5-amino-1,2,3,4-tetrahydrophthalazine-1,4-dione

• ChemBase ID: 75234
• Molecular Formular: C8H7N3O2
• Molecular Mass: 177.16008
• Monoisotopic Mass: 177.05382648
• SMILES: [nH]1c(=O)c2cccc(c2c(=O)[nH]1)N
• Canonical SMILES: Nc1cccc2c1c(=O)[nH][nH]c2=O
• InChI: InChI=1S/C8H7N3O2/c9-5-3-1-2-4-6(5)8(13)11-10-7(4)12/h1-3H,9H2,(H,10,12)(H,11,13)
• InChIKey: HWYHZTIRURJOHG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-amino-1,2,3,4-tetrahydrophthalazine-1,4-dione
• IUPAC Traditional name: luminol; 5-amino-1,2,3,4-tetrahydrophthalazine-1,4-dione
• Synonyms: 3-Aminophthalhydrazide (Luminol); 3-Aminophthalhydrazide; 5-Amino-2,3-dihydrophthalazine-1,4-dione; o-Aminophthaloyl hydrazide; o-Aminophthalyl hydrazide; 3-Aminophthalhydrazide; 3-Aminophthalic hydrazide; Luminol; 5-Amino-2,3-dihydro-1,4-phthalazinedione; Luminol; 5-amino-1,2,3,4-tetrahydrophthalazine-1,4-dione; Luminol; 3-Aminophthalhydrazide; 3-氨基邻苯二甲酰肼; 5-氨基-2,3-二氢-1,4-二氮杂萘二酮; 鲁米诺; 3-氨基邻苯二甲酰肼

Database IDs

• CAS Number: 521-31-3
• EC Number: 208-309-4
• MDL Number: MFCD00006890
• Beilstein Number: 383929
• Merck Index: 145600
• PubChem SID: 162040152; 24847519; 24891343
• PubChem CID: 10638
• CHEMBL: 442329
• Chemspider ID: 10192
• Wikipedia Title: Luminol

CALCULATED PROPERTIES

• Acid pKa: 13.712731
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -0.063616656
• LogD (pH = 7.4): -0.063561484
• Log P: -0.06356059
• Molar Refractivity: 47.3152 cm^3
• Polarizability: 16.49056 Å^3
• Polar Surface Area: 84.22 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: >300 °C(lit.); 319°C; 325-330°C
• Hydrophobicity(logP): -0.469

Safety Information

• RTECS: TH8890060
• European Hazard Symbols: X; Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 22-36/37/38; 36/37/38
• Safety Statements: 26-36/37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• NFPA704:
  

  1

  2

  0
• GHS Hazard statements: H302-H315-H319-H335; H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P280H-P305+P351+P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥97% (HPLC); ≥98.0% (HPLC); 95%; 97%; 98%
• Grade: for chemiluminescence; SAJ special grade
• Application(s): Also used by biologists in cellular assays for the detection of copper, iron, and cyanides; Antiinflammatories; Used by forensic investigators to detect trace amounts of blood left at crime scenes
• Empirical Formula (Hill Notation): C8H7N3O2

DETAILS

Sigma Aldrich - A8511

Features and Benefits
Used for chemiluminescence analysis1,2 of, for example, metal cations,3 blood,4 and glucococorticoids.5
Packaging
5, 25 g in glass bottle

Sigma Aldrich - 123072

Features and Benefits
Used for chemiluminescence analysis1,2 of, for example, metal cations,3 blood,4 and glucococorticoids.5
Packaging
2.5, 5 g in glass bottle
25 g in poly bottle

Sigma Aldrich - 09253

Analysis Note
luminescence test: Emmax 440 nm (chemiluminescence; in 60 mM K2S2O8, 100 mM K2CO3, pH 11.5; after addition of H2O2)
Features and Benefits
Used for chemiluminescence analysis1,2 of, for example, metal cations,3 blood,4 and glucococorticoids.5

Sigma Aldrich - 18-1760

Features and Benefits
Used for chemiluminescence analysis1,2 of, for example, metal cations,3 blood,4 and glucococorticoids.5

REFERENCES

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 384D, (ir)
• Aldrich Library of NMR Spectra, 2nd edn., 1983, 2, 365A, (nmr)
• Huntress, E.H. et al., J.A.C.S., 1934, 56, 241
• Org. Synth., 1949, 29, 78
• White, E.H. et al., J.A.C.S., 1964, 86, 941
• White, E.H. et al., Acc. Chem. Res., 1970, 3, 54, (rev)
• Reagent for the generation of chemiluminescence.