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Revision as of 12:34, 8 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank').← Previous edit		Latest revision as of 20:23, 25 November 2024 edit undoLaura240406 (talk | contribs)Extended confirmed users886 edits →History: added linkTag: Visual edit: Switched
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	{{chembox		{{Chembox
	| Verifiedfields = changed		| Verifiedfields = changed
			| Watchedfields = changed
	| verifiedrevid = 396304532		| verifiedrevid = 459990955
⚫	| ImageFileL1 = cacodylic-acid-3D-sticks.png
			| ImageFile = Cacodylic acid.svg
	| ImageSizeL1 = 120px
			| ImageSize = 160px
	| ImageFileR1 = cacodylic-acid-tetrahedral.png
			| ImageAlt = Structural formula
	| ImageSizeR1 = 175px
		⚫	| ImageFile1 = cacodylic-acid-3D-balls.png
⚫	| IUPACName = Dimethylarsinic acid
			| ImageSize1 = 160px
			| ImageAlt1 = Ball-and-stick model
			| ImageCaption1 = ]<ref>{{ Cite journal | url = https://dx.doi.org/10.5517/ccx73mv | title = CSD Entry: CADYLA01 : Dimethylarsinic acid | website = ]: Access Structures | year = 2011 | publisher = ] | doi = 10.5517/ccx73mv | access-date = 2021-12-21 | last1 = Betz | first1 = R. | last2 = McCleland | first2 = C. | last3 = Marchand | first3 = H. }}</ref><ref name="Betz">{{ cite journal | title = The monoclinic polymorph of dimethylarsinic acid | first1 = R. | last1 = Betz | first2 = C. | last2 = McCleland | first3 = H. | last3 = Marchand | journal = ] | year = 2011 | volume = 67 | issue = 8 | pages = m1013 | doi = 10.1107/S1600536811025505 | pmid = 22090811 | pmc = 3212109 }}</ref>
		⚫	| PIN = Dimethylarsinic acid
	| OtherNames = Dimethylarsenic acid, Cacodylic acid, Hydroxydimethylarsine oxide, Arsecodile, Ansar, Silvisar, Phytar 560, DMAA, UN 1572		| OtherNames = Dimethylarsenic acid, Cacodylic acid, Hydroxydimethylarsine oxide, Arsecodile, Ansar, Silvisar, Phytar 560, DMAA, UN 1572
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 2418		| ChemSpiderID = 2418
	| UNII_Ref = {{fdacite|correct|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = AJ2HL7EU8K		| UNII = AJ2HL7EU8K
	| KEGG_Ref = {{keggcite|changed|kegg}}		| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG = C07308		| KEGG = C07308
	| InChIKey = OGGXGZAMXPVRFZ-UHFFFAOYAP		| InChIKey = OGGXGZAMXPVRFZ-UHFFFAOYAP
Line 22:		Line 26:
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 75-60-5		| CASNo = 75-60-5
	| PubChem = 2513		| PubChem = 2513
	| EINECS = 200-883-4		| EINECS = 200-883-4
	| ChEBI_Ref = {{ebicite|correct|EBI}}		| ChEBI_Ref = {{ebicite|changed|EBI}}
	| ChEBI = 29839		| ChEBI = 29839
	| RTECS = CH7525000		| ChEMBL = 1231644
	| DrugBank = DB02994		| RTECS = CH7525000
			| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
			| DrugBank = DB02994
			| UNNumber = 1572
			| Gmelin = 130562
			| Beilstein = 1736965
	| SMILES = O=(O)(C)C		| SMILES = O=(O)(C)C
	| InChI = 1/C2H7AsO2/c1-3(2,4)5/h1-2H3,(H,4,5)		| InChI = 1/C2H7AsO2/c1-3(2,4)5/h1-2H3,(H,4,5)
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| Formula = C<sub>2</sub>H<sub>7</sub>AsO<sub>2</sub>		| Formula = C<sub>2</sub>H<sub>7</sub>AsO<sub>2</sub>
