1116-70-7

Basic information

• Product Name: TRI-N-BUTYLALUMINUM
• Synonyms: tributyl-Aluminum;ALUMINUM TRI-N-BUTYL;TRI-N-BUTYLALUMINIUM;TRI-N-BUTYLALUMINUM;Tributyl aluminium;TNBA;Aluminumtri-n-butyl25%soln.inheptane;Tri-n-butylaluminium, 0.7M solution in heptane
• CAS NO: 1116-70-7
• Molecular Formula: C₁₂H₂₇Al
• Molecular Weight: 198.32
• EINECS: 214-240-0
• Mol File: 1116-70-7.mol
• Article Data: 3

Chemical Properties

• Melting Point: -27 °C
• Boiling Point: 98°C
• Appearance: /
• Density: 0.711
• Storage Temp.: water-free area
• CAS DataBase Reference: TRI-N-BUTYLALUMINUM(CAS DataBase Reference)
• NIST Chemistry Reference: TRI-N-BUTYLALUMINUM(1116-70-7)
• EPA Substance Registry System: TRI-N-BUTYLALUMINUM(1116-70-7)

Safety Data

• Hazard Codes: N-C-F
• Statements: 67-65-50/53-34-14/15-11
• Safety Statements: 6A-57-45-43E-36/37/39-29-26-16
• RIDADR: 3051
• HazardClass: 4.2
• PackingGroup: I
• Hazardous Substances Data: 1116-70-7(Hazardous Substances Data)

Usage

Chemical Properties

The aluminum alkyls are highly flammable and reactive, colorless to yellow liquids at room temperature. The lighter trialkylaluminums ignite spontaneously in air. They are normally supplied and used in a 20% solution with a hydrocarbon solvent, such as hexane, heptane, benzene, toluene. Properties may depend on solvent. Reacts violently with water.

Uses

Production of organo-tin compounds.

General Description

A colorless to light-yellow colored liquid. Likely to cause burns on contact with skin, eyes or mucous membranes. Fumes pose a serious inhalation hazard.

Air & Water Reactions

Highly flammable. Fumes in air. May ignite on contact with moist air. May ignite on contact with water.

Reactivity Profile

TRI-N-BUTYLALUMINUM is a strong reducing agent. May react rapidly and dangerously with oxygen and other oxidizing agents, even weak ones. Thus likely to ignite on contact with alcohols. Incompatible with acids, alcohols, amines, and aldehydes.

Health Hazard

Fire will produce irritating, corrosive and/or toxic gases. Inhalation of decomposition products may cause severe injury or death. Contact with substance may cause severe burns to skin and eyes. Runoff from fire control may cause pollution.

Fire Hazard

Flammable/combustible material. May ignite on contact with moist air or moisture. May burn rapidly with flare-burning effect. Some react vigorously or explosively on contact with water. Some may decompose explosively when heated or involved in a fire. May re-ignite after fire is extinguished. Runoff may create fire or explosion hazard. Containers may explode when heated.

Potential Exposure

Alkyl aluminum compounds are used as components of olefin polymerization catalysts. They are also used in the synthesis of higher primary alcohols and in pyrophoric fuels, as a catalyst in making ethylene gas; and in plating aluminum.

Shipping

ntial fire or explosion hazard. Shipping: UN3399 Organometallic substance, liquid, water-reactive, flammable, Hazard Class: 4.3; Labels: 4.3 Dangerous Dangerous when wet material, 3-Flammable liquid, technical name Required. UN3051-Spontaneously combustible. Also, this material is dangerous when wet. (Note: this number does not appear in the 49/CFR HazMat tables).

