[ CAS No. 1912-32-9 ] {[proInfo.proName]}

Name: 1912-32-9|Butyl methanesulfonate|98% contains 4% DCM at maximum
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3d Animation Molecule Structure of 1912-32-9

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Quality Control of [ 1912-32-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1912-32-9 ]

SDS Specification

Alternatived Products of [ 1912-32-9 ]

Product Details of [ 1912-32-9 ]

CAS No. :	1912-32-9	MDL No. :	MFCD00041257
Formula :	C₅H₁₂O₃S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LFLBHTZRLVHUQC-UHFFFAOYSA-N
M.W :	152.21	Pubchem ID :	15953
Synonyms :

Calculated chemistry of [ 1912-32-9 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	36.2
TPSA :	51.75 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.59 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.75
Log Po/w (XLOGP3) :	0.9
Log Po/w (WLOGP) :	1.84
Log Po/w (MLOGP) :	0.72
Log Po/w (SILICOS-IT) :	0.21
Consensus Log Po/w :	1.09

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.09
Solubility :	12.5 mg/ml ; 0.0819 mol/l
Class :	Very soluble
Log S (Ali) :	-1.57
Solubility :	4.08 mg/ml ; 0.0268 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.52
Solubility :	4.63 mg/ml ; 0.0304 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.57

Safety of [ 1912-32-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1912-32-9 ]

* 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.

Upstream synthesis route of [ 1912-32-9 ]
Downstream synthetic route of [ 1912-32-9 ]

[ 1912-32-9 ] Synthesis Path-Upstream 1~13

1
[ 1912-32-9 ]
[ 105-53-3 ]
[ 596-75-8 ]
[ 133-08-4 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 2159 - 2162

2
[ 1912-32-9 ]
[ 141-97-9 ]
[ 55501-16-1 ]
[ 1609-61-6 ]
[ 92238-43-2 ]
[ 1540-29-0 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 2159 - 2162

3
[ 2634-33-5 ]
[ 1912-32-9 ]
[ 4299-07-4 ]

Yield	Reaction Conditions	Operation in experiment
98%	Stage #1: With sodium methylate In methanol at 0℃; for 1 h; Stage #2: for 6 h;	151 g of 99percent 1,2'-benzisothiazolin-3-one(1 mol) was added to 257 g of methanol, and 193 g of a 28percent solution of sodium methoxide in methanol (sodium methanol) was added dropwise, followed by stirring and stirring for 1 hour to 0 0C. 160 g of n-butyl methanesulfonate Mol, the reaction was carried out for 6 hours, the solvent was distilled off under reduced pressure, 300 g of toluene was added, washed twice with water, and toluene was recovered under reduced pressure to give 2-butyl-1,2-benzisothiazoline -3-carboxylate (HPLC> 98percent) in a yield of 98percent.

Reference： [1] Patent: CN104130206, 2016, B, . Location in patent: Paragraph 0027

4
[ 124-63-0 ]
[ 71-36-3 ]
[ 1912-32-9 ]

Yield	Reaction Conditions	Operation in experiment
92%	With pyridine In dichloromethane at 0 - 20℃; for 6 h;	To a solution of butanol (500 mg, 6.7 mmol) in dry CH2Cl2 (10 mL) pyridine (0.82 mL, 10.1 mmol) and MsCl (0.78 mL, 10.1 mmol) were added in sequence. The reaction was stirred at 0°C and allowed to warm to temperature. After 6 h, the mixture was quenched with MeOH and concentrated, then diluted with ethyl acetate (50 mL), washed with 1M HCl (10 mL), saturated NaHCO3 (10 mL) and saturated brine (10 mL), the organic layer was dried over anhydrous Na2SO4 and concentrated. The resulting residue was purified by silica gel column chromatography to afford compound 2 as colorless oil (0.94 g, 92percent). 1H NMR (400 MHz,CDCl3) δ 4.24 (t, J = 13.2, 6.4 Hz, 2H), 3.01 (s, 3H), 1.76–1.72 (m, 2H), 1.48–1.42 (m, 2H), 0.96 (t, J = 12.8, 7.6 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 69.99,37.30, 31.05, 18.67, 13.48.HRMS(ESI) calcd for [C5H12SO3 +Na]+ 175.0405, found 175.0401
91%	With N-ethyl-N,N-diisopropylamine In dichloromethane at -5 - 0℃; for 0.5 h;	A) Methanesulfonic acid butyl ester. n-Butanol (6.7 g, 8.2 mL, 0.090 mol) was dissolved in 30 mL anhydrous methylene chloride and diisopropylethylamine (19.4 g, 26.1 mL, 0.150 mol) was added. The solution was cooled to -5 ⁰C and methanesulfonyl chloride (11.4 g, 7.74 mL, 0.100 mol) was added dropwise followed by stirring for 0.5 hours at -5 to 0⁰C. After 0.5 hours, the reaction was quenched with ice cold water. The crude mixture was washed with ice cold water, cold 10 percent hydrochloric acid, followed by cold water and then cold sodium bicarbonate solution and finally with cold brine. The organic phase was dried over anhydrous magnesium sulfate and the solvent was removed by evaporation. The sub-title product (13.8 g, 91percent) was extracted as slightly brownish liquid after removal of solvents in vacua. The sub-title product was used in the next step without further purification.¹H NMR (400 MHz, chloroforn>d as solvent and internal reference) δ (ppm) 4.19 (t, 2H, J = 6.5 Hz), 2.96 (s, 3H), 1.69 (m, 2H), 1.40 (m, 2H), 0.91 (t, 2H, J- 7.3 Hz).
90%	With triethylamine In dichloromethane at -10 - 20℃;	Methanesulfonyl chloride (15.45 g, 0.13 mol) was added to a mixture of n-butanol (10 g, 0.13 mol), triethylamine (26.3 g, 0.26 mol) and dichloromethane (150 g) at 10 C. After being stirred at room temperature overnight, water (100 g) was added to the reaction mixture and the layers were separated. The organic layer was concentrated in vacuo at room temperature. This gave 18 g (90percent) of the title mesylate as an oil. 1H NMR analysis supports the stated structure. *Previously described in J. Amer. Chem. Soc. 1933,55, 345-349.