	| MolarMass = 137.9977 g/mol		| MolarMass = 137.9977 g/mol
	| Appearance = White crystals or powder		| Appearance = White crystals or powder
	| Density = > 1.1 g/cm<sup>3</sup>		| Odor = odorless
			| Density = > 1.1 g/cm<sup>3</sup>
	| MeltingPt = 192 - 198 °C		| MeltingPtC = 192 to 198
			| MeltingPt_notes =
	| BoilingPt = > 200 °C		| BoilingPt= >
⚫	| Solubility = 667 g/l
	| pKa = 6.3		| BoilingPtC = 200
		⚫	| Solubility = 66.7 g/100 ml
			| SolubleOther = soluble in ], ] <br /> insoluble in ]
			| pKa = 6
			| MagSus = -79.9·10<sup>−6</sup> cm<sup>3</sup>/mol
	}}		}}
	| Section3 = {{Chembox Hazards		|Section3={{Chembox Structure
			| CrystalStruct = triclinic,<ref>{{ cite journal | first1 = J. | last1 = Trotter | first2 = T. | last2 = Zobel | journal = ] | year = 1965 | pages=4466–4471 | title = 826. Stereochemistry of arsenic. Part XVI. Cacodylic acid | doi = 10.1039/JR9650004466 }}</ref> monoclinic<ref name="Betz" />
	| EUClass = {{Hazchem T+}}
			}}
⚫	| ExternalMSDS =
			|Section7={{Chembox Hazards
⚫	| FlashPt =
			| GHSPictograms = {{GHS06}}{{GHS09}}
	| Autoignition =
			| GHSSignalWord = Danger
	| RPhrases = {{R26/27/28}}, {{R40}}
			| HPhrases = {{H-phrases|301|331|410}}
			| PPhrases = {{P-phrases|261|264|270|271|273|301+310|304+340|311|321|330|391|403+233|405|501}}
			| NFPA-H = 4
			| NFPA-F = 0
			| NFPA-R = 0
		⚫	| ExternalSDS =
		⚫	| FlashPt =
			| AutoignitionPt =
			| LD50 = 23-100 mg/kg (rat and mouse, oral)
	}}		}}
	}}		}}
	'''Cacodylic acid''' is the ] with the ] (CH<sub>3</sub>)<sub>2</sub>AsO<sub>2</sub>H. Derivatives of cacodylic acid, '''cacodylates''', were frequently used as ]s. For example, "]," one of the chemicals used during the ], is a mixture of cacodylic acid and sodium cacodylate. Sodium cacodylate is frequently used as a ] in the preparation and fixation of biological samples for ].		'''Cacodylic acid''' is an ] with the ] (CH<sub>3</sub>)<sub>2</sub>]O<sub>2</sub>H. With the formula R<sub>2</sub>As(O)OH, it is the simplest of the ]. It is a colorless solid that is soluble in water.
			Neutralization of cacodylic acid with base gives '''cacodylate''' salts, e.g. '''sodium cacodylate'''. They are potent ]s. Cacodylic acid/sodium cacodylate is a ] in the preparation and fixation of biological samples for ] and in ].
	== History ==		== History ==
		⚫	In the 18th century it was found that combining ] ({{chem2|As2O3}}) and four equivalents of ] ({{chem2|CH3CO2K}}) gives a product called "]" which contains ], {{chem2|((CH3)2As)2O}} and ], {{chem2|((CH3)2As)2}}.
⚫	Significant early research into ]s was done by ] at the University of Marburg. Bunsen said of the compounds, "the smell of this body produces instantaneous tingling of the hands and feet, and even giddiness and insensibility...It is remarkable that when one is exposed to the smell of these compounds the tongue becomes covered with a black coating, even when no further evil effects are noticeable". His work in this field led to an increased understanding of the ].
