770-39-8

Basic information

• Product Name: 4-Hydroxyphenylacetone
• Synonyms: 4-HYDROXYPHENYLACETONE;P-HYDROXYPHENYLACETONE;4-HYDROXYPHENYLACETONE +99%;4-Hydroxyphenylacetone, 98+%;1-(4-Hydroxyphenyl)-2-propanone;1-(4-Hydroxyphenyl)propan-2-one;1-(4-hydroxyphenyl)acetone;4-Hydroxyphenylacetone≥ 99% (GC)
• CAS NO: 770-39-8
• Molecular Formula: C₉H₁₀O₂
• Molecular Weight: 150.17
• Product Categories: Aromatic Ketones (substituted)
• Mol File: 770-39-8.mol

Chemical Properties

• Melting Point: 267°C
• Boiling Point: 177 °C / 11mmHg
• Flash Point: 114.5 °C
• Appearance: /
• Density: 1.12
• Vapor Pressure: 0.00327mmHg at 25°C
• Refractive Index: 1.543
• Storage Temp.: 2-8°C
• Solubility: soluble in Methanol
• PKA: 9.86±0.15(Predicted)
• CAS DataBase Reference: 4-Hydroxyphenylacetone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxyphenylacetone(770-39-8)
• EPA Substance Registry System: 4-Hydroxyphenylacetone(770-39-8)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36-37
• Hazardous Substances Data: 770-39-8(Hazardous Substances Data)

Usage

Uses

Used in Beauty and Skin Care Industry:
4-Hydroxyphenylacetone is used as an antibacterial peptide for beauty skin care cosmetics to better repair skin functions. Its antibacterial properties help in maintaining skin health and preventing infections, making it a valuable ingredient in the formulation of various skin care products.
Used in Chemical Synthesis:
4-Hydroxyphenylacetone serves as an important intermediate in the synthesis of various organic compounds, including pharmaceuticals, dyes, and other specialty chemicals. Its versatile chemical structure allows for further functionalization and modification, making it a useful building block in the chemical industry.
Used in Research and Development:
Due to its unique chemical properties, 4-Hydroxyphenylacetone is often utilized in research and development for the study of various chemical reactions and processes. It can be employed as a model compound to investigate the reactivity and behavior of similar molecules, contributing to the advancement of scientific knowledge in the field of organic chemistry.

InChI:InChI=1/C9H10O2/c1-7(10)6-8-2-4-9(11)5-3-8/h2-5,11H,6H2,1H3

Upstream product

• 122-84-9 4-methoxybenzyl methyl ketone 
• 365-26-4 oxilofrine 
• 621-87-4 3-phenoxy-2-propanone 
• 917-64-6 methyl magnesium iodide 
• 6305-04-0 p-hydroxyphenacyl chloride 
• 156-38-7 4-hydroxyphenylacetate 
• 917-54-4 methyllithium 
• 2491-38-5 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone 
• 75-16-1 methylmagnesium bromide 
• 5586-92-5 1-(4-benzyloxyphenyl)propan-2-one 
• 61126-42-9 1-(4-hydroxyphenyl)-2-nitropropene 
• 92915-65-6 4-(2-nitropropyl)phenol 

Downstream Products

• 714-23-8 4-(2-oxopropyl)phenyl acetate 
• 370-14-9 pholedrine 
• 60056-48-6 2-Benzyloxy-1-hydroxymethyl-6-[2-(4-hydroxy-phenyl)-1-methyl-ethylamino]-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol 
• 101712-18-9 1-<4-<(2-methoxyethoxy)methoxy>phenyl>-2-propanone 
• 86608-11-9 1-(4-(2-dimethylaminoethoxy)phenyl)propan-2-one 
• 16855-30-4 2-(4-Hydroxybenzyl)-2-methylaminopropionitrile 
• 184972-19-8 4-((S)-2-Hydroxy-propyl)-phenol 

Relevant articles and documents

Efficient demethylation of aromatic methyl ethers with HCl in water

A green, efficient and cheap demethylation reaction of aromatic methyl ethers with mineral acid (HCl or H2SO4) as a catalyst in high temperature pressurized water provided the corresponding aromatic alcohols (phenols, catechols, pyrogallols) in high yield. 4-Propylguaiacol was chosen as a model, given the various applications of the 4-propylcatechol reaction product. This demethylation reaction could be easily scaled and biorenewable 4-propylguaiacol from wood and clove oil could also be applied as a feedstock. Greenness of the developed methodversusstate-of-the-art demethylation reactions was assessed by performing a quantitative and qualitative Green Metrics analysis. Versatility of the method was shown on a variety of aromatic methyl ethers containing (biorenewable) substrates, yielding up to 99% of the corresponding aromatic alcohols, in most cases just requiring simple extraction as work-up.

Substituted 1,2,3,4-tetrahydroquinolin-6-yloxypropanes as β3-adrenergic receptor agonists: Design, synthesis, biological evaluation and pharmacophore modeling

In search of potent β3-adrenergic receptor agonists, a series of novel substituted 1,2,3,4-tetrahydroquinolin-6-yloxypropanes has been synthesized and evaluated for their β3-adrenergic receptor agonistic activity (ranging from -17.73% to 90.64% inhibition at 10 μM) using well established Human SK-N-MC neuroblastoma cells model. Four molecules viz. 11, 15, 22 and 23 showed β3-AR agonistic IC50 value of 0.55, 0.59, 1.18 and 1.76 μM, respectively. These four candidates have been identified as possible leads for further development of β3-adrenergic receptor agonists for obesity and Type-II diabetes pharmacotherapy. The free OH and NH functions are found to be essential for β3-adrenergic receptor agonistic activity. Among the synthesized β3-adrenergic receptor agonists having 1,2,3,4-tetrahydroquinoline scaffold, the N-benzyl group is found to be superior over N-arylsulfonyl group. A putative pharmacophore model has been modeled considering the above four active molecules which distinguishes well between the active and inactive molecules.