Reference： [1] Journal of the Indian Chemical Society, 2009, vol. 86, # 8, p. 841 - 848
[2] Organic and Biomolecular Chemistry, 2018, vol. 16, # 41, p. 7753 - 7759
[3] Synthesis, 1981, # 2, p. 155 - 156
[4] Advanced Synthesis and Catalysis, 2006, vol. 348, # 1-2, p. 243 - 248
[5] Journal of Molecular Catalysis A: Chemical, 2011, vol. 351, p. 41 - 45
[6] Journal of Carbohydrate Chemistry, 2016, vol. 35, # 8-9, p. 445 - 454
[7] Patent: WO2007/8143, 2007, A1, . Location in patent: Page/Page column 60-61
[8] Patent: WO2004/9586, 2004, A1, . Location in patent: Page 52
[9] Catalysis Today, 2011, vol. 171, # 1, p. 236 - 241
[10] Journal of the American Chemical Society, 1933, vol. 55, p. 348
[11] Hoppe-Seyler's Zeitschrift für physiologische Chemie, 1961, vol. 323, p. 211 - 235
[12] Physical Chemistry Chemical Physics, 2009, vol. 11, # 39, p. 8939 - 8948
[13] Amino Acids, 2010, vol. 38, # 2, p. 509 - 517
[14] Molecules, 2016, vol. 21, # 10,
[15] Patent: KR2016/19911, 2016, A, . Location in patent: Paragraph 0075-0077

5
[ 1927-68-0 ]
[ 124-63-0 ]
[ 1912-32-9 ]

Reference： [1] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2005, vol. 60, # 7, p. 763 - 765

6
[ 1825-65-6 ]
[ 124-63-0 ]
[ 1912-32-9 ]

Reference： [1] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2005, vol. 60, # 7, p. 763 - 765

7
[ 109-72-8 ]
[ 124-63-0 ]
[ 1912-32-9 ]

Reference： [1] Journal of Organic Chemistry, 2006, vol. 71, # 3, p. 1018 - 1026

8
[ 109-72-8 ]
[ 124-63-0 ]
[ 1912-32-9 ]
[ 14320-38-8 ]
[ 253680-54-5 ]

Reference： [1] Journal of Organic Chemistry, 2006, vol. 71, # 3, p. 1018 - 1026

9
[ 124-63-0 ]
[ 2372-45-4 ]
[ 1912-32-9 ]

Reference： [1] Canadian Journal of Chemistry, 1957, vol. 35, p. 1319,1322

10
[ 51761-36-5 ]
[ 1912-32-9 ]

Reference： [1] J. Gen. Chem. USSR (Engl. Transl.), 1973, vol. 43, p. 2638 - 2640[2] Zhurnal Obshchei Khimii, 1973, vol. 43, p. 2660 - 2663

11
[ 75-75-2 ]
[ 1912-32-9 ]
[ 123-95-5 ]
[ 57-11-4 ]
[ 822-16-2 ]
[ 2386-57-4 ]

Reference： [1] Patent: US2006/30725, 2006, A1, . Location in patent: Page/Page column 6

12
[ 75-75-2 ]
[ 1912-32-9 ]
[ 123-95-5 ]
[ 57-11-4 ]
[ 822-16-2 ]
[ 2386-57-4 ]

Reference： [1] Patent: US2006/30725, 2006, A1, . Location in patent: Page/Page column 6

13
[ 1912-32-9 ]
[ 2386-57-4 ]

Reference： [1] Patent: US2006/30725, 2006, A1, . Location in patent: Page/Page column 6; 7
[2] Patent: US2006/30725, 2006, A1, . Location in patent: Page/Page column 6; 7

[ 1912-32-9 ] Synthesis Path-Downstream 1~88

1
[ 106-44-5 ]
[ 1912-32-9 ]
[ 51528-17-7 ]

Reference： [1]Journal of the Chemical Society,1959,p. 2513,2515

2
[ 576-26-1 ]
[ 1912-32-9 ]
[ 107055-25-4 ]

Reference： [1]Journal of the Chemical Society,1959,p. 2513,2515
[2]Journal of the Chemical Society,1959,p. 2513,2515

3
[ 1912-32-9 ]
[ 2303-76-6 ]
[ 2404-75-3 ]

Reference： [1]Journal of the American Chemical Society,1954,vol. 76,p. 4172

4
[ 1912-32-9 ]
[ 127-09-3 ]
[ 123-86-4 ]

Reference： [1]Journal of the American Chemical Society,1933,vol. 55,p. 348

5
[ 1912-32-9 ]
[ 4813-50-7 ]

Reference： [1]Journal of the American Chemical Society,1954,vol. 76,p. 2984,2986
[2]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1961,vol. 323,p. 211 - 235

6
[ 1912-32-9 ]
[ 3849-34-1 ]

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 551,552,553

7
[ 124-63-0 ]
[ 2372-45-4 ]
[ 1912-32-9 ]

Reference： [1]Canadian Journal of Chemistry,1957,vol. 35,p. 1319,1322

8
[ 124-63-0 ]
[ 71-36-3 ]
[ 1912-32-9 ]

