3385-78-2

Basic information

• Product Name: TRIMETHYLINDIUM
• Synonyms: TRIMETHYLINDIUM;Indium, trimethyl-;Trimethylindiumelecgrwhitextl;Trimethylindium,98+%(99.9+%-In);Trimethylindium,elec.gr.(99.999%-In)PURATREM;TRIMETHYLINDIUM (99.9%IN);TRIMETHYL INDIUM, TYPE C BUBBLER, BOTTOM DIA. 50.8MM DIA.;Trimethlindium
• CAS NO: 3385-78-2
• Molecular Formula: C₃H₉In
• Molecular Weight: 159.92
• EINECS: 222-200-9
• Product Categories: metal alkyl
• Mol File: 3385-78-2.mol
• Article Data: 27

Chemical Properties

• Melting Point: 88°C
• Boiling Point: 135.7°C
• Flash Point: -18°C
• Appearance: white/crystal
• Density: 1,568 g/cm3
• Sensitive: heat sensitive, moisture sensiti
• CAS DataBase Reference: TRIMETHYLINDIUM(CAS DataBase Reference)
• NIST Chemistry Reference: TRIMETHYLINDIUM(3385-78-2)
• EPA Substance Registry System: TRIMETHYLINDIUM(3385-78-2)

Safety Data

• Statements: 14-17-34
• Safety Statements: 7-16-43-45
• RIDADR: 2845
• TSCA: Yes
• HazardClass: 4.2
• PackingGroup: I
• Hazardous Substances Data: 3385-78-2(Hazardous Substances Data)

Usage

Properties

WARNING Trimethylindium may undergo rapid thermal decomposition if exposed to temperatures above 100°C. Never attempt to distill the material at atmospheric pressure.

InChI:InChI=1/3CH3.In/h3*1H3;/rC3H9In/c1-4(2)3/h1-3H3

Synthetic route

indium (7440-74-6) + methyl aluminium sesquichloride → trimethyl indium (3385-78-2)

Conditions	Yield
With methylene chloride; sodium at 30 - 40℃; under 375.038 Torr; Flow reactor; Inert atmosphere;	93%

indium(III) chloride (10025-82-8) + magnesium (7439-95-4) + methyl iodide (74-88-4) → trimethyl indium (3385-78-2)

Conditions	Yield
In diethyl ether a Grignard soln. (prepd. from MeI and Mg in Et2O) is added to the suspn. of InCl3 in ether and refluxed for 3 h; distn. of excess of Et2O at atm. pressure affords Me3In*Et2O; repeated distn. of the etherate at room temp. in vac. affords InMe3;	92%

(CH2)3(P(C6H5)2In(CH3)3)2*C6H6 → trimethyl indium (3385-78-2)

Conditions	Yield
In neat (no solvent) metal complex decomposed at 110-135°C for 2-3 h;	81%

(triphenylphosphine)trimethylindium → trimethyl indium (3385-78-2)

Conditions	Yield
In neat (no solvent) metal complex decomposed at 110-135°C for 2-3 h;	75%

Triethylindium (923-34-2) + methyl iodide (74-88-4) → trimethyl indium (3385-78-2)

Conditions	Yield
at 70℃;	66%

methylmagnesium chloride (676-58-4) → trimethyl indium (3385-78-2)

Conditions	Yield
With indium(III) chloride
With indium(III) chloride In tetrahydrofuran at -78℃; Cooling with dry ice bath;

dimethylmercury (593-74-8) + indium → trimethyl indium (3385-78-2)

Conditions	Yield
With mercury dichloride at 100℃;

tetrakis(trimethylindium) 1,4,8,11-tetramethyl-1,4,8,11-tetraazacyclotetradecane adduct (331815-63-5) → trimethyl indium (3385-78-2)

Conditions	Yield
In neat (no solvent) at 80-115°C under vac.;

trimethylindium bis(N,N,N',N'-tetramethyl-4,4'-methylenebis(aniline)) adduct (329955-33-1) → trimethyl indium (3385-78-2)

Conditions	Yield
In neat (no solvent) at 80-115°C under vac.;

hexakis(trimethylindium) 1,4,7,10,13,16-hexamethyl-1,4,7,10,13,16-hexaazacyclooctadecane adduct (331815-64-6) → trimethyl indium (3385-78-2)

