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Adipic dihydrazide (ADH) is a white to slightly yellow crystalline powder that serves as a versatile hydrazide cross-linking agent. It is particularly effective in water-based paint emulsions and has been widely utilized in various applications due to its ability to react with aldehydes, forming relatively stable hydrazone linkages.

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  • 1071-93-8 Structure
  • Basic information

    1. Product Name: Adipic dihydrazide
    2. Synonyms: ZERENEX ZX005030;HEXANEDIOIC ACID, DIHYDRAZIDE;HEXANEDIHYDRAZIDE;HEXANEDIOHYDRAZIDE;ADH;ADIPINIC DIHYDRAZIDE;ADIPIC DIHYDRAZIDE;ADIPIC ACID DIHYDRAZIDE
    3. CAS NO:1071-93-8
    4. Molecular Formula: C6H14N4O2
    5. Molecular Weight: 174.2
    6. EINECS: 213-999-5
    7. Product Categories: Industrial/Fine Chemicals;Aromatic Hydrazides, Hydrazines, Hydrazones and Oximes;Ester series;Homobifunctional Cross-Linking Reagents;Crosslinking;Protein Modification;Carbonyl Compounds;Hydrazides;Organic Building Blocks;Pharmaceutical intermediates;chemical
    8. Mol File: 1071-93-8.mol
  • Chemical Properties

    1. Melting Point: 180-182 °C(lit.)
    2. Boiling Point: 305.18°C (rough estimate)
    3. Flash Point: 150 °C
    4. Appearance: White to slightly yellow/Crystalline Powder
    5. Density: 1.2297 (rough estimate)
    6. Vapor Pressure: 6.92E-11mmHg at 25°C
    7. Refractive Index: 1.6700 (estimate)
    8. Storage Temp.: −20°C
    9. Solubility: H2O: 100 mg/mL
    10. PKA: 12.93±0.35(Predicted)
    11. Water Solubility: soluble
    12. BRN: 973863
    13. CAS DataBase Reference: Adipic dihydrazide(CAS DataBase Reference)
    14. NIST Chemistry Reference: Adipic dihydrazide(1071-93-8)
    15. EPA Substance Registry System: Adipic dihydrazide(1071-93-8)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 22-24/25
    4. WGK Germany: 3
    5. RTECS: AV1400000
    6. TSCA: Yes
    7. HazardClass: IRRITANT
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 1071-93-8(Hazardous Substances Data)

1071-93-8 Usage

Uses

Used in Formaldehyde Scavenging:
Adipic dihydrazide is used as a formaldehyde scavenger, reacting with formaldehyde to prevent its volatilization in the air. This application is crucial for reducing harmful formaldehyde emissions and improving indoor air quality.
Used in Paint and Coating Industries:
Adipic dihydrazide is employed as a paint additive and coating additive, enhancing the properties of the final product. Its use in these industries is due to its ability to cross-link water-based emulsions, providing improved durability and performance.
Used as an Intermediate:
Adipic dihydrazide is also used as an intermediate in the synthesis of various chemicals, leveraging its reactivity with aldehydes.
Used in Epoxy Resin Hardening:
Adipic dihydrazide is used as a hardener for certain epoxy resins, particularly in the production of powder coatings. Its cross-linking properties contribute to the formation of a strong and durable coating.
Used in Glycoprotein Linking:
Adipic acid dihydrazide is a homobifunctional cross-linking reagent specific for aldehydes. It is typically used in the linking of glycoproteins, such as antibodies, in a site-specific fashion following periodate oxidation. The low pKa of the hydrazide allows for convenient oxidation and coupling at pH 5.0, avoiding competition by primary amines.

Flammability and Explosibility

Nonflammable

Check Digit Verification of cas no

The CAS Registry Mumber 1071-93-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,0,7 and 1 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 1071-93:
(6*1)+(5*0)+(4*7)+(3*1)+(2*9)+(1*3)=58
58 % 10 = 8
So 1071-93-8 is a valid CAS Registry Number.
InChI:InChI=1/C6H14N4O2/c7-9-5(11)3-1-2-4-6(12)10-8/h1-4,7-8H2,(H,9,11)(H,10,12)

1071-93-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Detail
  • TCI America

  • (A0170)  Adipic Dihydrazide  >99.0%(HPLC)

  • 1071-93-8

  • 25g

  • 149.00CNY

  • Detail
  • TCI America

  • (A0170)  Adipic Dihydrazide  >99.0%(HPLC)

  • 1071-93-8

  • 250g

  • 590.00CNY

  • Detail
  • Alfa Aesar

  • (A15119)  Adipic dihydrazide, 97%   

  • 1071-93-8

  • 25g

  • 324.0CNY

  • Detail
  • Alfa Aesar

  • (A15119)  Adipic dihydrazide, 97%   

  • 1071-93-8

  • 100g

  • 1061.0CNY

  • Detail
  • Alfa Aesar

  • (A15119)  Adipic dihydrazide, 97%   

  • 1071-93-8

  • 500g

  • 4245.0CNY

  • Detail

1071-93-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Adipic dihydrazide

1.2 Other means of identification

Product number -
Other names Adipic Dihydrazide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates,Paint additives and coating additives not described by other categories
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1071-93-8 SDS

1071-93-8Relevant articles and documents

Enzymatic hydrazinolysis of diesters and synthesis of N-aminosuccinimide derivatives

Astorga,Rebolledo,Gotor

, p. 287 - 289 (1993)

Selective hydrazinolysis of diesters is catalyzed by PS lipase. This enzyme is an efficient catalyst for the preparation of N-aminosuccinimide derivatives.

