882-09-7

Basic information

• Product Name: 2-(4-Chlorophenoxy)-2-methylpropionic acid
• Synonyms: CLOFIBRIC ACID;CLOFIBRINIC ACID;ASISCHEM A27485;2-(P-CHLOROPHENOXY)-2-METHYLPROPIONIC ACID;2-(4-CHLOROPHENOXY)ISOBUTYRIC ACID;2-(4-CHLOROPHENOXY)-2-METHYLPROPANOIC ACID;2-(4-CHLOROPHENOXY)-2-METHYLPROPIONIC ACID;AKOS BB-7852
• CAS NO: 882-09-7
• Molecular Formula: C₁₀H₁₁ClO₃
• Molecular Weight: 214.65
• EINECS: 212-925-9
• Product Categories: Acids and Derivatives;Organic acids;Aromatics Compounds;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Intracellular receptor;CLOFIBRIN
• Mol File: 882-09-7.mol
• Article Data: 30

Chemical Properties

• Melting Point: 120-122 °C(lit.)
• Boiling Point: 308.11°C (rough estimate)
• Flash Point: 149.8 °C
• Appearance: Pale yellow to brownish/Crystals or Crystalline Powder
• Density: 1.2413 (rough estimate)
• Refractive Index: 1.5220 (estimate)
• Storage Temp.: Store at RT
• Solubility: Chloroform, Methanol
• PKA: 3.18±0.10(Predicted)
• Merck: 14,2378
• BRN: 1874067
• CAS DataBase Reference: 2-(4-Chlorophenoxy)-2-methylpropionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-Chlorophenoxy)-2-methylpropionic acid(882-09-7)
• EPA Substance Registry System: 2-(4-Chlorophenoxy)-2-methylpropionic acid(882-09-7)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-20/21/22
• Safety Statements: 36-24/25
• WGK Germany: 3
• RTECS: UE9455000
• HazardClass: IRRITANT
• Hazardous Substances Data: 882-09-7(Hazardous Substances Data)

Usage

Description

Clofibric acid is a peroxisome proliferator-activated receptor α (PPARα) agonist (EC50 = 50 μM in a transactivation assay) and the active metabolite of clofibrate . It is formed from clofibrate by tissue and serum esterases. Dietary administration of clofibric acid (0.067-0.22%) reduces serum cholesterol, phospholipid, and triglyceride levels in rats. It decreases glutamate oxaloacetate transaminase (GOT) levels and increases glutamate pyruvate transaminase (GPT) and lactate dehydrogenase (LDH) levels, markers of xenobiotic stress, in the plasma of carp (C. carpio) when administered in tank water at a concentration of 10 μg/L. Clofibric acid has been found in wastewater effluent.

Chemical Properties

Pale Yellow Solid

Uses

Different sources of media describe the Uses of 882-09-7 differently. You can refer to the following data:
1. herbicide, antihyperlipoproteinemic, antineoplastic
2. A hypolipidemic compound

Definition

ChEBI: A monocarboxylic acid that is isobutyric acid substituted at position 2 by a p-chlorophenoxy group. It is a metabolite of the drug clofibrate.

Biological Activity

PPAR agonist. Antihyperlipoproteinemic.

Synthetic route

ETOFIBRATE (31637-97-5) → nicotinic acid (59-67-6) + Clofibric acid (882-09-7) + ethylene glycol (107-21-1)

Conditions	Yield
With hydrogenchloride; [RuCl2(CO)2(Ph2P-3-C6H4COOH)2] In methanol; water at 75℃; for 0.333333h;	A 99.1% B n/a C n/a

Clofibrate (637-07-0) → Clofibric acid (882-09-7)

Conditions	Yield
With methanol; sodium hydroxide In dichloromethane; water	94%
With sodium hydroxide In tetrahydrofuran; methanol; water	93%
Stage #1: Clofibrate With lithium hydroxide monohydrate; water In tetrahydrofuran at 20℃; for 16h; Stage #2: With hydrogenchloride In tetrahydrofuran pH=~ 2;	82%

