943-45-3

Basic information

• Product Name: 2-METHYL-2-PHENOXY-PROPIONIC ACID
• Synonyms: 2-methyl-2-phenoxy-propionicaci;2-PHENOXY ISOBUTYRIC ACID;2-METHYL-2-PHENOXY-PROPIONIC ACID;AKOS B013908;ART-CHEM-BB B013908;CHEMBRDG-BB 3013908;2-Methyl-2-phenoxypropanoic acid;2-methyl-2-phenoxypropanoic acid(SALTDATA: FREE)
• CAS NO: 943-45-3
• Molecular Formula: C₁₀H₁₂O₃
• Molecular Weight: 180.2
• EINECS: 213-402-8
• Product Categories: pharmacetical
• Mol File: 943-45-3.mol
• Article Data: 18

Chemical Properties

• Melting Point: 98.0 to 102.0 °C
• Boiling Point: 289.3 °C at 760 mmHg
• Flash Point: 111.7 °C
• Appearance: /
• Density: 1.143g/cm³
• Vapor Pressure: 0.00103mmHg at 25°C
• Refractive Index: 1.525
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 3.26±0.10(Predicted)
• Water Solubility: 1000g/L at 25℃
• CAS DataBase Reference: 2-METHYL-2-PHENOXY-PROPIONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYL-2-PHENOXY-PROPIONIC ACID(943-45-3)
• EPA Substance Registry System: 2-METHYL-2-PHENOXY-PROPIONIC ACID(943-45-3)

Safety Data

• Hazard Codes: Xi
• RTECS: UF6104200
• HazardClass: IRRITANT
• Hazardous Substances Data: 943-45-3(Hazardous Substances Data)

Usage

General Description

2-Methyl-2-phenoxy-propionic acid is a chemical compound with the molecular formula C11H12O3. It is a derivative of propionic acid and is classified as a nonsteroidal anti-inflammatory drug (NSAID). 2-METHYL-2-PHENOXY-PROPIONIC ACID is commonly used as a pain reliever and anti-inflammatory medication to reduce symptoms such as swelling, pain, and fever. It works by inhibiting the production of certain chemicals in the body that cause inflammation and pain. 2-Methyl-2-phenoxy-propionic acid is often found in over-the-counter medications and prescription drugs, and its use should be carefully monitored to avoid potential side effects or interactions with other medications.

InChI:InChI=1/C10H12O3/c1-10(2,9(11)12)13-8-6-4-3-5-7-8/h3-7H,1-2H3,(H,11,12)

Synthetic route

ethyl 2-methyl-2-phenoxypropanoate (18672-04-3) → 2-methyl-2-phenoxypropionic acid (943-45-3)

Conditions	Yield
With water; sodium hydroxide In ethanol at 26℃; for 0.5h;	94.1%
With water; sodium hydroxide In ethanol at 26℃; for 0.5h;	94.1%
With potassium hydroxide
Stage #1: ethyl 2-methyl-2-phenoxypropanoate With methanol; lithium hydroxide; water In tetrahydrofuran at 20℃; Stage #2: With hydrogenchloride In tetrahydrofuran; water pH=2;
Stage #1: ethyl 2-methyl-2-phenoxypropanoate With water; lithium hydroxide In methanol for 3h; Reflux; Stage #2: With hydrogenchloride In water pH=2;

C12H15IO2 → 2,2-dimethylbenzofuran-3(2H)-one (16748-90-6) + 2-methyl-2-phenoxypropionic acid (943-45-3)

Conditions	Yield
Stage #1: C12H15IO2 With N1,N1,N12,N12-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a:2,1'-c][1,4]diazepine-2,12-diamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Stage #2: With potassium hydroxide; water In methanol at 50℃; for 12h;	A 83% B 8.3%

ethyl 2-(2-iodophenoxy)-2-methylpropanoate → 2,2-dimethylbenzofuran-3(2H)-one (16748-90-6) + 2-methyl-2-phenoxypropionic acid (943-45-3)

Conditions	Yield
Stage #1: ethyl 2-(2-iodophenoxy)-2-methylpropanoate With N1,N1,N12,N12-tetramethyl-7,8-dihydro-6H-dipyrido[1,2-a:2,1'-c][1,4]diazepine-2,12-diamine In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Stage #2: With potassium hydroxide In methanol; water at 50℃; for 12h; Inert atmosphere;	A 83% B 8%

2-bromo-2-methylpropionic acid (2052-01-9) + phenol (108-95-2) → 2-methyl-2-phenoxypropionic acid (943-45-3)

