Pentamethylendiamin

PDA · CADAVERINE · Pentane-1,5-diamine · 1,5-PENTANEDIAMINE · Cadaverin · PENTAMETHYLENEDIAMINE · 1,4-Pentanediamine

Identifikatoren & physikalische Daten

CAS No.	462-94-2
Summenformel	C5H14N2
Durchschnittliche Molmasse	102,18 g/mol
Monoisotopische Masse	102,11569846 g/mol
SMILES	NCCCCCN
InChIKey	VHRGRCVQAFMJIZ-UHFFFAOYSA-N
PubChem CID	273
ChEMBL	CHEMBL119296
ChEBI	CHEBI:18127
EC No.	207-329-0
DTXSID	DTXSID5075448
Lokaler Name	Pentamethylendiamin

Chemische & physikalische Eigenschaften

XLogP	-0,6
Polarare Oberfläche (TPSA)	52
H-Brücken-Donoren	2
H-Brücken-Akzeptoren	2
Frei drehbare Bindungen	4
Schwere Atome	7
Formalladung	0
Komplexität	25
pH	Strong base
Geruch	Characeteristic odor... partially responsible for the distinctive smell of urine and semen
Dichte	0.873 g/cu cm at 25 °C0.873 g/mL at 25 °C(lit.)
Color/Form	Syrupy, colorless liquidThick fuming liquid
Löslichkeit	Soluble in water, ethanolslightly soluble in ethyl ether1 M HCl: soluble0.5g/10 mL, clear, colorless
Flammpunkt	62 °C (144 °F) - closed cup145 °F
Siedepunkt	179 °C178-180 °C(lit.)
Decomposition	When heated to decomposition it emits highly toxic fumes of /nitroxides/.
Schmelzpunkt	11.83 °C9 °C
Dampfdruck	1.01 [mmHg]1.29-17hPa at 20-25℃
Brechungsindex	Index of refraction = 1.463 at 20 °C/Dn20/D 1.458(lit.)
Physical Description	CBIColorless syrupy liquid that fumes in airmp = 9 deg C[Merck Index] Colorless hygroscopic liquid with an amine-like odor[Alfa Aesar MSDS]
Aggregatzustand	Liquid
pKa (Säurekonstante)	10.05(at 25℃)
Farbe	Clear colorless to yellow
Geruch	characteristic odor
Merck	14,1609
BRN	1697256
Stabilität	Stable. Incompatible with acid chlorides, acids, acid anhydrides, strong oxidizing agents, carbon dioxide.
InChI	1S/C5H14N2/c6-4-2-1-3-5-7/h1-7H2
InChIKey	VHRGRCVQAFMJIZ-UHFFFAOYSA-N
SMILES	NCCCCCN
LogP (Verteilungskoeffizient)	-0.3--0.15 at 21℃
CAS Datenbank	462-94-2(CAS DataBase Reference)
NIST chemische Informationen	1,5-Diaminopentane(462-94-2)
EPA chemische Informationen	Cadaverine (462-94-2)

