1126-79-0

Basic information

• Product Name: Butoxybenzene
• Synonyms: n-Butyl phenyl ether,99%;Butyl phenyl ether 99%;N-BUTOXYBENZENE;N-BUTYL PHENYL ETHER;BUTOXYBENZENE;BUTYL PHENYL ETHER;1-Phenoxybutane;Benzene, butoxy-
• CAS NO: 1126-79-0
• Molecular Formula: C₁₀H₁₄O
• Molecular Weight: 150.22
• EINECS: 214-426-1
• Product Categories: Anisoles, Alkyloxy Compounds & Phenylacetates;Ethers;Organic Building Blocks;Oxygen Compounds
• Mol File: 1126-79-0.mol
• Article Data: 86

Chemical Properties

• Melting Point: −19 °C(lit.)
• Boiling Point: 210.3 °C(lit.)
• Flash Point: 180 °F
• Appearance: Clear colourless liquid
• Density: 0.935 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.334mmHg at 25°C
• Refractive Index: n20/D 1.497(lit.)
• Water Solubility: 36.6mg/L at 20℃
• BRN: 1635559
• CAS DataBase Reference: Butoxybenzene(CAS DataBase Reference)
• NIST Chemistry Reference: Butoxybenzene(1126-79-0)
• EPA Substance Registry System: Butoxybenzene(1126-79-0)

Safety Data

• Hazard Codes: N
• Statements: 51/53
• Safety Statements: 24/25-61
• RIDADR: UN3082 - class 9 - PG 3 - DOT NA1993 - Environmentally hazardous
• WGK Germany: 2
• RTECS: KN5300000
• TSCA: Yes
• Hazardous Substances Data: 1126-79-0(Hazardous Substances Data)

Usage

Description

Butoxybenzene, also known as butyl phenyl ether, is a clear, colorless liquid with distinct chemical properties. It is an organic compound that has been utilized in various applications due to its unique characteristics.

Uses

1. Used in Water Treatment Research:
Butoxybenzene is used as a model compound for studying the transformation of human pharmaceuticals detected in water during chlorine disinfection. This application helps in understanding the behavior of pharmaceutical compounds in water systems and their potential impact on the environment and human health.
2. Used in Pharmaceutical Synthesis:
Butoxybenzene is used in the synthesis of amino acids with aryl-keto function in their side-chains. This application is significant in the development of new pharmaceutical compounds and drugs, contributing to advancements in the medical field.
3. Used in Chemical Industry:
As a clear, colorless liquid, butoxybenzene can be employed in various chemical reactions and processes within the chemical industry. Its specific properties make it a valuable intermediate or reactant in the production of other chemicals and materials.

Synthesis Reference(s)

Journal of the American Chemical Society, 96, p. 2829, 1974 DOI: 10.1021/ja00816a027

Safety Profile

Moderately toxic by ingestion. See also ETHERS. When heated to decomposition it emits acrid and irritating fumes.

Purification Methods

Dissolve it in diethyl ether, washed first with 10% aqueous NaOH to remove traces of phenol, then repeatedly with distilled water, followed by evaporation of the solvent and distillation under reduced pressure [Arnett & Wu J Am Chem Soc 82 5660 1960]. [Beilstein 6 H 143, 6 I 82, 6 II 145, 6 III 550, 6 IV 558.]

InChI:InChI=1/C10H14O/c1-2-3-9-11-10-7-5-4-6-8-10/h4-8H,2-3,9H2,1H3

Upstream product

• 109-65-9 1-bromo-butane 
• 139-02-6 sodium phenoxide 
• 542-69-8 1-iodo-butane 
• 778-28-9 butyl para-toluenesulfonate 
• 109-69-3 n-Butyl chloride 
• 14503-58-3 3-methylallyloxy benzene 
• 71-36-3 butan-1-ol 
• 1912-32-9 n-butyl methanesulfonate 
• 108-95-2 phenol 
• 6738-16-5 N,N'-Dicyclohexyl-O-butyl-isoharnstoff 
• 100-67-4 potassium phenolate 
• 555-24-8 lithium phenolate 
• 3229-70-7 phenolate 
• 1120-91-8 caesium phenoxide 