Conditions	Yield
Stage #1: phenol With sodium hydroxide In butanone at 50℃; for 2h; Stage #2: 2-bromo-2-methylpropionic acid In butanone at 50℃; for 12h;	81%
Multistep reaction.;

1,1,1-trichloro-2-methyl-2-propanol (57-15-8) + phenol (108-95-2) → 2-methyl-2-phenoxypropionic acid (943-45-3)

Conditions	Yield
With sodium hydroxide In acetone at 0 - 20℃; for 4h;	38%

(1,1-dimethyl-pent-4-en-1-ynyl)-phenyl ether → 2-methyl-2-phenoxypropionic acid (943-45-3) + oxalic acid (144-62-7)

Conditions	Yield
With potassium permanganate; sodium carbonate

tetrachloromethane (56-23-5) + acetone (67-64-1) + 1,1,1-trichloro-2-methyl-2-propanol (57-15-8) + phenol (108-95-2) → 2-methyl-2-phenoxypropionic acid (943-45-3)

tetrachloromethane (56-23-5) + chloroform (67-66-3) + acetone (67-64-1) + phenol (108-95-2) → 2-methyl-2-phenoxypropionic acid (943-45-3)

tetrachloromethane (56-23-5) + 2-methyllactic acid (594-61-6) + acetone (67-64-1) + phenol (108-95-2) → 2-methyl-2-phenoxypropionic acid (943-45-3)

tetrachloromethane (56-23-5) + acetone (67-64-1) + phenol (108-95-2) → 2-methyl-2-phenoxypropionic acid (943-45-3)

Conditions	Yield
With sodium hydroxide

chloroform (67-66-3) + acetone (67-64-1) + phenol (108-95-2) → 2-methyl-2-phenoxypropionic acid (943-45-3)

Conditions	Yield
With sodium hydroxide
With potassium hydroxide
Stage #1: acetone; phenol With sodium hydroxide at 20℃; for 0.5h; Reflux; Stage #2: chloroform In acetone for 3.5h; Reflux; Stage #3: With hydrogenchloride; water

2-methyllactic acid (594-61-6) + phenol (108-95-2) → 2-methyl-2-phenoxypropionic acid (943-45-3)

Conditions	Yield
With sodium hydroxide; acetone

sodium phenoxide (139-02-6) → 2-methyl-2-phenoxypropionic acid (943-45-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 160 °C 2: aqueous KOH-solution View Scheme

cyclohexane-petroleum ether + Clofibric acid (882-09-7) → 2-methyl-2-phenoxypropionic acid (943-45-3)

Conditions	Yield
With potassium hydroxide In 1,4-dioxane; methanol; water
With potassium hydroxide In 1,4-dioxane; methanol; water

ethyl 2-methyl-2-phenoxypropanoate (18672-04-3) → 2,2-dimethylbenzofuran-3(2H)-one (16748-90-6) + 2-methyl-2-phenoxypropionic acid (943-45-3)

Conditions	Yield
With potassium hydroxide In methanol; water for 12h;

phenol (108-95-2) → 2-methyl-2-phenoxypropionic acid (943-45-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: caesium carbonate / acetonitrile / 16 h / 25 °C / Reflux 2: sodium hydroxide; water / ethanol / 0.5 h / 26 °C View Scheme
Multi-step reaction with 2 steps 1: caesium carbonate / acetonitrile / 16 h / 25 °C / Reflux 2: sodium hydroxide; water / ethanol / 0.5 h / 26 °C View Scheme

acetone (67-64-1) + benzoic acid (65-85-0) → 2-methyl-2-phenoxypropionic acid (943-45-3)

Conditions	Yield
With sodium hydroxide In chloroform for 3h; Heating;	1.34 g

lead(II) carbonate (790616-79-4) + 2-methyl-2-phenoxypropionic acid (943-45-3) → lead phenoxyisobutyrate

Conditions	Yield
In ethanol; water reflux (4 h), solvent evapn.; elem. anal.;	99.9%

2-methyl-2-phenoxypropionic acid (943-45-3) + benzylamine (100-46-9) → N-Benzyl-2-methyl-2-phenoxy-propionamide (128966-05-2)

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane	94%

2-methyl-2-phenoxypropionic acid (943-45-3) + ethyl acrylate (140-88-5) → C15H18O5

