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Cas Database

20185-55-1

20185-55-1

Identification

Synonyms:Benzoicacid, p-isopropyl-, methyl ester (6CI,7CI,8CI);Methyl 4-isopropylbenzoate;Methyl cumate;Methyl cuminate;Methyl p-isopropylbenzoate;NSC 20013;Methyl 4-(propan-2-yl)benzoate;

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Safety information and MSDS view more

  • Signal Word:no data available

  • Hazard Statement:no data available

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:TRC
  • Product Description:Methyl 4-Isopropylbenzoate
  • Packaging:500mg
  • Price:$ 90
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Methyl 4-Isopropylbenzoate
  • Packaging:5G
  • Price:$ 154
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  • Manufacture/Brand:TCI Chemical
  • Product Description:Methyl 4-Isopropylbenzoate
  • Packaging:1G
  • Price:$ 49
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  • Manufacture/Brand:Rieke Metals
  • Product Description:Methyl 4-Isopropylbenzoate
  • Packaging:5g
  • Price:$ 1943
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  • Manufacture/Brand:Rieke Metals
  • Product Description:Methyl 4-Isopropylbenzoate
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  • Manufacture/Brand:Crysdot
  • Product Description:Methyl 4-Isopropylbenzoate 97%
  • Packaging:25g
  • Price:$ 590
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  • Manufacture/Brand:American Custom Chemicals Corporation
  • Product Description:Methyl 4-Isopropylbenzoate 99.00%
  • Packaging:100G
  • Price:$ 3176.25
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  • Manufacture/Brand:AK Scientific
  • Product Description:Methyl 4-Isopropylbenzoate
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Relevant articles and documentsAll total 43 Articles be found

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Cotter,J.L. et al.

, p. 1917 - 1919 (1963)

-

-

Campbell,Spaeth

, p. 5933,5934 (1959)

-

Dilithium Amides as a Modular Bis-Anionic Ligand Platform for Iron-Catalyzed Cross-Coupling

Neate, Peter G.N.,Zhang, Bufan,Conforti, Jessica,Brennessel, William W.,Neidig, Michael L.

supporting information, p. 5958 - 5963 (2021/08/18)

Dilithium amides have been developed as a bespoke and general ligand for iron-catalyzed Kumada-Tamao-Corriu cross-coupling reactions, their design taking inspiration from previous mechanistic and structural studies. They allow for the cross-coupling of alkyl Grignard reagents with sp2-hybridized electrophiles as well as aryl Grignard reagents with sp3-hybridized electrophiles. This represents a rare example of a single iron-catalyzed system effective across diverse coupling reactions without significant modification of the catalytic protocol, as well as remaining operationally simple.

Enabling Metallophotoredox Catalysis in Parallel Solution-Phase Synthesis Using Disintegrating Reagent Tablets

Borlinghaus, Niginia,Sch?nfeld, Barbara,Heitz, Stephanie,Klee, Johanna,Vukeli?, Stella,Braje, Wilfried M.,Jolit, Anais

supporting information, p. 16535 - 16547 (2021/12/02)

Compressed tablets containing a mixture of a photocatalyst, a nickel catalyst, an inorganic base, and an inert excipient are employed as a fast, safe, and user-friendly chemical delivery system for two different metallophotoredox-catalyzed reactions. This delivery method simplifies the preparation of compound libraries using photoredox chemistry in a parallel setting. The reagent tablets were successfully applied to late-stage functionalization of drug-like intermediates. These tablets can be prepared with various reagents and catalysts in different sizes and be stored on the bench thanks to blister packaging.

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

Wang, Jingjing,Jiang, Feng,Tao, Chaofu,Yu, Han,Ruhlmann, Laurent,Wei, Yongge

supporting information, p. 2652 - 2657 (2021/04/21)

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.

5-Phenyl-1,3,4-oxadiazol-2(3 H)-ones Are Potent Inhibitors of Notum Carboxylesterase Activity Identified by the Optimization of a Crystallographic Fragment Screening Hit

Mahy, William,Willis, Nicky J.,Zhao, Yuguang,Woodward, Hannah L.,Svensson, Fredrik,Sipthorp, James,Vecchia, Luca,Ruza, Reinis R.,Hillier, James,Kj?r, Svend,Frew, Sarah,Monaghan, Amy,Bictash, Magda,Salinas, Patricia C.,Whiting, Paul,Vincent, Jean-Paul,Jones, E. Yvonne,Fish, Paul V.

