141109-25-3

Basic information

• Product Name: alpha-Bromo-2-chlorophenylacetic acid
• Synonyms: ALPHA-BROMO-2-CHLOROPHENYLACETIC ACID;A-BROMO 2-CHLOROPHENYLACETIC ACID;2-Bromo-2?Chlorophenylacetic Acid;-Bromo-2-Chlorophenylacetic Acid;alpha-2-(Chlorophenyl)acetic acid;α-Bromo-O-Chlorophenylacetic Acid;Alapha-bromo-(2-chloro)-phenylacetic acid;α-Bromo-2-(2-chlorophenyl)acetic acid
• CAS NO: 141109-25-3
• Molecular Formula: C8H6BrClO2
• Molecular Weight: 249.49
• EINECS: 1312995-182-4
• Product Categories: Aromatic Phenylacetic Acids and Derivatives;INTERMEDIATESOFCLOPIDOGREL
• Mol File: 141109-25-3.mol

Chemical Properties

• Melting Point: 108-110°C
• Boiling Point: 316.7 ºC at 760 mmHg
• Flash Point: 145.3 ºC
• Appearance: White crystal
• Density: 1.747 g/cm³
• Vapor Pressure: 0.00017mmHg at 25°C
• Refractive Index: 1.617
• CAS DataBase Reference: alpha-Bromo-2-chlorophenylacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: alpha-Bromo-2-chlorophenylacetic acid(141109-25-3)
• EPA Substance Registry System: alpha-Bromo-2-chlorophenylacetic acid(141109-25-3)

Safety Data

• Hazardous Substances Data: 141109-25-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Alpha-Bromo-2-chlorophenylacetic acid is used as a reagent in various organic synthesis procedures for its potential reactivity due to the presence of halogen atoms.
Used in Chemical Research:
Alpha-Bromo-2-chlorophenylacetic acid is used as a research compound in the field of chemistry, contributing to the understanding of halogenated compounds and their applications.
Used in Pharmaceutical Industry:
Alpha-Bromo-2-chlorophenylacetic acid is used as an intermediate in the synthesis of certain pharmaceutical compounds, given its reactivity and potential for chemical modification.
Used in Chemical Manufacturing:
Alpha-Bromo-2-chlorophenylacetic acid is used as a raw material in the production of various chemical products, taking advantage of its reactivity and functional groups.
Note: It is important to handle alpha-Bromo-2-chlorophenylacetic acid properly to avoid harmful effects, as it can cause skin irritation, serious eye damage, and may be harmful if inhaled or swallowed.

InChI:InChI=1/C8H6BrClO2/c9-7(8(11)12)5-3-1-2-4-6(5)10/h1-4,7H,(H,11,12)

Upstream product

• 10421-85-9 2-chloromandelic acid 
• 75-25-2 Bromoform 
• 108-20-3 di-isopropyl ether 
• 89-98-5 2-chloro-benzaldehyde 
• 29270-30-2 α-bromo-2-chlorophenyl acetic acid 
• 2856-79-3 ethyl α-bromo-2-chlorophenylacetate 
• 85259-19-4 methyl 2-bromo-2-(2-chlorophenyl)acetate 
• 86169-24-6 2-amino-(2-chlorophenyl)ethanoic acid 
• 2444-36-2 2'-chloro-benzeneacetic acid 

Downstream Products

• 4718-69-8 α--2-chlor-phenylessigsaeure 
• 133192-64-0 4-chloro-benzaldehyde [5-(2-chloro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone 
• 133192-66-2 2-chloro-benzaldehyde [5-(2-chloro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone 
• 133192-62-8 benzaldehyde [5-(2-chloro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone 
• 108897-02-5 4-methoxy-benzaldehyde [5-(2-chloro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone 
• 132465-89-5 2,4-dichloro-benzaldehyde [5-(2-chloro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone 
• 108897-90-1 2-methyl-benzaldehyde [5-(2-chloro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone 
• 108897-94-5 2-methoxy-benzaldehyde [5-(2-chloro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone 
• 133296-82-9 4-dimethylamino-benzaldehyde [5-(2-chloro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone 
• 133296-84-1 5-chloro-2-hydroxy-benzaldehyde [5-(2-chloro-phenyl)-4-oxo-thiazolidin-2-ylidene]-hydrazone 
• 1092477-55-8 (+/-)-N'-[3,5-bis(trifluoromethyl)phenyl]-2-(2-chlorophenyl)-2-(1-piperazinyl)acetohydrazide 
• 1092476-46-4 (+/-)-2-(2-chlorophenyl)-N'-(3,5-dichlorophenyl)-2-(4-methyl-1-piperazinyl)acetohydrazide 

Relevant articles and documents

Synthesis and Antibacterial Screening of 1,3,4-Thiadiazoles, 1,2,4-Triazoles, and 1,3,4-Oxadiazoles Containing Piperazine Nucleus

A series of novel 1,3,4-thiadiazoles, 1,2,4-triazoles, and 1,3,4-oxadiazoles were synthesized by cyclization of substituted 1-(2-(2-chlorophenyl)-2-(4-(2,3-dichlorophenyl)piperazin-1-yl)acetyl)thiosemicarbazide. The structures of all newly synthesized compounds were elucidated on the basis of spectral studies. Some of them were screened for their antibacterial activity. The compounds 6b, 6c, 8e, 9a, and 9b have shown moderate activity towards Bacillus Subtilis and Escherichia Coli.