Incompatibilities

The lighter trialkylaluminums ignite spontaneously in air; can self-heat in the air at room temperature without any added energy and may ignite. These compounds are strong reducing agents. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Incompatible with water, oxygen (air), acids, alcohols, phenols, amines, carbon dioxide; sulfur oxides; halogenated compounds, and many other substances

Waste Disposal

Careful incineration

InChI:InChI=1/3C4H9.Al/c3*1-3-4-2;/h3*1,3-4H2,2H3;/rC12H27Al/c1-4-7-10-13(11-8-5-2)12-9-6-3/h4-12H2,1-3H3

Synthetic route

(i-Bu3Al)2*diphos → tri(n-butyl)aluminium (1116-70-7)

Conditions	Yield
In neat (no solvent) heated slowly under 1E-2 mmHg in a trap-to-trap distillation apparatus (receiver flask at -196 °C), liberation of i-Bu3Al started at 80 °C, the rate was more satisfactory at 120-130 °C;;	88%

1-iodo-butane (542-69-8) → tri(n-butyl)aluminium (1116-70-7)

Conditions	Yield
With aluminium-magnesium

1-bromo-butane (109-65-9) + methoxybenzene (100-66-3) + magnesium aluminium-alloy → tri(n-butyl)aluminium (1116-70-7)

Conditions	Yield
at 110℃;

tri-sec-butyl alane → tri(n-butyl)aluminium (1116-70-7)

NaF*2Al(n-C4H9)3 → Na{Al(n-C4H9)3F} + tri(n-butyl)aluminium (1116-70-7)

Conditions	Yield
by heating under reduced pressure;

aluminum(III) borohydride + dibutylmagnesium (1191-47-5) → magnesium borohydride + tri(n-butyl)aluminium (1116-70-7)

Conditions	Yield
In toluene mixing of Mg(C4H9)2 and Al(BH4)3 (in 3:2 molar ratio) in toluene, pptn.,stirring overnight; filtration, washing with toluene; drying under vac.; monitoring by XRD and NMR;

aluminum (III) chloride (7446-70-0, 7784-13-6) + 1-iodo-butane (542-69-8) → tri(n-butyl)aluminium (1116-70-7)

Conditions	Yield
Stage #1: 1-iodo-butane With n-butyllithium In tetrahydrofuran Inert atmosphere; Glovebox; Stage #2: aluminum (III) chloride In tetrahydrofuran at 20℃; for 0.75h; Inert atmosphere; Glovebox;

dibutylmagnesium (1191-47-5) + tri(n-butyl)aluminium (1116-70-7) → (C4H9)2AlOAl(C4H9)OMgC4H9 (84560-30-5)

Conditions	Yield
With water In n-heptane H2O add. (medical syringe, 4-6 h, 30-40°C ) into Al- and Mg-compds. (molar ratio Al:Mg=2:1) soln.; soln. sepn. from ppt., heptane driving off (30-40°C, 1-5 mm); elem. anal.;	100%

dibutylmagnesium (1191-47-5) + tri(n-butyl)aluminium (1116-70-7) → [(AlO)(MgO)(C4H9)]40

Conditions	Yield
With water In diethyl ether; n-heptane equimolar amount of water soln. (ether) addn. (dropwise) to Al- and Mg-compds. soln. (heptane) at 20-25°C during 1-2 h, solvents drivingoff, polymer keeping for 1 h at 150°C at residual pressure of 1-5 mm; elem. anal.;	100%
With water In n-heptane H2O add. (medical syringe, 4-6 h, 30-40°C) into Al- and Mg-compds. (molar ratio Al:Mg=1:1) soln.; soln. sepn. from ppt., heptane driving off (30-40°C, 1-5 mm); elem. anal.;	100%

tri-n-butylboroxine (7359-98-0) + tri(n-butyl)aluminium (1116-70-7) → tributyl borane (122-56-5)

Conditions	Yield
at 100 - 140℃; for 5h; Product distribution / selectivity;	96.7%
In paraffin at 100 - 140℃; for 3h; Product distribution / selectivity;	63.3%

tri(n-butyl)aluminium (1116-70-7) + tris(dimethylamino)stibine (7289-92-1) → {(C4H9)2AlN(CH3)2}2 + tributylstibine (2155-73-9)

