75-24-1

Basic information

• Product Name: Trimethylaluminium
• Synonyms: Trimethylaluminum, min. 98%(Material sold in non-returnable cylinder);TriMethylaluMinuM, 2M in Hexane;TriMethylaluMinuM, 1.0 M solution in hexanes, J&KSeal;TriMethylaluMinuM, 1.0 M solution in heptane, J&KSeal;TriMethylaluMinuM solution 2.0 M in chlorobenzene;TriMethylaluMinuM solution 2.0 M in toluene;TriMethylaluMinuM, 1.0 M solution in hexanes, SpcSeal;TriMethylaluMinuM, 2.0 M solution in toluene, SpcSeal
• CAS NO: 75-24-1
• Molecular Formula: C₃H₉Al
• Molecular Weight: 72.09
• EINECS: 200-853-0
• Product Categories: metal alkyl;Chemical Synthesis;Organometallic Reagents;Aluminum;CVD and ALD Precursors by Metal;Materials Science;Micro/NanoElectronics;Vapor Deposition Precursors;ALD Precursors;Organometallics;Al (Alminum) Compounds;Alkyl Metals;Classes of Metal Compounds;Grignard Reagents & Alkyl Metals;Synthetic Organic Chemistry;Typical Metal Compounds;Chemical Synthesis;Organoaluminum;Organometallic Reagents
• Mol File: 75-24-1.mol

Chemical Properties

• Melting Point: 15 °C
• Boiling Point: 126 °C
• Flash Point: 40 °F
• Appearance: Clear colorless/Liquid
• Density: 0.81 g/mL at 25 °C
• Vapor Pressure: 69.3 mmHg ( 60 °C)
• Storage Temp.: 0-6°C
• Solubility: Soluble in aromatic, saturated aliphatic and cycloaliphatic hydr
• Water Solubility: REACTS
• Sensitive: Air & Moisture Sensitive
• BRN: 3587197
• CAS DataBase Reference: Trimethylaluminium(CAS DataBase Reference)
• NIST Chemistry Reference: Trimethylaluminium(75-24-1)
• EPA Substance Registry System: Trimethylaluminium(75-24-1)

Safety Data

• Hazard Codes: F,C,N
• Statements: 11-14-17-34-50/53-65-67-14/15-63-48/20-51/53-20-62
• Safety Statements: 26-36/37/39-45-61-62-6A-43A-24/25-16-43-60-33-25-24
• RIDADR: UN 3399 4.3/PG 1
• WGK Germany: 3
• RTECS: BD2204000
• F: 1-10
• TSCA: Yes
• HazardClass: 4.3
• PackingGroup: I
• Hazardous Substances Data: 75-24-1(Hazardous Substances Data)

Usage

Outline

Trimethylaluminum is called TMA for short. Trimethylaluminum was prepared by Buckton for the first time using methyl mercury and aluminum in 1865, but until the 1950s, TMA applications has been still limited to the scope of laboratory, its research and application was far less active than organic magnesium and organic lithium for a long time. In recent years, with the development of the research of polyolefins, TMA is as one of the cocatalyst, and starting raw materials for synthesis of cocatalyst catalysts methylalumoxane (of MAO) and modified methylaluminoxane (MMAO) in metallocene catalyst systems. In the organic chemical industry, especially polymer chemical industry, its importance began to appear. At normal temperature and pressure, trimethyl aluminum is a colorless transparent liquid, highly reactive, spontaneous combustion in the air, and instantly be able to fire, reacts violently with alcohol and acids which have an active hydrogen, reacts violently with water, even in cold water explosive decomposition reaction can be produced, and also generates methane, and sometimes can catch fire. At 300 ℃ it slowly decompose to produce methane. It can form stable complexes with AsH3, PH3, ethers, tertiary amines and other Lewis bases, miscible in any proportion with alicyclic hydrocarbons such as hexane and heptane, aromatic hydrocarbon such as toluene, xylene. diluted to below 25% with a hydrocarbon-based solvent, trimethyl aluminum loses its spontaneous combustion.

