Butoxybenzene

• CAS: 1126-79-0
• Catalog Number: ACM1126790
• Category: Main Products
• Molecular Weight: 150.22
• Molecular Formula: C₁₀H₁₄O
• Synonyms: n-Butyl phenyl ether; Butoxyphenyl; n-butyloxybenzene; Phenyl butyl ether; BUTYL PHENYL ETHER; Ether,butyl phenyl; Butyl Phenyl Ether; Benzene,butoxy
• IUPAC Name: butoxybenzene
• Canonical SMILES: CCCCOC1=CC=CC=C1
• InChI Key: YFNONBGXNFCTMM-UHFFFAOYSA-N
• Boiling Point: 210.2ºC
• Melting Point: -19ºC
• Flash Point: 82ºC
• Density: 0.935
• Appearance: Colourless clear liquid
• Application: Butoxybenzene is utilized as a model compound to investigate the degradation of human pharmaceuticals in water through chlorine disinfection. Additionally, it is employed in the production of amino acids containing aryl-keto groups in their side chains.
• EC Number: 214-426-1
• Exact Mass: 150.10400
• Safety Description: S24/25
• Stability: Stable under normal temperatures and pressures.
• WGK Germany: 2

Case Study

Liquid-Liquid-Solid Phase Transfer Catalytic Synthesis Method of N-Butyl Phenyl Ether

Hsu-Chin Hsiao, et al. J Chem Technol Biotechnol, 2005, 80(3), 299-306.

n-Butyl phenyl ether (ROPh) can be synthesized from n-butyl bromide (RBr) and sodium phenolate (NaOPh) by liquid-liquid-solid phase transfer using a continuous flow stirred vessel reactor (CFSVR). The three-phase catalytic system involves the immobilization of tri-n-butylamine and the three-phase catalysis in CFSVR.
Three-phase catalysis of n-butyl phenyl ether in CFSVR
· The organic solution was introduced at the bottom while the aqueous solution was added at the top. Catalyst particles were located near the interface between the organic and aqueous phases when the solutions were stationary, but did not flow out when the solutions were agitated.
· The CFSVR was operated following a specific procedure. Firstly, an aqueous solution containing sodium phenolate (NaOPh) and an organic solution with RBr, n-dodecane, and toluene (as a solvent) were prepared and stored.
· Secondly, 110 cm3 aliquots of the aqueous and organic solutions, along with a designated amount of triphase catalyst, were placed into the reactor.
· Once the conversion rate reached the expected value around 50 minutes, the prepared aqueous and organic feed solutions were continuously supplied to the reactor, with the same amount withdrawn at the same rate. The concentration of RBr in the organic outlet solution was monitored every 2 hours by analyzing three samples (0.1 cm3 each) each time.

Butoxybenzene for dye-sensitized solar cells

Wu, Quan-Ping, et al. Solar energy 86.2 (2012): 764-770.

Three organic dyes XS24-26 containing N,N-dimethylaniline and butoxybenzene were designed, synthesized and applied to dye-sensitized solar cells (DSSCs). The effect of secondary electron-donating groups on the performance of DSSCs was discussed. Dimethylaniline is beneficial for expanding the absorption spectrum, while butoxybenzene is beneficial for suppressing electron recombination. XS26 containing butoxybenzene and thiophene units has a maximum power efficiency g of 5.67%, a Jof of 12.36 mA cm, a Vof of 680 mV, and a ff of 0.67.
It shows a strong absorption band around 300-500 nm. XS25 shows two visible bands, appearing at 310 and 424 nm. For XS24, the two absorption peaks are red-shifted to 324 and 440 nm, respectively, compared with XS25. The results show that N,N-dimethylaniline as a secondary electron-donating group is beneficial for expanding the light absorption spectrum compared with butoxybenzene. When the thiophene unit is introduced to generate XS26, the two absorption peaks are further red-shifted to appear at 326 and 460 nm, respectively, which is due to the expansion of the conjugated system. The maximum molar absorption coefficient (e) of XS24 containing N,N-dimethylaniline in the visible light region is 15,400 Mcm, which is higher than the corresponding value (13,700 Mcm) of XS25 with alkoxy substituents on the benzene ring. The maximum molar extinction coefficient (e) of the dye XS26 is 21,100 Mcm. The increased p-conjugation length by the introduction of the thiophene unit is the reason for the increase in the molar extinction coefficient. The good absorption coefficient of the dye indicates that it has a high light collection ability. The emission spectrum of XS24-26 in chloroform is also shown in Figure 1. The excitation transition energy (E) is roughly estimated by the intersection of the absorption and emission spectra.

