22374-89-6

Basic information

• Product Name: 2-Amino-4-phenylbutane
• Synonyms: .alpha.-Methyl-.gamma.-phenyl-n-propylamine;.alpha.-methyl-.gamma.-phenyl-Propylamine;1-methyl-3-phenyl-propylamin;1-Phenyl-3-amino-butan;1-Phenyl-3-aminobutane;3-Phenyl-1-methylpropylamine;4-Phenyl-2-aminobutane;alpha-methyl-benzenepropanamin
• CAS NO: 22374-89-6
• Molecular Formula: C₁₀H₁₅N
• Molecular Weight: 149.23
• EINECS: 244-942-2
• Product Categories: AmphetamineStable Isotopes;Controlled Drug Standards;A;Alphabetic;AM to AQDrugs of Abuse;Chemical Structure;Amines;Building Blocks;C10;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 22374-89-6.mol
• Article Data: 52

Chemical Properties

• Melting Point: -50°C
• Boiling Point: 228-232 °C(lit.)
• Flash Point: 208 °F
• Appearance: colorless liquid
• Density: 0.922 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.107mmHg at 25°C
• Refractive Index: n20/D 1.514(lit.)
• Storage Temp.: −20°C
• PKA: pKa 10.0 (Uncertain)
• Water Solubility: 8.5 g/L (20 ºC)
• Sensitive: Air Sensitive
• BRN: 2413110
• CAS DataBase Reference: 2-Amino-4-phenylbutane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-4-phenylbutane(22374-89-6)
• EPA Substance Registry System: 2-Amino-4-phenylbutane(22374-89-6)

Safety Data

• Hazard Codes: C,Xi,T,F
• Statements: 34-22-39/23/24/25-23/24/25-11
• Safety Statements: 26-36/37/39-45-28A-36/37
• RIDADR: UN 2735 8/PG 3
• WGK Germany: 2
• RTECS: UI3920000
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 22374-89-6(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless liquid

Uses

2-Amino-4-phenylbutane is used in the synthesis of N-substituted derivatives of (1-methyl-3- phenylpropyl)amine.

Biological Functions

Amphetamine is an indirectly acting adrenomimetic amine that depends for its action on the release of norepinephrine from noradrenergic nerves. Its pharmacological effects are similar to those of ephedrine; however, its CNS stimulant activity is somewhat greater. Both systolic and diastolic blood pressures are increased by oral dosing with amphetamine. The heart rate is frequently slowed reflexively. Cardiac output may remain unchanged in the low- and moderate-dose range. The therapeutic uses of amphetamine are based on its ability to stimulate the CNS. The D-isomer (dextroamphetamine) is three to four times as potent as the L-isomer in producing CNS effects. It has been used in the treatment of obesity because of its anorexic effect, although tolerance to this effect develops rapidly. It prevents or overcomes fatigue and has been used as a CNS stimulant. Amphetamine is no longer recommended for these uses because of its potential for abuse. Amphetamine is useful in certain cases of narcolepsy or minimal brain dysfunction.

Flammability and Explosibility

Notclassified

Safety Profile

A poison by intraperitoneal and parenteral route. Moderately toxic by ingestion.When heated to decomposition it emits toxic vapors of NOx.

InChI:InChI=1/C10H15N/c1-9(11)7-8-10-5-3-2-4-6-10/h2-6,9H,7-8,11H2,1H3/p+1/t9-/m0/s1

Upstream product

• 2887-98-1 benzalacetone oxime 
• 2550-26-7 4-Phenyl-2-butanone 
• 540-69-2 ammonium formate 
• 1896-62-4 (E)-benzalacetone 
• 53309-95-8 (+/-)-2-amino-4-phenylbut-3-ene 
• 87927-86-4 3-methyl-4-phenyl-methyl-5(2H)-isoxazolone 
• 61210-87-5 [((E)-4-phenylbut-3-en-2-ylidene)amino]hydroxide 
• 68164-04-5 N-benzyl-1-methyl-3-phenylpropylamine 
• 155791-29-0 1-(1-azidoethyl)benzotriazole 
• 103-79-7 1-phenyl-acetone 
• 7664-41-7 ammonia 
• 64-17-5 ethanol 
• 22921-89-7 1-(4-phenylbut-3-en-2-ylidene)-2-phenylhydrazone 
• 64-19-7 acetic acid 

