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Revision as of 15:31, 8 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:Wi← Previous edit		Latest revision as of 22:58, 14 July 2024 edit undoAnDeargMor (talk | contribs)Extended confirmed users798 edits Given fire diamond, makes sense to add toxic to intoTag: Visual edit
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	{{chembox		{{chembox
			| Verifiedfields = changed
⚫	| verifiedrevid = 443692698
			| Watchedfields = changed
⚫	| ImageFile = Dimethylzinc-3D-balls.png
		⚫	| verifiedrevid = 443694271
⚫	| ImageSize = 200px
		⚫	| ImageFile = Dimethylzinc-3D-balls.png
⚫	| ImageName = Ball-and-stick model of dimethylzinc
		⚫	| ImageSize =
⚫	| IUPACName = dimethylzinc
		⚫	| ImageName = Ball-and-stick model of dimethylzinc
	| OtherNames =
			| ImageCaption = White: ], Black: ], Grey: ]
⚫	| Section1 = {{Chembox Identifiers
		⚫	| IUPACName = Dimethylzinc
⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| OtherNames = {{ubl|2-Zincapropane|Dimethyl zinc|Dimethylzincane|DMZ|DMZn|Methylzinc|Zinc carbanide|Zinc methanide|Zinc methyl|Zinc trihydrogenmethanide}}
		⚫	| Section1 = {{Chembox Identifiers
		⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 10254473		| ChemSpiderID = 10254473
	| InChI = 1/2CH3.Zn/h2*1H3;/rC2H6Zn/c1-3-2/h1-2H3		| InChI = 1/2CH3.Zn/h2*1H3;/rC2H6Zn/c1-3-2/h1-2H3
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	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 544-97-8		| CASNo = 544-97-8
		⚫	| UNII_Ref = {{fdacite|correct|FDA}}
⚫	| PubChem =
			| UNII = 8H6R0N8W2F
⚫	| ChEBI_Ref = {{ebicite|correct|EBI}}
		⚫	| PubChem = 11010
			| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 51497		| ChEBI = 51497
	| SMILES = CC		| SMILES = CC
	}}		}}
	| Section2 = {{Chembox Properties		| Section2 = {{Chembox Properties
	| Formula = Zn(CH<sub>3</sub>)<sub>2</sub>		| Formula = {{chem2|Zn(CH3)2}}
	| MolarMass = 95.478 g/mol		| MolarMass = 95.478 g/mol
	| Appearance =		| Appearance = Colorless liquid
			| Odor = Garlic<ref name="pubchem">{{cite web | url=https://pubchem.ncbi.nlm.nih.gov/compound/Dimethylzinc | title=Dimethylzinc }}</ref>
	| Density =
			| Density = 1.386 g/cm<sup>3</sup> at 10.5 °C<ref name="pubchem" />
	| MeltingPt =
	| BoilingPt =		| MeltingPtC = -42
	| Solubility =		| BoilingPtC = 46
			| Solubility =
			| SolubleOther = Soluble in ], ], ]; decomposes in water, ] and ]<ref name="pubchem" />
			| VaporPressure = 50.13 kPa<ref name="pubchem" />
			| ThermalConductivity = 0.1627 W/(m∙K) at {{cvt|70|C|F}}<ref name="pubchem" />
			| Viscosity = 0.807 mPa·s at {{cvt|70|F|C}}<ref name="pubchem" />
	}}		}}
	| Section3 = {{Chembox Hazards		| Section4 = {{Chembox Thermochemistry
			| HeatCapacity = 129.20 J/(mol∙K) (liquid at {{cvt|25|C|F}})<ref name="chemeo">{{cite web | url=https://www.chemeo.com/cid/15-221-9/dimethylzinc | title=Dimethylzinc (CAS 544-97-8) }}</ref>
	| MainHazards =
	| FlashPt =		| DeltaHvap =
	| Autoignition =
	}}		}}
			| Section7 = {{Chembox Hazards
			| MainHazards = Spontaneously ignites in air and violently reacts with water, evolving irritant and toxic fumes.<ref name="pubchem" />
			| FlashPt =
			| AutoignitionPt = {{cvt|0|F|C}}<ref name="pubchem" />
			| NFPA-H = 3
			| NFPA-F = 4
			| NFPA-R = 3
			| NFPA-S = W
			| GHSPictograms = {{GHS02}}{{GHS05}}{{GHS09}}
			| GHSSignalWord = Danger
			| HPhrases = {{H-phrases|H225|H250|H260|H314|H410}}
			| PPhrases = {{P-phrases|P210|P222|P223|P231+P232|P233|P235|P240|P241|P242|P243|P260|P264|P273|P280|P301+P330+P331|P302|P303+P361+P353|P304+P340|P305|P316|P317|P321|P334|P335|P338|P361|P363|P370+P378|P391|P402+P404|P403|P405|P501}}
	}}		}}
			| Section8 = {{Chembox Related
⚫	'''Dimethylzinc''', also known as Zinc methyl, DMZ, or DMZn is a colorless mobile ] Zn(CH<sub>3</sub>)<sub>2</sub>, formed by the action of ] on ] at elevated temperature or on zinc sodium alloy. <!-- Hota, N.K., Willis, C.J. doi:10.1016/S0022-328X(00)92419-7 An improved preparation of dialkylzinc compounds J. Organometal. Chem. 9 1 (1967) 169-170
			| OtherCompounds = {{ubl|]|]}}
			}}
			}}
			'''Dimethylzinc''', also known as zinc methyl, DMZ, or DMZn, is a toxic ] with the ] {{chem2|Zn(CH3)2|auto=1}}. It belongs to the large series of similar ] such as ].
