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Piperidine

Piperidine Chemical Properties
Melting point -11 °C
Boiling point 106 °C(lit.)
density 0.930 g/mL at 20 °C
vapor density 3 (vs air)
vapor pressure 23 mm Hg ( 20 °C)
refractive index n20/D 1.452(lit.)
FEMA 2908 | PIPERIDINE
Fp 16 °C(lit.)
storage temp. Store in dark!
solubility miscible in water and alcohol; soluble in ether, acetone, benzene and chloroform maximum allowable concentration: not established; more toxic, irritating and volatile than pyridine (Reinhardt and Brittelli 1981).
pka11.123(at 25℃)
PH12.6 (100g/l, H2O, 20°C)
explosive limit1.5-10.3%(V)
Water Solubility Miscible
Sensitive Air Sensitive
Merck 14,7468
BRN 102438
Stability:Stable. Highly flammable. Incompatible with strong oxidizing agents, strong acids, organic acids, water. Vapours may flow along surfaces to a distant source of ignition.
CAS DataBase Reference110-89-4(CAS DataBase Reference)
NIST Chemistry ReferencePiperidine(110-89-4)
EPA Substance Registry SystemPiperidine(110-89-4)
Safety Information
Hazard Codes T,F
Risk Statements 61-10-20/21-34-23/24-11-52-24-20/22
Safety Statements 53-16-26-36/37/39-45-27
RIDADR UN 3286 3/PG 2
WGK Germany 3
RTECS TM3500000
3-34
Autoignition Temperature320 °C
TSCA Yes
HazardClass 8
PackingGroup I
HS Code 29333210
Hazardous Substances Data110-89-4(Hazardous Substances Data)
ToxicityLD50 orally in rats: 0.52 ml/kg (Smyth)
MSDS Information
ProviderLanguage
SigmaAldrich English
ALFA English
Piperidine Usage And Synthesis
Chemical PropertiesClear or slightly yellow liquid
Chemical PropertiesPiperidine is a clear, colorless liquid. Pepper, ammonia or amine odor.
Chemical PropertiesPiperidine is a strong base (pKb = 2.88) that reacts vigorously with oxidizing materials, is easily ignited, and forms explosive vapor concentrations at room temperature. When heated to decomposition it gives off toxic fumes of NOx (Sax 1984). It behaves like an aliphatic secondary amine and can form complexes with salts of heavy metals (HSDB 1988).
OccurrencePiperidine occurs at low levels in a variety of food products (Neurath et al 1977), including baked ham (0.2 p.p.m.), milk (0.11 p.p.m.) coffee (1 p.p.m. dry) (Singer and Lijinsky 1976) and canned fish (Tanikawa and Motohiro 1960). It is also found in black pepper (Windholz 1983), hemp (Obata and Ishikawa 1960), hemlock (Cromwell 1956) and tobacco (Furia and Bellanca 1975). Piperidine is a natural constituent of skin (Sax and Lewis 1987), human urine (Von Euler 1944), brain (Honegger and Honegger 1960) and cerebrospinal fluid (Perry et al 1964). Humans excrete about 3-20 mg/d in the urine (Reinhardt and Britelli 1981).
UsesFits Applied Biosystems 431 and 433A peptide synthesizers.
UsesPiperidine is an organic heterocyclic amine widely used as building block and reagent in the synthesis of organic compounds including pharmaceuticals.
DefinitionChEBI: An azacycloalkane that is cyclohexane in which one of the carbons is replaced by a nitrogen. It is a metabolite of cadaverine, a polyamine found in the human intestine.
Production MethodsPiperidine is usually prepared by the electrolytic reduction of pyridine. It may also be obtained by heating piperidine with alcoholic KOH or by the cyclization of 1,5-diaminopentane hydrochloride (Windholz 1983). U.S. production in 1983 was approximately 606,000 pounds (HSDB 1988). Commercial piperidine is supplied in two grades, 95 and 98 percent pure (Sax and Lewis 1987).
Brand nameCypentil (Abbott).
General DescriptionA clear colorless liquid with a pepper-like odor. Less dense than water, but miscible in water. Will float on water. Flash point 37°F. Melting point -15.8°F (-9°C). Boiling point 222.8°F (106°C). May severely irritate skin and eyes. May be toxic by ingestion and inhalation. Vapors heavier than air. Used to make rubber and as a solvent.
Air & Water ReactionsHighly flammable. Miscible in water.
