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  • 4-Fluoro-1,3-dioxolan-2-one CAS 114435-02-8 Fluoroethylene carbonate CAS no 114435-02-8 1,3-Dioxolan-2-one,4-fluoro-

    Cas No: 114435-02-8

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114435-02-8 Usage

Chemical Properties

Colorless liquid

Uses

4-Fluoro-1,3-dioxolan-2-one is used as an electrolyte additive in lithium ion batteries. It also enables the formation of thin, smooth and stable passive solid electrolyte interphase (SEI) layer, which increases the cycling efficiency and discharge capacity retention of the secondary battery. Further, it is used as an intermediate in organic synthesis.

Preparation

The preparation of Fluoroethylene carbonate is as follows:Add 114g of liquid ethylene carbonate at 50, 1.14g of palladium acetate (II) and 114g of dry acetonitrile (water 100ppm) to a 500ml Monel reactor containing the monophenyl iodine difluoride prepared in step (1) , Stir at 50°C for 0.5h, raise the temperature to 70°C and react for 5h (the molar ratio of ethylene carbonate to hydrogen fluoride in step (1) is 1.1:2.5, the molar ratio of ethylene carbonate to acetonitrile is 1.1:2.8, palladium acetate (II) The dosage is 1.0% of the mass of ethylene carbonate). The tail gas during the reaction was absorbed by potassium hydroxide solution with a mass fraction of 10%. After the reaction, vacuum distillation was carried out under the condition of 3mmHg. The 65-71°C fraction was collected to obtain 103.3g of fluoroethylene carbonate with a GC content of 99.3%. The yield of FEC was 75%.

General Description

Fluoroethylene carbonate (FEC) can be used as a co-solvent for the formation of electrolytes, which can exhibit a reversible capacity of 2.5 Ah g?1. It can be further used in the fabrication of lithium-ion batteries. FEC enables the formation of thin, smooth and stable passive solid electrolyte interphase (SEI) layer, which is insoluble in the electrolyte, in turn increasing the cycling efficiency and discharge capacity retention of the secondary battery.

Flammability and Explosibility

Notclassified

Check Digit Verification of cas no

The CAS Registry Mumber 114435-02-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,4,4,3 and 5 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 114435-02:
(8*1)+(7*1)+(6*4)+(5*4)+(4*3)+(3*5)+(2*0)+(1*2)=88
88 % 10 = 8
So 114435-02-8 is a valid CAS Registry Number.
InChI:InChI=1/C3H3FO3/c4-2-1-6-3(5)7-2/h2H,1H2

114435-02-8 Well-known Company Product Price

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  • Alfa Aesar

  • (H61502)  4-Fluoro-1,3-dioxolan-2-one, 98%   

  • 114435-02-8

  • 25g

  • 1493.0CNY

  • Detail
  • Alfa Aesar

  • (H61502)  4-Fluoro-1,3-dioxolan-2-one, 98%   

  • 114435-02-8

  • 100g

  • 4788.0CNY

  • Detail
  • Aldrich

  • (757349)  Fluoroethylene carbonate Green Alternative  99%

  • 114435-02-8

  • 757349-25G

  • 6,089.85CNY

  • Detail

114435-02-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-Fluoro-1,3-dioxolan-2-one

1.2 Other means of identification

Product number -
Other names 4-Fluoro-1,3-Dioxolan-2-One

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:114435-02-8 SDS

114435-02-8Synthetic route

[1,3]-dioxolan-2-one
96-49-1

[1,3]-dioxolan-2-one

4-fluoro-1,3-dioxolane-2-one
114435-02-8

4-fluoro-1,3-dioxolane-2-one

Conditions
ConditionsYield
With N-fluorobis(benzenesulfon)imide at 120℃; for 0.5h; Reagent/catalyst; Sealed tube;98.2%
With fluorine at 5℃; Electrolysis;94%
With fluorine at 50℃;70%
4-chloro-1,3-dioxolan-2-one
3967-54-2