Main application

There is an important use for trimethyl aluminum in organic catalytic chemistry, organic synthesis and polymer chemistry industry and other aspects. Trimethylaluminum acts with water of a suitable form, may form highly reactive methylaluminoxane (MAO), which is one of the most important co-catalyst of the metallocene catalyst system. The maximum use of MAO is to form a coordination catalyst, such as with the halide of titanium, zirconium, hafnium to form a catalyst system, which can result in stereospecific polymerization, copolymerization, oligomerization of olefins. It can form catalyst with the compound of transition metal element such as nickel, cobalt, etc, which can result in lower poly, disproportionation, isomerization of olefins. Further, trimethyl aluminum itself may be used to catalyze the reaction. TMA can be carried out oligomerization with ethylene to produce high-carbon aluminum alkyl, after oxidation and hydrolysis of the latter to form a straight-chain higher primary alcohols and advanced a-olefins. Organoaluminum is not only inexpensive, but also has high reaction activity, thus organoaluminum is commonly used for preparing other metals organic compounds, for example the reaction of TMA with stannic chloride can be prepared to produce methyl tin. TMA can also be used as mild reducing agent for high stereoselectivity reagents, vitamins, hormones and other drug synthetic. In recent years, the formation of a metal film is achieved by application of metal organic chemical vapor deposition method. As with the hydrogen carrying TMA, the substrate is heated for thermal decomposition to form a metal thin film of aluminum. In the aerospace industry, and trimethyl aluminum can be used as liquid fuel of rockets. TMA can also be used as an important alkylating agent in organic synthesis of fine chemical industry. As olefin polymerization catalyst, pyrophoric fuel, also used for making straight-chain primary alcohols and olefins, etc, it can be used for metal organic chemical vapor deposition. The above information is edited by the lookchem of Yan Yanyong.

Category

Spontaneous Combustion items

Acute toxicity

Oral-rat LD50: 10000 mg/cubic meter/15 minutes

Flammability hazard characteristics

In case of air, chlorine, oxidizers, high temperature can be spontaneous, emit toxic aluminide gases.

Storage Characteristics

Treasury ventilation low-temperature drying, package with nitrogen charging, and stored separately from oxidants

Extinguishing agent

Dry sand, powder, mountain flour

Occupational standards

TWA 2 mg(AL)/cubic meter

Uses

Different sources of media describe the Uses of 75-24-1 differently. You can refer to the following data:
1. Trimethylaluminium can be used as catalyst for olefin polymerization, pyrophoric fuel, manufacture of straight-chain primary alcohols and olefins, to produce luminous trails in upper atmosphere to track rockets.
2. Trimethyl aluminum is a highly reactivereducing and alkylating agent. It is used in aZiegler-Natta catalyst for polymerization andhydrogenation.
3. Trimethylaluminum can be used in the pretreatment of Al2O3/p-type GaSb capacitors.

Definition

A colorless liquid produced by the sodium reduction of dimethyl aluminum chloride. It ignites spontaneously on contact with air and reacts violently with water, acids, halogens, alcohols, and amines. Aluminum alkyls are used in the Ziegler process for the manufacture of high-density polyethene.

Health Hazard

Different sources of media describe the Health Hazard of 75-24-1 differently. You can refer to the following data:
1. As it is pyrophoric and reacts explosivelywith moisture, skin contact can cause a dangerousburn. Contact with eyes can causeblindness. Because of its significant volatility,the risk of inhalation of this compoundis higher than with most other alkyls. Inhalationof its vapors can severely damage therespiratory tract.TLV-TWA: 2 mg(Al)/m3 (ACGIH).
2. Trimethylaluminum and related alkylaluminum reagents are pyrophoric materials that can react explosively with the moisture in tissues, causing severe burns. The heat of reaction can also ignite the methane gas generated, resulting in thermal burns. Alkylaluminum reagents are corrosive substances, and contact is extremely destructive to the eyes, skin, and mucous membranes. Inhalation of trimethylaluminum and other volatile alkylaluminum compounds may cause severe damage to the respiratory tract and can lead to fatal pulmonary edema.

Flammability and Explosibility

Trimethylaluminum is pyrophoric and burns violently on contact with air or water. Other alkylaluminum reagents show similar behavior, although most are not as volatile as trimethylaluminum. Water or CO2 fire extinguishers must not be used to put out fires involving trialkylaluminum reagents. Instead, dry chemical powders such as bicarbonate, Met-L-X?, or inert smothering agents such as sand or graphite should be used to extinguish fires involving trialkylaluminum compounds.

storage

Safety glasses, impermeable gloves, and a fire-retardant laboratory coat should be worn at all times when working with these compounds. Trialkylaluminum reagents should be handled only under an inert atmosphere.

