938-96-5

Basic information

• Product Name: 2-(4-HYDROXYPHENYL)PROPIONIC ACID
• Synonyms: TIMTEC-BB SBB003894;2-(4-HYDROXYPHENYL)PROPIONIC ACID;(4-HYDROXYPHENYL)-2-PROPIONIC ACID;4-HYDROXYHYDRATROPIC ACID;2-(4-Hydroxyphenyl)propanoic acid;4-Hydroxy-α-methylbenzeneacetic acid;(4-Hydroxyphenyl)-2-propionic acid,98%;(4-Hydroxyphenyl)(methyl)acetic acid
• CAS NO: 938-96-5
• Molecular Formula: C₉H₁₀O₃
• Molecular Weight: 166.17
• EINECS: 213-352-7
• Product Categories: Aromatic Propionic Acids
• Mol File: 938-96-5.mol
• Article Data: 12

Chemical Properties

• Melting Point: 131.6 °C
• Boiling Point: 254.38°C (rough estimate)
• Flash Point: 166.5 °C
• Appearance: White to slightly beige/Crystalline Powder or Chunks
• Density: 1.1708 (rough estimate)
• Vapor Pressure: 7.73E-05mmHg at 25°C
• Refractive Index: 1.5760 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: soluble in Methanol
• PKA: 4.55±0.10(Predicted)
• BRN: 2091472
• CAS DataBase Reference: 2-(4-HYDROXYPHENYL)PROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-HYDROXYPHENYL)PROPIONIC ACID(938-96-5)
• EPA Substance Registry System: 2-(4-HYDROXYPHENYL)PROPIONIC ACID(938-96-5)

Safety Data

• Hazard Codes: Xi,T
• Statements: 36/37/38-36-25
• Safety Statements: 37/39-26-45
• RIDADR: UN 2811 6.1 / PGIII
• Hazardous Substances Data: 938-96-5(Hazardous Substances Data)

Usage

Chemical Properties

white to slightly beige cryst. powder or chunks

InChI:InChI=1/C9H10O3/c1-6(9(11)12)7-2-4-8(10)5-3-7/h2-6,10H,1H3,(H,11,12)/p-1/t6-/m1/s1

Synthetic route

2-(4-methoxyphenyl)propanoic acid (942-54-1) → 2-(4-Hydroxy-phenyl)-propionic acid (938-96-5)

Conditions	Yield
With boron tribromide In dichloromethane at 20℃; for 2.5h;	90%
With hydrogen bromide for 15h; Heating;

2-(4-hydroxyphenyl)-1-phenylethan-1-one (6420-90-2) → 2-(4-Hydroxy-phenyl)-propionic acid (938-96-5)

Conditions	Yield
With sodium hydroxide In N-methyl-acetamide; methanol; hexane; water; ethyl acetate; toluene	82.4%

4-hydroxyphenylacetate (156-38-7) → 2-(4-Hydroxy-phenyl)-propionic acid (938-96-5)

Conditions	Yield
With sulfuric acid In methanol; silica gel; toluene	80%

α-<4-methoxy-phenyl>-propionic acid → 2-(4-Hydroxy-phenyl)-propionic acid (938-96-5)

Conditions	Yield
With phosphorus; hydrogen iodide; iodine

hydrochloride of/the/ 4-amino-hydratropic acid → 2-(4-Hydroxy-phenyl)-propionic acid (938-96-5)

Conditions	Yield
With potassium nitrite

2-(4-hydroxyphenyl)propanenitrile (21850-61-3) → 2-(4-Hydroxy-phenyl)-propionic acid (938-96-5)

Conditions	Yield
With sodium hydroxide for 5h; Heating;

1-(4-hydroxyphenyl)ethanol (93453-79-3) → 2-(4-Hydroxy-phenyl)-propionic acid (938-96-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethylformamide / 6 h / 130 °C 2: aq. NaOH / 5 h / Heating View Scheme

1-(4-methoxyphenyl)ethanone (100-06-1) → 2-(4-Hydroxy-phenyl)-propionic acid (938-96-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: aq. HBr; acetic acid / Heating 2: KBH4; KOH / methanol / Heating 3: dimethylformamide / 6 h / 130 °C 4: aq. NaOH / 5 h / Heating View Scheme

4-Hydroxyacetophenone (99-93-4) + ethynylmagnesium halide → 2-(4-Hydroxy-phenyl)-propionic acid (938-96-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: KBH4; KOH / methanol / Heating 2: dimethylformamide / 6 h / 130 °C 3: aq. NaOH / 5 h / Heating View Scheme

carbon dioxide (124-38-9) + 4-(2-bromoethyl)phenol (14140-15-9) → 2-(4-Hydroxy-phenyl)-propionic acid (938-96-5) + 4-hydroxyphenylpropionic acid (501-97-3)

