Product Name

  • Name

    TRIMETHYLINDIUM

  • EINECS 222-200-9
  • CAS No. 3385-78-2
  • Article Data37
  • CAS DataBase
  • Density 1.568 g/cmg/cm3
  • Solubility
  • Melting Point 88 °C
  • Formula C3H9In
  • Boiling Point 135.7°C
  • Molecular Weight 159.924
  • Flash Point -18°C
  • Transport Information
  • Appearance COA
  • Safety 7-16-43-45
  • Risk Codes 14-17-34
  • Molecular Structure Molecular Structure of 3385-78-2 (TRIMETHYLINDIUM)
  • Hazard Symbols
  • Synonyms Trimethylindium;
  • PSA 0.00000
  • LogP 1.75140

Synthetic route

indium
7440-74-6

indium

methyl aluminium sesquichloride

methyl aluminium sesquichloride

trimethyl indium
3385-78-2

trimethyl indium

Conditions
ConditionsYield
With methylene chloride; sodium at 30 - 40℃; under 375.038 Torr; Flow reactor; Inert atmosphere;93%
indium(III) chloride
10025-82-8

indium(III) chloride

magnesium
7439-95-4

magnesium

methyl iodide
74-88-4

methyl iodide

trimethyl indium
3385-78-2

trimethyl indium

Conditions
ConditionsYield
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

(CH2)3(P(C6H5)2In(CH3)3)2*C6H6

trimethyl indium
3385-78-2

trimethyl indium

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

(triphenylphosphine)trimethylindium

trimethyl indium
3385-78-2

trimethyl indium

Conditions
ConditionsYield
In neat (no solvent) metal complex decomposed at 110-135°C for 2-3 h;75%
Triethylindium
923-34-2

Triethylindium

methyl iodide
74-88-4

methyl iodide

trimethyl indium
3385-78-2

trimethyl indium

Conditions
ConditionsYield
at 70℃;66%
methylmagnesium chloride
676-58-4

methylmagnesium chloride

trimethyl indium
3385-78-2

trimethyl indium

Conditions
ConditionsYield
With indium(III) chloride
With indium(III) chloride In tetrahydrofuran at -78℃; Cooling with dry ice bath;
dimethylmercury
593-74-8

dimethylmercury

indium

indium

trimethyl indium
3385-78-2

trimethyl indium

Conditions
ConditionsYield
With mercury dichloride at 100℃;
tetrakis(trimethylindium) 1,4,8,11-tetramethyl-1,4,8,11-tetraazacyclotetradecane adduct
331815-63-5

tetrakis(trimethylindium) 1,4,8,11-tetramethyl-1,4,8,11-tetraazacyclotetradecane adduct

trimethyl indium
3385-78-2

trimethyl indium

Conditions
ConditionsYield
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

trimethylindium bis(N,N,N',N'-tetramethyl-4,4'-methylenebis(aniline)) adduct

trimethyl indium
3385-78-2

trimethyl indium

Conditions
ConditionsYield
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

hexakis(trimethylindium) 1,4,7,10,13,16-hexamethyl-1,4,7,10,13,16-hexaazacyclooctadecane adduct

trimethyl indium
3385-78-2

trimethyl indium

Conditions
ConditionsYield
In neat (no solvent) at 80-115°C under vac.;
indium
7440-74-6

indium

Hg dimethyl

Hg dimethyl

trimethyl indium
3385-78-2

trimethyl indium

Conditions
ConditionsYield
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

methyllithium

indium(III) chloride
10025-82-8

indium(III) chloride

trimethyl indium
3385-78-2

trimethyl indium

Conditions
ConditionsYield
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]

[((CH3)2InBi(Si(CH3)3)2)3]

A

bismuth
7440-69-9

bismuth

B

indium
7440-74-6

indium

C

tetrakis(trimethylsilyl)dibismutane
81174-93-8

tetrakis(trimethylsilyl)dibismutane

D

trimethyl indium
3385-78-2

trimethyl indium

Conditions
ConditionsYield
In not given decompn. at temp. above -30 °C within minutes;
Cp*2U[(μ-Me)(InMe3)]2

