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Quality Control of [ 106-36-5 ] Purity: 99+% SDS Specification

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Product Details of [ 106-36-5 ]

CAS No. :	106-36-5
Formula :	C₆H₁₂O₂
M.W :	116.16
SMILES Code :	CCC(OCCC)=O
English Name :	Propyl propionate
MDL No. :	MFCD00009373
InChI Key :	MCSINKKTEDDPNK-UHFFFAOYSA-N
Pubchem ID :	7803

Safety of [ 106-36-5 ]

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Application In Synthesis of [ 106-36-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 106-36-5 ]

[ 106-36-5 ] Synthesis Path-Downstream 1~14

1
[ CAS Unavailable ]
[ 106-36-5 ]

Yield	Reaction Conditions	Operation in experiment
99%	With dihydrogen peroxide; bromine In dichloromethane; water at 20℃; for 2h;
72%	With water; potassium iodide at 20℃; for 3h; Electrochemical reaction; Green chemistry;
72%	With calcium chloride dihydrate; oxone; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; water In dichloromethane at 20℃; for 4h;	General procedure for oxidative esterification of primary alcohols General procedure: The respective alcohol (1.0 mmol) was added to a suspension of Oxone (400.0 mg, m., CaCl2*2H2O (73.5 mg, 0.5 mmol) and TEMPO (1.6 mg, 0.01 mmol) in dichloromethane (2 mL). The reaction was initiated by the addition of 0.1 mL DI water. The reaction mixture was stirred at RT for the indicated times or until TLC or GC/MS showed consumption of the starting material and then filtered. After evaporation of the solvent using a rotavap, the crude reaction mixtures were separated via column chromatography to yield the desired ester dimers.

41%	With sodium bromate In tetrachloromethane at 35 - 37℃; for 2h;
35%	With [{Cu₂(L₄)-(μ-ClO₄)₂}(PF₆)₂]; dihydrogen peroxide; sodium acetate In water at 70℃; for 12h;
	With chromium(III) oxide; copper; zinc(II) oxide at 390℃;
	With cadmium containing zinc chromite at 390℃;
	With sodium chlorate; sulfuric acid; vanadia
	With potassium dichromate; sulfuric acid; water
	With uranium(VI) trioxide; copper(II) oxide at 200℃;
	With iodine In water
52 % Spectr.	With disodium hydrogenphosphate; benzyltrimethylammonium tribromide In tetrachloromethane; water at 60℃; for 5.5h;
35.1 % Turnov.	With oxygen; potassium carbonate at 80℃; for 5h;
	With oxygen at 80℃; for 5h;
	With {OsH(CO)[PyCH₂N(CH₂)2PiPr₂]2 at 96℃; for 8.5h; Inert atmosphere; Neat (no solvent);
71 %Chromat.	With potassium phosphate; oxygen In n-heptane at 90℃; for 24h; Schlenk technique; Green chemistry;
	With oxygen; potassium carbonate In n-heptane at 100℃; for 24h;
74 %Spectr.	With (bis[(2-diisopropylphosphino)ethyl]amine)Mn(CO)₂ at 110℃; for 72h; Inert atmosphere;
72 %Spectr.	With RuCl₂(PPh₃)[(EtSC₂H₄)2NH]; potassium <i>tert</i>-butylate In toluene at 110℃; for 24h; Inert atmosphere;
	With copper chromite unter Druck;
	With chromium(III) oxide; copper; zinc(II) oxide at 390℃;
	With cadmium containing zinc chromite at 390℃;
	With oxygen; Ag_0.03Au_0.97 at 149.84℃; Inert atmosphere;
81 %Chromat.	With potassium <i>tert</i>-butylate; C₂₈H₂₄Cl₂N₄Ru In dichloromethane; toluene Sealed tube; Reflux;

