102-70-5

Basic information

• Product Name: Triallylamine
• Synonyms: N，N-Di-2-propenyl-2-propen-1-Amine;TAA;TRIALLYLAMINE;tri-2-propenylamine;AMINOTRI-2-PROPENE;(CH2=CHCH2)3N;n,n-di-2-propenyl-2-propen-1-amin;N,N-Diallyl-2-propen-1-amine
• CAS NO: 102-70-5
• Molecular Formula: C₉H₁₅N
• Molecular Weight: 137.22
• EINECS: 203-048-2
• Product Categories: Acyclic;Alkenes;Organic Building Blocks;Building Blocks;Chemical Synthesis;Organic Building Blocks
• Mol File: 102-70-5.mol

Chemical Properties

• Melting Point: -70°C
• Boiling Point: 150-151 °C(lit.)
• Flash Point: 87 °F
• Appearance: dark brown liquid
• Density: 0.79 g/mL at 25 °C(lit.)
• Vapor Density: 4.73 (vs air)
• Vapor Pressure: 90 mm Hg ( 80 °C)
• Refractive Index: n20/D 1.451(lit.)
• Storage Temp.: 2-8°C
• PKA: pK1:8.31(+1) (25°C)
• Water Solubility: 250 g/100 mL
• Stability: Stable. Flammable. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: Triallylamine(CAS DataBase Reference)
• NIST Chemistry Reference: Triallylamine(102-70-5)
• EPA Substance Registry System: Triallylamine(102-70-5)

Safety Data

• Hazard Codes: C
• Statements: 10-20/21/22-34
• Safety Statements: 16-26-36/37/39-45
• RIDADR: UN 2610 3/PG 3
• WGK Germany: 3
• RTECS: XX5950000
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 102-70-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Triallylamine is used as a reagent in organic synthesis for the production of various chemical compounds.
Used in Catalyst and Initiator for Polymer Production:
Triallylamine has been proposed as a catalyst for the production of polyesters and as an initiator for the polymerization of butadiene.
Used in Chemical Reactions:
Triallylamine (TAA) is used in various chemical reactions for the formation of different compounds:
1. In the synthesis of 2-ethyl-3-methylquinolines, TAA reacts with primary aromatic amines in the presence of a ruthenium catalyst.
2. TAA undergoes hydrozirconation followed by transmetalation with germanium tetrachloride to form 1-aza-5-germa-5-chlorobicyclo[3.3.3]undecane, which can react with Grignard or lithium reagents to form the corresponding 5-organo compounds.
3. The cycloaddition of TAA to fluorinated 1,3,4-oxadiazoles affords octahydro-2,7-methanofuro[3,2-c]pyridines.
Chemical Properties:
Triallylamine is a dark brown liquid when exposed to air and light, and it can be detected at 0.5 ppm. It is severely irritating at 75 ppm.

Production Methods

Triallylamine is manufactured using allyl chloride and ammonia under heat and pressure. It is used as a solvent and in organic syntheses.

Air & Water Reactions

Flammable. Insoluble in water.

Reactivity Profile

Triallylamine is a strong reducing agent that reacts violently with oxidizing agents. Corrosive towards Al and Zn [Handling Chemicals Safely 1980 p. 912] . 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

May cause toxic effects if inhaled or ingested/swallowed. Contact with substance may cause severe burns to skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

Fire Hazard

Flammable/combustible material. May be ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

Safety Profile

Poison by skin contact and intraperitoneal routes. Moderately toxic by ingestion and inhalation. An eye and severe skin irritant. Human systemic effects by inhalation: structural or functional changes in trachea or bronchi. Flammable liquid when exposed to heat, flame or oxidlzers. To fight fire, use foam, alcohol foam, fog. When heated to decomposition it emits toxic fumes of NOx. See also AMINES and ALLYL COMPOUNDS.

InChI:InChI=1/C9H15N/c1-4-7-10(8-5-2)9-6-3/h4-6H,1-3,7-9H2

Upstream product

• 6919-32-0 tetraallylammonium bromide 
• 107-11-9 1-amino-2-propene 
• 107-05-1 3-chloroprop-1-ene 
• 151-50-8 potassium cyanide 
• 106-99-0 buta-1,3-diene 
• 124-02-7 diallylamine 
• 106-95-6 allyl bromide 
• 463-49-0 1,2-propanediene 
• 72654-43-4 n-propylammonium N-n-propylcarbamate 
• 616-38-6 carbonic acid dimethyl ester 
• 7664-41-7 ammonia 
• 64-17-5 ethanol 
• 591-87-7 Allyl acetate 

Downstream Products

• 51523-45-6 hexa-N-allyl-N,N'-but-2t-enediyl-di-ammonium; dibromide 
• 24401-39-6 2-methyl-2-phenyl-pentenal 
• 93671-59-1 [(diallylamino)propyl]dimethylphenylsilane 
• 589-09-3 N-allyl-N-phenylamine 
• 27356-52-1 2-ethyl-3-methylquinoline 
• 622-80-0 N-propylaniline 
• 15316-91-3 N-allyl-o-toluidine 
• 124-02-7 diallylamine 
• 4536-12-3 perfluoro-(1,3-dimethylcyclopentane) 
• 1805-22-7 perfluoro(2-methylcyclopentane) 
• 355-68-0 perfluorocyclohexane 
• 355-02-2 perfluoro(methylcyclohexane) 
• 413579-52-9 perfluoro-(N-propyl-3,4-dimethylpyrrolidine) 
• 338-83-0 Perfluorotripropylamine 

