17847-51-7

Basic information

• Product Name: 3,4-DICHLOROPHENOL ACETATE
• Synonyms: 3,4-Dichlorophenyl acetate;Acetic acid, 3,4-dichlorophenyl ester
• CAS NO: 17847-51-7
• Molecular Formula: C₈H₆Cl₂O₂
• Molecular Weight: 205.03804
• Mol File: 17847-51-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,4-DICHLOROPHENOL ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DICHLOROPHENOL ACETATE(17847-51-7)
• EPA Substance Registry System: 3,4-DICHLOROPHENOL ACETATE(17847-51-7)

Safety Data

• Hazardous Substances Data: 17847-51-7(Hazardous Substances Data)

Upstream product

• 878-00-2 4-formylphenyl acetate 
• 45670-76-6 3,4-dichlorophenoxide ion 
• 1523-06-4 3-nitrophenyl acetate 
• 10186-94-4 3,4-dinitro-phenyl-acetate 
• 95-77-2 3,4-dichlorophenol 
• 830-03-5 4-nitrophenol acetate 
• 64-19-7 acetic acid 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 95-50-1 1,2-dichloro-benzene 
• 91-20-3 naphthalene 
• 33035-41-5 2-(diacetoxyiodo)mesitylene 

Downstream Products

• 22526-30-3 1-(4,5-dichloro-2-hydroxyphenyl)ethanone 
• 2466-76-4 N-Acetylimidazole 
• 95-77-2 3,4-dichlorophenol 
• 2164-37-6 6,7-dichloro-2-hydroxymethyl-1,4-benzodioxane 

Relevant articles and documents

Steric effect of NHC ligands in Pd(II)–NHC-catalyzed non-directed C–H acetoxylation of simple arenes

Although there has been a lot of progress in oxidative arene C–H functionalization reactions catalyzed by Pd(II/IV) system, the non-directed, site-selective functionalization of arene molecules is still challenging. It has been established that ligands play a pivotal role in controlling rate- as well as selectivity-determining step in a catalytic cycle involving well-defined metal-ligand bonding. N-heterocyclic carbene (NHC) ligands have had a tremendous contribution in the recent extraordinary success of achieving high reactivity and excellent selectivity in many catalytic processes including cross-coupling and olefin-metathesis reactions. However, the immense potential of these NHC ligands in improving site-selectivity of non-directed catalytic C–H functionalization reactions of simple arenes is yet to be realized, where overriding the electronic bias on deciding selectivity is a burdensome task. The presented work demonstrated an initiative step in this regard. Herein, a series of well-defined discrete [Pd(NHCR′R)(py)I2] complexes with systematically varied degree of spatial congestion at the Pd centre, exerted through the R and R’ substituents on the NHC ligand, were explored in controlling the activity as well as the site-selectivity of non-directed acetoxylation of representative monosubstituted and disubstituted simple arenes (such as toluene, iodobenzene and bromobenzene, naphthalene and 1,2-dichlorobenzene). The resulting best yields were found to be 75% for toluene and 65% for bromobenzene with [Pd(NHCMePh)(py)I2], 75% for iodobenzene and 79% for naphthalene with [Pd(NHCMeMe)(py)I2], and 41% for 1,2-dichlorobenzene with [Pd(NHCCyCy)(py)I2]. Most importantly, with increasing the bulkiness of the NHC ligand in the complexes, the selectivity of the distal C-acetoxylated products in comparison to the proximal ones, was enhanced to a great extent in all cases. Considering the vast library of NHC ligands, this study underscores the future opportunity to develop more strategies to improve the activity and the crucial site-selectivity of C–H functionalization reactions in simple as well as complex organic molecules.

Ligand-Promoted Palladium-Catalyzed C?H Acetoxylation of Simple Arenes

The palladium-catalyzed C?H oxidation of simple arenes is an attractive strategy to obtain phenols, which have many applications in the fine chemicals industry. Although some advances have been made in this research area, low reactivity and selectivity are, in general, observed. This report describes a new catalytic system for the efficient C?H acetoxylation of simple arenes based on Pd(OAc)2 and a pyridinecarboxylic acid ligand.

3-(Benzodioxan-2-ylmethoxy)-2,6-difluorobenzamides bearing hydrophobic substituents at the 7-position of the benzodioxane nucleus potently inhibit methicillin-resistant Sa and Mtb cell division

Lipophilic substituents at benzodioxane C (7) of 3-(benzodioxan-2-ylmethoxy)-2,6-difluorobenzamide improve the antibacterial activity against methicillin-resistant Staphylococcus aureus strains to MIC values in the range of 0.2-2.5 μg/mL, whereas hydrophi

Steric control of site selectivity in the Pd-catalyzed C-H acetoxylation of simple arenes

This report describes the use of an oxidant and a ligand to control site selectivity in the Pd(OAc)2-catalyzed C-H acetoxylation of simple arenes. The use of MesI(OAc)2 as the terminal oxidant in combination with acridine as the ligand results in primarily sterically controlled selectivity. In contrast, with Pd(OAc)2 as the catalyst and PhI(OAc)2 as the oxidant, electronic effects dominate the selectivity of arene C-H acetoxylation.