Downstream Products

• 63471-88-5 4-(4-butoxy-phenyl)-4-oxo-butyric acid 
• 100976-20-3 (4-butoxy-phenyl)-[2]furyl ketone 
• 93878-13-8 2-(4-butoxy-benzoyl)-benzoic acid 
• 101684-69-9 1,5-bis-(4-butoxy-phenyl)-pentane-1,5-dione 
• 102169-33-5 butyl-{4-[4-(3-chloro-propyl)-benzyl]-phenyl}-ether 
• 39969-57-8 1-bromo-4-butoxybenzene 
• 108650-83-5 (2,4-bis-chloromethyl-phenyl)-butyl ether 
• 1138-58-5 4-n-butoxybenzenesulfonamide 
• 5736-90-3 1-(4-butoxyphenyl)propan-1-one 
• 5736-89-0 1-(4-butoxyphenyl)ethan-1-one 
• 101100-66-7 1-(4-butoxy-phenyl)-pentan-1-one 
• 100972-51-8 (4-butoxy-phenyl)-glyoxylic acid ethyl ester 
• 111825-33-3 1,1-bis-(4-butoxy-phenyl)-ethene 
• 63192-19-8 1-(4-butoxyphenyl)-2-phenylethanone 

Relevant articles and documents

OPTIMIZATION OF POLYMER-SUPPORTED OLIGOETHERS AS SOLID-LIQUID PHASE TRANSFER CATALYSTS

Oligoether residues with terminal 8-quinolyl donor groups have been loaded virtually quantitatively onto polystyrene resin supports and function more effectively than dibenzo-18-crown-6 as solid/liquid phase transfer catalysts in Williamson ether syntheses.

Stealth star polymers: A new high-loading scaffold for liquid-phase organic synthesis

(formula presented) Polyethylene glycol (PEG) has proven to be a versatile soluble-polymer support for organic synthesis, though the use of PEG has been limited by its relatively low loading (0.5 mmol/g or less). We have developed a new high-loading (1 mmol/g) soluble-star polymer based on a cyclotriphosphazene core with PEG arms that exhibit superior precipitation properties compared with those of linear PEG. Additionally, the heterocyclic core does not add interfering signals to the 1H or 13C NMR.

Use of diethoxymethane as a solvent for phase transfer-catalyzed O -alkylation of phenols

The effectiveness of diethoxymethane (DEM) as a solvent for O-alkylation of a variety of phenols under phase transfer conditions has been examined and evaluated. The reaction between 4-methoxy phenol and benzyl chloride was selected to compare reaction rates in various solvents and the efficiency of various PTCs. This reaction was further studied to develop a commercially amenable process complete with recycle streams and efficient product isolation. DEM is a good solvent for these types of phase transfer-catalyzed reactions and can be considered as an alternative solvent for dichloromethane and toluene.

Approximate rate constants for intermolecular additions of alkyl radicals to phenylsulfonyl oxime ethers

Approximate rate constants for intermolecular additions of alkyl radicals to phenylsulfonyl oxime ethers (2a and 2b) have been determined to be k(a) = 9.6 x 105 M-1 s-1 at 25°C for 2a and k(a) = 7.3 x 104 M-1 s-1 at 60°C for 2b, indicating that the additions are fast and highly efficient processes. The kinetic data have been confirmed by two competition experiments.

Methylation with Dimethyl Carbonate/Dimethyl Sulfide Mixtures: An Integrated Process without Addition of Acid/Base and Formation of Residual Salts

Dimethyl sulfide, a major byproduct of the Kraft pulping process, was used as an inexpensive and sustainable catalyst/co-reagent (methyl donor) for various methylations with dimethyl carbonate (as both reagent and solvent), which afforded excellent yields of O-methylated phenols and benzoic acids, and mono-C-methylated arylacetonitriles. Furthermore, these products could be isolated using a remarkably straightforward workup and purification procedure, realized by dimethyl sulfide‘s neutral and distillable nature and the absence of residual salts. The likely mechanisms of these methylations were elucidated using experimental and theoretical methods, which revealed that the key step involves the generation of a highly reactive trimethylsulfonium methylcarbonate intermediate. The phenol methylation process represents a rare example of a Williamson-type reaction that occurs without the addition of a Br?nsted base.

Light-Promoted Nickel Catalysis: Etherification of Aryl Electrophiles with Alcohols Catalyzed by a NiII-Aryl Complex

A highly effective C?O coupling reaction of (hetero)aryl electrophiles with primary and secondary alcohols is reported. Catalyzed by a NiII-aryl complex under long-wave UV (390–395 nm) irradiation in the presence of a soluble amine base without any additional photosensitizer, the reaction enables the etherification of aryl bromides and aryl chlorides as well as sulfonates with a wide range of primary and secondary aliphatic alcohols, affording synthetically important ethers. Intramolecular C?O coupling is also possible. The reaction appears to proceed via a NiI–NiIII catalytic cycle.