, p. 12942 - 12956 (2020/11/13)

Carboxylesterase Notum is a negative regulator of the Wnt signaling pathway. There is an emerging understanding of the role Notum plays in disease, supporting the need to discover new small-molecule inhibitors. A crystallographic X-ray fragment screen was performed, which identified fragment hit 1,2,3-Triazole 7 as an attractive starting point for a structure-based drug design hit-To-lead program. Optimization of 7 identified oxadiazol-2-one 23dd as a preferred example with properties consistent with drug-like chemical space. Screening 23dd in a cell-based TCF/LEF reporter gene assay restored the activation of Wnt signaling in the presence of Notum. Mouse pharmacokinetic studies with oral administration of 23dd demonstrated good plasma exposure and partial blood-brain barrier penetration. Significant progress was made in developing fragment hit 7 into lead 23dd (>600-fold increase in activity), making it suitable as a new chemical tool for exploring the role of Notum-mediated regulation of Wnt signaling.

Aerobic Oxidative Cleavage and Esterification of C(OH)–C Bonds

Liu, Mingyang,Zhang, Zhanrong,Yan, Jiang,Liu, Shuaishuai,Liu, Huizhen,Liu, Zhaotie,Wang, Weitao,He, Zhenhong,Han, Buxing

, p. 3288 - 3296 (2020/10/20)

C(OH)–C bonds are widely distributed in naturally renewable biomass, such as carbohydrates, lignin, and their platform molecules. Selective cleavage and functionalization of C(OH)–C bonds is an attractive strategy in terms of producing value-added chemicals from biomass. However, effective transformation of alcohols into esters by activation of C(OH)–C bonds has not been achieved so far. Herein, for the first time, we report selective cleavage and esterification of C(OH)–C bonds, catalyzed by inexpensive copper salts, using environmentally benign oxygen as the oxidant, to afford methyl esters in excellent yields. A diverse range of phenylethanol derivatives that contain C(OH)–C bonds were effectively converted into methyl benzoates. Detailed analysis revealed that the high efficiency and selectivity resulted mainly from the fact that, in addition to the major esterification reaction, the side products (e.g., olefins and acids) were also transformed in situ into esters in the reaction system. C(OH)–C bonds are widely distributed in naturally renewable biomass. In the context of developing future biorefineries, selective cleavage and functionalization of C(OH)–C bonds are crucial and represent an attractive strategy in terms of producing value-added chemical compounds from biomass resources. In the current manuscript, we report, for the first time, an effective and selective method for the cleavage and esterification of C(OH)–C bonds of alcohols to produce esters, by using environmentally benign O2 as the terminal oxidant and inexpensive commercially available copper salts as catalysts. Furthermore, a detailed mechanistic study revealed that, in addition to the major esterification route, side products (e.g., olefins and acids), which are inevitably generated under oxidative and basic conditions, were also simultaneously converted into esters, thus significantly improving the final yields of target ester products. Native lignin represents the only naturally sustainable aromatic resource. Transformation of native lignin into valuable aromatics would make a great contribution to our planet. We report, for the first time, the effective transformation of alcohols into esters by esterification of C(OH)–C bonds, which offers a new way for the simultaneous degradation and functionalization of lignin. This reaction promotes new explorations for biomass valorization.

Process route upstream and downstream products

Process route

tert.-butylhydroperoxide
75-91-2

tert.-butylhydroperoxide

cuminol
536-60-7

cuminol

p-isopropylbenzoic acid methyl ester
20185-55-1

p-isopropylbenzoic acid methyl ester

p-isopropylbenzoic acid
536-66-3

p-isopropylbenzoic acid

Conditions
Conditions Yield
With potassium phosphate; copper quinolate; tetra-(n-butyl)ammonium iodide; In water; dimethyl sulfoxide; at 120 ℃; for 24h;
61%
Methyl 4-chlorobenzoate
1126-46-1

Methyl 4-chlorobenzoate

isopropylmagnesium chloride
1068-55-9

isopropylmagnesium chloride

benzoic acid methyl ester
93-58-3,5705-52-2,80226-58-0

benzoic acid methyl ester

p-isopropylbenzoic acid methyl ester
20185-55-1

p-isopropylbenzoic acid methyl ester

Conditions
Conditions Yield
With 1-methyl-pyrrolidin-2-one; iron(III)-acetylacetonate; In tetrahydrofuran; at -20 ℃; for 0.5h; Inert atmosphere;
23%
15 %Chromat.
4-methylisopropylbenzene
99-87-6