Conditions	Yield
In neat (no solvent) under N2; Al-compd. added slowly over a period of 2 h to Sb-compd. at 0°C with stirring, warmed slowly to room temp., stirred for 4 h, heated for 12 h at 120°C;; monitored by NMR, fractional distn., Al-compd. isolated by distn.;;	A 95% B 87%
In benzene-d6 addn. of Al-compd. to soln. of Sb-compd. in a NMR tube;; not isolated, monitored by 1H-, 13C-NMR spectroscopy;;

tri(n-butyl)aluminium (1116-70-7) + dibenzylamine (103-49-1) → [(C4H9)2AlN(CH2C6H5)2]2

Conditions	Yield
In pentane dry argon, Schlenk setup, nearly 1:1 mixt., pentane evapd., heated to 110°C; recrystd. (hexane, -15°C), elem. anal.;	95%

tri(n-butyl)aluminium (1116-70-7) + N-tert-butylbenzylamine (3378-72-1) → [C4H9AlC4H9NCH2C6H4]2

Conditions	Yield
In toluene ligand in toluene and Al-salt in toluene were mixed in tube at room temp. under inert atm., heated at 120°C for 1 d, cooled to room temp.; cooled to -15°C; elem. anal.;	93%

(1R,2R)-trans-N-phthaloyl-1,2-diaminocyclohexane (216586-53-7) + tri(n-butyl)aluminium (1116-70-7) → C30H38N2O4

Conditions	Yield
In toluene at -10 - 110℃; for 2h; Inert atmosphere;	92.3%
In toluene at -10 - 110℃; for 2h; Inert atmosphere;	92.3%

tri(n-butyl)aluminium (1116-70-7) + Methanesulfonic acid (S)-1-[5,5-dimethyl-2-((Z)-5-phenyl-pent-1-enyl)-[1,3]dioxan-2-yl]-ethyl ester (105378-00-5) → 2-Butyl-5,5-dimethyl-2-((Z)-(S)-1-methyl-6-phenyl-hex-2-enyl)-[1,3]dioxane (105378-07-2)

Conditions	Yield
With n-butyllithium In hexane; dichloromethane at -18 - -15℃; for 3h;	92%

tri(n-butyl)aluminium (1116-70-7) + tin(IV) chloride (7646-78-8) → tetra-n-butyltin(IV) (1461-25-2)

Conditions	Yield
In dibutyl ether	90%
In dibutyl ether	90%
In hexane; pentane	74.7%

cobaltocenium chloride + tri(n-butyl)aluminium (1116-70-7) → {(C5H5)2Co}(1+)*{(C4H9)3AlCl}(1-)={(C5H5)2Co}{(C4H9)3AlCl}

Conditions	Yield
In diethyl ether dropping of ethereal soln. of Al compd. into suspn. of Co complex at 20°C; elem. anal.;	90%

Benzyl-isopropyl-amin (102-97-6) + tri(n-butyl)aluminium (1116-70-7) → [(C4H9)2AlN(CH(CH3)2)CH2C6H5]2 (488099-05-4, 487011-02-9)

Conditions	Yield
In toluene vac. line technique; mixt. of Al compd. (1 equiv.) and amine (1 equiv.) in toluene was heated at 80-100°C for 12-36 h; NMR monitoring;	90%

antimony(III) trioxide + tri(n-butyl)aluminium (1116-70-7) → tributylstibine (2155-73-9)

Conditions	Yield
In hexane molar ratio of Al(C4H9)3 and Sb2O3 = 3 : 1, 1 to 2 h, 60°C; distn.;	87%
In hexane molar ratio of Al(C4H9)3 and Sb2O3 = 3 : 1, 1 to 2 h, 60°C; distn.;	87%

dibutylmagnesium (1191-47-5) + tri(n-butyl)aluminium (1116-70-7) → (C4H9)2AlOMgC4H9 (84560-31-6)