Conditions	Yield
With tert-Amyl alcohol; t-Boc-L-valine; oxygen; palladium diacetate; potassium hydrogencarbonate at 90℃; for 24h; Schlenk technique;	91%

methanol (67-56-1) + 7-amino-2,4-dimethyl-1,8-naphthyridine (39565-07-6) + 2-methyl-2-phenoxypropionic acid (943-45-3) → (5,7-dimethyl-1,8-naphthyridine-2-amine)2:(2-methyl-2-phenoxypropanoic acid)2:CH3OH

Conditions	Yield
for 0.25h;	89.04%

benzoimidazole (51-17-2) + 2-methyl-2-phenoxypropionic acid (943-45-3) → benzimidazole 2-methyl-2-phenoxypropanoic acid

Conditions	Yield
In methanol	88.51%

[2,2]bipyridinyl (366-18-7) + 2-methyl-2-phenoxypropionic acid (943-45-3) + zinc(II) acetate dihydrate (5970-45-6) → [Zn(2,2′-bipyridine)(2-methyl-2-phenoxypropanoate)2·H2O]·H2O

Conditions	Yield
Stage #1: 2-methyl-2-phenoxypropionic acid; zinc(II) acetate dihydrate In methanol at 60℃; for 0.333333h; Stage #2: [2,2]bipyridinyl In methanol at 60℃; for 0.1h;	77.93%

2-methyl-2-phenoxypropionic acid (943-45-3) + hexamethylenetetramine (100-97-0) + cadmium(II) acetate dihydrate (5743-04-4) → Cd(hexamethylenetetramine)2(2-methyl-2-phenoxypropionate)2(H2O)2

Conditions	Yield
Stage #1: 2-methyl-2-phenoxypropionic acid; hexamethylenetetramine; cadmium(II) acetate dihydrate In methanol; ethanol at 20℃; for 2h; Stage #2: With ammonia In methanol; ethanol	77.49%

[2,2]bipyridinyl (366-18-7) + cadmium(II) chloride dihydrate + 2-methyl-2-phenoxypropionic acid (943-45-3) + water (7732-18-5) → [Cd(2,2′-bipyridine)2(2-methyl-2-phenoxypropanoate)2]·H2O

Conditions	Yield
Stage #1: cadmium(II) chloride dihydrate; 2-methyl-2-phenoxypropionic acid; water at 60℃; for 0.333333h; Stage #2: [2,2]bipyridinyl at 60℃; for 0.1h;	72.4%

3-(3,4-diossimetilenefenil)-4-ammino-5-mercapto-4H-1,2,4-triazolo (67572-54-7) + 2-methyl-2-phenoxypropionic acid (943-45-3) → 3-Benzo[1,3]dioxol-5-yl-6-(1-methyl-1-phenoxy-ethyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole (106690-20-4)

Conditions	Yield
With trichlorophosphate Heating;	68%

2-methyl-2-phenoxypropionic acid (943-45-3) + L-carnitine (541-15-1) → l-Carnitine phenoxyisobutyrate

Conditions	Yield
With sodium hydroxide In water; acetone	60%

2-methyl-2-phenoxypropionic acid (943-45-3) + 19-O-tritylisoandrographolide → C49H54O7

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	58.3%

2-methyl-2-phenoxypropionic acid (943-45-3) + (1S,3S)-isopropyl 3-((6-(5-(aminomethyl)-1-methyl-1H-1,2,3-triazol-4-yl)-2-methylpyridin-3-yl)oxy)cyclohexane-1-carboxylate → (1S,3S)-3-((2-methyl-6-(1-methyl-5-((2-methyl-2-phenoxypropanamido)methyl)-1H-1,2,3-triazol-4-yl)pyridin-3-yl)oxy)cyclohexane-1-carboxylic acid

Conditions

Yield

Stage #1: 2-methyl-2-phenoxypropionic acid With 1-chloro-1-(dimethylamino)-2-methyl-1-propene In dichloromethane at 20℃; for 0.166667h; Stage #2: (1S,3S)-isopropyl 3-((6-(5-(aminomethyl)-1-methyl-1H-1,2,3-triazol-4-yl)-2-methylpyridin-3-yl)oxy)cyclohexane-1-carboxylate With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 1h; Stage #3: With lithium hydroxide monohydrate In tetrahydrofuran; methanol; water at 20℃;

47%

2-methyl-2-phenoxypropionic acid (943-45-3) + 1,4-dimethyl but-2-enedioate (23055-10-9) → dimethyl 2-(2-phenoxypropan-2-yl)succinate

