[ CAS No. 16156-53-9 ] {[proInfo.proName]}

Name: 16156-53-9|Isobutyl Methanesulfonate|98% GC
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Quality Control of [ 16156-53-9 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 16156-53-9 ]

CAS No. :	16156-53-9	MDL No. :	MFCD07363982
Formula :	C₅H₁₂O₃S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PZMKMCFRTKGVOL-UHFFFAOYSA-N
M.W :	152.21	Pubchem ID :	119240
Synonyms :

Safety of [ 16156-53-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P264-P280-P337+P313-P305+P351+P338-P302+P352-P332+P313-P362	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 16156-53-9 ]

* 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.

Downstream synthetic route of [ 16156-53-9 ]

[ 16156-53-9 ] Synthesis Path-Downstream 1~39

1
[ 16156-53-9 ]
[ 5618-63-3 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol; potassium hydroxide; water; dihydrogen peroxide

Reference： [1]Wurster et al. [Journal of the American Chemical Society, 1958, vol. 80, p. 327,328,330,331]

2
[ 16156-53-9 ]
[ 32752-09-3 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol; potassium hydroxide; water; dihydrogen peroxide

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

3
[ 78-83-1 ]
[ 124-63-0 ]
[ 16156-53-9 ]

Yield	Reaction Conditions	Operation in experiment
95.4%	With triethylamine In dichloromethane at 0 - 10℃;	7; 13 Example 7 Synthesis of Isobutyl Mesylate, 152H1-Ms Add 600 g of dichloromethane to the reaction flask, and add 100 g (1.349 mol) of isobutanol.Add 160g (1.581mol) of triethylamine, cool to 0 5 , and control the temperature not more than 10 .160 g (1.397 mmol) of methanesulfonyl chloride was added dropwise;, Keep warm and stir at 0 ~ 10 for about 1 ~ 2hr; after the reaction is completed, add 300g of water, then add 30g of concentrated hydrochloric acid, stir and wash; separate the liquid and wash the organic phase once with 200g of water;Add anhydrous sodium sulfate to dry; filter, filter the residue and rinse with dichloromethane, collect all the filtrate,Combined and concentrated the dry solvent under reduced pressure to give a residue of about 196 g of 152H1-Ms (theoretical amount: 205.4 g). The yield was 95.4%. GC detection, subtracting the peaks of dichloromethane and methanesulfonic acid,The purity is about 99.5%, and the residual isobutanol is 0.42%.
92%	With triethylamine In dichloromethane for 0.5h; Cooling with ice; Inert atmosphere;
80%	With triethylamine; sodium hydroxide at 0 - 20℃;

	With pyridine at 0℃;
68 g (90%)	With triethylamine In dichloromethane	3.1 (1) (1) Preparation of isobutyl methanesulfonate To an ice cooled solution of 37 g (46.1 ml, 0.5 mol) of isobutyl alcohol and 75.75 g (104.3 ml, 0.75 mol) of triethylamine in 1800 ml of dichloromethane is added dropwise 63 g (42.57 ml, 0.55 mol) of methanesulfonyl chloride. The temperature of the reaction mixture during the addition is ca. 10°. The reaction mixture is then stirred for 1.5 hours at 10°. The reaction mixture is then diluted with dichloromethane, washed with ice water, cold 10% HCl, saturated KHCO3, saturated NaCl and dried (MgSO4). Solvent is removed in vacuo to yield 68 g (90%) of the isobutyl methanesulfonate as an oil.