InChI:InChI=1/3CH3.Al/h3*1H3;/rC3H9Al/c1-4(2)3/h1-3H3

Synthetic route

aluminium trichloride (7446-70-0) → trimethylaluminum (75-24-1)

Conditions	Yield
With methylmagnesium bromide In not given react. of AlCl3 with MeMgBr;	99%

gallium (7440-55-3) + methyl aluminium sesquichloride → trimethylaluminum (75-24-1) + trimethyl gallium (1445-79-0)

Conditions	Yield
With methylene chloride; sodium at 40 - 50℃; under 375.038 Torr; Inert atmosphere; Flow reactor;	A 93.7% B 96.8%

triethylaluminum (97-93-8) + aluminium (7429-90-5) → trimethylaluminum (75-24-1) + diethylaluminum iodide (2040-00-8)

Conditions	Yield
With iodine; methyl iodide In ethanol Sonication; N2; CH3I, I2 and Al introduced in a condenser with C2H5OH at -20°C, ultrasonic acceleration at room temp. for 2 h, Et3Al (ratio MeI/Et3Al = 1.50) dropped into soln. within 10 min, sonication for 30 min; distilled (vac.);	A 86% B 95%

neodymium tetramethylaluminate + 2,4,6-tri-tert-butylbenzoic acid (66415-27-8) → (Nd((2,4,6-tri-tert-butylbenzoate)[(μ-Me)2AlMe2]2)2 + trimethylaluminum (75-24-1)

Conditions	Yield
In hexane; toluene byproducts: CH4; in a glovebox, Nd-contg. compd. (0.50 mmol) was dissolved in hexane, anda toluene suspn. of carboxylic acid (0.50 mmol) was slowly added; stirr ing at ambient temp. for 18 h; the solvent was removed in vac.; extn. in toluene; the complex was washed with hexane and dried for several hours; elem. anal.;	A 94% B n/a

triethylaluminum (97-93-8) + aluminium (7429-90-5) → trimethylaluminum (75-24-1) + dimethyl aluminum iodide (2938-72-9) + ethyl aluminium iodide (2938-73-0)

Conditions	Yield
With iodine; methyl iodide In ethanol Sonication; N2, CH3I, I2 and Al introduced in a condenser with C2H5OH at -20°C, ultrasonic acceleration at room temp. for 2 h, Et3Al (ratio MeI/Et3Al = 12.00) dropped into soln. within 10 min, sonicated for 30 min; distilled (vac.);	A 62.5% B 22.5% C 93%

lanthanum tetramethylaluminate + 2,4,6-tri-tert-butylbenzoic acid (66415-27-8) → (La((2,4,6-tri-tert-butylbenzoate)[(μ-Me)2AlMe2]2)2 + trimethylaluminum (75-24-1)

Conditions	Yield
In hexane; toluene byproducts: CH4; in a glovebox, La-contg. compd. (0.50 mmol) was dissolved in hexane, anda toluene suspn. of carboxylic acid (0.50 mmol) was slowly added; stirr ing at ambient temp. for 18 h; the solvent was removed in vac.; extn. in toluene; the complex was washed with hexane and dried for several hours; elem. anal.;	A 93% B n/a

lanthanum tetramethylaluminate + 1,2,3,4,5-pentamethylcyclopentadiene (4045-44-7) → (1,2,3,4,5-pentamethylcyclopentadienyl)bis(tetramethylaluminato)lanthanum(III) + trimethylaluminum (75-24-1)

Conditions	Yield
In hexane byproducts: CH4; Schlenk technique; diene (1 equiv.) in hexane was added with stirring tosoln. of La complex in hexane; mixt. was stirred for 5 min; solvent removed (vac.); dried (vac.); elem. anal.;	A 93% B n/a

neodymium tetramethylaluminate + 1,2,3,4,5-pentamethylcyclopentadiene (4045-44-7) → (1,2,3,4,5-pentamethylcyclopentadienyl)bis(tetramethylaluminato)neodymium(III) + trimethylaluminum (75-24-1)

Conditions	Yield
In hexane byproducts: CH4; Schlenk technique; diene (1 equiv.) in hexane was added with stirring tosoln. of Nd complex in hexane; mixt. was stirred for 5 min; solvent removed (vac.); dried (vac.); elem. anal.;	A 91% B n/a

tris(η2-tetramethylaluminato)lutetium(III) + 1,2,3,4,5-pentamethylcyclopentadiene (4045-44-7) → (1,2,3,4,5-pentamethylcyclopentadienyl)bis(tetramethylaluminato)lutetium(III) + trimethylaluminum (75-24-1)

Conditions	Yield
In hexane byproducts: CH4; Schlenk technique; diene (1 equiv.) in hexane was added with stirring tosoln. of Lu complex in hexane; mixt. was stirred for 5 min; solvent removed (vac.); dried (vac.); elem. anal.;	A 91% B n/a

tris(η2-tetramethylaluminato)yttrium(III) + 2,4,6-tri-tert-butylbenzoic acid (66415-27-8) → (Y((2,4,6-tri-tert-butylbenzoate)[(μ-Me)2AlMe2]2)2 + trimethylaluminum (75-24-1)

