29426-64-0

Basic information

• Product Name: DL-alpha-Amino-epsilon-caprolactam hydrochloride
• Synonyms: dl-α-amino-ε-caprolactam hydrochloride;(±)-3-Aminohexahydro-2H-azepin-2-one hydrochloride, 3-Amino-2-oxohexamethyleneimine hydrochloride, DL-Lysine lactam hydrochloride;3-AMinoazepan-2-one hydrochloride;DL-3-Aminohexahydro-2-azepinone Hydrochloride DL-3-Amino-2-oxohexamethyleneimine Hydrochloride;2H-Azepin-2-one, 3-aMinohexahydro-, hydrochloride;2H-Azepin-2-one,3-aMinohexahydro-, hydrochloride (1:1);3-AMinoazepan-2-one HCl;DL-3-Amino-2-oxohexamethyleneimine hydrochloride
• CAS NO: 29426-64-0
• Molecular Formula: C₆H₁₂N₂O*ClH
• Molecular Weight: 0
• Product Categories: Building Blocks;Carbonyl Compounds;Chemical Synthesis;Lactams;Organic Building Blocks
• Mol File: 29426-64-0.mol

Chemical Properties

• Melting Point: 294°C(lit.)
• Boiling Point: 340.3°C at 760 mmHg
• Flash Point: 159.6°C
• Appearance: /
• Vapor Pressure: 6.17E-05mmHg at 25°C
• Storage Temp.: 2-8°C
• CAS DataBase Reference: DL-alpha-Amino-epsilon-caprolactam hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: DL-alpha-Amino-epsilon-caprolactam hydrochloride(29426-64-0)
• EPA Substance Registry System: DL-alpha-Amino-epsilon-caprolactam hydrochloride(29426-64-0)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 29426-64-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
DL-alpha-Amino-epsilon-caprolactam hydrochloride is used as a pharmaceutical intermediate for the production of tranexamic acid and other antifibrinolytic agents, which are essential in managing excessive bleeding and clotting disorders.
Used in Stabilization of Pharmaceuticals:
DL-alpha-Amino-epsilon-caprolactam hydrochloride is employed as a stabilizer in pharmaceutical formulations to enhance the shelf life and maintain the quality of the final product.
Used in Chemical Synthesis:
DL-alpha-Amino-epsilon-caprolactam hydrochloride is utilized as a reagent in various chemical synthesis processes, contributing to the development of new compounds and materials.
Used in Hemostasis:
Due to its hemostatic properties, DL-alpha-Amino-epsilon-caprolactam hydrochloride is used to prevent or control bleeding in patients with specific medical conditions, such as hemophilia and other clotting disorders, thereby improving patient outcomes and safety.

InChI:InChI=1/C6H12N2O.ClH/c7-5-3-1-2-4-8-6(5)9;/h5H,1-4,7H2,(H,8,9);1H

Upstream product

• 657-27-2 L-Lysine hydrochloride 
• 56-87-1 L-lysine 
• 6804-88-2 α-nitrocaprolactam 
• 26081-03-8 (-)-3-aminocaprolactam hydrochloride 
• 13515-95-2 lysine methyl ester dihydrochloride 

Downstream Products

• 69154-03-6 DL-3-aminohexahydro-1H-azepin 
• 179534-94-2 (R)-α-triphenylmethylamino-ε-caprolactam 
• 70394-23-9 α-dimethylamino-ε-caprolactam 
• 105-60-2 caprolactam 
• 103478-12-2 (3S)-3-benzyloxycarbonylamino-2-perhydroazepinone 
• 70394-23-9 α-dimethylamino-ε-caprolactam 
• 26081-03-8 3-Amino-azepan-2-one; hydrochloride 
• 1269620-04-3 (2R)-benzyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-oxo-5-((2-oxoazepan-3-yl)amino)pentanoate 
• 76944-95-1 tert-butyl N-[(3S)-2-oxoazepan-3-yl]carbamate 
• 1067658-71-2 tert-butyl methyl((S)-azepan-2-one-3-ylamino-(S)-oxo-3-phenylpropan-2-yl)carbamate 
• 1067658-75-6 N-methyl-((S)-azepan-2-one-3-ylamino-(R)-oxo-3-phenylpropan-2-yl)dec-9-enamide 
• 1070777-03-5 N-methyl-((S)-azepan-2-one-3-ylamino-(S)-oxo-3-phenylpropan-2-yl)dec-9-enamide 
• 1067659-00-0 tert-butyl methyl((S)-azepan-2-one-3-ylamino-(R)-oxo-3-phenylpropan-2-yl)carbamate 
• 956109-57-2 (S)-3-amino-1-methylazepan-2-one HCl salt 

Relevant articles and documents

Protecting-Group-Free Amidation of Amino Acids using Lewis Acid Catalysts

Amidation of unprotected amino acids has been investigated using a variety of ‘classical“ coupling reagents, stoichiometric or catalytic group(IV) metal salts, and boron Lewis acids. The scope of the reaction was explored through the attempted synthesis of amides derived from twenty natural, and several unnatural, amino acids, as well as a wide selection of primary and secondary amines. The study also examines the synthesis of medicinally relevant compounds, and the scalability of this direct amidation approach. Finally, we provide insight into the chemoselectivity observed in these reactions.

Novel chiral derivatizing agents for 1H NMR determination of enantiomeric purities of carboxylic acids

(S)-4-(3-Aminopyrrolidin-1-yl)coumarin (1), (S)-4-(3-aminopiperidin-1-yl)coumarin (4), and (S)-4-(3-aminoazepan-1-yl)coumarin (7), prepared from 4-chlorocoumarin and (S)-pyrrolidin-3-amine, (S)-piperidin-3-amine, and (S)-azepan-3-amine, respectively, were proven to be versatile and reliable 1H NMR optical purity determination agents for chiral carboxylic acids.

SYNTHESIS OF CAPROLACTAM FROM LYSINE

In various embodiments, the present invention can involve a method of synthesizing α-amino-ε -caprolactam. The method can comprise heating a salt of L-lysine in a solvent comprising an alcohol. In other embodiments, the present invention can involve methods for synthesizing ε-caprolactam. The methods can comprise heating a salt of L-lysine in a solvent comprising an alcohol and deaminating the reaction product. In various embodiments, the invention can include methods of converting biomass into nylon 6. The methods can comprise heating L-lysine in a solvent comprising an alcohol to produce α-amino -ε- caprolactam, deaminating to produce ε-caprolactam and polymerizing into nylon 6, wherein the L-lysine is derived from the biomass. In other embodiments, the present invention can include methods of making nylon 6. The methods can comprise synthesizing ε-caprolactam and then polymerizing, wherein the ε--caprolactam is derived from L-lysine.

ANTI-INFLAMMATORY AGENTS

The invention relates to the use of 3-aminocaprolactam derivatives for preparing a medicament intended to prevent or treat inflammatory disorders, and uses compounds of general formula (I) or a pharmaceutically acceptable salts thereof; wherein X is -CO-R1 or-S02-R2, and R1 and R2 are carbonaceous substituents.