Yield	Reaction Conditions	Operation in experiment
92%	With pyridine; In dichloromethane; at 0 - 20℃; for 6h;	To a solution of butanol (500 mg, 6.7 mmol) in dry CH2Cl2 (10 mL) pyridine (0.82 mL, 10.1 mmol) and MsCl (0.78 mL, 10.1 mmol) were added in sequence. The reaction was stirred at 0C and allowed to warm to temperature. After 6 h, the mixture was quenched with MeOH and concentrated, then diluted with ethyl acetate (50 mL), washed with 1M HCl (10 mL), saturated NaHCO3 (10 mL) and saturated brine (10 mL), the organic layer was dried over anhydrous Na2SO4 and concentrated. The resulting residue was purified by silica gel column chromatography to afford compound 2 as colorless oil (0.94 g, 92%). 1H NMR (400 MHz,CDCl3) delta 4.24 (t, J = 13.2, 6.4 Hz, 2H), 3.01 (s, 3H), 1.76-1.72 (m, 2H), 1.48-1.42 (m, 2H), 0.96 (t, J = 12.8, 7.6 Hz, 3H); 13C NMR (100 MHz, CDCl3) delta 69.99,37.30, 31.05, 18.67, 13.48.HRMS(ESI) calcd for [C5H12SO3 +Na]+ 175.0405, found 175.0401
91%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -5 - 0℃; for 0.5h;	A) Methanesulfonic acid butyl ester. n-Butanol (6.7 g, 8.2 mL, 0.090 mol) was dissolved in 30 mL anhydrous methylene chloride and diisopropylethylamine (19.4 g, 26.1 mL, 0.150 mol) was added. The solution was cooled to -5 0C and methanesulfonyl chloride (11.4 g, 7.74 mL, 0.100 mol) was added dropwise followed by stirring for 0.5 hours at -5 to 00C. After 0.5 hours, the reaction was quenched with ice cold water. The crude mixture was washed with ice cold water, cold 10 % hydrochloric acid, followed by cold water and then cold sodium bicarbonate solution and finally with cold brine. The organic phase was dried over anhydrous magnesium sulfate and the solvent was removed by evaporation. The sub-title product (13.8 g, 91%) was extracted as slightly brownish liquid after removal of solvents in vacua. The sub-title product was used in the next step without further purification.1H NMR (400 MHz, chloroforn>d as solvent and internal reference) delta (ppm) 4.19 (t, 2H, J = 6.5 Hz), 2.96 (s, 3H), 1.69 (m, 2H), 1.40 (m, 2H), 0.91 (t, 2H, J- 7.3 Hz).
90%	With triethylamine; In dichloromethane; at -10 - 20℃;	Methanesulfonyl chloride (15.45 g, 0.13 mol) was added to a mixture of n-butanol (10 g, 0.13 mol), triethylamine (26.3 g, 0.26 mol) and dichloromethane (150 g) at 10 C. After being stirred at room temperature overnight, water (100 g) was added to the reaction mixture and the layers were separated. The organic layer was concentrated in vacuo at room temperature. This gave 18 g (90%) of the title mesylate as an oil. 1H NMR analysis supports the stated structure. *Previously described in J. Amer. Chem. Soc. 1933,55, 345-349.

	With triethylamine; In dichloromethane; at 20℃; for 2.5h;Inert atmosphere; Cooling with ice;	Solution of methanesulfonyl chloride (5.23 g, 45.66 mmol) in dichloromethane (55 mL) wasslowly added to the ice bathed solution of butanol (2.82 g, 38.05 mmol) and triethylamine (10.6 mL,76.10 mmol) in dichloromethane (55 mL). The resulting solution was allowed to react in an ice bath for30 min and then brought to ambient temperature for another 2 h. Sequentially, the reaction solutionwas washed with citric acid (10 wt %, 3 15 mL), sodium bicarbonate (10 wt %, 3 15 mL), thendried over Na2SO4. After filtration, the solvent was removed under reduced pressure to afford highpurity product (5.77 g, quantitative yield) with no need for further purification. To a round bottleflask containing 4,5,6,7-tetra-hydro[1,2,3]triazolo[1,5-a]pyridine (4.13 g, 33.52 mmol) was added butylmethanesulfonate (5.73 g, 37.64 mmol). The alkylation reaction was carried out at 80 C for 18 h.After completion of reaction, the mixture was allowed to cool and then ether was added to extract andwash away remaining starting reagents, if any. Ether layer (140 mL in total) was removed and thenthe ionic liquid was concentrated under reduced pressure to afford the desired [b-4C-tr][OMs] (8.94 g,97% yield). To the solution of [b-4C-tr][OMs] (8.94 g, 32.45 mmol) in water (5 mL) was added LiNTf2(10.59 g, 36.87 mmol). The metathesis reaction was allowed to proceed at ambient temperature for13 h. After completion of the ion exchange, the solution mixture was extracted with dichloromethane(3 x 5 mL). The combined organic layers were dried over Na2SO4. Evaporation of the solvent in vacuoafford the ionic liquid 1, [b-4C-tr][NTf2] (14.54 g, 98% yield).
	With triethylamine; In di-isopropyl ether; at 0 - 25℃; for 8.5h;Inert atmosphere;	A 2 L glass reactor equipped with a stirrer, a dropping funnel, and a Dimroth condenser was charged with 1-butanol (74 g), methanesulfonyl chloride (126 g), and dry diisopropyl ether (500 mL). The mixture was subjected to a nitrogen atmosphere. The reactor was cooled with ice water, and triethylamine (121 g) was added dropwise to the mixture from the dropping funnel over about 2 hours. After the dropwise addition, the mixture was stirred at 0C for 30 minutes, and then stirred at 25C for 6 hours.500 mL of ice water was added to the reaction mixture to dissolve triethylamine hydrochloride produced to separate the reaction mixture into two layers. The upper organic layer was sequentially washed with 5% hydrochloric acid, saturated sodium bicarbonate water, and a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate, and magnesium sulfate was filtered off. Diisopropyl ether was evaporated from the filtrate using a rotary evaporator, followed by pumping up using a vacuum pump to obtain 119 g of crude methanesulfonyloxybutane.

Reference： [1]Journal of the Indian Chemical Society,2009,vol. 86,p. 841 - 848
[2]Organic and Biomolecular Chemistry,2018,vol. 16,p. 7753 - 7759
[3]Synthesis,1981,p. 155 - 156
[4]Advanced Synthesis and Catalysis,2006,vol. 348,p. 243 - 248
[5]Journal of Molecular Catalysis A: Chemical,2011,vol. 351,p. 41 - 45
[6]Journal of Carbohydrate Chemistry,2016,vol. 35,p. 445 - 454
[7]Patent: WO2007/8143,2007,A1 .Location in patent: Page/Page column 60-61
[8]Patent: WO2004/9586,2004,A1 .Location in patent: Page 52
[9]Catalysis Today,2011,vol. 171,p. 236 - 241
[10]Journal of the American Chemical Society,1933,vol. 55,p. 348
[11]Hoppe-Seyler's Zeitschrift fur Physiologische Chemie,1961,vol. 323,p. 211 - 235
[12]Physical Chemistry Chemical Physics,2009,vol. 11,p. 8939 - 8948
[13]Amino Acids,2010,vol. 38,p. 509 - 517
[14]Molecules,2016,vol. 21
[15]Patent: KR2016/19911,2016,A .Location in patent: Paragraph 0075-0077