Conditions	Yield
In hexane; toluene byproducts: CH4; in a glovebox, Y-contg. compd. (0.50 mmol) was dissolved in hexane, and a toluene suspn. of carboxylic acid (0.50 mmol) was slowly added; stirring at ambient temp. for 18 h; the solvent was removed in vac.; extn. in toluene; the complex was washed with hexane and dried for several hours; elem. anal.;	A 87% B n/a

methylene chloride (74-87-3) + dimethylaluminum chloride (1184-58-3) → trimethylaluminum (75-24-1)

Conditions	Yield
With sodium; copper In Hexadecane at 20 - 130℃; under 825.083 - 862.586 Torr; for 2.2h; Inert atmosphere; Flow reactor;	87%
With sodium In melt; 1,3,5-trimethyl-benzene at 100 - 120℃; under 7.50075 Torr; for 6h; Inert atmosphere;	69.5 g

methylene chloride (74-87-3) + methylaluminum dichloride (917-65-7) → trimethylaluminum (75-24-1)

Conditions	Yield
With sodium; gold In Hexadecane at 20 - 130℃; under 825.083 - 862.586 Torr; for 2.2h; Inert atmosphere; Flow reactor;	87%
With sodium In melt; 1,3,5-trimethyl-benzene at 80 - 120℃; under 7.50075 Torr; for 8h; Inert atmosphere;	68.4 g

methyl iodide (74-88-4) + methylaluminum sesquichloride → trimethylaluminum (75-24-1)

Conditions	Yield
Stage #1: methyl iodide With magnesium In diethyl ether at 15℃; for 1h; Inert atmosphere; Stage #2: methylaluminum sesquichloride In pentane at 20℃; for 4h; Inert atmosphere;	87%

methylene chloride (74-87-3) + methylaluminum sesquichloride → trimethylaluminum (75-24-1)

Conditions	Yield
With silver; sodium In Hexadecane at 20 - 130℃; under 825.083 - 862.586 Torr; for 2.2h; Temperature; Inert atmosphere; Flow reactor;	87%

tris(η2-tetramethylaluminato)yttrium(III) + 1,2,3,4,5-pentamethylcyclopentadiene (4045-44-7) → (1,2,3,4,5-pentamethylcyclopentadienyl)bis(tetramethylaluminato)yttrium(III) + trimethylaluminum (75-24-1)

Conditions	Yield
In hexane byproducts: CH4; Schlenk technique; diene (1 equiv.) in hexane was added with stirring tosoln. of Y complex in hexane; mixt. was stirred for 5 min; solvent removed (vac.); dried (vac.); elem. anal.;	A 86% B n/a

(CH2)3(P(C6H5)2Al(CH3)3)2*2C6H6 → trimethylaluminum (75-24-1)

Conditions	Yield
In neat (no solvent) metal complex decomposed at 120-140°C for 2-3 h;	86%

triethylaluminum (97-93-8) + aluminium (7429-90-5) → trimethylaluminum (75-24-1)

Conditions	Yield
With iodine; methyl iodide In ethanol Sonication; N2, CH3I, I2 and Al introduced in a condenser with C2H5OH at -20°C, ultrasonic acceleration at room temp. for 2 h, Et3Al (ratio MeI/Et3Al = 0.75) dropped into soln. within 10 min, sonicated for 30 min; distilled (vac.);	85%

methyl bromide (74-83-9) + methylaluminum sesquichloride → trimethylaluminum (75-24-1)

Conditions	Yield
Stage #1: methyl bromide With magnesium In tetrahydrofuran at 60℃; for 4h; Inert atmosphere; Stage #2: methylaluminum sesquichloride In hexane at 40℃; for 6h; Inert atmosphere;	85%

(triphenylphosphine)trimethylaluminum → trimethylaluminum (75-24-1)

Conditions	Yield
In neat (no solvent) metal complex decomposed at 120-130°C for 2-3 h;	84%

aluminium(III) iodide + methyl iodide (74-88-4) → trimethylaluminum (75-24-1)

Conditions	Yield
Stage #1: methyl iodide With magnesium In diethyl ether at 15℃; for 1h; Inert atmosphere; Stage #2: aluminium(III) iodide In pentane at 30℃; for 4h; Inert atmosphere;	81%

methylene chloride (74-87-3) + methylaluminum sesquichloride → trimethylaluminum (75-24-1)

Conditions	Yield
Stage #1: methylene chloride With magnesium at 80℃; for 6h; Inert atmosphere; Stage #2: methylaluminum sesquichloride at 60℃; for 8h; Inert atmosphere;	81%

(CH2)5(P(C6H5)2Al(CH3)3)2 → trimethylaluminum (75-24-1)

