Name: 616-39-7|N,N-Diethylmethylamine|98%
Brand: Ambeed
SKU: A723954
Price: 8.0 USD
Availability: InStock
Rating: 99 (28 reviews)

1
[ 617-84-5 ]
[ 616-39-7 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium aluminium tetrahydride; diethyl ether
	With hydrogen In 1,2-dimethoxyethane at 160℃; for 20h; Inert atmosphere; Autoclave; Molecular sieve;
99 %Spectr.	With 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In benzene-d6 at 60℃; for 4h; Glovebox; Schlenk technique; Inert atmosphere;

With La(CH2C6H4NMe2-o)3; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In benzene-d6 at 25℃; for 2h; Glovebox; Inert atmosphere;

Reference： [1]Blicke; Lu [Journal of the American Chemical Society, 1952, vol. 74, p. 3933]
[2]Stein, Mario; Breit, Bernhard [Angewandte Chemie - International Edition, 2013, vol. 52, # 8, p. 2231 - 2234]
[3]Guo, Chenjun; Zhang, Fangcao; Yu, Chong; Luo, Yunjie [Inorganic Chemistry, 2021, vol. 60, # 17, p. 13122 - 13135]
[4]Gong, Mingliang; Guo, Chenjun; Luo, Yunjie; Xie, Hongzhen; Zhang, Fangcao [New Journal of Chemistry, 2022, vol. 46, # 2, p. 779 - 791]

2
[ 616-39-7 ]
[ 88869-41-4 ]
[ 3166-62-9 ]

Reference： [1]Pharmaceutical Bulletin,1955,vol. 3,p. 417,420

3
[ 10052-47-8 ]
[ 74-87-3 ]
[ 75-00-3 ]
[ 616-39-7 ]
[ 121-44-8 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1876,vol. 181,p. 371

4
[ 75-52-5 ]
[ 75-07-0 ]
[ 616-39-7 ]

Yield	Reaction Conditions	Operation in experiment
	With platinum(IV) oxide; ethanol; acetic acid Hydrogenation;

Reference： [1]Emerson; Uraneck [Journal of the American Chemical Society, 1941, vol. 63, p. 750] Current Patent Assignee: Emerson - US2414031, 1945, A Current Patent Assignee: Emerson - US2380420, 1940, A Current Patent Assignee: Emerson - US23886068, 1944

5
[ 50-00-0 ]
[ 109-89-7 ]
[ 616-39-7 ]

Yield	Reaction Conditions	Operation in experiment
93%	at 120℃; for 8h;	1 Beispiel 1; Herstellung von N-Methyldiethylamin 149,3 g (2,0 mol) Diethylamin (98 %-ig) und 330,2 g (3,2 mol) Formaldehyd (29,1 %-ig) werden in einem 1l-Autoklav vorgelegt und auf 120C erwrmt. Die Reaktionszeit bei dieser Temperatur betrgt 8 Std., wobei sich ein Druck von max. 1,44 MPa einstellt. Danach wird das Reaktionsgemisch abgekhlt und destillativ aufgearbeitet. Dazu wird das Rohamin (wssrige und organische Phase) mit 200,0 g Isopropanol versetzt, in einen 1 l Kolben berfhrt und unter Rhren langsam auf 60C erwrmt. Dabei beginnt eine leichte Gasentwicklung, die beim Erreichen einer Temperatur von ca. 75C beendet ist. Danach wird unter Normaldruck vom Rckstand abdestilliert, es wird eine Destillatmenge von 614,4 g isoliert. Dieses Destillat wird zur Wasserabtrennung ber eine Membrane geleitet und anschlieend fraktioniert destilliert, das Amin siedet bei 63 - 65C. Es werden 168,8 g Wertprodukt mit einer Reinheit von 96,0 % isoliert, dies entspricht einer Ausbeute von 93,0 % d.Th
83%	With [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ In hexane; water at 50℃; for 5h;
80%	With acetic acid at 30℃; for 8h;

	With formic acid; water
	With formic acid Reflux;

Reference： [1]Current Patent Assignee: Oman Oil Company (in: Government of Oman); GOVERNMENT OF OMAN - EP1466887, 2004, A1 Location in patent: Page column 4
[2]van der Waals, Dominic; Heim, Leo. E.; Gedig, Christian; Herbrik, Fabian; Vallazza, Simona; Prechtl, Martin H. G. [ChemSusChem, 2016, vol. 9, # 17, p. 2343 - 2347]
[3]da Silva, Renato A.; Estevam, Idália H.S.; Bieber, Lothar W. [Tetrahedron Letters, 2007, vol. 48, # 43, p. 7680 - 7682]
[4]Spialter; Pappalardo [Journal of Organic Chemistry, 1957, vol. 22, p. 840,842] Hansson [Svensk Kemisk Tidskrift, 1955, vol. 67, p. 256,257]
[5]Location in patent: scheme or table Lukac, Milos; Mojzis, Jan; Mojzisova, Gabriela; Mrva, Martin; Ondriska, Frantisek; Valentova, Jindra; Lacko, Ivan; Bukovsky, Marian; Devinsky, Ferdinand; Karlovska, Janka [European Journal of Medicinal Chemistry, 2009, vol. 44, # 12, p. 4970 - 4977]

6
[ 616-39-7 ]
[ 109-64-8 ]
[ 117961-65-6 ]