Conditions	Yield
With water In n-heptane H2O add. (medical syringe, 4-6 h, 30-40°C) into Al- and Mg-compds. (molar ratio Al:Mg=1:1) soln.; soln. sepn. from ppt., heptane driving off (30-40°C, 1-5 mm); elem. anal.;	86.7%

C24H36O5Si + tri(n-butyl)aluminium (1116-70-7) → C28H46O5Si

Conditions	Yield
Stage #1: tri(n-butyl)aluminium With tertiary butyl chloride In dichloromethane at -78 - 20℃; Stage #2: C24H36O5Si In dichloromethane at -78℃; for 4h; Stage #3: With water; ammonium chloride In dichloromethane regioselective reaction;	86%

tri(n-butyl)aluminium (1116-70-7) + (S)-2-methylsulfonyloxy-1-(4-methoxyphenyl)-1-propanone 2,2-dimethyl-trimethylene acetal (103593-55-1) → 2-Butyl-2-[(S)-1-(4-methoxy-phenyl)-ethyl]-5,5-dimethyl-[1,3]dioxane (105378-05-0)

Conditions	Yield
With n-butyllithium In hexane; dichloromethane at -15 - 0℃; for 15h;	84%

2-Methoxynaphthalene (93-04-9) + tri(n-butyl)aluminium (1116-70-7) → 2-butylnaphthalene (1134-62-9)

Conditions	Yield
Stage #1: 2-Methoxynaphthalene With bis(1,5-cyclooctadiene)nickel (0); 1,2-bis-(dicyclohexylphosphino)ethane In di-isopropyl ether; toluene at 20℃; for 0.0833333h; Glovebox; Inert atmosphere; Stage #2: tri(n-butyl)aluminium In di-isopropyl ether; toluene at 100℃; for 72h; Glovebox; Inert atmosphere;	84%

N,N'-ethylenediphthalimide (607-26-1) + tri(n-butyl)aluminium (1116-70-7) → C30H39AlN2O4

Conditions	Yield
In toluene at -10 - 110℃; for 1h; Inert atmosphere;	83.4%

C30H38N2O4 + tri(n-butyl)aluminium (1116-70-7) → C34H45AlN2O4

Conditions	Yield
In toluene at -5 - 80℃; for 2h; Inert atmosphere;	83%
In toluene at -10 - 110℃; for 1h; Inert atmosphere;	83%

C26H32N2O4 + tri(n-butyl)aluminium (1116-70-7) → C30H39AlN2O4

Conditions	Yield
In toluene at -5 - 90℃; for 2h; Inert atmosphere;	81.5%
In toluene at -5 - 90℃; for 2h; Inert atmosphere;	81.5%
In toluene at -5 - 90℃; for 2h; Inert atmosphere;	81.5%

(1R,2R)-trans-N-phthaloyl-1,2-diaminocyclohexane (216586-53-7) + tri(n-butyl)aluminium (1116-70-7) → C34H45AlN2O4

Conditions	Yield
In hexane at 0 - 100℃; for 1h; Inert atmosphere;	81.5%
In toluene at 0 - 110℃; for 1h; Inert atmosphere;	81.5%

tri(n-butyl)aluminium (1116-70-7) + 2,2-diethyl-4,6-diphenyl-2H-pyran (113519-65-6) → (6E)-9-ethyl-5,7-diphenylundeca-6,8-dien-5-ol (113519-74-7)

Conditions	Yield
In benzene at 25℃; for 2h;	80%

N,N'-ethylenediphthalimide (607-26-1) + tri(n-butyl)aluminium (1116-70-7) → C26H32N2O4