Conditions	Yield
In neat (no solvent) metal complex decomposed at 120-140°C for 2-3 h;	80%

methyl bromide (74-83-9) + aluminum tri-bromide → trimethylaluminum (75-24-1)

Conditions	Yield
Stage #1: methyl bromide With magnesium In tetrahydrofuran at 40℃; for 3h; Inert atmosphere; Stage #2: aluminum tri-bromide In hexane at 40℃; for 7h; Inert atmosphere;	79%

methyl aluminium sesquichloride → trimethylaluminum (75-24-1)

Conditions	Yield
With sodium In mineral oil at 120 - 140℃; under 19.502 Torr; for 5.5h; Inert atmosphere;	76.7%

triethylaluminum (97-93-8) + aluminium (7429-90-5) → trimethylaluminum (75-24-1) + dimethyl aluminum iodide (2938-72-9)

Conditions	Yield
With iodine; methyl iodide In ethanol Sonication; N2, CH3I, I2 and Al introduced in a condenser with C2H5OH at -20°C, ultrasonic acceleration at room temp. for 2 h, Et3Al (ratio MeI/Et3Al = 3.00) dropped into soln. within 10 min, sonicated for 30 min; distilled (vac.);	A 76% B 11.2%
With iodine; methyl iodide In ethanol Sonication; N2, CH3I, I2 and Al introduced in a condenser with C2H5OH at -20°C, ultrasonic acceleration at room temp. for 2 h, Et3Al (ratio MeI/Et3Al = 6.00) dropped into soln. within 10 min, sonicated for 30 min; distilled (vac.);	A 65% B 15.7%

aluminum (III) chloride (7446-70-0, 7784-13-6) + methylene chloride (74-87-3) → trimethylaluminum (75-24-1)

Conditions	Yield
Stage #1: methylene chloride With magnesium In tetrahydrofuran at 60℃; for 6h; Inert atmosphere; Stage #2: aluminum (III) chloride In hexane at 50℃; for 11h; Inert atmosphere;	76%

2,2,7,7-tetramethyl-octa-3,5-diyne (6130-98-9) + dimethylaluminum hydride (865-37-2) → Al4H3(CH3)6((CH3)3CCCHCCH2C(CH3)3) + trimethylaluminum (75-24-1)

Conditions	Yield
In neat (no solvent) under Ar atm. excess Me2AlH and di(tert-butyl)butadiyne were stirred at 100°C for 1.5 h; react. mixt. was cooled to room temp., volatiles were removed in vacuo, residue was dissolved in n-pentane and cooled to -15°C;	A 70% B n/a

methylene chloride (74-87-3) + Reaxys ID: 23508781 + dimethylaluminum chloride (1184-58-3) → trimethylaluminum (75-24-1)

Conditions	Yield
Stage #1: dimethylaluminum chloride With pyridine; iodine In dodecane at 40℃; for 1.5h; Autoclave; Stage #2: methylene chloride In dodecane at 130℃; for 24h; Temperature; Reagent/catalyst;	70%

tris(η2-tetramethylaluminato)yttrium(III) + [1,1':3',1''-terphenyl]-2'-carboxylic acid (5547-35-3) → (Y((2,6-diphenylbenzoate)[(μ-Me)2AlMe2]2)2 + trimethylaluminum (75-24-1)

Conditions	Yield
In hexane; toluene byproducts: CH4; in a glovebox, Nd-contg. compd. (0.40 mmol) was dissolved in hexane, anda toluene suspn. of carboxylic acid (0.40 mmol) was slowly added; stirr ing at ambient temp. for 18 h; the solvent was removed in vac.; extn. in toluene; the complex was washed with hexane and dried for several hours; purifn. by crystn.; elem. anal.;	A 64% B n/a

1-chloro-4-trimethylsilyl but-3-yne (58435-00-0) + trimethylaluminum (75-24-1) → 2-methyl-1-(trimethylsilyl)cyclobutene (86994-12-9)

Conditions	Yield
With zirconocene dichloride In dichloromethane at 25℃; for 24h;	100%
With zirconocene dichloride In dichloromethane at 25℃; for 24h;	95 % Chromat.

