Ethyl bromodifluoroacetate

Base Information

• Chemical Name: Ethyl bromodifluoroacetate
• CAS No.: 667-27-6
• Molecular Formula: C4H5BrF2O2
• Molecular Weight: 202.983
• Hs Code.: 29159000
• European Community (EC) Number: 211-567-0
• UNII: 2QFZ6JJ5YH
• DSSTox Substance ID: DTXSID40216845
• Nikkaji Number: J205.964I
• Wikipedia: Ethyl_bromodifluoroacetate
• Wikidata: Q72473181
• Mol file: 667-27-6.mol

Synonyms:Ethyl bromodifluoroacetate;667-27-6;ethyl 2-bromo-2,2-difluoroacetate;Ethylbromodifluoroacetate;Bromodifluoroacetic Acid Ethyl Ester;Acetic acid, bromodifluoro-, ethyl ester;ethyl difluorobromoacetate;2QFZ6JJ5YH;ethyl bromo(difluoro)acetate;EINECS 211-567-0;2-bromo-2,2-difluoroacetic acid ethyl ester;ethyl 2-bromo-2,2-difluoro-acetate;MFCD00042069;CBrF2COOCH2CH3;UNII-2QFZ6JJ5YH;ethyl 2-bromodifluoroacetate;ethyl bromo difluoro acetate;SCHEMBL162440;C4-H5-Br-F2-O2;Ethyl bromodifluoroacetate, 98%;IRSJDVYTJUCXRV-UHFFFAOYSA-;AMY3632;DTXSID40216845;ethyl 2,2-difluoro-2-bromoacetate;BCP11101;CS-D1417;bromodifluoro acetic acid ethyl ester;bromodifluoro-acetic acid ethyl ester;AKOS005258594;bromo-difluoro-acetic acid ethyl ester;ethyl bromo-alpha,alpha-difluoroacetate;FS-4453;BP-10583;2-bromo2,2-difluoroacetic acid ethyl ester;Aceticacid,2-bromo-2,2-difluoro-,ethylester;B1463;FT-0623240;EN300-39190;Acetic acid, 2-bromo-2,2-difluoro-, ethyl ester;Q-102548;F0001-2628

Chemical Property of Ethyl bromodifluoroacetate

Chemical Property:

• Appearance/Colour: clear colorless to slightly yellow liquid
• Vapor Pressure: 271.673mmHg at 25°C
• Refractive Index: n20/D 1.387(lit.)
• Boiling Point: 114.7 °C at 760 mmHg
• Flash Point: 23.2 °C
• PSA: 26.30000
• Density: 1.661 g/cm³
• LogP: 1.53720
• Storage Temp.: Flammables area
• Solubility.: Soluble in most organic solvents.
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 201.94410
• Heavy Atom Count: 9
• Complexity: 115

Purity/Quality:

99% ^*data from raw suppliers

Ethyl bromodifluoroacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F, Xi, C
• Hazard Codes: C,F,Xi
• Statements: 10-34-36
• Safety Statements: 26-36/37/39-45-16-27

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C(F)(F)Br
• Uses: Ethyl bromodifluoroacetate is usually used in the preparation of substituted ethyl 2′-pyridyldifluoroacetates,4-alkoxymethyl- and 4-aryloxymethyl-3,3-difluoropiperidines,α,α-difluoro-β-lactams,mono- and difluoromethylated phenanthridine derivatives. Efficient difluoroalkylation of aryl boronic acids via palladium catalysis. Novel, moisture-stable bromodifluoromethylated phosphonate, ester, and amide. Efficient coupling with aryl boronic acids via Pd catalysis. Ethyl bromodifluoroacetate, is used for the treatment of the Reformat sky reagent with aldehydes and ketones affords 2,2-difluoro-3-hydroxy esters. It is also used in the analysis of reagent purity through IR, NMR.

Technology Process of Ethyl bromodifluoroacetate

There total 16 articles about Ethyl bromodifluoroacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.5%

ethanol (64-17-5) + bromodifluoroacetyl chloride (3832-48-2) → Ethyl bromodifluoroacetate (667-27-6)

Guidance literature:

at 50 ℃; under 7500.75 Torr; Temperature; Pressure;

Reference yield: 90.76%

ethanol (64-17-5) + 1,2-dibromo-1-chloro-1,2,2-trifluoroethane (354-51-8) → Ethyl bromodifluoroacetate (667-27-6)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); oxygen; under 750.075 - 1500.15 Torr; Pressure; Reflux;

Reference yield: 88.0%

→ Ethyl bromodifluoroacetate (667-27-6)

Guidance literature:

upstream raw materials:

1,1-dibromo-2,2-difluoroethylene

ethanol

1,2-dibromo-1-chloro-1,2,2-trifluoroethane

<1,2,2-Trifluor-1,2-dibrom-aethyl>-aethylaether

Downstream raw materials:

bromodifluoroacetic acid

2-bromo-2,2-difluoroacetamide

ethyl α,α-difluoro-β-hydroxy-3-(2-pyridinyl)propanoate

ethyl α,α-difluoro-β-hydroxy-3-(4-pyridinyl)propanoate

Refernces

Synthesis of L-4,4-difluoroglutamic acid via nucleophilic addition to a chiral aldehyde

10.1021/jo015754q

The research focuses on the synthesis of L-4,4-difluoroglutamic acid, a fluorine-containing derivative of amino acids that is increasingly important for probing biological functions and enzyme mechanisms. The study presents a new, flexible route to enantiomerically pure L-4,4-difluoroglutamic acid, utilizing the addition of difluorinated nucleophiles to configurationally stable R-aminoaldehydes. The process involves several steps, including Barton-McCombie dehydroxylation and acid hydrolysis, to convert difluorinated adducts into the desired amino acid. Key chemicals used in this synthesis include 1,1-bis(dimethylamino)-2,2-difluoroethene, ethyl bromodifluoroacetate, Reformatsky reagent, and various protecting groups such as the 9-phenylfluoren-9-yl group.

Palladium-Catalyzed Cross-Coupling of Ethyl Bromodifluoroacetate with Aryl Bromides or Triflates and Cross-Coupling of Ethyl Bromofluoroacetate with Aryl Iodides

10.1021/acs.orglett.7b00938

Tingting Xia, Lei He, Yahu A. Liu, John F. Hartwig, and Xuebin Liao present a novel palladium-catalyzed Negishi cross-coupling reaction for constructing C(sp2)-CF2 and C(sp2)-CHF bonds using ethyl bromodifluoroacetate and ethyl bromofluoroacetate, respectively. The study describes a method to couple ethyl bromodifluoroacetate with aryl bromides and triflates under mild conditions without the need for organozinc reagent preparation, representing the first conversion of aryl triflates into products containing C-CF2 bonds. Additionally, the cross-coupling of aryl iodides with ethyl bromofluoroacetate was achieved under similar conditions to form a-aryl monofluoro esters in good yields. The optimized reaction conditions, using [Pd(p-cinnamyl)Cl]2 as the catalyst precursor and Xantphos as the ligand in THF solvent with TBAB as an additive, resulted in high yields for a broad range of aryl bromides and triflates. The study also demonstrated the versatility of the synthesized ethyl aryldifluoroacetates as precursors for further transformations into various compounds containing a CF2 unit.