4-methylisopropylbenzene

p-isopropylbenzoic acid methyl ester
20185-55-1

p-isopropylbenzoic acid methyl ester

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

Conditions
Conditions Yield
With sulfuric acid; tetraethylammonium tosylate; Yield given. Multistep reaction. Yields of byproduct given; 1.) electrochemical anodic oxidation, AcOH, MeOH, 2.) RT, 3 h;
methanol
67-56-1

methanol

4-methylisopropylbenzene
99-87-6

4-methylisopropylbenzene

p-isopropylbenzoic acid methyl ester
20185-55-1

p-isopropylbenzoic acid methyl ester

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

Conditions
Conditions Yield
With sodium tetrafluoroborate; sulfuric acid; Yield given. Multistep reaction. Yields of byproduct given; 1.) electrochemical anodic oxidation, AcOH, 2.) RT, 3 h;
methanol
67-56-1

methanol

1-(4-isopropylphenyl)ethanol
1475-10-1

1-(4-isopropylphenyl)ethanol

p-isopropylbenzoic acid methyl ester
20185-55-1

p-isopropylbenzoic acid methyl ester

Conditions
Conditions Yield
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;
96%
methanol
67-56-1

methanol

(4-isopropylbenzaldehyde)
122-03-2

(4-isopropylbenzaldehyde)

p-isopropylbenzoic acid methyl ester
20185-55-1

p-isopropylbenzoic acid methyl ester

Conditions
Conditions Yield
With FeMo6O24(9-)*3H3N*9H(1+); potassium chloride; dihydrogen peroxide; at 65 ℃; for 24h; Schlenk technique;
83%
With tert.-butylhydroperoxide; potassium iodide; In water; at 65 ℃; for 20h;
69%
With manganese(IV) oxide; caesium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-butyl-3-methylimidazolium Tetrafluoroborate; at 20 ℃; for 24h; Inert atmosphere;
64%
4-methoxycarbonylphenyl bromide
619-42-1

4-methoxycarbonylphenyl bromide

isopropyl zinc bromide
77047-87-1

isopropyl zinc bromide

p-isopropylbenzoic acid methyl ester
20185-55-1

p-isopropylbenzoic acid methyl ester

Conditions
Conditions Yield
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;
94%
methanol
67-56-1

methanol

cuminol
536-60-7

cuminol

p-isopropylbenzoic acid methyl ester
20185-55-1

p-isopropylbenzoic acid methyl ester

Conditions
Conditions Yield
With sodium methylate; potassium iodide; at 15 ℃; Electrochemical reaction;
83%
With Pyridine-2,6-dicarboxylic acid; dihydrogen peroxide; trifluoroacetic acid; zinc dibromide; In water; at 20 ℃; for 16h;
82%
With potassium chloride; dihydrogen peroxide; C5H12CrMo6O25(3-)*3C16H36N(1+); In water; at 65 ℃; for 36h; Schlenk technique;
75%
With oxygen; potassium carbonate; at 60 ℃; for 24h; under 750.075 Torr; Schlenk technique; Green chemistry;
89 %Chromat.
With oxygen; at 60 ℃; under 760.051 Torr;
2-iodo-propane
75-30-9

2-iodo-propane

methyl 4-iodobenzoate
619-44-3

methyl 4-iodobenzoate

p-isopropylbenzoic acid methyl ester
20185-55-1

p-isopropylbenzoic acid methyl ester

Conditions
Conditions Yield
2-iodo-propane; With zinc; In tetrahydrofuran; at 20 ℃; Inert atmosphere;
methyl 4-iodobenzoate; With 2,2':6,2''-terpyridine; lithium tetrafluoroborate; nickel dichloride; In tetrahydrofuran; at 40 ℃; for 40h; Inert atmosphere;
91%
4-methoxycarbonylphenyl bromide
619-42-1

4-methoxycarbonylphenyl bromide

isopropyl zinc bromide
77047-87-1

isopropyl zinc bromide

p-isopropylbenzoic acid methyl ester
20185-55-1

p-isopropylbenzoic acid methyl ester

p-(methoxycarbonyl)-n-propylbenzene
81631-63-2

p-(methoxycarbonyl)-n-propylbenzene

Conditions
Conditions Yield
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; In tetrahydrofuran; toluene; at 0 - 20 ℃; for 3h; Inert atmosphere;
4-methoxycarbonylphenyl bromide; With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]-(3-chloropyridyl)palladium(II) dichloride; In toluene; at 0 ℃; for 0.0833333h; Inert atmosphere; Cooling with ice;
isopropyl zinc bromide; In tetrahydrofuran; toluene; at 23 ℃; for 0.5h; Overall yield = 99 %; Inert atmosphere;

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  • Debye Scientific
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