Reactivity Profile1-Oxa-4-azacyclohexane neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.
Health HazardStrong local irritant and may cause permanent injury after short exposure to small amounts. Ingestion may involve both irreversible and reversible changes. 30 to 60 mg/kg may cause symptoms in humans.
Health HazardAn irritation threshold of 26 p.p.m. has been reported from studies on human volunteers (Bazarova and Migukina 1975). Levels of 2 to 5 p.p.m. in air have been recorded during the transfer of piperidine from drums in a semi-closed system. At this level, the vapors were intolerable but no irritation was observed (ANON 1982). In an accidental case of skin exposure, third-degree burns developed after only 3 min of skin contact (Linch 1965). Piperidine has a pronounced emetic effect in humans. When administered to schizophrenic patients at doses of 1 to 6 g/d, it was shown to cause nausea and a subjective sense of well being (Giacobini 1976; Tasher et al 1960). The primary, but low-level, means of human exposure, however, is from the natural piperidine content of foods (HSDB 1988).
Fire Hazard1-Oxa-4-azacyclohexane evolves explosive concentrations of vapor at normal room temperatures. When heated to decomposition, 1-Oxa-4-azacyclohexane emits highly toxic fumes of nitrogen oxides. Dangerous, when exposed to heat, flame, or oxidizers. Avoid 1-Perchloryl1-Oxa-4-azacyclohexane and oxidizing materials. 1-Oxa-4-azacyclohexane is a reactive compound and forms complexes with the salts of heavy metals. 1-Oxa-4-azacyclohexane evolves explosive concentrations of vapor at normal room temperatures. Keep away from igniting sources and heat.
Industrial usesPiperidine is used as a solvent, a curing agent for rubber and epoxy resins, a catalyst in silicone esters, an intermediate in organic synthesis and as a complexing agent (HSDB 1988; Reinhardt and Britelli 1981). It is a trace constituent in oils and fuels (Sax and Lewis 1987). It is used in the manufacture of local anesthetics, analgesics and other pharmaceuticals, and also for wetting agents and germicides (Gehring 1983). It is also used as a flavor additive in soups, meats, condiments, baked goods, candy and non-alcoholic beverages at 0.05-5.0 p.p.m. (Furia and Bellanca 1975).
Safety ProfilePoison by ingestion, skin contact, and intraperitoneal routes. Moderately toxic by subcutaneous route. Mildly toxic by inhalation. An experimental teratogen. Experimental reproductive effects by inhalation. A skin irritant. Mutation data reported. A very dangerous fire hazard when exposed to heat, flame, or oxidizers. Can react vigorously with oxidzing materials. To fight fire, use alcohol foam, CO2, dry chemical. Explodes on contact with 1- perchloryl-piperidme, dqanofurazan, N- nitrosoacetadde. When heated to decomposition it emits highly toxic fumes of NOx. Used in agriculture and pharmaceuticals, and as an intermediate for rubber accelerators. Used in production of drugs of abuse.
Potential ExposurePiperidine is used in agriculture and pharmaceuticals; intermediate for rubber accelerators; as a solvent; as a curing agent for rubber and epoxy resins; catalyst for condensation reactions; as an ingredient in oils and fuels; complexing agent; manufacture of local anesthetics; in analgesics; pharmaceuticals, wetting agents; and germicides; synthetic flavoring. Not registered as a pesticide in the Unied States.
First aidIf this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit. Medical observation is recommended for 2448 hours after breathing overexposure, as pulmonary edema may be delayed. As first aid for pulmonary edema, a doctor or authorized paramedic may consider administering a drug or other inhalation therapy.
MetabolismPiperidine is readily absorbed through the gastrointestinal tract, skin and lungs (HSDB 1988). In hens, 35 to 70% of an injected dose is rapidly excreted unchanged in the urine (Williams 1959; Sperber 1949). Rabbits also excrete piperidine unchanged (Hildebrandt 1900). When injected intraventricularly into rats, piperidine disappeared exponentially with a half-life of 20 min (Meek 1973). In a more recent study, Okano et al (1978) found that in rats most of an i.p. dose of [3H]-piperidine was excreted unchanged. Two major metabolites were identified as 3- and 4-hydroxypiperidine. Both compounds were also found in untreated animals and thus are probably metabolites of piperidine of exogenous or endogenous origin. These metabolites represent a detoxification mechanism, since they lack the potent pharmacological activities of the parent compound. Two unidentified metabolites were assumed to be conjugates. In a much earlier study, Novello et al (1926) claimed that piperidine was excreted as the ethereal sulfate. Metabolic studies of analgesics and anesthetics containing the piperidine ring have demonstrated the occurrence of N-hydroxylation, formation of a 6-oxo-derivative, and C-oxidative ring cleavage (Oelschlager and Al Shaik 1985). N-nitrosopiperidine has been synthesized from piperidine and sodium nitrite in the gastric contents,R.L. Reed isolated stomach and isolated small intestine of rats (Alam et al 1971; Epstein 1972).
