HuagongsheHuagongshe Chemistry Print Report · For research reference only
Piperidine
Piperdine · PIP · Piperidin · HEXAHYDROPYRIDINE · PPR · FEMA 2908 · Cyclopentimine · azacyclohexane
Identifiers & Physical Properties
| CAS No. | 110-89-4 |
|---|---|
| Molecular formula | C5H11N |
| Average molar mass | 85.15 g/mol |
| Monoisotopic mass | 85.08914935 g/mol |
| SMILES | C1CCNCC1 |
| InChIKey | NQRYJNQNLNOLGT-UHFFFAOYSA-N |
| PubChem CID | 8082 |
| ChEMBL | CHEMBL15487 |
| ChEBI | CHEBI:18049 |
| EC No. | 203-813-0 |
| DTXSID | DTXSID6021165 |
Chemical & Physical Properties
| XLogP | 0.8 |
|---|---|
| Topological polar surface area | 12 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 1 |
| Rotatable bonds | 0 |
| Heavy atoms | 6 |
| Formal charge | 0 |
| Complexity | 30.9 |
| Chemical classes | Nitrogen Compounds -> Amines, CyclicFlammable agents - 3rd degree |
| pH | Strong base12.6 (100g/l, H2O, 20°C) |
| SpringerMaterials Properties | 15N nuclear magnetic resonance spectrum |
| Fragrances | Fragrance Ingredient (Piperidine) -> IFRA transparency List |
| LogP (partition coefficient) | log Kow = 0.84 |
| Odor | AMINE-LIKE ODORHEAVY, SWEET, FLORAL, ANIMAL ODOROdor of pepperat 1.00 % in propylene glycol. heavy sweet floral animal |
| Taste | BURNING PEPPERY TASTE |
| Food additives | FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| Density | 0.8622 at 68 °F (EPA, 1998) - Less dense than waterwill float0.8622 at 20 °C/4 °CRelative density (water = 1): 0.860.858-0.8620.8622 @25 °C0.930 g/mL at 20 °C |
| Flavoring agents | EU Flavoring substances |
| Color/Form | CLEAR, COLORLESS LIQUID |
| Solubility | Miscible (NTP, 1992)Miscible in ethanolsoluble in ethyl ether, acetone, benzene, chloroformMiscible in water1000 mg/mL at 20 °CSolubility in water: miscibleSoluble in water, ethermiscible in water and alcoholsoluble in ether, acetone, benzene and chloroform maximum allowable concentration: not establishedmore toxic, irritating and volatile than pyridine (Reinhardt and Brittelli 1981). |
| Melting point | -11 °C |
| Boiling point | 106 °C(lit.) |
| Vapor density | 3 (vs air) |
| Vapor pressure | 23 mm Hg ( 20 °C) |
| Refractive index | n20/D 1.452(lit.) |
| FEMA | 2908 | PIPERIDINE |
| FLAVIS Number | 14.010 | Piperidine |
| Flash point | 16 °C(lit.) |
| Storage conditions | Store in dark! |
| Physical state | liquid |
| pKa (acidity coefficient) | 11.123(at 25℃) |
| Color | APHA: ≤50 |
| Explosive limits | 1.5-10.3%(V) |
| Odor type | animal |
| Biological source | synthetic |
| Specific heat capacity | Cp(liquid): 2.11 J/(g·K), at 25℃ |
| Sensitivity | Air Sensitive |
| JECFA Number | 1607 |
| Merck | 14,7468 |
| BRN | 102438 |
| Henry's law constant | 2.8×100 mol/(m3Pa) at 25℃, Bernauer and Dohnal (2009) |
| 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 (partition coefficient) | 0.61 |
| Surface tension | 30.27mN/m at 293.15K |
| CAS DataBase Reference | 110-89-4(CAS DataBase Reference) |
| Substances Added to Food (formerly EAFUS) | PIPERIDINE |
| EWG's Food Scores | 1 |
| FDA UNII | 67I85E138Y |
| NIST Chemistry Reference | Piperidine(110-89-4) |
| EPA Substance Registry System | Piperidine (110-89-4) |
| UNSPSC Code | 85151701 |
| NACRES | NA.31 |
| GHS pictogram | GHS02,GHS05,GHS06 |
| Signal word | Danger |
| GHS hazard statements | H225-H302-H311+H331-H314 |
| GHS precautionary statements | P210-P280-P301+P312-P303+P361+P353-P304+P340+P310-P305+P351+P338 |
| Personal protective equipment (PPE) | Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter |
| Hazard symbols | T,F |
| Risk statements (R) | 61-10-20/21-34-23/24-11-52-24-20/22 |
| Safety statements (S) | 53-16-26-36/37/39-45-27 |
| UN transport number | UN 2401 |
| Water hazard class (WGK) | 3 |
| RTECS number | TM3500000 |
| F | 3-34 |
| Autoignition temperature | 320 °C |
| TSCA inventory status | TSCA listed |
| Hazard class | 8Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 4 OralEye Dam. 1Flam. Liq. 2Skin Corr. 1B |
