6282-88-8

Basic information

• Product Name: 3-(4-Chlorophenyl)propan-1-ol
• Synonyms: 3-(4-CHLOROPHENYL)PROPAN-1-OL;3-(4'-CHLOROPHENYL)PROPANOL;3-(4-CHLOROPHENYL)PROPANOL;3-(4-Chlorophenyl)propan-1-ol, 95+%;3-(4-Chlorophenyl)propanol 95%;Benzenepropanol, 4-chloro-;3-(4-Chlorophenyl)propanol95%
• CAS NO: 6282-88-8
• Molecular Formula: C₉H₁₁ClO
• Molecular Weight: 170.64
• Product Categories: Phenyls & Phenyl-Het;Phenyls & Phenyl-Het
• Mol File: 6282-88-8.mol

Chemical Properties

• Boiling Point: 104°C 0,1mm
• Flash Point: 117.5 °C
• Appearance: Colorless liquid
• Density: 1.151 g/cm³
• Vapor Pressure: 0.00331mmHg at 25°C
• Refractive Index: 1.545
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 15.03±0.10(Predicted)
• CAS DataBase Reference: 3-(4-Chlorophenyl)propan-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-Chlorophenyl)propan-1-ol(6282-88-8)
• EPA Substance Registry System: 3-(4-Chlorophenyl)propan-1-ol(6282-88-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-41
• Safety Statements: 26-36/37/39-24/25-39
• HazardClass: IRRITANT
• Hazardous Substances Data: 6282-88-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-(4-Chlorophenyl)propan-1-ol is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its ability to be modified and functionalized makes it a versatile building block for the development of new drugs.
Used in the Synthesis of Aldo-Keto Reductase Inhibitors:
Specifically, 3-(4-Chlorophenyl)propan-1-ol is utilized in the preparation of 2-Oxo-2H-chromene-3-carboxylic Acid Amide derivatives, which are known as Aldo-Keto reductase inhibitors. These inhibitors play a crucial role in the treatment of various diseases, including diabetes, by targeting and regulating the activity of Aldo-Keto reductases, a family of enzymes involved in sugar and lipid metabolism.

InChI:InChI=1/C9H11ClO/c10-9-5-3-8(4-6-9)2-1-7-11/h3-6,11H,1-2,7H2

Upstream product

• 7116-36-1 ethyl 3-(4-chlorophenyl)propanoate 
• 1073-67-2 4-vinylbenzyl chloride 
• 201230-82-2 carbon monoxide 
• 75-21-8 oxirane 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 64-17-5 ethanol 
• 50561-69-8 methyl 3-(4-chlorophenyl)propanoate 
• 2019-34-3 3-(4-chlorophenyl)propanoic acid 
• 104-88-1 4-chlorobenzaldehyde 
• 637-87-6 1-Chloro-4-iodobenzene 
• 107-18-6 allyl alcohol 
• 1615-02-7 p-chlorocinnamic acid 
• 24583-70-8 3-(4-chlorophenyl)-2-propene-1-ol 
• 6048-06-2 ethyl-p-chlorocinnamate 

Downstream Products

• 90562-26-8 3-(4-chlorophenyl)-1-iodopropane 
• 75677-02-0 3-(4-chlorophenyl)propionaldehyde 
• 61440-60-6 methanesulfonic acid 3-(4-chlorophenyl)-propyl ester 
• 64473-35-4 3-(4-chlorophenyl)propyl bromide 
• 78573-36-1 p-toluenesulphonic acid 3-(4-chlorophenyl)-propyl ester 
• 371111-50-1 ethyl-5-(4-chlorophenyl)pent-2-enoate 
• 371111-52-3 methyl [12S,9S]-(12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diazatricyclo[17.2.2.1^3,7]tetracosa-1⁽²²⁾,3⁽²⁴⁾,4,6,19⁽²³⁾,20-hexane-9-carboxylate) 
• 371111-53-4 [12S,9S]-(2-{3-[(12-cyclohexyl-11,14-dioxo-2-oxa-10,13-diazatricyclo[17.2.2.1^3,7]tetracosa-1⁽²²⁾,3⁽²⁴⁾,4,6,19⁽²³⁾,20-hexaene-9-carbonyl)amino]-2-hydroxyhexanoylamino}acetylamino)-[S]-phenylacetic acid tert-butyl ester 
• 371110-93-9 (S)-(2-{3-[((9S,12S)-12-Cyclohexyl-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[17.2.2.1^3,7]tetracosa-1⁽²²⁾,3,5,7⁽²⁴⁾,19⁽²³⁾,20-hexaene-9-carbonyl)-amino]-2-oxo-hexanoylamino}-acetylamino)-phenyl-acetic acid tert-butyl ester 
• 161725-12-8 5-(4-chlorophenyl)pentanoic acid 
• 371111-51-2 5-(4-chloro-phenyl)-pentanoic acid ethyl ester 
• 294863-03-9 1-[(R)-1-(tert-butyldimethylsilyloxy)-4-[6-(3-(4-chlorophenyl)propoxy)indol-1-yl]-2-butyl]imidazole-4-carboxamide 
• 294863-07-3 1-{(R)-1-(tert-butyldimethylsilyloxy)-4-[5-(3-(4-chlorophenyl)propoxy)-1-methylindol-3-yl]-2-butyl}imidazole-4-carboxamide 

