Methyl 4-methoxybenzoate

Base Information

• Chemical Name: Methyl 4-methoxybenzoate
• CAS No.: 121-98-2
• Molecular Formula: C9H10O3
• Molecular Weight: 166.177
• Hs Code.: 29189900
• European Community (EC) Number: 204-513-2
• NSC Number: 7324
• UNII: 2MFL7873W9
• DSSTox Substance ID: DTXSID7047645
• Nikkaji Number: J33.855I
• Wikipedia: Methyl_anisate
• Wikidata: Q6823933
• Metabolomics Workbench ID: 45673
• ChEMBL ID: CHEMBL1762668
• Mol file: 121-98-2.mol

Synonyms:methyl 4-anisate;methyl p-anisate

Chemical Property of Methyl 4-methoxybenzoate

Chemical Property:

• Appearance/Colour: white crystalline mass
• Vapor Pressure: 0.000741mmHg at 25°C
• Melting Point: 48-52 °C(lit.)
• Refractive Index: 1.5224 (estimate)
• Boiling Point: 255.999 °C at 760 mmHg
• Flash Point: 98.062 °C
• PSA: 35.53000
• Density: 1.098 g/cm³
• LogP: 1.48180
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform, Methanol (Slightly)
• Water Solubility.: 643.1mg/L(20 oC)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 166.062994177
• Heavy Atom Count: 12
• Complexity: 148

Purity/Quality:

99%, ^*data from raw suppliers

Methyl4-Methoxybenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: COC1=CC=C(C=C1)C(=O)OC
• Description: Methyl anisate is the methyl ester of p-anisic acid.
• Uses: Methyl p-anisate has been used as a standard for the quantification of odorant compounds in French mimosa absolute oil by GC-Sniffing.

Technology Process of Methyl 4-methoxybenzoate

There total 342 articles about Methyl 4-methoxybenzoate 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: 98.0%

→ methyl 4-methoxybenzoate (121-98-2) + 4-methoxybenzoic acid (100-09-4)

Guidance literature:

Reference yield: 92.0%

tert.-butylhydroperoxide (75-91-2) + 4-Methoxybenzyl alcohol (105-13-5) → methyl 4-methoxybenzoate (121-98-2) + 4-methoxybenzoic acid (100-09-4)

Guidance literature:

With potassium phosphate; copper quinolate; tetra-(n-butyl)ammonium iodide; In water; dimethyl sulfoxide; at 120 ℃; for 24h; Reagent/catalyst; Solvent; Concentration;

DOI:10.1021/jo4016387

Reference yield: 85.5%

methanol (67-56-1) + 1-bromo-4-methoxy-benzene (104-92-7) + carbon monoxide (201230-82-2) → methyl 4-methoxybenzoate (121-98-2) + 4-methoxybenzoic acid (100-09-4)

Guidance literature:

With CoCRACO; sodium tert-pentoxide; sodium hydride; In tetrahydrofuran; for 40h; Irradiation;

DOI:10.1080/00397919308011224

upstream raw materials:

4-methoxy-benzoic acid ; calcium compound

acetic anhydride

methanol

4-methoxybenzoic acid

Downstream raw materials:

1-(4-methoxyphenyl)-2,4,4-trimethylpentane-1,3-dione

methyl 3-(4-methoxybenzoyl)acetate

1-isopropenyl-4-methoxybenzene

2,4-bis-(4-methoxy-phenyl)-4-methyl-pent-2-ene

Refernces

• 1、 Matsugi, Masato,Hasegawa, Masakazu,Sadachika, Daisuke,Okamoto, Sachina,Tomioka, Mami,Ikeya, Yoshimi,Masuyama, Araki,Mori, Yuji. "Preparation and condensation reactions of a new light-fluorous Mukaiyama reagent: reliable purification with fluorous solid phase extraction for esters and amides". . p. 4147 - 4150. Retrieved 2007.
• 2、 Albaneze-Walker, Jennifer,Bazaral, Charles,Leavey, Tanya,Dormer, Peter G.,Murry, Jerry A.. "Improved carbonylation of heterocyclic chlorides and electronically challenging aryl bromides". . p. 2097 - 2100. Retrieved 2004.
• 3、 Wang, Lin,Neumann, Helfried,Spannenberg, Anke,Beller, Matthias. "Practical: In situ -generation of phosphinite ligands for palladium-catalyzed carbonylation of (hetero)aryl bromides forming esters". . p. 7469 - 7472. Retrieved 2017.
• 4、 Baumstark,Kovac, Franci,Vasquez, Pedro C.. "Oxidation of acetals by dimethyldioxirane". . p. 9 - 12. Retrieved 2002.
• 5、 Yin, Guodong,Gao, Meng,Wang, Zihua,Wu, Yandong,Wu, Anxin. "Direct conversion of aromatic ketones to arenecarboxylic esters via carbon-carbon bond-cleavage reactions". . p. 369 - 372. Retrieved 2008.
• 6、 Leowanawat, Pawaret,Zhang, Na,Percec, Virgil. "Nickel catalyzed cross-coupling of aryl C-O based electrophiles with aryl neopentylglycolboronates". . p. 1018 - 1025. Retrieved 2012.
• 7、 Rankin, Kathryn N.,Liu, Qing,Hendry, Jennifer,Yee, Henry,Noureldin, Nazih A.,Lee, Donald G.. "Mechanisms for the oxidation of para-substituted benzyl alcohols and benzyl ethers by permanganate". . p. 1095 - 1098. Retrieved 1998.
• 8、 Hamdani, Syeda Shamila,Khan, Bilal Ahmad,Ahmed, Muhammad Naeem,Hameed, Shahid,Akhter, Kulsoom,Ayub, Khurshid,Mahmood, Tariq. "Synthesis, crystal structures, computational studies and α-amylase inhibition of three novel 1,3,4-oxadiazole derivatives". . . Retrieved 2020.
• 9、 Tomma, Jumbad H.,Ghali, Thaer S.,Al-Dujaili, Ammar H.. "Synthesis and characterization of some novel liquid crystalline compounds of 1,3,4-oxadiazoline and their hydrazone derivatives". . p. 85 - 94. Retrieved 2018.
• 10、 Larock, Richard C.,Fellows, Constance A.. "Synthesis of Aromatic Carbonyl Compounds via Thallation-Carbonylation of Arenes". . p. 1900 - 1907. Retrieved 1982.