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EC / List no.: 203-463-9
CAS no.: 107-11-9
Mol. formula: C3H7N
Allylamine is an organic compound with the formula C3H5NH2.
This colorless liquid is the simplest stable unsaturated amine.
Allylamine appears as a colorless to light yellow colored liquid with a strong ammonia-like odor.
Less dense than water.
Vapors are heavier than air.
Flash point below 0°F.
Boiling point 130°F.
Used to make pharmaceuticals and other chemicals.
Production and reactions
All three allylamines, mono-, di-, and triallylamine, are produced by the treating allyl chloride with ammonia followed by distillation.
Or by the reaction of allyl chloride with Hexamine.
Pure samples can be prepared by hydrolysis of allyl isothiocyanate.
Allylamine behaves as a typical amine.
Polymerization can be used to prepare the homopolymer (polyallylamine) or copolymers.
The polymers are promising membranes for use in reverse osmosis.
Other allylamines
Functionalized allylamines have extensive pharmaceutical applications.
Pharmaceutically important allylamines include flunarizine and naftifine.
Flunarizine aids in the relief of migraines while naftifine acts to fight common fungus causing infections such as athlete's foot, jock itch, and ringworm.
Uses:
In the manufacture of mercurial diuretics.
Pharmaceutical intermediate; organic synthesis
Allylamine is used as a solvent and in organic synthesis, including the synthesis of rubber, mercurial diuretics, sedatives, and antiseptics.
Allylamine is also used in the synthesis of ion-exchange resins.
Synthesis of ion-exchange resins and for water-dispersible copolymers useful for water purification and as flocculating agents.
Allylamine is useful as a corrosion inhibitor when pickling steel in acid.
Industry Uses
Intermediates
Pharmaceuticals
Surface active agents
Consumer Uses
Agricultural products (non-pesticidal)
Chemical Manufacturing
Non-TSCA use
Methods of Manufacturing
Pure allylamine can be prepared by hydrolysis of allyl isothiocyanate, thermal cleavage of allyl dithiocarbamate, hydrolysis of diallyl cyanamide, or ammonolysis of triallylamine.
Allylamine may be produced also by electroreduction of acrylonitrile on lead cathodes.
Allylamine can be synthesized by reaction of allyl chloride with ammonia at the comparatively high temperature of 50-100 °C, or at lower temperatures using CuCl2 or CuCl as the catalyst.
In all such methods, a mixture of monoallyl, diallyl, and triallyl amines is obtained.
For selectively obtaining monoallylamine, AAm, hydrolysis of by hydrochloric acid is used.
The oldest technology for producing amines is the reaction of ammonia with an alkyl halide. This method is still of commercial importance for the manufacture of allylamines.
Allylamine is produced by reaction of allyl chloride with ammonia. The amine is also a natural constituent of foodstuffs and is present in wastewater from oil shale retorting.
General Manufacturing Information
Industry Processing Sectors
All other basic organic chemical manufacturing
Pesticide, fertilizer, and other agricultural chemical manufacturing
Pharmaceutical and medicine manufacturing
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
colourless liquid
Allylamine is a highly flammable, colorless liquid.
Strong ammonia odor.
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:
In the manufacture of mercurial diuretics.
Allylamine ismanufactured fromallyl chloride andammonia.
Allylamine is used as a solvent and in organic syntheses, including the synthesis of rubber, mercurial diuretics, sedatives, and antiseptics (238).
Allylamine is also used in the synthesis of ion-exchange resins.
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 and is present in wastewater from oil shale retorting.
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.
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.
The amine is also used for the preparation of pharmaceuticals including mercurial diuretics and antifungal agents.
Allylamine can be used:
To prepare a chemical gradient through plasma co-polymerization of octadiene and allylamine polymer on nanoporous alumina.
As a monomer to prepare plasma polymerized allylamine films in the study of their reactivity on Au and Si.
In a direct monocarboxymethylation reaction to yield N-formyl glycine derivatives.
Uses:
Allylamine is used as an industrial solvent and in organic synthesis, including rubber vulcanization, synthesis of ion-exchange 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.
1. Allylamine is desirable to use a gas trap in order to prevent vapors of allyl isothiocyanate from escaping into the room. The gas trap described on p. 4 is suitable.
2. Eastman's "practical" grade (b.p. 150–152°) of allyl isothiocyanate was used in this preparation.
3. The rate of evaporation is greatly accelerated by allowing a stream of air to blow across the surface of the hot liquid. Allylamine is advantageous for the evaporation to proceed as far as possible in order to remove most of the free hydrochloric acid, and no harm is done if Allylamine continues until the solution turns to a semi-solid mass of crystals.
4. Care must be taken throughout to prevent loss of the product by volatilization. Furthermore, the vapors should not be allowed to come into contact with the nasal passages, as violent sneezing is produced.
5. The distillate should be kept cold (5–10°) during the drying process and should be separated from the potassium hydroxide before drying with sodium.