Sicherheit & Vorschriften

GHS-Einstufung	DangerH302+H312 (64.2%): Harmful if swallowed or in contact with skin [Warning Acute toxicity, oralacute toxicity, dermal]H302 (68.5%): Harmful if swallowed [Warning Acute toxicity, oral]H312 (71%): Harmful in contact with skin [Warning Acute toxicity, dermal]H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]H318 (70.4%): Causes serious eye damage [Danger Serious eye damage/eye irritation]P260, P264, P264+P265, P270, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P362+P364, P363, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 162 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Regulatorische Informationen	Chemical: 1,5-Pentanediamine1,5-Pentanediamine is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,5-Pentanediamine are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.Status: Active Update: 02-07-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/16098Status: Active Update: 18-02-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/277541,5-Pentanediamine: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Weitere Sicherheitsinformationen	Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Brandpotenzial	Combustible liquid
Gefahrenübersicht	A strong base that attracts carbon dioxideA skin irritant and possible sensitizer[Merck Index] Causes burns[HSDB] Causes burnsInhalation may cause corrosive injuries to upper respiratory tract and lungs[Alfa Aesar MSDS] Search for (462-94-2[EC/RN Number]) AND (sensitizer OR sensitization OR allergic OR dermatitis): no papers confirming skin sensitization[PubMed] See 1,6-Diaminohexane.
NFPA Hazard Classification	3 - Materials that, under emergency conditions, can cause serious or permanent injury.2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.0 - Materials that in themselves are normally stable, even under fire conditions.
Toxic Combustion Products	Hazardous decomposition products formed under fire conditions - Carbon oxides, nitrogen oxides (NOx)
Hazard Classes and Categories	Acute Tox. 4 (68.5%)Acute Tox. 4 (71%)Skin Corr. 1B (100%)Eye Dam. 1 (70.4%)
Skin, Eye, and Respiratory Irritations	An irritant ...
Hazardous Reactivities and Incompatibilities	Materials to avoid Acid chlorides, Acid anhydrides, acids, Strong oxidizing agents, Carbon dioxide (CO2)
Brandbekämpfungsverfahren	Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self contained breathing apparatus for fire fighting if necessary.
Lagerbedingungen	Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Store under inert gas.
Reinigungsverfahren	Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed containers for disposal. Do not let product enter drains.
Entsorgungsverfahren	This combustible material may be burned in a chemical incinerator equipped with an afterburner and scrubber. Observe all federal, state, and local environmental regulations. Contact a licensed professional waste disposal service to dispose of this material. Contaminated packaging: dispose of as unused product.
Preventive Measures	Avoid inhalation of vapour or mist. Keep away from sources of ignition - No smoking. Take measures to prevent the build up of electrostatic charge.SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.
Personal Protective Equipment (PPE)	Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU). Hand protection: Handle with gloves. Eye protection: Safety glasses Skin and body protection: Choose body protection according to the amount and concentration of the dangerous substance at the work place.Safety glasses, good ventilation, gloves
Wechselwirkungen	Histamine poisoning can result from the ingestion of food containing unusually high levels of histamine. ... Histamine poisoning is characterized by a short incubation period, a short duration, and symptoms resembling those associated with allergic reactions. The evidence supporting the role of histamine as the causative agent is compelling. ... Histamine ingested with spoiled fish appears to be much more toxic than histamine ingested in an aqueous solution. The presence of potentiators of histamine toxicity in the spoiled fish may account for this difference in toxicity. Several potentiators including other putrefactive amines such as putrescine and cadaverine have been identified. Pharmacologic potentiators may also existaminoguanidine and isoniazid are examples. The mechanism of action of these potentiators appears to be the inhibition of intestinal histamine-metabolizing enzymes. This enzyme inhibition causes a decrease in histamine detoxification in the intestinal mucosa and results in increased intestinal uptake and urinary excretion of unmetabolized histamine.
Ökotoxizitätswerte	LD50Species: Peromyscus maniculatus (Deer Mouse) oral 1600 mg/kg
