A0638

Adipic acid dihydrazide

≥98% (titration)

• Synonym(s): Hexanedihydrazide
• Linear Formula: NH₂NHCO(CH₂)₄CONHNH₂
• CAS Number: 1071-93-8
• Molecular Weight: 174.20
• Beilstein: 973863
• EC Number: 213-999-5
• MDL number: MFCD00007614
• UNSPSC Code: 12352127
• PubChem Substance ID: 24890442
• NACRES: NA.25

Properties

• Quality Level: 300
• Assay: ≥98% (titration)
• form: powder
• reaction suitability: reagent type: cross-linking reagent
• mp: 180-182 °C (lit.)
• solubility: H₂O: 100 mg/mL
• storage temp.: −20°C
• SMILES string: NNC(=O)CCCCC(=O)NN
• InChI: 1S/C6H14N4O2/c7-9-5(11)3-1-2-4-6(12)10-8/h1-4,7-8H2,(H,9,11)(H,10,12)
• InChI key: IBVAQQYNSHJXBV-UHFFFAOYSA-N

Description

General description

Adipic acid dihydrazide is a homobifunctional cross-linking reagent that is specific for aldehydes. This results in relatively stable hydrazone linkages. Adipic acid dihydrazide is generally used in the linking of glycoproteins, like antibodies, in a site-specific fashion following periodate oxidation. Oxidation and coupling may be performed at pH 5.0 due to the low pKa of the hydrazide which avoids competition by primary amines.

Application

Adipic acid dihydrazide has been used:

• in the preparation of reactive premix to synthesize the porous biomaterial
• for the crosslinking of methacrylated chondroitin sulfate (MA-CS) coating using carbodiimide-based chemistry for the production and characterization of methacrylated chondroitin sulfate magnetic nanoparticles (MA-CS MNPs)
• for the covalent labeling of rhamnolipids, pyochelin, and vancomycin with Abberior STARNHS ester dye

Biochem/physiol Actions

Adipic acid dihydrazide (ADH) is a low molecular weight compound that comprises a hydrazide group at each end. This leads to the supply of extra adsorption sites for heavy metals that maintain or elevate the adsorption capacities of the cross-linked adsorbents. ADH is used as a crosslinker in various fields, like making mechanical latexes films and injectable oxidized hyaluronic acid hydrogel.

Other Notes

Note that the hydrazone bond may be stabilized by selective reduction using, for example, sodium cyanoborohydride.

Safety Information

• Pictograms: GHS09
• Hazard Statements: H411
• Precautionary Statements: P273 - P391 - P501
• Hazard Classifications: Aquatic Chronic 2
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): 302.0 °F - closed cup
• Flash Point(C): 150 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves