Allylamine CAS 107-11-9
Introduction：Basic information about Allylamine CAS 107-11-9, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Allylamine Basic information
| Product Name: | Allylamine |
| Synonyms: | 1-Aminoprop-2-ene;2-Propen-1-ylamin;2-Propene-1-amine;2-Propenylamine;Allylamin;CH2=CHCH2NH2;3-Aminopropen;3-Aminopropylene |
| CAS: | 107-11-9 |
| MF: | C3H7N |
| MW: | 57.09 |
| EINECS: | 203-463-9 |
| Product Categories: | Pharmaceutical Intermediates |
| Mol File: | 107-11-9.mol |
Allylamine Chemical Properties
| Melting point | -88 °C (lit.) |
| Boiling point | 53 °C (lit.) |
| density | 0.761 g/mL at 25 °C (lit.) |
| vapor density | 2 (vs air) |
| vapor pressure | 4.09 psi ( 20 °C) |
| refractive index | n |
| Fp | −20 °F |
| storage temp. | Flammables area |
| solubility | miscible with water, alcohol, chloroform and ether |
| form | Crystalline or Granular Powder |
| pka | 9.49(at 25℃) |
| color | White or almost white |
| explosive limit | 22% |
| Water Solubility | miscible |
| Sensitive | Air Sensitive |
| Merck | 14,287 |
| BRN | 635703 |
| Dielectric constant | 5.96 |
| Stability: | Stability Air sensitive. Serious fire hazard. Highly flammable - note low flash point. May be ignited at temperatures close to ambient. |
| InChI | 1S/C3H7N/c1-2-3-4/h2H,1,3-4H2 |
| InChIKey | VVJKKWFAADXIJK-UHFFFAOYSA-N |
| SMILES | NCC=C |
| LogP | 0.13 at 20℃ |
| CAS DataBase Reference | 107-11-9(CAS DataBase Reference) |
| NIST Chemistry Reference | 2-Propen-1-amine(107-11-9) |
| EPA Substance Registry System | Allylamine (107-11-9) |
Safety Information
| Hazard Codes | F,T,N |
| Risk Statements | 11-23/24/25-51/53 |
| Safety Statements | 9-16-24/25-45-61 |
| RIDADR | UN 2334 6.1/PG 1 |
| WGK Germany | 2 |
| RTECS | BA5425000 |
| F | 10 |
| TSCA | TSCA listed |
| HazardClass | 6.1 |
| PackingGroup | I |
| HS Code | 29211980 |
| Storage Class | 3 - Flammable liquids |
| Hazard Classifications | Acute Tox. 1 Dermal Acute Tox. 1 Inhalation Acute Tox. 3 Oral Aquatic Chronic 2 Eye Dam. 1 Flam. Liq. 2 Skin Corr. 1A |
| Hazardous Substances Data | 107-11-9(Hazardous Substances Data) |
| Toxicity | LD50 i.p. in mice: 49 mg/kg (Hine) |
| Description | Allylamine is a primary unsaturated alkylamine and in thisreview refers to monoallylamine. Allylamine can also be usedgenerically to describe the secondary (diallyl-) and tertiary(triallyl-) amine derivatives of monoallylamine, as well asother more complex alkylamines. Allylamine is a colorless,flammable liquid and is volatile and reactive with oxidizingmaterials. Allylamine has a strong ammonia odor, is acutelytoxic by all routes of exposure, and produces cardiotoxicity ina manner that has been well characterized by in vivo and in vitromethods. In addition to its use as an industrial chemical,allylamine is utilized as a model compound for basic researchinvestigations into mechanisms of cardiovascular disease basedon the nature of the cardiac and vascular lesions observedfollowing allylamine exposure. |
| Chemical Properties | colourless liquid |
| Chemical Properties | Allylamine is a highly flammable, colorless liquid. Strong ammonia odor. |
| Chemical Properties | Allylamine is highly reactive, combining the reactivity of amines with the unsaturationof the allyl group (Schweizer et al 1978). Reaction with halogens, forexample, gives the corresponding halogenated propylamine in high yield. |
| Uses | In the manufacture of mercurial diuretics. |
| Uses | Allylamine ismanufactured fromallyl chloride andammonia.It is used as a solvent and in organic syntheses, including thesynthesis of rubber, mercurial diuretics, sedatives, and antiseptics(238). It is also used in the synthesis of ion-exchangeresins. |
| Uses | Allylamine is used as an industrial solvent and in organicsynthesis, including rubber vulcanization, synthesis of ionexchangeresins, and as an intermediate in pharmaceuticalsynthesis. Derivatives of allylamine are utilized as both veterinaryand human pharmaceuticals, including the antifungalagent terbinafine. Allylamine has been used since the 1940s asa research tool for investigations of cardiovascular disease, withthe earliest studies using allylamine to induce initial vascularinjury in animal models of atherogenesis. Additionally, allylaminehas been used to model myocardial infarction andvascular injury in animal models of human cardiovasculardisease. |
| Definition | ChEBI: Allylamine is an alkylamine. |
| Production Methods | Allylamine is produced by reaction of allyl chloride with ammonia. The amine isalso a natural constituent of foodstuffs (Shumkova and Karpova 1981; Mochalovet al 1981) and is present in wastewater from oil shale retorting (Daughton et al1985). |