4-chloro-1,3-dioxolan-2-one

4-fluoro-1,3-dioxolane-2-one
114435-02-8

4-fluoro-1,3-dioxolane-2-one

Conditions
ConditionsYield
With potassium fluoride; 5,11,17,23,29,35-hexakis(tert-butyl)-37,38,39,40,41-hexakis(hydroxy)calix[6]arene; carbonic acid dimethyl ester at 60℃; for 1.5h; Reagent/catalyst; Temperature;95.6%
With triethylamine tris(hydrogen fluoride); triethylamine In ethyl acetate at 80℃; for 1h; Product distribution / selectivity;70%
[1,3]-dioxolan-2-one
96-49-1

[1,3]-dioxolan-2-one

cis-4,5-difluoroethylene carbonate

cis-4,5-difluoroethylene carbonate

trans-4,5-difluoro-1,3-dioxolane-2-one

trans-4,5-difluoro-1,3-dioxolane-2-one

C

4-fluoro-1,3-dioxolane-2-one
114435-02-8

4-fluoro-1,3-dioxolane-2-one

D

4,4-difluoro-1,3-dioxolan-2-one

4,4-difluoro-1,3-dioxolan-2-one

Conditions
ConditionsYield
With fluorine at 45 - 55℃; under 73.5576 Torr; Product distribution / selectivity;A n/a
B n/a
C 78.4%
D n/a
With fluorine at 23.9 - 31.2℃; under 15.0015 Torr; Inert atmosphere;
4-(p-chlorophenylthio)-1,3-dioxolan-2-one
304881-41-2

4-(p-chlorophenylthio)-1,3-dioxolan-2-one

4-fluoro-1,3-dioxolane-2-one
114435-02-8

4-fluoro-1,3-dioxolane-2-one

Conditions
ConditionsYield
With triethylamine pentahydrogen fluoride salt In dichloromethane at 20℃; Electrolysis; Pt electrodes;75%
4-(p-chlorophenylthio)-1,3-dioxolan-2-one
304881-41-2

4-(p-chlorophenylthio)-1,3-dioxolan-2-one

A

4-fluoro-1,3-dioxolane-2-one
114435-02-8

4-fluoro-1,3-dioxolane-2-one

B

4-fluoro-4-(p-chlorophenylthio)-1,3-dioxolan-2-one

4-fluoro-4-(p-chlorophenylthio)-1,3-dioxolan-2-one

Conditions
ConditionsYield
With tetraethylammonium fluoride In 1,2-dimethoxyethane at 20℃; Electrolysis; Pt electrodes;A 20 % Spectr.
B 70%
With tetraethylammonium fluoride In 1,2-dimethoxyethane at 20℃; Product distribution; Further Variations:; Reagents; Solvents; Fluorination; Electrolysis;A 20 % Spectr.
B 80 % Spectr.
4-(p-bromophenylthio)-1,3-dioxolan-2-one
398490-68-1

4-(p-bromophenylthio)-1,3-dioxolan-2-one

A

4-fluoro-1,3-dioxolane-2-one
114435-02-8

4-fluoro-1,3-dioxolane-2-one

B

4-fluoro-4-(p-bromophenylthio)-1,3-dioxolan-2-one

4-fluoro-4-(p-bromophenylthio)-1,3-dioxolan-2-one

Conditions
ConditionsYield
With tetraethylammonium fluoride In 1,2-dimethoxyethane at 20℃; Electrolysis; Pt electrodes;A 4 % Spectr.
B 66%
4-phenylthio-1,3-dioxolane-2-one