Related news

Nitrogen doping of ZnSe with trimethylsilylazide, Triallylamine (cas 102-70-5) or bisditrimethylsilylamidozinc during metalorganic vapour phase epitaxy07/14/2019

Several nitrogen precursors without nitrogen hydrogen bonds were tested to dope ZnSe in a MOVPE process. Bisditrimethylsilylamidozinc (ZnBTM), trimethylsilylazide (TMSiN) and triallylamine (TAN) were used to grow ZnSe:N with ditertiarybutylselenide (DTBSe), diisopropylselenide (DIPSe) and dimeth...detailed

Optical and electrical properties of MOVPE-grown ZnSe:N using Triallylamine (cas 102-70-5) as a nitrogen precursor07/13/2019

Photoluminescence (PL), C-V and I-V characteristics of MOVPE-grown ZnSe:N doped using triallylamine (TAN) have been investigated. In our experiments, the use of TAN as dopant source does and lead to the incorporation of nitrogen into the lattice at the VIII ratio optimized for the growth of undo...detailed

Relevant articles and documents

Dramatic acceleration of the catalytic process of the amination of allyl acetates in the presence of a tetraphosphine/palladium system

The cis,cis,cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane/ [PdCl(C3H5)]2 system catalyses allylic amination in good yields with a very high substrate/catalyst ratio; a turnover number of 680 000 and a turnover frequency of 8125 h-1 can be obtained for the addition of dipropylamine to allyl acetate in the presence of this catalyst.

Palladium-tetraphosphine complex: An efficient catalyst for allylic substitution and Suzuki cross-coupling

A new tetraphosphine, the cis-cis-cis-1,2,3,4-tetrakis (diphenylphosphinomethyl)cyclopentane (Tedicyp) has been synthesized and used in palladium-catalyzed reactions. This tetraphosphine in combination with [Pd(C3H5)Cl]2 affords a very efficient catalyst for coupling reactions. Turnover numbers of 980 000 for allylic amination, 9 800 000 for allylic alkylation and 97 000 000 for Suzuki cross-coupling can be obtained in the presence of this catalyst.

Preparation method of allyl amine mixture

The invention discloses a preparation method of an allyl amine mixture. The preparation method includes following steps: S1, pouring a catalyst into a reation kettle, adding a certain amount of ammonium hydroxide, rising temperature, and adding chloropropene for ammonolysis reaction; S2, holding the temperature of the step 1, and adding liquid caustic soda; S3, rectifying a reaction product to evaporate water and excessive ammonia; S4, at corresponding temperature, collecting fraction-monoallyl amine; S, at corresponding temperature, collecting fraction-diallyl amine; S6, at corresponding temperature, collecting fraction-trially amine; S7, adding caustic soda flakes into a collected fraction mixture, and performing liquid separation to obtain. The preparation method is mild in reaction condition, ammonium hydroxide is used to replace ammonia in existing methods, and complex ventilation equipment is not needed, so that production cost is saved; by adding the caustic soda flakes, water absorbing effect can be realized, purity of the allyl amine mixture prepared by the method can be effectively improved, and the preparation method is simple to operate, high in yield and worthy of popularization.

GOLD CATALYZED HYDROAMINATION OF ALKYNES AND ALLENES

Methods are provided for the catalytic hydroamination of compounds having an alkyne or allene functional group, in which the compound is contacted with ammonia or an amine in the presence of a catalytic amount of a gold complex under conditions sufficient for hydroamination to occur.

Homogeneous catalytic hydroamination of alkynes and allenes with ammonia

(Chemical Equation Presented) A golden ticket to the synthesis of reactive nitrogen-containing compounds, such as imines, enamines, and allyl amines, through the addition of NH3 to unsaturated bonds is the cationic cyclic (alkyl)-(amino)carbene-gold(I) catalyst shown in blue (Dipp=diisopropylphenyl). An ideal initial step for the preparation of simple bulk chemicals, this reaction is also useful for the synthesis of more complex molecules (see examples).

METHOD FOR PRODUCING PRIMARY AMINE COMPOUND

Disclosed is a method for producing a primary amine compound represented by the formula (2) below, which is characterized in that a halogen compound represented by the formula (1) below, ammonia and formaldehyde are reacted with each other, and then the thus-obtained reaction product is [1] brought into contact with an aqueous solution of an acid or [2] reacted with a hydroxylamine under acidic conditions. By this method, a primary amine compound can be commercially advantageously produced by using a low-cost ammonia while suppressing production of a secondary amine as a by-product. (1) (In the formula, R1 and R2 independently represent a hydrogen atom, a C1-C5 alkyl group which may be substituted by a halogen atom or the like, a C1-C5 alkoxy group which may be substituted by a halogen atom, a cyano group, a C2-C11 alkenyl group or a phenyl group or the like; R3 represents a hydrogen atom, a linear or branched C1-C5 alkyl group or a cyano group; and X represents a halogen atom.) (2) (In the formula, R1, R2 and R3 are as defined above.)

Mechanistic Studies on the Role of Carbon Dioxide in the Synthesis of Methylcarbamates from Amines and Dimethylcarbonate in the Presence of CO2

N-Alkylmethylcarbamates have been synthesized from amines and dimethylcarbonate (DMC) in the presence of carbon dioxide.The catalytic role of CO2 in the overall process has been investigated and elucidated.Key words: carbon dioxide; organic carbamates; dimethylcarbonate; carbamic-carbonic anhydride