462-94-2

Basic information

• Product Name: 1,5-Diaminopentane
• Synonyms: Pentane-1,5-diamine;5,5'-PENTANEDIAMINE;1,5-DIAMINOPENTANE;1,5-PENTANEDIAMINE;1,5-PENTAMETHYLENEDIAMINE;CADAVERINE;PENTAMETHYLENEDIAMINE;RARECHEM AL BW 0076
• CAS NO: 462-94-2
• Molecular Formula: C₅H₁₄N₂
• Molecular Weight: 102.18
• EINECS: 207-329-0
• Product Categories: Amines;alpha,omega-Alkanediamines;alpha,omega-Bifunctional Alkanes;Monofunctional & alpha,omega-Bifunctional Alkanes;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Polyamines
• Mol File: 462-94-2.mol

Chemical Properties

• Melting Point: 9 °C
• Boiling Point: 178-180 °C(lit.)
• Flash Point: 145 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 0.873 g/mL at 25 °C(lit.)
• Vapor Pressure: 4.93E-08mmHg at 25°C
• Refractive Index: n20/D 1.458(lit.)
• Solubility: 1 M HCl: soluble0.5g/10 mL, clear, colorless
• PKA: 10.05(at 25℃)
• Water Solubility: soluble
• Sensitive: Air Sensitive & Hygroscopic
• Stability: Stable. Incompatible with acid chlorides, acids, acid anhydrides, strong oxidizing agents, carbon dioxide.
• Merck: 14,1609
• BRN: 1697256
• CAS DataBase Reference: 1,5-Diaminopentane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-Diaminopentane(462-94-2)
• EPA Substance Registry System: 1,5-Diaminopentane(462-94-2)

Safety Data

• Hazard Codes: C
• Statements: 34-36/37
• Safety Statements: 26-36/37/39-45-25-27
• RIDADR: UN 2735 8/PG 3
• WGK Germany: 3
• RTECS: SA0200000
• F: 10
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 462-94-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1,5-Diaminopentane is used as a building block in organic synthesis for the production of various chemical compounds and materials. Its versatile structure allows it to be incorporated into a wide range of organic molecules, making it a valuable intermediate in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Hetarylation Reactions:
In the field of heterocyclic chemistry, 1,5-Diaminopentane is used as a diamine in hetarylation reactions with halopyridines (2-bromo, 2-iodo, and 3-iodo-pyridines). These reactions, catalyzed by CuI-2-isobutyrylcyclohexanone, lead to the formation of N,N′-dipyridinyl diamine derivatives. These derivatives are important in the development of new heterocyclic compounds with potential applications in various fields, such as pharmaceuticals and materials science.
Used in the Synthesis of Poly-imidazolium Polymers:
1,5-Diaminopentane is also used in the synthesis of poly-imidazolium polymers, which exhibit high thermal stability. This is achieved through a modified Debus-Radziszewski reaction, where 1,5-Diaminopentane reacts with acetic acid, pyruvaldehyde, and formaldehyde. The resulting polymers have potential applications in various industries, including aerospace, automotive, and electronics, due to their excellent thermal and mechanical properties.

Flammability and Explosibility

Notclassified

Safety Profile

Poison by intravenous, rectal, and subcutaneous routes. Moderately toxic by skin contact. An irritant, sensitizer, and allergen. Mutagenic data. When heated to decomposition it emits highly toxic fumes of NOx.

Purification Methods

Purify the base by distillation, after standing over KOH pellets (at room temperature, i.e. liquid form). Its dihydrochloride has m 275o (sublimes in a vacuum), and its tetraphenyl boronate has m 164o. [Schwarzenbach et al. Helv Chim Acta 35 2333 1952, Beilstein 4 IV 1310.]

InChI:InChI=1/C4H6O6.C3H10N2/c5-1(3(7)8)2(6)4(9)10;4-2-1-3-5/h1-2,5-6H,(H,7,8)(H,9,10);1-5H2

Upstream product

• 776-75-0 N-benzoylpiperidine 
• 5692-29-5 N-benzoyl-1,5-diaminopentane 
• 982-50-3 1,5-(N,N-diphthalimide)pentane 
• 7647-01-0 hydrogenchloride 
• 67-56-1 methanol 
• 544-13-8 Glutaronitrile 
• 64-17-5 ethanol 
• 108-93-0 cyclohexanol 
• 71-36-3 butan-1-ol 
• 111-29-5 1 ,5-pentanediol 
• 3350-74-1 5-oxopentanenitrile 
• 504-29-0 2-aminopyridine 
• 84211-46-1 Desferri-ferrioxamin H 
• 2317-69-3 Di-trifluoracetyl-diaminopentan-(1,5) 

