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Chemical Structure| 205865-67-4 Chemical Structure| 205865-67-4
Chemical Structure| 205865-67-4

*Storage: Keep in dark place,Inert atmosphere,2-8°C.

Ethyl 2,2-difluoro-2-(trimethylsilyl)acetate

CAS No.: 205865-67-4

4.5 *For Research Use Only !

Cat. No.: A735037 Purity: 97%

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Product Details of [ 205865-67-4 ]

CAS No. :205865-67-4
Formula : C7H14F2O2Si
M.W : 196.27
SMILES Code : O=C(OCC)C(F)(F)[Si](C)(C)C
MDL No. :MFCD04973092
InChI Key :DYAKYYSMROBYNG-UHFFFAOYSA-N
Pubchem ID :2758940

Safety of [ 205865-67-4 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225-H315-H318-H335
Precautionary Statements:P261-P305+P351+P338
Class:3(8)
UN#:2924
Packing Group:

Application In Synthesis [ 205865-67-4 ]

* 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 [ 205865-67-4 ]

[ 205865-67-4 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 75-77-4 ]
  • [ 383-62-0 ]
  • [ 205865-67-4 ]
  • 4-chloro-3-ethoxy-2,2,4,4-tetrafluoro-3-trimethylsilanyloxy-butyric acid ethyl ester [ No CAS ]
  • 2
  • [ 75-77-4 ]
  • [ 383-62-0 ]
  • [ 205865-67-4 ]
YieldReaction ConditionsOperation in experiment
70% With magnesium; In N,N-dimethyl-formamide; at 20℃; for 1.5h;Inert atmosphere; According to the following procedure, alpha- (trimethylsilyl) difluoroacetic acid ethyl ester (also referred to as difluorotrimethylsilanylacetic acid ethyl ester) (compound 2a) was prepared. Under a nitrogen atmosphere in a two-neck reaction tube,Magnesium (972.4 mg, 40.0 mmol), chlorotrimethylsilane (8.691 g, 80.0 mmol) and DMF (60 mL) were injected.Ethyl chlorodifluoroacetate (793 mg, 20.0 mmol) was added thereto,And the mixture was stirred at room temperature for 1.5 hours. The reaction mixture was extracted with diethyl ether,After washing with water, DMF was completely removed,The organic layer was dried over anhydrous sodium sulfate.Anhydrous sodium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by Kugel distillation (91 mmHg, 110 C.) to obtain alpha- (trimethylsilyl) difluoroacetic acid ethyl ester (Me 3 Si - CF 2 CO 2 Et; Compound 2a) (2.729 g, yield: 70%).
43% With magnesium; In N,N-dimethyl-formamide; at 20℃; for 1.5h;Inert atmosphere; Example 1Production of alpha-silyl difluoroacetic acid ester (1) According to the above-described scheme, magnesium (243 mg, 10.0 mmol), chlorotrimethylsilane (Me3SiCl; 2.17 g, 20.0 mmol) and DMF (15 mL) were put into a two-neck reaction tube under nitrogen atmosphere. Ethyl chlorodifluoroacetate (Compound 3; 793 mg, 624 muL, 5.0 mmol) was added thereto with the reaction container being cooled in water bath, and then the mixture was stirred at room temperature for 1.5 hours. The reaction mixture was extracted with diethyl ether and washed with water, and an organic layer was dried with anhydrous sodium sulfate. Diethyl ether was distilled away under reduced pressure, and by carrying out the production by silica gel column chromatography, difluorotrimethylsilanylacetic acid ethyl ester (Compound 3a) was obtained with a yield of 43%.Note that in other working examples, as difluorotrimethylsilanylacetic acid ethyl ester (Me3Si-CF2CO2Et; Compound 3a), the product obtained in this working example was used.The results of instrumental analysis of the product (Compound 3a) are shown below:1H-NMR (CDCl3, TMS) delta4.32 (2H, q, J=7.0 Hz), 1.35 (3H, t, J=7.0 Hz), 0.237 (9H, s) 19F-NMR (CDCl3, C6F6) delta38.5 (2F, s) Mass m/e: (m/z) (%) 181 (6), 153 (10), 125 (6), 103 (8), 77 (26), 73 (100)
43% With magnesium; In N,N-dimethyl-formamide; at 20℃; for 1.5h;Inert atmosphere; Cooling with ice; In accordance with the above scheme, magnesium (243 mg, 10.0 mmol), chlorotrimethylsilane (Me 3 SiCl; 2.17 g, 20.0 mmol) and DMF (15 mL) are placed in a two-neck reaction tube under a nitrogen atmosphere. While cooling the reaction vessel with a water bath, <strong>[383-62-0]ethyl chlorodifluoroacetate</strong> (Compound 3; 793 mg, 624 muL, 5.0 mmol) was added, followed by stirring at room temperature for 1.5 hours. The reaction mixture was extracted with diethyl ether, washed with water, and the organic layer was dried over anhydrous sodium sulfate. Distilling off diethyl ether under reduced pressure and purifying by silica gel column chromatography yielded ethyl difluorotrimethylsilanylacetate in a yield of 43%
  • 3
  • [ 77332-79-7 ]
  • [ 205865-67-4 ]
  • 2-(3-chloropyridin-4-yl)-2,2-difluoroacetic acid ethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With potassium fluoride; copper(l) iodide; In dimethyl sulfoxide; at 60℃; for 15h;Schlenk technique; Inert atmosphere; 2- (3-chloropyridin-4-yl) -2,2-difluoroacetic acid ethyl ester (compound 3c) was prepared according to the following procedure. In the Schlenk tube,3 - Chloro - 4 - iodopyridine (119.7 mg, 0.5 mmol), copper (I) iodide (190.5 mg, 1.0 mmol), potassium fluoride (58.1 mg, 1.0 mmol) and DMSO (2.0 mL).Finally, alpha- (trimethylsilyl) difluoroacetic acid ethyl ester (Compound 2a) (196.3 mg, 1.0 mmol) was added,Under a nitrogen atmosphere,And the mixture was stirred at 60 C. for 15 hours.After the reaction, trifluoroethanol (50.0 mg, 0.5 mmol) was added as an internal standard,As a result of measurement by 19 F-NMR, it was found that the objective product 2- (3-chloropyridin-4-yl) -2,2-difluoroacetic acid ethyl ester (compound 3c) was produced in 72% yield It was. The reaction mixture was extracted with ethyl acetate, washed with water and dried over anhydrous sodium sulfate. Anhydrous sodium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (Hexane: EtOAc = 30: 1, 20: 1, 20: 1) to give 2- (3-chloropyridin-4-yl) -2,2-difluoroacetic acid ethyl ester (Compound 3c) (70.8 mg, 0.30 mmol, yield: 60%).
 

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