| General Description | A colorless to light yellow colored liquid with a strong ammonia-like odor. Less dense than water. Vapors are heavier than air. Toxic by inhalation, ingestion and skin absorption. Irritates skin, eyes and mucous membranes. Flash point below 0°F. Boiling point 130°F. Used to make pharmaceuticals and other chemicals. |
| Air & Water Reactions | Highly flammable. Water soluble. |
| Reactivity Profile | Allylamine reacts violently with strong oxidizing agents and acids. Attacks copper and copper compounds [Handling Chemicals Safely 1980. p. 123]. Reacts with hypochlorites to give N-chloroamines, some of which are explosives when isolated [Bretherick 1979. p. 108]. |
| Health Hazard | Acute: an eye, skin, and respiratory tract irritant, which is highly toxic if inhaled or ingested and moderately toxic if absorbed on skin. Ingestion or inhalation may cause death or permanent injury after very short exposure to small quantities. Skin absorption may cause irreversible and reversible changes. Toxic air concentration (TClo) in humans is 5 ppm over 5 minutes. Vapors are extremely unpleasant and may ensure voluntary avoidance of dangerous concentrations. Will irritate nose and throat at 2.5 ppm. |
| Health Hazard | Allylamine is a strong eye and respiratory tract irritant (Windholz et al 1983) andexposure to it causes transient irritation of mucous membranes of the nose, eye andmouth with lacrimation, coryza and sneezing (HSDB 1989). Exposure to 14 p.p.m.allylamine caused intolerable irritation of the eyes and respiratory tract (Grant1974). |
| Fire Hazard | Flammable when exposed to heat, sparks, or flame. Vapor forms explosive mixtures with air over a wide range. Use caution when approaching fire and applying water. Vapor explosion and poison hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Can react with oxidizing materials. When heated to decomposition, Allylamine emits toxic fumes. Avoid oxidizing materials. Stable, avoid heating to decomposition. May become unstable at elevated temperatures and pressures or may react with water with non-violent release of energy. |
| Flammability and Explosibility | Highly flammable |
| Industrial uses | Allylamine is used in the synthesis of ion-exchange resins and for water-dispersiblecopolymers useful for water purification and as flocculating agents(Schweizer et al 1978). The amine is also used for the preparation of pharmaceuticalsincluding mercurial diuretics and antifungal agents (HSDB 1989). |
| Safety Profile | Poison by inhalation, ingestion, intraperitoneal, and skin contact routes. Human systemic effects by inhalation: lacrymation and lung effects. A systemic irritant. Mutation data reported. A severe eye and skin irritant. Extraordnary precautions against fumes are advised. Dangerous fire and explosion hazard when exposed to heat, flame, or oxidzers. Highly reactive. When heated to decomposition it emits toxic fumes of NOx. To fight fire, use alcohol foam, CO2, dry chemical. See also ALLYL COMPOUNDS and AMINES. |
| Potential Exposure | Compound |
| Environmental Fate | Allylamine exposure results in myocardial damage and intimalproliferation of vascular smooth muscle cells in multipleanimal species. The mechanism for these distinctive cardiovascularlesions is believed to be related to its bioactivation toacrolein and possibly hydrogen peroxide. Several lines ofevidence support this hypothesis; SSAO is highly active invascular tissue where allylamine predominantly distributes,incubation of homogenates of vascular tissue with allylamineresults in the generation of acrolein and hydrogen peroxide,and pretreatment with a semicarbazide inhibitor of SSAOreduces or eliminates the hypercontraction and vasospasmassociated with allylamine exposure in vitro. Researchers havetaken advantage of the distinctive lesions that result fromvarious exposures to allylamine and have used it as chemicaltool to induce animal models of cardiovascular dysfunctionthat resemble human disease. |
