Luminol

Luminol Basic information
Chemical fluorescent molecules Chemiluminescence method Chemical properties Uses Hazards & Safety Information
Product Name:Luminol
Synonyms:3-AMINOPHTHALHYDRAZINE;3-AMINOPHTHALIC HYDRAZIDE;3-AMINOPHTHALOYLHYDRAZINE;3-AMINOPHTHALHYDRAZIDE;5-AMINO-2,3-DIHYDRO-PHTHALAZINE-1,4-DIONE;5-AMINO-2,3-DIHYDRO-1,4-PHTHALAZINEDONE;5-AMINO-1,2,3,4-TETRAHYDRO-1,4-PHTHALAZINEDIONE;AURORA KA-3798
CAS:521-31-3
MF:C8H7N3O2
MW:177.16
EINECS:208-309-4
Product Categories:Pharmaceutical intermediates;Analytical Chemistry;Chemiluminescence;Luminols (Chemiluminescence);Piperazine derivates;Fluorescent;521-31-3
Mol File:521-31-3.mol
Luminol Structure
Luminol Chemical Properties
Melting point >300 °C (lit.)
Boiling point 309.07°C (rough estimate)
density 1.3393 (rough estimate)
refractive index 1.6500 (estimate)
storage temp. Store below +30°C.
solubility Insoluble in water, soluble in dimethyl sulfoxide.
form Powder
pka(Calcd.) 10.50 ± 0.20;;0.58 ± 0.20(at 25℃)
color Dark green to dark blue-purple
PH RangeNonH uorescence (6.0) to blue H uorescence (7.0)
Water Solubility <0.1 g/100 mL at 19 ºC
λmax425nm
Merck 14,5600
BRN 383929
Stability:Stable. Combustible. Incompatible with strong oxidizing agents, strong acids, strong bases, strong reducing agents. Emits light on reaction with oxidizers.
Major ApplicationNight vision devices, identification of product forgeries, determination of nitride in food, analytical chemistry, pharmaceuticals, iodine in biological materials, evaluating phagocytes, detecting tumors, DNA, biosensors, assay of fungi, bacteria, yeasts, assay of lipase activity
InChIKeyHWYHZTIRURJOHG-UHFFFAOYSA-N
LogP-0.245 (est)
CAS DataBase Reference521-31-3(CAS DataBase Reference)
NIST Chemistry Reference3-Aminophthalhydrazide(521-31-3)
EPA Substance Registry SystemLuminol (521-31-3)
Safety Information
Hazard Codes Xi,Xn
Risk Statements 36/37/38-22-20/21/22
Safety Statements 26-36/37-37/39-36
WGK Germany 3
RTECS TH8890060
10-23
TSCA Yes
HS Code 29339990
MSDS Information
ProviderLanguage
3-Aminophthalhydrazide English
SigmaAldrich English
ACROS English
ALFA English
Luminol Usage And Synthesis
Chemical fluorescent moleculesLuminol is an organic compound which, when oxidized, emits light — a phenomenon known as chemiluminescence.  This is similar to the reactions that fireflies uses to emit light, and to those used in "glow-sticks" and some roadside emergency lights. In this reaction, a small amount of luminol (3-aminophthalhydrazide or 5-amino-2,3-dihydro- 1,4-phthalazinedione) is dissolved in a basic aqueous solution, which also contains a small amount of copper(II) sulfate.  To this solution is added a solution of a mild oxidizing agent, which is 0.3% hydrogen peroxide in the demonstration below.  (Bleach is also used in some recipes as the oxidizing agent.)  The reaction is believed to occur by the following mechanism:
Luminol Chemiluminescence method
Chemiluminescence methodLuminol chemiluminescence has been trialed for estimating the PMI from skeletal remains. Luminol methods are based on the reaction between luminol and hydrogen peroxide which is catalyzed by iron in hemoglobin found in fluids and tissues from bodies. This reaction results in a chemiluminescence light which can be measured by various means .
Chemical propertiesYellow crystalline powder, Easily soluble in lye, soluble in dilute acid but almost insoluble in water and hardly soluble in alcohol. When its neutral or weak acidic solution is exposed to ultraviolet light, it exhibits strongly bright blue fluorescence. Melting point: 329-332 &deg; C
Uses1.    It can be used as chemical analysis reagents, indicators.
2.    It can be used for chemiluminescence analysis such as measurement of metal cations, blood and glucocorticoids
Hazards & Safety InformationCategory Toxic substances
Toxic grading poisoning
Acute toxicity Oral – rat; LD50: > 500 mg/kg
Flammability and Hazardous properties it is combustible with combustion producing toxic nitrogen oxide fumes
Storage and transportation characteristics warehouse: ventilated, low temperature and dry
Fire extinguishing agent dry powder, foam, sand, carbon dioxide, mist water