Conditions	Yield
In hexane at 0 - 40℃; for 12h; Inert atmosphere;	79.6%
Stage #1: N,N'-ethylenediphthalimide; tri(n-butyl)aluminium In hexane at 0 - 40℃; for 12h; Inert atmosphere; Stage #2: With water In hexane Inert atmosphere;	79.6%
In hexane at 0 - 40℃; for 12h; Inert atmosphere;	79.6%

4-chloro-2H-1-benzopyran-2-one (17831-88-8) + tri(n-butyl)aluminium (1116-70-7) → (Z)-5-butyl-7-(o-hydroxyphenyl)undec-6-en-5-ol (145982-74-7)

Conditions	Yield
In toluene for 20h; 1.) -50 deg C, 30 min, 2.) -> room temperature;	79%

3-chloro-2H-chromen-2-one (92-45-5) + tri(n-butyl)aluminium (1116-70-7) → (E)-2-chloro-1-(o-hydroxyphenyl)hept-1-en-3-ol (133380-25-3) + (E)-3-butyl-2-chloro-1-(o-hydroxyphenyl)hept-1-en-3-ol (133380-17-3)

Conditions	Yield
In toluene at 0℃; for 10h;	A 78% B 7%

3-bromo-2H-chromen-2-one (939-18-4) + tri(n-butyl)aluminium (1116-70-7) → (E)-2-bromo-1-(o-hydroxyphenyl)hept-1-en-3-ol (133380-28-6) + (E)-2-bromo-3-butyl-1-(o-hydroxyphenyl)hept-1-en-3-ol (133380-21-9)

Conditions	Yield
In toluene at 0℃; for 10h;	A 78% B 5%

tri(n-butyl)aluminium (1116-70-7) + (E)-N-benzylidenebenzenamine (1750-36-3, 33993-35-0, 538-51-2, 137431-97-1, 137432-04-3) → N-Benzylaniline (758640-21-0) + N-phenyl-(1-phenylpentyl)amine (62740-72-1)

Conditions	Yield
With zirconocene dichloride In dichloromethane at 10℃; for 24h;	A 20% B 75%

iodobenzene (591-50-4) + tert-butylisonitrile (119072-55-8, 7188-38-7) + tri(n-butyl)aluminium (1116-70-7) → Phenyl-1,2-hexanedione (33720-29-5)

Conditions	Yield
Stage #1: iodobenzene; tert-butylisonitrile; tri(n-butyl)aluminium With 1,3-bis-(diphenylphosphino)propane; palladium dichloride In toluene at 20℃; for 0.0833333h; Sealed tube; Inert atmosphere; Stage #2: With potassium tert-butylate In toluene at 20 - 100℃; for 16h; Sealed tube; Inert atmosphere; Stage #3: With hydrogenchloride; water In toluene at 20℃; for 1h; Sealed tube; Inert atmosphere;	75%

dibutylmagnesium (1191-47-5) + tri(n-butyl)aluminium (1116-70-7) → C4H9MgOAl(C4H9)OMgC4H9 (84584-28-1)

Conditions	Yield
With water In n-heptane byproducts: butane; H2O add. (medical syringe, 4-6 h, 30-40°C) into Al- and Mg-compds. (molar ratio Al:Mg=1:2) soln.; soln. sepn. from ppt., heptane driving off (30-40°C, 1-5 mm); elem. anal.;	72.3%

tri(n-butyl)aluminium (1116-70-7) + 4-methoxy-N-[(E)-phenylmethylidene]aniline (1613-90-7) → benzyl(4-methoxyphenyl)amine (17377-95-6) + N-(4-methoxyphenyl)-α-butylbenzenemethaneamine (132554-75-7)

Conditions	Yield
With zirconocene dichloride In dichloromethane at 10℃; for 24h;	A 22% B 71%

Upstream product

• 7446-70-0 aluminum (III) chloride 
• 109-72-8 n-butyllithium 
• 542-69-8 1-iodo-butane 
• 109-65-9 1-bromo-butane 
• 100-66-3 methoxybenzene 
• 1191-47-5 dibutylmagnesium 