			==Preparation==
		⚫	It is formed by the action of ] on ] or zinc-] ] at elevated temperatures. <!-- Hota, N.K., Willis, C.J. {{doi|10.1016/S0022-328X(00)92419-7}} An improved preparation of dialkylzinc compounds J. Organometal. Chem. 9 1 (1967) 169-170
	72 Foster, D.F.; Cole-Hamilton, D.J. Inorg. Synth. 31 (1997) 29-66-->		72 Foster, D.F.; Cole-Hamilton, D.J. Inorg. Synth. 31 (1997) 29-66-->
			:{{chem2|2 Zn + 2 CH3I → Zn(CH3)2 + ZnI2}}
	:2Zn + 2CH<sub>3</sub>I → Zn(CH<sub>3</sub>)<sub>2</sub> + ZnI<sub>2</sub>
	The sodium assists the reaction of the zinc with the methyl iodide. Zinc iodide is formed as a byproduct.		Sodium assists the reaction of the zinc with the methyl iodide. ] is formed as a byproduct.
			==Properties==
	It has a disagreeable ], and is spontaneously ] in air. It has been of great importance in the ] of ]. It is soluble in alkanes and often sold as a solution in hexanes.
	It belongs to the large series of similar ] such as ].
			Dimethylzinc is a colorless mobile ] ], which has a characteristic disagreeable garlic-like ]. It is a very reactive and strong ].<ref name="pubchem" /> It is soluble in ] and often sold as a solution in ]. The ] of dimethylzinc is {{cvt|230.13|K|C}} ± 0.02 K.<ref name="chemeo" /> The ] molecule of dimethylzinc is ] at Zn center and ] at C centers.
			==Toxicity and hazards==
			Inhalation of dimethylzinc mist or vapor causes immediate irritation of the upper respiratory tract, and may cause ] and death. Eyes are immediately and severely irritated and burned by liquid, vapor, or dilute solutions. If not removed by thorough flushing with water, this chemical may permanently damage the ], eventually causing blindness. If dimethylzinc contacts the skin, it causes thermal and acid burns by reacting with moisture on skin. Unless washed quickly, skin may be scarred. Ingestion, while unlikely, also causes immediate burns. Nausea, vomiting, cramps, and diarrhea may follow, and tissues may ]ate if not promptly treated. Upon heating, dimethylzinc vapor decomposes to irritating and toxic products.<ref name="pubchem" />
			Contact of dimethylzinc with ] may form explosive ]. Dimethylzinc oxidises in ] very slowly, producing ] {{chem2|CH3ZnOCH3}}.
			Dimethylzinc is very ] and can spontaneously ] in air. It burns in air with a blue flame, giving off a garlic-like odor. The products of decomposition (fire smoke) include ], which itself is not toxic, but its fumes can irritate lungs and cause ], severe injury, or death.
