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Sigma-Aldrich

3-(Dimethylamino)-1-propylamine

purum, ≥98.0% (GC)

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Synonym(s):
N,N-Dimethyl-1,3-diaminopropane, N,N-Dimethyl-1,3-propanediamine
Linear Formula:
(CH3)2N(CH2)3NH2
CAS Number:
109-55-7
Molecular Weight:
102.18
Beilstein:
605293
EC Number:
203-680-9
MDL number:
MFCD00008216
PubChem Substance ID:
329755864
NACRES:
NA.22

vapor density

3.6 (vs air)

Quality Level

200

vapor pressure

5 mmHg ( 20 °C)

grade

purum

Assay

≥98.0% (GC)

form

liquid

impurities

≤2% water

refractive index

n20/D 1.435 (lit.)
n20/D 1.436

bp

133 °C (lit.)

density

0.812 g/mL at 25 °C (lit.)

SMILES string

CN(C)CCCN

InChI

1S/C5H14N2/c1-7(2)5-3-4-6/h3-6H2,1-2H3

InChI key

IUNMPGNGSSIWFP-UHFFFAOYSA-N

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General description

3-(Dimethylamino)-1-propylamine (DMAPA, N,N-dimethyl-1,3-propanediamine) is a dialkylamino alkyl amine. It has been prepared from dimethylamine and acrylonitrile and confirmed by 1H NMR. It participates in the synthesis of bio-based zwitterionic surfactants from waste cooking oil (WCO).

Application

3-(Dimethylamino)-1-propylamine (DMAPA) is suitable reagent used in the following studies:
  • As a cationic moiety to form the ionic liquid, 3-(dimethylamino)-1-propylaminium formate ([DMAPA]FA) which is a potential reagent to extract protein from yeast cells.
  • As an aminating agent in the palladium-catalyzed amination of aryl amines.
  • In the derivatization of pullulan to form cationic pullulan.
  • In the partial modification of poly(styrene-alt-maleic anhydride) to form N-substituted maleimide.
  • As a test compound in the parallel synthesis of alkylamine lipidoids.
  • To cleave the polyamides synthesized by solid phase methods on Boc-β-Ala-PAM resin.
It may be used in the following studies:
  • Synthesis of (N,N-dialkylamino)alkyl-2-amino benzamide by reacting with isatoic anhydride.
  • As a reagent for the anomeric deacetylation of protected sugars.
  • Preparation of bioreducible copolymers used in gene delivery.

Other Notes

Industrial applications

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

89.6 °F - closed cup

Flash Point(C)

32 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

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Liya Ge et al.
Talanta, 81(4-5), 1861-1864 (2010-05-06)
As the first attempt, ionic liquid solutions have been employed for direct extraction of proteins from yeast cells. Compared with effects of 21 different ionic liquid solutions on the extraction efficiency, 3-(dimethylamino)-1-propylaminium formate ([DMAPA]FA) was selected as the suitable ionic
A Comprehensive Mechanism for Aromatic Nucleophilic Substitution in Aprotic Solvents: Derivation of the Whole Reaction Scheme for Third Order in Amine Kinetic Law.
Alvaro CE, et al.
Physical Chemistry, 3(2), 39-47 (2013)
Carey F Hsu et al.
Tetrahedron, 63(27), 6146-6151 (2008-07-04)
Hairpin pyrrole-imidazole (Py-Im) polyamides are programmable oligomers that bind the DNA minor groove in a sequence-specific manner with affinities comparable to those of natural DNA-binding proteins. These cell-permeable small molecules have been shown to enter the nuclei of live cells
Linxian Li et al.
Bioconjugate chemistry, 24(9), 1543-1551 (2013-08-06)
Efficient delivery of plasmid DNA and siRNA into cells is essential for biological and biomedical research. Although significant efforts have been made to develop efficient nonviral vectors, such as cationic lipids and polymers, most of the vectors require multistep synthesis
Exploring the potential of xanthene derivatives as trypanothione reductase inhibitors and chloroquine potentiating agents.
Chibale K, et al
Tetrahedron, 59(13), 2289-2296 (2003)
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