22774-81-8

Basic information

• Product Name: N-(2-methylprop-2-en-1-yl)aniline
• Synonyms: benzenamine, N-(2-methyl-2-propen-1-yl)-
• CAS NO: 22774-81-8
• Molecular Formula: C₁₀H₁₃N
• Molecular Weight: 147.2169
• Mol File: 22774-81-8.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 238.7°C at 760 mmHg
• Flash Point: 98.3°C
• Density: 0.96g/cm³
• Vapor Pressure: 0.0418mmHg at 25°C
• Refractive Index: 1.556
• CAS DataBase Reference: N-(2-methylprop-2-en-1-yl)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-methylprop-2-en-1-yl)aniline(22774-81-8)
• EPA Substance Registry System: N-(2-methylprop-2-en-1-yl)aniline(22774-81-8)

Safety Data

• Hazardous Substances Data: 22774-81-8(Hazardous Substances Data)

Upstream product

• 62-53-3 aniline 
• 563-47-3 3-Chloro-2-methylpropene 
• 513-42-8 3-hydroxy-2-methyl-1-propene 
• 116-11-0 2-Methoxypropene 
• 100-61-8 N-methylaniline 
• 513-31-5 2-bromoallyl bromide 
• 60700-13-2 N-Trimethylsilyl-N-phenylformamide 
• 142820-20-0 2-methylallyl methanesulfonate 
• 118793-05-8 [2-Methyl-prop-2-en-(E)-ylidene]-phenyl-amine 
• 20443-63-4 3-benzenesulfonyloxy-2-methyl-propene 

Downstream Products

• 62420-79-5 N-Methallyl-N-phenylthiocarbamidsaeure-O-ethylester 
• 910619-00-0 N-phenyl-4-methylpyrrolidine-3-carbaldehyde 
• 910618-98-3 N-phenyl-4-methylpyrrolidine-2-carbaldehyde 
• 85692-13-3 4-methyl-N-phenyl-Δ³-pyrroline-2-one 
• 55110-58-2 3-methyl-1-phenyl-2,5-dihydro-1H-pyrrole 
• 30439-01-1 N,N-bis-(2-methylprop-2-enyl)aniline 
• 1282060-72-3 C₁₇H₁₆N₂O 
• 908098-99-7 C₁₇H₁₈N₂O 

Relevant articles and documents

A Simple, Broad-Scope Nickel(0) Precatalyst System for the Direct Amination of Allyl Alcohols

The preparation of allylic amines is traditionally accomplished by reactions of amines with reactive electrophiles, such as allylic halides, sulfonates, or oxyphosphonium species; such methods involve hazardous reagents, generate stoichiometric waste streams, and often suffer from side reactions (such as overalkylation). We report here the first broad-scope nickel-catalysed direct amination of allyl alcohols: An inexpensive NiII/Zn couple enables the allylation of primary, secondary, and electron-deficient amines without the need for glove-box techniques. Under mild conditions, primary and secondary aliphatic amines react smoothly with a range of allyl alcohols, giving secondary and tertiary amines efficiently. This “totally catalytic” method can also be applied to electron-deficient nitrogen nucleophiles; the practicality of the process was demonstrated in an efficient, gram-scale preparation of the calcium antagonist drug substance flunarizine (Sibelium).

Palladium-catalyzed oxidative arylacetoxylation of alkenes: Synthesis of indole and indoline derivatives

A method for the oxidative arylacetoxylation of alkenes has been developed to synthesize indole and indoline derivatives from readily accessible substrates. The cinnamyl tethered anilines with picolinamide as a directing group provided 3-substituted indoles via intramolecular oxidative arylacetoxylation, and the 2-methyl substituted cinnamyl anilines furnished indoline derivatives with 3-position quaternary stereocenters in good to excellent yields via sequential intramolecular oxidative arylacetoxylation, hydrolysis and oxidation steps.

Silver-promoted (radio)fluorination of unsaturated carbamates via a radical process

The intramolecular fluorocyclization of unsaturated carbamates is described here using a hypervalent iodine reagent in the presence of a silver catalyst. Both (hetero)aryl-substituted olefins and acrylamides can be utilized as effective substrates. Preliminary mechanistic investigations suggest that the reaction proceeds via a cyclization/1,2-(hetero)aryl migration/fluorination cascade involving an unusual radical process. Furthermore, starting from no-carrier-added [18F]TBAF, a simple one-pot, two-step cascade method was developed for the generation of 18F-labeled heterocycles with high radiochemical purity.