115224-13-0

Basic information

• Product Name: (R)-A-PHENYL-3-BUTENAMINE
• Synonyms: (R)-A-PHENYL-3-BUTENAMINE;(1R)-1-PHENYLBUT-3-EN-1-AMINE;(1R)-1-PHENYLBUT-3-EN-1-AMINE-HCL
• CAS NO: 115224-13-0
• Molecular Formula: C₁₀H₁₃N
• Molecular Weight: 147.22
• Mol File: 115224-13-0.mol

Chemical Properties

• Boiling Point: 219.7°C at 760 mmHg
• Flash Point: 90.9°C
• Appearance: /
• Density: 0.951g/cm³
• Vapor Pressure: 0.118mmHg at 25°C
• Refractive Index: 1.536
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: (R)-A-PHENYL-3-BUTENAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-A-PHENYL-3-BUTENAMINE(115224-13-0)
• EPA Substance Registry System: (R)-A-PHENYL-3-BUTENAMINE(115224-13-0)

Safety Data

• Hazardous Substances Data: 115224-13-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-A-PHENYL-3-BUTENAMINE is used as an intermediate for the synthesis of various drugs, including potential antitumor and antidepressant medications. Its chiral nature allows for the development of targeted therapies that can selectively interact with specific biological targets, improving the efficacy and safety of these medications.
Used in Agrochemical Industry:
(R)-A-PHENYL-3-BUTENAMINE is also used as an intermediate in the synthesis of agrochemicals, contributing to the development of more effective and selective pesticides and other agricultural products.
Used in Organic Chemistry:
(R)-A-PHENYL-3-BUTENAMINE serves as a key building block in the synthesis of chiral ligands and catalysts for asymmetric transformations in organic chemistry. These chiral catalysts and ligands are essential for the production of enantiomerically pure compounds, which are crucial in various applications, including pharmaceuticals, fragrances, and agrochemicals.

InChI:InChI=1/C10H13N/c1-2-6-10(11)9-7-4-3-5-8-9/h2-5,7-8,10H,1,6,11H2/t10-/m1/s1

Upstream product

• 120419-97-8 (E)-N-benzylidene-1,1,1-trimethylsilanamine 
• 107-05-1 3-chloroprop-1-ene 
• 53075-84-6 benzaldehyde (E)-N-benzenesulfenylimine 
• 85116-38-7 (+)-diisopinocampheylallylborane 
• 688-61-9 Triallylborane 
• 17599-61-0 N-benzylidene-1,1,1-trimethylsilanamine 
• 211869-53-3 (4S,5R)-2-Allyl-4-methyl-5-phenyl-3-(toluene-4-sulfonyl)-[1,3,2]oxazaborolidine 
• 211869-54-4 (1R,2S,6R,7S)-4-Allyl-1,10,10-trimethyl-5-(toluene-4-sulfonyl)-3-oxa-5-aza-4-bora-tricyclo[5.2.1.0^2,6]decane 
• 211869-55-5 (1R,2R,6S,7S)-4-Allyl-1,10,10-trimethyl-5-(toluene-4-sulfonyl)-3-oxa-5-aza-4-bora-tricyclo[5.2.1.0^2,6]decane 
• 120420-06-6 N-t-butyldimethylsilyl benzaldimine 
• 595565-82-5 (R)-acetic acid N'-(1-phenylbut-3-enyl)-hydrazide 
• 106356-53-0 B-allyldiisopinocampheylborane 

Downstream Products

• 867193-39-3 ethyl 2-({[(1S)-1-phenylbut-3-enyl]amino}methyl)acrylate 
• 679430-63-8 C₂₁H₃₁N₃O₄ 
• 949021-19-6 (S)-N-(1-phenyl-3-buten-1-yl)propenamide 
• 135865-77-9 (S)-N-(tert-Butoxycarbonyl)-1-phenyl-3-butenylamine 
• 1357361-01-3 6-(bromomethyl)-4-phenyl-1,3-oxazinan-2-one 
• 326477-54-7 6-phenyl-5,6-dihydro-2,4(1H,3H)-pyridinedione 
• 1388191-41-0 C₁₉H₂₀N₂ 

Relevant articles and documents

Synthesis and catalytic application of chiral 1,1′-bi-2-naphthol-and biphenanthrol-based pincer complexes: Selective allylation of sulfonimines with allyl stannane and allyl trifluoroborate

(Chemical Equation Presented) New easily accessible 1,1′-bi-2- naphthol- (BINOL-) and biphenanthrol-based chiral pincer complex catalysts were prepared for selective (up to 85% enantiomeric excess) allylation of sulfonimines. The chiral pincer complexes w

Homoallylic amines as efficient chiral inducing frameworks in the conjugate addition of amides to α,β-unsaturated esters. An entry to enantio-enriched diversely substituted amines

The diastereoselective conjugate addition of secondary homoallylamines, obtained in the enantioenriched form via allylmetallation of imines, to α,β-unsaturated esters is reported. This method allows access to valuable building blocks as well as heterocyclic skeletons, providing tertiary amines bearing two chains integrating a stereogenic center adjacent to the nitrogen atom.

