49763-65-7

Basic information

• Product Name: 4-PENTYLBENZOYL CHLORIDE
• Synonyms: P-PENTYLBENZOYL CHLORIDE;4-(N-PENTYL)BENZOYL CHLORIDE;4-N-AMYLBENZOYL CHLORIDE;4-PENTYLBENZOYL CHLORIDE;4-PENTYLBENZENE-1-CARBONYL CHLORIDE;LABOTEST-BB LT00159030;4-pentyl-benzoylchlorid;4-N-PENTYLBENZOYL CHLORIDE / 4-N-AMYLBENZOYL CHLORIDE
• CAS NO: 49763-65-7
• Molecular Formula: C₁₂H₁₅ClO
• Molecular Weight: 210.7
• EINECS: 256-478-8
• Product Categories: Acid Halides;Carbonyl Compounds;Organic Building Blocks
• Mol File: 49763-65-7.mol

Chemical Properties

• Boiling Point: 144-145°C 10mm
• Flash Point: >230 °F
• Appearance: clear light yellow liquid
• Density: 1.036 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00234mmHg at 25°C
• Refractive Index: n20/D 1.53(lit.)
• Water Solubility: Reacts with water.
• Sensitive: Moisture Sensitive
• BRN: 2207887
• CAS DataBase Reference: 4-PENTYLBENZOYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-PENTYLBENZOYL CHLORIDE(49763-65-7)
• EPA Substance Registry System: 4-PENTYLBENZOYL CHLORIDE(49763-65-7)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 49763-65-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Pentylbenzoyl chloride is used as a synthetic intermediate for the preparation of 3-O-acyl derivatives by reacting with betulinic acid. Betulinic acid is a naturally occurring pentacyclic triterpenoid that has been found to possess various pharmacological properties, including anti-inflammatory, anti-cancer, and anti-HIV activities. The 3-O-acyl derivative synthesized using 4-pentylbenzoyl chloride can potentially enhance the bioavailability and therapeutic effects of betulinic acid, making it a valuable compound in the development of new drugs.
Used in Chemical Industry:
4-Pentylbenzoyl chloride is also used as an intermediate in the synthesis of liquid crystals. Liquid crystals are a unique state of matter that exhibits properties between those of conventional liquids and solid crystals. They have a wide range of applications, including display technologies, such as televisions, computer monitors, and smartphones, as well as in various sensors and optical devices. The use of 4-pentylbenzoyl chloride in the production of liquid crystals contributes to the development of advanced materials with improved performance and functionality.

InChI:InChI=1/C12H15ClO/c1-2-3-4-5-10-6-8-11(9-7-10)12(13)14/h6-9H,2-5H2,1H3

Upstream product

• 79-37-8 oxalyl dichloride 
• 538-68-1 pentylbenzene 
• 26311-45-5 4-pentylbenzoic acid 

Downstream Products

• 64408-91-9 4-Pentyl-thiobenzoic acid S-(4-hexyl-phenyl) ester 
• 61733-46-8 4-n-pentylbenzoic acid 4'-(4-isopropylphenyl)-phenyl ester 
• 64408-92-0 4-Pentyl-thiobenzoic acid S-(4-hexyloxy-phenyl) ester 
• 72997-59-2 5-(4-methoxy-phenyl)-2-(4-pentyl-phenyl)-thiazole 
• 59748-35-5 4-n-pentylbenzoic acid 4'-(4-n-hexylphenyl)-phenyl ester 
• 6853-57-2 4-pentylbenzaldehyde 
• 74316-63-5 4-Pentyl-benzoic acid 4-(6-oxo-5-pentyl-6H-pyran-2-yl)-phenyl ester 
• 70997-10-3 2-Chloro-4-(4-pentyl-benzoyloxy)-benzoic acid 4-cyano-phenyl ester 
• 86786-89-2 3-fluoro-4-cyanophenyl-4'-n-pentylbenzoate 
• 140860-49-7 4-Pentyl-benzoic acid 3'-chloro-4'-cyano-biphenyl-4-yl ester 

Relevant articles and documents

[closo-1-CB11H11-1-Ph]- as a structural element for ionic liquid

Ion pairs 2[Pyr] and 3[Pyr] containing [closo-1-CB11H 11-1-Ph]- as the structural element were synthesized and their liquid crystalline properties were investigated by thermal and optical methods. Their mesogenic behavior was compared to that of the analogous series 1[Pyr] having a COO linking group between the benzene ring and the cluster, and the observed structure-property relationships are discussed in the context of general trends in related non-ionic liquid crystals.

The Discovery of Novel ACA Derivatives as Specific TRPM2 Inhibitors that Reduce Ischemic Injury Both in Vitro and in Vivo

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Identification of Anti-Mycobacterial Biofilm Agents Based on the 2-Aminoimidazole Scaffold

Tuberculosis (TB) remains a significant global health problem for which new therapeutic options are sorely needed. The ability of the causative agent, Mycobacterium tuberculosis, to reside within host macrophages and form biofilm-like communities contributes to the persistent and drug-tolerant nature of the disease. Compounds that can prevent or reverse the biofilm-like phenotype have the potential to serve alongside TB antibiotics to overcome this tolerance, and decrease treatment duration. Using Mycobacterium smegmatis as a surrogate organism, we report the identification of two new 2-aminoimidazole compounds that inhibit and disperse mycobacterial biofilms, work synergistically with isoniazid and rifampicin to eradicate preformed M. smegmatis biofilms in vitro, are nontoxic toward Galleria mellonella, and exhibit stability in mouse plasma.