Umweltverhalten	TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 90(SRC), determined from a structure estimation method(2), indicates that cadaverine is expected to have high mobility in soil(SRC). However, the pKa values of cadaverine are 9.13 and 10.25(3), indicating that this compound will exist almost entirely in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization from moist soil is not expected because the compound exists as a cation and cations do not volatilize. Cadaverine is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.0 mm Hg at 25 °C(SRC), determined from a fragment constant method(5). Biodegradation data in soil were not available(SRC, 2010).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 90(SRC), determined from a structure estimation method(2), indicates that cadaverine is not expected to adsorb to suspended solids and sediment(SRC). The pKa values of 9.13 and 10.25(3) indicate cadaverine will exist almost entirely in the cation form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process. According to a classification scheme(4), an estimated BCF of 3(SRC), from an estimated log Kow of -0.15(5) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data in water were not available(SRC, 2010).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), cadaverine, which has a /an estimated vapor pressure of 1.0 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase cadaverine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 6 hours(SRC), calculated from its rate constant of 6.8X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Cadaverine does not contain chromophores that absorb at wavelengths >290 nm(4), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
Lebensmitteluntersuchungswerte	Cadaverine levels in fresh pork and beef meat were not detected to 0.7 mg/kg and not detected, respectively. Levels in cooked ham and mortadella were not detected to 0.9 mg/kg and not detected to 7.9 mg/kg, respectively. The cadaverine content in ripened meat products ranged from 3.9 to 34.9 mg/kg chorizo and 2.1 to 68.5 mg/kg in salchichon(1).
Unerwünschte Wirkungen	Dermatotoxin - Skin burns.Toxic Pneumonitis - Inflammation of the lungs induced by inhalation of metal fumes or toxic gases and vapors.
Toxizitätsübersicht	IDENTIFICATION AND USE: Cadaverine is a syrupy, colorless liquid with a distinctive odor of urine and semen. It is soluble in water, ethanolslightly soluble in ethyl ether, and miscible in water. It is used in the production of high polymers, as a chemical intermediate, and in biological research. HUMAN EXPOSURE AND TOXICITY: It is a foul-smelling diamine formed by bacterial decarboxylation of lysine. It is poisonous and irritating to the skin. Harmful if ingested, inhaled, or absorbed through the skin. It can cause burns and is very destructive of mucous membranes. Occupational exposure to cadaverine may occur through inhalation and dermal contact with this compound at workplaces where it is produced or used. Monitoring data indicate that the general population may be exposed to cadaverine by ingestion of certain meats. ANIMAL STUDIES: In In rats, cadaverine had a low oral toxicity. Cadaverine caused a dose-related decrease in blood pressure after intravenous administration in rats. The subacute toxicity of this chemical was examined in rats. Cadaverine was administered in the diet to groups of 10 male and 10 female rats. Adverse effects were observed in the high dose group and decreased body weights associated with diminished food intake were observed. Slight increases in packed cell volume, hemoglobin concentration, and thrombocytes occurred with chemical exposure.
Plant Concentrations	Cadaverine was detected, not quantified in unspecified freshwater and marine algae(1).
Effluent Concentrations	Cadaverine was tested for but not detected in gasoline nor diesel exhaust(1).
Soil Adsorption/Mobility	Using a structure estimation method based on molecular connectivity indices(1), the Koc of cadaverine can be estimated to be 90(SRC). According to a classification scheme(2), this estimated Koc value suggests that cadaverine is expected to have high mobility in soil. However, the pKa values of cadaverine are 9.13 and 10.25(3), indicating that this compound will exist almost entirely in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).
Natural Pollution Sources	Cadaverine is a ptomaine formed in the decay of animal proteins after death(1). It is also produced in small quantities by living beings and is partially responsible for the distinctive smell of urine and semen(2). It is related to putrescine. Both are produced by the breakdown of amino acids in living and dead organisms(3).
Human Toxicity Excerpts	/SIGNS AND SYMPTOMS/ Cadaverine ... a foul-smelling diamine formed by bacterial decarboxylation of lysine. It is poisonous and irritating to the skin./SIGNS AND SYMPTOMS/ Stench! Harmful if ingested, inhaled, or absorbed through the skin. Corrosive - causes burns. Very destructive of mucous membranes.
Artificial Pollution Sources	Cadaverine's production and use as a chemical intermediate and in biological research(1) may result in its release to the environment through various waste streams(SRC).
F	10
Wassergefährdungsklasse (WGK)	3
TSCA-Inventar-Status	TSCA listed
UN-Transportnummer	UN 2735 8/PG 3
Zollcode	29212900
RTECS-Nr.	SA0200000
R-Sätze (R)	34-36/37
Toxizität	dni-mus:ast 10 mmol/L AMOKAG 33,149,79
Gefahrensymbole	C
Sicherheitshinweise (S)	26-36/37/39-45-25-27
Gefahrenklasse	8Eye Dam. 1Skin Corr. 1B
Verpackungsgruppe	III
Lagerklasse	8A - Combustible corrosive hazardous materials
Gefahrstoffdaten	462-94-2(Hazardous Substances Data)

Anwendungen & Verwendung

Verwenden

1,5-Diaminopentane is mainly used in organic synthesis.