Ethyl O-mesitylsulfonylacetohydroxamate Chemical Properties

Melting point:

54-56 °C (lit.) 54-58 °C

Boiling point:

381.7±52.0 °C(Predicted)

Density 

1.2483 (rough estimate)

refractive index 

1.6800 (estimate)

storage temp. 

2-8°C

form 

powder to crystal

color 

White to Almost white

Water Solubility 

Insoluble

BRN 

2144156

InChI

InChI=1S/C13H19NO4S/c1-6-17-12(5)14-18-19(15,16)13-10(3)7-9(2)8-11(13)4/h7-8H,6H2,1-5H3

InChIKey

KQCBSWBQAXTILK-UHFFFAOYSA-N

SMILES

C(=NOS(C1=C(C)C=C(C)C=C1C)(=O)=O)(OCC)C

Safety Information

Safety Statements 

24/25

WGK Germany 

3

F 

6-9-21

HS Code 

29252900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Ethyl O-mesitylsulfonylacetohydroxamate Usage And Synthesis

Chemical Properties

white to light yellow crystalline powder

Synthesis Reference(s)

The Journal of Organic Chemistry, 38, p. 1239, 1973 DOI: 10.1021/jo00946a045

Synthesis

Ethyl N-hydroxyacetimidate (2.00 g, 19.4 mmol), N,N-diisopropylethylamine (3.01 g, 23.3 mmol), and 4-dimethylaminopyridine (240 mg, 1.96 mmol) were dissolved in anhydrous dichloromethane (30 mL) and the solution was cooled to 0°C. To the cooled solution was slowly added, with stirring, 2,4,6 -trimethylbenzene-1-sulfonyl chloride (4.66 g, 21.3 mmol) to the cooled solution. The reaction mixture was gradually warmed to room temperature and stirring was continued for 1 hour. Upon completion of the reaction, the reaction was quenched by the addition of water (40 mL) and subsequently extracted with dichloromethane (30 mL, 3 times). The organic layers were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel fast column chromatography using a hexane solution of 5% ethyl acetate as eluent to afford ethyl O-(2,4,6-trimethylbenzenesulfonyl)acetohydroxamic acid as a white solid (5.19 g, 94% yield). The product was characterized by 1H NMR (400 MHz, CDCl3), 13C NMR (101 MHz, CDCl3) and HRMS (ESI/TOF), and the data were consistent with the expected structure.

References

[1] RSC Advances, 2018, vol. 8, # 25, p. 13755 - 13763
[2] Synthetic Communications, 2018, vol. 48, # 6, p. 626 - 631
[3] Patent: WO2011/112186, 2011, A1. Location in patent: Page/Page column 202
[4] Patent: CN108530315, 2018, A. Location in patent: Paragraph 0100-0102
[5] Journal of Heterocyclic Chemistry, 2007, vol. 44, # 6, p. 1383 - 1387

Ethyl O-mesitylsulfonylacetohydroxamate(38202-27-6)Related Product Information

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• Ethylbenzene
• CHLOROETHANE
• Ethyl acetate
• Ethanol
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• Ethyl 2,4-dioxovalerate
• 2,3-Butanedione monoxime
• Ethyl formate
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