9
[ 1912-32-9 ]
[ 106-48-9 ]
[ 52184-12-0 ]

Reference： [1]Journal of the Chemical Society,1959,p. 2513,2515

10
[ 1912-32-9 ]
[ 62-53-3 ]
[ 1126-78-9 ]

Reference： [1]Journal of the Indian Chemical Society,2009,vol. 86,p. 841 - 848
[2]Journal of the American Chemical Society,1933,vol. 55,p. 348
[3]Journal of the American Chemical Society,1933,vol. 55,p. 348

11
[ 1912-32-9 ]
[ 105-67-9 ]
[ 69236-48-2 ]

Reference： [1]Journal of the Chemical Society,1959,p. 2513,2515

12
[ 1912-32-9 ]
[ 120-83-2 ]
[ 96293-24-2 ]

Reference： [1]Journal of the Chemical Society,1959,p. 2513,2515
[2]Journal of the Chemical Society,1959,p. 2513,2515

13
[ 1912-32-9 ]
[ 150-78-7 ]
[ 590-18-1 ]
[ 13620-78-5 ]
[ 150-76-5 ]

Reference： [1]Journal of the Chemical Society,1959,p. 2513,2515

14
[ 1912-32-9 ]
[ 108-67-8 ]
[ 107-01-7 ]
[ 6462-31-3 ]
[ 84651-10-5 ]
[ 92102-13-1 ]

Reference： [1]Journal of the Chemical Society,1959,p. 2520,2522

15
[ 1912-32-9 ]
[ 108-67-8 ]
[ 527-53-7 ]

Reference： [1]Journal of the Chemical Society,1959,p. 2520,2522

16
[ 1912-32-9 ]
[ 108-67-8 ]
[ 84651-10-5 ]

Reference： [1]Journal of the Chemical Society,1959,p. 2520,2522

17
[ 1912-32-9 ]
furan-2,3,5(4H)-trione pyridine (1:1) [ No CAS ]
[ 108-95-2 ]
[ 1126-79-0 ]

Reference： [1]Journal of the American Chemical Society,1933,vol. 55,p. 348

18
[ 1912-32-9 ]
[ 108-95-2 ]
[ 1126-79-0 ]

Reference： [1]Journal of the American Chemical Society,1933,vol. 55,p. 348

19
[ 998-40-3 ]
[ 1912-32-9 ]
[ 98342-59-7 ]

Reference： [1]Chemische Berichte,1964,vol. 97,p. 2534 - 2538

20
[ 51761-36-5 ]
[ 1912-32-9 ]

Reference： [1]Journal of general chemistry of the USSR,1973,vol. 43,p. 2638 - 2640
Zhurnal Obshchei Khimii,1973,vol. 43,p. 2660 - 2663

21
[ 1912-32-9 ]
[ 603-35-0 ]
[ 91949-57-4 ]

Reference： [1]Journal of Organic Chemistry,1984,vol. 49,p. 4293 - 4295
[2]Chemische Berichte,1964,vol. 97,p. 2534 - 2538

22
[ 616-45-5 ]
[ 1912-32-9 ]
[ 3470-98-2 ]

Reference： [1]Chemistry Letters,1986,p. 425 - 428

23
[ 1912-32-9 ]
[ 38023-29-9 ]
1,2-Bis-(butyl-phenyl-phosphanyl)-benzene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1981,vol. 103,p. 3868

24
[ 1912-32-9 ]
[ 133827-52-8 ]
[ 113768-50-6 ]

Reference： [1]Tetrahedron Letters,1987,vol. 28,p. 2993 - 2994

25
[ 1912-32-9 ]
[ 75494-87-0 ]
[ 111922-41-9 ]
[ 111922-42-0 ]

Reference： [1]Tetrahedron Letters,1987,vol. 28,p. 1047 - 1050

26
[ 1912-32-9 ]
[ 61477-12-1 ]
[ 113116-53-3 ]

Reference： [1]Tetrahedron,1987,vol. 43,p. 1091 - 1098

27
[ 1912-32-9 ]
[ 93273-86-0 ]
N-benzoyl-O-menthyl-(S)-norleucine [ No CAS ]
N-benzoyl-O-menthyl-(R)-norleucine [ No CAS ]

Reference： [1]Journal of Chemical Research, Miniprint,1984,p. 1518 - 1530
[2]Journal of Chemical Research, Miniprint,1984,p. 1518 - 1530

28
[ 1912-32-9 ]
C₆H₁₄N₂OS [ No CAS ]
C₁₀H₂₂N₂OS [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 1922 - 1923

29
[ 1912-32-9 ]
[ 76031-50-0 ]
[ 73735-17-8 ]

Reference： [1]Journal of Medicinal Chemistry,1985,vol. 28,p. 1943 - 1947

30
[ 1912-32-9 ]
[ 106-98-9 ]
[ 75-75-2 ]

Reference： [1]Journal of Physical Chemistry,1989,vol. 93,p. 201 - 202

31
[ 1912-32-9 ]
[ 83561-05-1 ]

Reference： [1]Journal of the American Chemical Society,1982,vol. 104,p. 7311 - 7312

32
[ 1912-32-9 ]
[ 141-97-9 ]
[ 55501-16-1 ]
[ 1609-61-6 ]
[ 92238-43-2 ]
[ 1540-29-0 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1987,p. 2159 - 2162

33
[ 1912-32-9 ]
[ 105-53-3 ]
[ 596-75-8 ]
[ 133-08-4 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1987,p. 2159 - 2162

34
[ 1912-32-9 ]
[ 80-97-7 ]
(3S,5S,8R,9S,10S,13R,14S,17R)-3-Butoxy-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthrene [ No CAS ]

Reference： [1]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,1994,vol. 250,p. 73 - 84

35
[ 1912-32-9 ]
(1S,3S,4S)-1-Aza-bicyclo[2.2.1]heptane-3-carbaldehyde oxime [ No CAS ]
(1S,3S,4S)-1-Aza-bicyclo[2.2.1]heptane-3-carbaldehyde O-butyl-oxime [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 4265 - 4280