Reference： [1]Current Patent Assignee: JINAN LEAD PHARM CHEMICAL; INNER MONGOLIA JINGDONG PHARMACEUTICAL - CN110790720, 2020, A Location in patent: Paragraph 0087-0090; 0118-0120
[2]Hansen, Dennis Jul; Manuguerra, Ilenia; Kjelstrup, Michael Brondum; Gothelf, Kurt Vesterager [Angewandte Chemie - International Edition, 2014, vol. 53, # 52, p. 14415 - 14418][Angew. Chem., 2014, vol. 126, # 52, p. 14643 - 14646,4]
[3]Raiguel, Stijn; Thomas, Joice; Binnemans, Koen; Dehaen, Wim [European Journal of Organic Chemistry, 2018, vol. 2018, # 35, p. 4850 - 4856]
[4]Pattison; Millington [Canadian Journal of Chemistry, 1956, vol. 34, p. 757,760] Williams; Mosher [Journal of the American Chemical Society, 1954, vol. 76, p. 2984,2986]
[5]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US4076825, 1978, A

4
[ 16156-53-9 ]
[ 83561-07-3 ]

Yield	Reaction Conditions	Operation in experiment
	In water at 18.9℃; pulse radiolysis, pH 4.5-5; fast hydrolysis of alkyl radicals with leaving groups in the β position;

Reference： [1]Koltzenburg, G.; Behrens, G.; Schulte-Frohlinde, S. [Journal of the American Chemical Society, 1982, vol. 104, # 25, p. 7311 - 7312]

5
[ 16156-53-9 ]
[ 86734-95-4 ]
[(2R,4R,5R)-5-(6-Amino-purin-9-yl)-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-hydroxy-tetrahydro-furan-3-yl]-methanesulfonic acid isobutyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium 1.) THF/hexane, -78 deg C, 20 min, 2.) THF/hexane, -78 deg C, 60 min; Yield given. Multistep reaction;

Reference： [1]Xie, Meiqiang; Widlanski, Theodore S. [Tetrahedron Letters, 1996, vol. 37, # 26, p. 4443 - 4446]

6
[ 16156-53-9 ]
[ 90813-54-0 ]
[(2R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-tetrahydro-furan-3-yl]-methanesulfonic acid isobutyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium 1.) THF/hexane, -78 deg C, 20 min, 2.) THF/hexane, -78 deg C, 60 min; Yield given. Multistep reaction;

Reference： [1]Xie, Meiqiang; Widlanski, Theodore S. [Tetrahedron Letters, 1996, vol. 37, # 26, p. 4443 - 4446]

7
[ 16156-53-9 ]
[ 142325-25-5 ]
3’-O-tert-butyldimethylsilyl-5’-deoxy-5’-((isobutyloxysulfonyl)methyl)thymidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: isobutyl methanesulfonate With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: 3’-O-tert-butyldimethylsilyl-5’-deoxy-5’-iodothymidine In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
	With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium 1.) THF/hexane, -78 deg C, 20 min, 2.) THF/hexane, -78 deg C, 60 min; Yield given. Multistep reaction;

Reference： [1]Hansen, Dennis Jul; Manuguerra, Ilenia; Kjelstrup, Michael Brondum; Gothelf, Kurt Vesterager [Angewandte Chemie - International Edition, 2014, vol. 53, # 52, p. 14415 - 14418][Angew. Chem., 2014, vol. 126, # 52, p. 14643 - 14646,4]
[2]Xie, Meiqiang; Widlanski, Theodore S. [Tetrahedron Letters, 1996, vol. 37, # 26, p. 4443 - 4446]

Yield	Reaction Conditions	Operation in experiment
	γ-Isotopeneffekt bei der Hydrolyse;

Yield	Reaction Conditions	Operation in experiment
	at 80℃; Geschwindigkeitkonstante der Solvolyse;

Yield	Reaction Conditions	Operation in experiment
	at 80℃; Geschwindigkeitkonstante der Solvolyse;

11
[ 16156-53-9 ]
[ 7722-84-1 ]
[ 5618-63-3 ]

Yield	Reaction Conditions	Operation in experiment
	at 25℃; Zeitlicher Verlauf des Alkali-Verbrauchs;