Conditions	Yield
With neocuproine; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; potassium carbonate In N,N-dimethyl-formamide at 25℃; under 750.075 Torr; Irradiation; Overall yield = 70 %; Overall yield = 23.1 mg;

p-hydroxyphenethyl alcohol (501-94-0) → 2-(4-Hydroxy-phenyl)-propionic acid (938-96-5) + 4-hydroxyphenylpropionic acid (501-97-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: carbon tetrabromide; triphenylphosphine / dichloromethane; diethyl ether / 0 - 20 °C 2: potassium carbonate; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; neocuproine / N,N-dimethyl-formamide / 25 °C / 750.08 Torr / Irradiation View Scheme

methanol (67-56-1) + 2-(4-Hydroxy-phenyl)-propionic acid (938-96-5) → methyl 2-(4-hydroxyphenyl)propanoate (65784-33-0)

Conditions	Yield
With thionyl chloride at 0℃; for 3.5h; Inert atmosphere;	100%
With sulfuric acid Heating;	99%
With toluene-4-sulfonic acid for 14h; Reflux;	55%

2-(4-Hydroxy-phenyl)-propionic acid (938-96-5) → 3,5-Diiodo-4-hydroxyphenylpropionic acid (138460-07-8)

Conditions	Yield
With iodine; potassium iodide	88%

2-(4-Hydroxy-phenyl)-propionic acid (938-96-5) → 3-Nitro-4-hydroxyphenyl-α-methylacetic acid (65784-32-9, 73933-14-9, 90103-59-6)

Conditions	Yield
With nitric acid In water; acetic acid at 20℃; for 1h;	86.9%
With nitric acid; acetic acid

2-(4-Hydroxy-phenyl)-propionic acid (938-96-5) → (±)-4-(1-hydroxypropan-2-yl)phenol (55689-52-6)

Conditions	Yield
With borane-THF In tetrahydrofuran at 20℃; for 20h; Inert atmosphere;	84%

2-(4-Hydroxy-phenyl)-propionic acid (938-96-5) + benzoyl chloride (98-88-4) → C16H14O4

Conditions	Yield
With sodium hydroxide at 20℃; for 1.5h;	83%

2-(4-Hydroxy-phenyl)-propionic acid (938-96-5) + recorcinol (108-46-3) → O-desmethylangolensin (21255-69-6)

Conditions	Yield
With boron trifluoride diethyl etherate In N,N-dimethyl-formamide at 120℃; for 0.166667h; Friedel-Crafts reaction;	81%
With bis(trifluoromethanesulfonyl)amide In various solvent(s) at 90℃; for 0.0666667h; Friedel-Crafts reaction; microwave irradiation;	55%

2-(4-Hydroxy-phenyl)-propionic acid (938-96-5) + propionyl chloride (79-03-8) → C12H14O4

Conditions	Yield
With sodium hydroxide at 20℃; for 1.5h;	75%

2-(4-Hydroxy-phenyl)-propionic acid (938-96-5) + 2-hydroxyresorcinol (87-66-1) → 1-(2,3,4-dihydroxyphenyl)-2-(4'-hydroxyphenyl)-1-propanone (1173910-03-6)

Conditions	Yield
With boron trifluoride diethyl etherate In N,N-dimethyl-formamide at 120℃; for 0.166667h; Friedel-Crafts reaction;	72%

methanol (67-56-1) + 4-bromoethylbutanoate (2969-81-5) + 2-(4-Hydroxy-phenyl)-propionic acid (938-96-5) → 2-(4-(4-methoxy-4-oxobutoxy)phenyl)propanoic acid (1133001-39-4)

Conditions	Yield
With sodium methylate at 20 - 50℃;	67%

methoxyhydroquinone (824-46-4) + 2-(4-Hydroxy-phenyl)-propionic acid (938-96-5) → 1-(2,5-dihydroxy-4-methoxyphenyl)-2-(4'-hydroxyphenyl)-1-propanone (1173912-13-4)

Conditions	Yield
With boron trifluoride diethyl etherate In N,N-dimethyl-formamide at 120℃; for 0.166667h; Friedel-Crafts reaction;	23%

2-(4-Hydroxy-phenyl)-propionic acid (938-96-5) → 2-(4-Hydroxy-phenyl)-propionamide

Conditions	Yield
(i) EtOH, H2SO4, (ii) aq. NH3; Multistep reaction;

2-(4-Hydroxy-phenyl)-propionic acid (938-96-5) → (2RS)-6-O-<2-(4-hydroxyphenyl)propionyl>-D-glucose + (2RS)-β-D-fructofuranosyl 6-O-<2-(4-hydroxyphenyl)propionyl>-α-D-glucopyranoside + (2RS)-2-(4-O-β-D-glucopyranosylphenyl)propionic acid

Conditions	Yield
In ethanol; water for 72h; in a suspension cell culture of Coffea arabica;	A 7.6 mg B 17.0 mg C 2.1 mg
In ethanol; water for 72h; in a suspension cell culture of Coffea arabica;	A 17.0 mg B 7.6 mg C 2.1 mg

tetrachloromethane (56-23-5) + ethyl bromide (74-96-4) + ethanol (64-17-5) + 2-(4-Hydroxy-phenyl)-propionic acid (938-96-5) → α-<4-ethoxy-phenyl>-propionic acid