Method for preparing clopidogrel intermediate alpha-bromo (2-chloro) methyl phenylacetate by recycling aqueous solution method

The invention provides a method for preparing clopidogrel intermediate alpha-bromo (2-chloro) methyl phenylacetate by recycling an aqueous solution method. According to the method, o-chlorophenylacetic acid is adopted as a main raw material, an organic solvent and water in an appropriate proportion are optimized to serve as a bromination mixed solvent, a two-phase reaction mode is adopted in the reaction process, a bromine-containing wastewater solution can be reused without complex treatment, a target product is prepared through bromination and esterification reactions, and the yield reaches78% or above; the method provided by the invention is based on a technical scheme of recycling an aqueous solution containing a bromination reagent. In the process production process, the input amountof a new bromination reagent is reduced to a great extent, the bromine atom utilization rate of the bromination reagent is increased, the problems of wastewater treatment and discharge are reduced, the pressure of environmental pollution is reduced, meanwhile, the reaction conditions are relatively mild, treatment is simple, and industrial production is facilitated.

Benzoxazinone-containing 3,5-dimethylisoxazole derivatives as BET bromodomain inhibitors for treatment of castration-resistant prostate cancer

The bromodomain and extra-terminal proteins (BET) have emerged as promising therapeutic targets for the treatment of castration-resistant prostate cancer (CRPC). We report the design, synthesis and evaluation of a new series of benzoxazinone-containing 3,5-dimethylisoxazole derivatives as selective BET inhibitors. One of the new compounds, (R)-12 (Y02234), binds to BRD4(1) with a Kd value of 110 nM and blocks bromodomain and acetyl lysine interactions with an IC50 value of 100 nM. It also exhibits selectivity for BET over non-BET bromodomain proteins and demonstrates reasonable anti-proliferation and colony formation inhibition effect in prostate cancer cell lines such as 22Rv1 and C4-2B. The BRD4 inhibitor (R)-12 also significantly suppresses the expression of ERG, Myc and AR target gene PSA at the mRNA level in prostate cancer cells. Treatment with (R)-12 significantly suppresses the tumor growth of prostate cancer (TGI = 70%) in a 22Rv1-derived xenograft model. These data suggest that compound (R)-12 is a promising lead compound for the development of a new class of therapeutics for the treatment of CRPC.

Clopidogre and wherein the intermediate α-bromo-ortho-chlorophenyl acetic acid and α-thiophene substituted ethylamino- method for the preparation of acetic acid hydrochloride (by machine translation)

The invention discloses a preparation method of clopidogrel and intermediates thereof. The preparation method of the clopidogrel and intermediates thereof, provided by the invention, has the characteristics of being simple to operate, mild in reaction condition, little in pollution, low in energy consumption and the like and is suitable for industrial production, a high-purity intermediate can be provided for production of the clopidogrel, and the production cost of the clopidogrel is reduced.

Synthesis of dendrimer-type chiral stationary phases based on the selector of (1S,2R)-(+)-2-amino-1,2-diphenylethanol derivate and their enantioseparation evaluation by HPLC

In our recent work, a series of dendritic chiral stationary phases (CSPs) were synthesized, in which the chiral selector was L-2-(p-toluenesulfonamido)-3- phenylpropionyl chloride (selector I), and the CSP derived from three-generation dendrimer showed the best separation ability. To further investigate the influence of the structures of dendrimer and chiral selector on enantioseparation ability, in this work, another series CSPs (CSPs 1-4) were prepared by immobilizing (1S,2R)-1,2-diphenyl-2-(3-phenylureido)ethyl 4-isocyanatophenylcarbamate (selector II) on one- to four-generation dendrimers that were prepared in previous work. CSPs 1 and 4 demonstrated the equivalent enantioseparation ability. CSPs 2 and 3 showed the best and poorest enantioseparation ability respectively. Basically, these two series of CSPs exhibited the equivalent enantioseparation ability although the chiral selectors were different. Considering the enantioseparation ability of the CSP derived from aminated silica gel and selector II is much better than that of the one derived from aminated silica gel and selector I, it is believed that the dendrimer conformation essentially impacts enantioseparation.

