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]

Not to be confused with N,N′-Dimethyl-1,3-propanediamine.
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
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.003.347
EC Number
  • 203-680-9
MeSH 3-dimethylaminopropylamine
RTECS number
  • TX7525000
UNII
UN number 2733
  • InChI=1S/C5H14N2/c1-7(2)5-3-4-6/h3-6H2,1-2H3 checkY
    Key: IUNMPGNGSSIWFP-UHFFFAOYSA-N checkY
  • CN(C)CCCN
Properties
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
1.435–1.436
Thermochemistry
255.7 J K−1 mol−1
323.0 J K−1 mol−1
−76.9–−76.9 kJ mol−1
−3.8955–−3.8875 MJ mol−1
Hazards
GHS labelling:
GHS02: Flammable GHS05: Corrosive GHS07: Exclamation mark
Danger
H226, H302, H314, H317
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):
  • 487 mg kg−1 (dermal, rabbit)
  • 1.87 g kg−1 (oral, rat)
Related compounds
Related amines
Related compounds
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

References
  1. "BASF ups capacity at DMAPA plant". Cosmetics Design. 2003-10-28.
  2. 3-Aminopropyldimethylamine (PDF). {{cite book}}: |work= ignored (help)
  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. PMID 7758328.
  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.
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