Synthesis, characterization, reactivity, and electrochemical studies of manganese(IV) complexes of bis(2-hydroxy-1-naphthaldehyde)adipoyldihydrazone

Lal,Basumatary,Chanu,Lemtur,Asthana,Kumar,De

, p. 300 - 313 (2011)

Manganese(IV) complexes [MnIV(npah)(H2O)2] (1) and [MnIV(npah)(A)2] nH2O (where A = py (2), 2-pic (3), 3-pic (4), 4-pic (5)) and MnIV(npah)(NN)] (NN = bpy (6) and phen (7)) have been synthesized from bis(2-hydroxy-1-naphthaldehyde) adipoyldihydrazone in methanol. The composition of the complexes has been established by elemental analyses. Complex 3 has been characterized by mass spectral data also. Structural assessment of the complexes has been based on data from molar conductance, magnetic moment, electronic, electron paramagnetic resonance, and infrared (IR) spectral studies. Molar conductances of the complexes in DMSO suggest non-electrolytes. Magnetic moment and EPR studies suggest +4 oxidation state for manganese in these complexes. Electronic spectral studies suggest six-coordinate octahedral geometry around the metal ions. IR spectra reveal that H4npah coordinates to the metal in enol form. Reaction of the complexes with benzyl alcohol and SO2 has been investigated. Cyclic voltammetric studies of the complexes have also been carried out.

Coordination polymeric fluorescent gel: effect of removal of branch substituents of the central core over properties

Pandey, Vinay Kumar,Singh, Vikas Kumar,Chandra, Subhash,Hasan, Syed Hadi

, p. 1537 - 1546 (2019)

A fluorescent gel has been prepared by deprotonation of non-fluorescent adipic acid derived ligand (H4AL) with LiOH followed by coordination with Cd(II) in DMF. The mechanism of gelation is examined by IR, 1H NMR, UV-vis, Job’s plot, PXRD, SEM and TEM. Chelation enhanced fluorescence by Cd(II) has been established by fluorescence experiments. In addition to synthesis and characterization of this gel, we compared the gel properties by varying the core of the ligand using citric (H6CL) acid derivatives.

Solid macrosupports for immunoassay, modified with polysaccharides

Shmanai,Litoshko

, p. 1348 - 1352 (2001)

A series of water-soluble derivatives of natural and synthetic polysaccharides (dextran, pectins, Phycoll, pullulan, hydroxyethyl starch) containing aldehyde, hydrazide, sulfonate, and hydrazine groups were prepared.

Synthesis, and characterization of low- and high-spin manganese(II) complexes of polyfunctional adipoyldihydrazone: Effect of coordination of N-donor ligands on stereo-redox chemistry

Basumatary, Debajani,Lal, Ram Ashray,Kumar, Arvind

, p. 122 - 129 (2015)

Manganese(II) complexes [MnII(npahH2)] (1), [MnII(npahH2)(A)2] and [MnII(npahH2)(NN)] (where A = pyridine, (2); 2-picoline, (3); 3-picoline, (4); 4-picoline, (5) and NN = 2,2′ bipyridine, (6); 1,10-phenanthroline, (7)) have been synthesized from bis(2-hydroxy-1-naphthaldehyde)adipoyldihydrazone (npahH4) in methanol. The composition of metal complexes has been established by elemental analyses. Complexes (1) and (3) have been characterized by mass spectral data also. Structural assessments of the complexes have been based on data obtained from molar conductance, magnetic moment, electronic, electron paramagnetic resonance and infrared spectral studies. Conductivity measurements in DMSO suggest that they are non-electrolyte. Electronic spectral studies suggest a six-coordinate octahedral geometry around the manganese center in complexes (2) to (7) and square-planar geometry in complex (1). IR spectral studies reveal that the dihydrazone coordinates to the metal in keto form with an anti-cis configuration. Magnetic moment, and EPR studies suggest manganese in +2 oxidation state in all complexes with high-spin distorted octahedral stereochemistry in complexes (2-7) while low-spin square-planar stereochemistry is involved with significant metal-metal interactions in the solid state in complex (1). Cyclic voltammetric studies reveal that the metal center cycles among the MnII → MnI → Mn0 in complexes (2) to (7) and among MnII → MnI oxidation states in complex (1).

