104937-87-3

Basic information

• Product Name: Benzenemethanamine, N-(1,1-dimethyl-2-propenyl)-
• CAS NO: 104937-87-3
• Molecular Formula: C12H17N
• Molecular Weight: 175.274
• Mol File: 104937-87-3.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: Benzenemethanamine, N-(1,1-dimethyl-2-propenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenemethanamine, N-(1,1-dimethyl-2-propenyl)-(104937-87-3)
• EPA Substance Registry System: Benzenemethanamine, N-(1,1-dimethyl-2-propenyl)-(104937-87-3)

Safety Data

• Hazardous Substances Data: 104937-87-3(Hazardous Substances Data)

Upstream product

• 556-82-1 3-methyl-2-buten-1-ol 
• 116504-03-1 prenyl ethyl carbonate 
• 100-46-9 benzylamine 
• 217189-21-4 N-benzyl-N-(1,1-dimethylallyl)hydroxylamine 
• 463299-27-6 3-benzyl-4,4,5-trimethyl-oxazolidine-2,2-dioxide 
• 88927-34-8 methyl (3-methylbut-2-en-1-yl) carbonate 
• 69690-81-9 <(3-methyl-2-butenyl)seleno>benzene 
• 24509-88-4 2-methyl-3-buten-2-yl acetate 
• 1191-16-8 3-methylbut-2-enyl acetate 
• 463299-25-4 3-benzyl-4,4,5-trimethyl-oxathiazolidine-2-oxide 
• 463299-23-2 3-(benzylamino)-3-methylbutan-2-ol 
• 100-52-7 benzaldehyde 
• 13325-14-9 3-amino-3-methylbutan-2-ol 
• 932-90-1 syn-benzaldehyde oxime 

Downstream Products

• 849935-90-6 N-allyl-N-benzyl-α,α-dimethylallylamine 
• 1044262-08-9 1-benzyl-3-(4-methoxyphenyl)-1-(2-methylbut-3-en-2-yl)urea 
• 145593-39-1 N-Benzyl-2,2,2-trichloro-N-(1,1-dimethyl-allyl)-acetamide 

Relevant articles and documents

Palladium/BINAP(S)-catalyzed asymmetric allylic amination

(Chemical Equation Presented) The enantioselective allylic amination of acyclic allylic carbonates catalyzed by a palladium/(S)-BINAP(S) system was investigated. Amination of several substrates proceeded with high ee. Crotyl carbonates show an unusually high regioselectivity for the branched isomer. The use of (S)-TolBINAP(S) and (S)-3,5-xylyl-BINAP(S) as ligands was found to increase the enantioselectivity of the aminations. A P,S binding mode of the BINAP(S) ligand was found in an X-ray crystallographic study.

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).

Stereoselective synthesis of imidazolidin-2-ones via Pd-catalyzed alkene carboamination. Scope and limitations

A method for the synthesis of imidazolidin-2-ones from N-allylureas and aryl or alkenyl bromides via Pd-catalyzed carboamination reactions is described. The N-allylurea precursors are prepared in one step from readily available allylic amines and isocyanates, and the Pd-catalyzed reactions effect the formation of a C-C bond, a C-N bond, and up to two stereocenters in a single step. Good diastereoselectivities are obtained for the conversion of substrates bearing allylic substituents to 4,5-disubstituted imidazolidin-2-ones, and excellent selectivity for the generation of products resulting from syn-addition across the alkene is observed when substrates derived from cyclic alkenes or E-1,2-disubstituted alkenes are employed. A brief discussion of reaction mechanism and product stereochemistry is presented.