Diisopropylamine

Diisopropylamine
Names
	Preferred IUPAC name N-(Propan-2-yl)propan-2-amine
	Other names Di(propan-2-yl)amine; N-Isopropylpropan-2-amine; (Diisopropyl)amine; (The name diisopropylamine is deprecated.)
Identifiers
CAS Number	108-18-9 ;
3D model (JSmol)	Interactive image;
Abbreviations	DIPA
Beilstein Reference	605284
ChemSpider	7624 ;
ECHA InfoCard	100.003.235
EC Number	203-558-5;
PubChem CID	7912;
RTECS number	IM4025000;
UNII	BR9JLI40NO ;
UN number	1158
CompTox Dashboard (EPA)	DTXSID9025085 ;
	InChI InChI=1S/C6H15N/c1-5(2)7-6(3)4/h5-7H,1-4H3 Key: UAOMVDZJSHZZME-UHFFFAOYSA-N ;
	SMILES CC(C)NC(C)C;
Properties
Chemical formula	C6H15N
Molar mass	101.193 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
Solubility in water	miscible[1]
Vapor pressure	9.3 kPa (at 20°C)[2]
Acidity (pKa)	11.07 (in water) (conjugate acid)
Basicity (pKb)	3.43[2]
Refractive index (nD)	1.392–1.393
Thermochemistry
Std enthalpy of; formation (ΔfH⦵298)	−173.6 to −168.4 kJ mol−1
Std enthalpy of; combustion (ΔcH⦵298)	−4.3363 to −4.3313 MJ mol−1
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H225, H302, H314, H332
GHS precautionary statements	P210, P280, P305+351+338, P310
NFPA 704 (fire diamond)	3 2 0
Flash point	−17 °C (1 °F; 256 K)
Autoignition; temperature	315 °C (599 °F; 588 K)
Explosive limits	1.1–7.1%[1]
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	770 mg kg−1 (oral, rat); >10 g kg−1 (dermal, rabbit);
LC50 (median concentration)	1140 ppm (rat, 2 hr); 1000 ppm (mouse, 2 hr)[3]
LCLo (lowest published)	2207 ppm (rabbit, 2.5 hr); 2207 ppm (guinea pig, 80 min); 2207 ppm (cat, 72 min)[3]
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 5 ppm (20 mg/m3) [skin][1]
REL (Recommended)	TWA 5 ppm (20 mg/m3) [skin][1]
IDLH (Immediate danger)	200 ppm[1]
Related compounds
Related amines	Dimethylamine; Diethylamine;
Related compounds	Triisopropylamine; N,N-Diisopropylethylamine;
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

Diisopropylamine is a secondary amine with the chemical formula (Me₂CH)₂NH (Me = methyl). Diisopropylamine is a colorless liquid with an ammonia-like odor. Its lithium derivative, lithium diisopropylamide, known as LDA is a widely used reagent.

Reactions and use

Diisopropylamine is a common amine nucleophile in organic synthesis.[4] Because it is bulky, it is a more selective nucleophile than, say, dimethylamine.[5]

It reacts with organolithium reagents to give lithium diisopropylamide (LDA). LDA is a strong, non-nucleophilic base[6]

The main commercial applications of diisopropylamine is as a precursor to two herbicides, diallate and triallate, as well as certain sulfenamides used in the vulcanization of rubber.[7]

It is also used to prepare N,N-Diisopropylethylamine (Hünig's base) by alkylation with diethyl sulfate.[8]

The bromide salt of diisopropylamine, diisopropylammonium bromide, is a room-temperature organic ferroelectric material.[9]

Preparation

Diisopropylamine, which is commercially available, may be prepared by the reductive amination of acetone with ammonia using a modified copper oxide, generally copper chromite, as a catalyst:[10][11]

NH
₃ + 2(CH
₃)
₂CO + 2H
₂ → C
₆H
₁₅N + 2H
₂O

Diisopropylamine can be dried by distillation from potassium hydroxide (KOH) or drying over sodium wire.[12]{{rp|page=186}

Toxicity

Causes burns by all exposure routes. Inhalation of high vapor concentrations may cause symptoms like headache, dizziness, tiredness, nausea and vomiting.[13]