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

Yield	Reaction Conditions	Operation in experiment
97%
	Isobutanol, Mesylchlorid, NaOH, Phasentransferkatalysator;
	Isobutanol, Methylsulfonylchlorid (Pyridin/Eiskuehlung);

MsCl, i-BuOH <NEt3/Bzl.>;

13
[ 16156-53-9 ]
[ 407-38-5 ]
3,3,3-trifluoro-2-oxo-propane-1-sulfonic acid 2-methyl-propyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: isobutyl methanesulfonate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Stage #2: 2,2,2-trifluoroethyl trifluoroacetate In tetrahydrofuran at -78℃; for 0.166667h;

Reference： [1]Ye, Tao; Zhou, Congying [New Journal of Chemistry, 2005, vol. 29, # 9, p. 1159 - 1163]

14
[ 16156-53-9 ]
[ 67-64-1 ]
2-hydroxy-2-methyl-propane-1-iso-butylsulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	Stage #1: isobutyl methanesulfonate With n-butyllithium In tetrahydrofuran at -75℃; for 0.0833333h; Stage #2: acetone In tetrahydrofuran at 0℃; for 2h; Further stages.;

Reference： [1]Johnson II, David C.; Widlanski, Theodore S. [Tetrahedron Letters, 2004, vol. 45, # 46, p. 8483 - 8487]

15
[ 16156-53-9 ]
[ 151075-88-6 ]
[ 918900-74-0 ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: isobutyl methanesulfonate With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium In tetrahydrofuran; hexane at -94 - -78℃; for 0.166667h; Stage #2: benzyl 2,3,4-tri-O-benzyl-6-O-trifluoromethanesulfonyl-β-D-glucopyranoside In tetrahydrofuran; hexane at -78℃; for 0.25h;

Reference： [1]Navidpour, Latifeh; Lu, Wallach; Taylor, Scott D. [Organic Letters, 2006, vol. 8, # 24, p. 5617 - 5620]

16
[ 16156-53-9 ]
[ 918900-75-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: n-BuLi; HMPA / tetrahydrofuran; hexane / 0.17 h / -94 - -78 °C 1.2: 75 percent / tetrahydrofuran; hexane / 0.25 h / -78 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C 2.2: 52 percent / N-fluorobenzenesulfonimide / tetrahydrofuran; hexane / 0.25 h / -78 °C

Reference： [1]Navidpour, Latifeh; Lu, Wallach; Taylor, Scott D. [Organic Letters, 2006, vol. 8, # 24, p. 5617 - 5620]

17
[ 16156-53-9 ]
[ 918900-76-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: n-BuLi; HMPA / tetrahydrofuran; hexane / 0.17 h / -94 - -78 °C 1.2: 75 percent / tetrahydrofuran; hexane / 0.25 h / -78 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C 2.2: 17 percent / N-fluorobenzenesulfonimide / tetrahydrofuran; hexane / 0.25 h / -78 °C

Reference： [1]Navidpour, Latifeh; Lu, Wallach; Taylor, Scott D. [Organic Letters, 2006, vol. 8, # 24, p. 5617 - 5620]

18
[ 16156-53-9 ]
[ 120263-47-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C 1.2: tetrahydrofuran / 0.17 h / -78 °C 2.1: 4-acetamidobenzenesulfonyl azide; Et₃N; water / acetonitrile / 20 °C

Reference： [1]Ye, Tao; Zhou, Congying [New Journal of Chemistry, 2005, vol. 29, # 9, p. 1159 - 1163]

19
[ 16156-53-9 ]
(trans)-2-methylpropyl 2-phenylcyclopropanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C 1.2: tetrahydrofuran / 0.17 h / -78 °C 2.1: 4-acetamidobenzenesulfonyl azide; Et₃N; water / acetonitrile / 20 °C 3.1: Rh₂(OAc)4 / CH₂Cl₂ / 3 h

Reference： [1]Ye, Tao; Zhou, Congying [New Journal of Chemistry, 2005, vol. 29, # 9, p. 1159 - 1163]

