21900-52-7

Basic information

• Product Name: 5-BROMO-2-CHLORO-BENZOYL CHLORIDE
• Synonyms: 5-BROMO-2-CHLORO-BENZOYL CHLORIDE;Benzoyl chloride, 5-bromo-2-chloro-
• CAS NO: 21900-52-7
• Molecular Formula: C₇H₃BrCl₂O
• Molecular Weight: 253.91
• Mol File: 21900-52-7.mol

Chemical Properties

• Boiling Point: 281.4°C at 760 mmHg
• Flash Point: 124°C
• Appearance: /
• Density: 1.763g/cm³
• Vapor Pressure: 0.00357mmHg at 25°C
• Refractive Index: 1.597
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 5-BROMO-2-CHLORO-BENZOYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-2-CHLORO-BENZOYL CHLORIDE(21900-52-7)
• EPA Substance Registry System: 5-BROMO-2-CHLORO-BENZOYL CHLORIDE(21900-52-7)

Safety Data

• Hazardous Substances Data: 21900-52-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-BROMO-2-CHLORO-BENZOYL CHLORIDE is used as an intermediate in the synthesis of dapagliflozin, a potent and selective hSGLT2 inhibitor. This application is significant because dapagliflozin is a widely used medication for the treatment of type 2 diabetes, helping to regulate blood sugar levels and improve overall glucose metabolism.
Additionally, 5-BROMO-2-CHLORO-BENZOYL CHLORIDE is also used as an intermediate in the synthesis of labelled and unlabelled isotopes of glucuronide metabolites of dapagliflozin. This application is important for research purposes, as it allows scientists to study the metabolic pathways and pharmacokinetics of dapagliflozin, leading to a better understanding of its mechanism of action and potential side effects.

InChI:InChI=1/C7H3BrCl2O/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3H

Upstream product

• 21739-92-4 5-bromo-2-chlorobenzoic acid 
• 54932-72-8 2-chloro-5-bromotoluene 
• 99-52-5 2-methyl-4-nitro-benzenamine 
• 79-37-8 oxalyl dichloride 
• 5781-53-3 monomethyl oxalyl chloride 
• 106-39-8 bromochlorobenzene 

Downstream Products

• 201686-71-7 6-[bis-(5-bromo-2-chloro-benzoyl)-amino]-nicotinic acid ethyl ester 
• 860638-84-2 1-(5-bromo-2-chlorophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-yn-1-one 
• 127767-42-4 2-(5-bromo-2-chloro-phenyl)-6-methyl-chromen-4-one 
• 842136-59-8 5-bromo-2-chloro-N-methoxy-N-methyl-benzamide 
• 898538-30-2 (5-bromo-2-chlorophenyl)(4-ethoxy-2,5-difluorophenyl)methanone 
• 301672-80-0 5-bromo-2-chloro-N-(tricyclo[3.3.1.1^3,7]dec-1-ylmethyl)benzamide 
• 860638-89-7 (S)-1-(2-bromophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-yn-1-ol 
• 860638-85-3 (S)-1-(5-bromo-2-chlorophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-yn-1-ol 
• 860638-90-0 (R)-5-(3-(2-bromophenyl)-3-(methoxymethoxy)propyl)-1,2,3-trimethoxybenzene 
• 860781-52-8 (S)-5-(3-(2-bromophenyl)-3-(methoxymethoxy)prop-1-ynyl)-1,2,3-trimethoxybenzene 
• 860638-86-4 (S)-5-(3-(5-bromo-2-chlorophenyl)-3-(methoxymethoxy)prop-1-ynyl)-1,2,3-trimethoxybenzene 
• 860638-87-5 (R)-5-(3-(5-bromo-2-chlorophenyl)-3-(methoxymethoxy)propyl)-1,2,3-trimethoxybenzene 
• 860638-83-1 (R)-methyl 4-chloro-3-(1-(methoxymethoxy)-3-(3,4,5-trimethoxyphenyl)propyl)benzoate 
• 435273-54-4 5-bromo-2-chloro-N-methylbenzamide 

Relevant articles and documents

Synthesis of empagliflozin, a novel and selective sodium-glucose co-transporter-2 inhibitor, labeled with carbon-14 and carbon-13

Empagliflozin, (2S,3R,4R,5S,6R)-2-[4-chloro-3-[[4-[(3S)-oxolan-3-yl]oxyphenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5- triol was recently approved by the FDA for the treatment of chronic type 2 diabetes mellitus. Herein, we report the synthesis of car

PREPARATION OF HIGHLY PURE AMORPHOUS DAPAGLIFLOZIN

A novel and improved process for the preparation of amorphous dapagliflozin is disclosed. The present invention further provides pharmaceutical compositions containing amorphous dapagliflozin, optionally in a combination with one or more other active substances and methods for making the same.

Synthetic method of empagliflozin

The invention provides a brand-new synthesis process of empagliflozin. According to the process, a boric acid ester is used for halogen removal, and specific reaction conditions are combined, so thatempagliflozin can be prepared with high yield and simplicity and convenience in operation. The synthesis method of empagliflozin has the advantages of mild reaction conditions, high total yield, few side reactions and convenience in operation, thereby being beneficial to industrial production and cost control.

