110-96-3

Basic information

• Product Name: Diisobutylamine
• Synonyms: (i-C4H9)2NH;1-Propanamine,2-methyl-N-(2-methylpropyl)-;2-methyl-n-(2-methylpropyl)-1-propanamin;amine,diisobutyl;bis(2-Methylpropyl)amine;bis(beta-methylpropyl)amine;Di(-2-methylpropyl)amine;dibutylamine(non-specificname)
• CAS NO: 110-96-3
• Molecular Formula: C₈H₁₉N
• Molecular Weight: 129.24
• EINECS: 203-819-3
• Product Categories: Amines;C8;Nitrogen Compounds
• Mol File: 110-96-3.mol

Chemical Properties

• Melting Point: -77 °C
• Boiling Point: 137-139 °C(lit.)
• Flash Point: 85 °F
• Appearance: Clear/Liquid
• Density: 0.74 g/mL at 25 °C(lit.)
• Vapor Pressure: 7.07mmHg at 25°C
• Refractive Index: n20/D 1.4081(lit.)
• Storage Temp.: Flammables area
• Solubility: insoluble to slightly soluble in water; soluble in ethanol, methanol, ethyl ether, ethyl acetate, acetone, benzene, aromatic and aliphatic hydrocarbons, fixed oils, mineral oil, oleic and stearic acids
• PKA: 11.07±0.28(Predicted)
• Water Solubility: 5 g/L (20 ºC)
• Sensitive: Air Sensitive
• BRN: 1209251
• CAS DataBase Reference: Diisobutylamine(CAS DataBase Reference)
• NIST Chemistry Reference: Diisobutylamine(110-96-3)
• EPA Substance Registry System: Diisobutylamine(110-96-3)

Safety Data

• Hazard Codes: C
• Statements: 10-22-34-52/53
• Safety Statements: 26-36/37/39-45-25-16-61
• RIDADR: UN 2361 3/PG 3
• WGK Germany: 1
• RTECS: TX1750000
• F: 34
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 110-96-3(Hazardous Substances Data)

Usage

Uses

Used in Chemical Research:
Diisobutylamine is used as an achiral amine in the study of the effect on hydrogenation of ethyl pyruvate over a cinchonidine-Pt/Al2O3 catalyst system.
Used in Agricultural Industry:
Diisobutylamine is used as a chemical intermediate for the manufacture of various agricultural products.
Used in Pharmaceutical Industry:
Diisobutylamine is used as a chemical intermediate in the production of several pharmaceutical products.

Production Methods

Diisobutylamine can be produced by the reaction of ammonia and butanol over a dehydration catalyst at high temperature and pressure (Hawley 1977). Alternatively, ammonia, butanol, and hydrogen can be passed over a dehydrogenation catalyst. In 1976, 18,000 tons of diisobutylamine were produced (Schweizer et al 1978). Diisobutylamine is also naturally present in foods and soil. As with other secondary amines, diisobutylamine can be nitrosated to form the highly toxic (Olah 1975) N-nitrosodiisobutylamine (Guttenplan 1987; Vlasenko et al 1981; Spiegeholder et al 1978). Thus, nitrosation of commercial preparations of diisobutylamine occurs on standing, presumably by reaction with nitrogen oxides in the air (Spiegelhalder et al 1978) and N-nitrosodiisobutylamine has been found in various fishery products (Kawabata et al 1974) and other foods (Osborne 1972; Telling 1972).

Air & Water Reactions

Highly flammable. Sensitive to heat and air. Insoluble in water.

Reactivity Profile

Diisobutylamine can react vigorously with oxidizing materials . Neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Health Hazard

Inhalation of high concentrations of vapor will cause irritation of the respiratory tract and the lungs. Contact with liquid may result in severe skin and eye irritation. Exposure to concentrated vapors may result in corneal edema. Poisonous if swallowed.

Health Hazard

Diisobutylamine is a relatively strong base and is therefore irritating to the eyes, respiratory tract, and skin. Inhalation of vapors can result in pulmonary edema following prolonged exposure. Ingestion of liquid can cause severe burning of the esophagus.