Conditions	Yield
In neat (no solvent) at 80-115°C under vac.;

indium (7440-74-6) + Hg dimethyl → trimethyl indium (3385-78-2)

Conditions	Yield
With mercury dichloride heating for 8 days at 100°C in CO2 atmosphere; cooled by ice then Hg(CH3)2 removed by distillation;
With HgCl2 heating for 8 days at 100°C in CO2 atmosphere; cooled by ice then Hg(CH3)2 removed by distillation;

methyllithium (917-54-4) + indium(III) chloride (10025-82-8) → trimethyl indium (3385-78-2)

Conditions	Yield
In diethyl ether InCl3 heated at 80°C in vac. for 1 h, purged Ar, ether added, cooled (ice bath), MeLi added; stirred for 2 h, evapd.;
In diethyl ether (inert atmosphere); addn. of MeLi in Et2O to InCl3 in Et2O at 0°C, warming to room temp.; filtration; prepd. as soln.;
In not given under Ar; MeLi (3 equiv.) in THF or hexane or Et2O added slowly (15-30 min) to cooled (-78°C) soln. of InCl3 in THF; stirred for 30 min; warmed to room temp.; according to H. C. Clark, A. L. Pickard, J. Organomet. Chem. 8 (1967) 427;

[((CH3)2InBi(Si(CH3)3)2)3] → bismuth (7440-69-9) + indium (7440-74-6) + tetrakis(trimethylsilyl)dibismutane (81174-93-8) + trimethyl indium (3385-78-2)

Conditions	Yield
In not given decompn. at temp. above -30 °C within minutes;

Cp*2U[(μ-Me)(InMe3)]2 → dimethylbis(η5-pentamethylcyclopentadienyl)uranium (67605-92-9) + trimethyl indium (3385-78-2)

Conditions	Yield
In neat (no solvent) drying under vac.;

indium (7440-74-6) + trimethylaluminum (75-24-1) + methyl iodide (74-88-4) → trimethyl indium (3385-78-2)

Conditions	Yield
Stage #1: indium; methyl iodide In 2,6,10,15,19,23-hexamethyltetracosane at 110℃; for 2h; Stage #2: trimethylaluminum With tri-n-propylamine In 2,6,10,15,19,23-hexamethyltetracosane at 90℃; for 1h; Product distribution / selectivity;

indium(III) chloride + methyllithium (917-54-4) → trimethyl indium (3385-78-2)

Conditions	Yield
In tetrahydrofuran at -78℃; for 0.5h;
In tetrahydrofuran at -78℃; for 0.5h;
In tetrahydrofuran; diethyl ether at 0 - 20℃; for 0.25h; Inert atmosphere;

indium(III) chloride + methylaluminium sesquichloride → trimethyl indium (3385-78-2) + dimethylindium chloride (14629-99-3)

Conditions	Yield
With potassium chloride; sodium chloride at 150 - 250℃; Inert atmosphere;

trimethylaluminum (75-24-1) + indium(III) acetate → trimethyl indium (3385-78-2)

Conditions	Yield
With Durasyn 162 for 3.5h; Temperature;	92 %Spectr.

indium tris(2-ethylhexanoate) + trimethylaluminum (75-24-1) → trimethyl indium (3385-78-2)

Conditions	Yield
In 2-Methylpentane at 20 - 38℃;	100 %Spectr.

indium(III) chloride + methyl metal compound → trimethyl indium (3385-78-2)

Conditions	Yield
In tetrahydrofuran; hexane at -78℃;

1H-imidazole (288-32-4) + trimethyl indium (3385-78-2) → (CH3)2InN2C3H3 (138748-24-0)

Conditions	Yield
In toluene under Ar or N2, stirred, refluxed for 2-3 h; removal of solvent, filtered off, washed with benzene or hexane, dried under vac.; elem. anal.;	100%

trimethyl indium (3385-78-2) + N,N',N'-Trimethyl-hexamethylcyclotristannazan (1080-40-6) → [(CH3)2InN(Sn(CH3)3)(CH3)]2

