Trifluoromethyluracil (HCID 5899)

Overview

a metabolite of trifluorothymidine in the mammalian brain tissue; structure in first source

Names & identifiers

Preferred name: Trifluoromethyluracil
IUPAC: 5-(trifluoromethyl)-1H-pyrimidine-2,4-dione
English name: Trifluorothymine
Molecular formula: C5H3F3N2O2
Molecular weight: 180.08

Names & synonyms

Trifluoromethyluracil5-TFMURefChem:8996125-(Trifluoromethyl)uracil54-20-65-Trifluoromethyluracil5-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione5-(trifluoromethyl)-1H-pyrimidine-2,4-dione2,4(1H,3H)-Pyrimidinedione, 5-(trifluoromethyl)-MFCD000060245-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dioneURACIL, 5-(TRIFLUOROMETHYL)-

Show more names

5-(trifluoroMethyl)pyriMidine-2,4-diol5-Trifluoromethyl2,4-DIHYDROXY-5-TRIFLUOROMETHYL-1H-PYRIMIDINETRIFLUOROTHYMINE5-TrifluorothymineTrifluorothymine 5-

5-Trifluoromethyl-1H-pyrimidine-2,4-dione5-trifluoromethyl-uracilL 595725-0-1NSC73757NSC-737574U846R5P34ifluoromethyl)pyrimidine-2,4(1H,3H)-dioneEINECS 200-197-5

Database identifiers

CAS: 54-20-6
PubChem CID: 5899
DTXSID: DTXSID40202304
ChEMBL: CHEMBL405942
UNII: 4U846R5P34
EC Number: 200-197-5
Nikkaji: J49.057A

Properties

Computed structural properties

XLogP: 0
Topological polar surface area: 58.2 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 5
Rotatable bonds: 0
Heavy atoms: 12
Formal charge: 0
Complexity: 268

Experimental & physicochemical properties

SpringerMaterials PropertiesChemical shift

Physicochemical properties

Melting point: 245 · 245-246 °C(lit.)
Density: 1.5484 · 1.5484 (estimate)
storage temp.: -20 °C · Sealed in dry,Store in freezer, under -20°C
solubility: 50 mg/mL, · methanol: soluble50mg/mL, clear
pka: 6.63 · 6.63±0.10(Predicted)
form: powder to crystal
color: White to Orange to Green
Water Solubility: INSOLUBLE
BRN: 612694 · 612694
InChI: InChI=1S/C5H3F3N2O2/c6-5(7,8)2-1-9-4(12)10-3(2)11/h1H,(H2,9,10,11,12)
InChIKey: LMNPKIOZMGYQIU-UHFFFAOYSA-N
SMILES: C1(=O)NC=C(C(F)(F)F)C(=O)N1
CAS DataBase Reference: 54 · 54-20-6(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 4 U846R5P34 · 4U846R5P34
NIST Chemistry Reference: 2 · 2,4(1H,3h)-pyrimidinedione, 5-(trifluoromethyl)-(54-20-6)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 6 · GHS06
Signal word: Danger
Hazard statements: 301 · H301-H315-H319-H335
Precautionary statements: 301 · P301+P310+P330-P302+P352-P305+P351+P338
target organs: Respiratory system
Hazard Codes: Xi,T
Risk Statements: 22 · 22-36/38-40-36/37/38-25
Safety Statements: 24 · 24/25-36-26
RIDADR: 2811 · 2811
WGK Germany: 3 · 3
RTECS: 1750000 · YR1750000
Hazard Note: Irritant
HazardClass: 6.1 · 6.1
PackingGroup: Ⅲ
HS Code: 29335990 · 29335990
Storage Class: 6.1 C · 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications: 3 OralEye · Acute Tox. 3 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Toxicity: 50 intraperitoneal · LD50 intraperitoneal in mouse: 800mg/kg

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H301 (91.1%): Toxic if swallowed [Danger Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 45 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 3 (91.1%)

Safety data

wgk: 3
rtecs: YR1750000
ridadr: 2811
hs_code: 29335990
Toxicity: LD50 intraperitoneal in mouse: 800mg/kg
risk_code: 22-36/38-40-36/37/38-25
Signal word: Danger
Symbol(GHS): GHS06
hazard_code: Xi,T
hazard_note: Irritant
safety_code: 24/25-36-26
hazard_class: 6.1
Storage Class: 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
packing_group: Ⅲ
target organs: Respiratory system
Hazard statements: H301-H315-H319-H335
Hazard Classifications: Acute Tox. 3 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P301+P310+P330-P302+P352-P305+P351+P338

Chemistry & industry

Applications

UsesTrifluorothymine is an antitumor and antiviral agent. Trifluorothymine was found in patientsтАЩ urine as a metabolite of Trifluorothymidine as cancer treatment.