Cp*2U[(μ-Me)(InMe3)]2

A

dimethylbis(η5-pentamethylcyclopentadienyl)uranium
67605-92-9

dimethylbis(η5-pentamethylcyclopentadienyl)uranium

B

trimethyl indium
3385-78-2

trimethyl indium

Conditions
ConditionsYield
In neat (no solvent) drying under vac.;
indium
7440-74-6

indium

trimethylaluminum
75-24-1

trimethylaluminum

methyl iodide
74-88-4

methyl iodide

trimethyl indium
3385-78-2

trimethyl indium

Conditions
ConditionsYield
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

indium(III) chloride

methyllithium
917-54-4

methyllithium

trimethyl indium
3385-78-2

trimethyl indium

Conditions
ConditionsYield
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

indium(III) chloride

methylaluminium sesquichloride

methylaluminium sesquichloride

A

trimethyl indium
3385-78-2

trimethyl indium

B

dimethylindium chloride
14629-99-3

dimethylindium chloride

Conditions
ConditionsYield
With potassium chloride; sodium chloride at 150 - 250℃; Inert atmosphere;
trimethylaluminum
75-24-1

trimethylaluminum

indium(III) acetate

indium(III) acetate

trimethyl indium
3385-78-2

trimethyl indium

Conditions
ConditionsYield
With Durasyn 162 for 3.5h; Temperature;92 %Spectr.
indium tris(2-ethylhexanoate)

indium tris(2-ethylhexanoate)

trimethylaluminum
75-24-1

trimethylaluminum

trimethyl indium
3385-78-2

trimethyl indium

Conditions
ConditionsYield
In 2-Methylpentane at 20 - 38℃;100 %Spectr.
indium(III) chloride

indium(III) chloride

methyl metal compound

methyl metal compound

trimethyl indium
3385-78-2

trimethyl indium

Conditions
ConditionsYield
In tetrahydrofuran; hexane at -78℃;
1H-imidazole
288-32-4

1H-imidazole

trimethyl indium
3385-78-2

trimethyl indium

(CH3)2InN2C3H3
138748-24-0

(CH3)2InN2C3H3

Conditions
ConditionsYield
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

trimethyl indium

N,N',N'-Trimethyl-hexamethylcyclotristannazan
1080-40-6

N,N',N'-Trimethyl-hexamethylcyclotristannazan

[(CH3)2InN(Sn(CH3)3)(CH3)]2

[(CH3)2InN(Sn(CH3)3)(CH3)]2

Conditions
ConditionsYield
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

trimethyl indium

N.N'.N''-Triethyl-hexamethyl-hexahydro-symm.-triazatristannin
1778-12-7

N.N'.N''-Triethyl-hexamethyl-hexahydro-symm.-triazatristannin

[(CH3)2InN(Sn(CH3)3)(CH2CH3)]2

[(CH3)2InN(Sn(CH3)3)(CH2CH3)]2

Conditions
ConditionsYield
In toluene molar ratio 3:1;100%
[(CH3)2SnN(CH(CH3)2)]3
234443-32-4

[(CH3)2SnN(CH(CH3)2)]3

trimethyl indium
3385-78-2

trimethyl indium

[(CH3)2InN(Sn(CH3)3)(CH(CH3)2)]2

[(CH3)2InN(Sn(CH3)3)(CH(CH3)2)]2

Conditions
ConditionsYield
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

[(CH3)2SnN(CH2CH2CH3)]3

trimethyl indium
3385-78-2

trimethyl indium

[(CH3)2InN(Sn(CH3)3)(CH2CH2CH3)]2

[(CH3)2InN(Sn(CH3)3)(CH2CH2CH3)]2

Conditions
ConditionsYield
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

[(CH3)2SnN(CH2CH(CH3)2)]3

trimethyl indium
3385-78-2

trimethyl indium

[(CH3)2InN(Sn(CH3)3)(CH2CH(CH3)2)]2

[(CH3)2InN(Sn(CH3)3)(CH2CH(CH3)2)]2

Conditions
ConditionsYield
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

[(CH3)2SnNCH(CH3)(CH2CH3)]3

trimethyl indium
3385-78-2

trimethyl indium

[(CH3)2InN(Sn(CH3)3)((CH3)CH(CH2CH3))]2

[(CH3)2InN(Sn(CH3)3)((CH3)CH(CH2CH3))]2

Conditions
ConditionsYield
In toluene molar ratio 3:1;100%
Triethylsilanol
597-52-4

Triethylsilanol

trimethyl indium
3385-78-2

trimethyl indium

[{Me2In(μ-triethylsilanolate)}2]
1441368-53-1

[{Me2In(μ-triethylsilanolate)}2]

