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{{chembox {{chembox
| Watchedfields = changed
| verifiedrevid = 417228927 | verifiedrevid = 434968600
| ImageFile = Trimethylgallium-2D.png | ImageFile = Trimethylgallium-2D.png
| ImageName = Structural formula of trimethylgallium | ImageName = Structural formula of trimethylgallium
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| IUPACName = trimethylgallane, trimethanidogallium | IUPACName = trimethylgallane, trimethanidogallium
| OtherNames = | OtherNames =
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 14323 | ChemSpiderID = 14323
| InChI = 1/3CH3.Ga/h3*1H3;/rC3H9Ga/c1-4(2)3/h1-3H3 | InChI = 1/3CH3.Ga/h3*1H3;/rC3H9Ga/c1-4(2)3/h1-3H3
Line 18: Line 19:
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 1445-79-0 | CASNo = 1445-79-0
| PubChem = 15051 | PubChem = 15051
| SMILES = (C)(C)C | SMILES = (C)(C)C
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = Ga(CH<sub>3</sub>)<sub>3</sub> | Formula = Ga(CH<sub>3</sub>)<sub>3</sub>
| MolarMass = 114.827 g/mol | MolarMass = 114.827 g/mol
| Appearance = clear colourless liquid | Appearance = colourless liquid
| Density = | Density =
| MeltingPtC = -15
| MeltingPt = <nowiki>&minus;</nowiki>15 °C
| BoilingPt = 55.7 °C | BoilingPtC = 55.7
| Solubility = | Solubility = Reacts with water
⚫ }}
⚫ | Section3 = {{Chembox Hazards
| MainHazards = pyrophoric
⚫ | FlashPt =
| Autoignition =
}} }}
⚫ |Section3={{Chembox Hazards
| MainHazards = Pyrophoric (can ignite spontaneously in air), reacts with water to release methane
⚫ | FlashPt =
| AutoignitionPt =
⚫ }}
}} }}


'''Trimethylgallium''', often abbreviated to '''TMG''' or '''TMGa''', is the organogallium compound with the formula Ga(CH<sub>3</sub>)<sub>3</sub>. It is a colorless, ] liquid.<ref name=IS>{{cite book |doi=10.1002/9780470132623.ch8|title=Inorganic Syntheses|year=1997|last1=Bradley|first1=D. C.|last2=Chudzynska|first2=H. C.|last3=Harding|first3=I. S.|chapter=Trimethylindium and Trimethylgallium |pages=67–74|volume=31|isbn=978-0-470-13262-3}}</ref> Unlike ], TMG adopts a ] structure.<ref>{{Greenwood&Earnshaw2nd}}</ref> When examined in detail, the monomeric units are clearly linked by multiple weak Ga---C interactions, reminiscent of the situation for ].<ref>{{cite journal |doi=10.1002/1521-3773(20020715)41:14<2519::AID-ANIE2519>3.0.CO;2-2|title=Luminescence Phenomena and Solid-State Structures of Trimethyl- and Triethylgallium |year=2002 |last1=Mitzel |first1=Norbert W. |last2=Lustig |first2=Christian |last3=Berger |first3=Raphael J. F. |last4=Runeberg |first4=Nino |journal=Angewandte Chemie International Edition |volume=41 |issue=14 |pages=2519–2522 |pmid=12203520 }}</ref>
⚫ '''Trimethylgallium''', Ga(CH<sub>3</sub>)<sub>3</sub>, often abbreviated to '''TMG''' or '''TMGa''', is the preferred ] source of ] for ] (MOVPE) of gallium-containing ]s, such as ], ], ], ], ], ], ], ] and AlInGaNP.

==Properties==
TMG is a clear, colorless, ] liquid.<ref>{{cite journal | last1 = Shenaikhatkhate | first1 = D | last2 = Goyette | first2 = R | last3 = Dicarlojr | first3 = R | last4 = Dripps | first4 = G | title = Environment, health and safety issues for sources used in MOVPE growth of compound semiconductors | journal = Journal of Crystal Growth | volume = 272 | pages = 816 | year = 2004 | doi = 10.1016/j.jcrysgro.2004.09.007 | bibcode=2004JCrGr.272..816S}}</ref> Even the hydrocarbon solutions of TMG, when sufficiently saturated, are known to catch fire on exposure to air. TMG is known to react violently with water and other compounds that are capable of providing labile and active ] (i.e. ]s). Therefore, TMG needs to be handled with care and caution, e.g. stored in a cool, dry place at 0-25 °C, under ] atmosphere, and ensuring that storage temperatures would not exceed 40 °C to avoid deterioration.