Conditions	Yield
In toluene molar ratio 3:1;	100%
In benzene 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.;	70%

trimethyl indium (3385-78-2) + N.N'.N''-Triethyl-hexamethyl-hexahydro-symm.-triazatristannin (1778-12-7) → [(CH3)2InN(Sn(CH3)3)(CH2CH3)]2

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

[(CH3)2SnN(CH(CH3)2)]3 (234443-32-4) + trimethyl indium (3385-78-2) → [(CH3)2InN(Sn(CH3)3)(CH(CH3)2)]2

Conditions	Yield
In toluene molar ratio 3:1;	100%
In benzene 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.;	84%

[(CH3)2SnN(CH2CH2CH3)]3 (234443-31-3) + trimethyl indium (3385-78-2) → [(CH3)2InN(Sn(CH3)3)(CH2CH2CH3)]2

Conditions	Yield
In toluene molar ratio 3:1;	100%
In benzene 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.;	79%

[(CH3)2SnN(CH2CH(CH3)2)]3 (234443-33-5) + trimethyl indium (3385-78-2) → [(CH3)2InN(Sn(CH3)3)(CH2CH(CH3)2)]2

Conditions	Yield
In toluene molar ratio 3:1;	100%
In benzene 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.;	88%

[(CH3)2SnNCH(CH3)(CH2CH3)]3 + trimethyl indium (3385-78-2) → [(CH3)2InN(Sn(CH3)3)((CH3)CH(CH2CH3))]2

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

Triethylsilanol (597-52-4) + trimethyl indium (3385-78-2) → [{Me2In(μ-triethylsilanolate)}2] (1441368-53-1)

Conditions	Yield
In diethyl ether at 20℃; for 12h; Inert atmosphere; Schlenk technique;	100%
In benzene Inert atmosphere; Schlenk technique;

tris(tert-butoxy)silanol (18166-43-3) + trimethyl indium (3385-78-2) → [{Me2In(μ-tris(tert-butoxy)silanolate)}2]

Conditions	Yield
In diethyl ether at 20℃; for 12h; Inert atmosphere; Schlenk technique;	100%

C17H31F3O4SSi + trimethyl indium (3385-78-2) → C17H34OSi

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran	99%

dmap (1122-58-3) + trimethyl indium (3385-78-2) → (4-dimethylaminopyridine)trimethylindium(III)

Conditions	Yield
In hexane; toluene under Ar, 1 equiv. of metal-compd. was added to 9:1 hexane:toluene soln.of amine; crystn. at -30 °C; elem. anal.;	99%
In diethyl ether; Petroleum ether soln. of equimolar amts. of aminopyridine and Me3In in diethyl ether/light petroleum (1:2) cooled to -30°C; crystals collected, washed with light petroleum, and dried in vac.; elem. anal.;	91%

trimethyl indium (3385-78-2) + N-cyclohexyl-cyclohexanamine (101-83-7) → trimethyl(dicyclohexylamine)indium(III)

Conditions	Yield
In pentane (N2); filtn., stirring; solvent removal (vac.);	99%

trimethyl indium (3385-78-2) + dibenzylamine (103-49-1) → In(CH3)3(HN(CH2C6H5)2)

Conditions	Yield
In pentane (N2); filtn., stirring; solvent removal (vac.);	99%

trimethyl indium (3385-78-2) + dibutylamine (111-92-2) → In(CH3)3(HN(CH2CH2CH2CH3)2)

Conditions	Yield
In pentane (N2); filtn., stirring; solvent removal (vac.);	99%

trimethyl indium (3385-78-2) + diethylamine (109-89-7) → In(CH3)3(HN(CH2CH3)2)

Conditions	Yield
In pentane (N2); filtn., stirring; solvent removal (vac.);	99%

hexamethylene imine (111-49-9) + trimethyl indium (3385-78-2) → In(CH3)3(HNC6H12)

Conditions	Yield
In pentane (N2); filtn., stirring; solvent removal (vac.);	99%

1-methyl-piperazine (109-01-3) + trimethyl indium (3385-78-2) → In(CH3)3(HN(CH2CH2)2NCH3)

Conditions	Yield
In pentane (N2); filtn., stirring; solvent removal (vac.);	99%

diisobutylamine (21981-37-3) + trimethyl indium (3385-78-2) → In(CH3)3(HN((CH3)3C)2)

