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Adipic dihydrazide

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CAS:1071-93-8
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Adipic dihydrazide Basic information
Product Name:Adipic dihydrazide
Synonyms:ADH;ADIPINIC DIHYDRAZIDE;ADIPIC DIHYDRAZIDE;ADIPIC ACID DIHYDRAZIDE;ADIPIC ACID DIHYDRIZIDE;adipoyl hydrazide;ADIPODIHYDRAZIDE;Adipohydrazide
CAS:1071-93-8
MF:C6H14N4O2
MW:174.2
EINECS:213-999-5
Product Categories:Pharmaceutical intermediates;chemical;Homobifunctional Cross-Linking Reagents;Crosslinking;Protein Modification;Carbonyl Compounds;Hydrazides;Organic Building Blocks;Aromatic Hydrazides, Hydrazines, Hydrazones and Oximes;Industrial/Fine Chemicals;Ester series;bc0001;1071-93-8
Mol File:1071-93-8.mol
Adipic dihydrazide Structure
Adipic dihydrazide Chemical Properties
Melting point 180-182 °C (lit.)
Boiling point 305.18°C (rough estimate)
density 1.2297 (rough estimate)
vapor pressure 0Pa at 25℃
refractive index 1.6700 (estimate)
Fp 150 °C
storage temp. -20°C
solubility H2O: 100 mg/mL
pka12.93±0.35(Predicted)
form Crystalline Powder
color White to slightly yellow
Water Solubility soluble
BRN 973863
Cosmetics Ingredients FunctionsFRAGRANCE
MOISTURISING
Cosmetic Ingredient Review (CIR)Adipic dihydrazide (1071-93-8)
InChI1S/C6H14N4O2/c7-9-5(11)3-1-2-4-6(12)10-8/h1-4,7-8H2,(H,9,11)(H,10,12)
InChIKeyIBVAQQYNSHJXBV-UHFFFAOYSA-N
SMILESNNC(=O)CCCCC(=O)NN
LogP-2.7 at 20℃
CAS DataBase Reference1071-93-8(CAS DataBase Reference)
NIST Chemistry ReferenceAdipic dihydrazide(1071-93-8)
EPA Substance Registry SystemHexanedioic acid, dihydrazide (1071-93-8)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 22-24/25
WGK Germany 3
RTECS AV1400000
Autoignition Temperature360 °C
TSCA TSCA listed
HazardClass IRRITANT
HS Code 29280090
Storage Class11 - Combustible Solids
Hazard ClassificationsAquatic Chronic 2
MSDS Information
ProviderLanguage
Hexanedioic acid dihydrazide English
SigmaAldrich English
ACROS English
ALFA English
Adipic dihydrazide Usage And Synthesis
DescriptionAdipic 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.
Chemical Propertieswhite to slightly yellow crystalline powder
UsesAdipic 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.
UsesAdipic 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.
Flammability and ExplosibilityNon flammable
reaction suitabilityreagent type: cross-linking reagent
Synthesis
Diethyl adipate

141-28-6

Adipic dihydrazide

1071-93-8

General method: 7.6 g (100.0 mmol) of solid hydrazine (H3N + NHCO2-) was mixed with adipic acid (7.3 g, 50.0 mmol) in a mortar and pestle under solvent-free conditions for 10 min, followed by a stirring reaction for 5 h at 100 °C. The structure and composition of the reaction products were confirmed by 400 MHz NMR (nuclear magnetic resonance) and elemental analysis. The analysis showed that the product was hexanedihydrazide (C6H14N4O2) with ≥96% conversion and ≥95% yield (8.27 g). Alternative method: 10 g of decane was used as solvent and the reaction conditions were adjusted to stirring at 110 °C for 12 h, followed by filtration and separation operations. The rest of the steps were the same as in the generalized method. The product was analyzed as hexanedihydrazide (C6H14N4O2) with 97% conversion and 93% yield. Substitution: 5.0 g (100.0 mmol) of hydrazine hydrate was used in place of the solid hydrazine and 10.12 g (100.0 mmol) of diethyl adipate was used in place of adipic acid. The reaction was stirred at 75 °C for 5 h under the condition of 10 g ethanol as solvent. The product was analyzed as hexanedihydrazide (C6H14N4O2) with 89% conversion and 83% yield.

References[1] Patent: KR2015/88523, 2015, A. Location in patent: Paragraph 0128; 0137; 0148-0149
[2] Organic Syntheses, 1956, vol. 36, p. 72,Note 7
[3] Justus Liebigs Annalen der Chemie, 1929, vol. 475, p. 122
[4] Journal fuer Praktische Chemie (Leipzig), 1915, vol. <2> 91, p. 23
[5] Journal fuer Praktische Chemie (Leipzig), 1981, vol. 323, # 3, p. 360 - 366
Adipic dihydrazide Preparation Products And Raw materials
Raw materialsDiethyl adipate-->Adipic acid-->Dimethyl adipate-->Hydrazinecarboxylic acid, compd. with hydrazine (1:1)-->Ethanol-->Hydrazine hydrate
Tag:Adipic dihydrazide(1071-93-8) Related Product Information
Adipic acid Folic acid Butanedihydrazide METHOXYFENOZIDE Maleic hydrazide Tebufenozide Hyaluronic acid Oxalyl dihydrazide Ethyl 2-(Chlorosulfonyl)acetate DIPHENYLCARBAZONE Decanedihydrazide 1,5-Diphenylcarbazide Carbohydrazide Dimethyl adipate antioxidant 1024 Citric acid Ascoric Acid Adipic dihydrazide Adipic Acid Dihydrazide

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