36
[ 1912-32-9 ]
[ 120-12-7 ]
[ 47205-57-2 ]
[ 10394-60-2 ]
[ 126694-91-5 ]
1-butyl-1,2-dihydroanthracene [ No CAS ]

Reference： [1]Acta Chemica Scandinavica,1998,vol. 52,p. 51 - 61

37
[ 451-40-1 ]
[ 1912-32-9 ]
1-butoxy-1,2-diphenylethene [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1998,vol. 63,p. 5356 - 5361

40
[ 1912-32-9 ]
[ 7722-84-1 ]
methanol. KOH-solution [ No CAS ]
[ 4813-50-7 ]
[ 3849-34-1 ]

Reference： [1]Journal of the American Chemical Society,1954,vol. 76,p. 2984,2986

41
[ 1912-32-9 ]
sodium acetate dihydrate [ No CAS ]
[ 123-86-4 ]

Reference： [1]Journal of the American Chemical Society,1933,vol. 55,p. 348

Yield	Reaction Conditions	Operation in experiment
96%	With triethylamine; In tert-butyl methyl ether; at 0 - 20℃; for 2h;	General procedure: Rawmaterial 1a (47g, 0.4mol. 1eq), Triethylamine(51.8g, 0.51mol, 1.28eq), MuTauBetaEpsilon (400ml) was added to a 1L reaction flask, ice-water bath Down to 0C after dropping MsCl (50.4g, 0.44mol, 1.1eq). After dropping completes, the drops stirred at room temperature for 2 hours the reaction was stopped. The organic phase/layer washed with saturated NaHCO3, Washed with saturated brine then dried and concentrated to give the product (83.3g, 0.4mol) Yield 100%.
68.1 g (98%)		Preparation of butyl methanesulfonate (BuOMs) To a 500 cm3 round-bottomed flask, equipped with a magnetic stirrer and pressure equalising dropping funnel, was added butanol (55,6 g, 0.75 mol), triethylamine (55.7 g, 0.55 mol) and dichloromethane (300 cm3). Methanesulfonyl chloride (57.3 g, 0.05 mol) was then added dropwise over a two-hour period from the dropping funnel, with cooling from an ice bath. The mixture was stirred for a further 24 hours at room temperature. The reaction mixture was filtered, concentrated on a rotary evaporator, and distilled (bp-80-90 C. at 5 mm Hg). This gave 68.1 g (98%) of a colourless oil.
		Examples of the sulfonic acid ester of the formula (V') include the following: methyl methanesulfonate, ethyl methanesulfonate, propyl methanesulfonate, isopropyl methanesulfonate, butyl methanesulfonate, pentyl methanesulfonate, hexyl methanesulfonate, heptyl methanesulfonate, octyl methanesulfonate, ...

43
[ 542-69-8 ]
silver methanesulfonate [ No CAS ]
[ 1912-32-9 ]

Reference： [1]Journal of the American Chemical Society,1953,vol. 75,p. 2257

44
[ 1912-32-9 ]
[ 22316-50-3 ]
[ 23954-67-8 ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 3596 - 3613

45
[ 100-76-5 ]
[ 1912-32-9 ]
1-butyl-1-azonia-bicyclo[2.2.2]octane; methanesulfonate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 11222 - 11223

46
[ 616-47-7 ]
[ 1912-32-9 ]
[ 342789-81-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	at 25℃; for 48h;	Example 11-butyl-3-methyl imidazolium methane-sulfonate (BMI.CH3SO3)Butyl methanesulfonate (45.60 g; 300 mmol) was mixed with 1-methyl imidazolium (24.60 g; 300 mmol) and the reaction mixture was allowed to stand at room temperature (25 C.) for 48 hours. After this period of time, an identical volume of acetone and one 1-butyl-3-methylimidazolium methanesulfonate crystal were added, in order to induce the crystallization of the product. The mixture was kept in the refrigerator overnight. A yellow, supernatant solution was decanted from the almost colorless crystals and the crystallization process was again repeated. After drying under vacuum, colorless BMI.CH3SO3 crystals were obtained (59.70 g; 85% yield); the melting point was 77.2 C., RMN-1H (CDCl3) delta:9.67 (1H, s, C-H imidazolium);7.47 (1H, t, J=1.8 Hz, C-H imidazolium);7.36 (1H, t, J=1.8 Hz, C-H imidazolium);4.11 (2H, t, J=7.2 Hz, NCH2);3.89 (3H, s, NCH3);2.59 (3H, s, CH3SO3);1.72 (2H, quintet, J=7.2 Hz, CH2);1.20 (2H, sextet, J=7.2 Hz, CH2);0.79 (3H, t, J=7.2 Hz, CH3);RMN-13C (CDCl3) delta:137.4; 123.5 and 121.8 (C-H imidazolium);49.2 (NCH2);39.4 (CH3SO3);35.9 (NCH3);31.7 and 19.0 (CH2);13.0 (CH3).

Reference： [1]Green Chemistry,2009,vol. 11,p. 821 - 829
[2]Advanced Synthesis and Catalysis,2006,vol. 348,p. 243 - 248
[3]Catalysis Today,2011,vol. 171,p. 236 - 241
[4]New Journal of Chemistry,2018,vol. 42,p. 13828 - 13835
[5]Physical Chemistry Chemical Physics,2009,vol. 11,p. 8939 - 8948
[6]Patent: US2008/45723,2008,A1 .Location in patent: Page/Page column 3

47
[ 1739-84-0 ]
[ 1912-32-9 ]
1-n-butyl-2,3-dimethylimidazolium methanesulfonate [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2006,vol. 348,p. 243 - 248

48
[ 4316-42-1 ]
[ 1912-32-9 ]
1,3-dibutylimidazolium methanesulfonate [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2006,vol. 348,p. 243 - 248
[2]Chemistry - A European Journal,2015,vol. 21,p. 13297 - 13301

49
2',2'-dibromocycloprop-1'-yloxirane [ No CAS ]
[ 109-72-8 ]
[ 124-63-0 ]
endo-bicyclo[1.1.0]but-2-ylcarbinyl mesylate [ No CAS ]
[ 1912-32-9 ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 1018 - 1026