Conditions	Yield
With potassium phosphate; PrPPTNO; water In acetonitrile at 25 - 32℃; for 16h; Inert atmosphere; Schlenk technique; Darkness; UV-irradiation;	26%

formic acid (64-18-6) + 2-methyl-2-phenoxypropionic acid (943-45-3) + 1-amino-3-(3,4-dihydroisoquinoline-2(1H)-yl)propan-2-ol (954279-15-3) → N-(3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl)-2-methyl-2-phenoxypropanamide formate salt

Conditions	Yield
Stage #1: 2-methyl-2-phenoxypropionic acid; 1-amino-3-(3,4-dihydroisoquinoline-2(1H)-yl)propan-2-ol With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 24℃; for 16h; Stage #2: formic acid	8%

ethanol (64-17-5) + 2-methyl-2-phenoxypropionic acid (943-45-3) → ethyl 2-methyl-2-phenoxypropanoate (18672-04-3)

Conditions	Yield
With hydrogenchloride

2-methyl-2-phenoxypropionic acid (943-45-3) → 2-methyl-2-phenoxy-propionyl chloride (50389-29-2)

Conditions	Yield
With phosphorus pentachloride
With thionyl chloride
With thionyl chloride

2-methyl-2-phenoxypropionic acid (943-45-3) → 2-Methyl-2-(2-nitrophenoxy)propanoic Acid (10514-62-2)

Conditions	Yield
With nitric acid

2-methyl-2-phenoxypropionic acid (943-45-3) → poly(methacrylic acid) (79-41-4) + phenol (108-95-2)

Conditions	Yield
bei der Destillation;

Upstream product

• 18672-04-3 ethyl 2-methyl-2-phenoxypropanoate 
• 882-09-7 Clofibric acid 
• 57-15-8 1,1,1-trichloro-2-methyl-2-propanol 
• 108-95-2 phenol 
• 139-02-6 sodium phenoxide 
• 67-66-3 chloroform 
• 67-64-1 acetone 
• 56-23-5 tetrachloromethane 
• 594-61-6 2-methyllactic acid 
• 65-85-0 benzoic acid 
• 2052-01-9 2-bromo-2-methylpropionic acid 

Downstream Products

• 50389-29-2 2-methyl-2-phenoxy-propionyl chloride 
• 10514-62-2 2-Methyl-2-(2-nitrophenoxy)propanoic Acid 
• 79-41-4 poly(methacrylic acid) 
• 108-95-2 phenol 
• 128966-05-2 N-Benzyl-2-methyl-2-phenoxy-propionamide 
• 201230-82-2 carbon monoxide 
• 67-64-1 acetone 
• 40665-74-5 dimethyl 3-methyl-3-phenoxy-2-oxo-butylphosphonate 
• 1309358-88-0 2-methyl-2-(phenyloxy)-N-[2-(1H-1,2,4-triazol-1-yl)-5-(trifluoromethyl)phenyl]propanamide 
• 1393577-77-9 C₃₄H₃₂FNO₆ 
• 1616074-91-9 N-(3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl)-2-methyl-2-phenoxypropanamide 
• 18672-04-3 ethyl 2-methyl-2-phenoxypropanoate 

Relevant articles and documents

Exploration of a 14-3-3 PPI Pocket by Covalent Fragments as Stabilizers

The systematic discovery of functional fragments binding to the composite interface of protein complexes is a first critical step for the development of orthosteric stabilizers of protein-protein interactions (PPIs). We have previously shown that disulfide trapping successfully yielded covalent stabilizers for the PPI of 14-3-3 with the estrogen receptor ERα. Here we provide an assessment of the composite PPI target pocket and the molecular characteristics of various fragments binding to a specific subpocket. Evaluating structure-activity relationships highlights the basic principles for PPI stabilization by these covalent fragments that engage a relatively large and exposed binding pocket at the protein/peptide interface with a "molecular glue"mode of action.

PRMT5 INHIBITORS AND USES THEREOF

Described herein are compounds of Formula (I), pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof. Compounds of the present invention are useful for inhibiting PRMT5 activity. Methods of using the compounds for treating PRMT5-mediated disorders are also described.

PRMT5 INHIBITORS CONTAINING A DIHYDRO- OR TETRAHYDROISOQUINOLINE AND USES THEREOF

Described herein are compounds of Formula (A), pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof. Compounds of the present invention are useful for inhibiting PRMT5 activity. Methods of using the compounds for treating PRMT5- mediated disorders are also described.