948553-14-8

Basic information

• Product Name: 4-(Bromomethyl)-3-(trifluoromethyl)-Benzoylchloride
• Synonyms: 4-Bromomethyl-3-trifluoromethylbenzoyl chloride
• CAS NO: 948553-14-8
• Molecular Formula: C₉H₅BrClF₃O
• Molecular Weight: 301.49
• Mol File: 948553-14-8.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 281.7 °C at 760 mmHg
• Flash Point: 124.1 °C
• Appearance: /
• Density: 1.685 g/cm³
• Vapor Pressure: 0.00352mmHg at 25°C
• Refractive Index: 1.517
• CAS DataBase Reference: 4-(Bromomethyl)-3-(trifluoromethyl)-Benzoylchloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(Bromomethyl)-3-(trifluoromethyl)-Benzoylchloride(948553-14-8)
• EPA Substance Registry System: 4-(Bromomethyl)-3-(trifluoromethyl)-Benzoylchloride(948553-14-8)

Safety Data

• Hazardous Substances Data: 948553-14-8(Hazardous Substances Data)

Usage

General Description

4-(Bromomethyl)-3-(trifluoromethyl)-Benzoylchloride is a chemical compound with the molecular formula C9H6BrF3OCl. It is a benzoyl chloride derivative that contains a bromomethyl group and a trifluoromethyl group. 4-(Bromomethyl)-3-(trifluoromethyl)-Benzoylchloride is used in organic synthesis as a versatile building block for the preparation of various pharmaceuticals, agrochemicals, and other fine chemicals. It is also used as a reagent for the introduction of the benzoyl chloride group into other molecules during chemical synthesis. 4-(Bromomethyl)-3-(trifluoromethyl)-Benzoylchloride is known for its high reactivity and is handled and used with care due to its potential hazards.

InChI:InChI=1/C9H5BrClF3O/c10-4-6-2-1-5(8(11)15)3-7(6)9(12,13)14/h1-3H,4H2

Upstream product

• 859213-39-1 4-(bromomethyl)-3-(trifluoromethyl)benzoic acid 
• 261952-01-6 4-methyl-3-(trifluoromethyl)benzoic acid 

Downstream Products

• 859213-40-4 4-(bromomethyl)-3-trifluoromethyl-N-{4-methyl-3-[4-(5-pyrimidinyl)pyrimidin-2-ylamino]phenyl}benzamide 
• 641614-88-2 4-(4-methylpiperazin-1-ylmethyl)-3-trifluoromethyl-N-{4-methyl-3-[4-(5-pyrimidinyl)pyrimidin-2-ylamino]phenyl}benzamide 
• 859217-05-3 4-[(R)-3-(dimethylamino)pyrrolidin-1-ylmethyl]-3-trifluoromethyl-N-{4-methyl-3-[4-(5-pyrimidinyl)pyrimidin-2-ylamino]phenyl}benzamide 
• 859217-05-3 Bafetinib 
• 1255702-10-3 N-(4-methyl-3-(3-(pyridin-3-yl)acrylamido)phenyl)-4-((4-methylpiperazin-1-yl)methyl)-3-(trifluoromethyl)benzamide 

Relevant articles and documents

Discovery of 4-methyl-N-(4-((4-methylpiperazin- 1-yl)methyl)-3-(trifluoromethyl)phenyl)-3-((6-(pyridin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-oxy)benzamide as a potent inhibitor of RET and its gatekeeper mutant

The receptor tyrosine kinase rearranged during transfection (RET) plays pivotal roles in several cancers, including thyroid carcinoma and non-small cell lung cancer (NSCLC). Currently, there are several FDA-approved RET inhibitors, but their indication is limited to thyroid cancer, and none can overcome their gatekeeper mutants (V804L and V804M). Here, we report the discovery of 9x representing a new chemotype of potent and selective RET inhibitors, using a rational design strategy of type II kinase inhibitors. 9x exhibited both superior antiproliferative activities against NSCLC-related carcinogenic fusions KIF5B-RET and CCDC6-RET and gatekeeper mutant-transformed Ba/F3 cells, with the lowest GI50 of 9 nM, and substantial inhibitory activities against wild-type RET and RET mutant proteins, with the best IC50 of 4 nM. More importantly, 9x also showed nanomole potency against RET-positive NSCLC cells LC-2/ad, but not against a panel of RET-negative cancer cells, such as A549, H3122, A375 or parental Ba/F3 cells, demonstrating its selective ‘on-target’ effect. In mouse xenograft models, 9x repressed tumor growth driven by both wild type KIF5B-RET-Ba/F3 and gatekeeper mutant KIF5B-RET(V804M)-Ba/F3 cells in a dose-dependent manner. Together, these data establish that 9x provides a good starting point for the development of targeted therapeutics against RET-positive cancers, especially NSCLC.

Design and synthesis of 3-substituted benzamide derivatives as Bcr-Abl kinase inhibitors

A series of 3-substituted benzamide derivatives structurally related to STI-571 (imatinib mesylate), a Bcr-Abl tyrosine kinase inhibitor used to treat chronic myeloid leukemia (CML), was prepared and evaluated for antiproliferative activity against the Bc