20
[ 16156-53-9 ]
(cis)-2-methylpropyl 2-phenylcyclopropanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C 1.2: tetrahydrofuran / 0.17 h / -78 °C 2.1: 4-acetamidobenzenesulfonyl azide; Et₃N; water / acetonitrile / 20 °C 3.1: Rh₂(OAc)4 / CH₂Cl₂ / 3 h

Reference： [1]Ye, Tao; Zhou, Congying [New Journal of Chemistry, 2005, vol. 29, # 9, p. 1159 - 1163]

21
[ 16156-53-9 ]
[ 852459-63-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: BuLi / tetrahydrofuran / 0.08 h / -75 °C 1.2: 96 percent / tetrahydrofuran / 2 h / 0 °C 2.1: 98 percent / Ag₂O; calcium sulfate / 120 h

Reference： [1]Johnson II, David C.; Widlanski, Theodore S. [Tetrahedron Letters, 2004, vol. 45, # 46, p. 8483 - 8487]

22
[ 16156-53-9 ]
[(2R,4R,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yl]-methanesulfonic acid isobutyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) n-BuLi, HMPA / 1.) THF/hexane, -78 deg C, 20 min, 2.) THF/hexane, -78 deg C, 60 min 2: 1.) SOCl₂, pyridine, 2.) 90percent TFA, 3.) NaBH₄ / 3.) EtOH

Reference： [1]Xie, Meiqiang; Widlanski, Theodore S. [Tetrahedron Letters, 1996, vol. 37, # 26, p. 4443 - 4446]

23
[ 16156-53-9 ]
[(2R,4R,5R)-5-(6-Amino-purin-9-yl)-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yl]-methanesulfonic acid isobutyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) n-BuLi, HMPA / 1.) THF/hexane, -78 deg C, 20 min, 2.) THF/hexane, -78 deg C, 60 min 2: 1.) SOCl₂, pyridine, 2.) 90percent TFA, 3.) NaBH₄ / 3.) EtOH

Reference： [1]Xie, Meiqiang; Widlanski, Theodore S. [Tetrahedron Letters, 1996, vol. 37, # 26, p. 4443 - 4446]

24
[ 16156-53-9 ]
[ 54029-45-7 ]
4-(2-methylpropyl)sulfonyl-2-nitroaniline [ No CAS ]
[ 66868-67-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium borohydrid; In N-methyl-acetamide;	(2) Preparation of 4-(2-methylpropyl)sulfonyl-2-nitroaniline To a solution of 19.5 g (0.1 mol) <strong>[54029-45-7]4-thiocyano-2-nitroaniline</strong> in 130 ml dimethylformamide is added 3.78 g (0.1 mol) sodium borohydride, all at once. The mixture is stirred for 1/2 hour, then 15.2 g (0.1 mol) 2-methylpropylmethanesulfonate in 70 ml dimethylformamide is added. The solution is stirred at 30 for 3 hours, cooled and partitioned between water and dichloromethane. The layers are separated and the aqueous phase reextracted with dichloromethane. The organic phases are combined, washed with aqueous K2 CO3, water and saturated NaCl, dried, filtered and stripped to yield a red solid which is crystallized from ether/petroleum ether to yield 14.4 g of solid which is recrystallized from cyclohexane to yield 13.1 g of 4-(2-methylpropyl)sulfenyl-2-nitroaniline in the form of brilliant red crystals, m.p. 56.5-58.5, 58%.