Conditions
ConditionsYield
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

tris(tert-butoxy)silanol

trimethyl indium
3385-78-2

trimethyl indium

[{Me2In(μ-tris(tert-butoxy)silanolate)}2]

[{Me2In(μ-tris(tert-butoxy)silanolate)}2]

Conditions
ConditionsYield
In diethyl ether at 20℃; for 12h; Inert atmosphere; Schlenk technique;100%
C17H31F3O4SSi

C17H31F3O4SSi

trimethyl indium
3385-78-2

trimethyl indium

C17H34OSi

C17H34OSi

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran99%
trimethyl indium
3385-78-2

trimethyl indium

(4-dimethylaminopyridine)trimethylindium(III)

(4-dimethylaminopyridine)trimethylindium(III)

Conditions
ConditionsYield
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

trimethyl indium

N-cyclohexyl-cyclohexanamine
101-83-7

N-cyclohexyl-cyclohexanamine

trimethyl(dicyclohexylamine)indium(III)

trimethyl(dicyclohexylamine)indium(III)

Conditions
ConditionsYield
In pentane (N2); filtn., stirring; solvent removal (vac.);99%
trimethyl indium
3385-78-2

trimethyl indium

dibenzylamine
103-49-1

dibenzylamine

In(CH3)3(HN(CH2C6H5)2)

In(CH3)3(HN(CH2C6H5)2)

Conditions
ConditionsYield
In pentane (N2); filtn., stirring; solvent removal (vac.);99%
trimethyl indium
3385-78-2

trimethyl indium

dibutylamine
111-92-2

dibutylamine

In(CH3)3(HN(CH2CH2CH2CH3)2)

In(CH3)3(HN(CH2CH2CH2CH3)2)

Conditions
ConditionsYield
In pentane (N2); filtn., stirring; solvent removal (vac.);99%
trimethyl indium
3385-78-2

trimethyl indium

diethylamine
109-89-7

diethylamine

In(CH3)3(HN(CH2CH3)2)

In(CH3)3(HN(CH2CH3)2)

Conditions
ConditionsYield
In pentane (N2); filtn., stirring; solvent removal (vac.);99%
hexamethylene imine
111-49-9

hexamethylene imine

trimethyl indium
3385-78-2

trimethyl indium

In(CH3)3(HNC6H12)

In(CH3)3(HNC6H12)

Conditions
ConditionsYield
In pentane (N2); filtn., stirring; solvent removal (vac.);99%
1-methyl-piperazine
109-01-3

1-methyl-piperazine

trimethyl indium
3385-78-2

trimethyl indium

In(CH3)3(HN(CH2CH2)2NCH3)

In(CH3)3(HN(CH2CH2)2NCH3)

Conditions
ConditionsYield
In pentane (N2); filtn., stirring; solvent removal (vac.);99%
diisobutylamine
21981-37-3

diisobutylamine

trimethyl indium
3385-78-2

trimethyl indium

In(CH3)3(HN((CH3)3C)2)

In(CH3)3(HN((CH3)3C)2)

Conditions
ConditionsYield
In pentane (N2); filtn., stirring; solvent removal (vac.);99%
Di-sec-butylamin
626-23-3

Di-sec-butylamin

trimethyl indium
3385-78-2

trimethyl indium

In(CH3)3(HN(CH3CHCH2CH3)2)

In(CH3)3(HN(CH3CHCH2CH3)2)

Conditions
ConditionsYield
In pentane (N2); filtn., stirring; solvent removal (vac.);99%
pyrrolidine
123-75-1

pyrrolidine

trimethyl indium
3385-78-2

trimethyl indium

In(CH3)3(HNC4H8)

In(CH3)3(HNC4H8)

Conditions
ConditionsYield
In pentane (N2); filtn., stirring; solvent removal (vac.);99%
piperidine
110-89-4

piperidine

trimethyl indium
3385-78-2

trimethyl indium

In(CH3)3(HNC5H10)

In(CH3)3(HNC5H10)

Conditions
ConditionsYield
In pentane (N2); filtn., stirring; solvent removal (vac.);99%
trimethyl indium
3385-78-2

trimethyl indium

di-n-propylamine
142-84-7

di-n-propylamine

In(CH3)3(HN(CH2CH2CH3)2)

