60682-98-6

Basic information

• Product Name: Ethyl 4-bromomethylcinnamate
• Synonyms: 3-(4-Brommethyl)-phenylpropenoic acid ethyl ester;ethyl 3-(4-bromomethyl)cinnamate;Ethyl 4-bromomethylcinnamate;3-(4-Brommethyl)-Phenyl-PropenoicAcid(C12H13BrO2);2-PropenoicAcid,3-[4-(Bromomethyl)-Phenyl]-Ethyl;ETHYL-3-(PARA-(BROMOMETHYL)PHENYL)ACRYLATE;ETHYL(E)-3-(P-(BROMOMETHYL)PHENYL)ACRYLATE;Ethyl 4-bromomethylc
• CAS NO: 60682-98-6
• Molecular Formula: C₁₂H₁₃BrO₂
• Molecular Weight: 269.13
• EINECS: 200-528-9
• Product Categories: Cinnamic acid;Aromatics;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 60682-98-6.mol

Chemical Properties

• Boiling Point: 348°C
• Flash Point: 164°C
• Appearance: /
• Density: 1.370
• Vapor Pressure: 5.27E-05mmHg at 25°C
• Refractive Index: 1.585
• CAS DataBase Reference: Ethyl 4-bromomethylcinnamate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 4-bromomethylcinnamate(60682-98-6)
• EPA Substance Registry System: Ethyl 4-bromomethylcinnamate(60682-98-6)

Safety Data

• Hazardous Substances Data: 60682-98-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 4-bromomethylcinnamate is used as a key intermediate in the synthesis of cinnamamide derivatives, which are known to act as 5α-reductase inhibitors. These inhibitors play a crucial role in the treatment of various androgenetic disorders, such as benign prostatic hyperplasia (BPH) and androgenetic alopecia (male pattern baldness). By inhibiting the enzyme 5α-reductase, these cinnamamide derivatives help regulate the conversion of testosterone to dihydrotestosterone (DHT), thereby mitigating the symptoms associated with these conditions.

InChI:InChI=1/C12H13BrO2/c1-2-15-12(14)8-7-10-3-5-11(9-13)6-4-10/h3-8H,2,9H2,1H3/b8-7+

Upstream product

• 20511-20-0 ethyl p-methylcinnamate 

Downstream Products

• 57716-23-1 4-(2-ethoxycarbonylethenyl)benzyltriphenylphosphonium bromide 
• 82603-88-1 ethyl 4-<2-(3-nitrophenyl)ethenyl>cinnamate 
• 82603-90-5 ethyl 4-<2-(4-dimethylaminophenyl)ethenyl>cinnamate 
• 82603-86-9 ethyl 4-<2-(3-bromophenyl)ethenyl>cinnamate 
• 82603-84-7 ethyl 4-<2-(3-chlorophenyl)ethenyl>cinnamate 
• 82603-82-5 ethyl 4-<2-(3-fluorophenyl)ethenyl>cinnamate 
• 82603-89-2 ethyl 4-<2-(4-methoxyphenyl)ethenyl>cinnamate 
• 82603-87-0 ethyl 4-<2-(4-bromophenyl)ethenyl>cinnamate 
• 82603-85-8 ethyl 4-<2-(4-chlorophenyl)ethenyl>cinnamate 
• 82603-83-6 ethyl 4-<2-(4-fluorophenyl)ethenyl>cinnamate 
• 82603-80-3 ethyl 4-<2-(3-methylphenyl)ethenyl>cinnamate 
• 82603-81-4 ethyl 4-<2-(4-methylphenyl)ethenyl>cinnamate 
• 82603-77-8 ethyl 4-(2-phenylethenyl)cinnamate 
• 58702-63-9 ethyl 4-<2-(4-nitrophenyl)ethenyl>cinnamate 

Relevant articles and documents

Synthesis method of ozagrel intermediate phenol bromomethyl cinnamate

The invention discloses a synthesis method of bromomethyl cinnamate by uisng an ozagrel intermediate, which is characterized in that the p-bromomethyl cinnamate is brominated to obtain phenol bromomethyl cinnamate, and the reaction process comprises the following steps of: 1) under the condition of protective gas, uniformly mixing the p-bromomethyl cinnamate, an auxiliary substance and a solvent A, controlling the reaction temperature to be 110-130 DEG C and the pressure to be 4-6 atmospheric pressures, stirring for 1-2h, maintaining the reaction conditions, starting to drop a mixed aqueous solution C of brominated salt and glacial acetic acid, controlling the dropping time to be 1-3 hours, controlling the temperature to be 140-160 DEG C after dropping, controlling the pressure to be 7-10-10 atmospheric pressures, and finishing the reaction after 4-6 hours; 2) cooling the system, pouring the reaction product into 2-4 times of volume of water, adding a solvent B for extraction, layering, washing an organic layer by water, drying by a drying agent, and concentrating and evaporating to remove the solvent to obtain the product. The synthesis method has the advantages of good selectivity, low cost and high yield.

6-Membered heterocyclic compound and use thereof

A compound represented by the general formula (I) or a salt thereof: [T represents oxygen atom and the like; V represents CH2 and the like; RO1 to RO4 represent hydrogen atom and the like; A represents a linear alkylene group or linear alkenylene group having 2 to 8 carbon atoms and the like; D represents carboxyl group and the like; X represents ethylene group, trimethylene group and the like; E represents —CH(OH)— group and the like; and W represent —U1—(RW1)(RW2)—U2—U3 group (U1 represents a single bond, an alkylene group having 1 to 4 carbon atoms and the like; RW1 and RW2 represent hydrogen atom and the like; U2 represents a single bond, an alkylene group having 1 to 4 carbon atoms and the like; and U3 represent an alkyl group having 1 to 8 carbon atoms and the like), or a residue of a carbon ring or heterocyclic compound], which can be utilized as an active ingredient of medicaments effective for prophylactic and/or therapeutic treatment of skeletal diseases such as osteoporosis and fracture, glaucoma, ulcerative colitis and the like.

The Application of the Hammett Equation to 13C N.M.R. Spectrometry. V. The Transmission of Electronic Effects Through Azophenylene and Ethenylphenylene Groups

The 13C n.m.r. spectra of a number of ethyl (3-aryl)azo-, (4-aryl)azo-, 2-(4-arylethenyl)-cinnamates have been measured in CDCl3.Comparision of the data with those for the corresponding ethyl 3-arylpropenoates has been used to investigate the attenuation of electronic effects by the 3- and 4-azophenylene and the 4-ethenylphenylene linkages.