Reference： [1]Patent: US4076825,1978,A

25
[ 1001085-19-3 ]
[ 16156-53-9 ]
[ 1231683-81-0 ]
C₂₂H₃₆N₆O₉S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	Stage #1: isobutyl methanesulfonate With n-butyllithium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: 3-azido-3-deoxy-1,2-O-isopropylidene-5-O-trifluoromethanesulfonyl-α-D-ribofuranose In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane at -78℃; for 2h; Inert atmosphere; Stage #3: With acetic acid In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane

Reference： [1]Location in patent: experimental part van Ameijde, Jeroen; Slot, Thierry K.; Liskamp, Rob M.J. [Tetrahedron Asymmetry, 2010, vol. 21, # 4, p. 469 - 475]

26
[ 16156-53-9 ]
[ 814-49-3 ]
[ 1236148-14-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: isobutyl methanesulfonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.333333h; Inert atmosphere; Stage #2: diethyl chlorophosphate In tetrahydrofuran; hexane at -78 - -50℃; Inert atmosphere;

Reference： [1]Franchini, Laura; Compostella, Federica; Colombo, Diego; Panza, Luigi; Ronchetti, Fiamma [Journal of Organic Chemistry, 2010, vol. 75, # 15, p. 5363 - 5366]

27
[ 16156-53-9 ]
[ 1352399-56-4 ]
[ 1352399-57-5 ]

Yield	Reaction Conditions	Operation in experiment
56%	Stage #1: isobutyl methanesulfonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: 1-(3-bromopropyl)-1,4-cyclohexadiene In tetrahydrofuran; hexane at -78 - 20℃; for 20h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Virboul, Morgane A.N.; Gebbink, Robertus J.M. Klein [Organometallics, 2012, vol. 31, # 1, p. 85 - 91]

28
[ 16156-53-9 ]
2-hydroxy-2-methylpropyl methanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%	With peracetic acid; [2,2]bipyridinyl; manganese(II) triflate; potassium hydroxide In water; acetic acid at 20℃; for 0.025h;

Reference： [1]Adams, Ashley M.; Du Bois; Malik, Hasnain A. [Organic Letters, 2015, vol. 17, # 24, p. 6066 - 6069]

29
[ 111992-18-8 ]
[ 16156-53-9 ]
[ 122836-35-5 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: 2-(5-amino-2,4-dichlorophenyl)-4-(difluoromethyl)-2,4-dihydro-5-methyl-3H-1,2,4-triazol-3-one With chloro(dimethyl)sulfonium chloride In dichloromethane at 0 - 5℃; for 0.5h; Stage #2: isobutyl methanesulfonate In dichloromethane at 0 - 5℃; for 10h;	19 Example 3 General procedure: Into a 250ml four-necked flask, 15.6 g (0.05mol) of triazolinone aniline is dissolved in 50g of dichloromethane, cool down at 0-5 ° C, and add the catalyst of Example 1, the mass of dimethyl chloride Chlorosulfur is 5% of the mass of the triazolinone aniline, stir for 30min; after that at this temperature added the drops of Methyl methanesulfonate 6.7g, after completion of the drop-wise addition, the reaction is stirred at this temperature for 3 hours after that the raw materials are basically completely reacted; the reaction solution is cooled at 0 ° C, suction filtered, dried, obtained 19.3 g of Sulfentrazone solid, the content detected by HPLC is 99.1%, yield is 98.8%. Distillation of the mother liquor obtained by filtration, Dichloromethane and methanol were recovered in sections.

Reference： [1]Current Patent Assignee: SHANDONG RAINBOW INVESTMENT CO., LTD. - CN108424395, 2018, A Location in patent: Paragraph 0029; 0045

30
[ 16156-53-9 ]
5-ethyl-4-methyl-1-(2-methylpropyl)-1,2,3-triazole [ No CAS ]
C₁₃H₂₆N₃⁽¹⁺⁾*CH₃O₃S^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In toluene at 100℃; for 48h;

Reference： [1]Raiguel, Stijn; Thomas, Joice; Binnemans, Koen; Dehaen, Wim [European Journal of Organic Chemistry, 2018, vol. 2018, # 35, p. 4850 - 4856]

