3644-93-7

Basic information

• Product Name: N,N,N',N'-tetraMethylhexanediaMide
• Synonyms: N,N,N',N'-tetraMethylhexanediaMide;N1,N1,N6,N6-Tetramethyladipamide
• CAS NO: 3644-93-7
• Molecular Formula: C₁₀H₂₀N₂O₂
• Molecular Weight: 200.278
• Mol File: 3644-93-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 331.4°Cat760mmHg
• Flash Point: 138.7°C
• Appearance: /
• Density: 0.989g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: N,N,N',N'-tetraMethylhexanediaMide(CAS DataBase Reference)
• NIST Chemistry Reference: N,N,N',N'-tetraMethylhexanediaMide(3644-93-7)
• EPA Substance Registry System: N,N,N',N'-tetraMethylhexanediaMide(3644-93-7)

Safety Data

• Hazardous Substances Data: 3644-93-7(Hazardous Substances Data)

Usage

General Description

N,N,N',N'-tetraMethylhexanediaMide, also known as TMHDA, is a specialty chemical used as a curing agent and hardener in the production of coatings, adhesives, and composites. It is a clear, colorless to pale yellow liquid with a high boiling point and low vapor pressure, making it suitable for high-temperature applications. TMHDA is a diamine compound, which means it contains two amino groups, and its high level of molecular branching gives it exceptional thermal and chemical stability. Due to its unique structure and properties, TMHDA is valued for its ability to enhance the performance and durability of various resin systems, particularly in the aerospace, automotive, and industrial coating industries. Additionally, it is also used as a crosslinking agent in the production of specialty polymers and polyurethane foams.

Upstream product

• 627-93-0 hexanedioic acid dimethyl ester 
• 1608-26-0 Hexamethylphosphorous triamide 
• 2873-74-7 gloutaric dichloride 
• 543-20-4 succinoyl dichloride 
• 111-50-2 Adipic acid dichloride 
• 124-40-3 dimethyl amine 
• 124-04-9 Adipic acid 
• 75-36-5 acetyl chloride 
• 74-89-5 methylamine 

Downstream Products

• 111-18-2 N,N,N',N'-tetramethylhexamethylenediamine 
• 124121-65-9 Adipinsaeure-bis-

Relevant articles and documents

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PRODUCT CONTAINING DIAMIDES, METHOD FOR MAKING SAME AND USES THEREOF

The product comprises at least two diamide compounds selected from the diamide compounds of following formulae (Ia), (Ib), and (Ic): [in-line-formulae]R2R3NOC-Aa-CONR4R5??(Ia)[/in-line-formulae] [in-line-formulae]R2R3NOC-Ab-CONR4R5??(Ib)[/in-line-formulae] [in-line-formulae]R2R3NOC-Ac-CONR4R5??(Ic)[/in-line-formulae] wherein: R2, R3, R4, and R5, either identical or different, are groups selected from saturated or unsaturated, linear or branched, optionally cyclic, optionally aromatic, optionally substituted, hydrocarbon groups comprising an average number of carbon atoms ranging from 1 to 36, R2 and R3 on the one hand and R4 and R5 on the other hand may optionally form together a ring, optionally substituted and/or optionally comprising a heteroatom, andAa, Ab, and Ac are linear divalent alkyl groups, each comprising a different number of carbon atoms.

Conformation-directing effects of a single intramolecular amide-amide hydrogen bond: Variable-temperature NMR and IR studies on a homologous diamide series

We have studied intramolecular hydrogen bonding in a homologous series of diamides (compounds 1-6) in methylene chloride, 9:1 carbon tetrachloride/benzene, and acetonitrile. By correlating variable-temperature 1H NMR and IR measurements, we have shown that the temperature dependence of the amide proton NMR chemical shift (Δδ/ΔT) can provide qualitative (and in some cases quantitative) information on the thermodynamic relationship between the intramolecularly hydrogen bonded and non-hydrogen-bonded states of flexible molecules. Among the hydrogen-bonded ring sizes represented in the diamide series, the intramolecular interaction is particularly enthalpically favorable in the nine-membered hydrogen-bonded ring (compound 4). Variable-temperature IR and NMR data indicate that the internally hydrogen bonded state of diamide 4 is 1.4-1.6 kcal/mol more favorable enthalpically than the non-hydrogen-bonded state, in methylene chloride solution; the non-hydrogen-bonded state is 6.8-8.3 eu more favorable entropically in this solvent. In contrast, there appear to be much smaller enthalpy differences between the internally hydrogen bonded and non-hydrogen-bonded states of diamides 2 and 3. Our findings are important methodologically because the temperature dependences of amide proton chemical shifts are commonly used to elucidate peptide conformation in solution. Our results show that previous "rules" for the interpretation of such data are incomplete. In non-hydrogen-bonding solvents, small amide proton Δδ/ΔT values have been taken to mean that the proton is either entirely free of hydrogen bonding or completely locked in an intramolecular hydrogen bond over the temperature range studied. We demonstrate that an amide proton can be equilibrating between intramolecularly hydrogen bonded and non-hydrogen-bonded states and still manifest a small chemical shift temperature dependence (implying that the hydrogen-bonded and non-hydrogen-bonded states are of similar enthalpy).