Methyl 4-isopropylbenzoate

Base Information

• Chemical Name: Methyl 4-isopropylbenzoate
• CAS No.: 20185-55-1
• Molecular Formula: C11H14O2
• Molecular Weight: 178.231
• Hs Code.: 2916399090
• NSC Number: 20013
• UNII: PU4R42BT2Q
• DSSTox Substance ID: DTXSID70281066
• Nikkaji Number: J102.618F
• Wikidata: Q82014809
• Mol file: 20185-55-1.mol

Synonyms:Methyl 4-isopropylbenzoate;20185-55-1;Methyl cumate;methyl 4-propan-2-ylbenzoate;Methyl p-isopropylbenzoate;Benzoic acid, 4-(1-methylethyl)-, methyl ester;methyl 4-(1-methylethyl)benzoate;NSC-20013;PU4R42BT2Q;4-Isopropylmethyl benzenecarboxylate;Methyl cuminate;Benzoic acid, p-isopropyl-, methyl ester;UNII-PU4R42BT2Q;Methyl 4-iso-propylbenzoate;SCHEMBL84424;methyl 4-(propan-2-yl)benzoate;DTXSID70281066;NSC20013;MFCD06203666;AKOS002392956;AS-11247;4-(1-methylethyl)benzoic acid methyl ester;CS-0449302;FT-0693583;M3307;Benzoic acid,4-(1-methylethyl)-,methyl ester;Ethyl?2-(1-benzylpiperidin-4-ylidene)acetate;D95419;A920965

Chemical Property of Methyl 4-isopropylbenzoate

Chemical Property:

• Vapor Pressure: 0.0285mmHg at 25°C
• Refractive Index: 1.5
• Boiling Point: 245.6 °C at 760 mmHg
• Flash Point: 106.9 °C
• PSA: 26.30000
• Density: 1.004 g/cm³
• LogP: 2.59660
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 178.099379685
• Heavy Atom Count: 13
• Complexity: 167

Purity/Quality:

99% ^*data from raw suppliers

Methyl 4-Isopropylbenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1=CC=C(C=C1)C(=O)OC

Technology Process of Methyl 4-isopropylbenzoate

There total 42 articles about Methyl 4-isopropylbenzoate 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%

p-isopropylbenzoic acid (536-66-3) + methyl iodide (74-88-4) → p-isopropylbenzoic acid methyl ester (20185-55-1)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1021/acs.jmedchem.9b01912

Reference yield: 96.0%

methanol (67-56-1) + 1-(4-isopropylphenyl)ethanol (1475-10-1) → p-isopropylbenzoic acid methyl ester (20185-55-1)

Guidance literature:

With N-iodo-succinimide; 1,10-Phenanthroline; oxygen; potassium carbonate; copper dichloride; In dimethyl sulfoxide; at 140 ℃; for 12h; under 3750.38 Torr; Molecular sieve;

DOI:10.1016/j.chempr.2020.09.006

Reference yield: 94.0%

4-methoxycarbonylphenyl bromide (619-42-1) + isopropyl zinc bromide (77047-87-1) → p-isopropylbenzoic acid methyl ester (20185-55-1)

Guidance literature:

4-methoxycarbonylphenyl bromide; With C₄₀H₅₅Cl₅N₃Pd; In toluene; at 0 ℃; for 0.0833333h; Inert atmosphere; Cooling with ice;

isopropyl zinc bromide; In tetrahydrofuran; toluene; at 23 ℃; for 0.5h; Inert atmosphere;

DOI:10.1002/anie.201205747 DOI:10.1002/anie.201205747

upstream raw materials:

diazomethane

p-isopropylbenzoic acid

methanol

p-isopropylbenzoyl chloride

Downstream raw materials:

terephthalic acid

4-<1,1-Dinitro-ethyl>-benzoesaeure

methyl 3-iodo-4-isopropylbenzoate

3-iodo-4-isopropylbenzoic acid

Refernces

• 1、 Campbell,Spaeth. "-". . p. 5933,5934. Retrieved 1959.
• 2、 Borlinghaus, Niginia,Sch?nfeld, Barbara,Heitz, Stephanie,Klee, Johanna,Vukeli?, Stella,Braje, Wilfried M.,Jolit, Anais. "Enabling Metallophotoredox Catalysis in Parallel Solution-Phase Synthesis Using Disintegrating Reagent Tablets". supporting information. p. 16535 - 16547. Retrieved 2021/12/02.
• 3、 Bismuto, Alessandro,Boehm, Philip,Morandi, Bill,Roediger, Sven. "Palladium-Catalyzed Chlorocarbonylation of Aryl (Pseudo)Halides Through In Situ Generation of Carbon Monoxide". supporting information. p. 17887 - 17896. Retrieved 2020/08/19.