Diisopropylamine

Title: Diisopropylamine
CAS Registry Number: 108-18-9
CAS Name: N-(1-Methylethyl)-2-propanamine
Molecular Formula: C6H15N
Molecular Weight: 101.19
Percent Composition: C 71.22%, H 14.94%, N 13.84%
Line Formula: [(CH3)2CH]2NH
Literature References: Prepn: A. Siersch, Ann. 148, 263 (1868); M. Van der Zande, Rec. Trav. Chim. 8, 202 (1889). Enthalpy of formation: M. A. V. Ribeiro da Silva et al., J. Chem. Thermodyn. 29, 1025 (1997). Toxicity study: H. F. Smyth et al., Arch. Ind. Hyg. Occup. Med. 10, 61 (1954). Safety assessment: J. Am. Coll. Toxicol. 14, 182-192 (1995).
Properties: Liquid; characteristic odor; strongly alkaline. d22 0.722. bp 84°. Flash pt, open cup: 21°F (-6°C). Sol in water, alc. LD50 orally in rats: 0.77 g/kg (Smyth).
Boiling point: bp 84°
Flash point: Flash pt, open cup: 21°F (-6°C)
Density: d22 0.722
Toxicity data: LD50 orally in rats: 0.77 g/kg (Smyth)
Derivative Type: Lithium salt
CAS Registry Number: 4111-54-0
Additional Names: LDA; lithiodiisopropylamine; lithium diisopropylamide
Literature References: Strong nucleophile. Crystal structure: N. D. R. Barnett et al. J. Am. Chem. Soc. 113, 8187 (1991). Use as nucleophile: Y. Tanaka et al., Bull. Chem. Soc. Jpn. 60, 788 (1987); S. Saito et al., J. Am. Chem. Soc. 119, 611 (1997). Review of chemistry: Reagents for Organic Synthesis vol. 8, M. Fieser, Ed. (Wiley-Interscience, New York, 1980) pp 292-299.
Properties: Powder, melts with decompn. Air and moisture sensitive.
CAUTION: Potential symptoms of overexposure are irritation of eyes, skin and respiratory system; nausea, vomiting; headache; visual disturbance. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 110.
Use: pH adjuster in colognes and toilet waters. In organic synthesis, particularly, the lithium salt.
Diisopropylamine Dichloroacetate Dikegulac Dilazep Diloxanide Diltiazem

Diisopropylamine
Skeletal formula of diisopropylamine
Identifiers
Abbreviations DIPA
CAS number 108-18-9 YesY
PubChem 7912
ChemSpider 7624 YesY
UNII BR9JLI40NO YesY
EC number 203-558-5
UN number 1158
RTECS number IM4025000
Beilstein Reference 605284
Jmol-3D images Image 1
Properties
Molecular formula C6H15N
Molar mass 101.19 g mol−1
Appearance Colorless liquid
Odor Fishy, ammoniacal
Density 0.722 g mL−1
Melting point −61.00 °C; −77.80 °F; 212.15 K
Boiling point 83 to 85 °C; 181 to 185 °F; 356 to 358 K
Vapor pressure 6.7 kPa (at 20 °C)
Acidity (pKa) 40
Basicity (pKb) 54
Refractive index (nD) 1.392–1.393
Thermochemistry
Std enthalpy of
formation ΔfHo298
−173.6–−168.4 kJ mol−1
Std enthalpy of
combustion ΔcHo298
−4.3363–−4.3313 MJ mol−1
Hazards
GHS pictograms The flame pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The corrosion pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
GHS hazard statements H225, H302, H314, H332
GHS precautionary statements P210, P280, P305+351+338, P310
EU Index 612-129-00-5
EU classification Flammable F Corrosive C
R-phrases R11, R20/22, R34
S-phrases (S1/2), S16, S26, S36/37/39
NFPA 704
NFPA 704.svg
3
2
0
Flash point −17 °C; 1 °F; 256 K
Autoignition temperature 315 °C; 599 °F; 588 K
Explosive limits 1.1–8.5%
LD50
  • 770 mg kg−1 (oral, rat)
  • >10 g kg−1 (dermal, rabbit)
Related compounds
Related amines
  • Dimethylamine
  • Diethylamine
Related compounds
  • Triisopropylamine
  • N,N-Diisopropylethylamine
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Diisopropylamine is a secondary amine with the chemical formula (CH3)2HC-NH-CH(CH3)2. It is best known as its lithium derivative of its conjugate base, lithium diisopropylamide, known as "LDA". LDA is a strong, non-nucleophilic base.

Diisopropylamine can be dried by distillation from potassium hydroxide (KOH) or drying over sodium wire.[1]