==Preparation== ==Preparation==
Trimethylgallium may be prepared by the reaction of ] with ]. The less volatile diethyl ether adduct can be prepared by using ] in ether in place of dimethylzinc; the ether ligands may be displaced with liquid ammonia as well.<ref>{{cite journal | doi = 10.1073/pnas.19.3.292 | pmc = 1085965 | volume = 19 | issue = 3 | title = Trimethyl gallium, Trimethyl gallium etherate and Trimethyl gallium ammine | pages = 292–298 | year = 1933 | author = C. A. Kraus; F. E. Toonder | journal = ] | pmid=16577510}}</ref> Two forms of TMG are typically investigated: ] adducts or TMG itself. All are prepared by reactions of ] with various methylating agents. When the methylation is conducted with ] in ], the product is the poorly volatile diethyl ether adduct. As noted by TMG discoverers Kraus and Toonder in 1933, the ether ligand is not readily lost, although it may be displaced with liquid ammonia.<ref>{{ cite journal |author1=Kraus, C. A. |author2=Toonder, F. E. | title = Trimethyl Gallium, Trimethyl Gallium Etherate and Trimethyl Gallium Ammine | journal = ] | year = 1933 | volume = 19 | issue = 3 | pages = 292–8 | doi = 10.1073/pnas.19.3.292 | pmc = 1085965 | pmid = 16577510 | bibcode = 1933PNAS...19..292K |doi-access=free }}</ref> When the alkylation is conducted with ] in the presence of a tertiary phosphine the air-stable phosphine adduct is obtained:
:{{chem2| GaCl3 + 3 MeLi + PR3 -> R3P\sGaMe3 + 3 LiCl}}
Heating the solid phosphine adduct under vacuum liberates the base-free TMG:<ref name=IS/>
:{{chem2| R3P\sGaMe3 -> R3P + GaMe3}}
Other non-volatile bases have been described.<ref>{{cite book | last1= Foster | first1=Douglas F. | last2= Cole-Hamilton|first2=David J. | title=Inorganic Syntheses | chapter=Electronic Grade Alkyls of Group 12 and 13 Elements|page =29-66|volume=31|year=1997|doi=10.1002/9780470132623.ch7| isbn=978-0-471-15288-0 }}</ref>
Other methylating agents for the synthesis of TMG include ] and ].



==Applications== ==Applications==
⚫ TMG is the preferred ] source of ] for ] (MOVPE) of gallium-containing ]s, such as ], ], ], ], ], ], ], ], AlInGaNP and ].<ref>{{cite journal | last1 = Shenai-Khatkhate | first1 = D. V. | last2 = Goyette | first2 = R. J. | last3 = Dicarlo | first3 = R. L. Jr | last4 = Dripps | first4 = G. | title = Environment, health and safety issues for sources used in MOVPE growth of compound semiconductors | journal = Journal of Crystal Growth | year = 2004 | volume = 272 | issue = 1–4 | pages = 816–21 | doi = 10.1016/j.jcrysgro.2004.09.007 | bibcode = 2004JCrGr.272..816S }}</ref>
The material is used in the production of LED lighting and semiconductors as a metalorganic chemical vapor deposition precursor. These material are used in the production of LED lighting and semiconductors as a metalorganic chemical vapor deposition precursor.


==References== ==References==
<references/> <references/>
{{gallium compounds}}


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Latest revision as of 09:06, 2 May 2024