Downstream Products

• 109-21-7 butyl butyrate 
• 122-97-4 3-Phenyl-1-propanol 
• 7500-73-4 (±)-2-benzyl-1-hexanol 
• 133380-25-3 (E)-2-chloro-1-(o-hydroxyphenyl)hept-1-en-3-ol 
• 133380-17-3 (E)-3-butyl-2-chloro-1-(o-hydroxyphenyl)hept-1-en-3-ol 
• 133380-28-6 (E)-2-bromo-1-(o-hydroxyphenyl)hept-1-en-3-ol 
• 133380-21-9 (E)-2-bromo-3-butyl-1-(o-hydroxyphenyl)hept-1-en-3-ol 
• 30506-37-7 butyl-4-(tert-butyl)phenyl sulfane 
• 995-43-7 methyl-tri-n-butylsilane 
• 17582-53-5 butyltriethylstannane 
• 2155-73-9 tributylstibine 
• 30191-25-4 (tert-C₄H₉)3SnC₄H₉ 
• 871-89-6 dibutylaluminum hydride 
• 281666-89-5 [n-BuAlN(CH2Ph)-μ-(CH2C6H4)]2 

Related news

The Monomer—Dimer Equilibria of liquid Aluminum Alkyls : V. Tri-n-Propylaluminum, TRI-N-BUTYLALUMINUM (cas 1116-70-7) and Tri-n-Octylaluminum: The effect of chain length on the equilibria09/09/2019

The monomer—dimer equilibria of three liquid aluminum n-alkyls have been studied in n-hexadecane solution by a thermochemical method applied earlier to triethylaluminum (TEA) and triisobutylaluminum (TiBA). The values obtained for the heat and entropy of dissociation of 1 mole of dimer are: for...detailed

Relevant articles and documents

Facile high-yield synthesis of pure, crystalline Mg(BH4) 2

Magnesium borohydride, Mg(BH4)2, a long-sought candidate for efficient hydrogen storage chemisorption technology, has been obtained in a pure and crystalline form by two new synthetic routes in a hydrocarbon solvent. A first synthetic approach involves a metathetical reaction between organometallic magnesium compounds; a second route consists of an insertion reaction of BH3 species, released from BH 3·S(CH3)2, into the Mg-C bonds of MgR2, with complete replacement of R groups with BH4 groups. Both methods, based on commercially available reagents, afford identical, pure, polycrystalline materials, identified by X-ray diffraction as the so-called low-temperature hexagonal form of Mg(BH4)2, stable below 180°C, recently shown to possess a complex, unpredictable, crystal structure.

Discrete Organofluoroaluminate Anions: Synthetic, Structural, and Spectroscopic Aspects

The reaction of alkylaluminum compounds (AlR3, R = Me, n-Bu) with the series of imidazolium-based fluorinating reagents [IPrH][F], [IPrH][(HF)F] and [IPrH][(HF)2F] led to the isolation of salts containing discrete triorganofluoroaluminate ([R3AlF]-), diorganodifluoroaluminate ([R2AlF2]-), and organotrifluoroaluminate ([RAlF3]-) anions, respectively. The formation of [R2AlF2]- and [RAlF3]- anions was accompanied by the release of RH. The syntheses are effective, selective, and straightforward. The related reactions of an arylaluminum compound (AlPh3) resulted in a mixture of different phenylfluoroaluminate anions. All of the obtained products were characterized by NMR and Raman spectroscopy. Structural features of [IPrH][Me2AlF2] (2), [IPrH][MeAlF3] (3), [IPr][AlF4] (4), [IPrH][n-Bu3AlF] (5), [IPrH][n-Bu2AlF2] (6), [IPrH][n-BuAlF3] (7), [IPrH][Ph3AlF] (8), and [IPrH][PhAlF3] (10) were determined by single-crystal X-ray diffraction and compared with DFT calculations of structurally optimized salts.