ethyl 2-bromo-2,2-difluoroacetate

• ChemBase ID: 8720
• Molecular Formular: C4H5BrF2O2
• Molecular Mass: 202.9821064
• Monoisotopic Mass: 201.94409784
• SMILES: C(F)(F)(Br)C(=O)OCC
• Canonical SMILES: CCOC(=O)C(Br)(F)F
• InChI: InChI=1S/C4H5BrF2O2/c1-2-9-3(8)4(5,6)7/h2H2,1H3
• InChIKey: IRSJDVYTJUCXRV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 2-bromo-2,2-difluoroacetate
• IUPAC Traditional name: ethyl 2-bromo-2,2-difluoroacetate
• Synonyms: Ethyl bromodifluoroacetate; ethyl 2-bromo-2,2-difluoroacetate; Bromodifluoroacetic acid ethyl ester; 2-Bromo-2,2-difluoro-1-ethoxyethan-1-one; 2-Bromo-2,2-difluoro-1-ethoxy-1-oxoethane; Bromo(difluoro)acetic acid ethyl ester; Ethyl bromo(difluoro)acetate 98%; Ethyl bromodifluoroacetate; 二氟溴乙酸乙酯

Database IDs

• CAS Number: 667-27-6
• EC Number: 211-567-0
• MDL Number: MFCD00042069
• Beilstein Number: 1906095
• PubChem SID: 24857811; 24850259; 160972027
• PubChem CID: 69585

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.7687443
• LogD (pH = 7.4): 1.7687443
• Log P: 1.7687443
• Molar Refractivity: 30.8149 cm^3
• Polarizability: 11.921133 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 112 °C/700 mmHg(lit.); 112°C/700mm; 112-114°C
• Flash Point: 21 °C; 21°C; 21°C(69°F); 69.8 °F
• Density: 1.583; 1.583 g/mL at 25 °C(lit.)
• Refractive Index: 1.3870; 1.3880; 1.39; n20/D 1.387; n20/D 1.387(lit.)

Safety Information

• Storage Warning: Corrosive/Highly Flammable/Light Sensitive; IRRITANT, FLAMMABLE
• European Hazard Symbols: Corrosive (C)
• UN Number: 2924; UN2924
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2; II
• Risk Statements: 10-34
• Safety Statements: 20-23-26-36/37/39-45; 26-36/37/39-45
• TSCA Listed: false; 否
• GHS Pictograms: GHS02; GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H314; H225-H314-H318
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; P210-P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2924 3/PG 2

Product Information

• Purity: ≥96.0% (GC); 97%; 98%; 98+%
• Grade: purum
• Linear Formula: BrCF2COOCH2CH3

DETAILS

Apollo Scientific Ltd - PC3162

Treatment of the Reformatsky reagent with aldehydes and ketones affords 2,2-difluoro-3-hydroxy esters. Please enquire for references and other data for this item.

Sigma Aldrich - 295795

Packaging
5 g in glass bottle

Sigma Aldrich - 16900

Other Notes
Synthesis of α,α-difluoro-β-hydroxy esters via a Reformatsky reaction1,2

REFERENCES

• Valuable building block for the introduction of the CF₂ group by Reformatsky reaction with aldehydes. A further development of this chemistry involves the generation of an ɑɑ-difluoro-?-lactone, followed by thermal decarboxylation as a high-yield route to 1,1-difluoroalkenes: J. Org. Chem., 60, 5378 (1995):