5-Fluoroisatoic anhydride

HCID 288560

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Basic information

CAS: 321-69-7
Standard SMILES: O=c1[nH]c2ccc(F)cc2c(=O)o1
InChIKey: UBKGOWGNYKVYEF-UHFFFAOYSA-N
Molecular formula: C8H4FNO3
Average molar mass: 181.12 g/mol
Monoisotopic mass: 181.01752121

Names & identifiers

Preferred name: 5-Fluoroisatoic anhydride
IUPAC: 6-fluoro-1H-3,1-benzoxazine-2,4-dione
English name: 5-Fluoroisatonic anhydride
Molecular formula: C8H4FNO3
Molecular weight: 181.12

Names & synonyms

5-Fluoroisatoic anhydride6-FLUORO-2,4-DIHYDRO-1H-3,1-BENZOXAZINE-2,4-DIONEDTXSID30302241RefChem:535984DTXCID80253375640-488-8687-908-6321-69-76-fluoro-1H-benzo[d][1,3]oxazine-2,4-dione5-Fluoroisatonic anhydride6-fluoro-1H-3,1-benzoxazine-2,4-dione6-fluoro-2H-3,1-benzoxazine-2,4(1H)-dione

Show more names

NSC 1498156-FLUORO ISATIN ANHYDRIDE6-Fluorobenzo[d][1,3]oxazine-2,4-dione6-fluoro-1H-3,1-benzoxazine-2,4-quinone

MFCD033007196-fluoro-2H-benzo[d][1,3]oxazine-2,4(1H)-dioneFlumazenil Impurity 155-FLUOROISATOICANHYDRIDE2H-3,1-Benzoxazine-2,4(1H)-dione, 6-fluoro-6-Fluoro-1H-benzo[d][1,3]oxazine-2,4-dione; 6-Fluoro-2H-3,1-benzoxazine-2,4(1H)-dione; 6-Fluorobenzo[d][1,3]oxazine-2,4-dione; NSC 149815;NSC149815SCHEMBL694149

Database identifiers

CAS: 321-69-7
PubChem CID: 288560
DTXSID: DTXSID30302241
EC Number: 640-488-8
Nikkaji: J1.217.702J

Properties

Computed structural properties

XLogP: 1.1
Topological polar surface area: 55.4 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 4
Rotatable bonds: 0
Heavy atoms: 13
Formal charge: 0
Complexity: 256

Physicochemical properties

Melting point: 259 · 259-262°C
Density: 1.502 · 1.502±0.06 g/cm3(Predicted)
storage temp.: Inert atmosphere,Room Temperature
solubility: soluble in DMSO
pka: 9.61 · 9.61±0.20(Predicted)
form: powder
color: Off-white to pale yellow
InChI: InChI=1S/C8H4FNO3/c9-4-1-2-6-5(3-4)7(11)13-8(12)10-6/h1-3H,(H,10,12)
InChIKey: UBKGOWGNYKVYEF-UHFFFAOYSA-N
SMILES: N1C2=CC=C(F)C=C2C(=O)OC1=O
CAS DataBase Reference: 321 · 321-69-7(CAS DataBase Reference)
UNSPSC Code: 12352200 · 12352200
NACRES: 21 · NA.21
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319
Precautionary statements: 264 · P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-36
WGK Germany: 3 · WGK 3
HazardClass: IRRITANT
HS Code: 2934999090 · 2934999090
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 4 OralEye · Acute Tox. 4 OralEye Irrit. 2

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (66.7%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, 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 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (66.7%)

Safety data

wgk: WGK 3
hs_code: 2934999090
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
safety_code: 26-36
hazard_class: IRRITANT
Storage Class: 11 - Combustible Solids
Hazard statements: H315-H319
Hazard Classifications: Acute Tox. 4 OralEye Irrit. 2
Precautionary statements: P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Chemistry & industry

Applications

Uses5-Fluoroisatoic Anhydride is a versatile pharmaceutical intermediate used in the preparation of insulin secretagogues, HCV polymerase inhibitors, anxiolytic agents and other bioactive compounds.

Preparation methods · 1 item

Preparation5-Fluoroisatonic anhydride is prepared from 5-fluoro indole (9d) by stirring in a 4:1 mixture of DMF/H2O for 16 h at room temperature. 1 H NMR (DMSO-d6): δ11.19 (s, br., 1H), 7.36 (dd, J = 8.4, 2.6 Hz, 1H), 6.87 (dt, J = 8.4, 2.2 Hz, 1H), 6.74 (dd, J = 9.3, 2.2 Hz, 1H).