Synthesis, structure, and mesomorphism of novel liquid crystalline acrylate monomers and polymers

A series of novel liquid crystalline monomers (M1-M8) and side chain polymers base polyacrylate backbone were synthesized. The chemical structures were characterized by FT-IR and 1H-NMR spectra. The mesomorphism and thermal behavior was investigated by polarizing optical microscopy, differential scanning calorimetry, and thermogravimetric analysis. The relationships of structure and mesomorphism are discussed in detail. The eight monomers and their corresponding polymers all show enantiotropic nematic phase. With increasing the spacer length or flexibility of the terminal group, the melting temperature (Tm) and isotropic temperature (Ti) of the corresponding monomers and polymers all decreased. However, with increasing the rigidity of the mesogenic core, Tm and Ti of the corresponding monomers and polymers all increased. TGA showed that all the polymers obtained in this study had excellent thermal stability.

Synthesis and characterization of new nematic liquid crystalline compounds-based thiophene units

Four new liquid crystalline thiophene compounds (M1-M4) with a long flexible spacer were prepared. Their structures were characterized by Fourier transform infrared and proton nuclear magnetic resonance. The mesomorphism and thermal stability were investigated with differential scanning calorimetry, polarizing optical microscopy, and thermogravimetric analysis. The photo-physical properties were evaluated using ultraviolet/visible spectroscopy and photoluminescence. M1-M4 all showed thermotropic mesogenic properties with excellent thermal stability, and exhibited nematic threaded texture, droplet texture, and Schlieren texture on heating and cooling cycles. The effect of flexible spacer and terminal groups on mesomorphic and spectroscopic property is discussed. The experimental results demonstrated that the tendency toward melting temperature (Tm) decreased, while isotropic temperature (Ti) increased with increasing the flexible spacer length. In CHCl3 solution, these thiophene compounds displayed an intense broad absorption band peaking within 230-340 nm and a maximum fluorescent emission wavelength at 426-439 nm.

Synthesis, photo-sensitive and electrochemical properties of rod-like aromatic aldehyde with azo bridge

Eight new rod-like liquid crystal molecules composed by a long rigid core of three six-member rings (cyclohexane ring or benzene ring), azo, ester and terminal aldehyde groups have been prepared. These rod-like liquid crystalline molecules were designed to construct new structures to further study photo-isomerization in their mesophases. All the compounds have been characterized based on their basic spectral data, differential scanning calorimeter (DSC) and hot stage polarizing optical microscope (HS-POM). The result showed that all the molecules, even those with the shortest terminal methyl group, have liquid crystalline properties. Their mesophases are nematic within the temperature ranges from 85 to 145°C. They exhibit photo-sensitivities not only in methanol solutions but also in a mesophase when exposed to UV light. The highest occupied orbital (HOMO) and the lowest unoccupied orbital (LUMO) and the differences between the frontier molecular orbitals (Eg) of these compounds were determined by cyclic voltammetry. The effect of even-odd carbon number of the terminal straight alkyl chain on the UV spectral data and the Eg were observed. The difference between the Eg of these compounds are in excellent agreement with the difference of their maximum absorption wavelength in UV spectra.

Discovery and characterization of potent thiazoles versus methicillin- and vancomycin-resistant Staphylococcus aureus

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A new series of fluconazole analogues of 1-(1H-1,2,4-triazol-1-yl)-2-(2,4- difluoro-phenyl)-3-4-(substituted-heterocyclic ring-1H-1,2,3- triazol-1-yl)-2-propanols (1-10) were designed, synthesized and evaluated as antifungal agents. Preliminary antifungal tests showed that most of the title compounds exhibited moderate activity with broad spectrum against eight human pathogenic fungi in vitro, compounds 1 and 6 had the best antifungal activity against Candida albicans with the value of MIC80 = 0.5 μg/mL respectively.

Vanilloids. 1. Analogs of Capsaicin with Antinociceptive and Antiinflammatory Activity

As part of a program to establish structure-activity relationships for vanilloids, analogs of the pungent principle capsaicin, the alkyl chain portion the parent structure (and related compounds derived from homovanillic acid) was varied.In antinociceptive and antiinflammatory assays (rat and mouse hot plate and croton oil-inflamed mouse ear), compounds with widely varying alkyl chain structures were active.Short-chain compounds were active by systemic administration in the assays mentioned above but they retained the high pungency and acute toxicity characteristic of capsaicin.In contrast, the long chain cis-unsaturates, NE-19550 (vanillyloleamide) and NE-28345 (oleylhomovanillamide), were orally active, less pungent, and less acutely toxic than capsaicin.The potential of these compounds as antiinflammatory/analgesic agents is discussed in light of recent data on the mechanism of action of vanilloids on sensory nerve fibers.

Synthesis and Liquid Crystalline Phases of Pyridazine Derivatives II

Four more pyridazine compounds were synthesized.The compounds have a general structure R-X-Y-Z-R'; where Y is 3,6 disubstituted pyridazine ring, X and Z are either trans cyclohexyl or phenyl rings, R and R' are n-alkyl groups.The structure assignments were confirmed by carbon 13 NMR.Their liquid crystalline properties were evaluated.When both X and Z are cyclohexyl rings, the compounds have a single smectic b phase.However, if a phenyl ring is introduced into the system, the morphology becomes complicated.Keywords: synthesis, pyridazine, smectic, classification