74663-48-2

Basic information

• Product Name: 2-Isopropyl-6-propylphenol (Propofol Impurity O)
• Synonyms: 2-(1-Methylethyl)-6-propylphenol;2-Isopropyl-6-propylphenol (Propofol Impurity O);Propofol Impurity O;2-Isopropyl-6-propylphenol;Brn 4383251;Phenol, 2-isopropyl-6-propyl-;2-(1-Methylethyl)-6-propyl;Propofol EP Impurity O
• CAS NO: 74663-48-2
• Molecular Formula: C₁₂H₁₈O
• Molecular Weight: 178.27
• Product Categories: Chemical Impurities;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 74663-48-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 254.537 °C at 760 mmHg
• Flash Point: 115.315 °C
• Appearance: /
• Density: 0.952 g/cm³
• Vapor Pressure: 0.0107mmHg at 25°C
• Refractive Index: 1.515
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform, Methanol (Slightly)
• PKA: 11.00±0.10(Predicted)
• CAS DataBase Reference: 2-Isopropyl-6-propylphenol (Propofol Impurity O)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Isopropyl-6-propylphenol (Propofol Impurity O)(74663-48-2)
• EPA Substance Registry System: 2-Isopropyl-6-propylphenol (Propofol Impurity O)(74663-48-2)

Safety Data

• Hazardous Substances Data: 74663-48-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 74663-48-2 differently. You can refer to the following data:
1. Propofol impurity O
2. 2-Isopropyl-6-propylphenol (Propofol EP Impurity O).

InChI:InChI=1/C12H18O/c1-4-6-10-7-5-8-11(9(2)3)12(10)13/h5,7-9,13H,4,6H2,1-3H3

Synthetic route

Conditions	Yield
With hydrogen In ethanol at 25℃; under 760 Torr;	95%
With hydrogen; palladium on activated charcoal In ethanol at 25℃; under 760 Torr; for 0.25h; Yield given;
With palladium on activated charcoal; hydrogen In methanol at 20℃; for 12h;	6 g

→ 2-(1-methylethyl)-6-propylphenol (74663-48-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1 N aq. NaOH, benzyltri-n-butylammonium bromide / CH2Cl2 / 2 h / Ambient temperature 2: 1.5 h / 250 °C 3: H2 / 10percent Pd/C / ethanol / 0.25 h / 25 °C / 760 Torr View Scheme
Multi-step reaction with 5 steps 1.1: sodium hydroxide / N,N-dimethyl-formamide / 0.25 h / 20 °C 1.2: 1.17 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere 3.1: sodium carbonate / tetrahydrofuran / 0.25 h / Inert atmosphere 3.2: 16 h / 50 °C / Inert atmosphere 4.1: toluene-4-sulfonic acid / methanol / 7 h / 20 °C / Inert atmosphere 5.1: palladium 10% on activated carbon; hydrogen / methanol / 16 h View Scheme
Multi-step reaction with 3 steps 1: potassium carbonate / acetonitrile / 8 h / 80 °C 2: N,N-diethylaniline / 1.33 h / 220 °C / Inert atmosphere 3: palladium on activated charcoal; hydrogen / methanol / 12 h / 20 °C View Scheme

Upstream product

• 71-23-8 propan-1-ol 
• 622-85-5 propoxybenzene 
• 108-95-2 phenol 
• 88-69-7 2-(1-methylethyl)phenol 
• 1510867-00-1 2-isopropyl-6-(prop-1-enyl)phenol 
• 74931-59-2 1-isopropyl-2-methoxymethyloxybenzene 
• 106-95-6 allyl bromide 
• 942-58-5 1-(1-methylethyl)-2-(2-propen-1-yloxy)benzene 
• 3354-56-1 2-allyl-6-isopropylphenol 

Downstream Products

• 342892-39-1 allyl 2-isopropyl-6-n-propylphenyl ether 
• 74663-61-9 2-isopropyl-4-allyl-6-n-propylphenol 
• 74663-56-2 2-isopropyl-4,6-di-n-propylphenol 

Relevant articles and documents

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Commercial manufacturing of propofol: Simplifying the isolation process and control on related substances

A commercially viable manufacturing process for propofol (1) is described. The process avoids acid-base neutralization events during isolation of intermediate, 2,6-di-isopropylbenzoic acid (3) and crude propofol, and thus simplifies the synthesis on industrial scale to a considerable extent. Syntheses of five impurities/related substances (USP and EP) are also described.

Alumina-Catalyzed Reactions of Hydroxyarenes and Hydroaromatic Ketones. 9. Reaction of Phenol with 1-Propanol

At 250-350 deg C in the presence of alumina, phenol (1) reacts with excess 1-propanol to give mainly (>90percent) C-alkylation to form mono- to penta-n-propylphenols plus some O-alkylations to form n-propyl aryl ethers. The principal component of the product mixture from 1 is 2,6-di-n-propylphenol (26-50 mol percent yield). With 4-n-propylphenol as substrate (instead of 1), tri-, tetra-, and penta-n-propylphenols are formed in 48-79percent combined yield. On the average, only 3percent of the total C3H7 groups in the product mixture are isopropyl ones. Deoxygenation is not observed. It is proposed that the principal products result from an SN2-type reaction mechanism which involves nucleophilic attack (variously by C-2, C-4, C-6, or O) of an adsorbed ambident phenoxide ion onto C-1 of an adsorbed n-propoxide group. n-Propylation at C-3 and C-5 of the phenol ring results from surface-catalyzed dienone-phenol rearrangement.Isopropylation may occur via a side reaction of SN1 type.