Description

Ethyl bromodifluoroacetate (CAS No. 667-27-6) is a highly versatile fluorinated organic compound with the molecular formula C₄H₅BrF₂O₂. This reagent is widely utilized in synthetic organic chemistry, particularly as a key building block for the introduction of difluoromethyl and bromodifluoromethyl groups. Its IUPAC name, ethyl 2-bromo-2,2-difluoroacetate, reflects its structural composition, featuring a reactive bromodifluoroacetate moiety esterified with an ethyl group. The compound is characterized by its clear to pale yellow liquid appearance and should be stored under inert conditions to maintain stability. With a molecular weight of 203.98 g/mol, it is commonly employed in nucleophilic substitutions, cross-coupling reactions, and as a precursor for pharmaceuticals, agrochemicals, and specialty materials. Ethyl bromodifluoroacetate is available in high purity grades (>97%) and is packaged in amber glass bottles to prevent degradation.

Properties

• CAS Number: 667-27-6
• Complexity: 115
• IUPAC Name: ethyl 2-bromo-2,2-difluoro-acetate
• InChI: InChI=1S/C4H5BrF2O2/c1-2-9-3(8)4(5,6)7/h2H2,1H3
• InChI Key: IRSJDVYTJUCXRV-UHFFFAOYSA-N
• Exact Mass: 201.94410
• Molecular Formula: C4H5BrF2O2
• Molecular Weight: 202.98
• SMILES: CCOC(=O)C(F)(F)Br
• Topological: 26.3
• Monoisotopic Mass: 201.94410
• Synonyms: Ethyl bromodifluoroacetate, 667-27-6, ethyl 2-bromo-2,2-difluoroacetate, 2QFZ6JJ5YH, EINECS 211-567-0, 2-bromo-2,2-difluoroacetic acid ethyl ester, IRSJDVYTJUCXRV-UHFFFAOYSA-, DTXSID40216845, Acetic acid, 2-bromo-2,2-difluoro-, ethyl ester, DTXCID70139336, 211-567-0, inchi=1/c4h5brf2o2/c1-2-9-3(8)4(5,6)7/h2h2,1h3, irsjdvytjucxrv-uhfffaoysa-n, Ethylbromodifluoroacetate, Bromodifluoroacetic Acid Ethyl Ester, ethyl difluorobromoacetate, Acetic acid, bromodifluoro-, ethyl ester, ethyl bromo(difluoro)acetate, MFCD00042069, 2-Bromo-2,2-difluoroacetic Acid Ethyl Ester; Bromodifluoroacetic Acid Ethyl Ester; Ethyl 2-Bromo-2,2-difluoroacetate; Ethyl Difluorobromoacetate, ethyl 2-bromo-2,2-difluoro-acetate, CBrF2COOCH2CH3, UNII-2QFZ6JJ5YH, ethyl 2-bromodifluoroacetate, ethyl bromo difluoro acetate, SCHEMBL162440, Ethyl bromodifluoroacetate, 98%, ethyl 2,2-difluoro-2-bromoacetate, BCP11101, CS-D1417, Ethyl-2-bromo-2,2-difluoroacetate, bromodifluoro acetic acid ethyl ester, bromodifluoro-acetic acid ethyl ester, SBB093033, AKOS005258594, bromo-difluoro-acetic acid ethyl ester, ethyl bromo-alpha,alpha-difluoroacetate, FE10544, FS-4453, BP-10583, 2-bromo2,2-difluoroacetic acid ethyl ester, DB-029758, Aceticacid,2-bromo-2,2-difluoro-,ethylester, B1463, NS00036061, EN300-39190, F0001-2628

Application

Ethyl bromodifluoroacetate is extensively used in organic synthesis as a difluoromethylation reagent, enabling the incorporation of fluorine atoms into target molecules for enhanced metabolic stability and lipophilicity. It serves as a critical intermediate in the preparation of fluorinated pharmaceuticals, including protease inhibitors and antiviral agents. Additionally, this compound is employed in agrochemical research for developing novel pesticides with improved efficacy. Its reactivity in Pd-catalyzed cross-coupling reactions makes it valuable for constructing complex fluorinated scaffolds in medicinal chemistry.

Safety and Hazards

GHS Hazard Statements

• H225 (96.3%): Highly Flammable liquid and vapor [Danger Flammable liquids]
• H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

Precautionary Statements

• P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P321, P363, P370+P378, P403+P235, P405, and P501

Hazard Classes and Categories

• Flam. Liq. 2 (96.3%)
• Skin Corr. 1B (100%)

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