Fe-HCl: An efficient reagent for deprotection of oximes as well as selective oxidative hydrolysis of nitroalkenes and nitroalkanes to ketones

Fe-HCl mixture was found to selectively perform oxidative hydrolysis of the nitroalkenes 1a-j and nitroalkanes 2a-j to the ketones 3a-j. Also, the reagent was observed to deprotect the oximes 7a-j to carbonyl compounds 8a-j in excellent yields.

Mass spectrometric investigations on phenylacetic acid derivatives, IV: Loss of ortho-substituents from ionized phenyl-2-propanones upon electron impact

In the gas phase, the phenyl-2-propanone molecules 2a-4a lose upon electron impact chloro-, bromo-, and iodo-radicals specifically at the orthopOsition of the phenyl group giving rise to strong (M-Hal.)+-ions (70/12 eV; 1st and 2nd FFR) of identical structure as confirmed by their MIKE-CAD-spectra. The daughter ions at m/z 133 from o-chlorophenyl-2-propanone (2a) and 2,2-dimethyl-2,3-dihydro[b]furane (11) are structurally similar but not identical (similarity index 99.8). The collisionally activated (2nd FFR) (M-Br.)+-ions from o-bromophenyl-2-propanone (3a) and 1-bromo-1-phenyl-2-propanone (12) produce virtually congruent spectra. The most impOrtant subsequent fragmentation of the (M-Hal-)+-ions from 2a-4a is the loss of CO which incorporates the C-atom of the carbonyl group exclusively (13C labelling). Mechanistic aspects of the fragmentation sequences are discussed (Figs. 5 and 8).

Process for producing phenylacetones

A phenylacetone or its derivative having the general formula (I): STR1 wherein X, Y, and Z are independently a hydrogen atom, a hydroxyl group, a halogen atom, a nitro group, an amino group, a lower alkyl group having 1 to 6 carbon atoms, a lower alkoxy group having 1 to 6 carbon atoms, or a benzyloxy group and any two substituents of X, Y, and Z may form, together with the benzene ring, a heterocycling ring having 5 to 7 members including 1 or 2 oxygen atoms is produced at a high yield and a high selectivity by reacting a 3-phenylpropylene or its derivative having the general formula (II): STR2 wherein X, Y, and Z are as defined above, with an alkyl nitrite having the general formula (III): wherein R is an aliphatic, aromatic, or alicyclic saturated or unsaturated hydrocarbon group in the presence of (a) water, (b) an alcohol, (c) a palladium catalyst, and (d) an optional amine or copper compound, or by reacting the above-mentioned 3-phenylpropylene or its derivative with the above-mentioned alkyl nitrite in the presence of (a) an alcohol, (b) a palladium catalyst and (c) an optional amine or copper compound to form 1-phenyl-2,2-dialkoxypropane or it derivative having the general formula (IV): STR3 wherein X, Y, Z and R are as defined above, followed by hydrolyzing the reaction product.

Secondary amines

Compounds of formula (II): STR1 or salt thereof; wherein R1 is hydrogen or methyl, R2 is hydrogen or methyl, R3 is hydrogen, C1-12 straight or branched alkyl, C3-10 cycloalkyl, phenyl(C1-4)-alkyl or benzyl optionally substituted by C1-4 alkyl, C1-4 alkoxy or halogen; R4 is hydrogen, halogen, hydroxy, C1-4 alkyl or C1-4 alkoxy, R5 is hydrogen or fluorine, R6 is hydrogen or fluorine, R7 is halogen; and n is 1 or 2, have anti-obesity and/or anti-hyperglycaemic activity.

Reactions of 4-Substituted-2'-Halogenoacetophenones with Grignard Reagents

The initial reaction of 4-substituted 2'-halogenoacetophenones with an excess of methyl Grignard reagent is shown to be an attack at the 1'-carbonyl to form a halohydrin salt.The various reactions which then follow are substituent dependent.In the 4-hydroxy case the only product is 1-(4-hydroxyphenyl)-2-methylpropan-2-ol (13) which arises via a -aryl shift with simultaneous elimination of magnesium halide.When the substituent is 4-methoxy, a second pathway becomes important involving epoxide formation and a subsequent -hydride migration to the benzylic position, or attack of the Grignard reagent at the benzylic carbon of the epoxide.When the substituent is 4-bromo, the reaction proceeds exclusively via the epoxide and, following a -hydride shift, leads to the isomeric butanols (33) and (34).The reasons underlying such diversity of reactivity are discussed.

REACTION OF NITROOLEFINS WITH RANEY NICKEL AND SODIUM HYPOPHOSPHITE. A MILD METHOD FOR CONVERTING NITROOLEFINS INTO KETONES (OR ALDEHYDES).

Nitroolefins are converted into the corresponding saturated ketones or aldehydes in high yield by treatment with Raney nickel and sodium hypophosphite in aqueous ethanol at pH 5.