Synthesis method of dapagliflozin intermediate 5-bromo-2-chloro-4 '-ethoxydiphenylmethane

The invention discloses a synthesis method of a dapagliflozin intermediate 5-bromo-2-chloro-4 '-ethoxydiphenylmethane. The method comprises the following steps: using 5-bromo-2-chlorobenzoic acid as araw material to be acylated by thionyl chloride, and then carrying out acylation reaction with 1-nitro-4-(phenoxymethyl) benzene, reducing, acetylating, hydrogenating and ethylating to obtain the dapagliflozin intermediate 5-bromo-2-chloro-4'-ethoxydiphenylmethane. The method can effectively avoid the acylation reaction ortho-position by-product so that the preparation of dapagliflozin is convenient for quality control, the reaction is mild, the yield is high and the method has an industrial application prospect.

Preparation method of 5-bromo-2-chloro-4'-ethoxybenzophenone

The invention discloses a preparation method of 5-bromo-2-chloro-4'-ethoxybenzophenone, and belongs to the technical field of medicine synthesis. The preparation method comprises the following steps:(1) carrying out direct reflux reaction on 5-bromo-2-chlorobenzoic acid and thionyl chloride in the absence of a solvent under the catalysis of DMF, and evaporating excessive thionyl chloride to obtain 5-bromo-2-chlorobenzoyl chloride after the reaction is finished; (2) adding dichloromethane into the material obtained in the step (1) for dissolving, directly adding silica gel loaded aluminum trichloride, performing reacting with phenethyl ether under a vacuum condition, performing filtering after the reaction is completed, washing the filtrate with a 5% sodium bicarbonate solution and water in sequence, performing evaporating to remove the solvent, and performing recrystallizing with a mixed solvent of ethanol and water to obtain 5-bromo-2-chloro-4'-ethoxybenzophenone. The method providedby the invention has the advantages of the small acid solvent generation amount, less difficult-to-treat wastewater, high product purity and yield, no generation of by-products, environmental protection, simple operation, and suitability for industrial production and popularization.

GLUCOPYRANOSE DERIVATIVES USEFUL AS SGLT2 INHIBITORS

The present invention is directed to glucopyranose derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by SGLT2 activity. More particularly, the compounds of the present invention are useful in the treatment of for example, Type II diabetes mellitus, Syndrome X, and complications and symptoms associated with said disorders.

GLUCOPYRANOSE DERIVATIVES USEFUL AS SGLT2 INHIBITORS

The present invention is directed to glucopyranose derivatives of formula (I), pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by SGLT2 activity. More particularly, the compounds of the present invention are useful in the treatment of for example, Type II diabetes mellitus, Syndrome X, and complications and symptoms associated with said disorders.

Synthetic method for preparing empagliflozin intermediate

The invention discloses a synthetic method for preparing an empagliflozin intermediate. The method comprises the following specific steps: 1) mixing a compound I with a solvent, preparing a compound II by using an acylation reagent, adding the compound II into a system of fluorobenzene and aluminum trichloride, carrying out a Friedel-Crafts reaction at room temperature, performing quenching with water, conducting liquid separation and washing successively, and concentrating an organic matter to obtain a compound III; 2) adding the compound III into a reaction kettle, adding a solvent, an alkali and a catalyst, then adding a compound IV, carrying out heating for a reaction, performing washing with water after the reaction, and conducting concentrating and crystallizing to obtain a solid compound V; and 3) adding the compound V into the reaction kettle, adding a solvent, an acid and a reducing agent, carrying out quenching with water after a reaction, conducting liquid separation and washing successively, concentrating an organic matter, and carrying out crystallizing to obtain a solid compound V. The method is simple and safe in process, high in product yield, easy in impurity control and suitable for industrial production.

Preparation method of 5-bromo-2-chloro-4 '-ethoxydiphenylmethane

The invention relates to a preparation method of 5-bromo-2-chloro-4 '-ethoxydiphenylmethane. The preparation method is characterized by comprising the following steps: step S1, preparation of 5-bromo-2-chlorobenzoyl chloride, step S2, preparation of 5-bromo-2-chloro-4'-ethoxybenzophenone, and step S3, preparation of 5-bromo-2-chloro-4 '-ethoxydiphenylmethane. The invention further discloses the 5-bromine-2-chloro-4 '-ethoxydiphenylmethane prepared according to the preparation method of the 5-bromine-2-chloro-4'-ethoxydiphenylmethane. The invention further discloses the 5-bromine-2-chloro-4 '-ethoxydiphenylmethane prepared according to the preparation method of the 5-bromine-2-chloro-4'-ethoxydiphenylmethane. According to the preparation method of the 5-bromo-2-chloro-4 '-ethoxydiphenylmethane, traditional preparation process conditions are optimized and innovated, the method effectively improves the product purity, the reaction conversion rate and the production efficiency, has no special requirements on reaction conditions and equipment, is suitable for industrial production, causes less pollution to the environment and effectively realizes good combination of economic benefits, social benefits and ecological benefits.

Preparation method of dapagliflozin impurity (by machine translation)

The invention relates to a preparation method of dagliflozin impurity 5 - bromo -2 - chloro -2 ' - ethoxy benzophenone, which is sequentially subjected to chlorination, esterification, rearrangement and alkylation reaction to obtain a target product. The