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39380

Sigma-Aldrich

3-(Dimethylamino)-1-propylamine

purum, ≥98.0% (GC)

Synonym(s):

N,N-Dimethyl-1,3-diaminopropane, N,N-Dimethyl-1,3-propanediamine

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About This Item

Linear Formula:
(CH3)2N(CH2)3NH2
CAS Number:
Molecular Weight:
102.18
Beilstein:
605293
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

vapor density

3.6 (vs air)

Quality Level

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

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Exploring the potential of xanthene derivatives as trypanothione reductase inhibitors and chloroquine potentiating agents.
Chibale K, et al
Tetrahedron, 59(13), 2289-2296 (2003)
New antihistaminic agents: Synthesis and evaluation of h 1-antihistaminic actions of 3-[(N,N-dialkylamino) alkyl)-1, 2, 3, 4-tetrahydro-(1H)-thioquinazolin-4 (3H)-ones and their oxo analogues.
Raju MB, et al
Indian Journal of Pharmaceutical Sciences, 69(6), 853-853 (2007)
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)
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
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

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