Relevant articles and documents

Access to Trisubstituted Fluoroalkenes by Ruthenium-Catalyzed Cross-Metathesis

Although the olefin metathesis reaction is a well-known and powerful strategy to get alkenes, this reaction remained highly challenging with fluororalkenes, especially the Cross-Metathesis (CM) process. Our thought was to find an easy accessible, convenient, reactive and post-functionalizable source of fluoroalkene, that we found as the methyl 2-fluoroacrylate. We reported herein the efficient ruthenium-catalyzed CM reaction of various terminal and internal alkenes with methyl 2-fluoroacrylate giving access, for the first time, to trisubstituted fluoroalkenes stereoselectively. Unprecedent TON for CM involving fluoroalkene, up to 175, have been obtained and the reaction proved to be tolerant and effective with a large range of olefin partners giving fair to high yields in metathesis products. (Figure presented.).

Iridium-Catalyzed Domino Hydroformylation/Hydrogenation of Olefins to Alcohols: Synergy of Two Ligands

A novel one-pot iridium-catalyzed domino hydroxymethylation of olefins, which relies on using two different ligands at the same time, is reported. DFT computation reveals different activities for the individual hydroformylation and hydrogenation steps in the presence of mono- and bidentate ligands. Whereas bidentate ligands have higher hydrogenation activity, monodentate ligands show higher hydroformylation activity. Accordingly, a catalyst system is introduced that uses dual ligands in the whole domino process. Control experiments show that the overall selectivity is kinetically controlled. Both computation and experiment explain the function of the two optimized ligands during the domino process.

Radical Chain Reduction via Carbon Dioxide Radical Anion (CO2?-)

We developed an effective method for reductive radical formation that utilizes the radical anion of carbon dioxide (CO2?-) as a powerful single electron reductant. Through a polarity matched hydrogen atom transfer (HAT) between an electrophilic radical and a formate salt, CO2?- formation occurs as a key element in a new radical chain reaction. Here, radical chain initiation can be performed through photochemical or thermal means, and we illustrate the ability of this approach to accomplish reductive activation of a range of substrate classes. Specifically, we employed this strategy in the intermolecular hydroarylation of unactivated alkenes with (hetero)aryl chlorides/bromides, radical deamination of arylammonium salts, aliphatic ketyl radical formation, and sulfonamide cleavage. We show that the reactivity of CO2?- with electron-poor olefins results in either single electron reduction or alkene hydrocarboxylation, where substrate reduction potentials can be utilized to predict reaction outcome.

Ir-catalyzed tandem hydroformylation-transfer hydrogenation of olefins with (trans-/cis-)formic acid as hydrogen source in presence of 1,10-phenanthroline

The one-pot tandem hydroformylation-reduction to synthesize alcohols from olefins is in great demand but suffering from low yields, poor selectivity and harsh condition. Herein, 1,10-phenanthroline (L1) modified Ir-catalyst proved to exhibit multiple cata

Iridium Complex-Catalyzed C2-Extension of Primary Alcohols with Ethanol via a Hydrogen Autotransfer Reaction

The development of a C2-extension of primary alcohols with ethanol as the C2 source and catalysis by [Cp*IrCl2]2 (where Cp? = pentamethylcyclopentadiene) is described. This new extension system was used for a range of benzylic alcohol substrates and for aliphatic alcohols with ethanol as an alkyl reagent to generate the corresponding C2-extended linear alcohols. Mechanistic studies of the reaction by means of intermediates and deuterium labeling experiments suggest the reaction is based on hydrogen autotransfer.

