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.

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