| Metabolism | The uptake, tissue distribution, excretion and pharmacokinetics of a 450 mg/kgoral dose of [14C]-allylamine has been studied over a 2 h period in maleSprague-Dawley rats (Boor 1985). The amine was rapidly absorbed from thegastrointestinal tract and quickly accumulated and then eliminated from tissueswith a short halflife of less than 1 h that seemed to fit a one compartment model.The 14C-label was rapidly excreted in urine and no radioactivity was found infeces. Allylamine or its metabolites showed an unusual predilection for accumulatingin elastic and muscular arteries with the highest radioactivity (5- to 10-foldhigher than most other organs) occurring in the aorta. Radioactivity in all othertissues was generally much lower and fairly equal. At 5,10,15 and 20 min after ani.v. dose of [14C]-allylamine, 30 to 33% of the admitted radioactivity was localizedin the aortas of adult Sprague-Dawley rats. By 30 min, 17% of the administereddose was still present in that tissue (Hysmith and Boor 1985). Upon differentialcentrifugation most of the radioactivity in the aorta was found to be localized inthe mitochondria. Further in vitro investigations (Hysmith and Boor 1987) showedthe specific binding of radioactivity from [14C]-allylamine to isolated rat aorta andheart mitochondria at both high affinity and low affinity binding sites. As much as23 and 43% of the bound radioactivity was covalently linked to aorta and heartmitochondria, respectively. The monoamine oxidase B inhibitor, deprenyl, significantlyreduced both the specific and covalent binding of radioactivity from[14C]-allylamine in phospholipase treated mitochondria while the benzylamineoxidase inhibitor, semicarbazide, had no effect on [14C]-allylamine binding. Theseresults suggest that monoamine oxidase can convert allylamine to a highly reactivemetabolite that selectively covalently binds to heart mitochondria and that thismay explain the cardiotoxicity associated with this amine. In vitro studies show that allylamine is converted by homogenates of various rattissues (heart, aorta, skeletal muscle, lung) to acrolein (Boor et al 1981; Nelsonand Boor 1982). Conversion of allylamine to acrolein in human tissue was 58, 8and 6% in aorta, myocardium and liver, respectively, while in the rat thepercentages of acrolein formation were 95, 18, 9 and 5% in aorta, lung, skeletalmuscle, and heart preparations, respectively (Boor and Nelson 1982). Purifiedbovine plasma amine oxidase and porcine kidney diamine oxidase convertedallylamine to acrolein in vitro (Nelson and Boor 1982). Studies with selectiveinhibitors suggested that benzylamine oxidase is the active enzyme in oxidizingallylamine. Inhibition of benzylamine oxidase with either semicarbazide orphenelzine protected aortic smooth muscle cells from allylamine-induced cytolethalinjury (Hysmith and Boor 1988). Inhibition of benzylamine oxidase markedlyaltered the subcellular distribution of radioactivity from [14C]-allylamine in aorticsmooth muscle cells, with the administered radioactivity no longer being localizedin the mitochondria. The sole urinary metabolite of allylamine in vivo has beenidentified as 3-hydroxypropylmercapturic acid (Boor et al 1987; Kage and Young1972). Parallel experiments showed glutathione (GSH) depletion in severalorgans, the most marked occurring in aorta, blood and lung. These findingsindicate that allylamine was metabolized in vivo to the highly reactive aldehyde,acrolein, which was subsequently converted to a mercapturic acid through a GSHconjugation pathway. |
| Shipping | UN2334 Allylamine, Hazard class: 6.1; Labels: 6.1-Poison Inhalation Hazard, 3-Flammable liquids, Inhalation Hazard Zone B. |
| Purification Methods | Purify allylamine by fractional distillation from calcium chloride. It causes sneezing and tears. [Beilstein 4 IV 1057.] |
| Toxicity evaluation | The production and use of allylamine as an industrial solventmay result in environmental releases to the air, water, and soil.Allylamine is freely soluble in water, alcohol, chloroform,and most solvents. The vapor pressure at 20°C is 198mm Hg,the Henry’s law constant is estimated to be 9.95×10-6 atmm3 mol-1, and the octanol/water partition coefficient (log Kow)is estimated to be 0.21. |
| Incompatibilities | May form explosive mixture with air. Oxidizing materials and acids may cause a violent reaction. Attacks copper and corrodes active metals (i.e., aluminum, zinc, etc.). |
| Waste Disposal | High temperature incineration; encapsulation by resin or silicate fixation. |
Allylamine Preparation Products And Raw materials
| Raw materials | Allyl chloride |
| Preparation Products | (R)-(+)-1-Boc-3-aminopyrrolidine-->(R)-3-(Boc-amino)pyrrolidine-->Fluvastatin sodium salt-->2,2-Dibromo-2-cyanoacetamide-->selfcrossline adhesive 7601-->ALLYLUREA-->tert-butyl azidoformate-->Triethyl 1,3,5-benzenetricarboxylate-->N-ALLYLANILINE-->3-chloropropylamine-->3-AMINOPROPYLDIMETHYLETHOXYSILANE-->ALLYLHYDRAZINE-->5-Fluoro-3-methylindole-->Morpholine |