Enantioselective Strecker and Allylation Reactions with Aldimines Catalyzed by Chiral Oxazaborolidinium Ions

Chiral oxazaborolidinium ion (COBI)-catalyzed enantioselective nucleophilic addition reactions of aldimines using tributyltin cyanide and allyltributylstannane have been developed. Various α-aminonitriles and homoallylic amines were synthesized in high yi

Asymmetric Petasis Borono-Mannich Allylation Reactions Catalyzed by Chiral Biphenols

Chiral biphenols catalyze the asymmetric Petasis borono-Mannich allylation of aldehydes and amines through the use of a bench-stable allyldioxaborolane. The reaction proceeds via a two-step, one-pot process and requires 2–8 mole % of 3,3′-Ph2-BINOL as the optimal catalyst. Under microwave heating the reaction affords chiral homoallylic amines in excellent yields (up to 99 %) and high enantioselectivies (er up to 99:1). The catalytic reaction is a true multicomponent condensation reaction whereas both the aldehyde and the amine can possess a wide range of structural and electronic properties. Use of crotyldioxaborolane in the reaction results in stereodivergent products with anti- and syn-diastereomers both in good diastereoselectivities and enantioselectivities from the corresponding E- and Z-borolane stereoisomers.

Catalytic Manufacturing Method for Imine Having No Substituent Group on the Nitrogen, and Use for the Imine Produced

The present invention relates to a method for manufacturing an imine having no substituent group on the nitrogen by using, as a catalyst, a metal complex on an organic azide compound, and more specifically relates to a method in which a metal-complex catalyst is used to produce, from an organic azide having an alpha-hydrogen, an imine having no substituent group on the nitrogen via a continuous nitrogen removal and 1,2-hydrogen transfer reaction. The imine having no substituent group on the nitrogen manufactured by means of the method of the present invention can synthesise diverse coupling products comprising amine compounds by means of reactions with diverse nucleophiles.

Copper-catalyzed asymmetric allylation of chiral N-tert-butanesulfinyl imines: Dual stereocontrol with nearly perfect diastereoselectivity

Copper-catalyzed asymmetric allylation of chiral N-tert-butanesulfinyl imines has been described. Dual stereocontrol, through the combination of a chiral auxiliary and a chiral copper complex, has played an important role in achieving the nearly perfect d

Enantioselective synthesis of angularly substituted 1-azabicylic rings: Coupled dynamic kinetic epimerization and chirality transfer

A new strategy for enantioselective synthesis of azacyclic molecules in which dynamic kinetic equilibration of diastereomeric iminium ions precedes a stereochemistry-determining sigmatropic rearrangement is reported. The method is illustrated by the synthesis, in high enantiomeric purity (generally 95-99% ee), of a variety of 1-azabicyclic molecules containing angular allyl or 3-substituted 2-propenyl side chains adjacent to nitrogen and up to three stereogenic centers. In these products, the size of the carbocyclic ring is varied widely (5-12 membered); however, useful yields are obtained in forming 1-azabicyclic products containing only fused pyrrolidine and piperidine rings. Chirality transfer from substituents at carbons 1 and 2 of the 3-butenylamine fragment of the starting material is investigated, with methyl and phenyl substituents at the allylic position shown to provide exquisite stereocontrol (generally 98-99% chirality transfer). An attractive feature of the method is the ability to carry out the key transformation in the absence of solvent. Illustrated also is the high yielding conversion of four such products to a new family of bicyclic β-amino acids of high enantiomeric purity.

Enantio- and diastereoselective synthesis of β-substituted-δ- aminoboronic esters from nitriles

The first stereocontrolled synthesis of the title δ-aminoboronic esters - proceeding from commercially available nitriles - via a reduction, Brown's 'allyl' boration reaction, a Boc-protection, a hydroboration, an oxidative elimination of α-pinene, and an esterification reaction, has been reported in excellent enantio- and diastereoselectivities.

Design, synthesis, and applications of chiral N-2-phenyl-2-propyl sulfinyl imines for group-assisted purification (GAP) asymmetric synthesis

A new chiral (Rs)-2-phenyl-2-propyl sulfinamide has been designed and synthesized; its derived aldimines and ketimines have been applied for asymmetric addition reaction with allylmagnesium bromide. The reaction was conveniently performed at room temperature to give a series of homoallylic amines in high yields (up to quant) and diastereoselectivity (up to >99% de). The pure products were obtained by relying on group-assisted purification (GAP) chemistry to avoid traditional purification methods of column chromatography or recrystallization. The conversion of disulfide to (Rs)-thiosulfinate which contains a newly generated polar group was also confirmed to be of the GAP chemistry in which washing crude product can generate pure enantiomer. The absolute stereochemistry has been determined by X-ray analysis.

Characterization and utility of N-unsubstituted imines synthesized from alkyl azides by ruthenium catalysis

Shine a light: A fluorescent light-induced synthetic method for the title compounds has been developed and the chemoselective nature of the reaction is highlighted by the observation of the cis/trans isomers of various N-unsubstituted imines. The synthetic utility of this method is demonstrated by the one-pot imine formation/asymmetric allylation sequence of benzyl azide catalyzed by 1. (Ipc=isopinocampheyl). Copyright