Adipic dihydrazide

Base Information

• Chemical Name: Adipic dihydrazide
• CAS No.: 1071-93-8
• Deprecated CAS: 124246-54-4,98152-55-7
• Molecular Formula: C6H14N4O2
• Molecular Weight: 174.203
• Hs Code.: 29280090
• European Community (EC) Number: 213-999-5
• NSC Number: 29542,3378
• UNII: VK98I9YW5M
• DSSTox Substance ID: DTXSID0044361
• Nikkaji Number: J36.606D
• Wikipedia: Adipic_acid_dihydrazide
• Wikidata: Q4682936
• NCI Thesaurus Code: C83519
• ChEMBL ID: CHEMBL3185968
• Mol file: 1071-93-8.mol

Synonyms:adipic acid dihydrazide;adipic dihydrazide

Chemical Property of Adipic dihydrazide

Chemical Property:

• Appearance/Colour: white to slightly yellow crystalline powder
• Vapor Pressure: 6.92E-11mmHg at 25°C
• Melting Point: 175-182 °C
• Refractive Index: 1.513
• Boiling Point: 519.3 °C at 760 mmHg
• PKA: 12.93±0.35(Predicted)
• Flash Point: 267.9 °C
• PSA: 110.24000
• Density: 1.186 g/cm³
• LogP: 0.70900
• Storage Temp.: −20°C
• Solubility.: H2O: 100 mg/mL
• Water Solubility.: soluble
• XLogP3: -2.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 174.11167570
• Heavy Atom Count: 12
• Complexity: 142

Purity/Quality:

98% ^*data from raw suppliers

Adipic dihydrazide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(CCC(=O)NN)CC(=O)NN
• Description: Adipic dihydrazide (ADH) is the most suitable hydrazide cross-linking agent, and ADH has been widely used in water-based paint emulsions in combination with diacetone acrylamide. ADH is weakly alkaline, and there is a possibility of agglomeration when solid ADH is added directly to the emulsion, so usually ADH should be dissolved in hot water before use.
• Uses: Adipic dihydrazide is used as a formaldehyde scavenger and reacts with formaldehyde, thereby preventing the volatilizing of formaldehyde in the air. It is also employed as a paint additive and coating additive. It is also used as an intermediate. Further, it is used for cross-linking water-based emulsions and as a hardener for certain epoxy resins, which finds application in powder coating. Adipic acid dihydrazide is a homobifunctional cross-linking reagent specific for aldehydes resulting in relatively stable hydrazone linkages. Adipic acid dihydrazide is typically, used in the linking of glycoproteins, such as antibodies, in a site specific fashion following periodate oxidation. Oxidation and coupling may conveniently be performed at pH 5.0 due to the low pKa of the hydrazide which avoids competition by primary amines.

Technology Process of Adipic dihydrazide

There total 11 articles about Adipic dihydrazide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.2%

hexanedioic acid dimethyl ester (627-93-0) → adipic acid dihydrazide (1071-93-8,98152-55-7)

Guidance literature:

hexanedioic acid dimethyl ester; With propan-2-one azine; at 50 - 120 ℃;

at 125 ℃; for 3h; Temperature;

Reference yield: 96.0%

Adipic acid (124-04-9) → adipic acid dihydrazide (1071-93-8,98152-55-7)

Guidance literature:

With carbazic acid; In neat (no solvent); at 100 ℃; for 5h; Temperature; Solvent; Reagent/catalyst; Green chemistry;

Reference yield: 96.0%

Adipic acid (124-04-9) + hydrazonium hydrazincarbonate (10195-79-6) → adipic acid dihydrazide (1071-93-8,98152-55-7)

Guidance literature:

In neat (no solvent); at 100 ℃; for 5h;

upstream raw materials:

diethyl adipate

hexanedioic acid dimethyl ester

1-N',6-N'-di[benz-(E)-ylidene]hexanedihydrazide

Adipic acid

Downstream raw materials:

1-N',6-N'-di[benz-(E)-ylidene]hexanedihydrazide

4,4'-Di(3,4-dichlorophenyl)bis-adipylthiosemicarbazide

N,N'-diacetyladipohydrazide

Refernces

• 1、 Lal,Basumatary,Chanu,Lemtur,Asthana,Kumar,De. "Synthesis, characterization, reactivity, and electrochemical studies of manganese(IV) complexes of bis(2-hydroxy-1-naphthaldehyde)adipoyldihydrazone". . p. 300 - 313. Retrieved 2011.
• 2、 Shmanai,Litoshko. "Solid macrosupports for immunoassay, modified with polysaccharides". . p. 1348 - 1352. Retrieved 2001.
• 3、 Guo, Zhenmei,Liu, Baoquan,Liu, Xiangxue,Lv, Zhiguo,Wang, Ke,Zhang, Chao. "Ternary SO42?–ZrO2–TiO2 Solid Super Acid Catalyst for One-Step Synthesis of Adipicdihydrazide". . . Retrieved 2021/11/22.
• 4、 -. "PRECURSOR COMPOUNDS OF ESTER COMPOUNDS". Paragraph 00133-00134. . Retrieved 2020/12/30.