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 | |
3D model (JSmol) | |
605284 | |
ChemSpider | |
ECHA InfoCard | 100.003.235 |
EC Number |
|
PubChem CID | |
RTECS number |
|
UNII | |
UN number | 1158 |
CompTox Dashboard (EPA) | |
| |
| |
Properties | |
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 |
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 labelling: | |
Danger | |
H225, H302, H314, H332 | |
P210, P280, P305+P351+P338, P310 | |
NFPA 704 (fire diamond) | |
Flash point | −17 °C (1 °F; 256 K) |
315 °C (599 °F; 588 K) | |
Explosive limits | 1.1–7.1% [1] |
Lethal dose or concentration (LD, LC): | |
LD50 (median dose) |
|
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 | |
Related compounds | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
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.
Diisopropylamine is a common amine nucleophile in organic synthesis. [4] Because it is bulky, it is a more selective nucleophile than other similar amines, such as 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 the herbicide, 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]
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]
Diisopropylamine can be dried by distillation from potassium hydroxide (KOH) or drying over sodium wire. [12] : 186
Diisopropylamine causes burns by all exposure routes. Inhalation of high concentrations of its vapor may cause symptoms like headache, dizziness, tiredness, nausea and vomiting.
The Pinner reaction refers to the acid catalysed reaction of a nitrile with an alcohol to form an imino ester salt ; this is sometimes referred to as a Pinner salt. The reaction is named after Adolf Pinner, who first described it in 1877. Pinner salts are themselves reactive and undergo additional nucleophilic additions to give various useful products:
Hydrazones are a class of organic compounds with the structure R1R2C=N−NH2. They are related to ketones and aldehydes by the replacement of the oxygen =O with the =N−NH2 functional group. They are formed usually by the action of hydrazine on ketones or aldehydes.
In organic chemistry, an imine is a functional group or organic compound containing a carbon–nitrogen double bond. The nitrogen atom can be attached to a hydrogen or an organic group (R). The carbon atom has two additional single bonds. Imines are common in synthetic and naturally occurring compounds and they participate in many reactions.
Lithium diisopropylamide is a chemical compound with the molecular formula LiN(CH 2)2. It is used as a strong base and has been widely utilized due to its good solubility in non-polar organic solvents and non-nucleophilic nature. It is a colorless solid, but is usually generated and observed only in solution. It was first prepared by Hamell and Levine in 1950 along with several other hindered lithium diorganylamides to effect the deprotonation of esters at the α position without attack of the carbonyl group.
The Hofmann rearrangement is the organic reaction of a primary amide to a primary amine with one less carbon atom. The reaction involves oxidation of the nitrogen followed by rearrangement of the carbonyl and nitrogen to give an isocyanate intermediate. The reaction can form a wide range of products, including alkyl and aryl amines.
In organic chemistry, enolates are organic anions derived from the deprotonation of carbonyl compounds. Rarely isolated, they are widely used as reagents in the synthesis of organic compounds.
The Gabriel synthesis is a chemical reaction that transforms primary alkyl halides into primary amines. Traditionally, the reaction uses potassium phthalimide. The reaction is named after the German chemist Siegmund Gabriel.
As the name suggests, a non-nucleophilic base is a sterically hindered organic base that is a poor nucleophile. Normal bases are also nucleophiles, but often chemists seek the proton-removing ability of a base without any other functions. Typical non-nucleophilic bases are bulky, such that protons can attach to the basic center but alkylation and complexation is inhibited.
The Vilsmeier–Haack reaction (also called the Vilsmeier reaction) is the chemical reaction of a substituted formamide (1) with phosphorus oxychloride and an electron-rich arene (3) to produce an aryl aldehyde or ketone (5):
N,N-Diisopropylethylamine, or Hünig's base, is an organic compound that is a tertiary amine. It is named after the German chemist Siegfried Hünig. It is used in organic chemistry as a non-nucleophilic base. It is commonly abbreviated as DIPEA,DIEA, or i-Pr2NEt.