References

NIOSH Pocket Guide to Chemical Hazards. "#0217". National Institute for Occupational Safety and Health (NIOSH).
CID 7912 from PubChem
"Diisopropylamine". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
John E. McMurry, Jack Melton (1977). "Conversion of Nitro to Carbonyl by Ozonolysis of Nitronates: 2,5-Heptanedione". Organic Syntheses. 56: 36. doi:10.15227/orgsyn.056.0036.
Denmark, Scott; Ryabchuk, Pavel; Min Chi, Hyung; Matviitsuk, Anastassia (2019). "Preparation of a Diisopropylselenophosphoramide Catalyst and its Use in Enantioselective Sulfenoetherification". Organic Syntheses. 96: 400–417. doi:10.15227/orgsyn.096.0400.
George M. Rubottom, John M. Gruber, Henrik D. Juve, Jr, , Dan A. Charleson (1986). "α-Hydroxy Ketones from the Oxidation of Enol Silyl Ethers with m-Chloroperbenzoic Acid: 6-Hydroxy- 3,5,5-trimethyl-2-cyclohexen-1-one". Organic Syntheses. 64: 118. doi:10.15227/orgsyn.064.0118.CS1 maint: multiple names: authors list (link)
Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; Höke, Hartmut (15 June 2000). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH. doi:10.1002/14356007.a02_001. ISBN 978-3527303854. OL 9052422M.
Hünig, Siegfried; Kiessel, Max (1 April 1958). "Spezifische Protonenacceptoren als Hilfsbasen bei Alkylierungs- und Dehydrohalogenierungsreaktionen" [Specific proton acceptors as auxiliary bases in alkylation and dehydrohalogenation reactions]. Chemische Berichte (in German). Wiley-VCH. 91 (2): 380–392. doi:10.1002/cber.19580910223. ISSN 0009-2940. OCLC 889715844.
Fu, Da-Wei; Cai, Hong-Ling; Liu, Yuanming; Ye, Qiong; Zhang, Wen; et al. (25 January 2013). "Diisopropylammonium Bromide Is a High-Temperature Molecular Ferroelectric Crystal". Science. 339 (6118): 425–428. doi:10.1126/science.1229675. eISSN 1095-9203. ISSN 0036-8075. LCCN 17024346. OCLC 1644869. PMID 23349285. S2CID 12389978.
Löffler, Karl (1 April 1910). "Über eine neue Bildungsweise primärer und sekundärer Amine aus Ketonen" [About a new way of forming primary and secondary amines from ketones]. Berichte der Deutschen Chemischen Gesellschaft (in German). 43 (2): 2031–2035. doi:10.1002/cber.191004302145. ISSN 0365-9496. OCLC 219854722.
US 2686811, Willard Bull, "One-step process for preparing diisopropylamine"
Armarego, W. L. F.; Perrin, D. D. (16 October 1996). Purification of Laboratory Chemicals (4th ed.). Butterworth-Heinemann. ISBN 978-0750628396. LCCN 97109714. OCLC 762966259. OL 722457M.
"SAFETY DATA SHEET--Triethylamine". ThermoFisher Scientific. Jan 17, 2018. Retrieved June 18, 2020.

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[PGCH-1] NIOSH Pocket Guide to Chemical Hazards. "#0217". National Institute for Occupational Safety and Health (NIOSH).

[pubchem-2] CID 7912 from PubChem

[IDLH-3] "Diisopropylamine". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[4] John E. McMurry, Jack Melton (1977). "Conversion of Nitro to Carbonyl by Ozonolysis of Nitronates: 2,5-Heptanedione". Organic Syntheses. 56: 36. doi:10.15227/orgsyn.056.0036.

[5] Denmark, Scott; Ryabchuk, Pavel; Min Chi, Hyung; Matviitsuk, Anastassia (2019). "Preparation of a Diisopropylselenophosphoramide Catalyst and its Use in Enantioselective Sulfenoetherification". Organic Syntheses. 96: 400–417. doi:10.15227/orgsyn.096.0400.

[6] George M. Rubottom, John M. Gruber, Henrik D. Juve, Jr, , Dan A. Charleson (1986). "α-Hydroxy Ketones from the Oxidation of Enol Silyl Ethers with m-Chloroperbenzoic Acid: 6-Hydroxy- 3,5,5-trimethyl-2-cyclohexen-1-one". Organic Syntheses. 64: 118. doi:10.15227/orgsyn.064.0118.CS1 maint: multiple names: authors list (link)

[7] Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; Höke, Hartmut (15 June 2000). "Amines, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH. doi:10.1002/14356007.a02_001. ISBN 978-3527303854. OL 9052422M.

[Hünig1958-8] Hünig, Siegfried; Kiessel, Max (1 April 1958). "Spezifische Protonenacceptoren als Hilfsbasen bei Alkylierungs- und Dehydrohalogenierungsreaktionen" [Specific proton acceptors as auxiliary bases in alkylation and dehydrohalogenation reactions]. Chemische Berichte (in German). Wiley-VCH. 91 (2): 380–392. doi:10.1002/cber.19580910223. ISSN 0009-2940. OCLC 889715844.

[2013_Science-9] Fu, Da-Wei; Cai, Hong-Ling; Liu, Yuanming; Ye, Qiong; Zhang, Wen; et al. (25 January 2013). "Diisopropylammonium Bromide Is a High-Temperature Molecular Ferroelectric Crystal". Science. 339 (6118): 425–428. doi:10.1126/science.1229675. eISSN 1095-9203. ISSN 0036-8075. LCCN 17024346. OCLC 1644869. PMID 23349285. S2CID 12389978.

[10] Löffler, Karl (1 April 1910). "Über eine neue Bildungsweise primärer und sekundärer Amine aus Ketonen" [About a new way of forming primary and secondary amines from ketones]. Berichte der Deutschen Chemischen Gesellschaft (in German). 43 (2): 2031–2035. doi:10.1002/cber.191004302145. ISSN 0365-9496. OCLC 219854722.

[11] US 2686811, Willard Bull, "One-step process for preparing diisopropylamine"

[12] Armarego, W. L. F.; Perrin, D. D. (16 October 1996). Purification of Laboratory Chemicals (4th ed.). Butterworth-Heinemann. ISBN 978-0750628396. LCCN 97109714. OCLC 762966259. OL 722457M.

[13] "SAFETY DATA SHEET--Triethylamine". ThermoFisher Scientific. Jan 17, 2018. Retrieved June 18, 2020.