Caprolactam

Base Information

• Chemical Name: Caprolactam
• CAS No.: 105-60-2
• Deprecated CAS: 117955-36-9,168214-28-6,2953-03-9,32838-21-4,32838-23-6,34876-18-1,168214-28-6,2953-03-9,32838-21-4,34876-18-1
• Molecular Formula: C6H11NO
• Molecular Weight: 113.159
• Hs Code.: 2933710000
• European Community (EC) Number: 919-537-5
• ICSC Number: 0118
• NSC Number: 117393,25536,4977
• UN Number: 3082
• UNII: 6879X594Z8
• DSSTox Substance ID: DTXSID4020240
• Nikkaji Number: J3.605F
• Wikipedia: Caprolactam
• Wikidata: Q409397
• Metabolomics Workbench ID: 51773
• ChEMBL ID: CHEMBL276218
• Mol file: 105-60-2.mol

Synonyms:Aminocaproic Lactam;Caprolactam;Hexahydro 2H Azepin 2 One;Hexahydro-2H-Azepin-2-One;Lactam, Aminocaproic

Chemical Property of Caprolactam

Chemical Property:

• Appearance/Colour: white crystalline solid
• Vapor Pressure: 0.00607mmHg at 25°C
• Melting Point: 68-71 °C(lit.)
• Refractive Index: 1.4935
• Boiling Point: 272.5 °C at 760 mmHg
• PKA: 16.61±0.20(Predicted)
• Flash Point: 136.7 °C
• PSA: 29.10000
• Density: 1.01 g/cm³
• LogP: 1.00540
• Water Solubility.: 4560 g/L (20℃)
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 113.084063974
• Heavy Atom Count: 8
• Complexity: 90.5

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn:Harmful
• Statements: R20/22:; R36/37/38:
• Safety Statements: S2:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Plastics & Rubber -> Other Monomers
• Canonical SMILES: C1CCC(=O)NCC1
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly when dispersed.
• Effects of Short Term Exposure: The substance is irritating to the skin, eyes and respiratory tract. The substance may cause effects on the central nervous system.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis. The substance may have effects on the nervous system and liver.

Technology Process of Caprolactam

There total 286 articles about Caprolactam which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.2%

14,15-dioxa-7-aza-dispiro[5.1.5.2]pentadecane (21842-28-4) → caprolactam (105-60-2,9012-16-2) + 11-cyanoundecanoic acid (5810-18-4) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4)

Guidance literature:

With cerium(IV) oxide; 2,2'-azobis(isobutyronitrile); at 50 ℃; for 12h; Reagent/catalyst; Temperature; Inert atmosphere;

Reference yield: 99.0%

methyl 6-oxohexanoate (6654-36-0) → caprolactam (105-60-2,9012-16-2) + poly(6-aminocaproamide-co-6-aminocaproic acid) + 6-aminocaproic amide (373-04-6) + methyl 6-aminohexanoate hydrochloride (2780-89-4) + 6-aminohexanoic acid (60-32-2,93208-38-9)

Guidance literature:

methyl 6-oxohexanoate; With ammonia; In methanol; water; at 35 ℃; for 0.00416667h; under 22502.3 Torr;

With hydrogen; 5 % ruthenium on Al2O3; In methanol; water; at 120 ℃; for 22h; under 22502.3 Torr;

Reference yield: 99.0%

caprolactam; 6-aminocaproic acid; 6-aminocaproic amide; nylon-6-oligomers; water; mixture of → caprolactam (105-60-2,9012-16-2) + pentamide (626-97-1) + 5-hexenoic acid (1577-22-6) + hexanoic acid (142-62-1) + valeric acid (109-52-4)

Guidance literature:

at 300 ℃; for 5h; under 9000.9 Torr;

upstream raw materials:

N-Bromosuccinimide

cyclohexanone-oxime

Adipic acid

6-Hydroxyhexanoic acid

Downstream raw materials:

hexahydro-1-(2'-cyanoethyl)-2H-azepin-2-one

1-(2-Hydroxy-2-phenylethyl)perhydro-2-azepinon

1-methyl-2-azepanone

6-phthalimidohexanoic acid

Refernces

The development of a convergent and efficient enantioselective synthesis of the bengamides via a common polyol intermediate

10.1002/hlca.200290026

The research focuses on the development of an efficient and convergent enantioselective synthesis of the bengamides, a family of antitumor agents derived from a common polyol thioester intermediate. The study involves consecutive aldol condensations to construct the protected polyol thioester side chain, which is then coupled to the bengamides. A novel chiral-phase-transfer-catalyzed enantioselective alkylation step is employed to synthesize the caprolactams necessary for more complex bengamide family members. The research utilizes various reactants, including polyol acids, chiral auxiliaries, and different protecting groups, and employs a range of analytical techniques such as NMR, IR, and mass spectrometry to monitor the progress and confirm the structures of the synthesized compounds. The experiments are designed to optimize the synthesis route, improve yields, and ensure the enantiomeric purity of the final products, which are crucial for their potential as therapeutic agents against drug-resistant solid tumors.