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

Description

N-(3-Butynyl)phthalimide, a chemical compound with the molecular formula C12H9NO2, is a phthalimide derivative featuring a butynyl group attached to the nitrogen atom. N-(3-BUTYNYL)PHTHALIMIDE is known for its role in organic synthesis, where it serves to introduce the butynyl group into a variety of organic molecules. Its unique structure also allows it to function as a ligand for transition metal complexes, thereby contributing to catalytic reactions. Furthermore, research has indicated its potential in antimicrobial and antifungal applications, although the full spectrum of its uses is still under investigation.

Uses

Used in Organic Synthesis:
N-(3-Butynyl)phthalimide is used as a reagent for introducing the butynyl group into various organic molecules, which is crucial for the synthesis of a range of organic compounds.
Used as a Ligand in Catalysis:
In the field of catalysis, N-(3-Butynyl)phthalimide is utilized as a ligand for transition metal complexes, enhancing the efficiency and selectivity of catalytic reactions.
Used in Antimicrobial and Antifungal Applications:
N-(3-Butynyl)phthalimide has been studied for its potential antimicrobial and antifungal properties, indicating its possible use in pharmaceuticals and other industries where such properties are beneficial.
While the provided materials do not specify different industries for the applications, the general uses listed above can be applicable across various chemical and pharmaceutical industries where organic synthesis, catalysis, and antimicrobial/antifungal agents are required.

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 
• 484673-75-8 C₂₂H₂₀N₂O₂ 
• 23418-85-1 3-butyn-1-yl p-toluenesulfonate 
• 1074-82-4 potassium phtalimide 
• 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 
• 85-44-9 phthalic anhydride 
• 14044-63-4 but-3-yn-1-amine 
• 51908-64-6 4-chlorobut-1-yne 

Downstream Products

• 777949-64-1 2-[4-(phenylseleno)but-3-ynyl]-1H-isoindole-1,3(2H)-dione 
• 1003001-06-6 2-(2-(1-phenyl-1H-[1,2,3]-triazol-5-yl)ethyl)isoindoline-1,3-dione 
• 1060671-67-1 2-{2-[1-(toluene-4-sulphonyl)-1H-indol-2-yl]ethyl}isoindole-1,3-dione 
• 1285573-16-1 2-(2-(3-(perfluorophenyl)isoxazol-5-yl)ethyl)isoindoline-1,3-dione 
• 1262028-98-7 2-[4-(2-phenoxythiazol-4-yl)-3-butynyl]isoindole-1,3-dione 
• 1262028-96-5 2-[4-(2-benzylthiazol-4-yl)-3-butynyl]isoindole-1,3-dione 
• 1262028-93-2 2-[4-(2-phenylthiazol-4-yl)-3-butynyl]isoindole-1,3-dione 
• 1229971-47-4 2-(3-(dimethyl(perfluorophenyl)silyl)but-3-enyl)isoindoline-1,3-dione 
• 1229971-44-1 (E)-2-(4-(dimethyl(perfluorophenyl)silyl)but-3-enyl)isoindoline-1,3-dione 
• 587880-44-2 N-{4-[4-(2-Hydroxyethyloxy)phenyl]but-3-yn-1-yl}phthalimide 
• 144252-28-8 3-ethoxy-3-phenylthio-2-(4-phenylthio-but-3-enyl)-2,3-dihydro-1H-isoindol-1-one 
• 777949-89-0 Se-phenyl 4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)butaneselenoate 
• 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 

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.

Design, synthesis and structure-activity relationships of novel 15-membered macrolides: Quinolone/quinoline-containing sidechains tethered to the C-6 position of azithromycin acylides

In the search for novel hybrid molecules by fusing two biologically active scaffolds into one heteromeric chemotype, we found that hybrids of azithromycin and ciprofloxacin/gatifloxacin 26j and 26l can inhibit the supercoiling activity of E. coli gyrase by poisoning it in a way similar to fluoroquinolones. This may modestly contribute to their potencies, which are equal to ciprofloxacin against constitutively resistant Staphylococcus aureus, whose growth is not inhibited by the presence of macrolides. In contrast, introduction of quinolines (the 3-quinoline 26b and the 6-quinoline 26o) with an optimized rigid spacer at the 6-OH of azithromycin acylides did not exert significant potency against constitutively resistant S. aureus, despite the fact that the quinoline-containing compounds, exemplified by 26o, were as active as telithromycin against susceptible, inducibly- and efflux-resistant pathogens. The novel dual modes of action involving protein synthesis inhibition and poisoning DNA replication may pave the way for restoration of antibacterial activities of the current macrolides against constitutively resistant clinical isolates.