2417-72-3

Basic information

• Product Name: Methyl 4-(bromomethyl)benzoate
• Synonyms: Methyl 4-broMoMethylbenzoato;Methyl 4-(broMoMethyl)benzoate 98%;4 - broMine Methyl benzoic acid Methyl ester;p-(Methoxycarbonyl)benzyl bromide;4-(BROMOMETHYL)BENZOIC ACID METHYL ESTER;ALPHA-BROMO-P-TOLUIC ACID METHYL ESTER;METHYL P-(BROMOMETHYL)BENZOATE;METHYL 4-(BROMOMETHYL)BENZOATE
• CAS NO: 2417-72-3
• Molecular Formula: C₉H₉BrO₂
• Molecular Weight: 229.07
• EINECS: -0
• Product Categories: alkyl bromide| carboxylic ester;Pyrazoles;Chemical intermediate for Eprosartan;Aromatic Esters;Methyl Halides;Phenyls & Phenyl-Het;Methyl Halides;Phenyls & Phenyl-Het;C8 to C9;Carbonyl Compounds;Esters;Building Blocks;C8 to C9;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 2417-72-3.mol
• Article Data: 96

Chemical Properties

• Melting Point: 57-58 °C(lit.)
• Boiling Point: 130-135 °C2 mm Hg(lit.)
• Flash Point: 130-135°C/2mm
• Appearance: White to yellow/Crystalline Powder, Crystals and/or Chunks
• Density: 1,47 g/cm3
• Vapor Pressure: 0.00063mmHg at 25°C
• Refractive Index: 1.5320 (estimate)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility: Lowly soluble in water, highly soluble in ethanol and ether, not soluble in halogenated organic solvents
• Sensitive: Lachrymatory
• BRN: 1867272
• CAS DataBase Reference: Methyl 4-(bromomethyl)benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 4-(bromomethyl)benzoate(2417-72-3)
• EPA Substance Registry System: Methyl 4-(bromomethyl)benzoate(2417-72-3)

Safety Data

• Hazard Codes: C
• Statements: 22-34-43
• Safety Statements: 26-36/37/39-45-25
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 2417-72-3(Hazardous Substances Data)

Usage

Description

Methyl 4-(bromomethyl)benzoate is an ester derivative of a bromoalkylated benzoic acid, characterized by its white to off-white crystalline powder appearance. It is a lachrymator and serves as an important drug intermediate, with its ester group slightly twisted out of the plane of the central aromatic ring.

Uses

Used in Pharmaceutical Industry:
Methyl 4-(bromomethyl)benzoate is used as a key intermediate in the synthesis of potential anti-HIV agents, contributing to the development of treatments for HIV/AIDS. Its role in this application is due to its unique chemical structure, which allows for further chemical modifications to create effective anti-HIV compounds.
Additionally, Methyl 4-(bromomethyl)benzoate is utilized as a catalyst in the rearrangement of benzylthiothiazoline derivatives, which are crucial in the preparation of aldose reductase inhibitors. Aldose reductase inhibitors are important in the management of diabetic complications, such as neuropathy and retinopathy, making this application significant in the field of diabetes treatment.

InChI:InChI=1/C9H9BrO2/c1-12-9(11)8-4-2-7(6-10)3-5-8/h2-5H,6H2,1H3

Upstream product

• 67-56-1 methanol 
• 52780-16-2 4-bromomethylbenzoyl chloride 
• 6232-88-8 4-bromomethylbenzoic Acid 
• 106-43-4 para-chlorotoluene 
• 99-75-2 4-methyl-benzoic acid methyl ester 
• 186581-53-3 diazomethane 
• 6908-41-4 4-(methoxycarbonyl)benzyl alcohol 
• 1571-08-0 methyl 4-formylbenzoate 
• 106-38-7 para-bromotoluene 
• 99-94-5 p-Toluic acid 
• 874-60-2 4-methyl-benzoyl chloride 
• 94-36-0 dibenzoyl peroxide 
• 108-90-7 chlorobenzene 
• 18107-18-1 diazomethyl-trimethyl-silane 

