2014-58-6

Basic information

• Product Name: HEXANOICACID,6-[(6-AMINO-1-OXOHEXYL)AMINO]-
• Synonyms: HEXANOICACID,6-[(6-AMINO-1-OXOHEXYL)AMINO]-;6-(6-aminohexanamido)hexanoic acid;6-(6-Aminohexanoylamino)hexanoic acid;N-(6'-Aminocaproyl)-6-aminocaproic Acid;6-Aminocaproic acid dimer;Aminocaproic acid Impurity A
• CAS NO: 2014-58-6
• Molecular Formula: C₁₂H₂₄N₂O₃
• Molecular Weight: 244.33056
• Mol File: 2014-58-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 197-198 °C
• Boiling Point: 485.9±30.0 °C(Predicted)
• Appearance: /
• Density: 1.058±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: Chloroform (Very Slightly), Methanol (Slightly), Water (Slightly)
• PKA: 4.75±0.10(Predicted)
• CAS DataBase Reference: HEXANOICACID,6-[(6-AMINO-1-OXOHEXYL)AMINO]-(CAS DataBase Reference)
• NIST Chemistry Reference: HEXANOICACID,6-[(6-AMINO-1-OXOHEXYL)AMINO]-(2014-58-6)
• EPA Substance Registry System: HEXANOICACID,6-[(6-AMINO-1-OXOHEXYL)AMINO]-(2014-58-6)

Safety Data

• Hazardous Substances Data: 2014-58-6(Hazardous Substances Data)

Usage

Description

HEXANOICACID,6-[(6-AMINO-1-OXOHEXYL)AMINO]-, also known as 6-Aminocaproic Acid Dimer, is an organic compound formed by the condensation of two 6-aminocaproic acid molecules. It possesses a hexanoic acid backbone with an amino group attached to the sixth carbon, and another amino group connected to the first one through an amide linkage. This unique structure endows it with potential applications in various fields.

Uses

Used in Chemical Synthesis:
HEXANOICACID,6-[(6-AMINO-1-OXOHEXYL)AMINO]is used as a reactant in the formation of 3-hydroxy-3,4-dicarboxy-butanamide-N-hexanoic acid, a compound that may have potential applications in various industries, such as pharmaceuticals or materials science.
Used in Pharmaceutical Industry:
HEXANOICACID,6-[(6-AMINO-1-OXOHEXYL)AMINO]can be employed as a building block or intermediate in the synthesis of pharmaceutical compounds, taking advantage of its reactive functional groups and unique molecular structure.
Used in Material Science:
Due to its specific chemical properties, HEXANOICACID,6-[(6-AMINO-1-OXOHEXYL)AMINO]may be utilized in the development of novel materials with tailored properties, such as polymers, coatings, or adhesives.

Upstream product

• 60-32-2 6-aminohexanoic acid 
• 56403-09-9 1,8-diazacyclotetradecane-2,9-dione 
• 2899-61-8 benzyl 6-(6-(benzyloxycarbonylamino)hexanamido)hexanoate 
• 31968-60-2 6-phthalimidohexanoyl chloride 
• 4443-26-9 6-phthalimidohexanoic acid 
• 124158-33-4 6-(6-benzyloxycarbonylamino-hexanoylamino)-hexanoic acid ethyl ester 
• 1947-00-8 6-(benzyloxycarbonylamino)hexanoic acid 
• 4644-75-1 6-benzyloxycarbonylaminocapronoyl chloride 
• 148533-77-1 6-<6-(2,3-dihydro-1,3-dioxo-1H-isoindol-2-yl)hexanamido>hexanoic acid 
• 49701-55-5 13-benzyloxycarbonylamino-8-oxo-7-azatridecanoic acid 
• 220933-96-0 6-(6-bromo-hexanoylamino)-hexanoic acid 

Downstream Products

• 117025-58-8 [4]6-benzyloxycarbonylamino-lin-tri[1=>6]hexanoylamino-hexanoic acid 
• 5776-78-3 6-[6-(6-amino-hexanoylamino)-hexanoylamino]-hexanoic acid 
• 56403-09-9 1,8-diazacyclotetradecane-2,9-dione 

Relevant articles and documents

In situ formation of N-trifluoroacetoxy succinimide (TFA-NHS): One-pot formation of succinimidyl esters, N-trifluoroacetyl amino acid succinimidyl esters, and N-maleoyl amino acid succinimidyl esters

A method for the in situ formation of N-trifluoroacetoxy succinimide (TFA-NHS) and its application in the formation of succinimidyl esters is presented. The developed method provides N-trifluoroacetyl and N-maleoyl amino acid succinimidyl esters from a variety of amino acids using a one-pot, high-yielding protocol. Investigations into the formation of an N-maleoyl amino acid succinimidyl ester supported the proposal of a revised reaction mechanism, and contributed to the optimization of the reaction conditions.

Enzymatic synthesis of nylon-6 units in organic solvents containing low concentrations of water

NylB′ carboxylesterase, which is 88% homologous to functional 6-aminohexanoate-dimer hydrolase (NylB) from Arthrobacter sp., possesses trace synthetic activity [0.0004μmolmin-1mg-1 (U/mg)] from 6-aminohexanoate (Ahx) to its oligomers in 90% tert-butyl alcohol. The synthetic activity and the ratio of the synthetic activity to the hydrolytic activity were significantly affected by amino acid substitutions at positions 181, 266 and 370. The synthetic activity was enhanced to 2.7U/mg by G181D-H266N substitutions, and the activity was further enhanced in the G181D-H266N-D370Y triple mutant to a level approximately 104-fold greater than the parental carboxylesterase form (3.4U/mg), which was nearly equal to the ordinary hydrolytic activity in water (type A-mutants). Type A-mutants possessed more than 50% of the 6-aminohexanoate-linear dimer (Ald)-hydrolytic activity at 0-70% tert-butyl alcohol, but the synthetic reaction became predominant at 85-90% tert-butyl alcohol. In contrast, type B-mutants (G181E-H266N and G181N-H266N) possessed quite low levels of Ald-hydrolytic activity (a type C-mutant (R187S-F264C-D370Y), the Ald-hydrolytic activity was enhanced to approximately 80-fold that of the parental carboxylesterase, but the mutant barely demonstrated any synthetic activity. On the basis of the three-dimensional structure of the Ald-bound enzyme and a kinetic study for typical mutant enzymes, we propose that the efficient enzymatic syntheses of nylon-6 units were achieved by (i) stable binding of the 1st-Ahx at the N-terminal region with Asp181, (ii) interaction of the 2nd-Ahx at the C-terminal region with Tyr370, and (iii) motion of Tyr170 that generated a closed form in the catalytic center of Ald hydrolase.