4-phenylthio-1,3-dioxolane-2-one

A

4-fluoro-1,3-dioxolane-2-one
114435-02-8

4-fluoro-1,3-dioxolane-2-one

B

4-fluoro-4-phenylthio-1,3-dioxolan-2-one

4-fluoro-4-phenylthio-1,3-dioxolan-2-one

Conditions
ConditionsYield
With tetraethylammonium fluoride In 1,2-dimethoxyethane at 20℃; Electrolysis; Pt electrodes;A 28 % Spectr.
B 44%
With tetraethylammonium fluoride In dichloromethane at 20℃; Product distribution; Further Variations:; Reagents; Solvents; Fluorination; Electrolysis;A 29 % Spectr.
B 16 % Spectr.
With triethylamine pentahydrogen fluoride salt In dichloromethane at 20℃; Electrolysis; Pt electrodes;A 67 % Spectr.
B n/a
4-(p-tolylthio)-1,3-dioxolan-2-one
398490-67-0

4-(p-tolylthio)-1,3-dioxolan-2-one

4-fluoro-1,3-dioxolane-2-one
114435-02-8

4-fluoro-1,3-dioxolane-2-one

Conditions
ConditionsYield
With triethylamine pentahydrogen fluoride salt In dichloromethane at 20℃; Electrolysis; Pt electrodes;40 % Spectr.
4-(p-tolylthio)-1,3-dioxolan-2-one
398490-67-0

4-(p-tolylthio)-1,3-dioxolan-2-one

A

4-fluoro-1,3-dioxolane-2-one
114435-02-8

4-fluoro-1,3-dioxolane-2-one

B

4-fluoro-4-(p-tolylthio)-1,3-dioxolan-2-one

4-fluoro-4-(p-tolylthio)-1,3-dioxolan-2-one

C

4-(p-fluoromethylphenylthio)-1,3-dioxolan-2-one

4-(p-fluoromethylphenylthio)-1,3-dioxolan-2-one

D

4-fluoro-4-(toluene-4-sulfinyl)-[1,3]dioxolan-2-one

4-fluoro-4-(toluene-4-sulfinyl)-[1,3]dioxolan-2-one

Conditions
ConditionsYield
With tetraethylammonium fluoride In 1,2-dimethoxyethane at 20℃; Electrolysis; Pt electrodes;A 23 % Spectr.
B 4 % Spectr.
C 5 % Spectr.
D 14 % Spectr.
4-(p-methoxyphenylthio)-1,3-dioxolan-2-one
398490-69-2

4-(p-methoxyphenylthio)-1,3-dioxolan-2-one

4-fluoro-1,3-dioxolane-2-one
114435-02-8

4-fluoro-1,3-dioxolane-2-one

Conditions
ConditionsYield
With triethylamine pentahydrogen fluoride salt In dichloromethane at 20℃; Electrolysis; Pt electrodes;62 % Spectr.
4-(p-methoxyphenylthio)-1,3-dioxolan-2-one
398490-69-2

4-(p-methoxyphenylthio)-1,3-dioxolan-2-one

A

4-fluoro-1,3-dioxolane-2-one
114435-02-8

4-fluoro-1,3-dioxolane-2-one

B

4-fluoro-4-(4-methoxy-phenylsulfanyl)-[1,3]dioxolan-2-one

4-fluoro-4-(4-methoxy-phenylsulfanyl)-[1,3]dioxolan-2-one

C

4-fluoro-4-(4-methoxy-benzenesulfinyl)-[1,3]dioxolan-2-one

4-fluoro-4-(4-methoxy-benzenesulfinyl)-[1,3]dioxolan-2-one

Conditions
ConditionsYield
With tetraethylammonium fluoride In 1,2-dimethoxyethane at 20℃; Electrolysis; Pt electrodes;A 41 % Spectr.
B n/a
C 12 % Spectr.
4-(p-bromophenylthio)-1,3-dioxolan-2-one
398490-68-1

4-(p-bromophenylthio)-1,3-dioxolan-2-one

4-fluoro-1,3-dioxolane-2-one
114435-02-8

4-fluoro-1,3-dioxolane-2-one

Conditions
ConditionsYield
With triethylamine pentahydrogen fluoride salt In dichloromethane at 20℃; Electrolysis; Pt electrodes;54 % Spectr.
4-phenylthio-1,3-dioxolane-2-one