| Packing group | I |
| Customs code | 29333210 |
| Storage class | 3 - Flammable liquids |
| Hazardous substances data | 110-89-4(Hazardous Substances Data) |
| Toxicity | LD50 orally in rats: 0.52 ml/kg (Smyth) |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | DangerH225: Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P270, P271, P280, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P321, P361+P364, P363, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]P210, P233, P240, P241, P242, P243, P260, P261, P262, P264, P270, P271, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P321, P330, P361+P364, P363, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement) |
|---|---|
| Regulatory information | Chemical: PiperidineList I Chemical: A chemical specified by regulation that, in addition to legitimate uses, is used in manufacturing a controlled substance in violation of the Act and is important to the manufacture of a controlled substance. (21 eCFR 1310.02)Regulation (EC) No 1831/2003 (amended)Piperidine is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Piperidine 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)Status: Active Update: 03-11-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/13488Piperidine: HSNO Approval: HSR001260 Approved with controls |
| Other safety information | IMAP assessments - Piperidine: Human health tier II assessment |
| DOT label | Corrosive Flammable Liquid |
| Fire hazards | Piperidine evolves explosive concentrations of vapor at normal room temperatures. When heated to decomposition, it emits highly toxic fumes of nitrogen oxides. Dangerous, when exposed to heat, flame, or oxidizers. Avoid 1-Perchlorylpiperidine and oxidizing materials. Piperidine is a reactive compound and forms complexes with the salts of heavy metals. It evolves explosive concentrations of vapor at normal room temperatures. Keep away from igniting sources and heat. (EPA, 1998)· Flammable/combustible material.Highly flammable. Vapour/air mixtures are explosive. |
| Fire potential | This substance ... evolves explosive concentrations of vapor at normal room temperatures.Dangerous /fire hazard/, when exposed to heat, flame or oxidizers. |
| Health hazards | 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. (EPA, 1998)· May cause toxic effects if inhaled or ingested. |
| Hazards summary | Corrosive to skin[Quick CPC] High inhalation exposure can cause pulmonary edema[ICSC] Signs of toxicity in acute animal studies included respiratory distress, ataxia, weakness, paralysis, and convulsionsFor humans, the irritation threshold is 26 ppmworkers can tolerate levels of 2-5 ppm for only a short period because of the odor[AIHA] Oral doses of 30-60 mg/kg may cause weakness, vomiting, labored respiration, muscular paralysis, and asphyxia[NTP] Safe when used as a flavoring agent in food[JECFA] A skin sensitizer in guinea pigs[EPA ChAMP] Causes impaired liver function tests in repeated dose inhalation studies of rats[RTECS] |
| DOT ID and guide | 2401 132 |
| FDA requirements | Piperidine is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: 1) the quantity added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) when intended for use in or on food it is of appropriate food grade and is prepared and handled as a food ingredient.The following chemical has been specifically designated by the Administrator of the Drug Enforcement Administration as subject to the provisions of this part and parts 1309 and 1313 of this chapter. Piperidine and its salts are List 1 chemicalsDEA Code: 2704. |
| Reactive group | Amines, Phosphines, and Pyridines |
| EC classification | Symbol: F, TR: 11-23/24-34S: (1/2)-16-26-27-45 |
| UN classification | UN Hazard Class: 8UN Subsidiary Risks: 3UN Pack Group: I |
