Browse history interactively

Page 1

Page 1Revision 1

Page 2

Page 2Revision 2

← Previous editContent deleted Content addedVisualWikitext

Revision as of 00:05, 7 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEBI_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:WikiProject_Chem← Previous edit		Latest revision as of 07:21, 17 February 2024 edit undoCitation bot (talk | contribs)Bots5,455,350 edits Altered title. | Use this bot. Report bugs. | Suggested by Abductive | Category:World War I chemical weapons | #UCB_Category 14/19
(55 intermediate revisions by 32 users not shown)
Line 1:		Line 1:
	{{chembox		{{chembox
			| Watchedfields = changed
	| Reference=<ref>''Merck Index'', 11th Edition, '''1389'''</ref>		| Reference=<ref>''Merck Index'', 11th Edition, '''1389'''</ref>
	| verifiedrevid = 443427550		| verifiedrevid = 443428893
	| ImageFile = Bromacetone Structural Formulae.png		| ImageFile = bromoaceton.svg
	| ImageSize = 220px		| ImageSize = 160
			| ImageAlt = Skeletal formula
	| IUPACName = 1-Bromoacetone		| ImageFile1 = Bromoacetone-3D-balls.png
			| ImageSize1 = 180
			| ImageAlt1 = Ball-and-stick model
			| PIN = 1-Bromopropan-2-one
	| OtherNames = Bromoacetone<br/> 1-Bromo-2-propanone<br/> α-Bromoacetone<br/> Acetonyl bromide<br/> Acetyl methyl bromide<br/> Bromomethyl methyl ketone<br/> Monobromoacetone<br/> Martonite<br/> BA<br/> UN 1569		| OtherNames = Bromoacetone<br/> 1-Bromo-2-propanone<br/> α-Bromoacetone<br/> Acetonyl bromide<br/> Acetyl methyl bromide<br/> Bromomethyl methyl ketone<br/> Monobromoacetone<br/> Martonite<br/> BA<br/> UN 1569
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
			| IUPHAR_ligand = 6293
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 11223		| ChemSpiderID = 11223
	| InChIKey = VQFAIAKCILWQPZ-UHFFFAOYAC		| InChIKey = VQFAIAKCILWQPZ-UHFFFAOYAC
Line 18:		Line 24:
	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 598-31-2		| CASNo = 598-31-2
		⚫	| UNII_Ref = {{fdacite|correct|FDA}}
⚫	| PubChem = 11715
			| UNII = 3O8L0EWR5Q
⚫	| ChEBI_Ref = {{ebicite|correct|EBI}}
		⚫	| PubChem = 11715
			| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 51845		| ChEBI = 51845
	| SMILES = BrCC(=O)C		| SMILES = BrCC(=O)C
	| InChI = 1/C3H5BrO/c1-3(5)2-4/h2H2,1H3		| InChI = 1/C3H5BrO/c1-3(5)2-4/h2H2,1H3
	| RTECS = UC0525000		| RTECS = UC0525000
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| C=3|H=5|Br=1|O=1		| C=3 | H=5 | Br=1 | O=1
	| Appearance = Colorless lachrymator		| Appearance = Colorless liquid
	| Density = 1.634 g/cm³		| Density = 1.634 g/cm<sup>3</sup>
	| MeltingPtC = -36.5		| MeltingPtC = -36.5
	| BoilingPtC = 137		| BoilingPtC = 137
	| Solubility =		| Solubility =
	| VaporPressure = 1.1 kPa (20 °C)		| VaporPressure = 1.1 kPa (20 °C)
	}}		}}
	| Section3 = {{Chembox Hazards		|Section3={{Chembox Hazards
	| ExternalMSDS =		| ExternalSDS =
	| FlashPt = 51.1 °C		| FlashPtC = 51.1
	| Autoignition =		| AutoignitionPtC =
	}}		}}
	}}		}}
	'''Bromoacetone''' is a ] with the ] {{Carbon}}{{Hydrogen}}<sub>3</sub>C{{Oxygen}}CH<sub>2</sub>{{Bromine}}. This colorless liquid is a ]. It is a precursor to other ]s.		'''Bromoacetone''' is an ] with the ] {{chem2|auto=1|CH3COCH2Br}}. It is a colorless liquid although impure samples appear yellow or even brown. It is a ] and a precursor to other ]s.
		⚫	==Occurrence in nature==
	Bromoacetone was first prepared in the 19th century.<ref>Sokolowsky, Berichte volume 9, pp. 1687 (1876).</ref> It was used in ] as a ], called '''BA''' by British and '''B-Stoff''' (white cross) by Germans. Due to its toxicity, it is obsolete as a ] and is not used anymore.
			Bromoacetone is present (less than 1%) in the ] of a ] ('']'') from the vicinity of the ].<ref>{{cite journal |author1=Burreson, B. J. |author2=Moore, R. E. |author3=Roller, P. P. | title = Volatile halogen compounds in the alga ''Asparagopsis taxiformis'' (Rhodophyta) | journal = Journal of Agricultural and Food Chemistry | year = 1976 | volume = 24 | issue = 4 | pages = 856–861 | doi = 10.1021/jf60206a040}}</ref>
