4-Aminophthalhydrazide Chemical Properties

Melting point:

300 °C (lit.)

Density 

1.433±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Soluble in ammonium hydroxide, sodium carbonate or other base.

pka

10.78±0.20(Predicted)

form 

Solid

color 

White to Off-White

Sensitive 

Air Sensitive

BRN 

164804

InChI

InChI=1S/C8H7N3O2/c9-4-1-2-5-6(3-4)8(13)11-10-7(5)12/h1-3H,9H2,(H,10,12)(H,11,13)

InChIKey

HUDPLKWXRLNSPC-UHFFFAOYSA-N

SMILES

C1(=O)C2=C(C=CC(N)=C2)C(O)=NN1

CAS DataBase Reference

3682-14-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

10-23

HS Code 

29280000

MSDS

• Language:English Provider:SigmaAldrich

4-Aminophthalhydrazide Usage And Synthesis

Uses

4-Aminophthalhydrazide is a chemiluminescent compound.

Chemical Properties

Powder

Uses

4-Aminophthalhydrazide has been used in:

• chemiluminescence-based reactive oxygen species (ROS) assay in bone marrow (BM) neutrophils post-Yersinia pseudotuberculosis infection
• neutrophil ROS assays post-K. pneumonia exposure
• neutrophil ROS assays in response to formylated-methionine-leucine-proline

Biochem/physiol Actions

4-Aminophthalhydrazide or isoluminol is a chemiluminescent compound that comprises a phthalazine ring. It is more hydrophilic than luminol. Isoluminol is commercially used in a wide variety of in vitro immunoassays and is a chemiluminescence amplifier for studying reactive oxygen species. It is also useful as an electroluminescence (ECL) biosensor and as a probe for rapid microbial detection.

Synthesis

The general procedure for the synthesis of 4-amino phthalazine hydrazide using 6-nitro-2,3-dihydrophthalazine-1,4-dione as starting material was as follows: Intermediate B was transferred to a 5L high-pressure hydrogenation reactor and 3 g of 10% palladium/carbon catalyst was added. The reaction system was heated to 35 ℃ and hydrogen was introduced until the pressure reached 4 atm, and the reaction was maintained at a constant pressure for 4 h. After the reaction was completed, the reaction was carried out with nitrogen. Upon completion of the reaction, the hydrogen in the reactor was replaced with nitrogen. Subsequently, the pH of the reaction solution was adjusted to 3-4 with 35% by weight concentrated hydrochloric acid. heating was continued to 100°C and the nitrogen gas flow was stopped. The reaction mixture was filtered while hot and the filtrate precipitated a large amount of solid after cooling to room temperature. The solid precipitate was collected by filtration and the filtrate could be used for organic solvent recovery. The resulting filter cake was washed with 400 ml of deionized water and dried to give 214 g of 4-amino phthalic hydrazide (isluminolide).

References

[1] Patent: CN106810501, 2017, A. Location in patent: Paragraph 0050
[2] Journal of the Chemical Society, 1937, p. 26,31
[3] Recueil des Travaux Chimiques des Pays-Bas, 1935, vol. 54, p. 471
[4] Bulet.Soc.Chim.Romania, 1930, vol. 12, p. 140,163
[5] Patent: CN105348202, 2016, A. Location in patent: Paragraph 0045; 0054; 0055; 0056

4-Aminophthalhydrazide(3682-14-2)Related Product Information

• 4-Dimethylaminobenzoic acid
• Glycine
• 4-Dimethylaminopyridine
• Phthalhydrazide
• 4-Dimethylaminobenzaldehyde
• 2-Amino-5-chlorobenzophenone
• Hydrochlorothiazide
• AMINOACETONITRILE HYDROGEN SULFATE
• Betaine
• 3-Aminoacetophenone
• O-Phthalimide
• ALTRENOGEST
• Buprofezin
• 4-Aminophthalic acid
• Dihydromyrcenol
• 2-Dimethylaminoethanol
• (6-[N-(6-AMINOHEXYL)-N-ETHYL]AMINO-2,3-DIHYDRO-1,4-PHTHALAZINE-1,4-DIONE
• 2,3-DIHYDRO-6-ISOTHIOCYANATO-1,4-PHTHALAZINEDIONE