13103-80-5

Basic information

• Product Name: 3'-Hydroxypropiophenone
• Synonyms: 3-HYDROXY PROPIOPHENONE;3'-HYDROXYPROPIOPHENONE;1-(3-hydroxyphenyl)propan-1-one;1-Propanone,1-(3-hydroxyphenyl)-
• CAS NO: 13103-80-5
• Molecular Formula: C₉H₁₀O₂
• Molecular Weight: 150.17
• EINECS: 236-027-1
• Mol File: 13103-80-5.mol
• Article Data: 10

Chemical Properties

• Melting Point: 82 °C
• Boiling Point: 288.9 °C at 760 mmHg
• Flash Point: 121.4 °C
• Appearance: /
• Density: 1.104 g/cm³
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 9.09±0.10(Predicted)
• CAS DataBase Reference: 3'-Hydroxypropiophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-Hydroxypropiophenone(13103-80-5)
• EPA Substance Registry System: 3'-Hydroxypropiophenone(13103-80-5)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 13103-80-5(Hazardous Substances Data)

Usage

Uses

1-?(3-?Hydroxyphenyl)?-?1-?propanone is a reactant used to synthesize tricyclic fused pyridines, a family of alkaloids with antimalarial activity.

Preparation

Preparation by diazotization of m-aminopropiophenone, followed by decomposition of the diazonium salt obtained, (71%) Also obtained by saponification of 3-acetoxypropiophenone (b.p.2 127–128°) with refluxing 10% sodium hydroxide for 2–3 h (83%) Also obtained by reductive deamination of 2-amino-5-hydroxypropiophenone (diazotization, followed by decomposition of the diazonium salt formed with copper powder in ethanol) Also obtained by reaction of ethylmagnesium bromide with 3-hydroxy-N, N-diethylbenzamide in refluxing n-butyl ether for 4 h (75%) Also obtained by treatment of 3-methoxypropiophenone (b.p.0.05 70–76°) with pyridinium chloride at 210° for 30 min (85%) Also obtained by treatment of 1-hydroxy-1-(3-hydroxyphenyl)propane (m.p. 105–107°) with DDQ in dioxane for 72 h (97%).

Synthetic route

α-ethyl-3-hydroxybenzyl alcohol (55789-02-1) → 1-(3-hydroxyphenyl)propan-1-one (13103-80-5)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane for 72h;	97%

1-(3-methoxyphenyl)propan-1-one (37951-49-8) → 1-(3-hydroxyphenyl)propan-1-one (13103-80-5)

Conditions	Yield
Stage #1: 1-(3-methoxyphenyl)propan-1-one With aluminum (III) chloride In toluene at 20℃; for 5h; Heating / reflux; Stage #2: With hydrogenchloride; water In toluene	94%
With aluminum (III) chloride In toluene at 20℃; for 5h; Heating / reflux;	94%
With pyridine; hydrogenchloride at 210℃; for 0.5h;	85%
With hydrogen bromide; acetic acid at 100℃; for 6h;	1.73 g

3-Hydroxyacetophenone (121-71-1) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 1-(3-hydroxyphenyl)propan-1-one (13103-80-5)

Conditions	Yield
With ammonium peroxydisulfate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer In water at 110℃; for 3h; Inert atmosphere; Sealed tube;	63%

1-(3-amino-phenyl)-propan-1-one (1197-05-3) → 1-(3-hydroxyphenyl)propan-1-one (13103-80-5)

Conditions	Yield
With sulfuric acid und Eintragen des Reaktionsgemisches in wss. NaNO2-Loesung in der Waerme;
With hydrogenchloride; sodium nitrite in der Kaelte und Erwaermen des Reaktionsgemisches;
With sulfuric acid; sodium nitrite und Eintragen des Reaktionsgemisches in mit Toluol ueberschichtete, auf 60grad erwaermte wss. Schwefelsaeure;

N,N-diethyl 3-hydroxybenzamide (15789-04-5) + ethylmagnesium bromide (925-90-6) → 1-(3-hydroxyphenyl)propan-1-one (13103-80-5)

Conditions	Yield
With diethyl ether; dibutyl ether Erhitzen des vom Diaethylaether befreiten Reaktionsgemisches auf Siedetemperatur und anschliessende Hydrolyse;

1-(3-acetoxy-phenyl)-propan-1-one → 1-(3-hydroxyphenyl)propan-1-one (13103-80-5)

Conditions	Yield
With sodium hydroxide

β-dimethylamino-m-hydroxypropiophenone hydrochloride (5453-62-3) → 1-(3-hydroxyphenyl)propan-1-one (13103-80-5)

Conditions	Yield
With ethanol; nickel at 80℃; under 58840.6 Torr; Hydrogenation;