4-chloro-phenol (106-48-9) + 1,1,1-trichloro-2-methyl-2-propanol (57-15-8) → Clofibric acid (882-09-7)

Conditions	Yield
With sodium hydroxide In acetone for 16h; Ambient temperature;	90%

2-bromo-2-methylpropionic acid (2052-01-9) + 4-chloro-phenol (106-48-9) → Clofibric acid (882-09-7)

Conditions	Yield
Stage #1: 4-chloro-phenol With sodium hydroxide In butanone at 50℃; for 1h; Stage #2: 2-bromo-2-methylpropionic acid In butanone at 50℃; for 1.5h;	87%
With sodium hydroxide In ethanol for 24h; Heating;
Multistep reaction.;
Stage #1: 4-chloro-phenol With sodium hydroxide In butanone at 50℃; for 2h; Stage #2: 2-bromo-2-methylpropionic acid In butanone at 50℃; for 12h;

acetamide (60-35-5) + 1-bromo-methylenediamine + O-(4-chlorophenyl)hydroxylamine (36637-30-6) → Clofibric acid (882-09-7)

Conditions	Yield
With sodium sulfite In hexane at 65℃; for 2.16667h; Concentration; Temperature; Reflux;	85%

N-acetylcystein (616-91-1) + clofibryl-S-acyl-glutathione → Clofibric acid (882-09-7) + clofibryl-S-acyl-N-acetylcysteine

Conditions	Yield
With buffer at 37℃; pH=7.4;	A 1% B 75%

chloroform (67-66-3) + 4-chloro-phenol (106-48-9) + acetone (67-64-1) → Clofibric acid (882-09-7)

Conditions	Yield
With sodium hydroxide for 0.416667h; grindstone chemistry;	69%
With sodium hydroxide for 24h; Ambient temperature;	59%
Stage #1: 4-chloro-phenol; acetone With sodium hydroxide at 20℃; for 0.5h; Reflux; Stage #2: chloroform In acetone for 3.5h; Reflux; Stage #3: With hydrogenchloride; water
Stage #1: 4-chloro-phenol; acetone at 20℃; for 0.0833333h; Stage #2: With sodium hydroxide at 0℃; Stage #3: chloroform for 5h; Reflux;
Stage #1: chloroform; 4-chloro-phenol; acetone With sodium hydroxide at 42 - 59℃; for 1.5h; Stage #2: With hydrogenchloride pH=2;

ethyl 2-bromoisobutyrate (600-00-0) + sodium 4-chlorophenolate (1193-00-6) → Clofibric acid (882-09-7)

Conditions	Yield
With ethanol anschliessend Erwaermen mit wss. Natronlauge;

tetrachloromethane (56-23-5) + chloroform (67-66-3) + 4-chloro-phenol (106-48-9) + acetone (67-64-1) → Clofibric acid (882-09-7)

4-chloro-phenol (106-48-9) + acetone (67-64-1) → Clofibric acid (882-09-7)

Conditions	Yield
With sodium hydroxide; chloroform

Duolip (54504-70-0) → Clofibric acid (882-09-7) + 7-(2-hydroxyethyl)theophylline (519-37-9)

Conditions	Yield
Product distribution; metabolism in vitro and in vivo in rats and dogs;

Clofibrate (637-07-0) → ethanol (64-17-5) + Clofibric acid (882-09-7)

Conditions	Yield
With sodium hydroxide; water at 30.2℃; Rate constant; Product distribution; rate constant for hydrolysis, temperature and pH dependence;

ETOFIBRATE (31637-97-5) → nicotinic acid (59-67-6) + 2-Hydroxyethyl nicotinate (3612-80-4) + Clofibric acid (882-09-7) + 2-(4-Chlorphenoxy)-2-methylpropionsaeure-2-hydroxyethylester (31637-96-4)

