Piperidine CAS 110-89-4
Introduction：Basic information about Piperidine CAS 110-89-4, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Piperidine Basic information
| Product Name: | Piperidine |
| Synonyms: | PENTAMETHYLENEIMINE;PIP;PIPERIDINE;PIPERIDINE ON RASTA RESIN;PPR;Pentamethylenimin;Pentamethylenimine;perhydroazine |
| CAS: | 110-89-4 |
| MF: | C5H11N |
| MW: | 85.15 |
| EINECS: | 203-813-0 |
| Product Categories: | BasesChemical Synthesis;Organic Bases;Supported Reagents;Supported Synthesis;Synthetic Reagents;Chemistry;Solvents and Mixtures for Peptide Synthesis;Peptide Synthesis;Specialty Synthesis;Other Reagents;Piperidine;Building Blocks;C5 to C7;Chemical Synthesis;Heterocyclic Building Blocks;Piperidines;Amber Glass Bottles;Biotech;Solvent Bottles;Solvent Packaging Options;Solvents;Sure/Seal Bottles;API Intermediate |
| Mol File: | 110-89-4.mol |
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 | n |
| FEMA | 2908 | PIPERIDINE |
| Fp | 16 °C(lit.) |
| storage temp. | Store in dark! |
| solubility | miscible in water and alcohol; soluble in ether, acetone, benzene andchloroformmaximum allowable concentration: not established; more toxic, irritating andvolatile than pyridine (Reinhardt and Brittelli 1981). |
| pka | 11.123(at 25℃) |
| form | liquid |
| color | APHA: ≤50 |
| Odor | at 1.00 % in propylene glycol. heavy sweet floral animal |
| PH | 12.6 (100g/l, H2O, 20°C) |
| explosive limit | 1.5-10.3%(V) |
| Odor Type | animal |
| biological source | synthetic |
| Water Solubility | Miscible |
| Sensitive | Air Sensitive |
| Merck | 14,7468 |
| JECFA Number | 1607 |
| BRN | 102438 |
| Dielectric constant | 5.9（20℃） |
| 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. |
| InChI | 1S/C5H11N/c1-2-4-6-5-3-1/h6H,1-5H2 |
| InChIKey | NQRYJNQNLNOLGT-UHFFFAOYSA-N |
| SMILES | C1CCNCC1 |
| LogP | 0.61 |
| Surface tension | 30.27mN/m at 293.15K |
| CAS DataBase Reference | 110-89-4(CAS DataBase Reference) |
| NIST Chemistry Reference | Piperidine(110-89-4) |
| EPA Substance Registry System | Piperidine (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 |
| F | 3-34 |
| Autoignition Temperature | 320 °C |
| TSCA | TSCA listed |
| HazardClass | 8 |
| PackingGroup | I |
| HS Code | 29333210 |
| Storage Class | 3 - Flammable liquids |
| Hazard Classifications | Acute Tox. 3 Dermal Acute Tox. 3 Inhalation Acute Tox. 4 Oral Eye Dam. 1 Flam. Liq. 2 Skin Corr. 1B |
| Hazardous Substances Data | 110-89-4(Hazardous Substances Data) |
| Toxicity | LD50 orally in rats: 0.52 ml/kg (Smyth) |
| Chemical Properties | Clear or slightly yellow liquid |
| Chemical Properties | Piperidine is a clear, colorless liquid. Pepper, ammonia or amine odor. |
| Chemical Properties | Piperidine is a strong base (pKb = 2.88) that reacts vigorously with oxidizingmaterials, is easily ignited, and forms explosive vapor concentrations at roomtemperature. When heated to decomposition it gives off toxic fumes of NOx (Sax1984). It behaves like an aliphatic secondary amine and can form complexes withsalts of heavy metals (HSDB 1988). |
| Chemical Properties | Piperidine has a heavy, sweet, floral, animal odor and a burning peppery taste. |
| Occurrence | Piperidine 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) (Singerand Lijinsky 1976) and canned fish (Tanikawa and Motohiro 1960). It is alsofound in black pepper (Windholz 1983), hemp (Obata and Ishikawa 1960),hemlock (Cromwell 1956) and tobacco (Furia and Bellanca 1975). Piperidine is anatural 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). |
| Uses | It is used in organic synthesis, especially inthe preparation of many crystalline derivativesof aromatic nitro compounds. |
| Uses | Fits Applied Biosystems 431 and 433A peptide synthesizers. |
| Uses | Piperidine is an organic heterocyclic amine widely used as building block and reagent in the synthesis of organic compounds including pharmaceuticals. |
| Definition | ChEBI: 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 Methods | Piperidine is usually prepared by the electrolytic reduction of pyridine. It may alsobe obtained by heating piperidine with alcoholic KOH or by the cyclization of1,5-diaminopentane hydrochloride (Windholz 1983). U.S. production in 1983 wasapproximately 606,000 pounds (HSDB 1988). Commercial piperidine is suppliedin two grades, 95 and 98 percent pure (Sax and Lewis 1987). |
| Preparation | Usually prepared by electrolytic reduction of pyridine. |
| Application | The secondary amine piperidine is highly reactive and is therefore frequently employed as an intermediate for pharmaceuticals and for plant protection agents. It is also used as a vulcanization accelerator in rubber manufacture and as an oil or fuel additive. Piperidine and, in many cases, piperidine acetate are useful catalysts for condensation reactions, e.g., the Knoevenagel reaction, aldol condensation, and the condensation of a nitroparaffin with an aldehyde. However, for the last of these reactions, diethylamine is the preferred catalyst. The use of piperidine is particularly advisable where the reactants or products are unstable in the presence of stronger bases. |
| Definition | piperidine: A saturated heterocycliccompound having a nitrogen atom ina six-membered ring, C5H11N; r.d.0.86; m.p. –7°C; b.p. 106°C. The structureis present in many alkaloids |
| Brand name | Cypentil (Abbott). |
| Aroma threshold values | Detection: 65.8 to 70.6 ppm |
| General Description | A 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 Reactions | Highly flammable. Miscible in water. |
