70-69-9

Basic information

• Product Name: 4'-AMINOPROPIOPHENONE
• Synonyms: P-AMINOPROPIOPHENONE;P-AMINOPHENYL ETHYL KETONE;NSC 3187;NSC 404994;1-(4-aminophenyl)-1-propanon;4’-amino-propiophenon;Para-aminopropiophenone;paraminopropiophenone
• CAS NO: 70-69-9
• Molecular Formula: C₉H₁₁NO
• Molecular Weight: 149.19
• EINECS: 200-742-7
• Product Categories: Aromatic Propiophenones (substituted)
• Mol File: 70-69-9.mol

Chemical Properties

• Melting Point: 135-140 °C
• Boiling Point: 270.27°C (rough estimate)
• Flash Point: 138.7oC
• Appearance: /
• Density: 1.067±0.06 g/cm3 (20 ºC 760 Torr)
• Refractive Index: 1.5279 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 2.86±0.10(Predicted)
• Water Solubility: 352.1mg/L(37.5 oC)
• CAS DataBase Reference: 4'-AMINOPROPIOPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-AMINOPROPIOPHENONE(70-69-9)
• EPA Substance Registry System: 4'-AMINOPROPIOPHENONE(70-69-9)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45-28A
• RIDADR: 2811
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 70-69-9(Hazardous Substances Data)

Usage

Uses

Used in the Chemical Industry:
4'-Aminopropiophenone is used as an intermediate in the synthesis of various pharmaceuticals and chemical compounds. It plays a crucial role in the production of drugs, dyes, and other organic compounds.
Used in the Production of High-Strength Carbon Nanotube Films:
4'-Aminopropiophenone is used in a method for preparing high-strength carbon nanotube films by thiol-ene click reaction. This method allows for the creation of strong and durable carbon nanotube films with a wide range of applications, including electronics, aerospace, and automotive industries.

Preparation

The preparation of 4'-aminopropiophenone is as follows:A reaction tube was charged with the 2-aryloxypropanamide (1.0 mmol), potassium hydroxide (56 mg, 1.0 mmol) and DMSO (4 mL). The mixture was heated at 140 C for 3-8 h. The reaction was monitored by TLC. After the reaction period, the reaction mixture was cooled, diluted with saturated brine and extracted with dichloromethane three times. The combined organic layers were washed with three portions of saturated brine and then dried over MgSO4 and filtered. Solvent was removed under reduced pressure. The product was purified through flash column chromatography on 300-400 mesh silica gel with petroleum ether/ethyl acetate as eluent.

Reactivity Profile

4'-AMINOPROPIOPHENONE is simultaneously a ketone and an amine. Neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Safety Profile

Poison by ingestion and intraperitoneal routes. Ingestion of large doses can cause cyanosis. A flammable liquid. When heated to decomposition it emits toxic fumes of NOx,.

Purification Methods

Crystallise it from water or aqueous EtOH. The hydrochloride has m 188-189o (aqueous EtOH/HCl drops), and the semicarbazone has m 139-140o (from EtOH/H2O). [Derrick & Bornemann J Am chem. Soc 35 1283 1913, Beilstein 14 H 59, 14 I 375, 14 III 146, 14 IV 139.]

Upstream product

• 6285-05-8 4'-chloropropiophenone 
• 16960-49-9 N-(4-propionylphenyl)acetamide 
• 620-71-3 N-(phenyl)-2-methylacetamide 
• 3758-70-1 1-(4-nitrophenyl)propan-1-one 
• 79-03-8 propionyl chloride 
• 103-84-4 Acetanilid 
• 223562-47-8 4-(prop-1-yn-1-yl)aniline 
• 7446-70-0 aluminium trichloride 
• 7647-01-0 hydrogenchloride 
• 80336-77-2 propionic acid-(4-propionyl-anilide) 
• 10342-83-3 4'-Bromopropiophenone 
• 106-40-1 4-bromo-aniline 
• 93-55-0 1-phenyl-propan-1-one 
• 1040063-44-2 2-(4-propionylphenoxy)propanamide 

Downstream Products

• 91767-01-0 N-(2-chloro-ethyl)-N'-(4-propionyl-phenyl)-urea 
• 100372-04-1 trans-crotonic acid-(4-propionyl-anilide) 
• 80336-77-2 propionic acid-(4-propionyl-anilide) 
• 16960-49-9 N-(4-propionylphenyl)acetamide 
• 99840-86-5 N-methyl-N'-(4-propionyl-phenyl)-thiourea 
• 101877-74-1 1-(4-phenacylamino-phenyl)-propan-1-one 
• 26672-58-2 1-(4-dimethylaminophenyl)propan-1-one 
• 13791-85-0 2-(4-Chloro-2-methyl-phenoxy)-N-(4-propionyl-phenyl)-propionamide 
• 23600-92-2 (Propionyl-4-phenyl)-(methoxy-4'-phenyl)-amin 
• 23600-91-1 (Propionyl-4-phenyl)-(methyl-4'-phenyl)-amin 
• 53033-82-2 4-(N-Methylamino)propiophenon 
• 31970-26-0 1-(4-iodophenyl)propan-1-one 
• 107274-01-1 3-pyrrolidino-butyric acid-(4-propionyl-anilide) 

Relevant articles and documents

Silver-catalyzed intermolecular amination of fluoroarenes

A novel highly selective Ag-catalyzed intermolecular amination of fluoroarenes has been developed. This transformation starts from readily available 4-carbonyl fluorobenzene and NaN3 or other nitrogen-source, via amination followed by C-F bond cleavage, thus affording the desired 4-carbonyl arylamine products under mild conditions. The reaction is accelerated using a small amount of water. This pathway is distinct from a previously reported radical amination reaction.