50
2',2'-dibromocycloprop-1'-yloxirane [ No CAS ]
[ 109-72-8 ]
[ 124-63-0 ]
[ 1912-32-9 ]
[ 14320-38-8 ]
[ 253680-54-5 ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 1018 - 1026

51
[ 1927-68-0 ]
[ 124-63-0 ]
[ 1912-32-9 ]

Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2005,vol. 60,p. 763 - 765

52
[ 1825-65-6 ]
[ 124-63-0 ]
[ 1912-32-9 ]

Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2005,vol. 60,p. 763 - 765

53
3-(1-piperazinyl)-1-[2-(2,4,5-trifluorophenoxy)ethyl]-2(1H)-pyrazinone hydrochloride [ No CAS ]
[ 1912-32-9 ]
1-[2-(2,4,5-trifluorophenoxy)ethyl]-3-(4-N-butyl-1-piperazinyl)-2(1H)-pyrazinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8%	With potassium carbonate; In dimethyl sulfoxide; at 60℃; for 3h;	Methanesulfonic acid butyl ester (0.30 g, 1,97 mmol; from Step 1) was added to a mixture of 3-(1-piperazinyl)-1-[2-(2,4,5-trifluorophenoxy)ethyl]-2(1H)-pyrazinone (0.50 g, 1.4 mmol; from the free base of Example 3) and potassium carbonate (0.10 g, 2.89 mmol) in DMSO (3 g). After being stirred for 3 h at 60 C, water (50 g) and EtOAc (100 g) were added to the reaction mixture. The layers were separated and the organic layer was concentrated in vacuo. The residue was purified by chromatography on a MPLC column using a continuous gradient (0-100% EtOAc in heptane) as eluent. This furnished 33 mg (8%) of the title compound as an oil. 1H NMR analysis supports the stated structure. HPLC purity: 100%. HRMS m/z calcd for C20H25F3N4O2 (M) + 410.1930, found 410.1920.

Reference： [1]Patent: WO2004/9586,2004,A1 .Location in patent: Page 52; 53

Yield	Reaction Conditions	Operation in experiment
	With calcium hydroxide; water; In butan-1-ol; at 50 - 175℃; for 0.666667 - 1h;Reactivity;	An esterification reaction mixture (94 g), consisting of butanol (ca., 4.9% w/w), butyl stearate (95.1% w/w), residual stearic acid (trace), residual methanesulfonic acid catalyst (1383 ppm) and undesired <strong>[1912-32-9]butyl methanesulfonate</strong> (613 ppm) was treated with 45% aqueous KOH (229 mg, 1.84 mmol as compared to 1.74 mmol MSA originally charged to the reaction). The resulting mixture was heating at 50 C. for 40 minutes. Without wishing to be bound by any particular theory or explanation, it is believed that reaction of butyl stearate with KOH produced potassium stearate, which retains significant solubility in the butyl stearate medium. The formed potassium stearate then reacted with <strong>[1912-32-9]butyl methanesulfonate</strong> to produce potassium methanesulfonate and butyl stearate. After filtration of the by-product solid salts (0.6325 g), analysis of the mixture by gas chromatography revealed only 300 ppm unreacted <strong>[1912-32-9]butyl methanesulfonate</strong>, a 51% reduction. Repetition of the above KOH treatment at a higher temperature (175 C./60 min.) revealed complete reaction of the <strong>[1912-32-9]butyl methanesulfonate</strong>. Similarly, treatment with NaOH was found equally effective as treatment with KOH. Treatment with Ca(OH)2 proved ineffective, presumably due to formation of poorly soluble calcium salts. Treatment with acidic tin(II) or zirconium (IV) salts resulted in formation of additional <strong>[1912-32-9]butyl methanesulfonate</strong>.

55
[ 75-75-2 ]
[ 1912-32-9 ]
[ 123-95-5 ]
[ 57-11-4 ]
[ 822-16-2 ]
[ 2386-57-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; water; In butan-1-ol; at 50 - 175℃; for 0.666667 - 1h;Conversion of starting material;	An esterification reaction mixture (94 g), consisting of butanol (ca., 4.9% w/w), butyl stearate (95.1% w/w), residual stearic acid (trace), residual methanesulfonic acid catalyst (1383 ppm) and undesired <strong>[1912-32-9]butyl methanesulfonate</strong> (613 ppm) was treated with 45% aqueous KOH (229 mg, 1.84 mmol as compared to 1.74 mmol MSA originally charged to the reaction). The resulting mixture was heating at 50 C. for 40 minutes. Without wishing to be bound by any particular theory or explanation, it is believed that reaction of butyl stearate with KOH produced potassium stearate, which retains significant solubility in the butyl stearate medium. The formed potassium stearate then reacted with <strong>[1912-32-9]butyl methanesulfonate</strong> to produce potassium methanesulfonate and butyl stearate. After filtration of the by-product solid salts (0.6325 g), analysis of the mixture by gas chromatography revealed only 300 ppm unreacted <strong>[1912-32-9]butyl methanesulfonate</strong>, a 51% reduction. Repetition of the above KOH treatment at a higher temperature (175 C./60 min.) revealed complete reaction of the <strong>[1912-32-9]butyl methanesulfonate</strong>. Similarly, treatment with NaOH was found equally effective as treatment with KOH. Treatment with Ca(OH)2 proved ineffective, presumably due to formation of poorly soluble calcium salts. Treatment with acidic tin(II) or zirconium (IV) salts resulted in formation of additional <strong>[1912-32-9]butyl methanesulfonate</strong>.

