3,4-dihydro-1,2,3-benzotriazin-4-one

• ChemBase ID: 85671
• Molecular Formular: C7H5N3O
• Molecular Mass: 147.1341
• Monoisotopic Mass: 147.0432618
• SMILES: n1nc2ccccc2c(=O)[nH]1
• Canonical SMILES: O=c1[nH]nnc2c1cccc2
• InChI: InChI=1S/C7H5N3O/c11-7-5-3-1-2-4-6(5)8-10-9-7/h1-4H,(H,8,9,11)
• InChIKey: DMSSTTLDFWKBSX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,4-dihydro-1,2,3-benzotriazin-4-one
• IUPAC Traditional name: 3H-1,2,3-benzotriazin-4-one
• Synonyms: 4-Ketobenzo-1,2,3(3H)-triazine; 1,2,3-Benzotriazin-4(3H)one; 3H-Benzo[d][1,2,3]triazin-4-one; 3,4-dihydro-1,2,3-benzotriazin-4-one; benzo[d][1,2,3]triazin-4(3H)-one; 1,2,3-Benzotriazin-4(3H)-one; 3,4-Dihydro-1,2,3-benzotriazin-4-one; 1,2,3-Benzotriazin-4(3H)-one; 1,2,3-苯并三嗪-4-酮; 1,2,3-苯并三嗪-4(3H)-酮

Database IDs

• CAS Number: 90-16-4
• EC Number: 201-971-5
• MDL Number: MFCD00052387
• Beilstein Number: 124996
• PubChem SID: 162072787; 24860827
• PubChem CID: 7006

CALCULATED PROPERTIES

• Acid pKa: 10.089514
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.7889743
• LogD (pH = 7.4): 1.7881986
• Log P: 1.7889842
• Molar Refractivity: 43.1811 cm^3
• Polarizability: 14.135948 Å^3
• Polar Surface Area: 53.82 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 139 - 143°C; 216-218 °C(lit.); 216-224°C; 222-224°C
• Hydrophobicity(logP): 0.838

Safety Information

• Storage Warning: Harmful/Irritant/Teratogenic
• RTECS: DM0800000
• European Hazard Symbols: X; Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 20/22-62; 36/37/38
• Safety Statements: 26-37/39; 9-36/37
• TSCA Listed: 是
• GHS Pictograms: GHS06; GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H301-H332-H361; H302-H315-H319-H335
• GHS Precautionary statements: P261-P281-P301+P310-P321-P405-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 95%; 97%; 98%
• Empirical Formula (Hill Notation): C7H5N3O

DETAILS

Sigma Aldrich - 340545

Packaging
5 g in glass bottle

REFERENCES

• Thermolysis with loss of N₂ gives a reactive keteneimine intermediate which undergoes [4+2] cycloaddition reactions: Tetrahedron Lett., 3465 (1966). For similar reaction with scheme, see Isatoic anhydride, A14603.