344-20-7

Usage

Chemical Properties

white to light yellow crystal powder

InChI:InChI=1/C6H3Br2FO/c7-4-1-3(9)2-5(8)6(4)10/h1-2,10H

Upstream product

• 371-41-5 4-Fluorophenol 
• 74-88-4 methyl iodide 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 371-40-4 4-fluoroaniline 

Downstream Products

• 319-50-6 (2,6-dibromo-4-fluoro-phenoxy)-acetic acid 
• 443-41-4 1,3-dibromo-5-fluoro-2-methoxybenzene 
• 117923-79-2 C₆⁽¹³⁾CH₅Br₂FO 
• 117923-66-7 2,6-dibromo-4-fluorphenyl phenyl ether 
• 398-23-2 4,4'-difluorobiphenyl 
• 131003-12-8 4',5-difluorobiphenyl-2-ol 
• 131003-10-6 3-Bromo-5,4'-difluoro-biphenyl-2-ol 
• 131003-11-7 4,5',4''-Trifluoro-[1,1';3',1'']terphenyl-2'-ol 
• 100-02-7 4-nitro-phenol 
• 19643-45-9 2,6-dibromo-1,4-benzoquinone 
• 320-75-2 2-bromo-4-fluoro-6-nitrophenol 
• 203922-16-1 1,3-dibromo-2-(2-chloroethoxy)-5-fluorobenzene 
• 203922-20-7 1-(2-chloroethoxy)-4-fluoro-3-aminobenzene 
• 203922-19-4 1-(2-Chloroethoxy)-2.6-dibromo-4-fluoro-3-nitrobenzene 

Relevant academic research and scientific papers

Method for photocatalytic synthesis of polybrominated phenol compound in water phase

The invention discloses a method for photocatalytic synthesis of a polybrominated phenol compound in a water phase, comprising the following steps: adding a catalytic amount of a radical initiator, aphenol derivative and low-toxic and cheap bromide salt and water into a reaction vessel, reacting at room temperature at 5 W power in a photocatalytic reactor for a certain period, extracting with ethyl acetate and then re-crystallizing to obtain a polybrominated phenol compound. The above radical initiator is eosin, azobisisobutanol, sodium persulfate, ammonium persulfate or potassium persulfate.The free radical initiator and the bromine salt are cheap and easily available, and the method is an ideal synthesis method of the polybrominated phenol compound. According to the method, low-toxicity bromine salt instead of liquid bromine is used to carry out a bromination reaction, unstable and explosive hydrogen peroxide is replaced with the cheap and easily-available free radical initiator, and an emerging photocatalytic method is used. The polybrominated phenol compound can be obtained in a high yield by only using a 5W power lamp for the reaction, the reaction selectivity is high, by-products are less, and the post-treatment is simple.

A quick, mild and efficient bromination using a CFBSA/KBr system

Bromination is a fundamental transformation in organic chemistry and brominated compounds as building blocks are of paramount importance in organic synthesis. In our study, we have developed an efficient method of bromination by using a CFBSA/KBr system at room temperature in a short reaction time. Notably, this approach has been proven to be applicable to a range of substrates including 1,3-diketones and β-keto esters, phenols, aromatic amines and heteroarenes with good to excellent yields.

Selective and efficient generation of ortho-brominated para-substituted phenols in ACS-grade methanol

The mono ortho-bromination of phenolic building blocks by NBS has been achieved in short reaction times (15-20 min) using ACS-grade methanol as a solvent. The reactions can be conducted on phenol, naphthol and biphenol substrates, giving yields of >86% on gram scale. Excellent selectivity for the desired mono ortho-brominated products is achieved in the presence of 10 mol % para-TsOH, and the reaction is shown to be tolerant of a range of substituents, including CH3/ F,and NHBoc.

Rapid and total bromination of aromatic compounds using TsNBr2 without any catalyst

N,N-Dibromo-p-toluenesulfonamide (TsNBr2) has been found to be a new reagent for bromination of aromatic compounds. The reaction is extremely fast and goes into completion instantaneously at ambient temperature to produce exclusively the corresponding polybrominated product. This procedure is applicable to various phenols, anisole, and anilines to give corresponding polybrominated compound as a single product in excellent yield.

COMPOUNDS AND METHODS OF USE THEREOF

Indole compounds are disclosed. Also disclosed are methods for using the compounds to treat human and animal disease, pharmaceutical compositions of the compounds, and kits including the compounds.

