14938-35-3

Basic information

• Product Name: 4-Pentylphenol
• Synonyms: P-N-PENTYLPHENOL;P-N-AMYL PHENOL;P-PENTYLPHENOL;4-N-PENTYLPHENOL;4-N-AMYLPHENOL;4-AMYLPHENOL;4-pentyl-pheno;Amyl p-hydroxybenzene
• CAS NO: 14938-35-3
• Molecular Formula: C₁₁H₁₆O
• Molecular Weight: 164.24
• EINECS: 239-015-4
• Product Categories: Liquid Crystal intermediates;Alkylphenols (Environmental Endocrine Disruptors);Analytical Chemistry;Building Blocks for Liquid Crystals;Environmental Endocrine Disruptors;Functional Materials;Phenols (Building Blocks for Liquid Crystals);Organic Building Blocks;Oxygen Compounds;Phenols;Building Blocks;C9 to C20+;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 14938-35-3.mol

Chemical Properties

• Melting Point: 23-25 °C
• Boiling Point: 342 °C
• Flash Point: 133 °C
• Appearance: clear light yellow to light brown liquid
• Density: 0.960 g/mL at 20 °C(lit.)
• Vapor Density: 5.66
• Refractive Index: n20/D 1.515
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 10.26±0.13(Predicted)
• Water Solubility: 99.99mg/L(25 oC)
• BRN: 1364424
• CAS DataBase Reference: 4-Pentylphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Pentylphenol(14938-35-3)
• EPA Substance Registry System: 4-Pentylphenol(14938-35-3)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2430 8/PG 1
• WGK Germany: 3
• RTECS: SM6750000
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 14938-35-3(Hazardous Substances Data)

Usage

Uses

Used in Antimicrobial Applications:
4-Pentylphenol is used as an antimicrobial agent for its ability to inhibit the growth of microorganisms, making it a suitable choice for preserving the freshness and safety of various products.
Used in the Chemical Industry:
4-Pentylphenol is used as an intermediate in the synthesis of liquid crystals. Its chemical properties contribute to the development of advanced materials with specific characteristics, such as improved display technology and other applications requiring liquid crystal components.

Synthesis Reference(s)

Tetrahedron Letters, 19, p. 2545, 1978 DOI: 10.1016/S0040-4039(01)94822-1

Safety Profile

Questionable carcinogen with experimental neoplas tigenic data. Moderately flammable. To fight fire, use foam, Co2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.

InChI:InChI=1/C11H16O/c1-2-3-4-5-10-6-8-11(12)9-7-10/h6-9,12H,2-5H2,1H3

Upstream product

• 110-62-3 pentanal 
• 108-95-2 phenol 
• 109-65-9 1-bromo-butane 
• 106-44-5 p-cresol 
• 14374-57-3 1-methoxy-4-(pent-1-en-1-yl)benzene 
• 638-29-9 n-valeryl chloride 
• 121219-12-3 (4-pentylphenyl)boronic acid 
• 19523-03-6 1-(4-methoxyphenyl)pentanol 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 470665-15-7 (+/-)-1-(4-benzyloxyphenyl)pent-4-en-1-ol 
• 2589-71-1 4'-hydroxyvalerophenone 

Downstream Products

• 18980-03-5 2-chloro-4-pentylphenol 
• 408328-48-3 3-Nitro-4-hydroxy-1-pentyl-benzol 
• 64191-92-0 benzoic acid-(4-pentyl-phenyl ester) 
• 4099-75-6 2,6-dinitro-4-pentyl-phenol 
• 94721-78-5 2-(4-pentylphenoxy)acetic acid 
• 6162-07-8 1-(2,3-epoxy-propoxy)-4-pentyl-benzene 
• 15300-89-7 1-chloro-3-(4-pentyl-phenoxy)-propan-2-ol 
• 59748-19-5 4-pentylphenyl 4'-pentyl(1,1'-biphenyl)-4-carboxylate 
• 61733-23-1 4-pentylphenyl 4'-heptyl(1,1'-biphenyl)-4-carboxylate 
• 61733-28-6 4-[4-(2-methylbutyl)-phenyl]-benzoic acid 4'-n-pentylphenyl ester 
• 94721-64-9 p-(p-pentylphenoxymethylene)benzoic acid 
• 111973-82-1 benzoic acid, 4-(phenylmethoxy)-4-pentylphenyl ester 
• 50649-56-4 4-pentylphenylester of 4-octyloxybenzoic acid 
• 50687-71-3 4-pentylphenyl 2-chloro-4-hydroxybenzoate 

Relevant articles and documents

C70 Fullerene-Catalyzed Metal-Free Photocatalytic ipso-Hydroxylation of Aryl Boronic Acids: Synthesis of Phenols

A metal-free C70 fullerene-catalyzed method has been developed for the ipso-hydroxylation of aryl and heteroaryl boronic acids to corresponding phenols under photocatalytic conditions. The reaction proceeds under oxygen atmosphere and the mechanistic study revealed that C70 plays a critical role in the generation of reactive oxygen species in the presence of blue light. Reactions in the presence of 18O-labelled water and oxygen confirmed the generation of reactive oxygen species from oxygen molecule. Amine used as a reductant could be recovered in the form of imine. The current method is also applicable to the synthesis of aryl ethers in one-pot two-step process. (Figure presented.).