4-iodo-1-butynyltrimethylsilane (41423-29-4) + trimethylaluminum (75-24-1) → 2-methyl-1-(trimethylsilyl)cyclobutene (86994-12-9)

Conditions	Yield
With zirconocene dichloride In dichloromethane at 25℃; for 24h;	100%
With zirconocene dichloride In dichloromethane at 25℃; for 24h;	85%

trimethylaluminum (75-24-1) + (S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-6-oxo-hexanoic acid methyl ester (156479-95-7) → (S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-6-hydroxy-heptanoic acid methyl ester

Conditions	Yield
In hexane; dichloromethane at 0℃;	100%

trans-chrotonyl chloride (625-35-4, 3488-22-0, 10487-71-5) + trimethylaluminum (75-24-1) → trans-3-penten-2-one (3102-33-8)

Conditions	Yield
With aluminium trichloride In dichloromethane for 2h; Ambient temperature;	100%
With aluminium trichloride 1.) CH2Cl2, 1 h, 2.) CH2Cl2, room temperature, 2 h; other reagents: GaCl3, AlF3; Yield given. Multistep reaction;

5-hexyl-1-ol (928-90-5) + trimethylaluminum (75-24-1) → 5-methylhex-5-en-1-ol (5212-80-6)

Conditions	Yield
With zirconocene dichloride In hexane; 1,2-dichloro-ethane at 20℃; for 22h; Addition;	100%

trimethylaluminum (75-24-1) + (R)-1,4-Dioxa-spiro[4.5]decane-2-carboxylic acid (2S,3R)-2-(2-benzyloxy-ethyl)-tetrahydro-pyran-3-yl ester (286958-06-3) → (R)-2-{1-[(2S,3R)-2-(2-Benzyloxy-ethyl)-tetrahydro-pyran-3-yloxy]-vinyl}-1,4-dioxa-spiro[4.5]decane (286958-07-4)

Conditions	Yield
Stage #1: trimethylaluminum With bis(cyclopentadienyl)titanium dichloride In toluene at 23℃; for 72h; complex formation; Stage #2: (R)-1,4-Dioxa-spiro[4.5]decane-2-carboxylic acid (2S,3R)-2-(2-benzyloxy-ethyl)-tetrahydro-pyran-3-yl ester In tetrahydrofuran; toluene at 0 - 23℃; olefination;	100%

trimethylaluminum (75-24-1) + benzaldehyde (100-52-7) → (R)-1-phenylethanol (1517-69-7)

Conditions	Yield
With titanium(IV) isopropylate; (R,S)-2-OH-3,5-Cl2-C6H2-SO2-NH-CH(CH2Ph)-CH(Ph)OH In tetrahydrofuran at 0℃; for 12h;	100%
In tetrahydrofuran; hexane at -20℃; for 3h; Product distribution / selectivity;	60%

trimethylaluminum (75-24-1) + 4,6-O-benzylidene-2,3-bis-O-(tert-butyldimethylsilyl)-D-glucono-1,5-lactone (498554-04-4) → (1R,3R,6R,9R,10S)-9,10-bis(tert-butyldimethylsilyloxy)-8-methylene-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decane (498554-05-5)

Conditions	Yield
Stage #1: trimethylaluminum With titanocene dichloride In toluene at 23℃; for 72h; Stage #2: 4,6-O-benzylidene-2,3-bis-O-(tert-butyldimethylsilyl)-D-glucono-1,5-lactone In tetrahydrofuran; toluene at 0 - 24℃; Tebbe olefination;	100%

trimethylaluminum (75-24-1) + propargyl alcohol (107-19-7) + (1R,2S,5R)-2-isopropyl-5-methylcyclohexanecarboxaldehyde (80434-59-9) → (E)-1-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyl)-3-methyl-but-2-ene-1,4-diol

Conditions	Yield
Stage #1: trimethylaluminum With bis(cyclopentadienyl)dihydrozirconium In dichloromethane for 0.166667h; Stage #2: propargyl alcohol In dichloromethane at 20℃; for 12h; Stage #3: (1R,2S,5R)-2-isopropyl-5-methylcyclohexanecarbaldehyde In tetrahydrofuran; dichloromethane at -78 - 20℃; for 12h;	100%
Stage #1: trimethylaluminum With zirconocene dichloride In dichloromethane at 20℃; for 0.166667h; Stage #2: propargyl alcohol In dichloromethane at 0 - 20℃; Stage #3: (1R,2S,5R)-2-isopropyl-5-methylcyclohexanecarbaldehyde In tetrahydrofuran; dichloromethane at -70 - 20℃;

1,8-dichloro-9-methylanthracene (17122-96-2) + trimethylaluminum (75-24-1) → 1,8,9-trimethylanthracene (63335-10-4)

Conditions	Yield
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In 1,2-dimethoxyethane; hexane for 7h; Heating;	100%

3,3-diphenyloxirane-2-carboxylic acid methyl ester (76527-25-8) + trimethylaluminum (75-24-1) → (+/-)-methyl 2-hydroxy-3,3-diphenylbutanoate (178306-50-8)

