Methyl 4-chlorocinnamate

Base Information

• Chemical Name: Methyl 4-chlorocinnamate
• CAS No.: 7560-44-3
• Molecular Formula: C₁₀H₉ClO₂
• Molecular Weight: 196.633
• Hs Code.: 29163990
• European Community (EC) Number: 231-451-3
• NSC Number: 155559
• DSSTox Substance ID: DTXSID101194681
• Nikkaji Number: J592.285B,J307.878G
• Wikidata: Q76303459
• ChEMBL ID: CHEMBL2285934
• Mol file: 7560-44-3.mol

Synonyms:Methyl 4-chlorocinnamate;7560-44-3;Methyl 3-(4-chlorophenyl)acrylate;Methyl p-chlorocinnamate;20754-21-6;(E)-methyl 3-(4-chlorophenyl)acrylate;4-Chlorocinnamic Acid Methyl Ester;methyl (E)-3-(4-chlorophenyl)prop-2-enoate;methyl (2E)-3-(4-chlorophenyl)prop-2-enoate;Cinnamic acid, p-chloro-, methyl ester;2-Propenoic acid, 3-(4-chlorophenyl)-, methyl ester;EINECS 231-451-3;NSC155559;NSC 155559;methyl 3-(4-chlorophenyl)prop-2-enoate;MFCD00075790;ghl.PD_Mitscher_leg0.367;SCHEMBL198277;CHEMBL2285934;DTXSID101194681;BBL104052;STL557866;(E)-methyl3-(4-chlorophenyl)acrylate;AKOS005068361;CS-W015691;FS-4273;NSC-155559;4-Chlorobenzeneacrylic acid methyl ester;BP-12845;C1672;CS-0369105;3-(4-Chlorophenyl)-acrylic acid methyl ester;EN300-186970;EN300-364933;(E)-3-(4-chlorophenyl)-acrylic acid methyl ester;A838459;(E)-3-(4-chloro-phenyl)-acrylic acid methyl ester;J-502043;(2E)-3-(4-Chlorophenyl)-2-propenoic acid methyl ester;2-Propenoic acid, 3-(4-chlorophenyl)-, methyl ester, (2E)-

Chemical Property of Methyl 4-chlorocinnamate

Chemical Property:

• Vapor Pressure: 0.0018mmHg at 25°C
• Melting Point: 76-77°C
• Refractive Index: 1.572
• Boiling Point: 292.8 °C at 760 mmHg
• Flash Point: 144.4 °C
• PSA: 26.30000
• Density: 1.211 g/cm³
• LogP: 2.52620
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 196.0291072
• Heavy Atom Count: 13
• Complexity: 193

Purity/Quality:

99%, ^*data from raw suppliers

Methyl 4-Chlorocinnamate ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C=CC1=CC=C(C=C1)Cl
• Isomeric SMILES: COC(=O)/C=C/C1=CC=C(C=C1)Cl

Technology Process of Methyl 4-chlorocinnamate

There total 35 articles about Methyl 4-chlorocinnamate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

1-Chloro-4-iodobenzene (637-87-6) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → methyl 4-chlorocinnamate (7560-44-3,20754-21-6,20754-24-9)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 130 ℃; for 2h; Catalytic behavior; Inert atmosphere;

DOI:10.1039/c9ra00460b

Reference yield: 98.0%

Methyl diethylphosphonoacetate (1067-74-9) + 4-chlorobenzaldehyde (104-88-1) → methyl 4-chlorocinnamate (7560-44-3,20754-21-6,20754-24-9)

Guidance literature:

Methyl diethylphosphonoacetate; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h; Inert atmosphere;

4-chlorobenzaldehyde; In tetrahydrofuran; hexane; at 20 ℃; Inert atmosphere;

DOI:10.1021/acs.orglett.0c00915

Reference yield: 97.0%

bromochlorobenzene (106-39-8) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → methyl 4-chlorocinnamate (7560-44-3,20754-21-6,20754-24-9)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 70 ℃; for 0.333333h;

DOI:10.1002/aoc.3475

upstream raw materials:

4-chlorobenzaldehyde

methanol

p-chlorocinnamic acid

bromoacetic acid methyl ester

Downstream raw materials:

methyl 3-(4-chlorophenyl)propanoate

4-(4-chlorophenyl)-3-cyano-6-methylpyridine-2(1H)-thione

3-Amino-4-(4-chloro-phenyl)-6-methyl-thieno[2,3-b]pyridine-2-carboxylic acid ethyl ester

4-(4-chloro-phenyl)-6-methyl-2-methylsulfanyl-nicotinonitrile

Refernces

• 1、 Wang, Jingjing,Jiang, Feng,Tao, Chaofu,Yu, Han,Ruhlmann, Laurent,Wei, Yongge. "Oxidative esterification of alcohols by a single-side organically decorated Anderson-type chrome-based catalyst". supporting information. p. 2652 - 2657. Retrieved 2021/04/21.
• 2、 Liu, Xian,Liu, Song,Wang, Quanjun,Zhou, Gang,Yao, Lin,Ouyang, Qin,Jiang, Ru,Lan, Yu,Chen, Weiping. "Highly Regio- A nd Enantioselective Hydrogenation of Conjugated α-Substituted Dienoic Acids". supporting information. p. 3149 - 3154. Retrieved 2020/04/09.