⚫	==Occurrence==
	Bromoacetone is naturally present (less than 1%) in the ] of a ] from the vicinity of the ].<ref>{{cite journal
	| title = Volatile halogen compounds in the alga ''Asparagopsis taxiformis'' (Rhodophyta)
	| author = B. Jay Burreson, Richard E. Moore, and Peter P. Roller
	| journal = Journal of Agricultural and Food Chemistry
	| pages = 856–861
	| doi = 10.1021/jf60206a040
	| volume = 24
	| issue = 4
	| year = 1976}}</ref> In atmosphere it is degraded by the photochemically produced ] ].
	==Synthesis==		==Synthesis==
			Bromoacetone is available commercially, sometimes stabilized with ]. It was first described in the 19th century, attributed to N. Sokolowsky.<ref>{{cite journal | author = Wagner, G. | title = Sitzung der russischen chemischen Gesellschaft am 7./19. October 1876 | journal = Berichte der Deutschen Chemischen Gesellschaft | year = 1876 | volume = 9 | issue = 2 | pages = 1687–1688 | doi = 10.1002/cber.187600902196 | url = http://gallica.bnf.fr/ark:/12148/bpt6k906830/f657.image.langEN| url-access = subscription }}</ref>
	Bromoacetone is available commercially, sometimes stabilized with ].
			]
	Bromoacetone is prepared by reacting ] and ],<ref>{{OrgSynth | author = [[Phoebus Levene|
	Levene, P. A.]] | title = Bromoacetone | collvol = 2 | collvolpages = 88 | year = 1943 | prep = cv2p0088}}</ref> with catalytic acid. If you use a base you will obtain bromoform instead.
	H<sub>3</sub>
	C(O)CH<sub>3</sub> + Br<sub>2</sub> → CH<sub>3</sub>C(O)CH<sub>2</sub>Br + HBr
	As with all ketones, acetone ]izes in the presence of acids or bases. The alpha carbon then undergoes ] with bromine.<ref>{{cite web | title = Carbonyl Reactivity | work = VirtualText of Organic Chemistry | author = William Reusch | url = http://www.cem.msu.edu/~reusch/VirtualText/aldket2.htm | accessdate = 2007-10-27}}</ref> The main difficulty with this method is over-bromination, resulting in di- and tribrominated products.		Bromoacetone is prepared by combining ] and ],<ref>{{OrgSynth | author = Levene, P. A. | title = Bromoacetone | year = 1930 | volume = 10 | pages = 12 | collvol = 2 | collvolpages = 88 | prep = cv2p0088}}</ref> with catalytic acid. As with all ketones, acetone ]izes in the presence of acids or bases. The alpha carbon then undergoes ] with bromine. The main difficulty with this method is over-bromination, resulting in di- and tribrominated products. If a base is present, ] is obtained instead, by the ].<ref>{{cite web | title = Carbonyl Reactivity | work = Virtual Textbook of Organic Chemistry | author = Reusch, W. | url = http://www.cem.msu.edu/~reusch/VirtualText/aldket2.htm | date = 2013-05-05 | publisher = Michigan State University | access-date = 2007-10-27 | archive-url = https://web.archive.org/web/20100621055908/http://www.cem.msu.edu/~reusch/VirtualText/aldket2.htm | archive-date = 2010-06-21 | url-status = dead}}</ref>
	==Applications==		==Applications==
	Bromoacetone is a versatile ] in ]. It is, for example, the precursor to ] (b.p. 35–47°/12 mm, CAS #116-09-6).<ref>{{OrgSynth | author = Levene, P. A.; Walti, A. | title = Acetol | collvol = 2 | collvolpages = 5 | year = 1943 | prep = cv2p0005}}</ref>		It was used in ] as a ], called '''BA''' by British and '''B-Stoff''' ('']'') by Germans. Due to its toxicity, it is not used as a riot control agent anymore. Bromoacetone is a versatile reagent in ]. It is, for example, the precursor to ] by reaction with aqueous sodium hydroxide.<ref>{{OrgSynth | author = Levene, P. A. |author2=Walti, A. | title = Acetol | year = 1930 | volume = 10 | pages = 1 | collvol = 2 | collvolpages = 5 | prep = cv2p0005 }}</ref>
	==See also==		==See also==
	*]		*]
			*]
			*]
			*]
			*]
	==References==		==References==
	<references/>		<references/>
			{{Chemical agents}}
	]		]
Line 79:		Line 80:
	]		]
	]		]
	]
	]
	]
	]
	]