946-99-6

Basic information

• Product Name: Methyl 3-(4-bromomethyl)cinnamate
• Synonyms: Methyl 3-(4-(broMoMethyl)phenyl)acrylate;Methyl 3-(4-bromomethyl)cinnamate 4-Bromomethylcinnamic acid methyl ester;946-99-6;Methyl 4-bromomethylcinnamate, >=98%;4-bromomethyl cinnamate;(E)-methyl 3-(4-(bromomethyl)phenyl)acrylate;METHYL-P-BROMOMETHYL-CINNAMATE;METHYL-4-BROMOMETHYL-CINNAMATE
• CAS NO: 946-99-6
• Molecular Formula: C₁₁H₁₁BrO₂
• Molecular Weight: 255.11
• Product Categories: Cinnamic acid;Aromatics;Inhibitors
• Mol File: 946-99-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 62-63 °C
• Boiling Point: 333.916 °C at 760 mmHg
• Flash Point: 155.747 °C
• Appearance: /
• Density: 1.418 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.596
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: Chloroform, DMSO, Ethyl Acetate, Methanol
• CAS DataBase Reference: Methyl 3-(4-bromomethyl)cinnamate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 3-(4-bromomethyl)cinnamate(946-99-6)
• EPA Substance Registry System: Methyl 3-(4-bromomethyl)cinnamate(946-99-6)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 946-99-6(Hazardous Substances Data)

Usage

Description

Methyl 3-(4-bromomethyl)cinnamate is an organic compound that serves as an important intermediate in the synthesis of various chemical compounds. It is characterized by the presence of a cinnamate group with a bromine atom attached to the methyl group, which contributes to its unique chemical properties and reactivity.

Uses

Used in Pharmaceutical Industry:
Methyl 3-(4-bromomethyl)cinnamate is used as a key intermediate in the synthesis of p-, m-, and o-bis-(2-chloroethyl)aminomethylcinnamic acid hydrochloride and their esters. These compounds are known as inhibitors and have potential applications in the development of pharmaceutical drugs, particularly in the treatment of various diseases and disorders.
Used in Chemical Synthesis:
Methyl 3-(4-bromomethyl)cinnamate is also used in the synthesis of other organic compounds, such as esters and amines, which can be further utilized in various chemical processes and applications. Its unique structure and reactivity make it a valuable building block in the creation of new and innovative chemical compounds.

InChI:InChI=1/C11H11BrO2/c1-14-11(13)7-6-9-2-4-10(8-12)5-3-9/h2-7H,8H2,1H3/b7-6+

Upstream product

• 1866-39-3 4-methylcinnamic acid 
• 104-87-0 4-methyl-benzaldehyde 
• 7560-43-2 methyl 3-(4-methylphenyl)acrylate 

Downstream Products

• 86911-06-0 1-benzoyl-3-<4-(2-methoxycarbonylvinyl)benzyl>imidazolium bromide 
• 74003-11-5 3-(4-((1H-imidazol-1-yl)methyl)phenyl)acrylic acid 
• 87087-51-2 methyl p-phenoxymethylcinnamate 
• 87087-53-4 methyl p-dimethylaminomethylcinnamate 
• 87087-47-6 methyl p-nitromethylcinnamate 
• 87087-40-9 methyl p-chloromethylcinnamate 

Relevant articles and documents

β-Carboline and N-hydroxycinnamamide hybrids as anticancer agents for drug-resistant hepatocellular carcinoma

In an effort to develop anticancer agents that may overcome drug resistance, the number one reason in caner death, we have developed a series of novel hybrids of β-carboline and N-hydroxycinnamamide as histone deacetylase (HDAC) inhibitors. Most of the hybrids 13a-p showed strong antiproliferative effects with low-micromolar IC50 values against four human cancer cells. The most potent compound of series 13p exhibited high HDAC1/6 inhibitory effects, and also increased the acetylation levels of histone H3, H4 and α-tubulin. Importantly, 13p demonstrated high anticancer potency against drug-sensitive HepG2 and Bel7402 cells and drug-resistant Bel7402/5FU cells. Hybrid 13p triggered significant apoptosis by regulating apoptotic relative proteins expression in these Bel7402/5FU cells. Finally, 13p induced a substantial amount of autophagic flux activity by the accretion of the expression of LC3-II and the degeneration of expression of p62 and LC3-I in Bel7402/5FU cells. Overall, 13p is a novel β-carboline/N-hydroxycinnamamide hybrid with significant anticancer potency that warrants further evaluation for the treatment of drug-resistant hepatocellular carcinoma.

The Determination of Inductive Effects by 13C Nuclear Magnetic Resonance Spectrometry

A series of meta- and para-XCH2-substituted methyl cinnamates has been prepared and the 13C n.m.r. chemical shifts of the α- and β-side-chain carbons have been determined in ethanol.In the majority of cases the magnitudes of the substituent-induced chemic