			Early research into "]s" was reported by ] at the ]. Bunsen said of the compounds,
⚫	Cacodyloxide, ((CH<sub>3</sub>)<sub>2</sub>As)<sub>2</sub>O, is often considered the first ] to be prepared synthetically.
		⚫	<blockquote>"The smell of this body produces instantaneous tingling of the hands and feet, and even giddiness and insensibility... It is remarkable that when one is exposed to the smell of these compounds the tongue becomes covered with a black coating, even when no further evil effects are noticeable".</blockquote>
	== Synthesis and reactions==
⚫	In the 18th century it was known that combining As<sub>2</sub>O<sub>3</sub> and four equivalents of ] (CH<sub>3</sub>CO<sub>2</sub>K) gives a product called "]" which contains ], ((CH<sub>3</sub>)<sub>2</sub>As)<sub>2</sub>O and ], ((CH<sub>3</sub>)<sub>2</sub>As).
			His work in this field led to an increased understanding of the ].
⚫	Cacodylic acid can be reduced to dimethylarsine (III) derivatives, which are versatile intermediates for the synthesis of other organoarsenic compounds:<ref>Feltham, R. D.; Kasenally, A. and Nyholm, R. S., "A New Synthesis of Di- and Tri-Tertiary Arsines", Journal of Organometallic Chemistry, 1967, volume 7, 285-288.</ref><ref>Burrows, G. J. and Turner, E. E., "A New Type of Compound containing Arsenic", Journal of the Chemical Society Transactions, 1920, 1374-1383</ref>
	:(CH<sub>3</sub>)<sub>2</sub>AsO<sub>2</sub>H + 2 Zn + 4 HCl → (CH<sub>3</sub>)<sub>2</sub>AsH + 2 ZnCl<sub>2</sub> + 2 H<sub>2</sub>O
	:(CH<sub>3</sub>)<sub>2</sub>AsO<sub>2</sub>H + SO<sub>2</sub> + HI → (CH<sub>3</sub>)<sub>2</sub>AsI + SO<sub>3</sub> + H<sub>2</sub>O
		⚫	Cacodyl oxide, {{chem2|((CH3)2As)2O}}, is often considered the first ] to be prepared synthetically.
⚫	== Health effects ==
			Cacodylic acid and its salts were incorporated into ]s by a large variety of manufacturers under numerous brand names. APC Holdings Corp. sold cacodylic acid and its salts under the ] brand name.<ref name="Greene2005">{{cite book|author=Stanley A. Greene|title=Sittig's Handbook of Pesticides and Agricultural Chemicals|url=https://books.google.com/books?id=hAoKEHpyu6wC&pg=PA132|year=2005|publisher=William Andrew|isbn=978-0-8155-1903-4|page=132}}</ref> The variety Phytar 560G, a mixture of cacodylic acid and sodium cacodylate, was used during the ] as a ] under the name "]".<ref name="HerbicidesMedicine1994">{{cite book |author1=Committee to Review the Health Effects in Vietnam Veterans of Exposure to Herbicides |url=https://books.google.com/books?id=RjCHcoUE3B8C&pg=PA89 |title=Veterans and Agent Orange: Health Effects of Herbicides Used in Vietnam |author2=Institute of Medicine |publisher=National Academies Press |year=1994 |isbn=978-0-309-55619-4 |pages=89–90}}</ref>
	Cacodylic acid is highly toxic by ingestion, inhalation, or skin contact. Once thought to be a byproduct of inorganic arsenic detoxification, it is now believed to have serious health consequences of its own. It has been shown to be ] in rodents, most often causing cleft palate but also fetal fatality at high doses. It has been shown to be genotoxic in human cells, causing ] and also decreased DNA production and shorter DNA strands. While not itself a strong carcinogen, cacodylic acid does promote tumors in the presence of carcinogens in organs such as the kidneys and liver.