BENZOFUROPYRIMIDINONES AS PROTEIN KINASE INHIBITORS

A compound according to formula I: or a pharmaceutically acceptable salt thereof; wherein R1, R2, R3a, R3b, R3c and R3d are as defined in the specification, pharmaceutical compositions thereof, and methods of use thereof.

N-PHENYL HYDRAZIDES AS MODULATORS OF THE GHRELIN RECEPTOR

The present invention relates to novel compounds of formula (I) or a pharmaceutically acceptable salt or solvate thereof, wherein: each R1 is independently selected from the group consisting of Cl, Br, CH3 and CF3; X is carbon or nitrogen; R1a is H or a straight C1-3 alkyl group; R2a is H or a methyl group R2 is selected from the group consisting of C1-3alkyl, H and -(CH2)n-, wherein n is 3 or 4 and the terminal carbon of the chain is bonded to the carbon atom adjacent to the nitrogen bearing the R2 group, such that a fused 6,5 or 6,6-bicyclic ring is formed. Y is selected from the group consisting of: phenyl which may be unsubstituted or substituted by one or more substituents independently selected from the group consisting of C1-3alkyl, C1-3alkoxy, halogen, C1-3alkyl substituted by 1 to 7 fluoro atoms and C1-3alkoxy substituted by 1 to 7 fluoro atoms; pyridyl which may be unsubstituted or substituted by one or more substituents independently selected from the group consisting of C1-3alkyl, OCH3, CF3, CN, and halogen; naphthyl which may be unsubstituted or substituted by one or more substituents independently selected from the group consisting of F and OCH3; pyrimidinyl; imidazo[1,2-a]pyridine-6-yl; benzothiophen-2-yl; benzothiophen-5-yl; benzofuran-2-yl; dibenzo[b,d]furan-3-yl; dibenzo[b,d]thiophen-2-yl; dibenzo[b,d]thiophen-4-yl; 1,3- benzodioxol-5-yl; 2,3-dihydro-1,4-benzodioxin-5-yl; 2,3-dihydro-1,4-benzodioxin-6-yl; 2,3- dihydro-1-benzofuran-4-yl; 2,2-difluoro-1,3-benzodiox-4-yl; pyridazinyl; imidazolyl; oxazolyl; pyrazolyl; thiazolyl; and triazolyl; with the proviso that when Y is 2,3-dihydro-1,4-benzodioxin-6-yl, R1 is not Cl; processes for their preparation, intermediates useble in these processes, pharmaceutical compositions containing them and their use in therapy, for example as modulators of of the growth hormone secretagogue receptor (also referred to as the ghrelin receptor or GHSR1a receptor) and/or for the treatment and/or prophylaxis of a disorder mediated by the ghrelin receptor.

Design and synthesis of non-cytotoxic tetrahydrothieno[3,2-c]pyridine derivatives exhibiting complement inhibition activity

A series of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine derivatives have been synthesized and evaluated for their activity on the activation of human complement (classical pathway) and their intrinsic haemolytic activity. The in vitro assay results of these analogues for inhibition of complement activity reveals improved inhibitory activity for some of the analogues over existing tetrahydrothienopyridine derivatives like Ticlopidine and Clopidogrel. Significantly, these analogues did not exhibit any haemolytic activity and are non-cytotoxic to human cell lines.

THE METHOD OF MAKING OPTICALLY ACTIVE 2-HALO-2-(N-SUBSTITUTED PHENYL)ACETIC ACID ESTERS AND 2-HALO-2-(N-SUBSTITUTED PHENYL)ACETIC ACIDS BY ENZYMATIC METHOD

The present invention relates to the process for the preparation of optically active 2-halo-2-(n-substituted phenyl)acetic acid esters and optically active 2-halo-2-(n-substituted phenyl)acetic acids, which are used intensively as important chiral intermediates, represented by general formula 2 and 3 respectively from racemic 2-halo-2-(n-substituted phenyl)acetic acid ester represented by general formula 1. In more detail, this invention relates to the process for preparing optically active 2-halo-2-(n-substituted phenyl)acetic acid esters and optically active 2-halo-2-(n-substituted phenyl)acetic acids by stereospecific hydrolysis of racemic 2-halo-2-(n-substituted phenyl)acetic acid esters using hydrolases or hydrolase-producing microorganisms in the aqueous phase or organic phase including aqueous solvent. This method is useful in the practical process because the production and separation of compounds with high optical purity is easier.

Copper(II)-mediated resolution of α-halo carboxylic acids with chiral O,O′-dibenzoyltartaric acid: Spontaneous racemization and crystallization-induced dynamic resolution

Herein we present a new example of coordination-mediated resolution of racemic acids by a chiral acid. The reaction of copper(II) acetate monohydrate, optically pure O,O′-dibenzoyltartaric acid (DBTA) and racemic α-bromo-2-chlorophenylacetic acid (HL