Cadaverine

Base Information

• Chemical Name: Cadaverine
• CAS No.: 462-94-2
• Molecular Formula: C5H14N2
• Molecular Weight: 102.18
• Hs Code.: 29212900
• European Community (EC) Number: 207-329-0
• UNII: L90BEN6OLL
• DSSTox Substance ID: DTXSID5075448
• Nikkaji Number: J5.771A
• Wikipedia: Cadaverine
• Wikidata: Q161555
• NCI Thesaurus Code: C95330
• Pharos Ligand ID: XAP9P6FX95CV
• Metabolomics Workbench ID: 38124
• ChEMBL ID: CHEMBL119296
• Mol file: 462-94-2.mol

Synonyms:1,5 Pentanediamine;1,5-Pentanediamine;BioDex 1;Cadaverine;Pentamethylenediamine

Chemical Property of Cadaverine

Chemical Property:

• Appearance/Colour: colourless to light yellow liquid
• Vapor Pressure: 4.93E-08mmHg at 25°C
• Melting Point: 9 °C
• Refractive Index: n20/D 1.458(lit.)
• Boiling Point: 179 °C at 760 mmHg
• PKA: 10.05(at 25℃)
• Flash Point: 76.5 °C
• PSA: 52.04000
• Density: 0.862 g/cm³
• LogP: 1.47470
• Sensitive.: Air Sensitive & Hygroscopic
• Solubility.: 1 M HCl: soluble0.5g/10 mL, clear, colorless
• Water Solubility.: soluble
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 102.115698455
• Heavy Atom Count: 7
• Complexity: 25.3

Purity/Quality:

98% ^*data from raw suppliers

Cadaverine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C
• Statements: 34-36/37
• Safety Statements: 26-36/37/39-45-25-27

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amines, Aliphatic
• Canonical SMILES: C(CCN)CCN
• Uses: 1,5-Diaminopentane is mainly used in organic synthesis. Cadaverine is a diamine that can be used in hetarylation with halopyridines (2-bromo, 2-iodo, and 3-iodo-pyridines) to synthesize N,N′-dipyridinyl diamine derivatives in the presence of CuI-2-isobutyrylcyclohexanone as a catalyst. It can also be used to synthesize a poly-imidazolium polymer with high thermal stability by reacting with acetic acid, pyruvaldehyde and formaldehyde by modified Debus-Radziszewski reaction.

Technology Process of Cadaverine

There total 59 articles about Cadaverine 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: 99.0%

L-Lysine hydrochloride (657-27-2,10098-89-2,26124-78-7) → 1,5-diaminopentane (462-94-2)

Guidance literature:

With hydrogenchloride; pyridoxal 5'-phosphate; at 37 ℃; for 24h; pH=6; Enzymatic reaction;

Reference yield: 96.0%

2,6-diaminocaproic acid (70-54-2,923-27-3,6899-06-5,60103-30-2,60132-27-6,56-87-1,3506-25-0) → 1,5-diaminopentane (462-94-2)

Guidance literature:

With C₂₅H₃₀N₂; cyclohexanol; at 160 ℃; for 2.5h; under 760.051 Torr; Reagent/catalyst;

Reference yield: 96.0%

L-lysine (56-87-1,3506-25-0) → 1,5-diaminopentane (462-94-2)

Guidance literature:

With cyclododecanone; at 200 ℃; for 0.333333h; under 760.051 Torr; Reagent/catalyst; Temperature; Time;

upstream raw materials:

1,5-dibromo-pentane

potassium phtalimide

heptanedioic acid

chloroform

Downstream raw materials:

1,5-Diguanidino-pentan

1,5-bispentane

1,5-bis-(2-bromo-propionylamino)-pentane

N-benzyl-1,5-diaminopentane

Refernces

• 1、 Adapa, Srinivas,Huber, Peter,Keller-Schierlein, Walter. "Stoffwechselprodukte von Mikroorganismen. 216 Mitteilung. Isolierung, Strukturaufklaerung und Synthese von Ferrioxamin H". . p. 1818 - 1824. Retrieved 1982.
• 2、 Richardson-Sanchez, Tomas,Codd, Rachel. "Engineering a cleavable disulfide bond into a natural product siderophore using precursor-directed biosynthesis". . p. 9813 - 9816. Retrieved 2018.
• 3、 Gerlach, Tim,Nugroho, David Limanhadi,Rother, D?rte. "The Effect of Visible Light on the Catalytic Activity of PLP-Dependent Enzymes". . p. 2398 - 2406. Retrieved 2021/04/05.
• 4、 Claes, Laurens,Janssen, Michiel,De Vos, Dirk E.. "Organocatalytic Decarboxylation of Amino Acids as a Route to Bio-based Amines and Amides". . p. 4297 - 4306. Retrieved 2019/08/26.