Downstream Products

• 18431-52-2 1-amino-5-guanidinopentane 
• 5070-04-2 1,5-Diguanidino-pentan 
• 110-89-4 piperidine 
• 505-18-0 2,3,4,5-tetrahydropyridine 
• 111-29-5 1 ,5-pentanediol 
• 18807-70-0 N,N'-pentane-1,5-diyl-bis-carbamic acid dibenzyl ester 
• 32343-73-0 N-(5-aminopentyl)acetamide 
• 34237-69-9 N,N'-di-(tert-butoxycarbonyl)-1,5-diaminopentane 
• 51644-96-3 5-tert-butoxycarbonylamino-1-aminopentane 
• 77835-31-5 N-(tert-butoxycarbonyl)-1,5-diaminopentane hydrochloride 
• 104807-16-1 {5-[5-(6-Benzyloxycarbonylamino-hexanoylamino)-pentylcarbamoyl]-pentyl}-carbamic acid benzyl ester 
• 759410-91-8 N-<3-<(phenylmethyl)thio>propyl>-1,5-pentanediamine 
• 100-02-7 4-nitro-phenol 
• 76218-84-3 N,N'-bis(2,3-dihydroxybenzoyl)-1,4-diaminopentane 

Relevant articles and documents

The use of l-lysine decarboxylase as a means to separate amino acids by electrodialysis

Amino acids (AA's) are interesting materials as feedstocks for the chemical industry as they contain chemical functionalities similar to conventional petrochemicals. This offers the possibility to circumvent process steps, energy and reagents. AA's can be obtained by the hydrolysis of potentially inexpensive voluminous protein streams derived from biofuel production. However, isolation of the preferred AA is required in order to carry out further transformation into the desired product. Theoretically separation may be achieved using electrodialysis. To increase efficiency, specific modification to a product of industrial interest and removes charged groups of AA's with similar isoelectric points is required. Here, the reaction of l-lysine decarboxylase (LDC) was studied as a means to specifically convert l-lysine (Lys) to 1,5-pentanediamine (PDA) in the presence of l-arginine (Arg) to produce products with different charge thus allowing isolation of products by electrodialysis. Immobilization of LDC in calcium alginate enhanced the operational stability and conversion in mixtures of amino acids was highly specific. At 30 °C the presence of Arg had little effect on the activity of the enzyme although inhibition by the product PDA could be observed. Volumetric productivity was calculated and raw material and transformation costs were estimated for a potential process using a mixture of Arg and Lys. The Royal Society of Chemistry.

Stoffwechselprodukte von Mikroorganismen. 216 Mitteilung. Isolierung, Strukturaufklaerung und Synthese von Ferrioxamin H

The structure of ferrioxamine H, a minor component of the sideramine complex of actinomycetes, was determined by spectroscopic investigations, degradation and synthesis.Ferrioxamine H is the Fe(III)-complex of 11,22-dihydroxy-4,12,15,23-tetraoxo-5,11,16,22-tetraazatetracosanoic acid (2).

Advances in bio-nylon 5X: Discovery of new lysine decarboxylases for the high-level production of cadaverine

Cadaverine (1,5-pentanediamine) is the most important precursor for nylon PA5X, which has an extremely competitive market due to the high consumption of engineered plastics and fibers. The key enzyme lysine decarboxylase is in desperate need for industrial bio-based cadaverine production. In this study, new lysine decarboxylases have been mined by peptide pattern recognition for the high-level production of cadaverine. The predicted enzymes were expressed in E. coli and analyzed as whole-cell biocatalysts. Two outstanding recombinant enzymes from Edwardsiella tarda and Aeromonas sp. (LdcEt and LdcAer, respectively), were further purified and characterized. The optimal pH and temperature for LdcEt and LdcAer were pH 7, 55 °C and pH 6, 50 °C, respectively. These two enzymes were stable over the pH range of 5-7 during 24 h incubation. Both of them still had activity after being incubated at pH 8. LdcEt and LdcAer also have good thermostability with a half-life of 14.5 h and 20.3 h at 60 °C, respectively. The kinetic analysis showed that they have high catalytic efficiency as the kcat/Km (LdcEt: 243.28 s-1 mM-1; LdcAer: 266.86 s-1 mM-1) was the highest when compared for all the related studies. The whole cell conversion by LdcEt with 0.1% (v/v) Triton X-100 can convert 100% 2 M l-lysine HCl to cadaverine in 2 h and the cadaverine productivity was high up to 103.47 ± 4.37 g L-1 h-1. The in vitro studies further found that unpurified cell-lysates of LdcEt had relatively higher activity compared to the whole cell conversion. Meanwhile, 0.4 mg mL-1 purified LdcEt and LdcAer can efficiently produce 165.96 ± 1.41 g L-1 and 155.84 ± 4.63 g L-1 cadaverine only in 0.5 h, respectively. The high specific activity, pH, thermo-stability, and catalytic efficiency in vivo and in vitro, combined with simultaneous cell treatment with Triton X-100 and the bioconversion process, provide LdcEt with great potential in the economic and efficient production of cadaverine at the industrial scale. This journal is

Engineering a cleavable disulfide bond into a natural product siderophore using precursor-directed biosynthesis

An analogue of the bacterial siderophore desferrioxamine B (DFOB) containing a disulfide motif in the backbone was produced from Streptomyces pilosus cultures supplemented with cystamine. Cystamine competed against native 1,5-diaminopentane during assembly. DFOB-(SS)1[001] and its complexes with Fe(iii) or Ga(iii) were cleaved upon incubation with dithiothreitol. Compounds such as DFOB-(SS)1[001] and its thiol-containing cleavage products could expand antibiotic strategies and Au-S-based nanotechnologies.