(3-methoxyphenyl)magnesium bromide (36282-40-3) → 1-(3-hydroxyphenyl)propan-1-one (13103-80-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 97 percent / tetrahydrofuran; diethyl ether / -70 °C 2: 85 percent / pyridine, concd. HCl / 0.5 h / 210 °C View Scheme

meta-hydroxybenzaldehyde (100-83-4) → 1-(3-hydroxyphenyl)propan-1-one (13103-80-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 58 percent / diethyl ether / 1 h 2: 97 percent / DDQ / dioxane / 72 h View Scheme

3-(chlorocarbonyl)phenyl acetate (16446-73-4) → 1-(3-hydroxyphenyl)propan-1-one (13103-80-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: anschliessendes Behandeln mit wss. Natronlauge 2: dibutyl ether; diethyl ether / Erhitzen des vom Diaethylaether befreiten Reaktionsgemisches auf Siedetemperatur und anschliessende Hydrolyse View Scheme

1,4-dioxane (123-91-1) + 2,3-dicyano-5,6-dichloro-p-benzoquinone (84-58-2) → 1-(3-hydroxyphenyl)propan-1-one (13103-80-5)

3-Methoxybenzoic acid (586-38-9) → 1-(3-hydroxyphenyl)propan-1-one (13103-80-5)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: oxalyl dichloride / N,N-dimethyl-formamide; tetrahydrofuran / 2 h / 20 °C 1.2: 4 h / 20 °C 2.1: ethylmagnesium bromide / tetrahydrofuran / 2 h / 0 - 20 °C 3.1: acetic acid; hydrogen bromide / 6 h / 100 °C View Scheme

N,3‐dimethoxy‐N‐methylbenzamide (152121-82-9) → 1-(3-hydroxyphenyl)propan-1-one (13103-80-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethylmagnesium bromide / tetrahydrofuran / 2 h / 0 - 20 °C 2: acetic acid; hydrogen bromide / 6 h / 100 °C View Scheme

m-anisoyl chloride (1711-05-3) → 1-(3-hydroxyphenyl)propan-1-one (13103-80-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine / tetrahydrofuran; dichloromethane / 15 h / 5 - 15 °C 2: tetrahydrofuran / 2.5 h / 5 - 20 °C 3: aluminum (III) chloride / toluene / 5 h / 20 °C / Heating / reflux View Scheme

1-(3-hydroxyphenyl)propan-1-one (13103-80-5) + methyl iodide (74-88-4) → 1-(3-methoxyphenyl)propan-1-one (37951-49-8)

Conditions	Yield
Stage #1: 1-(3-hydroxyphenyl)propan-1-one With potassium hydroxide In acetone at 40℃; for 0.5h; Stage #2: methyl iodide With tetrabutylammomium bromide; potassium carbonate In acetone at 40 - 45℃; for 12h;	99%

1-(3-hydroxyphenyl)propan-1-one (13103-80-5) + ethyl bromoacetate (105-36-2) → ethyl ((3-propanoylphenyl)oxy)acetate

Conditions	Yield
With potassium carbonate In acetone at 20℃; for 5h; Heating / reflux;	98%

1-(3-hydroxyphenyl)propan-1-one (13103-80-5) + 2-(2-Chloroethoxy)ethanol (628-89-7) → 1-(3-((2-((2-hydroxyethyl)oxy)ethyl)oxy)phenyl)-1-propanone

Conditions	Yield
With potassium carbonate In acetone for 60h; Heating / reflux;	95%

4-bromoethylbutanoate (2969-81-5) + 1-(3-hydroxyphenyl)propan-1-one (13103-80-5) → ethyl 4-((3-propanoylphenyl)oxy)butanoate

Conditions	Yield
With potassium carbonate In acetone for 15h; Heating / reflux;	92%

1-(3-hydroxyphenyl)propan-1-one (13103-80-5) → α-ethyl-3-hydroxybenzyl alcohol (55789-02-1)

Conditions	Yield
With methanol; bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; 6,6′‐dihydroxyl‐2,2′‐bipyridine; potassium hydroxide at 60℃; for 24h; Inert atmosphere;	88%

Nicotinic acid hydrazide (553-53-7) + 1-(3-hydroxyphenyl)propan-1-one (13103-80-5) → 3‑pyridinecarboxylic acid [1‑(3‑hydroxyphenyl)propylidene]hydrazide

Conditions	Yield
With aluminium(III) chloride hexahydrate In water at 60℃; for 3h; Green chemistry;	86%