References: [1]Amati, Alessandro; Dosualdo, Gabriele; Zhao, Lihua; Bravo, Anna; Fontana, Francesca; Minisci, Francesco; Bjorsvik, Hans-Rene [Organic Process Research and Development, 1998, vol. 2, # 4, p. 261 - 269].
[2]Kumar, Sanjeev [Journal of the Indian Chemical Society, 2013, vol. 90, # 6, p. 739 - 744].
[3]Hackbusch, Sven; Franz, Andreas H. [Tetrahedron Letters, 2016, vol. 57, # 26, p. 2873 - 2876].
[4]Kajigaeshi, Shoji; Nakagawa, Takashi; Nagasaki, Noritaka; Yamasaki, Hiromochi; Fujisaki, Shizuo [Bulletin of the Chemical Society of Japan, 1986, vol. 59, # 3, p. 747 - 750].
[5]Huang, Da-Wei; Liu, Yi-Hung; Peng, Shie-Ming; Liu, Shiuh-Tzung [Organometallics, 2016, vol. 35, # 2, p. 151 - 158].
[6]Current Patent Assignee: EI DU PONT DE NEMOURS - US1857921, 1928, A.
[7]Current Patent Assignee: EI DU PONT DE NEMOURS - US1857921, 1928, A.
[8]Milas [Journal of the American Chemical Society, 1928, vol. 50, p. 496].
[9]Pierre; Puchot [Justus Liebigs Annalen der Chemie, 1872, vol. 163, p. 283][Annales de Chimie (Cachan, France), 1873, vol. <4>28, p. 366].
[10]Iwannikow; Gawrilowa [Zhurnal Prikladnoi Khimii, 1936, vol. 9, p. 491][Chemisches Zentralblatt, 1937, vol. 108, # I, p. 181] Iwannikow [Zhurnal Prikladnoi Khimii, 1947, vol. 17, p. 1103][Chem.Abstr., 1948, p. 1561] Iwannikow [Zhurnal Prikladnoi Khimii, 1940, vol. 13, p. 118][Chemisches Zentralblatt, 1940, vol. 111, # II, p. 2001].
[11]Kukushkin, Yu. N.; Demidov, V. N.; Fedyanin, N. P. [Journal of general chemistry of the USSR, 1983, vol. 53, # 10, p. 2159 - 2160][Zhurnal Obshchei Khimii, 1983, vol. 53, # 10, p. 2393 - 2394].
[12]Kajigaeshi, Shoji; Kawamukai, Hiroshi; Fujisaki, Shizuo [Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 8, p. 2585 - 2588].
[13]Zheng, Nanfeng; Stucky, Galen D. [Chemical Communications, 2007, # 37, p. 3862 - 3864].
[14]Su, Fang-Zheng; Ni, Ji; Sun, Hao; Cao, Yong; He, Yong; Fan, Kang-Nian [Chemistry - A European Journal, 2008, vol. 14, # 24, p. 7131 - 7135].
[15]Spasyuk, Denis; Smith, Samantha; Gusev, Dmitry G. [Angewandte Chemie - International Edition, 2012, vol. 51, # 11, p. 2772 - 2775].
[16]Jagadeesh, Rajenahally V.; Junge, Henrik; Pohl, Marga-Martina; Radnik, Joerg; Brueckner, Angelika; Beller, Matthias [Journal of the American Chemical Society, 2013, vol. 135, # 29, p. 10776 - 10782].
[17]Zhou, Yu-Xiao; Chen, Yu-Zhen; Cao, Lina; Lu, Junling; Jiang, Hai-Long [Chemical Communications, 2015, vol. 51, # 39, p. 8292 - 8295].
[18]Nguyen, Duc Hanh; Trivelli, Xavier; Capet, Frédéric; Paul, Jean-François; Dumeignil, Franck; Gauvin, Régis M. [ACS Catalysis, 2017, vol. 7, # 3, p. 2022 - 2032].
[19]Schörgenhumer, Johannes; Zimmermann, Axel; Waser, Mario [Organic Process Research and Development, 2018, vol. 22, # 7, p. 862 - 870].
[20]Current Patent Assignee: EI DU PONT DE NEMOURS - US2004350, 1931, A.
[21]Current Patent Assignee: EI DU PONT DE NEMOURS - DE597718, 1934, C [Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 21, p. 157].
[22]Current Patent Assignee: EI DU PONT DE NEMOURS - DE597718, 1934, C [Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 21, p. 157].
[23]Reece, Christian; Luneau, Mathilde; Friend, Cynthia M.; Madix, Robert J. [Angewandte Chemie - International Edition, 2020, vol. 59, # 27, p. 10864 - 10867][Angew. Chem., 2020, vol. 132, # 27, p. 10956 - 10959].
[24]Mukherjee, Aparajita; Datta, Sayanti; Richmond, Michael G.; Bhattacharya, Samaresh [RSC Advances, 2023, vol. 13, # 36, p. 25660 - 25672].