Supramolecular Assays for Mapping Enzyme Activity by Displacement-Triggered Change in Hyperpolarized 129Xe Magnetization Transfer NMR Spectroscopy

Reversibly bound Xe is a sensitive NMR and MRI reporter with its resonance frequency being influenced by the chemical environment of the host. Molecular imaging of enzyme activity presents a promising approach for disease identification, but current Xe biosensing concepts are limited since substrate conversion typically has little impact on the chemical shift of Xe inside tailored cavities. Herein, we exploit the ability of the product of the enzymatic reaction to bind itself to the macrocyclic hosts CB6 and CB7 and thereby displace Xe. We demonstrate the suitability of this method to map areas of enzyme activity through changes in magnetization transfer with hyperpolarized Xe under different saturation scenarios. The supramolecular recognition properties of cucurbiturils are exploited in a modified signal-transfer approach in Xe NMR spectroscopy. Magnetic resonance imaging of enzymatic reactions was possible in this way by displacement of hyperpolarized 129Xe.

The Effect of Visible Light on the Catalytic Activity of PLP-Dependent Enzymes

Pyridoxal 5’-phosphate (PLP)-dependent enzymes are a versatile class of biocatalysts and feature a variety of industrial applications. However, PLP is light sensitive and can cause inactivation of enzymes in certain light conditions. As most of the PLP-dependent enzymes are usually not handled in dark conditions, we evaluated the effect of visible light on the activity of PLP-dependent enzymes during production as well as transformation. We tested four amine transaminases, from Chromobacterium violaceum, Bacillus megaterium, Vibrio fluvialis and a variant from Arthrobacter species as well as two lysine decarboxylases, from Selenomonas ruminantium and the LDCc from Escherichia coli. It appeared that five of these six enzymes suffered from a significant decrease in activity by up to 90 % when handled in laboratory light conditions. Surprisingly, only the amine transaminase variant from Arthrobacter species appeared to be unaffected by light exposure and even showed an activation to 150 % relative activity over the course of 6 h regardless of the light conditions.

Preparation method of pentamethylene diamine

The invention provides a preparation method of pentamethylene diamine. The method comprises the following steps: a) reacting acrylonitrile with acetaldehyde under the catalytic action of N,N-dihydroxyethyl-1,4-pentamethylene diamine to obtain 5-formyl valeronitrile; and b) carrying out one-step reaction on the product obtained in the step a) and mixed gas of ammonia gas and hydrogen under the action of a catalyst and an auxiliary agent to obtain pentamethylene diamine. Compared with the traditional method for synthesizing pentamethylene diamine by using lysine as a raw material and a biological method, the method has the advantages of simple steps and low cost, and is suitable for large-scale production of pentamethylene diamine. The use of the catalyst N,N-dihydroxyethyl-1,4-pentamethylene diamine can inhibit the self-polymerization of acetaldehyde and acrylonitrile, thereby greatly enhancing the selectivity of the target intermediate.

MODIFIED MEMBRANE PERMEABILITY

Provided are microorganisms genetically modified to overexpress porin polypeptides to enhance the production of lysine and lysine derivatives by the microorganism. Also provided are methods of generating such microorganism, and methods of producing lysine and lysine derivatives using the genetically modified microorganisms.

Organocatalytic Decarboxylation of Amino Acids as a Route to Bio-based Amines and Amides

Amino acids obtained by fermentation or recovered from protein waste hydrolysates represent an excellent renewable resource for the production of bio-based chemicals. In an attempt to recycle both carbon and nitrogen, we report here on a chemocatalytic, metal-free approach for decarboxylation of amino acids, thereby providing a direct access to primary amines. In the presence of a carbonyl compound the amino acid is temporarily trapped into a Schiff base, from which the elimination of CO2 may proceed more easily. After evaluating different types of aldehydes and ketones on their activity at low catalyst loadings (≤5 mol%), isophorone was identified as powerful organocatalyst under mild conditions. After optimisation many amino acids with a neutral side chain were converted in 28–99 % yield in 2-propanol at 150 °C. When the reaction is performed in DMF, the amine is susceptible to N-formylation. This consecutive reaction is catalysed by the acidity of the amino acid reactant itself. In this way, many amino acids were efficiently transformed to the corresponding formamides in a one-pot catalytic system.

A new kind of acetylcholine esterase inhibitors and its preparation method and application (by machine translation)

The present invention provides a novel acetyl choline esterase inhibitor and its preparation method and application, in particular, the invention discloses a formula A shown with double AChE binding site of substituted acridine compound, and its preparation method and as acetylcholinesterase inhibitors. The preparation of the novel compounds of this invention demonstrate good inhibit acetylcholine esterase role, can be used as a preparation for treating and preventing HAMER (AD) application value. (by machine translation)