| Revision as of 20:17, 5 April 2011 editLuckas-bot (talk | contribs)929,662 editsm r2.7.1) (robot Adding: pl:Bromooctan etylu← Previous edit |
Latest revision as of 21:30, 15 April 2024 edit undoBernardirfan (talk | contribs)Extended confirmed users10,991 edits Wrong categorization (Bromoacetic acid is not an ester) |
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| verifiedrevid = 415312463 |
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| Watchedfields = changed |
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| Name = Ethyl bromoacetate |
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| verifiedrevid = 422573093 |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| Name = Ethyl bromoacetate |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFile = Ethyl-bromoacetate-2D-skeletal.png |
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| ImageFile = Ethyl-bromoacetate-2D-skeletal.png |
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| ImageName = Skeletal formula of ethyl bromoacetate |
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<!-- | ImageSize = 200px --> |
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| ImageName = Skeletal formula of ethyl bromoacetate |
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| ImageFile1 = Ethyl-bromoacetate-3D-balls.png |
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| ImageName1 = Ball-and-stick model of ethyl bromoacetate |
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| ImageFile1 = Ethyl-bromoacetate-3D-balls.png |
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| PIN = Ethyl bromoacetate<!-- the locant ‘2’ for acetic acid is not cited, see P-14.3.4.3 of Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) --> |
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<!-- | ImageSize1 = 200px --> |
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| OtherNames = {{ubl|Antol|Bromoacetic acid, ethyl ester|Ethoxycarbonylmethyl bromide|Ethyl 2-bromoacetate}} |
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| ImageName1 = Ball-and-stick model of ethyl bromoacetate |
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|Section1={{Chembox Identifiers |
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| IUPACName = Ethyl bromoacetate |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| OtherNames = Bromoacetic acid<br />ethyl ester, Antol,<br />(Ethoxycarbonyl)-<br />methyl bromide |
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| CASNo = 105-36-2 |
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| Section1 = {{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| SMILES = BrCC(=O)OCC |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 7462 |
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| ChemSpiderID = 7462 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 1085948 |
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| EC_number = 203-290-9 |
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| PubChem = 7748 |
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| PubChem = 7748 |
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| RTECS = AF6000000 |
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| UNNumber = 1603 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = D20KFB313W |
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| InChI = 1/C4H7BrO2/c1-2-7-4(6)3-5/h2-3H2,1H3 |
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| InChI = 1/C4H7BrO2/c1-2-7-4(6)3-5/h2-3H2,1H3 |
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| InChIKey = PQJJJMRNHATNKG-UHFFFAOYAE |
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| InChIKey = PQJJJMRNHATNKG-UHFFFAOYAE |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 1085948 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C4H7BrO2/c1-2-7-4(6)3-5/h2-3H2,1H3 |
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| StdInChI = 1S/C4H7BrO2/c1-2-7-4(6)3-5/h2-3H2,1H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = PQJJJMRNHATNKG-UHFFFAOYSA-N |
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| StdInChIKey = PQJJJMRNHATNKG-UHFFFAOYSA-N |
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| SMILES = BrCC(=O)OCC |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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}} |
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| CASNo = 105-36-2 |
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|Section2={{Chembox Properties |
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| RTECS = AF6000000 |
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| Formula = {{chem2|BrCH2CO2CH2CH3}} |
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| C=4 | H=7 | Br=1 | O=2 |
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| Section2 = {{Chembox Properties |
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| Appearance = Colorless to yellow liquid<ref name=chemicalland21> (dead link 13 September 2018) </ref> |
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| Formula = C<sub>4</sub>H<sub>7</sub>O<sub>2</sub>Br |
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| MolarMass = 167.01 g/mol |
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| Density = 1.51 g/cm<sup>3</sup> |
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| Solubility = Insoluble |
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| Appearance = colourless to yellow liquid |
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| MeltingPtC = −38 |
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| Density = 1.51 g/cm<sup>3</sup>, liquid |
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| MeltingPt_ref = <ref name=chemicalland21/> |
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| Solubility = Insoluble |
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| BoilingPtC = 158 |
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| MeltingPt = -38 °C (199 K) |
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| BoilingPt_ref = <ref name=chemicalland21/> |
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| BoilingPt = 158 °C (431 K) |
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| Odor = Fruity, pungent<ref name=Criswell /> |
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| Viscosity = |
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| MagSus = −82.8·10<sup>−6</sup> cm<sup>3</sup>/mol |
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| Section3 = {{Chembox Structure |
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| Dipole = |
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| Dipole = |
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| Section7 = {{Chembox Hazards |
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| ExternalMSDS = |
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|Section7={{Chembox Hazards |
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| EUClass = Very toxic ('''T+'''), Powerful lachrymator, Extremely harmful, |
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| NFPA-H = 3 |
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| ExternalSDS = |
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| NFPA-F = 0 |
