10416-67-8

Basic information

• Product Name: N-TRIMETHYLSILYLPHTHALIMIDE
• Synonyms: N-TRIMETHYLSILYLPHTHALIMIDE;1H-Isoindole-1,3(2H)-dione, 2-(trimethylsilyl)-;Einecs 233-893-2;Nsc 252169;Phthalimide, N-(trimethylsilyl)- (8ci);2-(Trimethylsilyl)-1H-isoindole-1,3(2H)-dione
• CAS NO: 10416-67-8
• Molecular Formula: C₁₁H₁₃NO₂Si
• Molecular Weight: 219.31
• EINECS: 233-893-2
• Mol File: 10416-67-8.mol
• Article Data: 11

Chemical Properties

• Melting Point: 66-67 °C
• Boiling Point: 300.3°Cat760mmHg
• Flash Point: 135.4°C
• Appearance: /
• Density: 1.15g/cm³
• Vapor Pressure: 0.00113mmHg at 25°C
• Refractive Index: 1.554
• PKA: -1.79±0.20(Predicted)
• CAS DataBase Reference: N-TRIMETHYLSILYLPHTHALIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-TRIMETHYLSILYLPHTHALIMIDE(10416-67-8)
• EPA Substance Registry System: N-TRIMETHYLSILYLPHTHALIMIDE(10416-67-8)

Safety Data

• Hazardous Substances Data: 10416-67-8(Hazardous Substances Data)

Usage

General Description

N-Trimethylsilylphthalimide, also known as TMS phthalimide, is an organosilicon compound used as a reagent in organic synthesis. It is commonly used for the transformation of alcohols into silyl ethers, and for the protection of amino groups in peptides and amino acids. TMS phthalimide can also be used as a precursor in the synthesis of various pharmaceuticals and fine chemicals. N-TRIMETHYLSILYLPHTHALIMIDE is known for its stability and compatibility with a wide range of reaction conditions, making it a valuable tool in synthetic organic chemistry.

InChI:InChI=1/C11H13NO2Si/c1-15(2,3)12-10(13)8-6-4-5-7-9(8)11(12)14/h4-7H,1-3H3

Upstream product

• 136918-14-4 phthalimide 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 85-44-9 phthalic anhydride 
• 100-42-5 styrene 
• 7677-24-9 trimethylsilyl cyanide 
• 422508-64-3 1,3-dioxoisoindolin-2-yl 2,3,4,5,6-pentafluorobenzoate 
• 1538551-54-0 1,3-dioxoisoindolin-2-yl butyrate 
• 24182-36-3 [(1Z)-2-bromobuta-1,3-dien-1-yl]benzene 
• 75-77-4 chloro-trimethyl-silane 
• 1074-82-4 potassium phtalimide 

Downstream Products

• 1041262-70-7 (1R,4S,5S)-ethyl 5-(1,3-dioxoisoindolin-2-yl)-1-(pentan-3-yloxy)-4-(2-(trimethylsilyl)ethylsulfonamido)cyclohex-2-enecarboxylate 
• 1041262-66-1 ethyl (3R,4R,5S)-5-(1,3-dioxoisoindolin-2-yl)-3-(pentan-3-yloxy)-4-[2-(trimethylsilyl)ethylsulfonamido]cyclohex-1-enecarboxylate 
• 1041262-67-2 ethyl (3R,4R,5S)-5-(1,3-dioxoisoindolin-2-yl)-3-(pentan-3-yloxy)-4-{N-[2-(trimethylsilyl)ethylsulfonyl]acetamido}cyclohex-1-enecarboxylate 
• 1041262-68-3 (3R,4R,5S)-4-acetamido-5-(1,3-dioxoisoindol-2-yl)-3-(pentyl-3-yloxy)cyclohexyl-ethyl-1-ene-1-carboxylate 
• 1041262-63-8 ethyl (5S)-5-(1,3-dioxoisoindolin-2-yl)-1-(phenylthio)cyclohex-3-enecarboxylate 
• 1041262-64-9 ethyl (5S)-5-(1,3-dioxoisoindolin-2-yl)cyclohexa-1,3-dienecarboxylate 
• 1291089-98-9 (3R,4R,5S)-ethyl 5-(1,3-dioxoisoindolin-2-yl)-4-(4-methylphenylsulfonamido)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate 
• 1291089-92-3 C₂₄H₂₄N₂O₆S 
• 1291089-94-5 C₂₄H₂₆N₂O₇S 
• 1291089-91-2 (1S,3R,5S,6R)-ethyl 5-(1,3-dioxoisoindolin-2-yl)-7-tosyl-7-aza-bicyclo[4.1.0]heptane-3-carboxylate 
• 1291090-01-1 C₂₃H₂₁NO₄Se 
• 1291089-93-4 (1R,3S,4R,5R)-ethyl 3-(1,3-dioxoisoindolin-2-yl)-5-hydroxy-4-(4-methylphenylsulfonamido)cyclohexanecarboxylate 
• 1291089-95-6 (1R,3S,4R)-ethyl 3-(1,3-dioxoisoindolin-2-yl)-4-(4-methylphenylsulfonamido)-5-oxocyclohexanecarboxylate 
• 1041262-62-7 ethyl (1S,5S)-5-(1,3-dioxoisoindolin-2-yl)cyclohex-3-enecarboxylate 

Relevant articles and documents

Strong influence of intramolecular Si?O proximity on reactivity: Systematic molecular structure, solvolysis, and mechanistic study of cyclic N-trimethylsilyl carboxamide derivatives

A comparative alcoholysis study of N-silylated derivatives of simple heterocyclic carboxamides (lactams, imides, ureas) is presented. The second-order rate constant values span a range as wide as three orders of magnitude. On the basis of DFT calculations, a good correlation between reactivity and the Si?O distance was found within each family of compounds. The viability of two different reaction pathways was evaluated using a detailed computational mechanistic study of the methanolysis of cyclic urea homologues. Peculiarities in the single-crystal X-ray diffraction structures of the trimethylsilyl and trimethylsiloxy phthalimides are also discussed.

Selective C=O reduction in phthalimide with nickel(0) compounds

The catalytic reduction of phthalimide was achieved using nickel catalysts. The use of catalytic amounts (20% mol) of [Ni(COD)2] or [(dippe)Ni(μ-H)]2 (1) allowed the monoreduction of phthalimide to yield isoindolinone and benzamide, at 140-180 C and 750 psi of H2. When the N-H moiety of phthalimide was protected with a trimethylsilyl group, both C=O groups were reduced to yield (trimethylsilyl)isoindoline. However, when a methyl moiety was used as the protecting group, the C=O groups and the aromatic ring were reduced, using rather similar reaction conditions, due to the formation of 5 A (average) nickel nanoparticles.

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Enantioselective Radical Carbocyanation of 1,3-Dienes via Photocatalytic Generation of Allylcopper Complexes

1,3-Dienes are readily available feedstocks that are widely used in the laboratory and industry. However, the potential of converting 1,3-dienes into value-Added products, especially chiral products, has not yet been fully exploited. By synergetic photoredox/copper catalysis, we achieve the first visible-light-induced, enantioselective carbocyanation of 1,3-dienes by using carboxylic acid derivatives and trimethylsilyl cyanide. Under mild and neutral conditions, a diverse range of chiral allyl cyanides are produced in generally good efficiency and with high enantioselectivity from bench-stable and user-safe chemicals. Moreover, preliminary results also confirm that this success can be expanded to 1,3-enynes and the four-component carbonylative carbocyanation of 1,3-dienes and 1,3-enynes.