Dimethylaminopropylamine

Not to be confused with N,N′-Dimethyl-1,3-propanediamine.

Dimethylaminopropylamine (DMAPA) is a diamine used in the preparation of some surfactants, such as cocamidopropyl betaine which is an ingredient in many personal care products including soaps, shampoos, and cosmetics. BASF, a major producer, claims that DMAPA-derivatives do not sting the eyes and makes a fine-bubble foam, making it appropriate in shampoos.^[1]

Dimethylaminopropylamine

Skeletal formula of dimethylaminopropylamine
Names
Preferred IUPAC name N1,N1-Dimethylpropane-1,3-diamine
Other names 3-(Dimethylamino)-1-propylamine 3-Dimethylaminopropylamine N,N-Dimethyl-1,3-propanediamine
Identifiers
CAS Number	109-55-7 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1232234 N
ChemSpider	7703 Y
ECHA InfoCard	100.003.347
EC Number	203-680-9
MeSH	3-dimethylaminopropylamine
PubChem CID	7993
RTECS number	TX7525000
UNII	I98I2UEC03 Y
UN number	2733
CompTox Dashboard (EPA)	DTXSID5025102
InChI InChI=1S/C5H14N2/c1-7(2)5-3-4-6/h3-6H2,1-2H3 Y Key: IUNMPGNGSSIWFP-UHFFFAOYSA-N Y
SMILES CN(C)CCCN
Properties
Chemical formula	C5H14N2
Molar mass	102.181 g·mol−1
Appearance	Colourless liquid
Odor	fishy, ammoniacal
Density	812 mg mL−1
Boiling point	132.1 °C; 269.7 °F; 405.2 K
log P	−0.211
Vapor pressure	0.7–2.4 kPa
Refractive index (nD)	1.435–1.436
Thermochemistry
Heat capacity (C)	255.7 J K−1 mol−1
Std molar entropy (S⦵298)	323.0 J K−1 mol−1
Std enthalpy of formation (ΔfH⦵298)	−76.9–−76.9 kJ mol−1
Std enthalpy of combustion (ΔcH⦵298)	−3.8955–−3.8875 MJ mol−1
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H302, H314, H317
Precautionary statements	P280, P305+P351+P338, P310
Flash point	32 °C (90 °F; 305 K)
Explosive limits	2.3–12.36%
Lethal dose or concentration (LD, LC):
LD50 (median dose)	487 mg kg−1 (dermal, rabbit) 1.87 g kg−1 (oral, rat)
Related compounds
Related amines	Dimethylamine Trimethylamine N-Nitrosodimethylamine Diethylamine Triethylamine Diisopropylamine Diethylenetriamine N,N-Diisopropylethylamine Triisopropylamine Tris(2-aminoethyl)amine Mechlorethamine HN1 (nitrogen mustard) HN3 (nitrogen mustard)
Related compounds	Unsymmetrical dimethylhydrazine Biguanide Dithiobiuret Agmatine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Preparation and reactions

DMAPA is commonly produced commercially via the reaction between dimethylamine and acrylonitrile (a Michael reaction) to produce dimethylaminopropionitrile. A subsequent hydrogenation step yields DMAPA:^[2]

DMAPA is readily converted to the mustard dimethylaminopropyl-3-chloride, a powerful alkylating agent.^[3]

Health effects

Dimethylaminopropylamine is a known skin irritant and its presence as an impurity in cocamidopropyl betaine is thought to be the cause of irritation experienced by some individuals.^[4][5]

See also

• 1,1-Dimethylethylenediamine
• 1,2-Dimethylethylenediamine