Basic information
- CAS
667-27-6- Standard SMILES
CCOC(=O)C(F)(F)Br- InChIKey
IRSJDVYTJUCXRV-UHFFFAOYSA-N- Molecular formula
- C4H5BrF2O2
- Average molar mass
- 202.98 g/mol
- Monoisotopic mass
- 201.94409794
Names & identifiers
- Preferred name
- Ethyl bromodifluoroacetate
- IUPAC
- ethyl 2-bromo-2,2-difluoroacetate
- English name
- Ethyl bromodifluoroacetate
- Molecular formula
- C4H5BrF2O2
- Molecular weight
- 202.98
Names & synonyms
Show more names
Database identifiers
- CAS
667-27-6- PubChem CID
- 69585
- DTXSID
DTXSID40216845- UNII
- 2QFZ6JJ5YH
- EC Number
- 211-567-0
- Nikkaji
- J205.964I
Properties
Computed structural properties
- XLogP
- 1.6
- Topological polar surface area
- 26.3 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 3
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 115
Physicochemical properties
- Boiling point
- 112 °C/700 · 112 °C/700 mmHg (lit.)
- Density
- 1.583 g/mL · 1.583 g/mL at 25 °C (lit.)
- refractive index
- 20 · n20/D 1.387(lit.)
- Flash point
- 70 °F · 70 °F
- storage temp.
- Keep in dark place,Inert atmosphere,Room temperature
- solubility
- Soluble in most organic solvents.
- form
- Liquid
- color
- Clear colorless to slightly yellow
- Specific Gravity
- 1.583 · 1.583
- BRN
- 1906095 · 1906095
- InChI
- InChI=1S/C4H5BrF2O2/c1-2-9-3(8)4(5,6)7/h2H2,1H3
- InChIKey
- IRSJDVYTJUCXRV-UHFFFAOYSA-N
- SMILES
- C(OCC)(=O)C(Br)(F)F
- CAS DataBase Reference
- 667 · 667-27-6(CAS DataBase Reference)
- FDA UNII
- 2 QFZ6JJ5YH · 2QFZ6JJ5YH
- NIST Chemistry Reference
- Ethyl bromodifluoroacetate(667-27-6)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 2 · GHS02,GHS05
- Signal word
- Danger
- Hazard statements
- 225 · H225-H314
- Precautionary statements
- 210 · P210-P233-P240-P280-P303+P361+P353-P305+P351+P338
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- Hazard Codes
- C,F,Xi
- Risk Statements
- 10 · 10-34-36
- Safety Statements
- 26 · 26-36/37/39-45-16-27
- RIDADR
- 2924 · UN 2924 3/PG 2
- WGK Germany
- 3 · 3
- Hazard Note
- Irritant/Flammable
- TSCA
- No
- HazardClass
- 3 · 3
- PackingGroup
- II
- HS Code
- 29159000 · 29159000
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 2 Skin · Flam. Liq. 2Skin Corr. 1B
- REACH Registrations
- Active
- Limited Quantities
- 1 L · 1.0 L (0.3 gallon) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
Safety & regulation
GHS classification
GHS Classification
Danger
H225 (96.3%): Highly Flammable liquid and vapor [Danger Flammable liquids]
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 (click each P-code to see the statement)
Aggregated GHS information provided per 54 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Status: Active Update: 28-05-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/31053
Acetic acid, bromodifluoro-, ethyl ester: Does not have an individual approval but may be used under an appropriate group standard
Safety data
- PPE
- Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- No
- ridadr
- UN 2924 3/PG 2
- hs_code
- 29159000
- risk_code
- 10-34-36
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS05
- hazard_code
- C,F,Xi
- hazard_note
- Irritant/Flammable
- safety_code
- 26-36/37/39-45-16-27
- hazard_class
- 3
- Storage Class
- 3 - Flammable liquids
- packing_group
- II
- Hazard statements
- H225-H314
- Limited Quantities
- 1.0 L (0.3 gallon) (liquid)
- Excepted Quantities
- Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
- REACH Registrations
- Active
- Hazard Classifications
- Flam. Liq. 2Skin Corr. 1B
- Precautionary statements
- P210-P233-P240-P280-P303+P361+P353-P305+P351+P338
Chemistry & industry
Applications
DescriptionEthyl bromodifluoroacetate, a clear to yellow liquid, is an ester of bromodifluoroacetic acid and ethyl alcohol. It is an ester that can be used to introduce the CF2 group when synthesizing chemical compounds. Ethyl bromdifluoroacetate is considered to be a good compound in the generation of compounds and for testing with other organic compounds like lactones, imines, and other amino acids.
UsesEthyl 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.
UsesEfficient 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. A Cu-catalyzed regioselective bromodifluoroacetylation of alkenes, using ethyl bromodifluoroacetate (BrCF2CO2Et) as a difluoroacetylating reagent.
UsesEthyl 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.
Preparation methods
PreparationDifluorobromoacetonitrile is taken as a raw material, and prepared through a one-pot method and subjected to alcoholysis and esterification in ethanol aqueous solution to obtain ethyl bromodifluoroacetate.Reaction equation is: BrF2CCN→BrF2CCOOH→BrF2CCOOC2H5
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers100 total
Related reactions
Compound notes
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