1-(3-hydroxyphenyl)propan-1-one (13103-80-5) + 2-bromomethylnaphthyl bromide (939-26-4) → 1-<3-(naphth-2-ylmethoxy)phenyl>propan-1-one (129425-69-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 18h; Ambient temperature;	85%

pent-3-yn-1-ol (10229-10-4) + 1-(3-hydroxyphenyl)propan-1-one (13103-80-5) → 1-[3-(pent-3-yn-1-yloxy)phenyl]propan-1-one

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; Mitsunobu Displacement; Inert atmosphere; Sealed tube;	80%

trifluoromethylsulfonic anhydride (358-23-6) + 1-(3-hydroxyphenyl)propan-1-one (13103-80-5) → 3-propionylphenyl trifluoromethanesulfonate

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 3.5h;	72%

diethyl (1-cyanoethyl)phosphonate (29668-61-9) + 1-(3-hydroxyphenyl)propan-1-one (13103-80-5) → (E)-3-(3-hydroxyphenyl)-2-methylpent-2-enenitrile + (Z)-3-(3-hydroxyphenyl)-2-methylpent-2-enenitrile

Conditions	Yield
Stage #1: diethyl (1-cyanoethyl)phosphonate With sodium hydride In tetrahydrofuran at 5℃; for 0.25h; Stage #2: 1-(3-hydroxyphenyl)propan-1-one In tetrahydrofuran at 20℃; for 4h; Concentration; Reagent/catalyst; Time; Temperature; Cooling with ice;	A 42% B 22%

4-(4,4-dimethyl-3-(3-hydroxypropyl)-5-oxo-2-thioxo-1-imidazolidinyl) 2-(trifluoromethyl) benzonitrile (155255-59-7) + 1-(3-hydroxyphenyl)propan-1-one (13103-80-5) → 4-{4,4-dimethyl-5-oxo-3-[3-(3-propionyl-phenoxy)-propyl]-2-thioxo-imidazolidin-1-yl}-2-trifluoromethyl-benzonitrile

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 4.16667h;	30%

1-(3-hydroxyphenyl)propan-1-one (13103-80-5) + (2-chloroethyl)dimethylamine hydrochloride (4584-46-7) → 1-(3-{[2-(dimethylamino)ethyl]oxy}phenyl)-1-propanone

Conditions	Yield
With potassium carbonate In water; acetone for 24h; Heating / reflux;	25%

1-(3-hydroxyphenyl)propan-1-one (13103-80-5) → 3-n-propylphenol (621-27-2)

Conditions	Yield
With molybdenum (IV) sulfide at 275℃; under 73550.8 Torr; Hydrogenation;
With potassium hydroxide; hydrazine In diethylene glycol

1-(3-hydroxyphenyl)propan-1-one (13103-80-5) + 2-(diethylamino)ethyl chloride (100-35-6) → 3'-(2-Diaethylamino-aethoxy)-propiophenon (3705-04-2)

Conditions	Yield
(i) Na, (ii) /BRN= 605300/; Multistep reaction;

1-(3-hydroxyphenyl)propan-1-one (13103-80-5) → 2,4,6-Tribrom-3-propionyl-phenol (23689-31-8)

Conditions	Yield
With bromine

ethanol (64-17-5) + 1-(3-hydroxyphenyl)propan-1-one (13103-80-5) + palladium/charcoal → 3-n-propylphenol (621-27-2)

Conditions	Yield
Hydrogenation;

1-(3-hydroxyphenyl)propan-1-one (13103-80-5) + ammonia (7664-41-7) + aqueous KOH + Raney nickel → 1-<3-hydroxy-phenyl>-propanol-(1)

Conditions	Yield
Hydrogenation;

diethyl ether (60-29-7) + 1-(3-hydroxyphenyl)propan-1-one (13103-80-5) + amalgamated aluminium → 3.4-bis-<3-acetoxy-phenyl>-hexanediol-(3.4) of mp: 158-159 degree

Conditions	Yield
und Erhitzen des Reaktionsprodukts mit Acetanhydrid und wenig Pyridin;

1-(3-hydroxyphenyl)propan-1-one (13103-80-5) → 1-(3-hydroxy-4-nitro-phenyl)-propan-1-one + 1-(5-hydroxy-2-nitrophenyl)propan-1-one (453518-19-9)

Conditions	Yield
With nitric acid; acetic acid at 70℃;

1-(3-hydroxyphenyl)propan-1-one (13103-80-5) → 1-[2-amino-5-(2-piperidin-1-yl-ethoxy)-phenyl]-propan-1-one (708254-67-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: HNO3; AcOH / 70 °C 2: K2CO3 / dimethylformamide / 3 h / 80 °C 3: Fe; aq. HCl / ethanol; acetic acid / 0.25 h / Heating View Scheme