Remarkably high reactivity of Pd(OAc)2/pyridine catalysts: Nondirected C-H oxygenation of arenes

Less is more: The rational optimization and general applicability of the catalytic system Pd(OAc)2/pyridine is described (see scheme). The catalyst shows excellent reactivity in the C-H oxygenation of simple aromatic substrates. The Pd/pyridine ratio is critical as the use of one equivalent of pyridine per Pd center leads to dramatic enhancements in both reactivity and site selectivity in comparison to Pd(OAc)2 alone.

Platinum and palladium complexes containing cationic ligands as catalysts for arene H/D exchange and oxidation

Cationic catalysts in HD: Palladium(II) and platinum(II) complexes of pyridinium-substituted bipyridine ligands are highly active and stable catalysts for H/D exchange and oxidation of aromatic C-H bonds (TONs up to 3200, TOFs up to 0.1 s-1; se

SPIROKETONE ACETYL-COA CARBOXYLASE INHIBITORS

The invention provides compounds of Formula (1) or a pharmaceutically acceptable salt of said compound, wherein R1, R2, R3, R4, R5, R6, R7, R8 and R9 are as described herein; pharmaceutical compositions thereof; and the use thereof in treating mammals suffering from the condition of being overweight.

Optimization of chromone-2-carboxamide melanin concentrating hormone receptor 1 antagonists: Assessment of potency, efficacy, and cardiovascular safety

Evaluation of multiple structurally distinct series of melanin concentrating hormone receptor 1 antagonists in an anesthetized rat cardiovascualar assay led to the identification of a chromone-2-carboxamide series as having excellent safety against the chosen cardiovascular endpoints at high drug concentrations in the plasma and brain. Optimization of this series led to considerable improvements in affinity, functional potency, and pharmacokinetic profile. This led to the identification of a 7-fluorochromone-2-carboxamide (22) that was orally efficacious in a diet-induced obese mouse model, retained a favorable cardiovascular profile in rat, and demonstrated dramatic improvement in effects on mean arterial pressure in our dog cardiovascular model compared to other series reported by our group. However, this analogue also led to prolongation of the QT interval in the dog that was linked to affinity for hERG channel and unexpectedly potent functional blockade of this ion channel.

Sulfonamide-substituted chromans, processes for their preparation, their use as a medicament or diagnostic, and medicament comprising them

Sulfonamide-substituted chromans, processes for their preparation, their use as a medicament or a diagnostic, and medicament comprising them Chromans of the formula I and of the formula 1a having the meanings R(A), R(B), R(C) and R(1) to R(8) indicated in the claims are outstandingly suitable for preparing a medicament for blocking the K+channel which is opened by cyclic adenosine monophosphate (cAMP); and further for preparing a medicament for inhibiting gastric acid secretion; for the treatment of ulcers of the stomach and of the intestinal region, in particular of the duodenum, for the treatment of reflux esophagitis, for the treatment of diarrheal illnesses, for the treatment and prevention of all types of arrhythmias including ventricular and supraventricular arrhythmias, and for the control of reentry arrhythmias and for the prevention of sudden heart death as a result of ventricular fibrillation.

Structure-reactivity correlations for reactions of substituted phenolate anions with acetate and formate esters

The reactions of substituted phenolate anions with m-nitrophenyl, p-nitrophenyl, and 3,4-dinitrophenyl formates follow nonlinear Br?nsted-type correlations that might be taken as evidence for a change in the rate-limiting step of a reaction that proceeds through a tetrahedral addition intermediate. However, the correlation actually represents two different Br?nsted lines that are defined by meta- and para-substituted phenolate anions and by meta- and para-substituted o-chlorophenolate anions. A concerted mechanism for both acetyl- and formyl-transfer reactions is supported by the absence of a detectable change in the Br?nsted slope at ΔpK = 0 for the attacking and leaving phenolate anions within each class of Br?nsted correlations. Regular increases in the dependence of log k on the pKa of the nucleophile with increasing pKa of the leaving group correspond to a positive interaction coefficient pxy = ?β1g/?(pKnuc) = ?βnuc/?(pK1g). The observation of two different Br?nsted lines for the reactions of substituted phenolate anions with phenyl acetates is attributed to a steric effect that decreases the rate of reaction of substituted o-chlorophenolate anions by 25-50%. The reactions of meta- and para-substituted phenolate and o-chlorophenolate anions with substituted phenyl acetate esters follow values of βnuc = 0.53-0.66 and -β1g = 0.50-0.63. The reactions of meta- and para-substituted phenolate anions with formate esters are ～ 103 times faster and follow smaller values of βnuc = 0.43-0.64 and -β1g = 0.31-0.48. However, the reactions of meta- and para-substituted o-chlorophenolate anions with the same formate esters follow larger values of βnuc = 0.63-0.90 and -β1g = 0.46-0.90. The large values of βnuc and -β1g for the reactions of substituted o-chlorophenolate anions with formate esters may arise from destabilization by the o-chloro group of a stacking interaction that is present in the transition state for reactions of formate esters, but not acetate esters.