| Fire fighting | Keep unnecesary people awayisolate hazard area and deny entry. Stay upwindkeep out of low area. Wear self-contained (positive pressure if available) breathing apparatus and full protective clothing. Isolate for 1/2 mile in all directions if tank car or truck is involved in fire.Use water in large amounts, powder, alcohol-resistant foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. |
| First aid measures | Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Do NOT induce vomiting. Give one or two glasses of water to drink. Refer for medical attention . |
| Accidental release measures | · CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. |
| First aid | Warning: Piperidine is a basic irritant of skin and mucous membranes. May cause permanent injury after short exposure to small amounts.General First Aid: |
| Safe storage | Fireproof. Separated from strong oxidants, acids and incompatible materials. See Chemical Dangers. |
| Exposure control and personal protection | · Wear positive pressure self-contained breathing apparatus (SCBA). |
| Fire fighting procedures | This chemical is a flammable liquid. Small fires: dry chemical, carbon dioxide, water spray, or alcohol foam. Large fires: water spray, fog, or alcohol foam. Move container from fire area if you can do so without risk. Do not get water inside container. Cool containers that are exposed to flames with water from the side until well after fire is out. Withdraw immediately in case of rising sound from venting safety device or any discoloration of tank due to fire. Keep unnecessary people awayisolate hazard area and deny entry. Stay upwindkeep out of low areas. Wear self-contained (positive pressure if available) breathing apparatus and full protective clothing. Isolate for ½ mile in all directions if tank car or truck is involved in fire. Poisonous gases including nitrogen oxides are produced in fire. Vapors are heavier than air and will collect in low areas. Vapors may travel long distances to ignition sources and flashback. Vapors in confined areas may explode when exposed to fire. Containers may explode in fire. Storage containers and parts of containers may rocket great distances, in many directions. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors, or shows any signs of deforming), withdraw immediately to a secure position. If employees are expected to fight fires, they must be trained and equipped in OSHA 1910.156Powder, alcohol-resistant foam, water in large amounts, carbon dioxide.Alcohol foam, carbon dioxide, dry chemical.If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Use foam, dry chemical, or carbon dioxide. Keep run-off water out of sewers and water sources. |
| Storage conditions | Fireproof. Separated from strong oxidants, acids, incompatible materials See Chemical Dangers.Store in tightly closed containers in a cool, well vented area away form oxidizers. Where possible, automatically pump liquid from drums or other storage containers to process containers. Sources of ignition such as smoking and open flames are prohibited where this chemical is handled, used, or stored. Metal containers involving the transfer of 5 gallons or more of this chemical should be grounded and bonded. Drums must be equipped with self-closing valves, pressure vacuum bungs, and flame arresters. Use only non-sparking tools and equipment, especially when opening and closing containers of this chemical. Whenever this chemical is used, handled, manufactured, or stored, use explosion-proof electrical equipment and fittings. |
