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T45004

Sigma-Aldrich

Triallylamine

99%

Synonym(s):

TAA

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About This Item

Linear Formula:
(H2C=CHCH2)3N
CAS Number:
102-70-5
Molecular Weight:
137.22
EC Number:
203-048-2
MDL number:
MFCD00026093
UNSPSC Code:
12352100
PubChem Substance ID:
24900211
NACRES:
NA.22

vapor density

4.73 (vs air)

Quality Level

200

vapor pressure

90 mmHg ( 80 °C)

Assay

99%

refractive index

n20/D 1.451 (lit.)

bp

150-151 °C (lit.)

density

0.79 g/mL at 25 °C (lit.)

SMILES string

C=CCN(CC=C)CC=C

InChI

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

InChI key

VPYJNCGUESNPMV-UHFFFAOYSA-N

Related Categories

Application

  • Triallylamine (TAA) reacts with primary aromatic amines in the presence of a ruthenium catalyst to form 2-ethyl-3-methylquinolines.
  • TAA undergoes hydrozirconation followed by transmetalation with germanium tetrachloride to form 1-aza-5-germa-5-chlorobicyclo[3.3.3]undecane. This compound can react with Grignard or lithium reagents to form the corresponding 5-organo compounds.
  • The cycloaddition of TAA to fluorinated 1,3,4-oxadiazoles affords octahydro-2,7-methanofuro[3,2-c]pyridines.

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Flam. Liq. 3 - Skin Corr. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

87.8 °F - closed cup

Flash Point(C)

31 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW3203
MKCW5562
MKCX0079
MKCV2237
MKCT9110

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Ruthenium-catalyzed synthesis of 2-ethyl-3-methylquinolines from anilines and triallylamine.?
Cho C H, et al.
Tetrahedron Letters, 40(8), 1499-1500 (1999)
Palladium-catalyzed reaction of 1-aza-5-germa-5-organobicyclo [3.3. 3] undecane with aryl bromide.
Kosugi M, et al.
Journal of Organometallic Chemistry, 508(1-2), 255-257 (1996)
E D Thompson et al.
Environmental and molecular mutagenesis, 18(3), 184-199 (1991-01-01)
Three cross-linked polyacrylate polymers containing either methylenebis-acrylamide (MBA), trimethylolpropane triacrylate (TMPTA), or triallylamine (TAA) cross-linkers were tested for genotoxicity with the Salmonella mammalian microsome assay, the L5178Y mouse lymphoma TK +/- assay, the unscheduled DNA synthesis assay in primary cultures
H G Swarts et al.
Biochimica et biophysica acta, 1189(2), 143-151 (1994-01-19)
Tertiary amines like imidazole and triallylamine lower the apparent affinity of K+ in the ATP hydrolysis reaction of pig gastric H,K-ATPase in a pH and amine concentration dependent way. The mechanism and sidedness of this effect was studied by analyzing
Cycloaddition of fluorinated oxadiazoles with triallylamine.
Vasil?ev N V, et al.
Chemistry of Heterocyclic Compounds, 52(9), 750-752 (2016)
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