Reference： [1]Patent: US2006/30725,2006,A1 .Location in patent: Page/Page column 6

56
[ 75-75-2 ]
[ 1912-32-9 ]
[ 123-95-5 ]
[ 57-11-4 ]
[ 2386-56-3 ]
[ 593-29-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; water; In butan-1-ol; at 50 - 175℃; for 0.666667 - 1h;Conversion of starting material;	An esterification reaction mixture (94 g), consisting of butanol (ca., 4.9% w/w), butyl stearate (95.1% w/w), residual stearic acid (trace), residual methanesulfonic acid catalyst (1383 ppm) and undesired <strong>[1912-32-9]butyl methanesulfonate</strong> (613 ppm) was treated with 45% aqueous KOH (229 mg, 1.84 mmol as compared to 1.74 mmol MSA originally charged to the reaction). The resulting mixture was heating at 50 C. for 40 minutes. Without wishing to be bound by any particular theory or explanation, it is believed that reaction of butyl stearate with KOH produced potassium stearate, which retains significant solubility in the butyl stearate medium. The formed potassium stearate then reacted with <strong>[1912-32-9]butyl methanesulfonate</strong> to produce potassium methanesulfonate and butyl stearate. After filtration of the by-product solid salts (0.6325 g), analysis of the mixture by gas chromatography revealed only 300 ppm unreacted <strong>[1912-32-9]butyl methanesulfonate</strong>, a 51% reduction. Repetition of the above KOH treatment at a higher temperature (175 C./60 min.) revealed complete reaction of the <strong>[1912-32-9]butyl methanesulfonate</strong>. Similarly, treatment with NaOH was found equally effective as treatment with KOH. Treatment with Ca(OH)2 proved ineffective, presumably due to formation of poorly soluble calcium salts. Treatment with acidic tin(II) or zirconium (IV) salts resulted in formation of additional <strong>[1912-32-9]butyl methanesulfonate</strong>.

Reference： [1]Patent: US2006/30725,2006,A1 .Location in patent: Page/Page column 6

57
[ 1912-32-9 ]
[ 75-75-2 ]

Yield	Reaction Conditions	Operation in experiment
	With Phthalic acid dibutyl ester; water; at 90℃; for 0.25 - 3h;Conversion of starting material;	Methyl methanesulfonate (MMS), methyl para-toluenesulfonate (MTS), <strong>[1912-32-9]butyl methanesulfonate</strong> (BMS), or butyl para-toluenesulfonate (BTS) was combined with either dimethyl phthalate (DMP) or dibutyl phthalate (DBP) to obtain initial mixtures with 55-148 ppm (w/w) sulfonate ester as tabulated below. The mixtures were then heated with vigorous stirring to 180 C., then cooled to 90 C. to simulate general esterification conditions. After such preparation, the resulting mixtures would have compositions similar to those observed in crude esterification product mixtures from typical commercial manufacturing processes. An aliquot of each mixture was taken at this point to represent the material prior to hydrolysis (i.e., time ?0?). The hydrolysis medium was then added (30 ml water, aqueous 10% NaOH, or aqueous 10% Na2CO3) and the stirred mixture was maintained at 90 C. Aliquot samples were taken at the times specified in the table below. Each aliquot was extracted with diethyl ether, and the ether extracts washed with water, dried, and evaporated under vacuum to obtain the dry phthalate ester with residual sulfonate ester. The latter were then analyzed by gas chromatography to determine the amount of residual sulfonate ester. Initial Residual Sulfonate ester (ppm Sulfonate ester by weight) in Phthalate ester Phthalate Sulfonate Before Heating Hydrolysis after Hydrolysis Time (min.) Ester Ester (ppm w/w) Medium 0 15 30 60 120 180 DMP 200 ml MMS 55 Water 34 15 10 5.2 1.3 DMP 200 ml MTS 95 Water 101 98 93 93 83 DBP 200 ml BMS 55 Water 51 35 34 31 23 DBP 200 ml BTS 84 Water 81 78 76 76 72 DMP 100 ml MMS 136 Aq. NaOH 68 4 - <1 <1 - DMP 200 ml MTS 97 Aq. NaOH 70 64 53 40 24 DBP 200 ml BMS 48 Aq. NaOH 18 13 - 14 10 - DBP 200 ml BTS 84 Aq. NaOH 61 59 59 54 55 DMP 100 ml MMS 148Aq. Na2CO3 - 3 - <1 <1 - DBP 100 ml BMS 96Aq. Na2CO3 30 33 - 31 17 -

Reference： [1]Patent: US2006/30725,2006,A1 .Location in patent: Page/Page column 6; 7

