1261606-45-4

Basic information

• Product Name: 4-Bromo-2-chlorobenzeneacetic Acid Ethyl Ester
• Synonyms: 4-Bromo-2-chlorobenzeneacetic Acid Ethyl Ester;Ethyl 2-(4-BroMo-2-chlorophenyl)acetate
• CAS NO: 1261606-45-4
• Molecular Formula: C₁₀H₁₀BrClO₂
• Molecular Weight: 277.5422
• Product Categories: Aromatics;Miscellaneous Reagents;Aromatics, Miscellaneous Reagents
• Mol File: 1261606-45-4.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• Solubility: Dichloromethane
• CAS DataBase Reference: 4-Bromo-2-chlorobenzeneacetic Acid Ethyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Bromo-2-chlorobenzeneacetic Acid Ethyl Ester(1261606-45-4)
• EPA Substance Registry System: 4-Bromo-2-chlorobenzeneacetic Acid Ethyl Ester(1261606-45-4)

Safety Data

• Hazardous Substances Data: 1261606-45-4(Hazardous Substances Data)

Usage

Chemical Properties

Colorless Semi-solid

Upstream product

• 67197-54-0 2-(4-bromo-2-chlorophenyl)acetonitrile 
• 64-17-5 ethanol 
• 14062-25-0 Ethyl 4-bromophenylacetate 
• 916516-89-7 2-(4-bromo-2-chlorophenyl)acetic acid 
• 59748-90-2 4-Bromo-2-chloro-benzoic Acid 
• 185315-48-4 (4-bromo-2-chlorophenyl)methanol 
• 89720-77-4 4-bromo-1-bromomethyl-2-chlorobenzene 
• 31928-47-9 4-bromo-2-chloroiodobenzene 
• 5764-82-9 bromo(2-ethoxy-2-oxoethyl)zinc 

Downstream Products

• 1428758-45-5 C₂₉H₂₉ClN₈O 
• 1330065-78-5 C₃₀H₃₀ClN₇OS 
• 1428760-83-1 3-chloro-4-(8-ethyl-2-(4-(4-methylpiperazin-1-yl)phenylamino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)benzonitrile 
• 1428759-01-6 C₂₇H₂₇ClN₁₀O 
• 1428760-84-2 3-chloro-4-(8-ethyl-2-(4-(4-methylpiperazin-1-yl)phenylamino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)-N-hydroxybenzimidamide 
• 1428760-85-3 3-chloro-4-[8-ethyl-2-(methylsulfanyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl]benzonitrile 
• 1428760-86-4 3-chloro-4-[8-ethyl-2-(methylsulfanyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl]-N'-hydroxy-1-benzenecarboximidamide 
• 1428760-87-5 6-[2-chloro-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-8-ethyl-2-(methylsulfanyl)pyrido[2,3-d]pyrimidin-7(8H)-one 
• 1428760-88-6 6-[2-chloro-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-8-ethyl-2-(methylsulfinyl)pyrido[2,3-d]pyrimidin-7(8H)-one 
• 1428759-09-4 6-[2-chloro-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-8-ethyl-2-[4-(4-methylpiperazino)anilino]pyrido[2,3-d]pyrimidin-7(8H)-one 
• 1428759-13-0 C₂₈H₂₆ClN₇O₂ 
• 1428760-89-7 6-(2-chloro-4-(2-methylthiazol-5-yl)phenyl)-8-ethyl-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one 
• 1428760-90-0 6-(2-chloro-4-(2-methyl-1,3-thiazol-5-yl)phenyl)-8-ethyl-2-(methylsulfinyl)pyrido[2,3-d]pyrimidin-7(8H)-one 
• 1428759-18-5 C₃₂H₃₃ClN₆OS 

Relevant articles and documents

Structure-Based Design of Selective Salt-Inducible Kinase Inhibitors

Salt-inducible kinases (SIKs) are key metabolic regulators. The imbalance in SIK function is associated with the development of diverse cancers, including breast, gastric, and ovarian cancers. Chemical tools to clarify the roles of SIK in different diseases are, however, sparse and are generally characterized by poor kinome-wide selectivity. Here, we have adapted the pyrido[2,3-d]pyrimidin-7-one-based p21-activated kinase (PAK) inhibitor G-5555 for the targeting of SIK, by exploiting differences in the back-pocket region of these kinases. Optimization was supported by high-resolution crystal structures of G-5555 bound to the known off-targets, MST3 and MST4, leading to a chemical probe, MRIA9, with dual SIK/PAK activity and excellent selectivity over other kinases. Furthermore, we show that MRIA9 sensitizes ovarian cancer cells to treatment with the mitotic agent paclitaxel, confirming earlier data from genetic knockdown studies and suggesting a combination therapy with SIK inhibitors and paclitaxel for the treatment of paclitaxel-resistant ovarian cancer.

Design of Selective PAK1 Inhibitor G-5555: Improving Properties by Employing an Unorthodox Low-pKa Polar Moiety

Signaling pathways intersecting with the p21-activated kinases (PAKs) play important roles in tumorigenesis and cancer progression. By recognizing that the limitations of FRAX1036 (1) were chiefly associated with the highly basic amine it contained, we devised a mitigation strategy to address several issues such as hERG activity. The 5-amino-1,3-dioxanyl moiety was identified as an effective means of reducing pKa and logP simultaneously. When positioned properly within the scaffold, this group conferred several benefits including potency, pharmacokinetics, and selectivity. Mouse xenograft PK/PD studies were carried out using an advanced compound, G-5555 (12), derived from this approach. These studies concluded that dose-dependent pathway modulation was achievable and paves the way for further in vivo investigations of PAK1 function in cancer and other diseases.

A chemoselective Reformatsky-Negishi approach to α-haloaryl esters

A practical synthesis of α-haloaryl esters has been achieved via a chemoselective Negishi coupling of poly-halogenated aromatics and Reformatsky reagents in the presence of catalytic Pd(dba)2 and Xantphos. This chemistry tolerates a variety of aryl halides and was successfully applied to the synthesis of Ibuprofen. The α-haloaryl ester products, exemplified by ethyl 2-(4-bromo-2-chlorophenyl)acetate (3a), can be further functionalized via palladium or copper catalysis to afford an array of α-aryl esters.