110993-40-3

Basic information

• Product Name: N-TERT-BUTYL-3,5-DIMETHYLANILINE
• Synonyms: N-(1,1-Dimethylethyl)-3,5-dimethyl benzenamine;N-tert-Butyl-3,5-dimethylaniline;N-TERT-BUTYL-3,5-DIMETHYLANILINE;N-TERT-BUTYL-3,5-XYLIDINE
• CAS NO: 110993-40-3
• Molecular Formula: C₁₂H₁₉N
• Molecular Weight: 177.28596
• Product Categories: Amines;Building Blocks;C12;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 110993-40-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 70 °C / 0.8mmHg
• Flash Point: 104 °C
• Appearance: Colorless to brown/Liquid
• Density: 0.901 g/mL at 25 °C
• Vapor Pressure: 0.00802mmHg at 25°C
• Refractive Index: n20/D 1.519
• Storage Temp.: Refrigerator
• CAS DataBase Reference: N-TERT-BUTYL-3,5-DIMETHYLANILINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-TERT-BUTYL-3,5-DIMETHYLANILINE(110993-40-3)
• EPA Substance Registry System: N-TERT-BUTYL-3,5-DIMETHYLANILINE(110993-40-3)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• WGK Germany: 3
• Hazardous Substances Data: 110993-40-3(Hazardous Substances Data)

Usage

Uses

N-tert-Butyl-3,5-Dimethylaniline is used as a reactant in the preparation of a trisamidomolybdenum(VI) propylidyne complex as a highly active catalyst precursor for alkyne metathesis.

InChI:InChI=1/C12H19N/c1-9-6-10(2)8-11(7-9)13-12(3,4)5/h6-8,13H,1-5H3

Upstream product

• 556-96-7 5-bromo-1,3-xylene 
• 76144-87-1 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl 
• 75-64-9 tert-butylamine 
• 773-01-3 2,4,6-trimethylpyrylium tetrafluoroborate 

Downstream Products

• 260265-93-8 lithium N-(3,5-dimethylphenyl)-tert-butylamide etherate 

Relevant articles and documents

Preparation of a trisamidomolybdenum(VI) propylidyne complex a highly active catalyst precursor for alkyne metathesis

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Alkyne metathesis: Development of a novel molybdenum-based catalyst system and its application to the total synthesis of epothilone A and C

Sterically hindered molybdenum(III) amido complexes of the general type [Mo{(tBu)(Ar)N}3] (1), upon treatment with CH2Cl2 or other halogen donors, have been converted into highly effective catalysts for all kinds of alkyne metathesis reactions. Although the actual nature of the propagating species formed in situ is still elusive, halogen transfer to the Mo center of 1 plays a decisive role in the activation of such precatalysts. It was possible to isolate and characterize by X-ray crystallography some of the resulting molybdenum halide derivatives such as 15, 16 and 20 which themselves were shown to be catalytically active. Numerous applications illustrate the performance of the catalytic system 1/CH2Cl2 which operates under mild conditions and tolerates an array of polar functional groups. The wide scope allows the method to be implemented into the total synthesis of sensitive and polyfunctional natural products. Most notable among them is a concise entry into the potent anticancer agents epothilone A (86) and C (88). The macrolide core of these targets is forged by ring closing alkyne metathesis (RCAM) of diyne 113, followed by Lindlar hydrogenation of cycloalkyne 114 thus formed. Since this strategy opens a stereoselective entry into (Z)-alkene 115, the approach is inherently more efficient than previous syntheses based on conventional RCM. Wiley-VCH Verlag GmbH, 2001.

SYNTHESE DE N,N-DIALKYL-3,5-DIALKYL-ANILINES A PARTIR DES SELS DE TRIALKYL-2,4,6-PYRYLIUM

We have optimized through an experimental design the synthesis of N,N-diethyl-3,5-dimethylaniline from 2,4,6-trimethylpyrylium terafluoroborate (I) and diethylamine in a new reaction medium (acetonitrile/triethylamine).Optimal conditions have been applied with high yields to the synthesis of various 3,5-dimethylanilines derived from I and dimethylamine, morpholine, N-methylpiperazine, piperazine, dihexylamine, piperidine, and pyrrolidine respectively. 2-Alkyl-4,6-dimethylpyrylium tetrafluoroborates react regioselectively with diethylamine to afford N,N-diethyl-3-alkyl-5-methyl anilines under these conditions.