			Dimethylzinc fire must be extinguished with dry sand. The fire reacts violently or explosively with water, generating very flammable ] gas which can explode in air upon catching fire, and lung-irritating smoke of ]. Dimethylzinc fire reacts violently or explosively with ], ] and ]. It explodes in ] and ]. Improperly handled containers of dimethylzinc can explode, causing serious injuries or death.<ref name="pubchem" />
			==Structure==
			In the ] the compound exists in two modifications. The ] high-temperature phase shows a two-dimensional disorder, while the low-temperature phase which is ] is ordered. The molecules are linear with Zn-C bond lengths measuring 192.7(6) pm.<ref>{{cite journal |author1=John Bacsa |author2=Felix Hanke |author3=Sarah Hindley |author4=Rajesh Odedra |author5=George R. Darling |author6=Anthony C. Jones |author7=Alexander Steiner | title = The Solid State Structures of Dimethylzinc and Diethylzinc | journal = ] | year = 2011 | volume = 50 |issue=49 | pages = 11685–11687 | doi = 10.1002/anie.201105099|pmid=21919175 |pmc=3326375 }}</ref> The structure of the ] shows a very similar Zn-C distance of 193.0(2) pm.<ref>{{cite journal |author1=A. Haaland |author2=J. C. Green |author3=G. S. McGrady |author4=A. J. Downs |author5=E. Gullo |author6=M. J. Lyall |author7=J. Timberlake |author8=A. V. Tutukin |author9=H. V. Volden |author10=K.-A. Østby | title = The length, strength and polarity of metal–carbon bonds: dialkylzinc compounds studied by density functional theory calculations, gas electron diffraction and photoelectron spectroscopy | journal = ] |issue=22 | year = 2003 | pages = 4356–4366 | doi = 10.1039/B306840B}}</ref>
	==History==		==History==
	This substance was first prepared by ] during his work with ] in 1849 at the ]. After heating a mixture of zinc and ] in an airtight vessel a flame bursted out after the seal was broken.<ref>{{cite journal		Dimethylzinc was first prepared by ] during his work with ] in 1849 at the ]. After heating a mixture of zinc and ] in an airtight vessel, a flame burst out when the seal was broken.<ref>{{cite journal
	| author = ]		| author = E. Frankland
			| author-link = Edward Frankland
	| journal = ]		| journal = ]
	| title = Notiz über eine neue Reihe organischer Körper, welche Metalle, Phosphor u. s. w. enthalten		| title = Notiz über eine neue Reihe organischer Körper, welche Metalle, Phosphor u. s. w. enthalten
	| year = 1849		| year = 1849
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	| issue = 2		| issue = 2
	| pages = 213–216		| pages = 213–216
	| doi = 10.1002/jlac.18490710206}}</ref> In laboratory scale the synthesis method did not change till today, except that ] or copper compounds are used to activate the zinc.		| doi = 10.1002/jlac.18490710206| url = https://zenodo.org/record/1427026
			}}</ref> In the laboratory, this synthesis method remains unchanged today, except that ] or copper compounds are used to activate the zinc.
			==Uses==
	Dimethyl zinc was used for a long time to introduce methyl groups into organic molecules or to synthesize organometalic compounds containing methyl groups. ], (organo-magnesium compounds), which are easier to handle and less flammable replaced organo-zinc compounds in most laboratory syntheses. Due to differences in reactivity (as well as in reaction by-products) between organo-zinc compounds and Grignard reagents, organo-zinc compounds may be preferred in some syntheses.		Dimethylzinc has been of great importance in the ] of ]. It was used for a long time to introduce methyl groups into organic molecules or to synthesize organometallic compounds containing methyl groups. ], (organo-magnesium compounds), which are easier to handle and less flammable, replaced organo-zinc compounds in most laboratory syntheses. Due to differences in reactivity (as well as in reaction byproducts) between organo-zinc compounds and Grignard reagents, organo-zinc compounds may be preferred in some syntheses.<ref>{{cite book|last=Erdik|first=Ender|title=Organozinc reagents in organic synthesis|year=1996|publisher=CRC Press|location=Boca Raton|isbn=978-0-8493-9151-4}}</ref>
			Its high vapor pressure has led to extensive uses in the production of ], e.g. metalorganic chemical vapor deposition (]) for the preparation of wide ] ] semiconducting films (e.g. ], ], ], ], ]) and as p-] precursors for ] semiconductors (e.g. ], ], ], ], ]), which have many ] and ] applications.<ref>{{cite journal |author1=Mohammad Afzaal |author2=Mohammad A. Malik |author3=Paul O’Brien | title = Preparation of zinc containing materials | journal = ] | year = 2007 | volume = 31 |issue=12 | pages = 2029–2040 | doi = 10.1039/b712235g}}</ref>
			It is used as an accelerator in ], as a ], and as a ] in ].
	==References==		==References==
	{{Reflist}}		{{Reflist}}
			{{Zinc compounds}}
			{{Authority control}}
	{{Organic-compound-stub}}
	]		]
	]		]
			]
			]
	]
			]
	]
	]