31
[ 16156-53-9 ]
[ 359-00-2 ]
[ 2088-35-9 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: isobutyl methanesulfonate With potassium fluoride In diethylene glycol at 95℃; for 7.5h; Inert atmosphere; Stage #2: With chloroform; N-benzyl-N,N,N-triethylammonium chloride; potassium hydroxide In water at 0 - 20℃; for 8.5h;	15; 16 Example 15 A 1 L glass reaction vessel equipped with a stirrer, a dropping funnel, a fraction collection receiver, and a Dimroth condenser was charged with 116 g of spray-dried potassium fluoride (produced by Sigma-Aldrich) and 800 mL of diethylene glycol. A nitrogen atmosphere was provided in the glass reaction vessel. The reaction vessel was immersed in an oil bath and was heated to 95° C. Thereafter, 152 g of methanesulfonyloxyisobutane was added into the reaction vessel over approximately 3.5 hours from the dropping funnel. After this addition, stirring was continued for 4 hours at 95° C., and produced low-boiling point product was collected in the fraction collection receiver, which was immersed in a dry ice/ethanol bath. Thereafter, the temperature of the oil bath was lowered to 80° C., and two glass traps immersed in a dry ice/ethanol bath were connected to the reaction vessel in series. In addition, a pressure controller and a vacuum pump were connected to an outlet of the glass traps. The vacuum pump was operated, the pressure in the system was lowered stepwise to 50 kPa to 45 kPa, followed by 35 kPa to 30 kPa, and then 30 kPa to 25 kPa using the pressure controller, and volatile components were recovered in the glass traps. (0112) The contents of the fraction collection receiver and the two glass traps were combined and then analyzed by gas chromatography. The mixture (49 g) was found to contain 11.85 area % of isobutene, 79.69 area % of isobutyl fluoride, 7.32 area % of diisopropyl ether, and 1.14 area % of high-boiling point components. When this mixture was distilled using a simple distillation apparatus equipped with a short column, 41 g of a mixture containing 14.02 area % of isobutene and 85.36 area % of isobutyl fluoride was obtained.; A 100 mL glass reaction vessel equipped with a stirrer and a Dimroth condenser (-10° C. coolant circulated in condenser) was charged with 3.3 g of potassium hydroxide (purity: 85%) and was cooled to 0° C. The reaction vessel was further charged with 2.3 g of water to dissolve the potassium hydroxide. Next, 10 mL of chloroform was added as trihalomethane. In addition, 10.3 g of the mixture obtained in Production Example 3 (crude isobutyl fluoride containing isobutene) and 0.11 g of benzyltriethylammonium chloride as a phase transfer catalyst were added. The organic layer was analyzed by gas chromatography at this point and was found to contain 14.10 area % of isobutene, 68.13 area % of isobutyl fluoride, and 17.54 area % of chloroform. (0135) The contents of the reaction vessel were vigorously stirred for 30 minutes at 0° C. and were further stirred for 8 hours at room temperature. Thereafter, the stirring was stopped, the contents were allowed to settle, and the organic layer was reanalyzed by gas chromatography. In this analysis, 1.82 area % of isobutene, 70.30 area % of isobutyl fluoride, and 13.84 area % of chloroform were detected, and production of 13.73 area % of dichlorocyclopropane derivative was confirmed in a high retention time region.

Reference： [1]Current Patent Assignee: ZEON CORPORATION - US2019/177253, 2019, A1 Location in patent: Paragraph 0111; 0112;