| Reactivity Profile | 1-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 Hazard | Strong 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 Hazard | Piperidine is a highly toxic compound. Theacute oral toxicity is high in many species oftest animals. The oral LD50 values in miceand rabbits are 30 and 145 mg/kg, respectively(NIOSH 1986). The liquid is moderatelytoxic by skin absorption. Inhalationtoxicity in experimental animals was low,however. A 4-hour exposure to 4000 ppmwas lethal to rats. Piperidine is corrosive toskin. Contact with eyes can produce severeirritation. |
| Health Hazard | An irritation threshold of 26 p.p.m. has been reported from studies on humanvolunteers (Bazarova and Migukina 1975). Levels of 2 to 5 p.p.m. in air have beenrecorded during the transfer of piperidine from drums in a semi-closed system. Atthis level, the vapors were intolerable but no irritation was observed (ANON1982). In an accidental case of skin exposure, third-degree burns developed afteronly 3 min of skin contact (Linch 1965). Piperidine has a pronounced emetic effectin humans. When administered to schizophrenic patients at doses of 1 to 6 g/d, itwas 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 Hazard | 1-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. |
| Flammability and Explosibility | Highly flammable |
| Industrial uses | Piperidine is used as a solvent, a curing agent for rubber and epoxy resins, acatalyst in silicone esters, an intermediate in organic synthesis and as a complexingagent (HSDB 1988; Reinhardt and Britelli 1981). It is a trace constituent in oilsand 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 andBellanca 1975). |
| Safety Profile | Poison by ingestion,skin contact, and intraperitoneal routes.Moderately toxic by subcutaneous route.Mildly toxic by inhalation. An experimentalteratogen. Experimental reproductive effectsby inhalation. A skin irritant. Mutation datareported. A very dangerous fire hazard whenexposed to heat, flame, or oxidizers. Canreact vigorously with oxidzing materials. Tofight fire, use alcohol foam, CO2, drychemical. Explodes on contact with 1-perchloryl-piperidme, dqanofurazan, N-nitrosoacetadde. When heated todecomposition it emits highly toxic fumes ofNOx. Used in agriculture andpharmaceuticals, and as an intermediate forrubber accelerators. Used in production ofdrugs of abuse. |
| Potential Exposure | Piperidine 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. |
| Carcinogenicity | No tumors were produced inrats given piperidine (0.09%) in drinking water for1 year. Mice receiving 19 doses of 50 mg/kg by intraperitonealinjection within 61 weeks followed by an 18-weekobservation period showed no increase in cancer incidences(251). Piperidine and sodium nitrite given togetheralso failed to produce tumors. The failure of this treatment was surprising because nitrosopiperidine induced a highincidence of lung and esophageal tumors. The authorssuggest that the relative strong basicity of piperidinereduced the rate of reaction with nitrite to such an extentthat an ineffective amount of nitrosopiperidine wasformed. In mice that had cholesterol pellets containingpiperidine implanted in their bladders and were givensodium nitrite in their drinking water, an increase in bladdercancers was produced. Piperidine given as a series of24 injections in groups of mice failed to produce lungtumors in the strain A mouse cancer screen. Whenpiperidine and sodium nitrite were incubated in the isolatedrat urinary bladder, nitrosopiperidine was detected in thebladder contents. No studies designed to evaluate the carcinogenicpotential of piperidine alone following lifetimeexposures have been reported. |
| Metabolism | Piperidine is readily absorbed through the gastrointestinal tract, skin and lungs(HSDB 1988). In hens, 35 to 70% of an injected dose is rapidly excretedunchanged in the urine (Williams 1959; Sperber 1949). Rabbits also excretepiperidine unchanged (Hildebrandt 1900). When injected intraventricularly intorats, 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 identifiedas 3- and 4-hydroxypiperidine. Both compounds were also found in untreatedanimals and thus are probably metabolites of piperidine of exogenous or endogenousorigin. These metabolites represent a detoxification mechanism, since theylack the potent pharmacological activities of the parent compound. Two unidentifiedmetabolites were assumed to be conjugates. In a much earlier study, Novelloet al (1926) claimed that piperidine was excreted as the ethereal sulfate. Metabolicstudies of analgesics and anesthetics containing the piperidine ring have demonstratedthe occurrence of N-hydroxylation, formation of a 6-oxo-derivative, and C-oxidative ring cleavage (Oelschlager and Al Shaik 1985). N-nitrosopiperidinehas been synthesized from piperidine and sodium nitrite in the gastric contents,R.L. Reedisolated stomach and isolated small intestine of rats (Alam et al 1971; Epstein1972). |
| Shipping | UN2401 Piperidine, Hazard Class: 8; Labels: 8-Corrosive material, 3-Flammable liquid. |
| Purification Methods | Dry 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 |
| Incompatibilities | Piperidine 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. |
| Toxics Screening Level | The initial threshold screening level (ITSL) for piperidine is 140 μg/m3based on an annual averaging time. |
Piperidine Preparation Products And Raw materials
| Raw materials | Sodium-->Hydrogen-->Piperidine hydrochloride |
| Preparation Products | 3-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-->Syringaldehyde-->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 |
