7560-44-3

Basic information

• Product Name: METHYL 4-CHLOROCINNAMATE
• Synonyms: 4-CHLOROCINNAMIC ACID METHYL ESTER;METHYL 4-CHLOROCINNAMATE;methyl p-chlorocinnamate;4-Chloromethyl cinnamate;3-(4-Chlorophenyl)propenoic acid methyl ester;4-Chlorobenzeneacrylic acid methyl ester;Methyl (2E)-3-(4-chlorophenyl)acrylate;Methyl 4-Chlorociamate
• CAS NO: 7560-44-3
• Molecular Formula: C10H9ClO2
• Molecular Weight: 196.63
• EINECS: 231-451-3
• Product Categories: Aromatic Esters;Cinnamic acid
• Mol File: 7560-44-3.mol
• Article Data: 65

Chemical Properties

• Melting Point: 76-77°C
• Boiling Point: 292.8 °C at 760 mmHg
• Flash Point: 144.4 °C
• Appearance: /
• Density: 1.211 g/cm³
• Vapor Pressure: 0.0018mmHg at 25°C
• Refractive Index: 1.572
• BRN: 2045629
• CAS DataBase Reference: METHYL 4-CHLOROCINNAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 4-CHLOROCINNAMATE(7560-44-3)
• EPA Substance Registry System: METHYL 4-CHLOROCINNAMATE(7560-44-3)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39-37
• Hazardous Substances Data: 7560-44-3(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 54, p. 2027, 1989 DOI: 10.1021/jo00270a001

InChI:InChI=1/C10H9ClO2/c1-13-10(12)7-4-8-2-5-9(11)6-3-8/h2-7H,1H3/b7-4+

Upstream product

• 67-56-1 methanol 
• 1615-02-7 p-chlorocinnamic acid 
• 104-88-1 4-chlorobenzaldehyde 
• 96-32-2 bromoacetic acid methyl ester 
• 637-87-6 1-Chloro-4-iodobenzene 
• 292638-85-8 acrylic acid methyl ester 
• 586-78-7 para-nitrophenyl bromide 
• 1075-77-0 4-chlorocinnamaldehyde 
• 35086-79-4 p-chlorocinnamoyl chloride 
• 1445-45-0 Trimethyl orthoacetate 
• 33934-10-0 3-(4-chloro-phenyl)-2-methyl-isoxazolidin-5-one 
• 106-47-8 4-chloro-aniline 
• 74-88-4 methyl iodide 
• 201230-82-2 carbon monoxide 

Downstream Products

• 893751-05-8 methyl 2-(4-chlorophenyl)cyclopropanecarboxylate 
• 24583-70-8 (E)-3-(p-chlorophenyl)prop-2-en-1-ol 
• 137310-14-6 trimethyl 2-(4-chlorophenyl)propane-1,1,3-tricarboxylate 
• 1242096-10-1 dimethyl 3-(4-chlorophenyl)-2,2-dimethylpentane-1,5-dioate 
• 1242096-24-7 dimethyl 3-(4-chlorophenyl)-2,2,6,6-tetramethyl-5-oxo-heptane-1,7-dioate 
• 1242096-37-2 1-isopropyl 7-methyl 3-(4-chlorophenyl)-2,2,6,6-tetramethyl-5-oxoheptanedioate 
• 1242096-38-3 1-isopropyl-7-methyl 3-(4-chlorophenyl)-2,2,6,6-tetramethyl-5-oxoheptanedioate 
• 1242096-39-4 1-tert-butyl 7-methyl 3-(4-chlorophenyl)-2,2,6,6-tetramethyl-5-oxoheptanedioate 
• 1242096-11-2 dimethyl 3-(4-chlorophenyl)-2-ethyl-2-methylpentane-1,5-dioate 
• 1264276-38-1 methyl (Z)-3-(4-chlorophenyl)-3-(4-methoxyphenyl)acrylate 
• 1264276-61-0 methyl (Z)-3-(4-chlorophenyl)-3-(4-nitrophenyl)acrylate 
• 113210-96-1 methyl (E)-3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)acrylate 
• 50561-69-8 methyl 3-(4-chlorophenyl)propanoate 
• 14548-38-0 6-chloro-1-indanone 

Relevant articles and documents

Oxidative esterification of alcohols by a single-side organically decorated Anderson-type chrome-based catalyst

The direct esterification of alcohols with non-noble metal-based catalytic systems faces great challenges. Here, we report a new chrome-based catalyst stabilized by a single pentaerythritol decorated Anderson-type polyoxometalate, [N(C4H9)4]3[CrMo6O18(OH)3C{(OCH2)3CH2OH}], which can realize the efficient transformation from alcohols to esters by H2O2oxidation in good yields and high selectivity without extra organic ligands. A variety of alcohols with different functionalities including some natural products and pharmaceutical intermediates are tolerated in this system. The chrome-based catalyst can be recycled several times and still keep the original configuration and catalytic activity. We also propose a reasonable catalytic mechanism and prove the potential for industrial applications.

Palladium Ion Catalysed Oxidative C–C Bond Formation Reactions in Arylboronic Acid: Application of Cordierite Monolith Coated Catalyst

Abstract: Catalytic efficiency of palladium ion substituted in TiO2, Ti0.97Pd0.03O1.97 is successfully exploited for the oxidative homocoupling of arylboronic acid and oxidative Heck coupling reactions between arylboronic acid and olefins. The reaction protocol provides direct approach to synthesize biphenyls and cinnamates from moderate to good yield with good functional group tolerance. As a result, 11 symmetrical biaryls and 14 cinnamates were synthesized from readily available arylboronic acids. Ti0.97Pd0.03O1.97 powder catalyst is synthesized by solution combustion method and characterized by powder X-ray diffraction. The C–C bond formation reactions were carried out by catalyst cartridge method using Ti0.97Pd0.03O1.97 catalyst coated cordierite monolith. Coating of the catalyst on a cordierite monolith enhanced the applicability of the catalyst and made handling and recycling of the catalyst very easy. Catalyst was recovered and recycled for eight times in both homocoupling and oxidative Heck coupling reactions. The turnover number for both the reactions found to be 443 and 424, respectively. Graphic Abstract: [Figure not available: see fulltext.].

Highly Regio- A nd Enantioselective Hydrogenation of Conjugated α-Substituted Dienoic Acids

Highly regio- A nd enantioselective hydrogenation of conjugated α-substituted dienoic acids was realized for the first time using Trifer-Rh complex, providing a straightforward method for the synthesis of chiral α-substituted ?,?′-unsaturated acids. DFT calculations revealed N+H-O hydrogen bonding interaction is formed to stabilize the transition state and the coordination of 4,5-double bond to Rh(III) center would facilitate the reductive elimination process. This hydrogenation provided a gram-scale synthesis of the precursor of sacubitril.