In(CH3)3(HN(CH2CH2CH3)2)

Conditions
ConditionsYield
In pentane (N2); filtn., stirring; solvent removal (vac.);99%
trimethyl indium
3385-78-2

trimethyl indium

diisopropylamine
108-18-9

diisopropylamine

In(CH3)3(HN(CH3CHCH3)2)

In(CH3)3(HN(CH3CHCH3)2)

Conditions
ConditionsYield
In pentane (N2); filtn., stirring; solvent removal (vac.);99%
trimethyl indium
3385-78-2

trimethyl indium

methyl salicylate
119-36-8

methyl salicylate

[(CH3)2In(C8H7O3)]2
200724-27-2

[(CH3)2In(C8H7O3)]2

Conditions
ConditionsYield
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

trimethyl indium

dimethyl amine
124-40-3

dimethyl amine

In(CH3)3(HN(CH3)2)

In(CH3)3(HN(CH3)2)

Conditions
ConditionsYield
In pentane (N2); filtn., stirring; solvent removal (vac.);99%
trimethyl indium
3385-78-2

trimethyl indium

1,3-bis(mesityl)imidazolium chloride
141556-45-8

1,3-bis(mesityl)imidazolium chloride

(IMes)InMe2Cl

(IMes)InMe2Cl

Conditions
ConditionsYield
In dichloromethane byproducts: CH4; elem. anal.;99%
(1R,2S)-1-Amino-2-indanol
136030-00-7

(1R,2S)-1-Amino-2-indanol

trimethyl indium
3385-78-2

trimethyl indium

(1R,2S)-(+)-cis-dimethylindium-1-amino-2-indanolate

(1R,2S)-(+)-cis-dimethylindium-1-amino-2-indanolate

Conditions
ConditionsYield
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

trimethyl indium

(1S,2R)-(-)-cis-dimethylindium-1-amino-2-indanolate

(1S,2R)-(-)-cis-dimethylindium-1-amino-2-indanolate

Conditions
ConditionsYield
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

trimethyl indium

acetylacetone
123-54-6

acetylacetone

tris(2,4-pentanedionato)indium(III)

tris(2,4-pentanedionato)indium(III)

Conditions
ConditionsYield
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

(S)-2-dimethylamino-3-phenyl-1-propanol

trimethyl indium
3385-78-2

trimethyl indium

[(μ-(S)-Me2NCH(CH2Ph)CH2O)InMe2]2

[(μ-(S)-Me2NCH(CH2Ph)CH2O)InMe2]2

Conditions
ConditionsYield
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%

Trimethyl indium Specification

The Trimethyl indium with CAS registry number of 3385-78-2 is also called Indium,trimethyl-. Its EINECS registry number is 222-200-9. The IUPAC name is trimethylindigane. In addition, the molecular formula is C3H9In and the molecular weight is 159.92.

Physical properties about this chemical are: (1)Exact Mass: 159.974303; (2)MonoIsotopic Mass: 159.974303; (3)Heavy Atom Count: 4; (4)Complexity: 8; (5)Covalently-Bonded Unit Count: 1;.

Preparation of Trimethyl indium: it can be prepared by In, Mg and CH3I. You can go through the operation of solution collaterals and fractionation to get high purity Trimethyl indium.

Uses of Trimethyl indium: it can react with 1-trifluoromethansulfonyloxy-4-t-butylcyclohexene to get 1-methyl-4-tert-butyl-1-cyclohexene. This reaction will need reagent Pd(PPh3)2Cl2 and solvent tetrahydrofuran. The reaction time is 7 hours by heating. The yield is about 92%.

Trimethyl indium can react with 1-trifluoromethansulfonyloxy-4-t-butylcyclohexene to get 1-methyl-4-tert-butyl-1-cyclohexene

When you are using this chemical, please be cautious about it as the following:
It is spontaneously flammable in air and can react violently with water. And it can cause burns. In case of fire, use ... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add - Never use water). And in case of accident or if you feel unwell, seek medical advice immediately (show label where possible). You should keep container tightly closed and keep away from sources of ignition - No smoking.

You can still convert the following datas into molecular structure:
(1)SMILES: [In](C)(C)C
(2)InChI: InChI=1/3CH3.In/h3*1H3;/rC3H9In/c1-4(2)3/h1-3H3
(3)InChIKey: IBEFSUTVZWZJEL-SGQDGSKVAB

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