| Cleanup methods | Collect leaking liquid in sealable containers. Absorb remaining liquid in sand or inert absorbent and remove to safe place. (Extra personal protection: self-contained breathing apparatus.)Evacuate and restrict persons not wearing protective equipment from area of spill or leak until clean-up is complete. Shut off ignition sourcesno flares, smoking, or flames in hazard area. Do not touch spilled materialstop leak if you can do so without risk. Use water spray to reduce vaporsdo not get water inside container. Small spills: absorb with sand or other noncombustible absorbent material and place into containers for later disposal. Large spills: dike far ahead of spill for later disposal. Ventilate area of spill or leak. Absorb liquids in vermiculite, dry sand, earth, peat, carbon, or a similar material and deposit in sealed containers. Keep this chemical out of a confined space, such as a sewer, because of the possibility of an explosion, unless the sewer is designed to prevent the build up of explosive concentrations. It may be necessary to contain and dispose of this chemical as a hazardous waste. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection or your regional office of the federal EPA for specific recommendations. If employees are required to clean-up spills, they must be properly trained and equipped. OSHA 1910.120(q) may be applicable. |
| Nonfire spill response | Excerpt from ERG Guide 132 [Flammable Liquids - Corrosive]: |
| Disposal methods | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations.(a) Dissolve in such combustible solvent as alcohols, benzene, etc. Spray the solution into the furnace with afterburner and scrubber. (b) Pour into sodium bicarbonate or a mixture of sand/soda ash (9:1). After mixing, transfer into a paper carton filled with packing paper. Burn in an open furnace, or more efficiently in the furnace with afterburner and scrubber. |
| Spillage disposal | Personal protection: self-contained breathing apparatus. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. |
| Interactions | A study in ddy mice successfully demonstrated that simultaneous administration of nitrite and piperidine led to a marked increase in the incidence of urinary bladder cancer when cholesterol pellets containing piperidine hydrochloride were surgically implanted into the urinary bladder and the rats were given sodium nitrite (0.1%) in their drinking water for 40 weeks. /Piperidine hydrochloride/ |
| Ecotoxicity values | LC50 Daphnia magna /water flea/ 8.234 mg/L /48 hr. /Conditions of bioassay not specified/LC50 Pimephales promelas (fathead minnow) 129.594 mg/L /96 hr. /Conditions of bioassay not specified/ |
| Environmental fate | ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), piperidine, which has a vapor pressure of 32.1 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase piperidine 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 4 hours(SRC), calculated from its rate constant of 8.9X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). |
| Food survey values | Piperidine concns in various West German foods and drink werebroken butterbeans 0.1 mg/kg, paprika 5.2 mg/kg, paprika with brine 5.6 mg/L, pepperoni 3.4 mg/kg, pepperoni with brine 0.4 mg/L, celery 1 mg/kg, celery with brine 0.1 mg/L, Bismarck herring 0.3 mg/kg, salted herring 0.7 mg/kg, smoked herring 0.2 mg/kg, Limburger cheese trace, coffee extract 2, freeze-dried coffee 2, freeze-dried coffee 1, defatted cocoa 9 mg/kg, barley 1 mg/kg, hops 2.5 mg/kg, and malt <0.1 mg/kg(1). Piperidine was also found in baked ham at 0.2 ppm(2) and 0.81 ppm(3), coffee at 1 ppm(2), fish sausage at 9 ppb(3) and as a volatile component of boiled beef(4).Piperidine occurs at low levels in a variety of food products including baked ham (0.2 ppm), milk (0.11 ppm), coffee (1 ppm dry) and canned fish. |
| Adverse effects | Neurotoxin - Other CNS neurotoxin |
| Exposure routes | The substance can be absorbed into the body by inhalation of its vapour, through the skin and by ingestion. |
| Milk Concentrations | Piperidine was found in canned milk at 0.3 ppm and whole milk at 0.11 ppm(1). |
| Plant Concentrations | Piperidine was identified, not quantified, in various plants and roots from Nigeria, Africa, which are used as native medicinals, namely Pleiocera barteri, Alsotonia boonei, and Morinda lucida, and believed to have antimalaria activity(1). Piperidine has been identified in tobacco leaf(2,3) at concentrations of 45 ug/cigarette(3). |
