3585-49-7

Basic information

• Product Name: (2RS)-2-(4-BUTYLPHENYL)PROPANOIC ACID
• Synonyms: 4-butyl-.alpha.-methylbenzeneacetic acid;p-Butyl Ibuprofen;(2RS)-2-(4-Butylphenyl)propionic acid;2-(4-n-Butylphenyl)propionic Acid;2-(p-Butylphenyl)propionic Acid;4-Butyl-α-Methylbenzeneacetic Acid;p-Butylhydratropic Acid;Ibuprofen IMpurity-O(EP/BP)
• CAS NO: 3585-49-7
• Molecular Formula: C₁₃H₁₈O₂
• Molecular Weight: 206.28
• Product Categories: Aromatics;Inhibitors;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;PHENYL
• Mol File: 3585-49-7.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 325.8 °C at 760 mmHg
• Flash Point: 2℃
• Appearance: /
• Density: 1.031 g/cm³
• Storage Temp.: Refrigerator
• Solubility: Aqueous Base (Slightly), Chloroform (Slightly), Methanol (Slightly)
• PKA: 4.43±0.10(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: (2RS)-2-(4-BUTYLPHENYL)PROPANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (2RS)-2-(4-BUTYLPHENYL)PROPANOIC ACID(3585-49-7)
• EPA Substance Registry System: (2RS)-2-(4-BUTYLPHENYL)PROPANOIC ACID(3585-49-7)

Safety Data

• RIDADR: UN 1648 3 / PGII
• Hazardous Substances Data: 3585-49-7(Hazardous Substances Data)

Usage

Uses

An Ibuprofen (I140000) impurity.

Synthetic route

Ethyl 2-(4-butylphenyl)propanoate (3585-63-5) → (+/-)-ibuprofen (3585-49-7)

Conditions	Yield
With water; sodium hydroxide In ethanol at 20℃; for 3h;	95.5%

4-butylphenylboronic acid (145240-28-4) → (+/-)-ibuprofen (3585-49-7)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium(0); copper(I) oxide; potassium carbonate / toluene / 18 h / 80 °C / Inert atmosphere 2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 3 h / 20 °C 3.1: sodium hydroxide; water / ethanol / 3 h / 20 °C View Scheme

(+/-)-ibuprofen (3585-49-7) + 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate (74808-09-6) → 1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyloxy)-(+/-)-ibuprofen

Conditions	Yield
In dichloromethane at 20℃; for 4h; Acylation;	67%

(+/-)-ibuprofen (3585-49-7) → 1-(β-D-glucopyranosyloxy)-(+/-)-ibuprofen

Conditions	Yield
Multi-step reaction with 2 steps 1: 67 percent / CH2Cl2 / 4 h / 20 °C 2: 76 percent / H2 / Pd/C / CH2Cl2; acetone View Scheme

Upstream product

• 145240-28-4 4-butylphenylboronic acid 
• 3585-63-5 Ethyl 2-(4-butylphenyl)propanoate 

Relevant articles and documents

Preparation method of ibuprofen impurity B

The invention provides a preparation method of an ibuprofen impurity B, and belongs to the technical field of preparation of drug impurity standard substances, and the preparation method comprises thefollowing steps: step 1, carrying out coupling reaction on a compound shown in a formula 1 and ethyl bromoacetate under the action of a catalyst and a first alkali to obtain a compound shown in a formula 2; 2, performing substitution reaction on the compound shown in the formula 2 and methyl iodide under the action of second alkali to obtain a compound shown in a formula 3; and 3, hydrolyzing thecompound shown in the formula 3 under the action of a third alkali to obtain the ibuprofen impurity B. The method has the advantages of simplicity in operation, short preparation period, few byproducts, easiness in purification and high yield, the prepared ibuprofen impurity B has high purity and no obvious impurity point, meets the requirements of impurity reference substances, can be used as anibuprofen impurity B standard substance, is applied to qualitative and quantitative research and detection of the ibuprofen impurity B, and has certain significance for quality control of ibuprofen bulk drugs and related preparations thereof.