107-11-9 Usage
Chemical Description
Different sources of media describe the Chemical Description of 107-11-9 differently. You can refer to the following data:
1. Allylamine is an organic compound that contains an allyl group and an amino group.
2. Allylamine, para-chlorobenzaldehyde, and acetic acid are used as reactants in the Ugi reaction.
Description
Allylamine is a primary unsaturated alkylamine and in this
review refers to monoallylamine. Allylamine can also be used
generically to describe the secondary (diallyl-) and tertiary
(triallyl-) amine derivatives of monoallylamine, as well as
other more complex alkylamines. Allylamine is a colorless,
flammable liquid and is volatile and reactive with oxidizing
materials. Allylamine has a strong ammonia odor, is acutely
toxic by all routes of exposure, and produces cardiotoxicity in
a manner that has been well characterized by in vivo and in vitro
methods. In addition to its use as an industrial chemical,
allylamine is utilized as a model compound for basic research
investigations into mechanisms of cardiovascular disease based
on the nature of the cardiac and vascular lesions observed
following allylamine exposure.
Chemical Properties
Different sources of media describe the Chemical Properties of 107-11-9 differently. You can refer to the following data:
1. colourless liquid
2. Allylamine is a highly flammable, colorless liquid. Strong ammonia odor.
3. Allylamine is highly reactive, combining the reactivity of amines with the unsaturation
of the allyl group (Schweizer et al 1978). Reaction with halogens, for
example, gives the corresponding halogenated propylamine in high yield.
Uses
Different sources of media describe the Uses of 107-11-9 differently. You can refer to the following data:
1. In the manufacture of mercurial diuretics.
2. Allylamine ismanufactured fromallyl chloride andammonia.
It is used as a solvent and in organic syntheses, including the
synthesis of rubber, mercurial diuretics, sedatives, and antiseptics
(238). It is also used in the synthesis of ion-exchange
resins.
3. Allylamine is used as an industrial solvent and in organic
synthesis, including rubber vulcanization, synthesis of ionexchange
resins, and as an intermediate in pharmaceutical
synthesis. Derivatives of allylamine are utilized as both veterinary
and human pharmaceuticals, including the antifungal
agent terbinafine. Allylamine has been used since the 1940s as
a research tool for investigations of cardiovascular disease, with
the earliest studies using allylamine to induce initial vascular
injury in animal models of atherogenesis. Additionally, allylamine
has been used to model myocardial infarction and
vascular injury in animal models of human cardiovascular
disease.
Production Methods
Allylamine is produced by reaction of allyl chloride with ammonia. The amine is
also a natural constituent of foodstuffs (Shumkova and Karpova 1981; Mochalov
et al 1981) and is present in wastewater from oil shale retorting (Daughton et al
1985).
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
Different sources of media describe the Health Hazard of 107-11-9 differently. You can refer to the following data:
1. 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.
2. Allylamine is a strong eye and respiratory tract irritant (Windholz et al 1983) and
exposure to it causes transient irritation of mucous membranes of the nose, eye and
mouth with lacrimation, coryza and sneezing (HSDB 1989). Exposure to 14 p.p.m.
allylamine caused intolerable irritation of the eyes and respiratory tract (Grant
1974).
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
Highlyflammable
Industrial uses
Allylamine is used in the synthesis of ion-exchange resins and for water-dispersible
copolymers useful for water purification and as flocculating agents
(Schweizer et al 1978). The amine is also used for the preparation of pharmaceuticals
including 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 intimal
proliferation of vascular smooth muscle cells in multiple
animal species. The mechanism for these distinctive cardiovascular
lesions is believed to be related to its bioactivation to
acrolein and possibly hydrogen peroxide. Several lines of
evidence support this hypothesis; SSAO is highly active in
vascular tissue where allylamine predominantly distributes,
incubation of homogenates of vascular tissue with allylamine
results in the generation of acrolein and hydrogen peroxide,and pretreatment with a semicarbazide inhibitor of SSAO
reduces or eliminates the hypercontraction and vasospasm
associated with allylamine exposure in vitro. Researchers have
taken advantage of the distinctive lesions that result from
various exposures to allylamine and have used it as chemical
tool to induce animal models of cardiovascular dysfunction
that resemble human disease.
Metabolism
The uptake, tissue distribution, excretion and pharmacokinetics of a 450 mg/kg
oral dose of [14C]-allylamine has been studied over a 2 h period in male
Sprague-Dawley rats (Boor 1985). The amine was rapidly absorbed from the
gastrointestinal tract and quickly accumulated and then eliminated from tissues
with 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 in
feces. Allylamine or its metabolites showed an unusual predilection for accumulating
in elastic and muscular arteries with the highest radioactivity (5- to 10-fold
higher than most other organs) occurring in the aorta. Radioactivity in all other
tissues was generally much lower and fairly equal. At 5,10,15 and 20 min after an
i.v. dose of [14C]-allylamine, 30 to 33% of the admitted radioactivity was localized
in the aortas of adult Sprague-Dawley rats. By 30 min, 17% of the administered
dose was still present in that tissue (Hysmith and Boor 1985). Upon differential
centrifugation most of the radioactivity in the aorta was found to be localized in
the mitochondria. Further in vitro investigations (Hysmith and Boor 1987) showed
the specific binding of radioactivity from [14C]-allylamine to isolated rat aorta and
heart mitochondria at both high affinity and low affinity binding sites. As much as
23 and 43% of the bound radioactivity was covalently linked to aorta and heart
mitochondria, respectively. The monoamine oxidase B inhibitor, deprenyl, significantly
reduced both the specific and covalent binding of radioactivity from
[14C]-allylamine in phospholipase treated mitochondria while the benzylamine
oxidase inhibitor, semicarbazide, had no effect on [14C]-allylamine binding. These
results suggest that monoamine oxidase can convert allylamine to a highly reactive
metabolite that selectively covalently binds to heart mitochondria and that this
may explain the cardiotoxicity associated with this amine.