Conditions	Yield
In pentane (N2); filtn., stirring; solvent removal (vac.);	99%

Di-sec-butylamin (626-23-3) + trimethyl indium (3385-78-2) → In(CH3)3(HN(CH3CHCH2CH3)2)

Conditions	Yield
In pentane (N2); filtn., stirring; solvent removal (vac.);	99%

pyrrolidine (123-75-1) + trimethyl indium (3385-78-2) → In(CH3)3(HNC4H8)

Conditions	Yield
In pentane (N2); filtn., stirring; solvent removal (vac.);	99%

piperidine (110-89-4) + trimethyl indium (3385-78-2) → In(CH3)3(HNC5H10)

Conditions	Yield
In pentane (N2); filtn., stirring; solvent removal (vac.);	99%

trimethyl indium (3385-78-2) + di-n-propylamine (142-84-7) → In(CH3)3(HN(CH2CH2CH3)2)

Conditions	Yield
In pentane (N2); filtn., stirring; solvent removal (vac.);	99%

trimethyl indium (3385-78-2) + diisopropylamine (108-18-9) → In(CH3)3(HN(CH3CHCH3)2)

Conditions	Yield
In pentane (N2); filtn., stirring; solvent removal (vac.);	99%

trimethyl indium (3385-78-2) + methyl salicylate (119-36-8) → [(CH3)2In(C8H7O3)]2 (200724-27-2)

Conditions	Yield
In toluene (N2); dropwise addn. of InMe3 to methyl salicylate in toluene at -78°C, warming to room temp.; solvent removal (vac.), crystn. (toluene/hexane); elem. anal.;	99%

trimethyl indium (3385-78-2) + dimethyl amine (124-40-3) → In(CH3)3(HN(CH3)2)

Conditions	Yield
In pentane (N2); filtn., stirring; solvent removal (vac.);	99%

trimethyl indium (3385-78-2) + 1,3-bis(mesityl)imidazolium chloride (141556-45-8) → (IMes)InMe2Cl

Conditions	Yield
In dichloromethane byproducts: CH4; elem. anal.;	99%

(1R,2S)-1-Amino-2-indanol (136030-00-7) + trimethyl indium (3385-78-2) → (1R,2S)-(+)-cis-dimethylindium-1-amino-2-indanolate

Conditions	Yield
In toluene byproducts: CH4; all manipulations under dry oxygen-free N2 atm.; soln. of org. compd. added dropwise to soln. of metal compd. at room temp., stirred for 12 h; solvent removed in vac., crystd. from toluene; elem. anal.;	99%

trimethyl indium (3385-78-2) + (1S,2R)-1-amino-2-indanol (7480-35-5, 13286-59-4, 74165-73-4, 126456-43-7, 136030-00-7, 140632-19-5, 140632-20-8) → (1S,2R)-(-)-cis-dimethylindium-1-amino-2-indanolate

Conditions	Yield
In toluene byproducts: CH4; all manipulations under dry oxygen-free N2 atm.; soln. of org. compd. added dropwise to soln. of metal compd. at room temp., stirred for 12 h; solvent removed in vac., crystd. from toluene; elem. anal.;	99%

trimethyl indium (3385-78-2) + acetylacetone (123-54-6) → tris(2,4-pentanedionato)indium(III)

Conditions	Yield
In neat (no solvent) byproducts: CH4; (Ar); addn. of ligand to indium compd. at -196°C, slow warming toroom temp., keeping at 20°C for 28 d; evapn.;	98.3%

(S)-2-dimethylamino-3-phenyl-1-propanol (27720-03-2) + trimethyl indium (3385-78-2) → [(μ-(S)-Me2NCH(CH2Ph)CH2O)InMe2]2

Conditions	Yield
In toluene byproducts: CH4; under N2, 1 equiv. of alc. in toluene was added to a stirred toluene soln. of Me3In at room temp., stirring for 0.5 h; solvent was removed in vac., crystn. from n-pentane at 6 °C, elem. anal.;	98%