Yield	Reaction Conditions	Operation in experiment
	With benzene

Reference： [1]Gray et al. [Journal of the American Chemical Society, 1955, vol. 77, p. 3648] Current Patent Assignee: IRWIN NEISLER - US2817664, 1954, A

7
[ 616-39-7 ]
[ 74-88-4 ]
[ 4325-24-0 ]

Yield	Reaction Conditions	Operation in experiment
83%	In butanone at 20℃;

Reference： [1]Wempe [Journal of Molecular Structure, 2001, vol. 562, # 1-3, p. 63 - 78]
[2]Huenig; Baron [Chemische Berichte, 1957, vol. 90, p. 395,397,398]

8
[ 617-86-7 ]
[ 102-53-4 ]
[ 616-39-7 ]
[ 6022-10-2 ]

Yield	Reaction Conditions	Operation in experiment
97%	With nickel at 140 - 150℃;

Reference： [1]Gal'tseva, T. D.; Mel'nitskii, I. A.; Kiladze, T. K.; Kantor, E. A.; Rakhmankulov, D. L. [Journal of general chemistry of the USSR, 1987, vol. 57, p. 1490][Zhurnal Obshchei Khimii, 1987, vol. 57, p. 1671]

9
[ 1217-45-4 ]
[ 616-39-7 ]
[ 1210-12-4 ]
[ 1467-01-2 ]
[ 14789-44-7 ]
[ 23353-77-7 ]

Reference： [1]Journal of Organic Chemistry,1988,vol. 53,p. 5435 - 5442

10
[ 616-39-7 ]
[ 6608-47-5 ]
[ 51211-54-2 ]
[ 27919-20-6 ]
Ethenesulfonic acid; compound with diethyl-methyl-amine [ No CAS ]

Reference： [1]Canadian Journal of Chemistry,1984,vol. 62,p. 1977 - 1995

11
[ 616-39-7 ]
[ 107-36-8 ]
[ 27919-20-6 ]

Reference： [1]Canadian Journal of Chemistry,1984,vol. 62,p. 1977 - 1995

12
[ 616-39-7 ]
[ 16486-97-8 ]
[ 307-22-2 ]
[ 108836-15-3 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In hexane at 60℃; for 0.5h;

Reference： [1]Huang, Yao-Zeng; Shou, Qi-Lin [Journal of Organic Chemistry, 1987, vol. 52, # 16, p. 3552 - 3558]

13
[ 616-39-7 ]
Diethyl-methyl-amine; compound with trifluoroborane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With boron trifluoride In chloroform-d1 at -50℃;

Reference： [1]Fox, Arnold; Hartman, Stephen J.; Humphries, Robyn E. [Journal of the Chemical Society, Dalton Transactions, 1982, p. 1275 - 1284]

14
[ 616-39-7 ]
Diethyl-methyl-amine; compound with trichloroborane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With boron trichloride In chloroform-d1 at -50℃;

Reference： [1]Fox, Arnold; Hartman, Stephen J.; Humphries, Robyn E. [Journal of the Chemical Society, Dalton Transactions, 1982, p. 1275 - 1284]

15
[ 616-39-7 ]
Diethyl-methyl-amine; compound with GENERIC INORGANIC NEUTRAL COMPONENT [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With boron trifluoride; boron trichloride In chloroform-d1 at -50℃;

Reference： [1]Fox, Arnold; Hartman, Stephen J.; Humphries, Robyn E. [Journal of the Chemical Society, Dalton Transactions, 1982, p. 1275 - 1284]

16
[ 616-39-7 ]
Diethyl-methyl-amine; compound with GENERIC INORGANIC NEUTRAL COMPONENT [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With boron trifluoride; boron trichloride In chloroform-d1 at -50℃;

Reference： [1]Fox, Arnold; Hartman, Stephen J.; Humphries, Robyn E. [Journal of the Chemical Society, Dalton Transactions, 1982, p. 1275 - 1284]

17
[ 616-39-7 ]
[ 74-95-3 ]
[ 104303-94-8 ]

Yield	Reaction Conditions	Operation in experiment
87%	In acetonitrile at 30℃; for 51h;

Reference： [1]Almarzoqi, B.; George, A. V.; Isaacs, N. S. [Tetrahedron, 1986, vol. 42, # 2, p. 601 - 608]

18
[ 616-39-7 ]
[ 146758-36-3 ]
N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-N',N'-diethylacetamidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With mercury(II) oxide In dichloromethane for 120h; Ambient temperature;

Reference： [1]Avalos, Martin; Babiano, Reyes; Cintas, Pedro; Duran, Carlos J.; Jimenez, Jose L.; Palacios, Juan C. [Tetrahedron, 1995, vol. 51, # 29, p. 8043 - 8056]

19
[ 616-39-7 ]
[ 612-23-7 ]
Diethyl-methyl-(2-nitro-benzyl)-ammonium; chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	In acetonitrile for 6h; Heating;

Reference： [1]Tercel, Moana; Wilson, William R.; Anderson, Robert F.; Denny, William A. [Journal of Medicinal Chemistry, 1996, vol. 39, # 5, p. 1084 - 1094]

20
[ 75-11-6 ]
[ 616-39-7 ]
1-iodo-N,N-diethyl-N-methylmethaniminium iodide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
9.2%	With hydroquinone In ethyl acetate at 20℃; for 18h;