Chemical Propertiesyellow crystals or beige powder
UsesDetection of copper, iron, peroxides, cyanides.
UsesLuminol is a chemiluminescent probe that has been used to detect myeloperoxidase-mediated oxidative events in granulocytes and for chemiluminescence analysis of metal cations and blood.
UsesLuminol is used in the detection of copper, iron, peroxides and cyanides. It exhibits chemiluminescence and utilized to measure opsonic and phagocytic function. It acts as a biological sensor and involved in the detection of polymorphonuclear leukocytes response in a patient with a myeloperoxidase deficiency. Further, it is used as a forensic test for blood.
General DescriptionYellow crystals or light beige powder.
Air & Water ReactionsInsoluble in water.
Reactivity ProfileOxidation of 3-Aminophthalhydrazide is accompanied by a striking emission of light. . .
Health HazardACUTE/CHRONIC HAZARDS: When heated to decomposition 3-Aminophthalhydrazide emits toxic fumes.
Fire HazardFlash point data for 3-Aminophthalhydrazide are not available, but 3-Aminophthalhydrazide is probably combustible.
SynthesisThe synthesis of Luminol is as follows: To a reaction tube, add 140 mg of 3-nitrophthalhydrazide and 1.0 mL of 3 M sodium hydroxide solution. Stir with a rod, and to the resulting deep brown-red solution add 0.6 g of sodium hydrosulfite dihydrate (Na2S2O4 · 2 H2O, MW 210.2). Wash down the sides of the tube with a small amount of water. Heat to a gentle boil and keep the tube hot for 5 minutes. During this time some product may begin to crystallize. Add 0.4 mL of acetic acid, cool the tube in cold water, and stir. Collect the light-yellow product Luminol by suction filtration.
synthesis of Luminol
storageRoom temperature
Purification MethodsDissolve luminol in KOH solution, treat with Norit (charcoal), filter and precipitate it with conc HCl. [Hardy et al. Talanta 24 297 1977.] Store it in the dark in an inert atmosphere, because its structure changes during its luminescence. It has been recrystallised from 0.1M KOH [Merenyi et al. J Am Chem Soc 108 77716 1986]. [Beilstein 25 II 389, 25 III/IV 4192.]
LUMINOLSODIUM 2-amino-N-(1,4-dioxo-1,2,3,4-tetrahydrophthalazin-5-yl)propanamide 5-(propan-2-ylamino)-1,2,3,4-tetrahydrophthalazine-1,4-dione 5-[(2-methylpropyl)amino]-1,2,3,4-tetrahydrophthalazine-1,4-dione 5-[(3-methylbutan-2-yl)amino]-1,2,3,4-tetrahydrophthalazine-1,4-dione 5-(cyclopentylamino)-1,2,3,4-tetrahydrophthalazine-1,4-dione N-(1,4-dioxo-1,2,3,4-tetrahydrophthalazin-5-yl)-2-(methylamino)acetamide 5-(thiolan-3-ylamino)-1,2,3,4-tetrahydrophthalazine-1,4-dione Luminol Hydrochloride 2-cyano-N-(1,4-dioxo-1,2,3,4-tetrahydrophthalazin-5-yl)acetamide 5-[(1-cyclopropylethyl)amino]-1,2,3,4-tetrahydrophthalazine-1,4-dione 3-Nitrophthalhydrazide LUMINOL-13C4 (1,4-dioxo-1,2,3,4-tetrahydrophthalazin-5-yl)urea 5-[(3-methylbutyl)amino]-1,2,3,4-tetrahydrophthalazine-1,4-dione 2-amino-N-(1,4-dioxo-1,2,3,4-tetrahydrophthalazin-5-yl)acetamide 3-amino-N-(1,4-dioxo-1,2,3,4-tetrahydrophthalazin-5-yl)propanamide 5-(pentan-3-ylamino)-1,2,3,4-tetrahydrophthalazine-1,4-dione

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