2
[ CAS Unavailable ]
[ 106-36-5 ]

Yield	Reaction Conditions	Operation in experiment
99%	With [{(PhN)MeC(N^t-Bu)}AlMe(μ-OMe)]₂ at 20℃; for 0.5h; Inert atmosphere; Schlenk technique; Green chemistry;	2.5 General procedure employed for the Tishchenko reaction General procedure: The pre-catalyst, amidinatoaluminum compound (0.8 mmol) was placed in a dry Schlenk flask under a nitrogen atmosphere, and freshly distilled aldehyde (80 mmol) was introduced. The mixture was immediately stirred at room temperature for 30 min to produce the corresponding ester. The reaction was quenched with 0.5 ml of water and the product was distilled to collect the corresponding ester. The yields reported are the isolated yield.
80%	With aluminum (III) chloride; triethylamine In dichloromethane at 20℃; for 48h;	General experimental methods for AlCl3-catalyzedCannizzaro/Tishchenko reactions General procedure: A mixture of AlCl3(0.5 mmol), the aldehyde (10 mmol),and triethylamine (5 mmol) was added to 2 cm3of driedCH2Cl2and stirred for 2 days at room temperature underargon atmosphere until the aldehyde was completelyconsumed. The reaction progress was probed by TLCand GC/MS (Agilent 6890 (GC)/5972A (MS)). The reactionmixture was then filtered through Whatman filterpaper (grade 2), and treated with sodium bicarbonatesolution, followed by isolating the organic phase via aseparatory funnel. The aqueous phase washed severaltimes with CH2Cl2to make sure that all organic materialsextracted. Then, the organic phase was dried usingsodium sulfate and subsequently analyzed by GC/MSand 1H NMR, and validated using melting or boilingpoint of the product.
	With aluminium propanolate

	With Mg-tetrakis(methoxy)borate; mercury dichloride In diethyl ether
	With Rh(PhBP₃)(H)2(NCMe) In benzene-d6 at 20℃; for 0.0166667h; Inert atmosphere;

References: [1]Zhang, Shaofeng; Han, Hongfei; Guo, Zhiqiang; Tong, Hongbo; Wei, Xuehong [Polyhedron, 2015, vol. 90, p. 118 - 122].
[2]Sharifi, Sina; Sharifi, Hannah; Koza, Darrell; Aminkhani, Ali [Monatshefte fur Chemie, 2021, vol. 152, # 7, p. 803 - 808].
[3]Tischtschenko [Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1906, vol. 38, p. 482][Chemisches Zentralblatt, 1906, vol. 77, # II, p. 1552].
[4]Hesse,G.; Maurer,M. [Justus Liebigs Annalen der Chemie, 1962, vol. 658, p. 21 - 38].
[5]Location in patent: experimental part Tejel, Cristina; Ciriano, Miguel A.; Passarelli, Vincenzo [Chemistry - A European Journal, 2011, vol. 17, # 1, p. 91 - 95].

3
[ 637-27-4 ]
[ 106-36-5 ]
[ CAS Unavailable ]
[ 6222-35-1 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
	at 250℃;

References: [1]McClellan; Connor [Journal of the American Chemical Society, 1941, vol. 63, p. 484,486].

4
[ CAS Unavailable ]
[ 106-36-5 ]
[ CAS Unavailable ]
[ 79-09-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 44.1% 2: 1.1% 3: 1%	With oxygen at 110℃;	6 EXAMPLE 6 EXAMPLE 6 In this example, n-propyl alcohol was reacted with oxygen over Pd on Zeolite Y catalyst. N-propyl propionate was obtained in good yield and with high selectivity.. Apparently, n-propyl alcohol reacts with oxygen in a way similar to ethanol to yield the corresponding ester, namely, n-propyl propionate. n-propyl alcohol conversion catalyzed by Pd on zeolite YCatalyst: Pd on Zeolite YTemperature, ° C.: 110WHSV, W/W/Hr.: 0.5Feed: n-propyl alcoholPressure, atm.: 2PRODUCTCOMPOSITIONn-propyl propionate (wt %)44.1n-propyl alcohol (wt %)33.5propionic acid (wt %)1.1n-propyl aldehyde (wt %)1.0H2O (wt %)13.3Fuel gas (wt %)5.6Total unidentified Species (wt %)1.4
	With dihydrogen peroxide In neat (no solvent) at 60℃;
	With sodium tungstophosphate; dihydrogen peroxide In neat (no solvent) at 60℃; for 8h; Green chemistry;