4-phenylthio-1,3-dioxolane-2-one

4-fluoro-1,3-dioxolane-2-one
114435-02-8

4-fluoro-1,3-dioxolane-2-one

Conditions
ConditionsYield
With triethylamine pentahydrogen fluoride salt; tetraethylammonium chloride at 20℃; Electrochemical reaction;89 %Spectr.
With triethylamine pentahydrogen fluoride salt; tetraethylammonium bromide In dichloromethane at 20℃; Electrochemical reaction;78 %Spectr.
[1,3]-dioxolan-2-one
96-49-1

[1,3]-dioxolan-2-one

trans-4,5-difluoro-1,3-dioxolane-2-one

trans-4,5-difluoro-1,3-dioxolane-2-one

B

4-fluoro-1,3-dioxolane-2-one
114435-02-8

4-fluoro-1,3-dioxolane-2-one

Conditions
ConditionsYield
With fluorine at 50℃; Product distribution / selectivity; Inert atmosphere;
[1,3]-dioxolan-2-one
96-49-1

[1,3]-dioxolan-2-one

cis-4,5-difluoroethylene carbonate

cis-4,5-difluoroethylene carbonate

trans-4,5-difluoro-1,3-dioxolane-2-one

trans-4,5-difluoro-1,3-dioxolane-2-one

C

trifluoroethylene carbonate
857463-44-6

trifluoroethylene carbonate

D

4-fluoro-1,3-dioxolane-2-one
114435-02-8

4-fluoro-1,3-dioxolane-2-one

E

4,4-difluoro-1,3-dioxolan-2-one

4,4-difluoro-1,3-dioxolan-2-one

Conditions
ConditionsYield
With fluorine at 20.8 - 25.8℃; under 1875.19 Torr; Inert atmosphere;
4-fluoro-1,3-dioxolane-2-one
114435-02-8

4-fluoro-1,3-dioxolane-2-one

A

4,4-difluoro-1,3-dioxolan-2-one

4,4-difluoro-1,3-dioxolan-2-one

B

cis-4,5-difluoro-1,3-dioxolan-2-one

cis-4,5-difluoro-1,3-dioxolan-2-one

trans-4,5-difluoro-1,3-dioxolan-2-one

trans-4,5-difluoro-1,3-dioxolan-2-one

Conditions
ConditionsYield
With fluorineA 5%
B 11%
C 59%
4-fluoro-1,3-dioxolane-2-one
114435-02-8

4-fluoro-1,3-dioxolane-2-one

4-fluoro-5-chloroethylene carbonate

4-fluoro-5-chloroethylene carbonate

Conditions
ConditionsYield
With N-chloro-succinimide In tetrahydrofuran at 35℃; for 8h; Reagent/catalyst; Solvent; Temperature;

114435-02-8Relevant articles and documents

Recyclable polymer-supported iodobenzene-mediated electrocatalytic fluorination in ionic liquid

Sawamura, Takahiro,Kuribayashi, Shunsuke,Inagi, Shinsuke,Fuchigami, Toshio

, p. 2757 - 2760 (2010)

The electrochemical fluorination of organosulfur compounds in triethylamine/hydrofluoric acid (Et3N-5HF) with polystyrene-supported iodobenzene (PSIB) and tetraethylammonium chloride (Et4NCl) was performed successfully in an undivided cell under constant current conditions to afford the corresponding fluorinated compounds in moderate to good yields. Recycle use of the PSIB could be achieved due to its easy separation. Notably, the mediatory activity of the iodobenzene derivative was not appreciably changed even after 10 recycle uses.