Conditions	Yield
at 115 - 120℃;

2-(4-Hydroxy-phenyl)-propionic acid (938-96-5) → methyl 2-{4-[(methylsulfonyl)oxy]phenyl}propanoate (946073-01-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 51.6 g / H2SO4 / 20 °C 2: 71 percent / pyridine / 24 h / Heating View Scheme

2-(4-Hydroxy-phenyl)-propionic acid (938-96-5) → C10H12O5S

Conditions	Yield
Multi-step reaction with 3 steps 1: 51.6 g / H2SO4 / 20 °C 2: 71 percent / pyridine / 24 h / Heating 3: 95 percent / aq. HCl; AcOH / Heating View Scheme

2-(4-Hydroxy-phenyl)-propionic acid (938-96-5) → C13H18O5S

Conditions	Yield
Multi-step reaction with 2 steps 1: 51.6 g / H2SO4 / 20 °C 2: pyridine / 24 h / Heating View Scheme

2-(4-Hydroxy-phenyl)-propionic acid (938-96-5) → C12H16O5S

Conditions	Yield
Multi-step reaction with 3 steps 1: 51.6 g / H2SO4 / 20 °C 2: pyridine / 24 h / Heating 3: 3.76 g / aq. HCl; AcOH / Heating View Scheme

2-(4-Hydroxy-phenyl)-propionic acid (938-96-5) → C16H16O5S

Conditions	Yield
Multi-step reaction with 2 steps 1: 51.6 g / H2SO4 / 20 °C 2: pyridine / 24 h / Heating View Scheme

2-(4-Hydroxy-phenyl)-propionic acid (938-96-5) → C15H14O5S

Conditions	Yield
Multi-step reaction with 3 steps 1: 51.6 g / H2SO4 / 20 °C 2: pyridine / 24 h / Heating 3: 4.74 g / aq. HCl; AcOH / Heating View Scheme

2-(4-Hydroxy-phenyl)-propionic acid (938-96-5) → methyl 2-(4-(tosyloxy)phenyl)propanoate

Conditions	Yield
Multi-step reaction with 2 steps 1: 51.6 g / H2SO4 / 20 °C 2: pyridine / 24 h / Heating View Scheme

2-(4-Hydroxy-phenyl)-propionic acid (938-96-5) → C16H16O5S

Conditions	Yield
Multi-step reaction with 3 steps 1: 51.6 g / H2SO4 / 20 °C 2: pyridine / 24 h / Heating 3: 4.72 g / aq. HCl; AcOH / Heating View Scheme

2-(4-Hydroxy-phenyl)-propionic acid (938-96-5) → methyl 2-{4-[(7-chloro-2-quinoxalinyl)oxy]phenyl}propionate (857903-64-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 99 percent / H2SO4 / Heating 2: 96 percent / K2CO3 / acetonitrile / 4 h / Heating View Scheme

Upstream product

• 21850-61-3 2-(4-hydroxyphenyl)propanenitrile 
• 501-94-0 p-hydroxyphenethyl alcohol 
• 124-38-9 carbon dioxide 
• 14140-15-9 4-(2-bromoethyl)phenol 
• 6420-90-2 2-(4-hydroxyphenyl)-1-phenylethan-1-one 
• 156-38-7 4-hydroxyphenylacetate 
• 99-93-4 4-Hydroxyacetophenone 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 93453-79-3 1-(4-hydroxyphenyl)ethanol 
• 942-54-1 2-(4-methoxyphenyl)propanoic acid 

Downstream Products

• 857903-64-1 methyl 2-{4-[(7-chloro-2-quinoxalinyl)oxy]phenyl}propionate 
• 861841-15-8 β-4-methoxycarbonyl-(α-methyl)methenylphenyl-dihydroartemisinin ether 
• 861841-29-4 β-4-carboxy-(α-methyl)methenylphenyl-dihydroartemisinin ether 
• 1173912-13-4 1-(2,5-dihydroxy-4-methoxyphenyl)-2-(4'-hydroxyphenyl)-1-propanone 
• 1173910-03-6 1-(2,3,4-dihydroxyphenyl)-2-(4'-hydroxyphenyl)-1-propanone 
• 865233-70-1 N-allyl-2-(4-hydroxyphenyl)propanamide 
• 73621-47-3 ethyl 4-benzyloxyphenylpropionate 
• 138460-11-4 (+)-α-methyl-3,5,3'-triiodothyroacetic acid 
• 138460-12-5 α-methyl-3,5,3'-triiodothyroacetic acid 
• 138460-09-0 ethyl 4-(4'-methoxyphenoxy)-3,5-diiodo-α-methylphenylacetate 
• 138460-10-3 4-(4'-hydroxyphenoxy)-3,5-diiodo-α-methylphenylacetic acid 
• 138460-08-9 ethyl 4-hydroxy-3,5-diiodo-α-methylphenylacetate 
• 946073-01-4 methyl 2-{4-[(methylsulfonyl)oxy]phenyl}propanoate 

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