Conditions	Yield
In cyclohexane; toluene at 10 - 15℃; for 0.5h; Product distribution / selectivity;	100%
In cyclohexane at 10℃; Product distribution / selectivity;	96%
In n-heptane; toluene at -10℃; for 0.5h; Product distribution / selectivity;	82%
In toluene at -10 - 10℃; Product distribution / selectivity;	82%

trimethylaluminum (75-24-1) → polymethylaluminoxane

Conditions	Yield
With benzoic acid In toluene at 26 - 80℃; for 9.5h;	100%

1,4,7,10-tetrathiacyclododecane (25423-56-7) + trimethylaluminum (75-24-1) → trimethylaluminum-thiacrown ether {12}aneS4 (112440-15-0)

Conditions	Yield
In toluene addn. of Me3Al to {12}aneS4 in abs. toluene , heated at 60°C for several h; solvent reduced in vacuo, cooling;	100%

bis(cyclopentadienyl)titanium dichloride (1271-19-8) + trimethylaluminum (75-24-1) → bis(cyclopentadienyl)methyltitanium(IV) chloride (1278-83-7)

Conditions	Yield
With tetrahydrofuran In benzene-d6; toluene N2 or Ar-atmosphere; stirring (22°C, 1 h), THF addn.; detd. by NMR spectroscopy;	100%

trimethylaluminum (75-24-1) + magnesium bis(N,N-diisopropylamide) → [(CH3)2Al(N(C3H7)2)2Al(CH3)2] + {(CH3)2Al{N(C3H7)2}2Mg(CH3)}4

Conditions	Yield
In diethyl ether; toluene absence of air and moisture; dropwise addn. of AlMe3 in toluene to Mg(N(C3H7)2)2 in Et2O (molar ratio = 1 : 1, room temp., stirring); after 12h removal of solvent (vac.), recrystn. (hexane), sublimation (60°C); elem. anal.;	A <5 B 100%

trimethylaluminum (75-24-1) + triphenylplumbyl hydroxide (894-08-6) → methylaluminoxane + (triphenylplumbyl)methane (3124-28-5)

Conditions	Yield
byproducts: CH4; not isolated, detected by NMR;	A n/a B 100%

trimethylaluminum (75-24-1) + triphenyltin(IV) hydroxide (76-87-9) → methylaluminoxane + triphenyl methyl tin (1089-59-4)

Conditions	Yield
byproducts: CH4; not isolated, detected by NMR;	A n/a B 100%

(CH3)2AlNHCH2CH2N(CH3)2 (102990-34-1) + trimethylaluminum (75-24-1) → (CH3)2Al(NH(Al(CH3)3)CH2CH2N(CH3)2)

Conditions	Yield
In dichloromethane Ar-atmosphere; addn. of Al-compd. (0°C); gradual warming to room temp. (2 h); evapn.;	100%

(CH3)3SiNC(C6H5)CH2C(C6H5)NSi(CH3)3 (912272-65-2) + trimethylaluminum (75-24-1) → [AlMe2(CH(C(Ph)NSiMe3)2)] (226717-58-4)

Conditions	Yield
In hexane; pentane addn. of Me3Al in hexane to ligand in pentane at -78°C; accordingto P. B. Hitchcock, M. F. Lappert and D.-S Liu, J. Chem. Soc., Chem. Co mmun., 1994, 1699; elem. anal.;	100%

tris(pentafluorophenyl)borate (1109-15-5) + trimethylaluminum (75-24-1) + toluene (108-88-3) → tris(pentafluorophenyl)aluminum*(toluene)0.5

Conditions	Yield
In hexane	100%
In hexane; toluene B(C6F5)3 and AlMe3 in 1:3 toluene/hexanes mixt.;	99%
In hexane; toluene (inert atm.); reaction of borane deriv. with trimethylaluminium in hexane/toluene (3:1);	99%

2,3,4,5,6-pentafluorophenol (771-61-9) + trimethylaluminum (75-24-1) → Al(OC6F5)3

Conditions	Yield
In hexane (inert atmosphere); -30°C slowly to room temp., stirring (2 h); evapn. to dryness, washing (hexane);	100%

trimethylaluminum (75-24-1) + tetraethyldistibine (4669-92-5) → [Et4Sb2][AlMe3]2

Conditions	Yield
In neat (no solvent) under N2 atm. react. Me3Al and Et4Sb2; elem. anal.;	100%

trimethylaluminum (75-24-1) + N,N',N'-Trimethyl-hexamethylcyclotristannazan (1080-40-6) → [(CH3)2AlN(Sn(CH3)3)(CH3)]2

Conditions	Yield
In toluene molar ratio 3:1;	100%

trimethylaluminum (75-24-1) + tris(diethylamino)difluorophosphorane (32318-29-9) → [FP(N(C2H5)2)3](1+)*[(CH3)3AlF](1-)=[FP(N(C2H5)2)3][(CH3)3AlF] (222190-83-2)