Conditions	Yield
With propylene glycol for 0.116667h; pharmacokinetics on intravenous infusion into dogs; other modes of administration, doses and formulations administered;

ETOFIBRATE (31637-97-5) → 2-Hydroxyethyl nicotinate (3612-80-4) + Clofibric acid (882-09-7)

Conditions	Yield
With hydrogenchloride; water at 49.8℃; Rate constant; Product distribution; rate constant for hydrolysis, temperature and pH dependence;

Perifunal (63394-05-8) → Clofibric acid (882-09-7)

Conditions	Yield
With sodium hydroxide In water

2-(4-chloro-phenoxy)-2-methyl-propionic acid [methyl-(4-nitro-benzenesulfonyl)-amino]-methyl ester → Clofibric acid (882-09-7) + 4-chloro-N-hydroxymethyl-N-methyl-benzenesulfonamide

Conditions	Yield
With sodium perchlorate; water In acetonitrile at 25℃; Rate constant; also in base and acid buffers;

2-(4-chloro-phenoxy)-2-methyl-propionic acid (benzoyl-ethoxycarbonylmethyl-amino)-methyl ester → Clofibric acid (882-09-7)

Conditions	Yield
With NADPH-generating system; rat liver homogenate at 37℃; Enzyme kinetics; Hydrolysis; Enzymatic reaction;

4-chloro-phenol (106-48-9) → Clofibric acid (882-09-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h 1.2: 16 h / 20 °C 2.1: sodium hydroxide / tetrahydrofuran; methanol; water View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 5 h / 30 - 70 °C 2: methanol; sodium hydroxide / dichloromethane; water View Scheme

Clofibric acid (882-09-7) → clofibryl chloride (5542-60-9)

Conditions	Yield
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃;	100%
With thionyl chloride; chloroform
With thionyl chloride

Clofibric acid (882-09-7) + ephedrine (299-42-3) → ephedrinium clofibrate (1234188-42-1)

Conditions	Yield
Heating; Neat (no solvent);	100%

Clofibric acid (882-09-7) + benzyl alcohol (100-51-6) → α-(4-chloro-phenoxy)-isobutyric acid benzyl ester

Conditions	Yield
With [Cl(C6F13C2H4)2SnOSn(C2H4C6F13)2Cl]2 In various solvent(s) at 150℃; for 16h;	98%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + Clofibric acid (882-09-7) → 2-(p-chlorophenoxy)-2-methyl-propionic acid succinimido ester (40249-24-9)

Conditions	Yield
With dicyclohexyl-carbodiimide In ethyl acetate	95%

Clofibric acid (882-09-7) + imino(methyl)(pyridin-2-yl)-λ6-sulfanone (76456-06-9) → N-[5-(2,5-dimethylphenoxy)-2,2-dimethylpentanoyl]-S-methyl-S-2-pyridylsulfoximine (1384980-58-8)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;	95%

[(1R,4S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid - (1R)-3H-spiro[2-benzofuran-1,3'-pyrrolidin]-3-one (869971-83-5) + Clofibric acid (882-09-7) → (1R)-1'-[2-(4-Chlorophenoxy)-2-methylpropanoyl]-3H-spiro[2-benzofuran-1,3'-pyrrolidin]-3-one

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide) at 20℃;	94%

Clofibric acid (882-09-7) + 4-amino-n-butyric acid (56-12-2) → C14H18ClNO4 (1098392-92-7)

Conditions	Yield
With chloroformic acid ethyl ester; triethylamine; sodium hydroxide In tetrahydrofuran; water at 20℃; for 1h; Cooling with ice salt bath;	90%

Clofibric acid (882-09-7) + 1,3-dibromo-propane (109-64-8) → 2-(4-chlorophenoxy)-2-methylpropionic acid 3-bromopropyl ester

Conditions	Yield
Stage #1: Clofibric acid With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: 1,3-dibromo-propane In N,N-dimethyl-formamide at 70℃; for 5h;	90%