32
[ 16156-53-9 ]
[ 359-00-2 ]
[ 115-11-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium fluoride In diethylene glycol at 95℃; for 7.5h; Inert atmosphere; Overall yield = 49 g;	3 Production Example 3 A 1 L glass reaction vessel equipped with a stirrer, a dropping funnel, a fraction collection receiver, and a Dimroth condenser was charged with 116 g of spray-dried potassium fluoride (produced by Sigma-Aldrich) and 800 mL of diethylene glycol. A nitrogen atmosphere was provided in the glass reaction vessel. The reaction vessel was immersed in an oil bath and was heated to 95° C. Thereafter, 152 g of methanesulfonyloxyisobutane was added into the reaction vessel over approximately 3.5 hours from the dropping funnel. After this addition, stirring was continued for 4 hours at 95° C., and produced low-boiling point product was collected in the fraction collection receiver, which was immersed in a dry ice/ethanol bath. Thereafter, the temperature of the oil bath was lowered to 80° C., and two glass traps immersed in a dry ice/ethanol bath were connected to the reaction vessel in series. In addition, a pressure controller and a vacuum pump were connected to an outlet of the glass traps. The vacuum pump was operated, the pressure in the system was lowered stepwise to 50 kPa to 45 kPa, followed by 35 kPa to 30 kPa, and then 30 kPa to 25 kPa using the pressure controller, and volatile components were recovered in the glass traps. (0112) The contents of the fraction collection receiver and the two glass traps were combined and then analyzed by gas chromatography. The mixture (49 g) was found to contain 11.85 area % of isobutene, 79.69 area % of isobutyl fluoride, 7.32 area % of diisopropyl ether, and 1.14 area % of high-boiling point components. When this mixture was distilled using a simple distillation apparatus equipped with a short column, 41 g of a mixture containing 14.02 area % of isobutene and 85.36 area % of isobutyl fluoride was obtained.

Reference： [1]Current Patent Assignee: ZEON CORPORATION - US2019/177253, 2019, A1 Location in patent: Paragraph 0111; 0112

33
[ 16156-53-9 ]
[ 606926-42-5 ]
C₁₆H₂₃NO₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With 2,2':6,2''-terpyridine; manganese; sodium iodide In N,N-dimethyl acetamide at 100℃; for 12h;

Reference： [1]Duan, Jicheng; Du, Yun-Fei; Pang, Xiaobo; Shu, Xing-Zhong [Chemical Science, 2019, vol. 10, # 37, p. 8706 - 8712]

34
[ 16156-53-9 ]
[ 161798-01-2 ]
[ 161798-03-4 ]

Yield	Reaction Conditions	Operation in experiment
85.5%	With potassium carbonate In N,N-dimethyl-formamide at 95 - 100℃;	10; 13 Example 10 Synthesis of 2- (3-formyl-4-isobutoxyphenyl) -4-methyl-5-thiazolecarboxylic acid ethyl ester, ie, 152A4-00 Add 120 g of DMF to the reaction flask, and add 30 g (103.0 mmol) of 152A3-00.Add 17 g (123.0 mmol) of anhydrous potassium carbonate, and then add 17 g (111.7 mmol) of isobutyl mesylate (152H1-Ms) prepared in Example 7; heat to 95-100 ° C,Incubate the reaction for 3 to 5 hours; after the reaction is completed, cool to 30 to 40 ° C; add 500 g of water to the reaction system, cool to 10 to 15 ° C, and incubate for about 2 to 3 hours. Filter, rinse the filter cake with the appropriate amount of ethanol, collect the solids,Drying gives about 30.6 g of 152A4-00 dry product (theoretical amount: 35.78 g). The yield was 85.5%.

Reference： [1]Current Patent Assignee: JINAN LEAD PHARM CHEMICAL; INNER MONGOLIA JINGDONG PHARMACEUTICAL - CN110790720, 2020, A Location in patent: Paragraph 0102-0104; 0118-0121