Safety Profile

Poison by ingestion. A dangerous fire hazard when exposed to heator flame; can react vigorously with oxidizing materials. To fight fire, use alcohol foam, CO2, dry chemical. When heated to decomposition it emits toxic fumes of Nox

Metabolism

There is little information available on the metabolism of diisobutylamine.

InChI:InChI=1/C8H19N/c1-5-7(3)9-8(4)6-2/h7-9H,5-6H2,1-4H3/p+1/t7-,8-/m1/s1

Upstream product

• 542-56-3 nitrous acid isobutyl ester 
• 597-46-6 2,5-dimethyl-2-nitro-hexane 
• 78-84-2 isobutyraldehyde 
• 18300-78-2 diisobutylidene-hydrazine 
• 997-95-5 N-Nitroso-diisobutylamin 
• 98-16-8 3-trifluoromethylaniline 
• 106-49-0 p-toluidine 
• 104-94-9 4-methoxy-aniline 
• 75670-24-5 N,N-diisobutyl-N'-phenyl-urea 
• 62-53-3 aniline 
• 78-81-9 isobutylamine 
• 67-56-1 methanol 
• 7664-41-7 ammonia 
• 78-83-1 2-methyl-propan-1-ol 

Downstream Products

• 4535-66-4 2-(diisobutylamino)ethanol 
• 5842-09-1 2-Diisobutylamino-ethylmercaptan 
• 6312-33-0 diisobutyl-(2-pyridin-2-yl-ethyl)-amine 
• 84472-25-3 (1S,2S)-N-<(2-Hydroxy-2-phenyl)-1-methyl-ethyl>-N-methylacetamid 
• 2272-83-5 (1R,2S)-N-<(2-Hydroxy-2-phenyl)-1-methyl-ethyl>-N-methylacetamid 
• 3064-73-1 tetra(isobutyl)thiuram disulfide 
• 38952-42-0 diisobutylcarbamic acid chloride 
• 21661-48-3 N,N-diisobutyl-phthalamic acid 
• 2591-76-6 N,N-bis(2-methylpropyl)formamide 
• 42276-93-7 dichloro-acetic acid diisobutylamide 
• 41123-56-2 2,2-bis-ethylenesulfonyl-propane 
• 114890-12-9 2,2-bis-(2-diisobutylamino-ethanesulfonyl)-propane 
• 54699-24-0 N,N,N′,N′-tetra-iso-butylurea 
• 30893-21-1 N,N-diisobutylnitramine 

Relevant articles and documents

One-pot reductive amination of carboxylic acids: a sustainable method for primary amine synthesis

The reductive amination of carboxylic acids is a very green, efficient and sustainable method for the production of (bio-based) amines. However, with current technology, this reaction requires two to three reaction steps. Here, we report the first (heterogeneous) catalytic system for the one-pot reductive amination of carboxylic acids to amines, with solely H2 and NH3 as the reactants. This reaction can be performed with relatively cheap ruthenium-tungsten bimetallic catalysts in the green and benign solvent cyclopentyl methyl ether (CPME). Selectivities of up to 99% for the primary amine could be achieved at high conversions. Additionally, the catalyst is recyclable and tolerant for common impurities such as water and cations (e.g. sodium carboxylate).

Direct ortho-Selective Amination of 2-Naphthol and Its Analogues with Hydrazines

Described herein is a regioselective ortho-amination of 2-naphthol and its analogues with substituted hydrazines. It provides a direct methodology for the synthesis of N-arylaminated naphthol derivatives without the formation of related 1,1′-biaryl-2,2′-diamine or carbazole byproducts. Specifically, using N,N-disubstituted hydrazine precursors, N-unsubstituted ortho-aminated derivatives and related secondary amines can be formed in ethylene glycol in moderate to excellent yields. Variation of substrates to N,N′-diarylhydrazines and N-methyl-N,N′-diarylhydrazines led to N-aryl-1-amino-2-naphthol compounds. It is noted that biologically interesting indazole motifs can be facilely created by the reaction of N,N′-dialkylhydrazines with 2-naphthols. These ortho-amination reactions have the advantage of one-pot operation without the use of transition metal catalysts.

