CAS 1546-79-8 1-(Trifluoroacetyl)imidazole (HCID 73767)

Names & identifiers

Preferred name: 1-(Trifluoroacetyl)imidazole
IUPAC: 2,2,2-trifluoro-1-imidazol-1-ylethanone
English name: 1-(Trifluoroacetyl)imidazole
Molecular formula: C5H3F3N2O
Molecular weight: 164.09

Names & synonyms

1-(Trifluoroacetyl)imidazole1546-79-8N-Trifluoroacetylimidazole2,2,2-Trifluoro-1-(1H-imidazol-1-yl)ethanone1H-Imidazole, 1-(trifluoroacetyl)-1-(Trifluoroacetyl)-1H-imidazolen-(trifluoroacetyl)imidazoleMFCD000145012,2,2-trifluoro-1-(1H-imidazol-1-yl)ethan-1-one2,2,2-trifluoro-1-imidazol-1-ylethanone2,2,2-trifluoro-1-imidazol-1-yl-ethanoneN-TRIFLUOROACETYL IMIDAZOLE

Show more names

TRIFLUOROACETYLIMIDAZOLETFAITFBITrifluorobutyrliMidazoleTrifluorobutyryliMidazole1-(Trifluoroacetyl)imidazole 98%N-Trifluoroacetylimidazole, 98+%

8C6041OW3INSC-1519652,2,2-trifluoro-1-imidazolylethan-1-oneUNII-8C6041OW3IEINECS 216-282-5NSC151965NSC 1519651-trifluoroacetylimidazole

Database identifiers

CAS: 1546-79-8
PubChem CID: 73767
DTXSID: DTXSID60165669
UNII: 8C6041OW3I
EC Number: 216-282-5
Nikkaji: J206.770F

Properties

Computed structural properties

XLogP: 0.8
Topological polar surface area: 34.9 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 5
Rotatable bonds: 0
Heavy atoms: 11
Formal charge: 0
Complexity: 168

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Imidazoles

Physical DescriptionColorless to light yellow liquid.

Physicochemical properties

Boiling point: 137 °C · 137 °C(lit.)
Density: 1.442 g/mL · 1.442 g/mL at 25 °C(lit.)
refractive index: 20 · n20/D 1.424(lit.)
Flash point: 113 °F · 113 °F
storage temp.: 2 · 2-8°C
solubility: sol most common solvents, e.g. ether, THF.
pka: 0.78 · 0.78±0.10(Predicted)
form: clear liquid
color: Colorless to Yellow to Orange
Specific Gravity: 1.442 · 1.442
Water Solubility: reacts
Sensitive: Moisture Sensitive
BRN: 608904 · 608904
InChI: 1S/C5H3F3N2O/c6-5(7,8)4(11)10-2-1-9-3-10/h1-3H
InChIKey: SINBGNJPYWNUQI-UHFFFAOYSA-N
SMILES: FC(F)(F)C(=O)n1ccnc1
CAS DataBase Reference: 1546 · 1546-79-8(CAS DataBase Reference)
FDA UNII: 8 C6041OW3I · 8C6041OW3I
NIST Chemistry Reference: N-Trifluoroacetylimidazole(1546-79-8)
UNSPSC Code: 12352005 · 12352005
NACRES: 22 · NA.22
Symbol(GHS): 2 · GHS02,GHS07
Signal word: Warning
Hazard statements: 226 · H226-H315-H319-H335
Precautionary statements: 210 · P210-P302+P352-P305+P351+P338
target organs: Respiratory system
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes: Xi,F,C
Risk Statements: 10 · 10-36/37/38-34-22
Safety Statements: 26 · 26-36/37-45-36/37/39-16
RIDADR: 1993 · UN 1993 3/PG 3
WGK Germany: 3 · 3
F: 10 · 10-21
Hazard Note: Flammable/Moisture Sensitive/Keep Cold
TSCA: T
HazardClass: 3 · 3
PackingGroup: III
HS Code: 29332900 · 29332900
Storage Class: 3 · 3 - Flammable liquids
Hazard Classifications: 2 Flam · Eye Irrit. 2Flam. Liq. 3Skin Irrit. 2STOT SE 3
Limited Quantities: 5 L · 5.0 L (1.3 gallons) (liquid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P271, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 47 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information1-(Trifluoroacetyl)-1H-imidazole: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryMay cause irritation; [Aldrich MSDS]

Hazard Classes and CategoriesFlam. Liq. 3 (100%)

Safety data

F: 10-21
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 3
tsca: T
ridadr: UN 1993 3/PG 3
hs_code: 29332900
risk_code: 10-36/37/38-34-22
Signal word: Warning
Symbol(GHS): GHS02,GHS07
hazard_code: Xi,F,C
hazard_note: Flammable/Moisture Sensitive/Keep Cold
safety_code: 26-36/37-45-36/37/39-16
hazard_class: 3
Storage Class: 3 - Flammable liquids
packing_group: III
target organs: Respiratory system
Hazard statements: H226-H315-H319-H335
Limited Quantities: 5.0 L (1.3 gallons) (liquid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
Hazard Classifications: Eye Irrit. 2Flam. Liq. 3Skin Irrit. 2STOT SE 3
Precautionary statements: P210-P302+P352-P305+P351+P338

Chemistry & industry

Applications

Uses1-(Trifluoroacetyl)imidazole was used as a derivating agent to sequentially derivatize functional groups like amino groups, in a study demonstrating trimethylsilyl esters of aromatic and aliphatic sulfonic acids.

General Description1-(Trifluoroacetyl)imidazole is a derivatizing reagent.

Preparation methods · 1 item

PreparationN,N′-Carbonyldiimidazole (20.5 g) is dissolved in 100 ml of dry THF and treated dropwise with 28.8 g of Trifluoroacetic Acid in 80 mL of dry THF. The resulting solution is cooled for several hours. Removal of the solvent and distillation of the filtrate gives 14.4 g of material. Alternatively, Imidazole (25.8 g) in 120 mL of dried THF is treated dropwise, with cooling, with 39.9 g of Trifluoroacetic Anhydride in 50 mL of dried THF. Filtration, removal of solvent, and distillation gives 24.8 g of 1-(Trifluoroacetyl)imidazole.