Dimethylaminopropylamine

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

Names
Preferred IUPAC name N^1,N^1-dimethylpropane-1,3-diamine
Systematic IUPAC name N,N-Dimethyl-1,3-diaminopropane
Other names 3-(Dimethylamino)-1-propylamine 3-Dimethylaminopropylamine N,N-Dimethyl-1,3-propanediamine
Identifiers
CAS Number	109-55-7
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1232234
ChemSpider	7703
ECHA InfoCard	100.003.347
EC Number	203-680-9
MeSH	3-dimethylaminopropylamine
PubChem CID	7993
RTECS number	TX7525000
UNII	I98I2UEC03
UN number	2733
CompTox Dashboard (EPA)	DTXSID5025102
InChI InChI=1S/C5H14N2/c1-7(2)5-3-4-6/h3-6H2,1-2H3 Key: IUNMPGNGSSIWFP-UHFFFAOYSA-N
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^o298)	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 pictograms
GHS Signal word	Danger
GHS hazard statements	H226, H302, H314, H317
GHS precautionary statements	P280, P305+351+338, 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).
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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

References

1. "BASF ups capacity at DMAPA plant". Cosmetics Design. 2003-10-28.
2. 3-Aminopropyldimethylamine (PDF). OECD Screening Information Dataset. UN Environment.
3. Loeliger, P.; Flückiger, E. (1976). "Sulfide Contraction via Alkylative Coupling: 3-Methyl-2,4-Hepthanedione". Organic Syntheses. 55: 127. doi:10.15227/orgsyn.055.0127.
4. Angelini, Gianni; Foti, Caterina; Rigano, Luigi; Vena, Gino A. (February 1995). "3-Dimethylaminopropylamine: a key substance in contact allergy to cocamidopropylbetaine?". Contact Dermatitis. 32 (2): 96–99. doi:10.1111/j.1600-0536.1995.tb00754.x.
5. PIGATTO, P (March 1995). "Contact dermatitis to cocamidopropylbetaine is caused by residual amines: Relevance, clinical characteristics, and review of the literature". American Journal of Contact Dermatitis. 6 (1): 13–16. doi:10.1016/1046-199X(95)90062-4.