72551-10-1

Basic information

• Product Name: N-benzyl-2-bromoprop-2-en-1-amine
• Synonyms: Benzenemethanamine, N-(2-bromo-2-propen-1-yl)-
• CAS NO: 72551-10-1
• Molecular Formula: C₁₀H₁₂BrN
• Molecular Weight: 226.113
• Mol File: 72551-10-1.mol

Chemical Properties

• Boiling Point: 277°C at 760 mmHg
• Flash Point: 121.3°C
• Density: 1.313g/cm³
• Vapor Pressure: 0.00465mmHg at 25°C
• Refractive Index: 1.563
• PKA: 8.57±0.20(Predicted)
• CAS DataBase Reference: N-benzyl-2-bromoprop-2-en-1-amine(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzyl-2-bromoprop-2-en-1-amine(72551-10-1)
• EPA Substance Registry System: N-benzyl-2-bromoprop-2-en-1-amine(72551-10-1)

Safety Data

• Hazardous Substances Data: 72551-10-1(Hazardous Substances Data)

Upstream product

• 100-46-9 benzylamine 
• 513-31-5 2-bromoallyl bromide 

Downstream Products

• 177608-28-5 N,N'-Dibenzyl-2-methylene-propane-1,3-diamine 
• 1197-51-9 N-propargylbenzylamine 
• 188818-06-6 N-benzyl-2-methylene-aziridine 
• 160929-07-7 N-benzyl-N-(2-bromo-2-propen-1-yl)-N-(2-propen-1-yl)amine 
• 1346240-87-6 C₁₃H₁₅NO 
• 101733-53-3 1-benzyl-4-methyl-2-phenyl-1H-pyrrole 
• 92288-02-3 5-methylene-3-(phenylmethyl)-2-oxazolidinone 
• 290301-52-9 3-acetyl-1-benzyl-4-methyl-3-pyrroline 

Relevant articles and documents

Catalytic Enantioselective Synthesis of Amino Skipped Diynes

The Cu-catalyzed synthesis of nonracemic 3-amino skipped diynes via an enantiodetermining C-C bond formation is described using StackPhos as ligand. Despite challenging issues of reactivity and stereoselectivity inherent to these chiral skipped diynes, the reaction tolerates an extremely broad substrate scope with respect to all components and provides the title compounds in excellent enantiomeric excess. The alkyne moieties are demonstrated here to be useful synthetic handles, and 3-amino skipped diynes are convenient building blocks for enantioselective synthesis.

Switchable Copper-Catalyzed Cascade Synthesis of Thiazolidine-2-thiones and Thiazole-2(3 H)-thiones

A novel copper-catalyzed cascade synthesis of thiazolidine-2-thiones from N-(2-bromoallyl)amines and carbon disulfide has been developed. The procedure combines carbamodithioic acid formation and copper-catalyzed intramolecular S-vinylation in one sequence. By elevating the temperature, the one-pot reaction efficiently affords thiazole-2(3H)-thiones in moderate to good yields.

Memory of chirality in rebound cyclizations of α-amide radicals

Reduction of (S)-N-(2-bromoallyl)-N-(tert-butyl)-2-methyl-3- phenylpropanamide with tributyltin hydride provides (3S,4S)-3-benzyl-1-(tert- butyl)-3,4-dimethylpyrrolidin-2-one with about 80% retention of chirality at the stereocenter adjacent to the amide carbonyl group. This memory of chirality is suggested to occur by transfer of chirality from a stereocenter to an axis, then from the axis back to a new stereocenter.

Nickel-catalyzed [3 + 2] cycloaddition of diynes with methyleneaziridines via C-C bond cleavage

A Ni-catalyzed [3 + 2] cycloaddition via C-C bond cleavage of methyleneaziridines under mild conditions was developed. This reaction gave substituted pyrroles with excellent regioselectivity and a pendant alkyne unit, which is advantageous for further derivatization. The Royal Society of Chemistry 2013.

Nickel-catalyzed intramolecular nucleophilic addition of aryl or vinyl chlorides to α-ketoamides through C-Cl bond activation

Nickeleophilic addition! The first example of a nickel-catalyzed direct intramolecular nucleophilic addition of aryl or vinyl chlorides to α-ketoamides through C-Cl bond activation is reported, which takes place under mild reaction conditions (see scheme).

Convenient synthesis of heterobicycles by domino Heck-Diels-Alder reactions

Palladium(0)-catalyzed intramolecular cross coupling of bromodialkenylamines, bromoalkenylalkenamides and bromodialkenyl ethers followed by in situ [4+2] cycloaddition with suitable dienophiles gave tetrahydroisoindolines (31-73%yield), tetrahydroisoindolin-1-ones (43-51%) and hexahydrobenzo[c]furans (35-55%), and hexahydro-1H-[2]pyrindines (66-75%), respectively, each in one-pot operations.

Observations on the ring opening reactions of 2-methyleneaziridines with acid chlorides and alkyl chloroformates

The ring-opening reactions of 2-methylene-aziridines with acid chlorides and alkyl chloroformates were studied. The mechanism suggested that the reactions proceeded by initial N-acylation to form corresponding aziridinium cation. This was followed by regiospecific ring opening by chloride ion at the sp3 hybridized aziridine carbon atom to produce the observed product.

Observations on the synthesis of functionalised methyleneaziridines

N-triphenylmethyl-2-methyleneaziridine 8 was synthesized from N-(2-bromo-2-propenyl)-amine 7 by treatment with sodium amide in liquid ammonia and its structure established using x-ray crystallography. Using modified conditions, (S)-N-(1-phenylethyl)-2-methyleneaziridine 9 was prepared in enantiomerically enriched form. Studies directed towards the synthesis of N-tosyl and N-Boc methyleneaziridines 14 and 15 respectively reveal limitations with this methodology.

Preparation and Reactivity of New β-Nitrogen-Functionalized Vinylic Organolithium Compounds from Secondary Aliphatic Allylamines

Two new types of β-nitrogen-functionalized vinylic organolithium compounds have been prepared from secondary aliphatic allylamines through the temporary silylation of the amino group.The monoanionic intermediates 4, stable at -80 deg C, are generated by a bromine-lithium exchange reaction and the dianionic derivatives 2, stable at room temperature, by a tin-lithium transmetalation reaction.Both types of organolithium compounds react with different electrophiles giving functionalized allylamines 7 and 10-27.Moreover, dianionic derivatives 30,33 can be prepared directly by bromine-lithium exchange when the β-elimination reaction of hydrogen bromide in the lithium 2-bromoallylamide is structurally hindered.Additionally, a novel type of anionic 1,3-rearrangement of a trimethylsilyl group from nitrogen to carbon is described.