Selective Cross-Coupling of (Hetero)aryl Halides with Ammonia to Produce Primary Arylamines using Pd-NHC Complexes

Herein we report the first example of (hetero)arylation of ammonia using a monoligated palladium-NHC complex. The new, rationally designed, precatalyst (DiMeIHeptCl)Pd(allyl)Cl featuring highly branched alkyl chains has been shown to be effective in selective aminations across a range of challenging substrates, including nitrogen-containing heterocycles and those featuring base-sensitive functionality. The less bulky Pd-PEPPSI-IPentCl precatalyst performs well for ortho-substituted aryl halides, giving monoarylated products in high yield with good selectivity.

DMF Dimethyl Acetal as Carbon Source for α-Methylation of Ketones: A Hydrogenation-Hydrogenolysis Strategy of Enaminones

A novel heterogeneous catalytic hydrogenation-hydrogenolysis strategy has been developed for the α-methylation of ketones via enaminones using DMF dimethyl acetal as carbon source. This strategy provides a very convenient route to α-methylated ketones using a variety of ketones without any base or oxidant. (Chemical Equation Presented).

Metal-free C-N bond-forming reaction: Straightforward synthesis of anilines, through cleavage of aryl C-O bond and amide C-N bond

An efficient metal-free C-N bond forming reaction through cleavage of aryl C-O bond and amide C-N bond has been developed. This process represents a practical method for the facile construction of anilines with a broad substrate scope and wide functional group tolerance in moderate to excellent yields.

Palladium-catalysed transfer hydrogenation of aromatic nitro compounds - An unusual chain elongation

Aromatic nitro compounds are reduced via transfer hydrogenation in the presence of palladium on magnesium-lanthanum mixed oxide support in ethanol yielding the corresponding amines. With several acetophenone derivatives, the reduction was accompanied by c

Palladium-catalyzed coupling of ammonia with aryl chlorides, bromides, iodides, and sulfonates: A general method for the preparation of primary arylamines

We report that the complex generated from Pd[P(o-tol)3] 2 and the alkylbisphosphine CyPF-t-Bu is a highly active and selective catalyst for the coupling of ammonia with aryl chlorides, bromides, iodides, and sulfonates. The couplings of ammonia with this catalyst conducted with a solution of ammonia in dioxane form primary arylamines from a variety of aryl electrophiles in high yields. Catalyst loadings as low as 0.1 mol % were sufficient for reactions of many aryl chlorides and bromides. In the presence of this catalyst, aryl sulfonates also coupled with ammonia for the first time in high yields. A comparison of reactions in the presence of this catalyst versus those in the presence of existing copper and palladium systems revealed a complementary, if not broader, substrate scope. The utility of this method to generate amides, imides, and carbamates is illustrated by a one-pot synthesis of a small library of these carbonyl compounds from aryl bromides and chlorides, ammonia, and acid chlorides or anhydrides. Mechanistic studies show that reactions conducted with the combination of Pd[P(o-tol)3]2 and CyPF-t-Bu as catalyst occur with faster rates and higher yields than those conducted with CyPF-t-Bu and palladiun(II) as catalyst precursors because of the low concentration of active catalyst that is generated from the combination of palladium(II), ammonia, and base.

Zinc trimethylsilylamide as a mild ammonia equivalent and base for the amination of aryl halides and triflates

(Chemical Equation Presented) We report that Zn[N(SiMe3) 2]2 is a mild ammonia equivalent and base for the palladium-catalyzed amination of aryl halides and triflates. In contrast to LiN(SiMe3)2, the combination of Zn[N(SiMe 3)2]2 and LiCl coupled with aryl halides and triflates containing base-sensitive functionality in high yields. In addition, aryl bromides coupled with aryl and alkylamines with the combination of Zn[N(SiMe3)2]2 and LiCl as base. These aminations occurred without racemization of the enolizable stereocenter of an optically active ester.

A new practical one-pot conversion of phenols to anilines

(Chemical Equation Presented) A novel one-pot synthesis of anilines from phenols was developed. Using this methodology, anilines are produced in good yield (86%) by a reaction of phenols with 2-bromo-2-methylpropionamide and NaOH in DMA via Smiles rearrangement. Phenols, which are substituted electron-withdrawing groups, are more reactive for Smiles rearrangement. Thiophenols are also converted to anilines. The process is a convenient, safe, and inexpensive method for large-scale preparation of anilines.

Fries-type rearrangement of acylanilides in the presence of ytterbium triflate

Ytterbium triflate has been used to catalyse the Fries-type rearrangement of various acylanilides with moderate yields when lithium perchlorate was used as co-catalyst.

Alkyne metathesis with simple catalyst systems: High yield dimerization of propynylated aromatics; scope and limitations

High yield dimerization of propynylated benzenes and propynylnaphthalene by a mixture of Mo(CO)6 and 4-chlorophenol at 140 °C in 1,2-dichlorobenzene is reported to give the corresponding disubstituted alkynes. The scope and limitation of the reaction and the influence of substitution pattern and substitution type are discussed. Oxygen or nitrogen carrying substrates metathesize in moderate to good yields and ortho-alkyl substituted examples form the respective tolanes very efficiently.