Continuous Production of Dialkylamines by Selective Hydrogenation of Nitriles on a Nickel-Zeolite Catalyst

Hydrogenation of aliphatic nitriles in the presence of nickel supported by NaX zeolite was studied. The data obtained were used to develop a continuous method for obtaining dialkylamines with the yield of the target product of up to 98%.

Colloid and nanosized catalysts in organic synthesis: XVI.1 Continuous hydrogenation of carbonitriles catalyzed by nickel nanoparticles applied on a support

Conversion of the starting nitriles and selectivity of the products formation during continuous hydrogenation of various nitriles catalyzed by Ni0/Ceokar-2 have been studied as functions of temperature. Performing the process at temperature 120–260°С has led to the formation of a mixture of products containing di- and trialkylamines as well as the corresponding imines and enamines.

Colloid and nanosized catalysts in organic synthesis: XVII. Reductive amination of carbonitriles in the presence of supported nickel nanoparticles

Reductive amination of carbonitriles catalyzed by nickel nanoparticles applied onto a solid support in a plug flow reactor in the gas phase or the gas–liquid–solid catalyst system occurs at atmospheric pressure of hydrogen affording the nonsymmetrical secondary or tertiary amines. The effect of the support type on the target product yield and conversion of the substrate has been studied.

Colloid and nanosized catalysts in organic synthesis: XII. Hydrogenation of carbonitriles catalyzed by nickel nanoparticles

Hydrogenation of carbonitriles catalyzed by nickel nanoparticles in isopropanol proceeds under atmospheric pressure of hydrogen within 6-15 h to yield mainly secondary amines. Hydrogenation of α-aminonitriles results in reductive decyanation. β-Aminonitriles undergo hydrogenolysis at the nitrogen-carbon bond.

Catalytic hydrogenation of amides to amines under mild conditions

Under (not so much) pressure: A general method for the hydrogenation of tertiary and secondary amides to amines with excellent selectivity using a bimetallic Pd-Re catalyst has been developed. The reaction proceeds under low pressure and comparatively low temperature. This method provides organic chemists with a simple and reliable tool for the synthesis of amines. Copyright

Reduction of hydrazines to amines with low-valent titanium reagent

The N,N bond cleavage in hydrazines to amines via low-valent titanium reagent prepared in situ by treatment of TiCl4 with Mg powder in THF or CH2Cl2-Et2O is described. The reaction proceeds smoothly under mild conditions to afford amines in good to excellent yields with diverse functional group tolerance such as chloride, methoxyl, benzyloxyl, ester, acyl, as well as C,C double bonds and benzyl-nitrogen bonds. ARKAT-USA, Inc.

An efficient synthesis of tertiary amines from nitriles in aprotic solvents

Tertiary amines are utilized extensively as non-nucleophilic proton scavengers for a number of organic transformations. Herein we report the efficient syntheses of tertiary alkyl amines from their corresponding alkyl nitriles in the presence of a heterogeneous palladium catalyst and a source of dihydrogen in aprotic solvents. The reaction is atom economic, the conditions are mild, and the isolated yields are virtually quantitative. The degree of amine alkylation shows some solvent dependency; in polar protic solvents such as ethanol or methanol, the reaction affords a mixture of products with the secondary alkyl amine as the major product.

Reduction of hydrazines to amines with aqueous solution of titanium(iii) trichloride

N-N bond cleavage in hydrazines is widely used in the preparation of amines and thus occupies a significant place in organic synthesis. In this paper, we report a new method for the reductive cleavage of N-N bonds in hydrazines by commercially available and cheap aqueous titanium(iii) trichloride. The reaction proceeds smoothly under a broad pH range from acidic to neutral and basic conditions to afford amines in good yields. This method is compatible with substrates containing functionalities such as C-C double bonds, benzyl-nitrogen bonds, benzyloxy and acyl groups. The Royal Society of Chemistry 2011.