With dihydrogen peroxide In water at 70℃;

2.7.1. Oxidation of aliphatic alcohols General procedure: In general, the oxidation of aliphatic alcohols by hydrogen peroxidein the presence of catalyst Ps-Im-[VO(ap-Nt)] (6) as a representativecatalyst was carried out as follows. The representative substrate 1-butanol (0.81 g, 10.9 mmol) was reacted with 30% aqueous H2O2(6.18 g, 54.5 mmol) in the presence of 0.040 g of catalyst (6) at 70 Ctemperature for 5 h without any additional solvent. A small aliquot ofsample was withdrawn in a fixed time interval and analyzed by a gaschromatograph. All the supported catalysts were swelled in the respectivesubstrate for 6 h prior to use as a catalyst.

References: [1]Current Patent Assignee: CHANG JEN RAY - US6399812, 2002, B1 Location in patent: Page column 14.
[2]Kachhap, Payal; Chaudhary, Nikita; Haldar, Chanchal [Applied Organometallic Chemistry, 2021, vol. 35, # 12].
[3]Yu, Feng-Li; Liu, Min-Xue; Yuan, Bing; Xie, Cong-Xia; Yu, Shi-Tao [Catalysis Letters, 2023, vol. 153, # 6, p. 1738 - 1742].
[4]Kachhap, Payal; Chaudhary, Nikita; Haldar, Chanchal [Reactive and functional polymers, 2023, vol. 189].

5
[ 106-36-5 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
77%	With C₁₈H₂₈Br₂N₄Ru; potassium <i>tert</i>-butylate; hydrogen In 1,4-dioxane at 105℃; for 8h;	2.10. Typical procedure for the catalytic hydrogenation General procedure: To a mixture of catalyst (0.01 mmol), KOtBu (10 mol %), and 1,4-dioxane (4.0 mL) in a Parr high-pressure reactor was added the ester(1.0 mmol). The dark red solution was purged with H2 and stirred under 400 psi of H2 at 105 °C for 8 h. Products isolation were performed via column chromatography using silica gel as stationary phase and n-pentane/ethylacetate or n-pentane/isopropanol mixture as eluent. The products were confirmed by 1H NMR.
75 %Chromat.	Stage #1: propyl propionate With iron (II) stearate; ethylenediamine In toluene at 20℃; for 0.0833333h; Inert atmosphere; Schlenk technique; Stage #2: In toluene at 100℃; for 20h; Inert atmosphere; Schlenk technique;
68 %Chromat.	With [bis({2‐[bis(propan‐2‐yl)phosphanyl]ethyl})amine](borohydride)(carbonyl)(hydride)iron(II); hydrogen In tetrahydrofuran at 120℃; for 19h; Autoclave;

References: [1]Nirmala, Muthukumaran; Murugan, Kaliyappan; Vijayapritha, Subbarayan; Viswanathamurthi, Periasamy; Bertani, Roberta; Malecki, Jan Grzegorz [Inorganica Chimica Acta, 2019, vol. 486, p. 55 - 62].
[2]Junge, Kathrin; Wendt, Bianca; Zhou, Shaolin; Beller, Matthias [European Journal of Organic Chemistry, 2013, # 11, p. 2061 - 2065].
[3]Werkmeister, Svenja; Junge, Kathrin; Wendt, Bianca; Alberico, Elisabetta; Jiao, Haijun; Baumann, Wolfgang; Junge, Henrik; Gallou, Fabrice; Beller, Matthias [Angewandte Chemie - International Edition, 2014, vol. 53, # 33, p. 8722 - 8726][Angew. Chem., 2014, vol. 126, # 33, p. 8867 - 8871,5].

6
[ 110-91-8 ]
[ 106-36-5 ]
[ 30668-14-5 ]