79293-84-8

Basic information

• Product Name: N-(TERT-BUTYLDIMETHYLSILYL)PHTHALIMIDE
• Synonyms: N-(TERT-BUTYLDIMETHYLSILYL)PHTHALIMIDE;N-(T-BUTYLDIMETHYLSILYL)PHTHALIMIDE
• CAS NO: 79293-84-8
• Molecular Formula: C₁₄H₁₉NO₂Si
• Molecular Weight: 261.39
• Product Categories: Carbonyl Compounds;Cyclic Imides;Organic Building Blocks
• Mol File: 79293-84-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 115-119 °C(lit.)
• Boiling Point: 336°C at 760 mmHg
• Flash Point: 157°C
• Appearance: /
• Density: 1.09g/cm³
• Vapor Pressure: 0.000116mmHg at 25°C
• Refractive Index: 1.537
• PKA: -1.95±0.20(Predicted)
• CAS DataBase Reference: N-(TERT-BUTYLDIMETHYLSILYL)PHTHALIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(TERT-BUTYLDIMETHYLSILYL)PHTHALIMIDE(79293-84-8)
• EPA Substance Registry System: N-(TERT-BUTYLDIMETHYLSILYL)PHTHALIMIDE(79293-84-8)

Safety Data

• WGK Germany: 3
• TSCA: No
• Hazardous Substances Data: 79293-84-8(Hazardous Substances Data)

Usage

General Description

N-(tert-butyldimethylsilyl)phthalimide is an organosilicon compound used as a reagent in organic synthesis. It is a colorless solid that is soluble in organic solvents. N-(TERT-BUTYLDIMETHYLSILYL)PHTHALIMIDE is commonly used in the protection of amines during chemical reactions and as a precursor for the synthesis of various organic compounds. The tert-butyldimethylsilyl (TBS) group serves as a protecting group for amines, allowing for selective manipulation of other functional groups in the molecule. N-(tert-butyldimethylsilyl)phthalimide is a valuable tool for the preparation of complex organic molecules in a controlled and efficient manner.

InChI:InChI=1/C14H19NO2Si/c1-14(2,3)18(4,5)15-12(16)10-8-6-7-9-11(10)13(15)17/h6-9H,1-5H3

Synthetic route

phthalimide (136918-14-4) + ketene t-butyldimethylsilyl methyl acetal (77086-38-5) → N-(tert-butyldimethylsilyl)phthalimide (79293-84-8)

Conditions	Yield
In acetonitrile at 60℃; for 0.25h;	77%

phthalimide (136918-14-4) + tert-butyldimethylsilyl chloride (18162-48-6) → N-(tert-butyldimethylsilyl)phthalimide (79293-84-8)

Conditions	Yield
With triethylamine In dichloromethane for 6h; Heating;	71%
With triethylamine In dichloromethane at 20℃; for 4.5h;	65%

N-(trimethylsilyl)phthalimide (10416-67-8) → N-(tert-butyldimethylsilyl)phthalimide (79293-84-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrahydrofuran / 20 °C 2: triethylamine / dichloromethane / 4.5 h / 20 °C View Scheme

3-(2-bromoethyl)-4-(phenylsulfonyl)-1,2,5-oxadiazole (906096-91-1) + N-(tert-butyldimethylsilyl)phthalimide (79293-84-8) → 2-{2-[4-(phenylsulfonyl)-1,2,5-oxadiazol-3-yl]ethyl}-1H-isoindole-1,3(2H)-dione (906096-92-2)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 3h; Heating;	92%

N-(tert-butyldimethylsilyl)phthalimide (79293-84-8) + methyl 2-[fluoro(phenyl)methyl]acrylate (203392-27-2) → methyl 2-((1,3-dioxoisoindolin-2-yl)(phenyl)methyl)acrylate

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In dichloromethane at 25℃; regioselective reaction;	90%

diethyl (bromomethyl)phosphonate (66197-72-6) + N-(tert-butyldimethylsilyl)phthalimide (79293-84-8) → diethyl (phthalimidomethyl)phosphonate (33512-26-4)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 12h; Heating;	85%

diethyl 2-bromoethylphosphonate (5324-30-1) + N-(tert-butyldimethylsilyl)phthalimide (79293-84-8) → [2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)ethyl]phosphonic acid diethyl ester (62514-90-3)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 8h; Heating;	84%

N-(tert-butyldimethylsilyl)phthalimide (79293-84-8) + 6-chloro-2-fluoro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine (13276-51-2) → 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-2-fluoro-6-phthalimido-9H-purine + 9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-6-chloro-2-phthalimido-9H-purine

Conditions	Yield
With cesium fluoride In N,N-dimethyl-formamide at 20℃; for 24h;	A 4% B 84%
With 4 A molecular sieve; tetrabutyl ammonium fluoride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 24h;	A 19% B 57%

diethyl 3-(bromopropyl)phosphonic acid (1186-10-3) + N-(tert-butyldimethylsilyl)phthalimide (79293-84-8) → [3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)propyl]phosphonic acid diethyl ester (107257-50-1)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran for 8h; Heating;	79%

Upstream product

• 10416-67-8 N-(trimethylsilyl)phthalimide 
• 136918-14-4 phthalimide 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 77086-38-5 ketene t-butyldimethylsilyl methyl acetal 

Downstream Products

• 906096-92-2 2-{2-[4-(phenylsulfonyl)-1,2,5-oxadiazol-3-yl]ethyl}-1H-isoindole-1,3(2H)-dione 
• 21708-28-1 N-[2-(6-amino-purin-9-yl)-ethyl]-phthalimide 
• 20245-85-6 9-vinyladenine 
• 74247-81-7 6-O-tert-butyldimethylsilanyl-1-O-methyl-α-D-mannopyranoside 
• 86791-02-8 diethyl (4-(1,3-dioxoisoindolin-2-yl)butyl)phosphonate 
• 33512-26-4 diethyl (phthalimidomethyl)phosphonate 
• 62514-90-3 [2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)ethyl]phosphonic acid diethyl ester 

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.

O-Silylated Ketene Acetal Chemistry; A Mild and Efficient t-Butyldimethylsilylating Agent

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