28461-49-6

Basic information

• Product Name: 2-AMINO-5-METHYLBENZENE-1-CARBOHYDRAZIDE
• Synonyms: 2-AMINO-5-METHYLBENZENE-1-CARBOHYDRAZIDE;2-Amino-5-methylbenzohydrazide;2-Amino-5-methylbenzohydrazide, 2-(Hydrazinocarbonyl)-4-methylaniline;2-Amino-5-methylbenzoic acid hydrazide
• CAS NO: 28461-49-6
• Molecular Formula: C₈H₁₁N₃O
• Molecular Weight: 165.19
• Mol File: 28461-49-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: 133 °C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.219g/cm³
• Refractive Index: 1.623
• CAS DataBase Reference: 2-AMINO-5-METHYLBENZENE-1-CARBOHYDRAZIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-5-METHYLBENZENE-1-CARBOHYDRAZIDE(28461-49-6)
• EPA Substance Registry System: 2-AMINO-5-METHYLBENZENE-1-CARBOHYDRAZIDE(28461-49-6)

Safety Data

• Hazardous Substances Data: 28461-49-6(Hazardous Substances Data)

Usage

General Description

2-Amino-5-methylbenzene-1-carbohydrazide is a chemical compound with the molecular formula C8H11N3O. It is a member of the carbohydrazide family and is commonly used as a reagent in organic synthesis, particularly in the preparation of pharmaceuticals, dyes, and corrosion inhibitors. 2-AMINO-5-METHYLBENZENE-1-CARBOHYDRAZIDE is a white to off-white crystalline powder with a melting point of 207-210°C and is sparingly soluble in water. It acts as a chelating agent and can form coordination complexes with various metal ions. 2-Amino-5-methylbenzene-1-carbohydrazide is also known for its use in the preparation of pyrazole, which has applications in the pharmaceutical industry as a precursor to various drugs.

InChI:InChI=1/C8H11N3O/c1-5-2-3-7(9)6(4-5)8(12)11-10/h2-4H,9-10H2,1H3,(H,11,12)

Upstream product

• 4692-99-3 6-methyl-1H-benzo[d][1,3]oxazine-2,4-dione 
• 18595-16-9 2-amino-5-methylbenzoic acid methyl ester 
• 2941-78-8 2-Amino-5-methylbenzoic acid 

Downstream Products

• 96134-67-7 4-Methyl-2-(5-methyl-1,3,4-oxadiazol-2-yl)benzeneamine 
• 85516-74-1 dimethyl-2,7 dihydro-3,4 benzotriazepine-1,3,4 (5H) one-5 
• 85516-81-0 amino-3 dimethyl-2,6 (3H) quinazolinone-4 
• 93595-55-2 5-(2-Amino-5-methyl-phenyl)-3H-[1,3,4]oxadiazol-2-one 
• 96498-99-6 7-Methyl-2-phenyl-3,4-dihydro-5H-1,3,4-benzotriazepin-5-one 
• 96499-02-4 2-(2-Amino-5-methylphenyl)-5-phenyl-1,3,4-oxadiazole 
• 773143-40-1 5-(2-amino-5-methyl-phenyl)-3H-[1,3,4]oxadiazole-2-thione 
• 1403672-19-4 C₁₄H₁₃N₅ 
• 1403672-15-0 2-(9-methyl-2-pyridin-2-yl-5,6-dihydro[1,5-c]quinazolin-5-yl)phenol 
• 1427683-42-8 2-amino-N′-(imidazolidin-2-ylidene)-5-methylbenzohydrazide 

Relevant articles and documents

Discovery of phthalazino[1,2-b]-quinazolinone derivatives as multi-target HDAC inhibitors for the treatment of hepatocellular carcinoma via activating the p53 signal pathway

In view of histone deacetylases (HDACs) as a promising target for cancer therapy, a series of phthalazino[1,2-b]-quinazolinone units were hybrided with ortho-aminoanilide or hydroxamic acid to serve as multi-target HDAC inhibitors for the treatment of solid tumors. Among the target compounds, 8h possessed nano-molar IC50 values toward the tested cancer cells and HDAC subtypes, which was more potent than the HDAC inhibitor SAHA (vorinostat). Mechanism study revealed that compound 8h could suppress the HepG2 cell proliferation via prompting the acetylation of histone 3 (H3) and α-tubulin, and activating the p53 signal pathway as designed. In addition, compound 8h exhibited much stronger in vivo antitumor efficacy than SAHA in the HepG2 xenograft tumor model with negligible toxicity. As a novel multi-target HDAC inhibitor, compound 8h deserves further development as a potential anticancer agent.

A diversity oriented synthesis of 2,10-dioxo-10H-1,2,3,4,4a,5-hexahydropyridazino[3,2-b]quinazolines

A parallel method for the synthesis of the title compounds is described. Thus, methyl anthranilates (5) are transformed into 2-aminobenzohydrazides (3) which were treated with 4-oxo acids (4) to afford in high yields and acceptable purity of piridazino[3,2-b]quinazolines (1). Compounds (1) present four diversity centers (R1, R2, R3, and R4). The range of chemically acceptable substituents at each center has been evaluated. The isolation of a possible intermediate in the formation of 1, which presents an amino structure (10), has allowed proposing a complete mechanistic rationalization for the formation of structures (1).

The Chemistry of 2-Aminobenzoyl Hydrazides. 1. Effects of Orthoester Substituents on the Mode of Cyclization

Treatment of substituted 2-aminobenzoyl hydrazides with orthoesters has been found to yield different products depending upon the type of orthoester employed.Equimolar quantities of orthoester and hydrazide yield 3-amino-4(3H)-quinazolinones, whereas utilization of a two-fold excess (or greater) of orthoester yields, in some cases, 3,4-dihydro-5H-1,3,4-benzotriazepin-5-ones as minor products in addition to N-imidate esters as major products.Treatment of hydrazides with trimethyl orthobenzoate yields substituted 5-(2-aminophenyl)-1,3,4-oxadiazoles and 3,4-dihydro-5H-1,3,4-benzotriazepin-5-ones.The steric bulk of the phenyl group in trimethyl orthobenzoate effects the formation of adduct at the β-nitrogen of the hydrazide which cyclized to the oxadiazole and benzotriazepinone products.In the aliphatic orthoester series, the formation of adduct to the aromatic amino group appears to be favored which gives rise to quinazolinone and benzotriazepinone products.