METHYL 4-CHLOROBENZOATE

Base Information

• Chemical Name: METHYL 4-CHLOROBENZOATE
• CAS No.: 1126-46-1
• Molecular Formula: C8H7ClO2
• Molecular Weight: 170.595
• Hs Code.: 29163990
• European Community (EC) Number: 214-420-9
• NSC Number: 8366
• UNII: M0U80J80VA
• DSSTox Substance ID: DTXSID5022148
• Nikkaji Number: J47.050C
• Wikidata: Q27283319
• Mol file: 1126-46-1.mol

Synonyms:Benzoicacid, p-chloro-, methyl ester (6CI,7CI,8CI);4-(Methoxycarbonyl)chlorobenzene;4-Carbomethoxyphenyl chloride;4-Chlorobenzoic acid methyl ester;5-Chloro-2-benzoic acid methyl ester;Methylp-chlorobenzoate;NSC 8366;p-Chlorobenzoic acid methyl ester;

Chemical Property of METHYL 4-CHLOROBENZOATE

Chemical Property:

• Appearance/Colour: colourless to white crystals
• Vapor Pressure: 0.12mmHg at 25°C
• Melting Point: 42-44 °C(lit.)
• Refractive Index: 1.528
• Boiling Point: 219.4 °C at 760 mmHg
• Flash Point: 106.667 °C
• PSA: 26.30000
• Density: 1.225 g/cm³
• LogP: 2.12660
• Storage Temp.: 0-10°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 170.0134572
• Heavy Atom Count: 11
• Complexity: 139

Purity/Quality:

99% ^*data from raw suppliers

Methyl 4-chlorobenzoate ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)C1=CC=C(C=C1)Cl
• Uses: Methyl 4-chlorobenzoate was used in quantitative determination of chlorophenoxyisobutyrate (CPIB) and salicylic acid, the metabolites of clofibrate and aspirin, by GC-MS method.

Technology Process of METHYL 4-CHLOROBENZOATE

There total 186 articles about METHYL 4-CHLOROBENZOATE 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: 84.0%

methanol (67-56-1) + carbon monoxide (201230-82-2) + 4-chlorophenylboronic acid pinacol ester (195062-61-4) → Methyl 4-chlorobenzoate (1126-46-1) + 4,4'-dichlorobiphenyl (2050-68-2)

Guidance literature:

With palladium diacetate; triphenylphosphine; p-benzoquinone; at 20 ℃; for 7h; under 760.051 Torr;

DOI:10.1002/adsc.200900836

Reference yield: 56.0%

2-(4-chloro-phenyl)-5,5-dimethyl-[1,3,2]dioxaborinane (827605-29-8) + methanol (67-56-1) + carbon monoxide (201230-82-2) → Methyl 4-chlorobenzoate (1126-46-1) + 4,4'-dichlorobiphenyl (2050-68-2) + 4,4'-Dichlorobenzophenone (90-98-2)

Guidance literature:

With palladium diacetate; triphenylphosphine; p-benzoquinone; at 20 ℃; for 5h; under 760.051 Torr;

DOI:10.1002/adsc.200900836

Reference yield: 53.0%

N,N-dimethyl-ethanamine (598-56-1) + para-chlorobenzoic acid (74-11-3) → Methyl 4-chlorobenzoate (1126-46-1) + ethyl 4-chlorobenzoate (7335-27-5)

Guidance literature:

With dimethyl acetylenedicarboxylate; In dichloromethane; at 20 ℃; for 42h;

DOI:10.1016/j.tet.2012.08.024

upstream raw materials:

4-Cyanochlorobenzene

methanol

4-chloro-benzoyl chloride

para-chlorobenzoic acid

Downstream raw materials:

1-(4-chlorophenyl)-2-(pyridin-2-yl)ethanone

methyl 3-nitro-4-chlorobenzoate

4-chloro-N-hydroxybenzamide

1-(4-Chlorophenyl)-2-(4-pyrimidinyl)ethenol

Refernces

• 1、 El Mansouri, Az-eddine,Oubella, Ali,Danoun, Karim,Ahmad, Mehdi,Neyts, Johan,Jochmans, Dirk,Snoeck, Robert,Andrei, Graciela,Morjani, Hamid,Zahouily, Mohamed,Lazrek, Hassan B.. "Discovery of novel furo[2,3-d]pyrimidin-2-one–1,3,4-oxadiazole hybrid derivatives as dual antiviral and anticancer agents that induce apoptosis". . . Retrieved 2021.
• 2、 Yu, Mingxin,Wen, Weijiang,Wang, Zhiyuan. "Novel C-C bond cleavage from arylacetonitriles in alcohols to aryl carboxylic esters using potassium iodide and catalytic amount of samarium". . p. 2851 - 2857. Retrieved 2006.
• 3、 Antonietti, Markus,Cheng, Jiajia,Lin, Sen,Savateev, Aleksandr,Wan, Qiang,Wang, Chong,Wang, Xinchen. "Efficient aerobic oxidation of alcohols to esters by acidified carbon nitride photocatalysts". . p. 116 - 125. Retrieved 2021.
• 4、 Niedan,Schoeler. "Natural formation of chlorobenzoic acids (CBA) and distinction between PCB-degraded CBA". . p. 1233 - 1241. Retrieved 1997.
• 5、 Balinge, Kamlesh Rudreshwar,Khiratkar, Avinash Ganesh,Bhagat, Pundlik Rambhau. "Polymer supported Zn-salen complexes: An effective one-pot oxidative esterification of aldehydes to carboxylic esters". . p. 1085 - 1095. Retrieved 2017.
• 6、 Gawande, Manoj B.,Rathi, Anuj K.,Tucek, Jiri,Safarova, Klara,Bundaleski, Nenad,Teodoro, Orlando M.N.D.,Kvitek, Libor,Varma, Rajender S.,Zboril, Radek. "Magnetic gold nanocatalyst (nanocat-Fe-Au): Catalytic applications for the oxidative esterification and hydrogen transfer reactions". . p. 4137 - 4143. Retrieved 2014.
• 7、 Okimoto, Mitsuhiro,Nagata, Yuji,Sueda, Satoru,Takahashi, Yukio. "One Pot Electrooxidative Conversion of Aromatic 1,2-Diketones into Methyl Carboxylates". . p. 3771 - 3776. Retrieved 2003.
• 8、 Teimuri-Mofrad, Reza,Rahimpour, Keshvar,Rezaei, Hannaneh,Valizadeh, Hassan,Aghaiepour, Alireza. "Study of new synthesized ferrocenyl ionic liquids in oxidative esterification reaction". . p. 1425 - 1435. Retrieved 2018.
• 9、 Zhang, Chengming,Wang, Yongzhao. "Chloride-Induced Highly Active Au Catalyst for Methyl Esterification of Alcohols". . p. 249 - 254. Retrieved 2019.
• 10、 Gupta, Jeetendra Kumar,Mishra, Pradeep. "Pharmacological screening of some newly synthesized triazoles for H1 receptor antagonist activity". . p. 2260 - 2271. Retrieved 2017.