Reference： [1]Fletcher, Michelle O.; Zhang, Li; Vu, Quyen; Dolbier Jr., William R. [Journal of the Chemical Society. Perkin Transactions 2 (2001), 1999, # 6, p. 1187 - 1192]

21
[ 616-39-7 ]
(6aS-trans)-9-bromoacetoxymethyl-6,6-dimethyl-3-(1,1-dimethylheptyl)-1-hydroxy-6a,7,10,10a-tetrahydro-6H-dibenzo[b,d]pyran [ No CAS ]
(6aS-trans)-6,6-dimethyl-3-(1,1-dimethylheptyl)-1-hydroxy-9-(N-methyl-N-ethylammonioacetoxymethyl)-6a,7,10,10a-tetrahydro-6H-dibenzo[b,d]pyran bromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	In diethyl ether at -5 - 22℃; for 336000h;

Reference： [1]Pop, Emil; Rachwal, Stanislaw; Vlasak, Jirina; Biegon, Anat; Zharikova, Alevtina; Prokai, Laszlo [Journal of Pharmaceutical Sciences, 1999, vol. 88, # 11, p. 1156 - 1160]

Yield	Reaction Conditions	Operation in experiment
	With water durch Destillation bei bei Atmosphaerendruck, in geringerer Ausbeute beim Eindampfen im Vakuum bei Zimmertemperatur;

23
[ 7664-41-7 ]
[ 10052-47-8 ]
potassium [ No CAS ]
[ 34557-54-5 ]
[ 74-85-1 ]
[ 616-39-7 ]
[ 121-44-8 ]

Reference： [1]Journal of the Chemical Society,1956,p. 4653,4655

24
[ 616-39-7 ]
[ 15214-89-8 ]
C₁₂H₂₆N₂O₄S [ No CAS ]

Reference： [1]Russian Journal of Organic Chemistry,2000,vol. 36,p. 343 - 349

25
[ 616-39-7 ]
[ 107-08-4 ]
[ 44797-85-5 ]

Yield	Reaction Conditions	Operation in experiment
78%	In butanone for 0.666667h; Heating;

Reference： [1]Wempe [Journal of Molecular Structure, 2001, vol. 562, # 1-3, p. 63 - 78]

26
[ 616-39-7 ]
[4,4,6-Trimethyl-7-oxa-bicyclo[4.1.0]hept-(2E)-ylidene]-acetonitrile [ No CAS ]
(3-hydroxy-3,5,5-trimethylcyclohex-1-enyl)acetonitrile [ No CAS ]
2-(3-hydroxy-3,5,5-trimethylcyclohex-1-enyl)acrylonitrile [ No CAS ]
2-(3-hydroxy-3,5,5-trimethylcyclohex-1-enyl)isocrotononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 22% 2: 13% 3: 20%	Stage #1: N,N-diethylnmethylamine; [4,4,6-Trimethyl-7-oxa-bicyclo[4.1.0]hept-(2E)-ylidene]-acetonitrile In acetonitrile at 20℃; for 5h; Irradiation; Stage #2: With silica gel In chloroform at 20℃; for 2h;

Reference： [1]Ishii, Keitaro; Hakamada, Satoshi; Nagano, Mayumi; Noji, Masahiro; Sugiyama, Shigeo; Kotera, Masashi; Sakamoto, Masanori [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2002, # 13, p. 1592 - 1598]

27
[ 616-39-7 ]
[ 15008-33-0 ]
C₁₃H₃₂N₂⁽²⁺⁾*2Br^(1-) [ No CAS ]

Reference： [1]Russian Journal of Bioorganic Chemistry,2002,vol. 28,p. 116 - 127

28
[ 109-89-7 ]
[ 74-88-4 ]
[ 616-39-7 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: diethylamine With poly(ethylene glycol)-bound acrylate In N,N-dimethyl-formamide at 20℃; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 15h; Stage #3: With weak basic resin In dichloromethane at 20℃; for 18h;

Reference： [1]Chen, Zuxing; Yang, Guichun; Zhang, Zhaojun [Synthetic Communications, 2003, vol. 33, # 5, p. 729 - 734]

29
[ 616-39-7 ]
[ 6482-24-2 ]
N,N-diethyl-N-(2-methoxyethyl)-N-methyl-ammonium bromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	In acetone at 100℃; for 12h;
	In acetone
	In toluene at 27 - 70℃; for 45h;	9 Comparative Example 9; Preparation of N,N-diethyl-N-methoxyethyl-N-methylammonium tetrafluoroborate; Diethylmethylamine (35.53 g, reagent, product of Tokyo Kasei Co., Ltd.) was dissolved in 161.37 g of toluene, followed by replacement with nitrogen. To the solution was added dropwise 68.00 g of bromoethyl methyl ether (reagent, product of Aldrich Corp.) at 27°C over a period of 1 hour. The mixture was heated to a gradually raised temperature and then stirred at 60 to 70°C for 44 hours to terminate the reaction. The reaction mixture was cooled to room temperature, and the resulting solids were filtered off in nitrogen. The filter cake was washed with 70 g of toluene and thereafter dried in a vacuum (giving 67.30 g of a brown solid product). The product, which was markedly colored, was dissolved in 131.52 g of water, 7.02 g of activated carbon (Carboraffin, product of Takeda Pharmaceutical Co., Ltd.) was added to the solution, and the mixture was stirred at 90 to 95°C for 12 hours. The mixture was cooled to room temperature, and the activated carbon was separated off by filtration. The filtrate was concentrated in a vacuum, followed by drying in a vacuum to result in a yield of 58.34 g. The product was dissolved in a solvent mixture of 200.48 g of acetone and 27.22 g of chloroform with heating for recrystallization. The white solids obtained were filtered off in a nitrogen stream, washed with 50 g of acetone and dried in a vacuum, giving 47.58 g of the desired product (N,N-diethyl-N-methoxyethyl-N-methylammonium bromide). 1H-NMR (CD3OD) δ ppm: 1.35 (m 6H), 3.07 (s 3H), 3.39 (s 3H), 3.40~3.57(m 6H), 3.80(m 2H).