			==Reactions==
			Cacodylic acid is a ] with a pK<sub>a</sub> of around 6.25.<ref>{{cite journal |vauthors=((Shin, T.-W.)), ((Kim, K.)), ((Lee, I.-J.)) |date=April 1997 |title=Spectrophotometric determination of the acid dissociation constants for cacodylic acid and p-Nitrophenol at elevated temperatures |journal=Journal of Solution Chemistry |volume=26 |issue=4 |pages=379–390 |doi=10.1007/BF02767677 |issn=0095-9782}}</ref>
		⚫	Cacodylic acid can be reduced to dimethylarsine , which is a versatile intermediate for the synthesis of other organoarsenic compounds:<ref>{{cite journal|author1=Feltham, R. D. |author2=Kasenally, A. |author3=Nyholm, R. S. |title=A New Synthesis of Di- and Tri-Tertiary Arsines|journal=Journal of Organometallic Chemistry|year=1967|volume=7|issue=2|pages=285–288|doi=10.1016/S0022-328X(00)91079-9}}</ref><ref>Burrows, G. J. and Turner, E. E., "A New Type of Compound containing Arsenic", Journal of the Chemical Society Transactions, 1920, 1374-1383</ref>
			:{{chem2|(CH3)2AsO2H + 2 Zn + 4 HCl → (CH3)2AsH + 2 ZnCl2 + 2 H2O}}
			:{{chem2|(CH3)2AsO2H + SO2 + HI → (CH3)2AsI + SO3 + H2O}}
		⚫	== Health effects ==
			Cacodylic acid is highly toxic by ], ], or skin contact. The U.S. EPA states that all forms of arsenic are a serious risk to human health and the United States ] ranked arsenic as number 1 in its 2001 Priority List of Hazardous Substances at Superfund sites.<ref name="EPA1">{{cite web |url=https://cfpub.epa.gov/ncer_abstracts/index.cfm/fuseaction/display.highlight/abstract/6015 |title=Biogeochemistry of Arsenic in Contaminated Soils of Superfund Sites |last1=Dibyendu |first1=Sarkar |last2=Datta |first2=Rupali |date=2007 |website=EPA |publisher=United States Environmental Protection Agency |access-date=25 February 2018 |archive-url=https://web.archive.org/web/20200317143949/https://cfpub.epa.gov/ncer_abstracts/index.cfm/fuseaction/display.highlight/abstract/6015 |archive-date=17 March 2020 |url-status=dead}}</ref> Arsenic is classified as a Group-A ].<ref name="EPA1"/>
	== See also ==		== See also ==
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	* ]		* ]
	* ]		* ]
	* ]
	== References ==		== References ==
			{{reflist}}
	<references/>
⚫	* {{cite journal | author = Kenyon, E. M.; Hughes, M. F. | title = A Concise Review of the Toxicity and Carcinogenicity of Dimethylarsenic Acid | journal = ] | volume = 160 | year = 2001 | issue = 1-3 | pages = 227–236 | doi = 10.1016/S0300-483X(00)00458-3}}
			==Further reading==
		⚫	* {{cite journal |author1=Kenyon, E. M. |author2=Hughes, M. F. | title = A Concise Review of the Toxicity and Carcinogenicity of Dimethylarsenic Acid | journal = ] | volume = 160 | year = 2001 | issue = 1–3 | pages = 227–236 | doi = 10.1016/S0300-483X(00)00458-3|pmid=11246143 |url=https://zenodo.org/record/1259985 }}
	* Elschenbroich, C; Salzer, A. (1992) Organometallics, 2nd Edition		* Elschenbroich, C; Salzer, A. (1992) Organometallics, 2nd Edition
⚫	*
	== External links ==		== External links ==
	*		*
		⚫	*
	{{DEFAULTSORT:Cacodylic Acid}}		{{DEFAULTSORT:Cacodylic Acid}}
	]		]
	]		]
			]
	]
	]
	]
	]
	]
	]
	]