Cyanamide is an organic compound with the formula CN2H2. This white solid is widely used in agriculture and the production of pharmaceuticals and other organic compounds. It is also used as an alcohol-deterrent drug. The molecule features a nitrile group attached to an amino group. Derivatives of this compound are also referred to as cyanamides, the most common being calcium cyanamide (CaCN2).
The Feist–Benary synthesis is an organic reaction between α-halo ketones and β-dicarbonyl compounds to produce substituted furan compounds. This condensation reaction is catalyzed by amines such as ammonia and pyridine. The first step in the ring synthesis is related to the Knoevenagel condensation. In the second step the enolate displaces an alkyl halogen in a nucleophilic aliphatic substitution.
1,4-Benzoquinone, commonly known as para-quinone, is a chemical compound with the formula C6H4O2. In a pure state, it forms bright-yellow crystals with a characteristic irritating odor, resembling that of chlorine, bleach, and hot plastic or formaldehyde. This six-membered ring compound is the oxidized derivative of 1,4-hydroquinone. The molecule is multifunctional: it exhibits properties of a ketone, being able to form oximes; an oxidant, forming the dihydroxy derivative; and an alkene, undergoing addition reactions, especially those typical for α,β-unsaturated ketones. 1,4-Benzoquinone is sensitive toward both strong mineral acids and alkali, which cause condensation and decomposition of the compound.
Trimethylsilyl chloride, also known as chlorotrimethylsilane is an organosilicon compound, with the formula (CH3)3SiCl, often abbreviated Me3SiCl or TMSCl. It is a colourless volatile liquid that is stable in the absence of water. It is widely used in organic chemistry.
Diethylamine is an organic compound with the formula (CH3CH2)2NH. It is a secondary amine. It is a flammable, weakly alkaline liquid that is miscible with most solvents. It is a colorless liquid, but commercial samples often appear brown due to impurities. It has a strong ammonia-like odor.
Allyl bromide (3-bromopropene) is an organic halide. It is an alkylating agent used in synthesis of polymers, pharmaceuticals, synthetic perfumes and other organic compounds. Physically, allyl bromide is a colorless liquid with an irritating and persistent smell, however, commercial samples are yellow or brown. Allyl bromide is more reactive but more expensive than allyl chloride, and these considerations guide its use.
The Willgerodt rearrangement or Willgerodt reaction is an organic reaction converting an aryl alkyl ketone, alkyne, or alkene to the corresponding amide by reaction with ammonium polysulfide, named after Conrad Willgerodt. The formation of the corresponding carboxylic acid is a side reaction resulting from hydrolysis of the amide. When the alkyl group is an aliphatic chain, multiple reactions take place with the amide group always ending up at the terminal end. The net effect is thus migration of the carbonyl group to the end of the chain and oxidation.
In organic chemistry, ethenone is the formal name for ketene, an organic compound with formula C2H2O or H2C=C=O. It is the simplest member of the ketene class. It is an important reagent for acetylations.
The Enders SAMP/RAMP hydrazone alkylation reaction is an asymmetric carbon-carbon bond formation reaction facilitated by pyrrolidine chiral auxiliaries. It was pioneered by E. J. Corey and D. Enders in 1976, and was further developed by D. Enders and his group. This method is usually a three-step sequence. The first step is to form the hydrazone between (S)-1-amino-2-methoxymethylpyrrolidine (SAMP) or (R)-1-amino-2-methoxymethylpyrrolidine (RAMP) and a ketone or aldehyde. Afterwards, the hydrazone is deprotonated by lithium diisopropylamide (LDA) to form an azaenolate, which reacts with alkyl halides or other suitable electrophiles to give alkylated hydrazone species with the simultaneous generation of a new chiral center. Finally, the alkylated ketone or aldehyde can be regenerated by ozonolysis or hydrolysis.
Benzophenone imine is an organic compound with the formula of (C6H5)2C=NH. A pale yellow liquid, benzophenone imine is used as a reagent in organic synthesis.
{{cite journal}}
: CS1 maint: multiple names: authors list (link){{cite encyclopedia}}
: |journal=
ignored (help)