In water

Reference： [1]Zhou, Zhi-Bin; Matsumoto, Hajime; Tatsumi, Kuniaki [Chemistry - A European Journal, 2005, vol. 11, # 2, p. 752 - 766]
[2]Zhou, Zhi-Bin; Matsumoto, Hajime; Tatsumi, Kuniaki [Chemistry Letters, 2004, vol. 33, # 7, p. 886 - 887]
[3]Current Patent Assignee: OTSUKA HOLDINGS CO LTD; STELLA CHEMIFA CORPORATION - EP1642894, 2006, A1 Location in patent: Page/Page column 19
[4]Location in patent: body text Yoshida, Yukihiro; Saito, Gunzi [Physical Chemistry Chemical Physics, 2011, vol. 13, # 45, p. 20302 - 20310]

30
[ 109-65-9 ]
[ 616-39-7 ]
N-(n-butyl)-N,N-diethyl-N-methylammonium bromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	In acetone at 100℃; for 12h;
	In acetonitrile at 64.84 - 69.84℃; for 6h; Inert atmosphere;	SI2-1-1. Butyldiethylmethylammanium bis(trifluoromethylsulfonyl)amide, [N1224][NTf2]. Butyldiethylammonium bromide ([N1224]Br) was synthesized as a precursor for [N1224][NTf2].Diethylmethylamine was distilled before use. 1-Bromobutane (21.5 g, 157 mmol) was added to anacetonitrile solution of 1-methylpyrrolidine (6.52 g, 97.8 mmol) at nitrogen atmosphere in a flask equippedwith a reflux condenser and a magnetic stirrer. The solution was heated to 338-343 K in an oil bath for 6hours while stirring. The solution was allowed to cool to room temperature and evaporated. The obtainedsolid was recrystallized from THF and acetonitrile, and then dried in vacuo at 313 K for more than 2 days.Then, a part of the [N1224]Br (4.52 g, 20.2 mmol) was dissolved in water and aqueous solution of lithiumbis(trifluoromethylsulfonyl)amide (6.33 g, 22.0 mmol) was added. After the mixture was stirred at roomtemperature for 15 hours, the aqueous layer was decanted. The ionic liquid layer was dissolved indichloromethane and washed with water five times. The dichloromethane was then evaporated. The ionicliquid was mixed with activated charcoal in acetonitrile and stirred at room temperature overnight. Thesolution was filtered and evaporated. The ionic liquid was finally dried in vacuo at 313 K for more than 2days. The yield of the anion exchange was 97.1%.

Reference： [1]Zhou, Zhi-Bin; Matsumoto, Hajime; Tatsumi, Kuniaki [Chemistry - A European Journal, 2005, vol. 11, # 2, p. 752 - 766]
[2]Shirota, Hideaki; Ando, Masatoshi; Kakinuma, Shohei; Takahashi, Kotaro [Bulletin of the Chemical Society of Japan, 2020, vol. 93, # 12, p. 1520 - 1539]

31
[ 616-39-7 ]
[ 106-94-5 ]
N,N-diethyl-N-methyl-N-(n-propyl)ammonium bromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	In acetone at 100℃; for 12h;

Reference： [1]Zhou, Zhi-Bin; Matsumoto, Hajime; Tatsumi, Kuniaki [Chemistry - A European Journal, 2005, vol. 11, # 2, p. 752 - 766]

32
[ 616-39-7 ]
[ 143-15-7 ]
[ 94036-11-0 ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol Reflux;	2.2. Synthesis and characterization of surfactants General procedure: DTMABr and DDMEABr are commercially available surfactant molecules.Dodecylammonuim bromide (DABr), dodecylmethylammoniumbromide (DMABr), dodecyldimethylammonium bromide (DDMABr)were obtained fromthe reaction of dodecylamine,N-methyldodecylamineand N,N-dimethyldodecylamine, respectively, with HBr(aq). Diethylmethylamineand triethylaminewere reacted with 1-bromododecane forthe preparation of dodecyldiethylmethylammoniumbromide (DDEMABr)and dodecyltriethylammonium bromide (DTEABr) as follows. A two-foldmolar excess of the alkylaminewasmixed with 1-bromododecane in ethanolandrefluxed. The progress of the reactionswasmonitored by thin-layerchromatography carried out on 0.25mmsilica gel plates (60F-254) usingUV light as visualizing agent, and KMnO4 solution and heat as developingagents. After the reactionwas completed, a yellowtwo-phase mixturewasobtained. This mixturewas concentrated by rotary evaporation. After precipitationby ether and subsequent filtration a solid residuewas obtained.Sometimes the mixture had to be chilled to obtain precipitation. This solidresidue was then purified by recrystallization fromchloroform-ether, andsubsequent filtration followed by drying under vacuum resulted in surfactantsas white solids. All dodecylalkylammonium bromide surfactants,DAABr, (synthesized and purchased ones, Fig. 1)were characterized by 1Hnuclear magnetic resonance (1H NMR) and Fourier transform infrared(FTIR) spectroscopy techniques. 1H NMR spectrawere recorded on JEOLNMR spectrometer (400 MHz) at ambient temperature. All chemicalshifts (δ) are reported in part permillion (ppm) downfield fromTMS. Theabbreviations used forNMRsignals are: s=singlet, t=triplet, q=quartet,m=multiplet,brs=broadsinglet,brm=broadmultiplet.Infraredspectrawere recorded on a Shimadzu IR prestige-21 FTIR. TheNMRresults, includingcommercially available ones for the comparison, are given in thefollowing.

