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

Chemical Properties

CLEAR COLOURLESS LIQUID

Uses

Butyl phenyl ether was used as model compound to study the transformation of human pharmaceuticals detected in water during chlorine disinfection. It was used in the synthesis of amino acids with aryl-keto function in their side-chains.

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

• 6738-16-5 N,N'-Dicyclohexyl-O-butyl-isoharnstoff 
• 108-95-2 phenol 
• 109-65-9 1-bromo-butane 
• 32580-85-1 tetraethylammonium phenolate 
• 108-86-1 bromobenzene 
• 71-36-3 butan-1-ol 
• 930-68-7 cyclohexenone 
• 603-33-8 triphenylbismuthane 
• 28899-97-0 triphenylbismuth(V) diacetate 
• 109-99-9 tetrahydrofuran 
• 24488-76-4 phenylcalcium iodide 
• 2653-89-6 4-phenoxy-1-butene 
• 4824-75-3 n-butyl methyl carbonate 
• 13360-94-6 (n-butyloxy)di(phenyl)phosphine 

Downstream Products

• 93878-13-8 2-(4-butoxy-benzoyl)-benzoic acid 
• 111825-33-3 1,1-bis-(4-butoxy-phenyl)-ethene 
• 5736-89-0 1-(4-butoxyphenyl)ethan-1-one 
• 36931-04-1 (E)-4,4’-dibutoxystilbene 
• 106-98-9 1-butylene 
• 108-95-2 phenol 
• 742095-39-2 (RS)-2-trifluoroacetamido-1-(4-butoxyphenyl)-1-propanone 
• 309757-93-5 1-(4-butoxy-phenyl)-2-phenyl-propan-1-one 
• 15494-42-5 (4-Butoxy-phenyl)-hydroxy-acetic acid methyl ester 
• 359414-76-9 4-(1-butoxyphenyl)diphenylsulfonium mesylate 
• 121239-85-8 4,7-di(4-butoxyphenyl)-6-(3,4-dimethoxyphenyl)-1,2,5-thiadiazolo<3,4-c>pyridine 
• 121239-84-7 4,7-di(4-butoxyphenyl)-6-(2-methoxyphenyl)-1,2,5-thiadiazolo<3,4-c>pyridine 
• 121239-94-9 3,4-di(4-butoxybenzoyl)-1,2,5-thiadiazole 
• 121239-91-6 di(4-butoxybenzoyl)acetylene 

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.

Radical Anion Promoted Chemoselective Cleavage of Csp2-S Bond Enables Formal Cross-Coupling of Aryl Methyl Sulfones with Alcohols

A novel formal cross-coupling of aryl methyl sulfones and alcohols affording alkyl aryl ethers via an SRN1 pathway is developed. Two marketed antitubercular drugs were efficiently prepared employing this approach as the key step. A dimsyl-anion initiated radical chain process was revealed as the major pathway. DFT calculations indicate that the formation of a radical anion via nucleophilic addition of alkoxide to the aryl radical is the key step in determining the observed chemoselectivity.

Nickel-catalyzed removal of alkene protecting group of phenols, alcohols via chain walking process

An efficient nickel-catalyzed removal of alkene protection group under mild condition with high functional group tolerance through chain walking process has been established. Not only phenolic ethers, but also alcoholic ethers can be tolerated with the retention of stereocenter adjacent to hydroxyl group. The new reaction brings the homoallyl group into a start of new type of protecting group.