Electroorganic synthesis under solvent-free conditions. Highly regioselective anodic monofluorination of cyclic ethers, lactones, and a cyclic carbonate

Hasegawa, Masaru,Ishii, Hideki,Fuchigami, Toshio

, p. 1503 - 1505 (2002)

Regioselective anodic fluorination of cyclic ethers, lactones, and a cyclic carbonate in Et4NF·nHF (n = 4, 5) and Et3N·5HF without a solvent was successfully carried out to give the corresponding monofluorinated products in moderate yields. This is the first report of direct electrochemical fluorination of cyclic ethers, lactones, and a cyclic carbonate using anodic fluorination.

Highly Robust {Ln4}-Organic Frameworks (Ln = Ho, Yb) for Excellent Catalytic Performance on Cycloaddition Reaction of Epoxides with CO2 and Knoevenagel Condensation

Chen, Hongtai,Li, Qiaoling,Liu, Shurong,Lv, Hongxiao,Zhang, Tao,Zhang, Xiutang

, p. 14916 - 14925 (2021/12/09)

Due to the high electron charge, large ion radius, and plentiful outer hybrid orbitals of LnIII cations, microporous Ln-MOFs can be used as Lewis acidic catalysts with high catalytic activity for a variety of organic reactions, which prompts us to explore cluster-based nanoporous Ln-MOFs by employing structure-oriented ligands. Herein, the exquisite combination of coplanar [Ln4(μ3–OH)2(μ2–HCO2)(H2O)2] clusters (abbreviated as {Ln4}) and the structure-oriented multifunctional ligand of 2,6-bis(2,4- dicarboxylphenyl)-4-(4-carboxylphenyl)pyridine (H5BDCP) led to two isomorphic nanoporous frameworks of {(Me2NH2)[Yb4(BDCP)2(μ3–OH)2(μ2–HCO2)(H2O)2]·5DMF·H2O}n (NUC-38Yb) and {(Me2NH2)[Ho4(BDCP)2(μ3–OH)2(μ2– HCO2)(H2O)2]·6DMF·3H2O}n (NUC-38Ho). To the best of our knowledge, NUC-38Ho and NUC-38Yb are rarely reported {Ln4}-based three-dimensional (3D) frameworks with embedded hierarchical triangular-microporous and hexagonal-nanoporous channels, which are shaped by six rows of coplanar {Ln4} clusters and characterized by plentiful coexisting Lewis acid–base sites on the inner wall including open LnIII sites, Npyridine atoms, μ3–OH, and μ2–HCO2. Catalytic experiments performed using NUC-38Yb as the representative exhibited that NUC-38Yb possessed a high catalytic activity on the cycloaddition reactions of epoxides with CO2 under mild conditions, which can be ascribed to its structural advantages including nanoscale channels, rich bifunctional active sites, large surface areas, and chemical stability. Moreover, NUC-38Yb, as a heterogeneous catalyst, could greatly accelerate the Knoevenagel condensation reactions of aldehydes and malononitrile. Hence, this work paves the way for the construction of functional Ln-cluster-based nanoporous metal–organic frameworks (MOFs) by elaborately designing functional ligands with transnormal connection modes.

Process for fluorinating inorganic or organic compounds by direct fluorination

-

Paragraph 00273-00274; 0283-0286, (2020/07/14)

The invention relates to the use of a fluorinated gas, wherein the elemental fluorine (F2) is present at a high concentration, the present invention relates to a process for producing fluorinated compounds by direct fluorination using a fluorination gas in which elemental fluorine (F2) is present at a high concentration, such as a concentration of elemental fluorine (F2), in particular equal to much higher than 15 vol% or even 20 vol% (i.e., at least 15 vol% or even 20 vol%), and to a process for producing fluorinated compounds by direct fluorination using a fluorination gas. The process of the present invention relates to the manufacture of fluorinated compounds other than fluorinated benzene by direct fluorination, in particular to the preparation of fluorinated organic compounds, end products and intermediates for use in agricultural, pharmaceutical, electronic, catalyst, solvent and other functional chemical applications. The fluorination process of the invention can be carried outin batches or in a continuous manner. If the process of the invention is carried out in batches, a column (tower) reactor may be used. If the process of the invention is continuous, a microreactor may be used.

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