6292-67-7

Basic information

• Product Name: Hexanedioic acid, monohydrazide (9CI)
• Synonyms: Hexanedioic acid, monohydrazide (9CI);Hexanedioic acid, Monohydrazide;Hexanedioic acid 1-hydrazide;Monohydrazideadipic acid;NSC 9926
• CAS NO: 6292-67-7
• Molecular Formula: C₆H₁₂N₂O₃
• Molecular Weight: 160.17
• Mol File: 6292-67-7.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 436℃
• Flash Point: 218℃
• Appearance: /
• Density: 1.215
• Vapor Pressure: 7.92E-09mmHg at 25°C
• Refractive Index: 1.496
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Hexanedioic acid, monohydrazide (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Hexanedioic acid, monohydrazide (9CI)(6292-67-7)
• EPA Substance Registry System: Hexanedioic acid, monohydrazide (9CI)(6292-67-7)

Safety Data

• Hazardous Substances Data: 6292-67-7(Hazardous Substances Data)

Usage

Uses

Monohydrazide Adipic Acid is a synthetic reagent and a plant growth retarding agent.

InChI:InChI=1/C6H12N2O3/c7-8-5(9)3-1-2-4-6(10)11/h1-4,7H2,(H,8,9)(H,10,11)

Synthetic route

sodium-salt of adipic acid monoethyl ester → adipic acid monohydrazide (6292-67-7)

Conditions	Yield
With hydrazine hydrate

adipinic acid monoethyl ester (626-86-8) → adipic acid monohydrazide (6292-67-7)

Conditions	Yield
With hydrazine hydrate In ethanol for 12h; Reflux;

adipic acid monohydrazide (6292-67-7) + 4-methoxy-benzaldehyde (123-11-5) → adipic acid mono-(4-methoxy-benzylidenehydrazide)

Conditions	Yield
With water

adipic acid monohydrazide (6292-67-7) + acetone (67-64-1) → adipic acid mono-isopropylidenehydrazide (120364-53-6)

adipic acid monohydrazide (6292-67-7) → C37H49N4O19P2(1-)*HNa

Conditions	Yield
Multi-step reaction with 2 steps 1.1: trifluoroacetic acid / methanol / 12 h / 20 °C / Darkness 2.1: 1-hydroxy-pyrrolidine-2,5-dione; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dimethyl sulfoxide / 12 h / 20 °C 2.2: 12 h / 20 °C / pH 8 - 9 View Scheme

doxorubicin (23214-92-8) + adipic acid monohydrazide (6292-67-7) → C33H39N3O13

Conditions	Yield
With trifluoroacetic acid In methanol at 20℃; for 12h; Darkness;

Upstream product

• 626-86-8 adipinic acid monoethyl ester 

Relevant articles and documents

Actively Targeted Delivery of Doxorubicin to Bone Metastases by a pH-Sensitive Conjugation

Alendronate-monoethyl adipate-(hydrazone)-doxorubicin conjugate (ALN-MA-hyd-DOX) was synthesized to specifically deliver doxorubicin (DOX) to bone tumor tissue. The binding kinetics of ALN-MA-hyd-DOX with hydroxyapatite (HA) and natural bone were detected by using spectrophotometer. Cytotoxicity of ALN-MA-hyd-DOX on tumor cells was determined by MTT [3-(4,5-dimethylthiaol-2-yl)-2,5-diphenyl-tetrazolium bromide] method. The cellular uptake of ALN-MA-hyd-DOX was observed by using fluorescence microscopy. The in vivo antitumor activity of ALN-MA-hyd-DOX was investigated by using tumor-bearing nude mice model. The results indicated that ALN-MA-hyd-DOX was able to quickly bind with HA and natural bone. ALN-MA-hyd-DOX immobilized on the natural bone released more DOX in pH 5.0 medium than that in pH 6.0 or 7.4 medium. The cytotoxicity of ALN-MA-hyd-DOX toward A549 cells and MDA-MB-231/ADR cells was greater than DOX. ALN-MA-hyd-DOX was rapidly uptaken by A549 cells and MDA-MB-231/ADR cells. Compared with the same dose of free DOX, ALN-MA-hyd-DOX significantly decreased tumor volume of tumor-bearing nude mice. DOX mainly distributed in bone tumor tissue after ALN-MA-hyd-DOX was intravenously administered to tumor-bearing nude mice, whereas DOX distributed through the whole body after DOX was intravenously administered to tumor-bearing nude mice. These findings implied that the ALN-MA-hyd-DOX was a promising bone-targeted conjugate for treating bone neoplasms.