58
[ 1912-32-9 ]
[ 2386-57-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; Phthalic acid dibutyl ester; water; at 90℃; for 0.25 - 3h;Conversion of starting material;	Methyl methanesulfonate (MMS), methyl para-toluenesulfonate (MTS), <strong>[1912-32-9]butyl methanesulfonate</strong> (BMS), or butyl para-toluenesulfonate (BTS) was combined with either dimethyl phthalate (DMP) or dibutyl phthalate (DBP) to obtain initial mixtures with 55-148 ppm (w/w) sulfonate ester as tabulated below. The mixtures were then heated with vigorous stirring to 180 C., then cooled to 90 C. to simulate general esterification conditions. After such preparation, the resulting mixtures would have compositions similar to those observed in crude esterification product mixtures from typical commercial manufacturing processes. An aliquot of each mixture was taken at this point to represent the material prior to hydrolysis (i.e., time ?0?). The hydrolysis medium was then added (30 ml water, aqueous 10% NaOH, or aqueous 10% Na2CO3) and the stirred mixture was maintained at 90 C. Aliquot samples were taken at the times specified in the table below. Each aliquot was extracted with diethyl ether, and the ether extracts washed with water, dried, and evaporated under vacuum to obtain the dry phthalate ester with residual sulfonate ester. The latter were then analyzed by gas chromatography to determine the amount of residual sulfonate ester. Initial Residual Sulfonate ester (ppm Sulfonate ester by weight) in Phthalate ester Phthalate Sulfonate Before Heating Hydrolysis after Hydrolysis Time (min.) Ester Ester (ppm w/w) Medium 0 15 30 60 120 180 DMP 200 ml MMS 55 Water 34 15 10 5.2 1.3 DMP 200 ml MTS 95 Water 101 98 93 93 83 DBP 200 ml BMS 55 Water 51 35 34 31 23 DBP 200 ml BTS 84 Water 81 78 76 76 72 DMP 100 ml MMS 136 Aq. NaOH 68 4 - <1 <1 - DMP 200 ml MTS 97 Aq. NaOH 70 64 53 40 24 DBP 200 ml BMS 48 Aq. NaOH 18 13 - 14 10 - DBP 200 ml BTS 84 Aq. NaOH 61 59 59 54 55 DMP 100 ml MMS 148Aq. Na2CO3 - 3 - <1 <1 - DBP 100 ml BMS 96Aq. Na2CO3 30 33 - 31 17 -
	With Phthalic acid dibutyl ester; water; sodium carbonate; at 90℃; for 0.25 - 3h;Conversion of starting material;	Methyl methanesulfonate (MMS), methyl para-toluenesulfonate (MTS), <strong>[1912-32-9]butyl methanesulfonate</strong> (BMS), or butyl para-toluenesulfonate (BTS) was combined with either dimethyl phthalate (DMP) or dibutyl phthalate (DBP) to obtain initial mixtures with 55-148 ppm (w/w) sulfonate ester as tabulated below. The mixtures were then heated with vigorous stirring to 180 C., then cooled to 90 C. to simulate general esterification conditions. After such preparation, the resulting mixtures would have compositions similar to those observed in crude esterification product mixtures from typical commercial manufacturing processes. An aliquot of each mixture was taken at this point to represent the material prior to hydrolysis (i.e., time ?0?). The hydrolysis medium was then added (30 ml water, aqueous 10% NaOH, or aqueous 10% Na2CO3) and the stirred mixture was maintained at 90 C. Aliquot samples were taken at the times specified in the table below. Each aliquot was extracted with diethyl ether, and the ether extracts washed with water, dried, and evaporated under vacuum to obtain the dry phthalate ester with residual sulfonate ester. The latter were then analyzed by gas chromatography to determine the amount of residual sulfonate ester. Initial Residual Sulfonate ester (ppm Sulfonate ester by weight) in Phthalate ester Phthalate Sulfonate Before Heating Hydrolysis after Hydrolysis Time (min.) Ester Ester (ppm w/w) Medium 0 15 30 60 120 180 DMP 200 ml MMS 55 Water 34 15 10 5.2 1.3 DMP 200 ml MTS 95 Water 101 98 93 93 83 DBP 200 ml BMS 55 Water 51 35 34 31 23 DBP 200 ml BTS 84 Water 81 78 76 76 72 DMP 100 ml MMS 136 Aq. NaOH 68 4 - <1 <1 - DMP 200 ml MTS 97 Aq. NaOH 70 64 53 40 24 DBP 200 ml BMS 48 Aq. NaOH 18 13 - 14 10 - DBP 200 ml BTS 84 Aq. NaOH 61 59 59 54 55 DMP 100 ml MMS 148Aq. Na2CO3 - 3 - <1 <1 - DBP 100 ml BMS 96Aq. Na2CO3 30 33 - 31 17 -

Reference： [1]Patent: US2006/30725,2006,A1 .Location in patent: Page/Page column 6; 7
[2]Patent: US2006/30725,2006,A1 .Location in patent: Page/Page column 6; 7

59
salt [bmim] [ No CAS ]
[ 1912-32-9 ]
[ 342789-81-5 ]

Yield	Reaction Conditions	Operation in experiment
	With 1-methyl-1H-imidazole;	Preparation of 1-butyl-3-methylimidazolium methanesulfonate ([bmim] [Oms]) In a 100 cm3 round-bottomed flask, was added <strong>[1912-32-9]butyl methanesulfonate</strong> (15.3 g, 0.10 mol) and 1-methylimidazole (8.21 g, 0.10 mol). A reflux condenser was attached and the mixture heated at 100 C. for 48 hours. A vacuum was applied to the flask (1 mm Hg) to remove unreacted starting materials for 12 hours at 80 C. The low-melting salt [bmim] [Oms] (22.3 g, 95%) solidified on cooling.

Reference： [1]Patent: US2003/80312,2003,A1

60
KOH powder [ No CAS ]
trifluoroacetyl-2,4-difluoroaniline [ No CAS ]
[ 1912-32-9 ]
N-butyltrifluoroacetyl-2,4-difluoroaniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetone;	EXAMPLE 68 Alkylation of a N-acyl compound A mixture of 60.8 g of <strong>[1912-32-9]n-butyl methanesulphonate</strong> and 22.5 g of trifluoroacetyl-2,4-difluoroaniline is dissolved in 50 ml of acetone at 40 C., and 22.4 g of KOH powder are added. The reaction mixture is kept at reflux for 30 minutes, filtered and evaporated on a rotary evaporator. The oily residue is rectified. 15 g of N-butyltrifluoroacetyl-2,4-difluoroaniline are obtained as a yellowish oil which distills at 106 - 110/11.7 mbar. Analysis: calc. C, 51.25; H, 4.30,; F, 33.78; N, 4.98;%. found C, 51.3; H, 4.4; F, 33.4; N, 5.0;%

Reference： [1]Patent: US5026625,1991,A

61
[ 66508-93-8 ]
[ 1912-32-9 ]
[ 68401-32-1 ]

Yield	Reaction Conditions	Operation in experiment
		Analogously to Example 4, stage 1, 79.5 g (0.5 mole) of ethyl 2-hydroxyimino-acetoacetate and 68.3 g (0.45 mole) of n-butyl mesylate give 76 g of ethyl 2-n-butoxyimino-acetoacetate as a colorless oil. NMR (ppm, 60 MHz, (CD3)2 SO): 0.9-1.8 (10H, m, --CH2 --CH3, --CH2 --CH2 --CH3), 2.4 (3H, s, CH3 --CO) and 4.1-4.6 (4H, t+q, 2*--O--CH2 --).

Reference： [1]Patent: US4399131,1983,A

62
[ 1072-63-5 ]
[ 1912-32-9 ]
CH₃O₃S^(1-)*C₉H₁₅N₂⁽¹⁺⁾ [ No CAS ]

Reference： [1]Organic Letters,2008,vol. 10,p. 237 - 240

63
[ 1912-32-9 ]
[ 924638-97-1 ]
[ 1006900-63-5 ]

Reference： [1]Organic Letters,2008,vol. 10,p. 733 - 735

64
[ 1912-32-9 ]
[ 34793-28-7 ]
[ 1190991-35-5 ]

Reference： [1]Green Chemistry,2009,vol. 11,p. 622 - 629

65
[ 111-86-4 ]
[ 1912-32-9 ]
[ 4088-42-0 ]