Reference： [1]Yin, Haiqing; Huang, Jianbin; Lin, Yiyang; Zhang, Yongyi; Qiu, Shunchen; Ye, Jianping [Journal of Physical Chemistry B, 2005, vol. 109, # 9, p. 4104 - 4110]
[2]Akpinar, Erol; Uygur, Nazli; Ordu, Oznur Demir; Reis, Dennys; Neto, Antônio Martins Figueiredo [Journal of Molecular Liquids, 2021, vol. 332]

33
[ 616-39-7 ]
[ 97-94-9 ]
[ 103-71-9 ]
2-(ethylmethylamino)-N-phenylpropanamide [ No CAS ]
[ 101-99-5 ]
[ 3213-15-8 ]
[ 102-07-8 ]

Yield	Reaction Conditions	Operation in experiment
1: 63% 2: 13% 3: 5% 4: 6%	With oxygen at 20℃; for 10h;

Reference： [1]Yoshimitsu, Takehiko; Matsuda, Kenichi; Nagaoka, Hiroto; Tsukamoto, Koji; Tanaka, Tetsuaki [Organic Letters, 2007, vol. 9, # 24, p. 5115 - 5118]

34
[ 616-39-7 ]
C₁₆H₃₄NO⁽¹⁺⁾*BF₄^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: hexane / 0.5 h / 20 °C 2: 99 percent / aq. NaBF₄ / 2 h / 20 °C

Reference： [1]Pernak, Juliusz; Feder-Kubis, Joanna [Chemistry - A European Journal, 2005, vol. 11, # 15, p. 4441 - 4449]

35
[ 616-39-7 ]
N,N-diethyl-N-methyl-N-(n-propyl)ammonium hydroxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 80 percent / acetone / 12 h / 100 °C / 45003.6 Torr 2: basic anion-exchange resin / H₂O

Reference： [1]Zhou, Zhi-Bin; Matsumoto, Hajime; Tatsumi, Kuniaki [Chemistry - A European Journal, 2005, vol. 11, # 2, p. 752 - 766]

36
[ 616-39-7 ]
N-(n-butyl)-N,N-diethyl-N-methylammonium bis(trifluoromethanesulfonyl)imide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 80 percent / acetone / 12 h / 100 °C / 45003.6 Torr 2: basic anion-exchange resin / H₂O 3: H₂O
	Multi-step reaction with 2 steps 1: acetonitrile / 6 h / 64.84 - 69.84 °C / Inert atmosphere 2: water / 15 h / 20 °C

Reference： [1]Zhou, Zhi-Bin; Matsumoto, Hajime; Tatsumi, Kuniaki [Chemistry - A European Journal, 2005, vol. 11, # 2, p. 752 - 766]
[2]Shirota, Hideaki; Ando, Masatoshi; Kakinuma, Shohei; Takahashi, Kotaro [Bulletin of the Chemical Society of Japan, 2020, vol. 93, # 12, p. 1520 - 1539]

37
[ 616-39-7 ]
N,N-diethyl-N-methyl-N-(2-methoxyethyl)ammonium bis(trifluoromethanesulfonyl)imide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 76 percent / acetone / 12 h / 100 °C / 45003.6 Torr 2: basic anion-exchange resin / H₂O 3: H₂O
	Multi-step reaction with 2 steps 1: water 2: water / 48 h / 20 °C / Darkness

Reference： [1]Zhou, Zhi-Bin; Matsumoto, Hajime; Tatsumi, Kuniaki [Chemistry - A European Journal, 2005, vol. 11, # 2, p. 752 - 766]
[2]Yoshida, Yukihiro; Saito, Gunzi [Physical Chemistry Chemical Physics, 2011, vol. 13, # 45, p. 20302 - 20310]

38
[ 616-39-7 ]
N,N-diethyl-N-(2-methoxyethyl)-N-methyl-ammonium hydroxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 76 percent / acetone / 12 h / 100 °C / 45003.6 Torr 2: basic anion-exchange resin / H₂O
	Multi-step reaction with 2 steps 1: acetone 2: anion exchange

Reference： [1]Zhou, Zhi-Bin; Matsumoto, Hajime; Tatsumi, Kuniaki [Chemistry - A European Journal, 2005, vol. 11, # 2, p. 752 - 766]
[2]Zhou, Zhi-Bin; Matsumoto, Hajime; Tatsumi, Kuniaki [Chemistry Letters, 2004, vol. 33, # 7, p. 886 - 887]

