1504-59-2

Basic information

• Product Name: 3-(2,4-Dichlorophenyl)-2-propen-1-ol
• Synonyms: 3-(2,4-Dichlorophenyl)-2-propen-1-ol;2-Propen-1-ol, 3-(2,4-dichlorophenyl)-
• CAS NO: 1504-59-2
• Molecular Formula: C₉H₈Cl₂O
• Molecular Weight: 203.06522
• Mol File: 1504-59-2.mol

Chemical Properties

• Boiling Point: 339.255°C at 760 mmHg
• Flash Point: 133.736°C
• Appearance: /
• Density: 1.338g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.622
• CAS DataBase Reference: 3-(2,4-Dichlorophenyl)-2-propen-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(2,4-Dichlorophenyl)-2-propen-1-ol(1504-59-2)
• EPA Substance Registry System: 3-(2,4-Dichlorophenyl)-2-propen-1-ol(1504-59-2)

Safety Data

• Hazardous Substances Data: 1504-59-2(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H8Cl2O/c10-8-4-3-7(2-1-5-12)9(11)6-8/h1-4,6,12H,5H2/b2-1+

Upstream product

• 1504-68-3 ethyl 2,4-dichlorocinnamate 
• 20595-45-3 2,4-dichlorocinnamic acid 
• 42174-01-6 methyl 2,4-dichlorocinnamate 
• 874-42-0 2,4-dichlorobenzaldeyhde 

Downstream Products

• 25084-61-1 Dimethyl-carbamic acid (E)-3-(2,4-dichloro-phenyl)-allyl ester 
• 146882-07-7 3-(2,4-dichlorophenyl)propan-1-ol 
• 1359132-03-8 1-(3-bromoprop-1-enyl)-2,4-dichlorobenzene 
• 1027496-33-8 3-Cyano-4-[3-(2,4-dichloro-phenyl)-propylsulfanyl]-3-hydroxy-butyric acid methyl ester 
• 1026639-62-2 4-[3-(2,4-Dichloro-phenyl)-propylsulfanyl]-3-oxo-butyric acid methyl ester 
• 1026334-46-2 Thioacetic acid S-[3-(2,4-dichloro-phenyl)-propyl] ester 
• 93962-66-4 1-(3-Bromo-propyl)-2,4-dichloro-benzene 
• 25084-62-2 Methyl-carbamic acid (E)-3-(2,4-dichloro-phenyl)-allyl ester 
• 77975-44-1 2,4-dichloro-1-(3-chloro-1-propenyl)-benzene 

Relevant articles and documents

Boron-Catalyzed C?C Functionalization of Allyl Alcohols

Tris(pentafluorophenyl)borane-catalyzed C?C bond functionalization of arylallyl alcohols using donor-acceptor carbenes is presented. The allylic hydroxyl group is found to assist the product formation by neighboring group participation providing a clue towards mechanistic understanding. This method can also be employed to effect homologation of allyl alcohols to homoallyl alcohols. Overall, this metal-free transformation presents a novel disconnection strategy towards carbon-carbon bond scission and formation. (Figure presented.).

Gold-Catalyzed [2,3]-Sigmatropic Rearrangement: Reaction of Aryl Allyl Alcohols with Diazo Compounds

A gold-catalyzed [2,3]-sigmatropic rearrangement reaction has been developed. The intermolecular rearrangement occurs between in situ generated donor-acceptor gold-carbenes and cinnamyl alcohols via tandem oxonium ylide formation. The desired rearranged product has been accomplished selectively over more conventional O-H insertion, cyclopropanation, cycloaddition, and C-H functionalization products under mild, open-air conditions. The scope of the work has been illustrated by synthesizing a new class of substrates that can be used for constructing complex molecular targets.

Discovery of Potent Benzofuran-Derived Diapophytoene Desaturase (CrtN) Inhibitors with Enhanced Oral Bioavailability for the Treatment of Methicillin-Resistant Staphylococcus aureus (MRSA) Infections

Blocking the staphyloxanthin biosynthesis process has emerged as a new promising antivirulence strategy. Previously, we first revealed that CrtN is a druggable target against infections caused by pigmented Staphylococcus aureus (S. aureus) and that naftifine was an effective CrtN inhibitor. Here, we identify a new type of benzofuran-derived CrtN inhibitor with submicromolar IC50 values that is based on the naftifine scaffold. The most potent analog, 5m, inhibits the pigment production of S. aureus Newman and three MRSA strains, with IC50 values of 0.38-5.45 nM, without any impact on the survival of four strains (up to 200 μM). Notably, compound 5m (1 μM) could significantly sensitize four strains to immune clearance and could effectively attenuate the virulence of three strains in vivo. Moreover, 5m was determined to be a weak antifungal reagent (MIC > 16 μg/mL). Combined with good oral bioavailability (F = 42.2%) and excellent safety profiles, these data demonstrate that 5m may be a good candidate for the treatment of MRSA infections.

ATP-citrate lyase as a target for hypolipidemic intervention. Design and synthesis of 2-substituted butanedioic acids as novel, potent inhibitors of the enzyme

ATP-citrate lyase is the primary enzyme responsible for the synthesis of cytosolic acetyl-CoA in many tissues. Inhibitors of the enzyme represent a potentially novel class of hypolipidemic agent, which are anticipated to have combined hypocholesterolemic and hypotriglyceridemic properties. A series of 2-substituted butanedioic acids have been designed and synthesized as inhibitors of the enzyme. The best compounds, 58, 68, 71, 74 have reversible K(i)'s in the 1-3 μM range against the isolated rat enzyme. As representative of this compound class, 58, has been shown to exert its inhibitory action through a mainly competitive mechanism with respect to citrate and a noncompetitive one with respect to CoA. None of the inhibitors were able to inhibit cholesterol and/or fatty acid synthesis in HepG2 cells. This has been attributed to the adverse physicochemical properties of the molecules leading to a lack of cell penetration. Despite this, a lead structural class of compound has been identified with the potential for modification into potent, cell-penetrant, and efficacious inhibitors of ATP- citrate lyase.