4-AMINOETHOXY INDOLONE DERIVATIVES

A compound of formula (I) in which Y is hydrogen, halogen or lower alkoxy; R1 is hydrogen, lower alkyl or aryl(lower)alkyl; R2 is hydrogen, lower alkyl or -(CH2)nXpAr, where X is oxygen or carbonyl; Ar is cycloalkyl, aryl or arylaryl, oxindolyl, benzimidazolyl, indolyl, 2-oxobenzimidazolyl or 2-thioxobenzimidazolyl; or R1 and R2, taken together with the nitrogen atom to which they are attached, complete a 3,4-dihydro-1H-isoquinolinyl or 1,3-dihydro-isoindolyl; n is one of the integers 1,2,3,4,5 or 6; p is one of the integers 0 or 1; or a pharmaceutically acceptable salt thereof are inhibitors of dopamine synthesis and release, useful in the treatment of schizophrenia, Parkinson's Disease, Tourette's Syndrome, alcohol addiction, cocaine addiction, and addiction to analogous drugs.

New generation dopaminergic agents. 6. Structure-activity relationship studies of a series of 4-(aminoethoxy)indole and 4-(aminoethoxy)indolone derivatives based on the newly discovered 3-hydroxyphenoxyethylamine D2 template

A series of 4-(aminoethoxy)indoles 7 and a related series of 4- (aminoethoxy)indolones 8 were synthesized and evaluated for their affinity for both the high- and low-affinity agonist states (D2(High) and D2(Low), respectively) of the dopamine (DA) D2 receptor. The 4-aminoethoxy derivatives (i.e., 7 and 8) were designed as bioisosteric analogues based on the phenol prototype 4. The indolones 8 were observed to have high affinity for the D2(High) receptor. Comparison of their previously reported chroman analogues with the more flexible 4-(aminoethoxy)indoles revealed the chroman analogues to be more potent, whereas little loss in D2(High) affinity was observed when comparing the 4-(aminoethoxy)indolones with their respective chroman analogues. Several regions of the phenoxyethylamine framework were modified and recognized as potential sites to modulate the level of intrinsic activity. A conformational analysis was performed and a putative bioactive conformation was proposed which fulfilled the D2 agonist pharmacophore criteria based on the McDermed model. Structure-activity relationships gained from these studies have aided in the synthesis of D2 partial agonists of varying intrinsic activity levels. These agents should be of therapeutic value in treating disorders resulting from hypo- and hyperdopaminergic activity, without the side effects associated with complete D2 agonism or antagonism.

New generation dopaminergic agents. 2. Discovery of 3-OH-phenoxyethylamine and 3-OH-N1-phenylpiperazine dopaminergic templates

Described in this report is a systematic study which led to the identification of two new dopamine D2 partial agonists (5 and 17). Phenols 5 and 17 represent prototypes of two new classes of D2 partial agonist as well as templates for the future design of novel dopaminergic agents.

4-AMINOETHOXY INDOLONE DERIVATIVES

A compound of the formula I: STR1 in which Y is hydrogen, halogen or lower alkoxy; R 1 is hydrogen, lower alkyl or aryl(lower) alkyl; R. sub.2 is hydrogen, lower alkyl or--(CH 2) n X p Ar, where X is oxygen or carbonyl; Ar is cycloalkyl, aryl or arylaryl, oxindolyl, benzimidazolyl, indolyl, 2-oxobenzimidazolyl or 2-thioxobenzimidazolyl; or R 1 and R 2, taken together with the nitrogen atom to which they are attached, complete a 3,4-dihydro-1H-isoquinolinyl or 1,3-dihydro-isoindolyl; n is one of the integers 1,2,3, 4,5 or 6; p is one of the integers 0 or 1; or a pharmaceutically acceptable salt thereof are inhibitors of dopamine synthesis and release, useful in the treatment of schizophrenia, Parkinson's Disease, Tourette's Syndrome, alcohol addiction, cocaine addiction, and addiction to analogous drugs.

Long-range 13C, 1H and 13C, 19F coupling constants as indicators of the conformational properties of 4-fluoroanisole, 2,3,5,6-tetrafluoroanisole, and pentafluoroanisole

Long-range spin-spin coupling constants over six bonds between 13C nuclei in the methyl group and ring protons or 19F nuclei in the para position are reported for 4-fluoroanisole, 2,3,5,6-tetrafluoroanisole, and pentafluoroanisole in solution.The couplings are ?-? electron mediated, as indicated by INDO MO FPT computations and by measurements on anisole, 2,6-dibromoanisole, 2,6-dichloroanisole, 2,6-dibromo-4-fluoroanisole, and 2,6-dibromo-4-methylanisole.On the basis of the measured coupling magnitudes and a hindered rotor model, it is concluded that the barrier to internal rotation about the Csp2-O bond in 4-fluoroanisole lies near 6 kcal/mol, is nearly zero in the tetrafluoroanisole, and is somewhat less than 1 kcal/mol in the pentafluoroanisole.In the latter, the preferred comformation is that in which the methoxy group lies in a plane perpendicular to the pentafluorophenyl plane.Some inconclusive dynamic nmr experiments on anisole, including T1p measurements, are briefly discussed.