Downstream Products

• 1571-08-0 methyl 4-formylbenzoate 
• 76469-88-0 methyl 4-(cyanomethyl)benzoate 
• 94224-92-7 methyl 4-(iodomethyl)benzoate 
• 150630-10-7 dimethyl 4,4’-(azanediylbis(methylene))dibenzoate 
• 67249-05-2 (E)-methyl 4-(4-chlorostyryl)benzoate 
• 1149-18-4 (E)-methyl 4-styrylbenzoate 
• 67249-03-0 E-4-[2-(4-bromo-phenyl)-vinyl]-benzoic acid methyl ester 
• 26496-96-8 α-Isovaleryl-β-<4-aethoxycarbonyl-phenyl>-propionsaeure-aethylester 
• 18969-60-3 4-[(2-methyl-1,2-dicarbobenzoxy-hydrazino)-methyl]-benzoic acid 
• 54636-00-9 p-(2-Phenyl-3-oxobutyl)-benzoesaeuremethylester 
• 70539-49-0 methyl 4-(((N,4-dimethylphenyl)sulfonamido)methyl)benzoate 
• 99837-95-3 6-Methoxycarbonylamino-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-methoxycarbonyl-benzyl ester 
• 80037-23-6 1-(4-Methoxycarbonyl-benzyl)-3,3,5-trimethyl-3,4-dihydro-2H-pyrrolium; bromide 
• 160032-28-0 3-thienyl-4-methoxycarbonylbenzyl sulfide 

Relevant articles and documents

Preparation method of 4-bromomethyl methyl benzoate and derivative thereof

The invention provides a preparation method of methyl 4-bromomethyl benzoate and a derivative thereof, and the method comprises an esterification reaction for converting methyl benzoic acid into methyl benzoate and a bromination reaction for converting the methyl benzoate into the methyl 4-bromomethyl benzoate and the derivative thereof, the brominating agent for the bromination reaction is dibromohydantoin, and the structural formulas of the 4-bromomethyl methyl benzoate and the derivatives thereof are shown in the specification, wherein n1 is equal to 0, 1 or 2; n2 is equal to 1 or 2; according to the preparation method disclosed by the invention, the reaction time can be greatly shortened, the reaction yield is high, and the production efficiency is improved.

Photochemical Radical C–H Halogenation of Benzyl N-Methyliminodiacetyl (MIDA) Boronates: Synthesis of α-Functionalized Alkyl Boronates

α-Haloboronates are useful organic synthons that can be converted to a diverse array of α-substituted alkyl borons. Methods to α-haloboronates are limiting and often suffer from harsh reaction conditions. Reported herein is a photochemical radical C-H halogenation of benzyl N-methyliminodiacetyl (MIDA) boronates. Fluorination, chlorination, and bromination reactions were effective by using this protocol. Upon reaction with different nucleophiles, the C?Br bond in the brominated product could be readily transformed to a series of C?C, C?O, C?N, C?S, C?P, and C?I bonds, some of which are difficult to forge with α-halo sp2-B boronate esters. An activation effect of B(MIDA) moiety was found.

Dual Farnesoid X Receptor/Soluble Epoxide Hydrolase Modulators Derived from Zafirlukast

The nuclear farnesoid X receptor (FXR) and the enzyme soluble epoxide hydrolase (sEH) are validated molecular targets to treat metabolic disorders such as non-alcoholic steatohepatitis (NASH). Their simultaneous modulation in vivo has demonstrated a triad of anti-NASH effects and thus may generate synergistic efficacy. Here we report dual FXR activators/sEH inhibitors derived from the anti-asthma drug Zafirlukast. Systematic structural optimization of the scaffold has produced favorable dual potency on FXR and sEH while depleting the original cysteinyl leukotriene receptor antagonism of the lead drug. The resulting polypharmacological activity profile holds promise in the treatment of liver-related metabolic diseases.