(3-bromopropyl)amine (18370-81-5) + Clofibric acid (882-09-7) → C13H17BrClNO2

Conditions	Yield
Stage #1: Clofibric acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.166667h; Stage #2: (3-bromopropyl)amine In dichloromethane at 20℃;	90%

Clofibric acid (882-09-7) + ethyl (R)-2-((mesitylsulfinyl)imino)acetate → C22H28ClNO4S

Conditions	Yield
With 9-mesityl-2,7-dimethyl-10-phenylacridin-10-ium tetrafluoroborate; potassium carbonate at 20℃; Inert atmosphere; Irradiation; diastereoselective reaction;	90%

2-bromoethylamine (107-09-5) + Clofibric acid (882-09-7) → C12H15BrClNO2

Conditions	Yield
Stage #1: Clofibric acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.166667h; Stage #2: 2-bromoethylamine In dichloromethane at 20℃;	89%

methanol (67-56-1) + Clofibric acid (882-09-7) → 2-[4-chlorophenoxy]-2-methylpropionic acid methyl ester (55162-41-9)

Conditions	Yield
With sulfuric acid for 6h; Heating;	88%
With pyridine; thionyl chloride 1.) ether, reflux, 90 min; 2.) 60 min; Yield given. Multistep reaction;

Clofibric acid (882-09-7) + ethylene dibromide (106-93-4) → 2-(4-chlorophenoxy)-2-methylpropionic acid 2-bromoethyl ester

Conditions	Yield
Stage #1: Clofibric acid With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: ethylene dibromide In N,N-dimethyl-formamide at 70℃; for 5h;	88%

1,3-bis(2,2-dimethyl-1,3-dioxan-5-yloxy)propan-2-yl 2-(4-(4-chlorobenzoyl)phenoxy)-2-methylpropanoate (847682-00-2) + Clofibric acid (882-09-7) → 1,3-bis(2,2-dimethyl-1,3-dioxan-5-yloxy)propan-2-yl 2-(4-chlorophenoxy)-2-methylpropanoate (1043468-93-4)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2h; Inert atmosphere;	87%

4-boc-aminopiperidine + Clofibric acid (882-09-7) → tert-butyl (1-(2-(4-chlorophenoxy)-2-methylpropanoyl)piperidin-4-yl)carbamate

Conditions	Yield
Stage #1: Clofibric acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h; Cooling with ice; Stage #2: 4-boc-aminopiperidine With triethylamine In dichloromethane at 20℃; for 1h; Cooling with ice;	86%

Clofibric acid (882-09-7) + ethyl acrylate (140-88-5) → C16H17F3O5

Conditions	Yield
With tert-Amyl alcohol; t-Boc-L-valine; oxygen; palladium diacetate; potassium hydrogencarbonate at 90℃; for 24h; Schlenk technique;	85%

1,4-dibromo-butane (110-52-1) + Clofibric acid (882-09-7) → 2-(4-chlorophenoxy)-2-methylpropionic acid 4-bromobutyl ester

Conditions	Yield
Stage #1: Clofibric acid With sodium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: 1,4-dibromo-butane In N,N-dimethyl-formamide at 70℃; for 5h;	83%

Clofibric acid (882-09-7) + 1-t-Butoxycarbonylpiperazine (57260-71-6) → C19H27ClN2O4

Conditions	Yield
Stage #1: Clofibric acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 70℃; for 1h; Stage #2: 1-t-Butoxycarbonylpiperazine In N,N-dimethyl-formamide for 2h;	83%

triethanolamine (102-71-6) + Clofibric acid (882-09-7) → 2-(4-Chloro-phenoxy)-2-methyl-propionic acid; compound with 2-[bis-(2-hydroxy-ethyl)-amino]-ethanol (105377-53-5)

Conditions	Yield
In ethanol	81.8%

1-bromo-4-aminobutane (33977-38-7) + Clofibric acid (882-09-7) → C14H19BrClNO2

Conditions	Yield
Stage #1: Clofibric acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.166667h; Stage #2: 4-bromo-1-aminobutane In dichloromethane at 20℃;	81%