| Signs and Symptoms | Burning sensation. Cough. Laboured breathing. Shortness of breath. Sore throat. Symptoms may be delayed.MAY BE ABSORBED! Redness. Skin burns. Pain.Redness. Pain. Blurred vision. Severe deep burns.Abdominal pain. Burning sensation. Laboured breathing. Shock or collapse. |
| Effluent Concentrations | Piperidine was identified in the primary effluent at a concentration of 13 ug/L from municipal wastewater treatment plants(1). |
| Natural Pollution Sources | Piperidine was identified in various plants and roots from Africa(1), in tobacco leaf(2,3) in small amounts in black pepper(4), and is commonly detected in other food products(5,6). Piperidine has been found in brain, skin, and urine of animals and in the brain, cerebrospinal fluid, and urine of humans(7). |
| Human Toxicity Excerpts | /HUMAN EXPOSURE STUDIES/ An irritation threshold of 26 ppm has been reported from studies on human volunteers./HUMAN EXPOSURE STUDIES/ In a study in volunteers who received iv infusions of 100 mg piperidine in physiological saline solution for 30 minutes starting at sleep onset, piperidine was not noted to cause any alteration in the standard sleep parameters measured. Sleep-related secretion of growth hormone was enhanced by piperidine./SIGNS AND SYMPTOMS/ Piperidine has a pronounced emetic effect in humans. When administered to schizophrenic patients at doses of 1 to 6 g/day, it was shown to cause nausea and a subjective sense of well being./SIGNS AND SYMPTOMS/ Acute local: irritant 3. 3= high: may cause death or permanent injury after very short exposure to small amt. Acute systemic: ingestion 2. 2= moderate: may involve both irreversible & reversible changes not severe enough to cause death or permanent injury.For more Human Toxicity Excerpts (Complete) data for PIPERIDINE (7 total), please visit the HSDB record page. |
| CERCLA reportable quantities | Releases of CERCLA hazardous substances are subject to the release reporting requirement of CERCLA section 103, codified at 40 CFR part 302, in addition to the requirements of 40 CFR part 355. Piperidine is an extremely hazardous substance (EHS) subject to reporting requirements when stored in amounts in excess of its threshold planning quantity (TPQ) of 1,000 lbs. |
| DHS Chemicals of Interest (COI) | Piperidine110000Flammable chemical that can be released at a facility. |
| F | 3-34 |
| Personal protective equipment (PPE) | Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| RTECS number | TM3500000 |
| UN transport number | UN 2401 |
| Customs code | 29333210 |
| Toxicity | LD50 orally in rats: 0.52 ml/kg (Smyth) |
| Risk statements (R) | 61-10-20/21-34-23/24-11-52-24-20/22 |
| Signal word | Danger |
| GHS pictogram | GHS02,GHS05,GHS06 |
| Hazard symbols | T,F |
| Safety statements (S) | 53-16-26-36/37/39-45-27 |
| Hazard class | 8Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 4 OralEye Dam. 1Flam. Liq. 2Skin Corr. 1B |
| Storage class | 3 - Flammable liquids |
| Packing group | I |
| GHS hazard statements | H225-H302-H311+H331-H314 |
| REACH registrations | Active |
| Autoignition temperature | 320 °C |
| GHS precautionary statements | P210-P280-P301+P312-P303+P361+P353-P304+P340+P310-P305+P351+P338 |
| Hazardous substances data | 110-89-4(Hazardous Substances Data) |
Applications & Uses
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) (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).
Uses
It is used in organic synthesis, especially inthe preparation of many crystalline derivativesof aromatic nitro compounds.
Uses
Piperidine is an organic heterocyclic amine widely used as building block and reagent in the synthesis of organic compounds including pharmaceuticals.
Uses
Fits Applied Biosystems 431 and 433A peptide synthesizers.
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.
Preparation & Synthesis
Preparation
Usually prepared by electrolytic reduction of pyridine.