product Name: N-(3-BUTYNYL)PHTHALIMIDE
• Synonyms: N-(3-BUTYNYL)PHTHALIMIDE;TIMTEC-BB SBB008843;N-(3-Butyn)Phthalamide;2-But-3-ynyl-isoindole-1,3-dione;2-(But-3-yn-1-yl)isoindoline-1,3-dione;N-(3-Butynyl)phthalimide 97%;2-but-3-yn-1-yl-1H-isoindole-1,3(2H)-dione;2-(but-3-ynyl)isoindoline-1,3-dione
• CAS NO: 14396-90-8
• Molecular Formula: C₁₂H₉NO₂
• Molecular Weight: 199.21
• Product Categories: Carbonyl Compounds;Cyclic Imides;Organic Building Blocks
• Mol File: 14396-90-8.mol
• Article Data: 32

Chemical Properties

• Melting Point: 137-142 °C
• Boiling Point: 328 °C at 760 mmHg
• Flash Point: 146.6 °C
• Appearance: /
• Density: 1.269 g/cm³
• Vapor Pressure: 0.000195mmHg at 25°C
• Refractive Index: 1.605
• Storage Temp.: 2-8°C
• PKA: -2.28±0.20(Predicted)
• CAS DataBase Reference: N-(3-BUTYNYL)PHTHALIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(3-BUTYNYL)PHTHALIMIDE(14396-90-8)
• EPA Substance Registry System: N-(3-BUTYNYL)PHTHALIMIDE(14396-90-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36-43
• Safety Statements: 36/37/39
• WGK Germany: 3
• Hazardous Substances Data: 14396-90-8(Hazardous Substances Data)

Usage

General Description

N-(3-Butynyl)phthalimide is a chemical compound with the molecular formula C12H9NO2. It is a phthalimide derivative with a butynyl group attached to the nitrogen atom. N-(3-BUTYNYL)PHTHALIMIDE is mainly used as a reagent in organic synthesis to introduce the butynyl group into various organic molecules. It can also act as a ligand for transition metal complexes, making it useful in catalytic reactions. Additionally, N-(3-Butynyl)phthalimide has been studied for its potential antimicrobial and antifungal properties. However, its full range of applications and potential uses are still being explored.

InChI:InChI=1/C12H9NO2/c1-2-3-8-13-11(14)9-6-4-5-7-10(9)12(13)15/h1,4-7H,3,8H2

Upstream product

• 136918-14-4 phthalimide 
• 927-74-2 3-Butyn-1-ol 
• 38771-21-0 4-bromobut-1-yne 
• 85-44-9 phthalic anhydride 
• 14044-63-4 but-3-yn-1-amine 
• 51908-64-6 4-chlorobut-1-yne 
• 1074-82-4 potassium phtalimide 
• 484673-75-8 C₂₂H₂₀N₂O₂ 
• 23418-85-1 3-butyn-1-yl p-toluenesulfonate 
• 72486-09-0 methanesulfonic acid but-3-ynyl ester 
• 16156-58-4 prop-2-yn-1-ol methanesulfonate 
• 2436-29-5 3-(N-phthaloyl)propionaldehyde 

Downstream Products

• 1060671-67-1 2-{2-[1-(toluene-4-sulphonyl)-1H-indol-2-yl]ethyl}isoindole-1,3-dione 
• 1229971-44-1 (E)-2-(4-(dimethyl(perfluorophenyl)silyl)but-3-enyl)isoindoline-1,3-dione 
• 1229971-47-4 2-(3-(dimethyl(perfluorophenyl)silyl)but-3-enyl)isoindoline-1,3-dione 
• 1875-48-5 N-aminophthalamide 
• 88211-50-1 4-amino-1-butyne hydrochloride 
• 52898-32-5 N-(3-butenyl)phthalimide 
• 1609485-73-5 (E)-2-(6-phenylhex-3-en-5-ynyl)isoindoline-1,3-dione 
• 1609486-08-9 C₂₄H₂₀N₂O₄ 
• 858132-33-9 2-[2-(3-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-2-oxo-2,3-dihydro-furo[2,3-d]pyrimidin-6-yl)-ethyl]-isoindole-1,3-dione 
• 777949-64-1 2-[4-(phenylseleno)but-3-ynyl]-1H-isoindole-1,3(2H)-dione 
• 107301-86-0 2-[2-(5-Methoxy-4-methyl-3,6-dioxo-cyclohexa-1,4-dienyl)-ethyl]-isoindole-1,3-dione 
• 107301-85-9 2-[2-(4-Methoxy-5-methyl-3,6-dioxo-cyclohexa-1,4-dienyl)-ethyl]-isoindole-1,3-dione 
• 125030-48-0 2-[4-[6-(2-Fluorophenyl)-1-methyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-8-yl]-3-butynyl]-1H-isoindole-1,3(2H)-dione 
• 141019-38-7 diethyl N-<4-(4-phthalimidobut-1-ynyl)benzoyl>-L-glutamate 

Relevant articles and documents

Radical Carbonyl Propargylation by Dual Catalysis

Carbonyl propargylation has been established as a valuable tool in the realm of carbon–carbon bond forming reactions. The 1,3-enyne moiety has been recognized as an alternative pronucleophile in the above transformation through an ionic mechanism. Herein, we report for the first time, the radical carbonyl propargylation through dual chromium/photoredox catalysis. A library of valuable homopropargylic alcohols bearing all-carbon quaternary centers could be obtained by a catalytic radical three-component coupling of 1,3-enynes, aldehydes and suitable radical precursors (41 examples). This redox-neutral multi-component reaction occurs under very mild conditions and shows high functional group tolerance. Remarkably, bench-stable, non-toxic, and inexpensive CrCl3 could be employed as a chromium source. Preliminary mechanistic investigations suggest a radical-polar crossover mechanism, which offers a complementary and novel approach towards the preparation of valuable synthetic architectures from simple chemicals.

Facile preparation of 2-aryl-3-iodopyrroles with N-tosyl 4-aryl-3-butyn-1-ylamines, I2, andtBuOK

Treatment of N-tosyl 4-aryl-3-butyn-1-ylamines with I2 and K2CO3, followed by the reaction withtBuOK under mild conditions gave 2-aryl-3-iodopyrroles in good yields. The present approach is a one-pot method for the preparation of 2-aryl-3-iodopyrroles from N-tosyl 4-aryl-3-butyn-1-ylamines, which could be easily prepared from aryl iodides, N-(3-butyn-1-yl)phthalimides, and p-toluenesulfonyl chloride.

Synthesis of Exo- and Endocyclic Enamides Through Copper-Catalyzed Regioselective Intramolecular N-Halovinylation

Cross-couplings between amides and 1,2-dihaloalkenes are an efficient and straightforward way to access β-haloenamides which, in turn, can be functionalized into complex, stereodefined enamide motifs. However, the intramolecular version of these cross-couplings, leading to cyclic β-haloenamides, has not been formally studied. In this paper, we report an investigation of factors affecting the efficiency of the reaction and its selectivity between potential exo and endo cyclization products. We demonstrate that exo/endo selectivity is largely determined by ring strain, whether it arises from the size of the resulting ring or from the structure of the starting compound, but that selectivity can also be modulated by varying reaction conditions. Finally, we show that resulting β-haloenamides readily undergo transition metal-catalyzed reactions, making this sequence a viable way to access highly functionalized cyclic enamides.