In vitro studies show that allylamine is converted by homogenates of various rat
tissues (heart, aorta, skeletal muscle, lung) to acrolein (Boor et al 1981; Nelson
and Boor 1982). Conversion of allylamine to acrolein in human tissue was 58, 8
and 6% in aorta, myocardium and liver, respectively, while in the rat the
percentages of acrolein formation were 95, 18, 9 and 5% in aorta, lung, skeletal
muscle, and heart preparations, respectively (Boor and Nelson 1982). Purified
bovine plasma amine oxidase and porcine kidney diamine oxidase converted
allylamine to acrolein in vitro (Nelson and Boor 1982). Studies with selective
inhibitors suggested that benzylamine oxidase is the active enzyme in oxidizing
allylamine. Inhibition of benzylamine oxidase with either semicarbazide or
phenelzine protected aortic smooth muscle cells from allylamine-induced cytolethal
injury (Hysmith and Boor 1988). Inhibition of benzylamine oxidase markedly
altered the subcellular distribution of radioactivity from [14C]-allylamine in aortic
smooth muscle cells, with the administered radioactivity no longer being localized
in the mitochondria. The sole urinary metabolite of allylamine in vivo has been
identified as 3-hydroxypropylmercapturic acid (Boor et al 1987; Kage and Young
1972). Parallel experiments showed glutathione (GSH) depletion in several
organs, the most marked occurring in aorta, blood and lung. These findings
indicate that allylamine was metabolized in vivo to the highly reactive aldehyde,
acrolein, which was subsequently converted to a mercapturic acid through a GSH
conjugation 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 solvent
may 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 atm
m3 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.
Check Digit Verification of cas no
The CAS Registry Mumber 107-11-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 7 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 107-11:
(5*1)+(4*0)+(3*7)+(2*1)+(1*1)=29
29 % 10 = 9
So 107-11-9 is a valid CAS Registry Number.
InChI:InChI=1/C3H7N/c1-3(2)4/h1,4H2,2H3
107-11-9Relevant articles and documents
Inter- and intramolecular isotopic correlations in some cyanogenic glycosides and glucosinolates and their practical importance
Butzenlechner, Maria,Thimet, Susanne,Kempe, Klaus,Kexel, Hugo,Schmidt, Hanns-Ludwig
, p. 585 - 592 (1996)
Sinalbin is a complex organic salt from white mustard. The δ 13C- values of the aromatic parts of the anion glucosinalbin (p- hydroxyphenylacetic acid) and of the cation sinapin (sinapic acid) are identical (-32.2‰) and both aromatic compounds are depleted by 6.4‰ with respect to the glucose moiety (-25.8‰) bound in glucosinalbin. The δ 13C value of the choline part of the molecule can be correlated to its metabolic origin from glucose. However, there is an unexpected dramatic 13C- enrichment in the first C atom of glucosinalbin, originally the C-2 of tyrosine. This enrichment of approximately 11% relative to the mean value of the aglycone is found in the same position of four other glucosinolates and cyanogenic glycosides derived from phenylalanine or tyrosine. An isotope effect on the phenylalanine-ammonia-lyase reaction is discussed as the most probable cause for this finding. In contrast, sinigrin, the glucosinolate from black mustard, shows a relative 13C-depletion of 6.5‰ in the corresponding first C-atom of the aglycone allyl mustard oil. The proposed reason for this depletion is an isotope effect on an aldol reaction during the biosynthetic introduction of this C-atom into the aglycone skeleton. Synthetic allyl mustard oil is depleted by 14% in the same position relative to the δ 13C-value of the whole molecule, probably owing to an isotope effect on the first step of its chemical synthesis, the binding of allyl amine to CS2. This difference can be used to detect adulterations of mustard.
METHOD FOR PRODUCING PRIMARY AMINES
-
Paragraph 0047; 0050, (2019/08/27)
PROBLEM TO BE SOLVED: To provide a method for producing primary amines industrially, economically, safely, and efficiently. SOLUTION: Provided is a method for producing primary amines represented by R1-NH2 by reacting, in the presence of an acid catalyst, an imine compound, represented by formula (1), and an alcohol represented by R4-(OH)n, comprising a step of distilling off the primary amine from a reaction mixture which is in the reaction process. (R1 is an alkyl group or an alkenyl group; R2 is H, an alkyl group, or an aryl group; R3 is an aryl group; R4 is an n-valent hydrocarbon roup; and n is an integer of 1 to 3.) SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT
Spectroscopic Evidence for Aminomethylene (H?C??NH2)—The Simplest Amino Carbene
Eckhardt, André K.,Schreiner, Peter R.
supporting information, p. 5248 - 5252 (2018/03/21)
Although N-heterocyclic carbenes have been well-studied, the simplest aminocarbene, aminomethylene H?C??NH2, has not been spectroscopically identified to date. Herein we report the gas-phase preparation of aminomethylene by high-vacuum flash py
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