Formula
C3H7N
Formula Weight
57.10
Melting point
-88°
Boiling Point
53-54°
Flash Point
-28°(-18°F)
Density
0.761
Refractive Index
1.4210
Storage & Sensitivity
Air Sensitive. Ambient temperatures.
Solubility
Fully miscible in water.
Allylamine is used as monomer in deposition of the allylamine plasma polymer.
Allylamine was used in generation of a chemical gradient via plasma co-polymerization of octadiene and allylamine polymer on nanoporous alumina.
Allylamine was used to investigate the surface reactivity of substrates coated with thin layers of plasma polymerized allylamine films.
Allylamine was used in a direct monocarboxymethylation reaction.
Allylamine is a liquid and stable organic compound.
Allylamine is the simplest unsaturated Amine.
The International Union of Pure and Applied Chemistry (IUPAC) named this compound as 3-Amino-prop-1-ene.
Producing Allylamine
Allyl Chloride is treated with Ammonia in order to produce Allylamine.
This treatment is followed by the process of distillation.
Pure samples are synthesized by the Hydrolysis of Allyl Isothiocyanate.
The behavior of this chemical is typical to Amines.
hysical and Chemical Properties of Allylamine
Following are some of the basic properties of Allylamine.
Appearance: Allylamine is a colorless liquid.
Odor: This compound has a sharp odor that resembles Ammonia.
Solubility: Allylamine has high solubility in water.
Molar Mass: The molar mass of Allylamine is 57.09 g/mol.
Specific Gravity: Allylamine has the specific gravity of 0.761.
Melting Point: The melting point of this compound is -88 °C (-126 °F).
Boiling Point: Boiling point of Allylamine is somewhere between 55-58 °C (131-136 °F).
Density: The density of this liquid substance is 0.7630 g/cm3.
Vapor Pressure: Its vapor pressure is 32.3 kPa at 25 °C temperature.
Allylamine Structure
The formula of this compound can also be denoted as CH2=CHCH2NH2.
There are three Carbon atoms in one molecule of this Amine.
Carbon atoms have four valence electrons so Allylamine can create four covalent bonds.
Two of the three Carbons create a double bond (a bond involving four bonding electrons) between themselves.
Five of the total seven Hydrogen atoms create single bonds with Carbons.
Nitrogen has three valence electrons and creates a single bond with the last remaining valence of Carbon.
The two remaining Hydrogen atoms create bonds with the two other valence electrons of Nitrogen.
Applications of Allylamine
This simplest and stable Amine has various uses.
Industrial Uses
Allylamine is used as a chemical solvent in different industries.
Medical Uses
Allylamine is used as antifungal medicine for the treatment of skin and scull ringworm.
Cream or pills made from this compound are used for this purpose.
The creams do not have any side effects; however, the pills may cause headaches and stomach problems.
Allylamine is also used as a medicine for the skin disease “Athlete’s Foot”.
This Amine is used to make antibiotic, diuretic and sedative medicines.
About Allylamine
Helpful information
Allylamine is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 100 to < 1 000 tonnes per annum.
Allylamine is used by professional workers (widespread uses), in formulation or re-packing and at industrial sites.
Consumer Uses
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. ECHA has no public registered data on the routes by which Allylamine is most likely to be released to the environment.
Article service life
ECHA has no public registered data on the routes by which Allylamine is most likely to be released to the environment. ECHA has no public registered data indicating whether or into which articles the substance might have been processed.
Widespread uses by professional workers
Allylamine is used in the following products: pH regulators and water treatment products and laboratory chemicals.
Allylamine is used in the following areas: health services and scientific research and development.
Other release to the environment of Allylamine is likely to occur from: indoor use (e.g. machine wash liquids/detergents, automotive care products, paints and coating or adhesives, fragrances and air fresheners).
Formulation or re-packing
ECHA has no public registered data indicating whether or in which chemical products the substance might be used. Release to the environment of Allylamine can occur from industrial use: formulation of mixtures.
Uses at industrial sites
Allylamine is used in the following products: pharmaceuticals, pH regulators and water treatment products and laboratory chemicals.
Allylamine is used in the following areas: health services and scientific research and development.
Allylamine is used for the manufacture of: chemicals and plastic products.
Release to the environment of Allylamine can occur from industrial use: for thermoplastic manufacture, as an intermediate step in further manufacturing of another substance (use of intermediates), in processing aids at industrial sites and as processing aid.
Manufacture
ECHA has no public registered data on the routes by which Allylamine is most likely to be released to the environment.
Allylamine is a pungent strongly basic liquid C3H7N used in the synthesis of some pharmaceuticals (as mercurial diuretics)
Allylamine is a functional monomer-amine monomer.
It has a purity of 99.5% minimum with a water content of 0.50% maximum.
Allylamine is well suited for use in coatings.
The allylamines are a new class of antifungal drugs that inhibit ergosterol synthesis at the level of squalene epoxidase.