ShippingUN2401 Piperidine, Hazard Class: 8; Labels: 8-Corrosive material, 3-Flammable liquid.
Purification MethodsDry piperidine with BaO, KOH, CaH2, or sodium, and fractionally distil (optionally from sodium, CaH2, or P2O5). Purify from pyridine by zone melting. [Beilstein 22 H 6, 22
IncompatibilitiesPiperidine is a highly flammable liquid. Vapor may form explosive mixture with air (at room temperature). A medium-strong base. Reacts violently with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Piperidine neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.
Piperidine Preparation Products And Raw materials
Preparation Products3-CYANO-7-METHOXYCOUMARIN-->3-(4-AMINO-PHENYL)-CHROMEN-2-ONE-->7-HYDROXY-2-OXO-2H-CHROMENE-3-CARBOXYLIC ACID METHYL ESTER-->2-Chloro-6-methyl-3-pyridinecarbonitrile-->6-BROMO-3-BUTYRYL-2H-CHROMEN-2-ONE-->3-(3-AMINOPHENYL)-2H-CHROMEN-2-ONE-->5-METHYL-4-ISOXAZOLESULFONYL CHLORIDE-->2-Amino-5-nitropyrimidine-->Minoxidil-->Bis(pentamethylene)thiuram tetrasulfide -->CLOPERASTINE-->3-ACETAMIDOCOUMARIN-->5,6,7,8-TETRAHYDRO-3H-BENZO[4,5]THIENO[2,3-D]-PYRIMIDIN-4-ONE-->RARECHEM AL BI 0736-->3-PYRIDIN-2-YL-PROPIONIC ACID H2SO4-->6-CHLORO-2-OXO-2H-CHROMENE-3-CARBOXYLIC ACID-->4-Hydroxy-3,5-dimethoxycinnamic acid-->3-ACETYL-7-HYDROXY-2H-CHROMEN-2-ONE-->trans-2,4,5-Trimethoxycinnamic acid-->Difenidol hydrochloride-->5-BROMO-2-FLUOROCINNAMIC ACID-->4-ETHOXYCINNAMIC ACID-->1-PIPERIDINEPENTANOL-->1,2,3,5-TETRAHYDRO-8-THIA-5,7-DIAZA-CYCLOPENTA[A]INDENE-4-ONE-->7-HYDROXY-2-OXO-2H-CHROMENE-3-CARBOXYLIC ACID METHYL ESTER-->3-(TRIFLUOROMETHOXY)CINNAMIC ACID-->4-Fluorocinnamic acid-->3,5-DIMETHOXYCINNAMIC ACID-->3,4-(Methylenedioxy)cinnamic acid-->2-AMINO-4-ETHYL-5-METHYL-THIOPHENE-3-CARBOXYLIC ACID METHYL ESTER-->2-AMINO-5,6-DIHYDRO-4H-CYCLOPENTA[B]THIOPHENE-3-CARBOXYLIC ACID ETHYL ESTER-->3,5-Dimethoxy-4-hydroxybenzaldehyde-->N-(2-Aminoethyl)piperidine-->NAPHTHALENE-2,3-DICARBOXALDEHYDE-->2-AMINO-6-METHYL-4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE-3-CARBOXAMIDE-->3-(3-METHYL-2-THIENYL)ACRYLIC ACID-->ETHYL 2-AMINO-4,5,6,7-TETRAHYDROBENZO[B]THIOPHENE-3-CARBOXYLATE-->2-AMINO-5,6-DIHYDRO-4H-CYCLOPENTA[B]THIOPHENE-3-CARBOXYLIC ACID METHYL ESTER-->Tolperisone hydrochloride-->Benproperine phosphate
Raw materialsSodium-->Hydrogen-->Piperidine hydrochloride
Tag:Piperidine(110-89-4) Related Product Information
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