D-alpha-Amino-epsilon-caprolactam

D-alpha-Amino-epsilon-caprolactam Property

Melting point:

97-101 °C

Boiling point:

315.1±35.0 °C(Predicted)

Density 

1.031±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

DMF: 30 mg/ml,DMSO: 30 mg/ml,Ethanol: 30 mg/ml,PBS (pH 7.2): 10 mg/ml

form 

A neat oil

pka

16.06±0.40(Predicted)

InChI

InChI=1S/C6H12N2O/c7-5-3-1-2-4-8-6(5)9/h5H,1-4,7H2,(H,8,9)/t5-/m1/s1

InChIKey

BOWUOGIPSRVRSJ-RXMQYKEDSA-N

SMILES

N1CCCC[C@@H](N)C1=O

Safety

RIDADR 

1759

HazardClass 

8

PackingGroup 

III

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

D-alpha-Amino-epsilon-caprolactam Chemical Properties,Usage,Production

Uses

(S)-3-Amino-2-azepanone is a useful research chemical. It is used as an intermediate in the synthesis of bengamide E analogs and capuramycin and its analogs as antibacterial agents. (R)-3-Amino-2-azepanone is used as an intermediate for the synthesis of β-oxocarboxamides as antiviral agents.

Definition

ChEBI: D-2-aminohexano-6-lactam is a 2-aminohexano-6-lactam. It is a conjugate base of a D-2-ammoniohexano-6-lactam. It is an enantiomer of a L-2-aminohexano-6-lactam.

Synthesis

General procedure for the synthesis of (R)-3-amino-2-caprolactam from L-lysine hydrochloride: 30 g (164 mmol) of L-lysine hydrochloride and 150 mL of 1,2-propanediol as a solvent were added to a 250 mL three-neck flask. Under stirring conditions, 6.57 g of sodium hydroxide was slowly added with continuous stirring until complete dissolution. Subsequently, the reaction mixture was heated to reflux and the reflux reaction was maintained for 5 hours, during which time the water generated was removed by means of a water separator and the progress of the reaction was monitored by thin-layer chromatography (TLC) until the reaction was complete. Upon completion of the reaction, the mixture was cooled to room temperature and the by-product sodium chloride was removed by filtration. The filtrate was acidified dropwise by adding 6 mol/L aqueous hydrochloric acid to the filtrate, followed by a back-extraction operation. The aqueous phase was collected, dried over anhydrous sodium sulfate, and recrystallized by adding appropriate amount of ethanol to finally obtain 21.9 g of white solid product (R)-α-amino caprolactam in 81% yield.

References

[1] Patent: CN106946779, 2017, A. Location in patent: Paragraph 0031; 0033; 0034