35
oleyl iodide [ No CAS ]
[ 16156-53-9 ]
isobutyl (10Z)-nonadecenesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	Stage #1: isobutyl methanesulfonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: oleyl iodide In tetrahydrofuran; hexane at -78 - 20℃; for 16h; Inert atmosphere;	1 Isobutyl (10Z)-nonadecenesulfonate In adaptation of a procedure (M. Xie, T. S. Widlanski, Tetrahedron Lett.1996, 37, 4443), n-BuLi solution (6.52 mL of 1.15 M in hexanes, 7.50 mmol, 1.50 equiv.) was added to a -78 °C 9:1 THF/DMPU (15 mL) solution of isobutyl methanesulfonate (1.22 g, 8.00 mmol, 1.60 equiv.) in a round bottom flask under argon and the resultant allowed to stir for 30 min. While still at ^78 °C, a THF (2 mL) solution of oleyl iodide (1.89 g, 5.00 mmol, 1.00 equiv.) was added to the above solution and the reaction mixture was allowed to warm up over 16 h. The reaction mixture was quenched with aqueous 10% citric acid, extracted with Et2O (2×10 mL) and the combined organics washed with water (1×10 mL), brine (1×10 mL), then dried over Na2SO4 and concentrated on a rotary evaporator. The crude residue was purified by flash column chromatography (98:295:5 hexanes/EtOAc) to afford the alkylated sulfonate (1.19 g, 46% yield) as a clear, colourless oil. 1H (300 MHz, CDCl3): 5.46-5.27 (m, 2H), 4.00 (d, J = 6.6 Hz, 2H), 3.14-3.05 (m, 2H), 2.11-1.94 (m, 5H), 1.94-1.80 (m, 2H), 1.51-1.18 (m, 26 H), 1.00 (t, J = 6.8 Hz, 6H), 0.90 (br t, J = 6.6 Hz, 3H).

Reference： [1]Current Patent Assignee: UNIVERSITY OF BRITISH COLUMBIA; INTEGRATED NANOTHERAPEUTICS - WO2021/26647, 2021, A1 Location in patent: Page/Page column 61

36
[ 16156-53-9 ]
isobutyl 10,11-dihydroxynonadecanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 16 h / -78 - 20 °C / Inert atmosphere 2.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / acetone; water / 16 h / 20 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: UNIVERSITY OF BRITISH COLUMBIA; INTEGRATED NANOTHERAPEUTICS - WO2021/26647, 2021, A1

37
[ 16156-53-9 ]
isobutyl 10,11-bis(2-hexyldecanoyloxy)nonadecanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 16 h / -78 - 20 °C / Inert atmosphere 2.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / acetone; water / 16 h / 20 °C / Inert atmosphere 3.1: dicyclohexyl-carbodiimide / dichloromethane / 0.25 h / Cooling with ice; Inert atmosphere 3.2: 16 h / 20 °C / Cooling with ice; Inert atmosphere

Reference： [1]Current Patent Assignee: UNIVERSITY OF BRITISH COLUMBIA; INTEGRATED NANOTHERAPEUTICS - WO2021/26647, 2021, A1

38
[ 78-83-1 ]
[ 7143-01-3 ]
[ 16156-53-9 ]

Yield	Reaction Conditions	Operation in experiment
77%	With triethylamine In dichloromethane at 0 - 20℃; for 12h; Inert atmosphere;

Reference： [1]Zhang, Feng; Wang, Yang; Wang, Yi; Pan, Yi [Organic Letters, 2021, vol. 23, # 19, p. 7524 - 7528]

39
[ 696-63-9 ]
[ 16156-53-9 ]
isobutyl(4-methoxyphenyl)sulfane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; tetrabutylammonium acetate In N,N-dimethyl acetamide at 20℃; for 2h; Glovebox; Electrochemical reaction; Inert atmosphere; chemoselective reaction;

Reference： [1]Zhang, Feng; Wang, Yang; Wang, Yi; Pan, Yi [Organic Letters, 2021, vol. 23, # 19, p. 7524 - 7528]

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P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
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P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
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P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
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P308	IF exposed or concerned:
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P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
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P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
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P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
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Storage
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P401
P402	Store in a dry place.
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Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	Inquiry	{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]}	{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price) ]}	{[ item.pr_usastock ]}		{[ item.pr_chinastock ]}	{[ item.pr_remark ]}

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
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H351	Suspected of causing cancer
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H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ 16156-53-9 ] Synthesis Path-Downstream 1~39

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