Trimethylgallium
Structural formula of trimethylgallium
Structural formula of trimethylgallium
Ball-and-stick model of trimethylgallium
Ball-and-stick model of trimethylgallium
Names
IUPAC name trimethylgallane, trimethanidogallium
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.014.452 Edit this at Wikidata
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/3CH3.Ga/h3*1H3;Key: XCZXGTMEAKBVPV-UHFFFAOYSA-N
  • InChI=1/3CH3.Ga/h3*1H3;/rC3H9Ga/c1-4(2)3/h1-3H3Key: XCZXGTMEAKBVPV-YHXBHQJBAF
SMILES
  • (C)(C)C
Properties
Chemical formula Ga(CH3)3
Molar mass 114.827 g/mol
Appearance colourless liquid
Melting point −15 °C (5 °F; 258 K)
Boiling point 55.7 °C (132.3 °F; 328.8 K)
Solubility in water Reacts with water
Hazards
Occupational safety and health (OHS/OSH):
Main hazards Pyrophoric (can ignite spontaneously in air), reacts with water to release methane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Trimethylgallium, often abbreviated to TMG or TMGa, is the organogallium compound with the formula Ga(CH3)3. It is a colorless, pyrophoric liquid. Unlike trimethylaluminium, TMG adopts a monomeric structure. When examined in detail, the monomeric units are clearly linked by multiple weak Ga---C interactions, reminiscent of the situation for trimethylindium.

Preparation

Two forms of TMG are typically investigated: Lewis base adducts or TMG itself. All are prepared by reactions of gallium trichloride with various methylating agents. When the methylation is conducted with methylmagnesium iodide in diethyl ether, the product is the poorly volatile diethyl ether adduct. As noted by TMG discoverers Kraus and Toonder in 1933, the ether ligand is not readily lost, although it may be displaced with liquid ammonia. When the alkylation is conducted with methyl lithium in the presence of a tertiary phosphine the air-stable phosphine adduct is obtained:

GaCl3 + 3 MeLi + PR3 → R3P−GaMe3 + 3 LiCl

Heating the solid phosphine adduct under vacuum liberates the base-free TMG:

R3P−GaMe3 → R3P + GaMe3

Other non-volatile bases have been described. Other methylating agents for the synthesis of TMG include dimethylzinc and trimethylaluminium.


Applications

TMG is the preferred metalorganic source of gallium for metalorganic vapour phase epitaxy (MOVPE) of gallium-containing compound semiconductors, such as GaAs, GaN, GaP, GaSb, InGaAs, InGaN, AlGaInP, InGaP, AlInGaNP and Ga2O3. These material are used in the production of LED lighting and semiconductors as a metalorganic chemical vapor deposition precursor.

References

  1. ^ Bradley, D. C.; Chudzynska, H. C.; Harding, I. S. (1997). "Trimethylindium and Trimethylgallium". Inorganic Syntheses. Vol. 31. pp. 67–74. doi:10.1002/9780470132623.ch8. ISBN 978-0-470-13262-3.
  2. Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. ISBN 978-0-08-037941-8.
  3. Mitzel, Norbert W.; Lustig, Christian; Berger, Raphael J. F.; Runeberg, Nino (2002). "Luminescence Phenomena and Solid-State Structures of Trimethyl- and Triethylgallium". Angewandte Chemie International Edition. 41 (14): 2519–2522. doi:10.1002/1521-3773(20020715)41:14<2519::AID-ANIE2519>3.0.CO;2-2. PMID 12203520.
  4. Kraus, C. A.; Toonder, F. E. (1933). "Trimethyl Gallium, Trimethyl Gallium Etherate and Trimethyl Gallium Ammine". PNAS. 19 (3): 292–8. Bibcode:1933PNAS...19..292K. doi:10.1073/pnas.19.3.292. PMC 1085965. PMID 16577510.
  5. Foster, Douglas F.; Cole-Hamilton, David J. (1997). "Electronic Grade Alkyls of Group 12 and 13 Elements". Inorganic Syntheses. Vol. 31. p. 29-66. doi:10.1002/9780470132623.ch7. ISBN 978-0-471-15288-0.
  6. Shenai-Khatkhate, D. V.; Goyette, R. J.; Dicarlo, R. L. Jr; Dripps, G. (2004). "Environment, health and safety issues for sources used in MOVPE growth of compound semiconductors". Journal of Crystal Growth. 272 (1–4): 816–21. Bibcode:2004JCrGr.272..816S. doi:10.1016/j.jcrysgro.2004.09.007.
Gallium compounds
Gallium(−V)
Gallium(I)
Gallium(II)
Gallium(I,III)
Gallium(III)
Organogallium(III) compounds
  • Ga(C5H7O2)3
  • Ga(CH3)3
  • Ga(C2H5)3
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