1-(3-hydroxyphenyl)propan-1-one (13103-80-5) → 1-[2-nitro-5-(2-piperidin-1-yl-ethoxy)-phenyl]-propan-1-one (708254-65-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: HNO3; AcOH / 70 °C 2: K2CO3 / dimethylformamide / 3 h / 80 °C View Scheme

Upstream product

• 1197-05-3 1-(3-amino-phenyl)-propan-1-one 
• 5453-62-3 β-dimethylamino-m-hydroxypropiophenone hydrochloride 
• 37951-49-8 1-(3-methoxyphenyl)propan-1-one 
• 121-71-1 3-Hydroxyacetophenone 
• 68-12-2 N,N-dimethyl-formamide 
• 1711-05-3 m-anisoyl chloride 
• 152121-82-9 N,3‐dimethoxy‐N‐methylbenzamide 
• 586-38-9 3-Methoxybenzoic acid 
• 123-91-1 1,4-dioxane 
• 84-58-2 2,3-dicyano-5,6-dichloro-p-benzoquinone 
• 16446-73-4 3-(chlorocarbonyl)phenyl acetate 
• 100-83-4 meta-hydroxybenzaldehyde 
• 36282-40-3 (3-methoxyphenyl)magnesium bromide 
• 55789-02-1 α-ethyl-3-hydroxybenzyl alcohol 

Downstream Products

• 129425-69-0 1-<3-(naphth-2-ylmethoxy)phenyl>propan-1-one 
• 621-27-2 3-n-propylphenol 
• 708254-67-5 1-[2-amino-5-(2-piperidin-1-yl-ethoxy)-phenyl]-propan-1-one 
• 708254-65-3 1-[2-nitro-5-(2-piperidin-1-yl-ethoxy)-phenyl]-propan-1-one 
• 134154-50-0 3-(tert-butyldimethylsilyloxy)phenyl ethyl ketone 
• 129424-07-3 3-<1-methoxy-1-(thiazol-2-yl)propyl>phenol 
• 1343471-61-3 rac-3-(dimethylamino)-1-(3-hydroxyphenyl)-2-methylpropan-1-one 
• 1369205-96-8 [2R]-toluene-4-sulfonic acid 3-(3-dimethylamino-2-methylpropionyl)phenyl ester 
• 1369205-95-7 [2S]-toluene-4-sulfonic acid 3-(3-dimethylamino-2-methylpropionyl)phenyl ester 
• 1369205-80-0 toluene-4-sulfonic acid 3-propionylphenyl ester 
• 515114-52-0 (±)-3-(1-(dimethylamino)-2-methylpentan-3-yl)phenol 
• 175591-09-0 3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenol hydrochloride 
• 175591-09-0 tapentadol hydrochloride 
• 175591-23-8 tapentadol 

Relevant articles and documents

TETRAZOLINONE COMPOUND AND USE THEREOF

A tetrazolinone compound represented by formula (1): wherein R1 and R2 each represents a hydrogen atom, a halogen atom, or a C1-C3 alkyl group; R3 represents a C1-C3 alkyl group optionally having one or more halogen atoms; R4, R5, and R6 each represents a hydrogen atom or a halogen atom; R7 represents a C1-C3 alkyl group; Q represents a divalent group selected from Group P4; and A represents a C7-C18 aralkyloxy group optionally having one or more atoms or groups selected from Group P3, has excellent control activity against pests.

CHEMICAL COMPOUNDS

The present invention discloses novel compounds with a variety of therapeutic uses. More particularly, the invention discloses novel symmetrical triphenyl compounds that are particularly useful for selective estrogen receptor modulation.

5-LIPOXYGENASE INHIBITORY THIAZOLES

The invention concerns a thiazole of the formula I, wherein Ar1 is optionally substituted aryl of up to 10 carbon atoms; A is a direct link to X, or is (1-6C)alkylene, (3-6C)alkenylene, (3-6C)alkynylene or cyclo(3-6C)alkylene; X is oxy, thio, sulphinyl, sulphonyl or imino; Ar2 is optionally substituted phenylene, or a 6-membered heterocyclene moiety containing up to three nitrogen atoms; R1 is hydrogen, (1-6C)alkyl, (2-6C)alkenyl, (2-6C)alkynyl or substituted (1-4C)alkyl; R2 is hydrogen, (1-6C)alkyl, (3-6C)alkenyl, (3-6C)alkynyl, substituted (1-4C)alkyl or (2-6C)alkanoyl; Q is optionally substituted thiazolyl; or a pharmaceutically-acceptable salt thereof. The invention also concerns processes for the manufacture of a thiazole of the formula I, or a pharmaceutically-acceptable salt thereof, and pharmaceutical compositions containing said thiazole