39
[ 616-39-7 ]
N,N-diethyl-N-methyl-N-(2-methoxyethyl)ammonium tetrafluoroborate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 76 percent / acetone / 12 h / 100 °C / 45003.6 Torr 2: basic anion-exchange resin / H₂O 3: H[BF₄] / H₂O
	Multi-step reaction with 2 steps 1: acetone 2: 90 percent / aq. HBF₄

Reference： [1]Zhou, Zhi-Bin; Matsumoto, Hajime; Tatsumi, Kuniaki [Chemistry - A European Journal, 2005, vol. 11, # 2, p. 752 - 766]
[2]Zhou, Zhi-Bin; Matsumoto, Hajime; Tatsumi, Kuniaki [Chemistry Letters, 2004, vol. 33, # 7, p. 886 - 887]

40
[ 616-39-7 ]
N,N-diethyl-N-methyl-N-(2-methoxyethyl)ammonium pentafluoroethyltrifluoroborate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 76 percent / acetone / 12 h / 100 °C / 45003.6 Torr 2: basic anion-exchange resin / H₂O 3: H₂O
	Multi-step reaction with 2 steps 1: acetone 2: 87 percent / anion exchange

Reference： [1]Zhou, Zhi-Bin; Matsumoto, Hajime; Tatsumi, Kuniaki [Chemistry - A European Journal, 2005, vol. 11, # 2, p. 752 - 766]
[2]Zhou, Zhi-Bin; Matsumoto, Hajime; Tatsumi, Kuniaki [Chemistry Letters, 2004, vol. 33, # 7, p. 886 - 887]

41
[ 616-39-7 ]
[ 107-14-2 ]
cyanomethyl-diethyl-methylammonium chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	In acetone at 20℃;

Reference： [1]Current Patent Assignee: CLARIANT AG - WO2006/24434, 2006, A1 Location in patent: Page/Page column 22

42
[ 616-39-7 ]
[ 627-42-9 ]
[ 934843-20-6 ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile; for 12 - 72h;Heating / reflux; Autoclave;	An amine (diethylmethylamine) and an equimolar amount of a halogen-substituted ether compound (methoxyethylchloride) as starting materials were mixed in acetonitrile, and then the mixture was reacted for 12 to 72 hours by heating in an autoclave under mild conditions. After the reaction, the quaternary ammonium salt product was recrystallized in an appropriate solvent, and the formation of diethylmethylmethoxyethylammonium chloride (N102122+Cl-) was confirmed by NMR. The halide thus obtained was converted to the hydroxide (N102122+OH-) with an anion exchange resin.

Reference： [1]Patent: EP1698631,2006,A1 .Location in patent: Page/Page column 6

43
[ 127-19-5 ]
[ 598-56-1 ]
[ 624-78-2 ]
[ 616-39-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen; dimethyl amine at 250℃;	3 EXAMPLE 3In a fixed bed reactor containing 5 g of catalyst (Cu0203 Engelhard) a mixture of N,N-dimethylacetamide, DMA and H2 is introduced. The mixture with a molar composition of amide/auxiliary amine/H2 of 1/3/30 is preheated and introduced continuously at the catalyst bed at a rate of 2 g amide/h. The reactor is heated at 250 ° C. and operated at 10 bars. At the outlet, the product containing the desired amine is analysed with GC on-line. The product composition (area %) is displayed in table 3
1: 96.1 %Chromat. 2: 2.8 %Chromat. 3: 0.8 %Chromat.	With hydrogen; dimethyl amine at 250℃; Gas phase;	3 Example 3: In a fixed bed reactor containing 5 g of catalyst (Cu0203 Engelhard) a mixture of N,N-dimethylacetamide, DMA and H2 is introduced. The mixture with a molar composition of amide/auxiliary amine/H2 of 1/3/30 is preheated and introduced continuously at the catalyst bed at a rate of 2 g amide/h. The reactor is heated at 25CO and operated at 10 bars. At the outlet, the product containing the desired amine is analysed with GC on-line. The product composition (area%) is displayed in table 3.

Reference： [1]Current Patent Assignee: EASTMAN CHEMICAL CO - US2006/287556, 2006, A1 Location in patent: Page/Page column 5
[2]Current Patent Assignee: EASTMAN CHEMICAL CO - WO2006/136204, 2006, A1 Location in patent: Page/Page column 13

44
[ 616-39-7 ]
[ 104-15-4 ]
[ 107-14-2 ]
cyanomethyl-diethyl-methylammonium tosylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	Stage #1: N,N-diethylnmethylamine; chloroacetonitrile In toluene at 50 - 60℃; for 3h; Stage #2: toluene-4-sulfonic acid In toluene at 5 - 25℃; for 4h; Heating / reflux;	2 Synthesis of (cyanomethyl)diethylmethylammonium Tosylate 87.2 g (1 mol) of diethylmethylamine were initially charged at 50° C. in 1000 ml of toluene, and 75.5 g (1 mol) of chloroacetonitrile were added. The reaction mixture was stirred at 60° C. for 3 hours. Then 172.2 g of anhydrous toluenesulfonic acid dissolved in 600 ml of toluene were added at 25° C. and the reaction mixture was stirred under reflux for 4 hours, in the course of which evolution of gas was observed. The reaction mixture was cooled slowly to 5° C., and the precipitated solid was filtered, washed twice with 100 ml each time of toluene and dried at 60° C. under reduced pressure.245.9 g (0.82 mol) of (cyanomethyl)diethylmethylammonium tosylate were obtained as a colorless solid, corresponding to a yield of 82%.1H NMR (D2O): δ=7.70 (2H, d); δ=7.36 (2H, d); δ=4.62 (2H, s); δ=3.54 (4H, q); δ=3.17 (3H, s); δ=2.39 (3H, s); δ=1.37 (6H, t).