Ternary SO42?–ZrO2–TiO2 Solid Super Acid Catalyst for One-Step Synthesis of Adipicdihydrazide

Guo, Zhenmei,Liu, Baoquan,Liu, Xiangxue,Lv, Zhiguo,Wang, Ke,Zhang, Chao

, (2021/11/22)

An efficient SO42?–ZrO2–TiO2 super acid catalyst was fabricated via simple impregnation precipitation strategy and applied in one-step synthesis of adipicdihydrazide (ADH). The purity and yield of ADH reached up to 97.5 and 96.7% respectively without separation treatment. After five recycling of the catalyst, the ADH yield still remained 82%, revealing the excellent stability performance of SO42?–ZrO2–TiO2 catalyst. Further, the excellent catalytic performance could be attributed to (1) solid super acid existed in SO42?–ZrO2–TiO2; (2) robust SO42? maintained in ZrO2–TiO2; (3) the accelerated cleavage of C =O and improved nucleophilic attack reaction rate of hydrazine hydrate by vast proton produced. DFT calculation was employed to further analyze the electron cloud change of ZrO2–TiO2 with the SO42? introduction and calculate the adsorption energy barrier of SO42?–ZrO2–TiO2 for AA (? 2.08?eV). Graphical Abstract: An efficient SO42?-ZrO2-TiO2 super acid catalyst was fabricated via simple impregnation precipitation strategy and applied in one-step synthesie of adipic dihydrazide. The resulting acidic centers of SO42?-ZrO2-TiO2 attracted electrons from surrounding water molecules to restore neutrality. Meanwhile, a large amount of H+ floated around in the reaction system, which could break the C=O double bond and improve the adipic acid conversion rate. The extreme catalytic activity was based on the fact that the electronic effects of SO42? and ZrO2-TiO2 facilitated the interaction with H+ in adipic acid and reduced hydrazine hydrate nucleophilic attack difficulty.[Figure not available: see fulltext.].

Ultralow-Molecular-Weight Stimuli-Responsive and Multifunctional Supramolecular Gels Based on Monomers and Trimers of Hydrazides

Wu, Dehua,Song, Jintong,Qu, Lang,Zhou, Weilan,Wang, Lei,Zhou, Xiangge,Xiang, Haifeng

supporting information, p. 3370 - 3378 (2020/10/02)

The simpler, the better. A series of simple, neutral and ultralow-molecular-weight (MW: 140–200) hydrazide-derived supramolecular gelators have been designed and synthesized in two straightforward steps. For non-conjugated cyclohexane-derived hydrazides, their monomers can self-assemble to form gels through intermolecular hydrogen bonds and dipole-dipole interactions. Significantly, conjugated phthalhydrazide can self-aggregate into planar and circular trimers through intermolecular hydrogen bonds and then self-assemble to form gels through intermolecular π–π stacking interactions. It is interesting that these simple gelators exhibit unusual properties, such as self-healing, multi-response fluorescence, and visual and selective recognition of chiral (R)/(S)-1,1′-binaphthalene-2,2′-diamine and S2? through much different times of gel re-formation and blue-green color change, respectively. These results underline the importance of supramolecular gels and extend the scope of supramolecular gelators.

PRECURSOR COMPOUNDS OF ESTER COMPOUNDS

-

Paragraph 00109; 00118-00119; 00120, (2020/12/30)

The present disclosure relates to compounds of the formula (I) which are precursor compounds of esters, whereby upon hydrolysis of the precursor compound, an ester compound is released. This ester precursor approach can be useful for applications where controlled release of, for example, ethyl formate, is beneficial.

ISOCYANATES, DERIVATIVES, AND PROCESSES FOR PRODUCING THE SAME

-

Paragraph 0054, (2019/04/27)

The present invention is directed to processes for producing isocyanates and isocyanate derivatives from epoxide and carbon monoxide reagents. In preferred embodiments, the processes include a step for providing carbonylation of an epoxide reagent with a carbon monoxide reagent to produce a beta-lactone intermediate. In certain preferred embodiments, further carbonylation of a beta-lactone intermediate produces a succinic anhydride intermediate. The processes of the present invention include steps for rearranging beta-lactone intermediates and/or succinic anhydride intermediates to produce isocyanate products and/or isocyanate derivatives. In certain preferred embodiments, the isocyanate products may be copolymerized with polyol oligomers to provide polyurethane products.

Continuous hydrazide preparation method

-

Paragraph 0060-0062, (2019/04/17)

The invention relates to a continuous hydrazide preparation method. The preparation method includes: in a micro-channel reactor or a pipeline reactor, subjecting esters, anhydrides or acyl chloride tocontinuous reaction with hydrazine or solution of hydrazine under a solvent-free condition or in a solvent to prepare a hydrazide compound. The preparation method is simple, short in technical process, less in waste gas, wastewater and industrial residues, beneficial to environmental production and suitable for industrial production. The adopted reactor is short in reaction time, high in safety and capable of realizing continuous production. The adopted reactor is high in workshop space utilization rate, and large-scale production can be realized. By adoption of the preparation method, solvent recycling can be realized, and production cost is reduced; in addition, high raw material conversion rate, high quality stability and high purity are realized.

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