Carbene-Catalyzed α-Carbon Amination of Chloroaldehydes for Enantioselective Access to Dihydroquinoxaline Derivatives

An NHC-catalyzed α-carbon amination of chloroaldehydes was developed. Cyclohexadiene-1,2-diimines are used as amination reagents and four-atom synthons. Our reaction affords optically enriched dihydroquinoxalines that are core structures in natural products and synthetic bioactive molecules.

Chemical modification-mediated optimisation of bronchodilatory activity of mepenzolate, a muscarinic receptor antagonist with anti-inflammatory activity

The treatment for patients with chronic obstructive pulmonary disease (COPD) usually involves a combination of anti-inflammatory and bronchodilatory drugs. We recently found that mepenzolate bromide (1) and its derivative, 3-(2-hydroxy-2, 2-diphenylacetoxy)-1-(3-phenoxypropyl)-1-azoniabicyclo[2.2.2]octane bromide (5), have both anti-inflammatory and bronchodilatory activities. We chemically modified 5 with a view to obtain derivatives with both anti-inflammatory and longer-lasting bronchodilatory activities. Among the synthesized compounds, (R)-(–)-12 ((R)-3-(2-hydroxy-2,2-diphenylacetoxy)-1-(3-phenylpropyl)-1-azoniabicyclo[2.2.2]octane bromide) showed the highest affinity in vitro for the human muscarinic M3 receptor (hM3R). Compared to 1 and 5, (R)-(–)-12 exhibited longer-lasting bronchodilatory activity and equivalent anti-inflammatory effect in mice. The long-term intratracheal administration of (R)-(–)-12 suppressed porcine pancreatic elastase-induced pulmonary emphysema in mice, whereas the same procedure with a long-acting muscarinic antagonist used clinically (tiotropium bromide) did not. These results suggest that (R)-(–)-12 might be therapeutically beneficial for use with COPD patients given the improved effects seen against both inflammatory pulmonary emphysema and airflow limitation in this animal model.

Highly pH-Dependent Chemoselective Transfer Hydrogenation of α,β-Unsaturated Aldehydes in Water

The pH-dependent selective Ir-catalyzed hydrogenation of α,β-unsaturated aldehydes was realized in water. Using HCOOH as the hydride donor at low pH, the unsaturated alcohol products were obtained exclusively, while the saturated alcohol products were formed preferentially by employing HCOONa as the hydride donor at high pH. A wide range of functional groups including electron-rich as well as electron-poor substituents on the aryl group of α,β-unsaturated aldehydes can be tolerated, affording the corresponding products in excellent yields with high TOF values. High selectivity and yields were also observed for α,β-unsaturated aldehydes with aliphatic substituents. Our mechanistic investigations indicate that the pH value is critical to the chemoselectivity.

Anodic benzylic C(sp3)-H amination: Unified access to pyrrolidines and piperidines

An electrochemical aliphatic C-H amination strategy was developed to access the important heterocyclic motifs of pyrrolidines and piperidines within a uniform reaction protocol. The mechanism of this unprecedented C-H amination strategy involves anodic C-H activation to generate a benzylic cation, which is efficiently trapped by a nitrogen nucleophile. The applicability of the process is demonstrated for 40 examples comprising both 5- and 6-membered ring formations.

Synthesis and fungicidal activity study of novel daphneolone analogs with 2,6-dimethylmorpholine

A series of novel daphneolone analogs was designed and synthesized on the basis of natural product 1,5-diphenyl-2-penten-1-one (I) from Stellera chamaejasme L. as lead compound, whereby 2,6-dimethylmorpholine moiety was introduced to replace 1-phenyl group. Their structures were confirmed by IR, 1H NMR, and HRMS (ESI) or elemental analysis, 13C NMR for some representative compounds. The two isomers of target compounds were separated and identified by NOESY technique and chemical method. All of the synthesized compounds have been evaluated for anti-plant pathogenic fungi activities. The results showed that some compounds exhibited moderate to good antifungal activities against tested fungi at the concentration of 50 mg/L. Among them, compound 7d, with a 4-bromine-substituted phenyl group and cis-2,6-dimethylmorpholine moiety, displayed best activity with an EC50 of 23.87 μmol/L against Valsa Mali, superior to lead compound I. In addition, preliminary structure-activity relationship analysis indicated that, between two isomers of target compounds, the antifungal activities of the isomer with cis-2,6-dimethylmorpholine were better than the trans-isomer.