Reference： [1]Current Patent Assignee: CLARIANT AG - US2009/171111, 2009, A1 Location in patent: Page/Page column 3

45
[ 616-39-7 ]
[ 107-14-2 ]
[ 80-48-8 ]
cyanomethyl-diethyl-methylammonium tosylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	Stage #1: N,N-diethylnmethylamine; chloroacetonitrile In ethyl acetate at 50 - 60℃; for 4h; Stage #2: methyl p-toluene sulfonate In ethyl acetate for 1h; Heating / reflux;	1 Synthesis of (cyanomethyl)diethylmethylammonium Tosylate Example 1 Synthesis of (cyanomethyl)diethylmethylammonium Tosylate 43.59 g (0.5 mol) of diethylmethylamine were initially charged at 50° C. in 500 ml of ethyl acetate, and 37.75 g (0.5 mol) of chloroacetonitrile were added. The reaction mixture was stirred at 60° C. for 4 hours. Then 93.12 g (0.5 mol) of methyl para-toluenesulfonate are added and the reaction mixture stirred under reflux for 60 minutes, in the course of which vigorous evolution of gas was observed. The reaction mixture was cooled slowly to 5° C., and the precipitated solid was washed twice with 50 ml each time of ethyl acetate and dried at 60° C. under reduced pressure. 143.3 g (0.48 mol) of (cyanomethyl)diethylmethylammonium tosylate were obtained as a colorless solid, corresponding to a yield of 96%. 1H NMR (D2O): δ=7.70 (2H, d); δ=7.36 (2H, d); δ=4.62 (2H, s); δ=3.54 (4H, q); δ=3.17 (3H, s); δ=2.39 (3H, s); δ=1.37 (6H, t).

Reference： [1]Current Patent Assignee: CLARIANT AG - US2009/149668, 2009, A1 Location in patent: Page/Page column 3

46
[ 941-55-9 ]
[ 616-39-7 ]
[ 1209499-72-8 ]
[ 29397-20-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 46% 2: 15%	With tetrachloromethane; copper(l) chloride at 20 - 25℃; for 8h; Inert atmosphere;

Reference： [1]Xu, Xiaoliang; Ge, Zhichuang; Cheng, Dongping; Lei, Ma.; Lu, Chunshan; Zhang, Qunfeng; Yao, Nan; Li, Xiaonian [Organic Letters, 2010, vol. 12, # 5, p. 897 - 899]

47
[ 616-39-7 ]
[ 1242440-50-1 ]
[ 1242440-54-5 ]

Yield	Reaction Conditions	Operation in experiment
90.5%	In toluene at 75 - 83℃; for 48h;	34 A mixture of the (Br-EtO)-Ad- Ph-OEt EE 29 (512.7 mg, 1.2 mmole) and diethylmethylamine (0.75 ml, 6.1 mmole, 5 equiv.) in 5 ml of toluene was placed in a sealed pressure tube. No reaction was detected by TLC after 71 hours of stirring at room temperature. An additional 1.5 ml of diethylmethylamine (12.2 mmole, 10 equiv.) was added, the reaction vessel was heated in an oil bath at 75-83°C for 48 hours. TLC showed that nearly all of the starting material was converted to the polar product. The reaction mixture was concentrated and purified by silica gel chromatography, eluting with 0-10% MeOH in CH2Cl2, to give 560 mg(90.5%) of the product 12a as an orange gum.IR (CHCl3): 3620, 3380, 2992, 2932, 2858, 1597, 1578, 1430-1478, 1286, 1240, 1177,1100, 1015, 975 cm"1.1H NMR (400 MHz, CDCl3): δ 7.22-7.33 (m, IH), 6.80-6.90 (m, 3H), 4.01-4.09 (m, 2H),3.81-3.93 (m, 4H), 3.60-3.75 (m, 3 or 4H?), 3.48 (br. s, 3H?), 3.27-3.35 (m, 5H?), 2.83(br. s, IH), 2.29 (br. s, IH), 1.59-1.91 (m, 10H), 1.35-1.48 (m, 9H). Due to the complexity of the spectrum, and the presence of impurities, the integrals of some superimposed peaks cannot be definitively assigned.

Reference： [1]Current Patent Assignee: THERMO FISHER SCIENTIFIC INC - WO2010/101839, 2010, A2 Location in patent: Page/Page column 41-42

48
[ 616-39-7 ]
[ 1242440-51-2 ]
[ 1242440-55-6 ]