Clofibric acid (882-09-7) + benzyl salicylate (118-58-1) → benzyl O-<2-(p-chlorophenoxy)-2-methylpropionyl>salicylate (90296-25-6)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane Ambient temperature;	78%

2-thiazolylamine (96-50-4) + Clofibric acid (882-09-7) → 2-(4-chloro-phenoxy)-2-methyl-N-thiazol-2-yl-propionamide (404360-27-6)

Conditions	Yield
Stage #1: Clofibric acid With benzotriazol-1-ol; triethylamine In dichloromethane at 0℃; for 0.0833333h; Stage #2: 2-thiazolylamine With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 12h;	78%

trifluoroethylamine (753-90-2) + Clofibric acid (882-09-7) + acetonitrile (75-05-8) → N-acetyl-2-(4-chlorophenoxy)-2-methyl-N-(2,2,2-trifluoroethyl)propanamide

Conditions	Yield
With copper(l) iodide; tert.-butylnitrite at 25℃; for 12h; chemoselective reaction;	78%

Clofibric acid (882-09-7) + 19-O-tritylisoandrographolide → C49H53ClO7

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃;	76%

N-hydroxyphthalimide (524-38-9) + Clofibric acid (882-09-7) → 1,3-dioxoisoindolin-2-yl 2-(4-chlorophenoxy)-2-methylpropanoate

Conditions	Yield
With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; for 1h;	76%
With dmap; dicyclohexyl-carbodiimide at 20℃; for 6h; Schlenk technique; Inert atmosphere;

Upstream product

• 63394-05-8 Perifunal 
• 616-91-1 N-acetylcystein 
• 106-48-9 4-chloro-phenol 
• 60-35-5 acetamide 
• 36637-30-6 O-(4-chlorophenyl)hydroxylamine 
• 31637-97-5 ETOFIBRATE 
• 67-66-3 chloroform 
• 67-64-1 acetone 
• 637-07-0 Clofibrate 
• 57-15-8 1,1,1-trichloro-2-methyl-2-propanol 
• 2052-01-9 2-bromo-2-methylpropionic acid 
• 54504-70-0 Duolip 
• 56-23-5 tetrachloromethane 
• 600-00-0 ethyl 2-bromoisobutyrate 

Downstream Products

• 99779-88-1 N-((tetramethyl-2,2,6,6 piperidinyl)-4) (chloro-4 phenoxy)-isobutyramide 
• 146699-49-2 α-(4-chloro-phenoxy)-isobutyric acid octyl ester 
• 105377-53-5 2-(4-Chloro-phenoxy)-2-methyl-propionic acid; compound with 2-[bis-(2-hydroxy-ethyl)-amino]-ethanol 
• 82187-44-8 1-O-2-(4-Chlorphenoxy)-2-methyl-propionyl-2,3,4-tri-O-acetyl-β-D-glucopyran-methyl-uronat 
• 637-07-0 Clofibrate 
• 77444-81-6 2-(4-Chloro-phenoxy)-2-methyl-propionic acid 3-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-yl)-2-hydroxy-propyl ester 
• 60701-43-1 2-(4-Chloro-phenoxy)-1-imidazol-1-yl-2-methyl-propan-1-one 
• 61887-26-1 α-(4-Chlor-phenoxy)-isobuttersaeure-<4-chlor-anilid> 
• 167710-59-0 1-[2-(4-chlorophenoxy)-2-methyl-1-oxopropyl]-β,β,N,N-tetramethyl-4-piperidineethaneamine 
• 5658-61-7 2-(4-chlorophenoxy)-2-methylpropanamide 
• 92299-67-7 α-(4-Chlor-phenoxy)-isobuttersaeure-butylamid 
• 78027-37-9 α-(4-chloro-phenoxy)-isobutyric acid ethylamide 

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