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;
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 ;
	show InChI
	show SMILES
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
Vapor pressure	9.3 kPa (at 20°C)
Acidity (pKa)	11.07 (in water) (conjugate acid)
Basicity (pKb)	3.43
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)	2 3 0
Flash point	−17 °C (1 °F; 256 K)
Autoignition; temperature	315 °C (599 °F; 588 K)
Explosive limits	1.1–7.1%
	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)
LCLo (lowest published)	2207 ppm (rabbit, 2.5 hr); 2207 ppm (guinea pig, 80 min); 2207 ppm (cat, 72 min)
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 5 ppm (20 mg/m3) [skin]
REL (Recommended)	TWA 5 ppm (20 mg/m3) [skin]
IDLH (Immediate danger)	200 ppm
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).
	(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]^: 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[]

^ Jump up to: ^a ^b ^c ^d ^e NIOSH Pocket Guide to Chemical Hazards. "#0217". National Institute for Occupational Safety and Health (NIOSH).
^ Jump up to: ^a ^b CID 7912 from PubChem
^ Jump up to: ^a ^b "Diisopropylamine". Immediately Dangerous to Life or 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.

[PGCH-1] Jump up to: ^a ^b ^c ^d ^e NIOSH Pocket Guide to Chemical Hazards. "#0217". National Institute for Occupational Safety and Health (NIOSH).

[pubchem-2] Jump up to: ^a ^b CID 7912 from PubChem

[IDLH-3] Jump up to: ^a ^b "Diisopropylamine". Immediately Dangerous to Life or 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.

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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^Y
3D model (JSmol)	Interactive image
Beilstein Reference	605284
ChemSpider	7624^Y
ECHA InfoCard	100.003.235
EC Number	203-558-5
PubChem CID	7912
RTECS number	IM4025000
UNII	BR9JLI40NO^Y
UN number	1158
CompTox Dashboard (EPA)	DTXSID9025085
show InChI InChI=1S/C6H15N/c1-5(2)7-6(3)4/h5-7H,1-4H3^Y Key: UAOMVDZJSHZZME-UHFFFAOYSA-N^Y
show 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 (pK_a)	11.07 (in water) (conjugate acid)
Basicity (pK_b)	3.43^[2]
Refractive index (n_D)	1.392–1.393
Thermochemistry
Std enthalpy of formation (Δ_fH^⦵₂₉₈)	−173.6 to −168.4 kJ mol⁻¹
Std enthalpy of combustion (Δ_cH^⦵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)	2 3 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]
LC_Lo (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).
N (what is ^YN ?)
Infobox references