Yield	Reaction Conditions	Operation in experiment
54.2%	In toluene at 82℃; for 95h;	35 A mixture of the (Br-EtO)-Ad- Ph- OEOM EE 30 (483.4 mg, 1.1 mmole) and diethylmethylamine (1.3 ml, 11 mmole, 10 equiv.) in 5 ml of toluene in a sealed pressure tube was heated at ~82°C for 95 hours. The reaction mixture was concentrated and purified by silica gel chromatography, eluting with 5-20% MeOH in CH2Cl2, to give 312.5 mg (54.2%) of the product 13a as a light yellow gum.IR (CHCl3): 3680, 3380, 2930, 2858, 1600, 1580, 1460, 1393, 1236, 1160, 1 100, 1080, 1019, 976 cm 1.1H NMR (400 MHz, CDCl3): δ 7.25-7.29 (m, IH), 6.98-7.04 (m, IH), 6.95-6.99 (m, IH), 6.91-6.96 (m, IH), 5.24 (s, 2H), 3.81-3.93 (m, 4H), 3.75 (q, J=7 Hz), 3.61-3.72 (m, 4H), 3.48 (br. s, IH), 3.31 (s, 3H), 3.30 (s, 3H), 2.85 (br. s, IH), 2.29 (br. s, IH), 1.59-1.91 (m, 10H), 1.40 (t, J=7 Hz, 6H), 1.23 (t, J=7 Hz, 3H).

Reference： [1]Current Patent Assignee: THERMO FISHER SCIENTIFIC INC - WO2010/101839, 2010, A2 Location in patent: Page/Page column 42

49
[ 75-07-0 ]
[ 74-89-5 ]
[ 624-78-2 ]
[ 616-39-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen; sodium hydroxide at 65 - 67℃; for 4.3h; Autoclave; Industry scale;	2 Example 2 ComparativeThe reaction for the synthesis of EMA is carried out according to Example 1 above, with an amount of sodium hydroxide of only 0.05 mol % relative to the anhydrous MMA introduced.The N-ethylmethylamine is obtained in the crude reaction medium with a selectivity, with respect to the acetaldehyde, of only 67.6 mol %, due to the formation of a large amount of DEMA (17.2% selectivity with respect to acetaldehyde), and of heavy compounds (13% selectivity with respect to acetaldehyde).

Reference： [1]Current Patent Assignee: ARKEMA - US2011/166387, 2011, A1 Location in patent: Page/Page column 3-4

50
[ 616-39-7 ]
[ 94-02-0 ]
[ 21299-15-0 ]
[ 351031-95-3 ]

Yield	Reaction Conditions	Operation in experiment
1: 12% 2: 30%	With tert.-butylhydroperoxide; diiron nonacarbonyl In decane at 25℃; for 0.166667h; Inert atmosphere;

Reference： [1]Liu, Weiping; Liu, Jinhua; Ogawa, Daisuke; Nishihara, Yasushi; Guo, Xingwei; Li, Zhiping [Organic Letters, 2011, vol. 13, # 23, p. 6272 - 6275]

51
[ 3140-73-6 ]
[ 616-39-7 ]
[ 1421852-16-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	In tetrahydrofuran at 20℃; for 1h;

Reference： [1]Kunishima, Munetaka; Ujigawa, Takae; Nagaoka, Yoshie; Kawachi, Chiho; Hioki, Kazuhito; Shiro, Motoo [Chemistry - A European Journal, 2012, vol. 18, # 49, p. 15856 - 15867]

52
[ 616-39-7 ]
[ 1493-13-6 ]
[ 945715-39-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	In water at 20℃;
98.5%	In water for 1h; Cooling with ice;
	In neat (no solvent)

In water

Reference： [1]Merkel, Nina C.; Roemich, Christiane; Bernewitz, Richard; Kuenemund, Hannes; Gleiss, Marco; Sauer, Sven; Schubert, Thomas J. S.; Guthausen, Gisela; Schaber, Karlheinz [Journal of Chemical and Engineering Data, 2014, vol. 59, # 3, p. 560 - 570]
[2]Vijayaraghavan; Kar, Mega; Sivanesh; Samuel; Surianarayanan; Olsen, Seth; MacFarlane [Chemical Communications, 2020, vol. 56, # 79, p. 11819 - 11822]
[3]Miran, Muhammed Shah; Yasuda, Tomohiro; Susan, Md. Abu Bin Hasan; Dokko, Kaoru; Watanabe, Masayoshi [RSC Advances, 2013, vol. 3, # 13, p. 4141 - 4144]
[4]Goodwin, Sean E.; Smith, Daniel E.; Gibson, Joshua S.; Jones, Robert G.; Walsh, Darren A. [Langmuir, 2017, vol. 33, # 34, p. 8436 - 8446]

53
[ 616-39-7 ]
[ 3282-32-4 ]
[ 2431-96-1 ]
N-methyl-N-ethyl-2-phenylacetamide [ No CAS ]
[ 101-41-7 ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 679 - 685

54
[ 616-39-7 ]
[ 2969-81-5 ]
[ 1580506-95-1 ]

Yield	Reaction Conditions	Operation in experiment
87%	In acetone at 20℃; for 192h;

Reference： [1]Tars, Kaspars; Leitans, Janis; Kazaks, Andris; Zelencova, Diana; Liepinsh, Edgars; Kuka, Janis; Makrecka, Marina; Lola, Daina; Andrianovs, Viktors; Gustina, Daina; Grinberga, Solveiga; Liepinsh, Edvards; Kalvinsh, Ivars; Dambrova, Maija; Loza, Einars; Pugovics, Osvalds [Journal of Medicinal Chemistry, 2014, vol. 57, # 6, p. 2213 - 2236]

55
[ 616-39-7 ]
[ 3970-21-6 ]
[ 333-27-7 ]
diethyl(2-methoxyethoxymethyl)methylammonium trifluoromethanesulfonate [ No CAS ]