Conditions	Yield
In tetrahydrofuran Ar atm.; equimolar amts., stirring (20°C, 24 h); evapn. (vac.); elem. anal.;	100%

trimethylaluminum (75-24-1) + N.N'.N''-Triethyl-hexamethyl-hexahydro-symm.-triazatristannin (1778-12-7) → [(CH3)2AlN(Sn(CH3)3)(CH2CH3)]2

Conditions	Yield
In toluene molar ratio 3:1;	100%

[(CH3)2SnN(CH(CH3)2)]3 (234443-32-4) + trimethylaluminum (75-24-1) → [(CH3)2AlN(Sn(CH3)3)(CH(CH3)2)]2

Conditions	Yield
In toluene molar ratio 3:1;	100%
In toluene dry Ar atm.; 3 equiv. of AlMe3, cooling (-15°C), heating (room temp., stirring), refluxing (1,5 h, 70-80°C); concn., standing (5 to -5 degree.C, several days), washing (toluene), drying (vac.); elem. anal.;	54%

[(CH3)2SnN(CH2CH2CH3)]3 (234443-31-3) + trimethylaluminum (75-24-1) → [(CH3)2AlN(Sn(CH3)3)(CH2CH2CH3)]2

Conditions	Yield
In toluene molar ratio 3:1;	100%
In toluene dry Ar atm.; 3 equiv. of AlMe3, cooling (-15°C), heating (room temp., stirring), refluxing (1,5 h, 70-80°C); concn., standing (5 to -5 degree.C, several days), washing (toluene), drying (vac.); elem. anal.;	57%

[(CH3)2SnN(CH2CH(CH3)2)]3 (234443-33-5) + trimethylaluminum (75-24-1) → [(CH3)2AlN(Sn(CH3)3)(CH2CH(CH3)2)]2

Conditions	Yield
In toluene molar ratio 3:1;	100%
In toluene dry Ar atm.; 3 equiv. of AlMe3, cooling (-15°C), heating (room temp., stirring), refluxing (1,5 h, 70-80°C); concn., standing (5 to -5 degree.C, several days), washing (toluene), drying (vac.); elem. anal.;	58%

[(CH3)2SnNCH(CH3)(CH2CH3)]3 + trimethylaluminum (75-24-1) → [(CH3)2AlN(Sn(CH3)3)((CH3)CH(CH2CH3))]2

Conditions	Yield
In toluene molar ratio 3:1;	100%

tris(trimethylsilyl)bismuthane (81183-20-2) + trimethylaluminum (75-24-1) → (CH3)3AlBi(Si(CH3)3)3

Conditions	Yield
In neat (no solvent) substances mixted in glove box, N2; detd. by elem. anal., NMR;	100%

Upstream product

• 67-56-1 methanol 
• 74-83-9 methyl bromide 
• 75-16-1 methylmagnesium bromide 
• 593-74-8 dimethylmercury 
• 917-65-7 methylaluminum dichloride 
• 1184-58-3 dimethylaluminum chloride 
• 74-88-4 methyl iodide 
• 879678-94-1 triethylaluminum diethyl ether adduct 
• 97-93-8 triethylaluminum 
• 7429-90-5 aluminium 
• 7446-70-0 aluminium trichloride 
• 104946-37-4 (CH₃)2AlC(P(CH₃)2)3 
• 66415-27-8 2,4,6-tri-tert-butylbenzoic acid 
• 5547-35-3 [1,1':3',1''-terphenyl]-2'-carboxylic acid 

Downstream Products

• 593-90-8 trimethylborane 
• 115-09-3 methylmercury(II) chloride 
• 143-36-2 methylmercury(II) iodide 
• 506-83-2 methylmercury(II) bromide 
• 67132-74-5 3-Methylselanyl-cyclohexanone 
• 2948-55-2 3,4,5,5-Tetramethylcyclohex-2-enone 
• 67132-64-3 methyl selenoester of cyclohexanecarbocyclic acid 
• 19945-61-0 (E)-4,8-dimethylnona-1,3,7-triene 
• 56763-60-1 1-Isopropenyl-2,4-dimethyl-1-cyclohexene 
• 56870-19-0 2-(2,4-Dimethylcyclohex-1-en-1-yl)-propan-2-ol 
• 4569-45-3 9,9-dimethyl-9H-fluorene 
• 40117-45-1 2,2,6,6-Tetramethylheptan 
• 49598-54-1 2,2-Dimethyl-dodecan 
• 13092-79-0 N-ethylhexanamide 

Relevant articles and documents

27Al NMR study of the trimethylaluminum monomer-dimer equilibrium

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Process for preparing alkyl metal compounds

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