18042-62-1

Basic information

• Product Name: N-(TRIMETHYLSILYLMETHYL)PHTHALIMIDE
• Synonyms: N-(TRIMETHYLSILYLMETHYL)PHTHALIMIDE;N-(TRIMETHYLSILYMETHYL)PHTHALIMIDE);Phthalimidomethyl-trimethylsilane;2-(trimethylsilylmethyl)isoindole-1,3-dione
• CAS NO: 18042-62-1
• Molecular Formula: C₁₂H₁₅NO₂Si
• Molecular Weight: 233.3385
• Mol File: 18042-62-1.mol
• Article Data: 1

Chemical Properties

• Melting Point: 25-27 °C(lit.)
• Boiling Point: 76-77 °C0.01 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /solid
• Density: 1.116g/cm³
• Vapor Pressure: 7.79E-05mmHg at 25°C
• Refractive Index: 1.534
• PKA: -2.03±0.20(Predicted)
• CAS DataBase Reference: N-(TRIMETHYLSILYLMETHYL)PHTHALIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(TRIMETHYLSILYLMETHYL)PHTHALIMIDE(18042-62-1)
• EPA Substance Registry System: N-(TRIMETHYLSILYLMETHYL)PHTHALIMIDE(18042-62-1)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 21
• Hazardous Substances Data: 18042-62-1(Hazardous Substances Data)

Usage

General Description

N-(Trimethylsilylmethyl)phthalimide is a chemical compound with the molecular formula C12H15NO2Si. It is commonly used as a reagent in organic synthesis, particularly in the preparation of amide and imide compounds. N-(TRIMETHYLSILYLMETHYL)PHTHALIMIDE is a phthalimide derivative with a trimethylsilylmethyl group attached to the nitrogen atom, which imparts unique chemical properties and reactivity. N-(Trimethylsilylmethyl)phthalimide is often used in the context of protecting groups and as a precursor for various organic transformations. It is a versatile and useful reagent in modern organic chemistry, allowing for the efficient and selective formation of complex organic molecules.

InChI:InChI=1/C12H15NO2Si/c1-16(2,3)8-13-11(14)9-6-4-5-7-10(9)12(13)15/h4-7H,8H2,1-3H3

Upstream product

• 136918-14-4 phthalimide 
• 2344-80-1 Chloromethyltrimethylsilane 

Downstream Products

• 17899-13-7 N,N'-Bis-(trimethylsilylmethyl)-phthalamid 
• 550-44-7 N-methylphthalimide 
• 100423-01-6 1-(2-furyl)-2-phthalimidoethanol 
• 100423-02-7 N-(2-hydroxy-4-phenyl-3-butenyl)phthalimide 
• 153397-44-5 1-Hydroxy-1-phenyl-2-<(trimethylsilyl)methyl>isoindolinone 
• 153397-47-8 1-Hydroxy-1-(2-methylphenyl)-2-<(trimethylsilyl)methyl>isoindolinone 
• 153397-46-7 1-Hydroxy-1-<4-(trifluoromethyl)phenyl>-2-<(trimethylsilyl)methyl>isoindolinone 
• 153397-45-6 1-Hydroxy-1-(4-methoxyphenyl)-2-<(trimethylsilyl)methyl>isoindolinone 
• 100422-99-9 2-(2-hydroxy-2-p-tolyl-ethyl)-isoindole-1,3-dione 
• 35645-98-8 2-(2-hydroxy-2-phenyl-ethyl)-isoindole-1,3-dione 
• 100423-00-5 2-(2-hydroxy-2-(4-methoxy-phenyl)-ethyl)-isoindole-1,3-dione 
• 100423-04-9 3,3-dimethyl-1-phthalimido-2-butanol 
• 100423-03-8 N-(2-hydroxy)pentylphthalimide 
• 153489-36-2 2,2-Dimethyl-9b-trimethylsilanyloxy-2,3-dihydro-9bH-oxazolo[2,3-a]isoindol-5-one 

Relevant articles and documents

Metal-Free Aminomethylation of Aromatic Sulfones Promoted by Eosin Y

A metal-free α-aminomethylation of heteroaryls promoted by eosin Y under green light irradiation is reported. A large variety of α-trimethylsilylamines as precursor of α-aminomethyl radical species were engaged to functionalize sulfonyl-heteroaryls following a Homolytic Aromatic Substitution (HAS) pathway. This method has provided a range of α-aminoheteroaryl compounds including a functionalized natural product. The mechanism of this late-stage functionalization of aryls was investigated and suggests the formation of a sulfonyl radical intermediate over a reductive quenching cycle.