Butoxybenzene is used in the ligand exchange reaction of ferrocene with substituted benzenes

Okada, Yutaka, and Yoshiharu Kato. International Journal of Organic Chemistry 12.1 (2022): 1-10.

The ligand exchange reaction is one of the typical reactions of ferrocene. The ligand exchange reaction of ferrocene with various substituted benzenes was studied using aluminum chloride as a catalyst. The reaction yields of the products with alkanoylbenzenes and alkoxybenzenes such as butoxybenzene were low due to the coordination of aluminum chloride with the oxygen atom of the benzene substituent, while the reaction activity of o-dimethoxybenzene was low compared with that of o-dimethoxybenzene and p-dimethoxybenzene, which may be due to the large π electron shift of its benzene ring.
The products were obtained when anisole and butoxybenzene were used regardless of the solvent and temperature, but the highest yields were obtained in both cases when 1,2-dichloroethane was used as the solvent and the Fc:arene:AlCl3 ratio was 1:1:2. For the reaction of anisole and butoxybenzene, the products were obtained in higher yields when the Fc:arene:AlCl3 ratio was 1:1:2 instead of 1:1:1; the same was true for alkylbenzenes and alkanoylbenzenes. This is because, like the carbonyl oxygen of alkanoylbenzenes, the unshared electron pair on the alkoxy oxygen atom is attacked by aluminum chloride. In addition, anisole afforded higher product yields than butoxybenzene, probably because of the shorter carbon chain of the former; this was also observed for alkanoylbenzenes. The ligand exchange reaction of ferrocene with o-dimethoxybenzene did not produce the desired product, whereas the ligand exchange reactions with m- and p-dimethoxybenzenes produced the desired products (Table 4). Similar to the reaction with monoalkoxybenzenes, the product yields of the reactions with m- and p-dimethoxybenzenes were higher when the amount of aluminum chloride was doubled. In addition, m-dimethoxybenzene was less reactive than p-dimethoxybenzene.

Custom Q&A

What is the molecular formula of butoxybenzene?

The molecular formula of butoxybenzene is C10H14O.

What are the synonyms for butoxybenzene?

The synonyms for butoxybenzene are BUTYL PHENYL ETHER, 1126-79-0, and n-Butyl phenyl ether.

Is butoxybenzene a natural product?

Yes, butoxybenzene is a natural product found in Cichorium endivia.

What is the molecular weight of butoxybenzene?

The molecular weight of butoxybenzene is 150.22 g/mol.

What is the IUPAC name of butoxybenzene?

The IUPAC name of butoxybenzene is butoxybenzene.

What is the InChI of butoxybenzene?

The InChI of butoxybenzene is InChI=1S/C10H14O/c1-2-3-9-11-10-7-5-4-6-8-10/h4-8H,2-3,9H2,1H3.

What is the InChIKey of butoxybenzene?

The InChIKey of butoxybenzene is YFNONBGXNFCTMM-UHFFFAOYSA-N.

What is the canonical SMILES of butoxybenzene?

The canonical SMILES of butoxybenzene is CCCCOC1=CC=CC=C1.

What is the CAS number of butoxybenzene?

The CAS number of butoxybenzene is 1126-79-0.

What is the XLogP3 value of butoxybenzene?

The XLogP3 value of butoxybenzene is 3.5.