Pd-Catalyzed Hydroxylation of Aryl Boronic Acids Using In Situ Generated Hydrogen Peroxide

Herein, we describe a benign and efficient palladium-catalyzed hydroxylation of aryl boronic acids under mild conditions, with in situ generated hydrogen peroxide from carbon monoxide, water, and oxygen. This novel procedure combines catalytic production of hydrogen peroxide with an aerobic oxidation process in a sole reaction system. This system shows good functional group tolerance and provides a benign and efficient access to a variety of functionalized phenols. Furthermore, the in situ generated hydroperoxide can be well used for triphenylphosphine oxidation, in which the TON is up to 194. Isotope labelling studies provide important mechanistic insights for this process.

POLAR NEMATIC COMPOUNDS

Polar nematic compounds, one example of which has the following structure: is a caged boron structure, where the sphere of the caged boron structure is C and each non-sphere vertex of the caged boron structure is B—H. R is H, an alkyl, a cycloalkyl, a bicycloalkyl, an alkenyl, a cycloalkenyl, a bicycloalkenyl, an alkynyl, an acyl, an aryl, an alkylaryl, a halogen, a cyano group, or an isothiocyanoto group, or R is a group that forms an ether, a ketone, an ester, a thioester, a sulfide, or a sulfone. X is COOR′ or COSR′. R′ is H, an alkyl, a cycloalkyl, a bicycloalkyl, an alkenyl, a cycloalkenyl, a bicycloalkenyl, an alkynyl, an aryl, a halogen, or a cyano group. The compounds may be used in liquid crystal displays (LCDs), and in television sets, laptop computers, computer monitors, hand-held communication devices, gaming devices, watches, cash registers, clocks, and calculators having liquid crystal displays.

Synthesis and Antimicrobial Activity of Hydroxyalkyl- and Hydroxyacyl-phenols and Their Benzyl Ethers

New phenolic compounds with hydrophilic side chains were prepared from 4-benzyloxybenzaldehyde and alkenyl magnesium bromides, followed by Sharpless dihydroxylation and hydrogenolytic removal of the benzyl group. The resulting compounds were tested in an agar diffusion assay against gram positive bacteria, gram negative bacteria, and against the fungi Candida glabrata and Aspergillus niger.

Study of bonding characteristics of some new metal complexes of salicylaldoxime (SALO) and its derivatives by far infrared and UV spectroscopy

New metal chelates of copper, lead and zinc with salicylaldoxime (SALO) and its derivatives have been prepared. The chelates have been characterized by elemental analysis, atomic absorption, infrared and UV spectroscopy. SALO behaves as a bidentate ligand forming neutral metal chelates through the phenolic oxygen and the oxime nitrogen. The M-O stretching frequencies for the transition metals show good agreement with the Irving-William's stability order Cu > Zn > Pb. Similar trend is seen for the M-N stretching frequencies in IR and the shift in transitions from UV spectral data for the metal chelates.

Metal cation-exchanged montmorillonite (Mn+-mont)-catalysed aromatic alkylation with aldehydes and ketones

The alkylation of aromatic compounds with aldehydes and ketones in the presence of a variety of metal cation-exchanged montmorillonites (Mn+-mont; Mn+ = Zr4+, Al3+, Fe3+, Zn2+, H+, Na+) has been investigated. Al3+- and Zr4+-Monts are revealed to be effective as catalysts, while no reaction takes place with Na+-mont. Al3+-Mont-catalysed alkylation of phenol with several aldehydes produces mainly or almost solely the corresponding gem-bis(hydroxyphenyl)alkanes (bisphenols) in good yields, while that with several ketones affords selectively the corresponding alkylphenols in moderate to good yields. The alkylation always occurs at the carbonyl carbon without any skeletal rearrangement and the kind of products depends much on the steric hindrance of an electrophilic intermediary carbocation. The alkylation of anisole, veratrole and p-cresol proceeds well, while that of toluene, benzene, chlorobenzene and nitrobenzene scarcely occurs.

REDUCTIVE TRANSFORMATIONS WITH TRIMETHYLSILYL CHLORIDE-SODIUM IODIDE. A NEW SYNTHESIS OF 4H-1,3-OXAZINES

1-Arylalkenes and 1-arylalkanols are reduced to arylalkanes on heating with trimethylsilyl chloride/sodium iodide in CH3CN.Under similar conditions enones, dialkylated in the β-position of the double bond, give 4H-1,3-oxazines.

Preparation and Reactions of Dianions from the Cresols

With n-BuLi/KO-t-Bu, protons are removed from the hydroxyl and methyl groups of cresols 5 to give dianions 6 in yields of 85percent (ortho), 95percent (meta), and 42percent (para).These dianions react with alkyl halides, Me3SiCl, Bu3SnCl, CO2, and oxidizing agents at carbon only and with dialkyl sulfates at both carbon and oxygen.Thus phenol derivatives bearing primary alkyl groups can be prepared from the corresponding methylphenols via dianions 6.

Aliphatic Liquid Crystals, 2. Some Nematic Derivatives of all-trans-Perhydrophenanthrene

A stereoselective synthesis of the all-trans-7-alkylperhydro-2-phenanthrenols 15a-f in 11 steps and 28 liquid crystalline esters 16 of 15a-f are described, additionally some further derivatives of 7-alkylperhydro-2-phenanthrenol.An X-ray structure analysis of ester 16ec is reported.

RECHERCHES SUR LES SUBSTANCES MESOGENES-VIII; PREPARATION ET PROPERTIES MESOMORPHES DE SERIES ISOMETRIQUES

The synthesis and the mesomorphic properties of various series of isometric mesogenic compounds are described.It is confirmed that isometric mesogenic molecules may be nematogenic and/or smectogenic according to the position of the polar rigid core.