Upstream product

• 676-58-4 methylmagnesium chloride 
• 593-74-8 dimethylmercury 
• 10025-82-8 indium(III) chloride 
• 7439-95-4 magnesium 
• 74-88-4 methyl iodide 
• 331815-63-5 tetrakis(trimethylindium) 1,4,8,11-tetramethyl-1,4,8,11-tetraazacyclotetradecane adduct 
• 329955-33-1 trimethylindium bis(N,N,N',N'-tetramethyl-4,4'-methylenebis(aniline)) adduct 
• 331815-64-6 hexakis(trimethylindium) 1,4,7,10,13,16-hexamethyl-1,4,7,10,13,16-hexaazacyclooctadecane adduct 
• 7440-74-6 indium 
• 917-54-4 methyllithium 
• 75-24-1 trimethylaluminum 
• 923-34-2 Triethylindium 

Downstream Products

• 92274-82-3 dimethyl-indium⁽¹⁺⁾; dimethylamide 
• 1005-64-7 trans-1-phenyl-1-butene 
• 934-10-1 3-phenylbut-1-ene 
• 22433-39-2 1-methyl-1-phenylallene 
• 52741-30-7 (1-methyl-1,2-butadienyl)benzene 
• 22398-80-7 indium(III) phosphide 
• 12030-05-6 indium(III) nitride 
• 7440-74-6 indium 
• 12030-05-6 indium nitride 
• 77590-14-8 trans-[dimethylindium methylphenylamide dimer] 
• 22398-80-7 indium phosphide 
• 303031-29-0 [((CH3)2In)2(OC4H3CHNNC6H5)]2(μ4-O) 

Relevant articles and documents

The spectroscopy of InSe nanoparticles

The synthesis of several different sizes of InSe nanoparticles from organometallic precursors is reported. These particles are characterized by transmission electron microscopy, electron diffraction, and optical spectroscopy. The electron diffraction results and optical properties indicate that these particles are two-dimensional disks, consisting of single Se-In-In-Se tetralayer sheets. The absorption spectra indicate strong quantum confinement along the z axis and, for the smaller particles, in the x,y plane. The z-axis quantum confinement may be quantitatively understood in terms of the band structure of bulk InSe. The results indicate that the z-axis quantum confinement reverses the order of the direct and indirect transitions in the case of the largest particles. The smaller particles exhibit strong, polarized fluorescence, and the fluorescence polarization may also be understood in terms of the band structure of bulk InSe. ? 2005 American Chemical Society.

Process for preparing alkyl metal compounds

The invention relates to a method for producing alkyl metal compounds, starting materials for the production of trialkyl gallium and trialkyl indium comprise metallic indium or metallic gallium, at least one alkyl donor, a reducing agent and a solvent; the alkyl donor is alkyl halide; R in MR 2-4 represents alkyl group, 2 to 4 R groups are independently selected from the same or different alkyl groups; M is especially aluminum, gallium or indium; high purity gallium or indium or aluminum is used; sesquialkyl aluminum chloride is used as a reaction promoter, and the metal gallium or metal indium is reacted with alkyl chloride of the alkyl donor at low temperature and low pressure to generate sesquialkyl gallium chloride or sesquialkyl indium chloride; when the sesquialkyl gallium chloride or indium sesquialkyl chloride is reduced to the trialkyl gallium or trialkyl indium by a reducing agent, metal gallium or metal indium is necessarily generated simultaneously; the newly generated metal gallium or metal indium reacts with chloromethane (ethyl) in situ, so that the starting materials are fully utilized. The yield of the two steps is almost complete. The new synthetic route is an environment-friendly green process.

Aryl-NHC-group 13 trimethyl complexes: structural, stability and bonding insights

Treatment of aromatic N-substituted N-heterocyclic carbenes (NHCs) with trimethyl-gallium and -indium yielded the new Lewis acid-base adducts, IMes·GaMe3 (1), SIMes·GaMe3 (2), IPr·GaMe3 (3), SIPr·GaMe3 (4), IMes·InMe3 (5), SIMes·InMe3 (6), IPr·InMe3 (7), and SIPr·InMe3 (8), with all complexes being identified by X-ray diffraction, IR, and multinuclear NMR analyses. Complex stability was found to be largely dependent on the nature of the constituent NHC ligands. Percent buried volume (%VBur) and topographic steric map analyses were employed to quantify and elucidate the observed trends. Additionally, a detailed bond snapping energy (BSE) decomposition analysis focusing on both steric and orbital interactions of the M-NHC bond (M = Al, Ga and In) has been performed.