These agents are highly selective for the fungal enzyme and have a minimal effect on mammalian cholesterol synthesis.
Naftifine, the original member of the allylamine series, possesses only topical activity, whereas the naftifine analog terbinafine is active both topically and orally.
In vitro, terbinafine is exceptionally active against dermatophytes, molds, and dimorphic fungi in which it exerts a fungicidal action.
This in vitro profile is reflected by the clinical effectiveness of this allylamine in the treatment of dermatophyte infections.
When given orally, terbinafine is well absorbed and rapidly and extensively distributed to the skin and sebum in concentrations that exceed the minimum inhibitory concentrations of these organisms by several orders of magnitude.
Allylamines (eg, naftifine, terbinafine) and the related benzylamine butenafine inhibit squalene epoxidase, which converts squalene to ergosterol.
Inhibition of this enzyme causes squalene, a substance toxic to fungal cells, to accumulate intracellularly and leads to rapid cell death.
Allylamines bind effectively to the stratum corneum because of their lipophilic nature. They also penetrate deeply into hair follicles.
Allylamine is used as intermediates of pharmaceutical chemicals, agricultural chemicals, dyes and coatings, organic synthesis and resin conditioner.
Allylamine can also be used to prepare amphoteric polymer.
Allylamine CAS 107-11-9
CAS Number: 107-11-9
Usage: Pharmaceutical Intermediates
Molecular Formula: C3H7N
Molecular Weight: 57.09
EINECS: 203-463-9
Density: 0.763
Melting Point: -88 C
Boiling Point: 58 C
Flash Point: -29 C
Solubility: miscible
Risk Codes: R11; R23/24/25; R51/53 Details
Appearance: light yellow liquid
liansport Information:140kgs
Hazard Symbols: 6.1 (Packing group: I)
Stability
Stability Air sensitive.
Serious fire hazard.
Highly flammable - note low flash point.
May be ignited at temperatures close to ambient.
IUPAC NAMES:
2-Propen-1-amine
2-propene-1-ylamine
3-Aminopropen
Allylamin
Allylamine
allylamine
Allylamine
allylamine
prop-2-en-1-amine
SYNONYMS:
ALLYLAMINE
2-Propen-1-amine
107-11-9
prop-2-en-1-amine
Monoallylamine
3-Aminopropene
3-Aminopropylene
3-Amino-1-propene
2-Propenamine
2-Propenylamine
Allyl Amine
Polyallylamine
NSC 7600
Allylamine, 98%
2-Propen-1-ylamine
UNII-48G762T011
30551-89-4
MFCD00008199
48G762T011
Poly(allylamine)
allylaminehydrochloride
allylamin
Allylamine, polymers
Allylamine homopolymer
CCRIS 4746
HSDB 2065
PAA-L
2-Propenamine homopolymer
EINECS 203-463-9
PAA 1LV
UN2334
ailylamine
BRN 0635703
PAA 10C
PAA 10L
allyl-amine
N-allylarnine
N-allylamine
AI3-23214
2-propenyl amine
(2-propenyl)amine
1-amino-2-propene
PubChem19133
Allylamine, >=99%
Poly(allylamine) solution
CH2=CHCH2NH2
EC 203-463-9
4-04-00-01057 (Beilstein Handbook Reference)
WLN: Z2U1
Allylamine;3-amino-1-propene
CHEMBL57286
2-Propen-1-amine, homopolymer
DTXSID8024440
NSC7600
Allylamine [UN2334] [Poison]
BCP27099
NSC-7600
STR00193
BDBM50225454
CP0091
STL185583
ZINC17654097
AKOS000119634
Allylamine, purum, >=98.0% (GC)
MCULE-2424616806
UN 2334
Allylamine, puriss., >=99.5% (GC)
1-Aminoprop-2-ene
2-Propen-1-ylamin
2-Propene-1-amine
2-Propenylamine
Allylamin
CH2=CHCH2NH2
3-Aminopropen
3-Aminopropylene
Allylamine, extra pure
Propene-3-amine
ALLYLAMINE FOR SYNTHESIS 250 ML
ALLYLAMINE FOR SYNTHESIS 1 L
2-propeneamine
Allylamine,98+%,extra pure
allylaMate
ColesevelaM IMpurity (AllylaMine)
AllyaMine
AllylaMine, 98%, SpcSeal
3-Amino-1-propene,Allylamine
Allylamine (L-phenylalanine alcohol)
prop-2-enylamine
2-Propenamine
2-PROPEN-1-AMINE
2-PROPEN-1-YLAMINE
3-AMINOPROPENE
3-AMINO-1-PROPENE
AA
ALLYLAMINE
MONOALLYLAMINE
ALLYLAMINE, 99+%
Allylamine, 98% (3-Amino-1-propene)
Allylamine, extra pure, 98+%
ALLYALMINE ( MONALLYAMINE )
Allylamine, 98+%
2-Propen-1-ylamine, 3-Amino-1-propene
XBA