Downstream Products

• 104828-64-0 N,N-dimethyl-4-phenyl-2-butanamine 
• 10528-67-3 4-cyclohexyl-2-butanol 
• 138963-86-7 N-(1-phenylbutan-3-yl)benzamide 
• 433236-68-1 (1-methyl-3-phenyl-propyl)-oxalamic acid ethyl ester 
• 70959-62-5 2-Chloro-5-[1-hydroxy-2-(1-methyl-3-phenyl-propylamino)-ethyl]-benzenesulfonamide 
• 70958-61-1 5-[1-Hydroxy-2-(1-methyl-3-phenyl-propylamino)-ethyl]-2-methylsulfanyl-benzenesulfonamide 
• 70958-62-2 5-[1-Hydroxy-2-(1-methyl-3-phenyl-propylamino)-ethyl]-2-methanesulfonyl-benzenesulfonamide 
• 70958-60-0 3-[1-hydroxy-2-(1-methyl-3-phenylpropylamino)ethyl]benzenesulfonamide 
• 52507-02-5 ((E)-2-{4-[2-Hydroxy-3-(1-methyl-3-phenyl-propylamino)-propoxy]-phenyl}-vinyl)-carbamic acid methyl ester 

Relevant articles and documents

Air Stable Iridium Catalysts for Direct Reductive Amination of Ketones

Half-sandwich iridium complexes bearing bidentate urea-phosphorus ligands were found to catalyze the direct reductive amination of aromatic and aliphatic ketones under mild conditions at 0.5 mol % loading with high selectivity towards primary amines. One of the complexes was found to be active in both the Leuckart–Wallach (NH4CO2H) type reaction as well as in the hydrogenative (H2/NH4AcO) reductive amination. The protocol with ammonium formate does not require an inert atmosphere, dry solvents, as well as additives and in contrast to previous reports takes place in hexafluoroisopropanol (HFIP) instead of methanol. Applying NH4CO2D or D2 resulted in a high degree of deuterium incorporation into the primary amine α-position.

Synthesis of α-Deuterated Primary Amines via Reductive Deuteration of Oximes Using D2O as a Deuterium Source

Selective introduction of the deuterium atom into the α-position of amines is important for the development of all types of novel deuterated drugs and agrochemicals due to the pervasive presence of amines. In this study, we report the first general single-electron-transfer reductive deuteration of both ketoximes and aldoximes using SmI2 as an electron donor and D2O as a deuterium source for the synthesis of α-deuterated primary amines with excellent levels of deuterium incorporations (>95% [D]). This protocol exhibits excellent chemoselectivity and tolerates a variety of functional groups. The potential application of this new method was showcased in the synthesis of deuterated drugs, such as rimantadine-d4, the tebufenpyrad analogue, derivatives of nabumetone and pregnenolone, and a series of building blocks for the rapid and general assembly of deuterated drugs and pesticides.

Method for preparing primary amine by catalyzing reductive amination of aldehyde ketone compounds

The invention discloses a method for preparing primary amine by catalyzing reductive amination of aldehyde ketone compounds. The method comprises the following steps: 1) mixing nickel nitrate hexahydrate, citric acid and an organic solvent, carrying out heating and stirring until a colloidal material is obtained, drying the colloidal material, roasting the colloidal material in a protective atmosphere, pickling, washing and drying a roasted product, and performing a partial oxidation reaction on a dried product in an oxygen-nitrogen mixed atmosphere to obtain a catalyst for a reductive amination reaction; and 2) mixing aldehyde or ketone compounds, a methanol solution of ammonia and the reductive amination reaction catalyst, introducing hydrogen, and carrying out a reductive amination reaction. The method has the advantages of high primary amine yield, high selectivity, wide aldehyde ketone substrate range, short reaction time, mild reaction conditions, low cost, greenness, economicalperformance and the like; the used reductive amination reaction catalyst can be recycled more than 10 times, and the catalytic activity of the catalyst is not obviously changed in gram-level reactions; and the method is suitable for large-scale application.