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| NFPA-H = 4 |
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| NFPA-R = 4 |
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| NFPA-F = 0 |
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| NFPA-R = 3 |
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| RPhrases = {{R26/27/28}} |
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| GHSPictograms = {{GHS06}} |
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| SPhrases = {{S1/2}}, {{S7/9}}, {{S26}}, {{S45}} |
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| FlashPt = 47 °C |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|300|310|330}} |
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| PPhrases = {{P-phrases|260|262|264|270|271|280|284|301+310|302+350|304+340|310|320|321|322|330|361|363|403+233|405|501}} |
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| Section8 = {{Chembox Related |
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| FlashPtC =47 |
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| OtherAnions = ]<br />] |
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| FlashPt_ref = <ref name=chemicalland21/> |
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| Function = ]s |
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| OtherFunctn = ] |
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| OtherCpds = ]<br />] |
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| OtherFunction_label = ]s |
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| OtherFunction = {{ubl|]|]|]|]|]|]}} |
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| OtherCompounds = {{ubl|]|]|]}} |
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'''Ethyl 2-bromoacetate''' is the ] with the formula CH<sub>2</sub>BrCO<sub>2</sub>C<sub>2</sub>H<sub>5</sub>. It is the ] ] of ] and is prepared in two steps from ].<ref>{{OrgSynth | author = Natelson, S.; Gottfried, S. | title = Ethyl Bromoacetate | collvol = 3 | collvolpages = 381 | year = 1955 | prep = cv3p0381}}</ref> |
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'''Ethyl bromoacetate''' is the ] with the formula {{chem2|BrCH2CO2CH2CH3|auto=1}}. It is the ] ] of ] and is prepared in two steps from ].<ref>{{OrgSynth | author = Natelson, S. | author2 = Gottfried, S. | title = Ethyl Bromoacetate | collvol = 3 | collvolpages = 381 | year = 1955 | prep = cv3p0381}}</ref> It is a ] and has a fruity, pungent odor.<ref name=Criswell>{{cite journal | pmid = 6968976 | year = 1980 | last1 = Criswell | first1 = DW | last2 = McClure | first2 = FL | last3 = Schaefer | first3 = R | last4 = Brower | first4 = KR | title = War gases as olfactory probes | volume = 210 | issue = 4468 | pages = 425–6 | journal = Science | doi=10.1126/science.6968976| bibcode = 1980Sci...210..425C}}</ref> It is also a highly toxic ] and may be fatal if inhaled. |
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==Applications== |
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==Applications== |
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Ethyl bromoacetate is listed by the ] as a ], and was first employed for that purpose by French police in 1912.<ref>, Chapter 3, Biological and Chemical agents, WHO Guidance]</ref> The French army used rifle grenades 'grenades lacrymogènes'<ref>{{Cite web|url=https://www.nouvelobs.com/culture/20050408.OBS3424/plaidoyer-pour-la-guerre-des-gaz.html|title = Plaidoyer pour la guerre des gaz|date = 15 April 2005}}</ref> filled with this gas against the Germans beginning in August 1914, but the weapons were largely ineffective, even though ethyl bromoacetate is twice as toxic as chlorine.<ref>{{Cite web|url=https://www.nouvelobs.com/culture/20050408.OBS3424/plaidoyer-pour-la-guerre-des-gaz.html|title = Plaidoyer pour la guerre des gaz|date = 15 April 2005}}</ref>{{efn|The small quantities of gas delivered, roughly 19 cm<sup>3</sup> per cartridge, were not even detected by the Germans. The stocks were rapidly consumed.]]}} In the early months of the war the British also used the weaponized use of tear gas agents and more toxic gasses including ].<ref>{{Cite web|url=http://www.historylearningsite.co.uk/world-war-one/the-western-front-in-world-war-one/poison-gas-and-world-war-one/|title = Poison Gas and World War One}}</ref> The German army then used these attacks to justify their subsequent employment of it as ] or warning agent in odorless, toxic gases and ]s in 1915 under the German code '']'' (White Cross).<ref name="heller84">{{cite web |last = Heller |first = Charles E.|date = September 1984 |url = http://www-cgsc.army.mil/carl/resources/csi/Heller/HELLER.asp |title = Chemical Warfare in World War I: The American Experience, 1917-1918 |publisher = Combat Studies Institute |access-date = 2007-08-02 |url-status = dead |archive-url = https://web.archive.org/web/20070704205655/http://www-cgsc.army.mil/carl/resources/csi/Heller/HELLER.asp |archive-date = 2007-07-04}}</ref> |
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In ], ethyl bromoacetate was used as a ] and ] agent for ] under the German code ''''']''''' (White Cross), and later as ] or warning agent in odourless, toxic gases. It is listed by the ] as a ], and was first employed for that purpose by French police in 1912. The French may have employed gas grenades of this substance in 1914 during ]. The German army then used this attack to justify their subsequent employment of ]s in 1915.<ref name="heller84">{{cite web |
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| last=Heller | first=Charles E. | date=September 1984 |
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| url=http://www-cgsc.army.mil/carl/resources/csi/Heller/HELLER.asp |
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| title=Chemical Warfare in World War I: The American Experience, 1917-1918 |
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| publisher=Combat Studies Institute |
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| accessdate=2007-08-02 }}</ref> |
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In ], it is a versatile ]. Its major application involves the ], wherein it reacts with ] to form a zinc ]. The resulting BrZnCH<sub>2</sub>CO<sub>2</sub>Et condenses with ] compounds to give a β-hydroxy-esters. |
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In ], it is a versatile ]. Its major application involves the ], wherein it reacts with ] to form a zinc ]. The resulting {{chem2|BrZnCH2CO2CH2CH3}} condenses with ] compounds to give a β-hydroxy-esters. |
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It is also the starting point for the preparation of several other reagents. For example, the related ] (prepared by reaction with ]) is commonly used to prepare alpha,beta-] ]s from carbonyl compounds such as ]:<ref> A student lab procedure for the Wittig sequence shown, only using the related methyl ester.</ref> |
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It is also the starting point for the preparation of several other reagents. For example, the related ] (prepared by reaction with ]) is commonly used to prepare alpha,beta-] ]s from carbonyl compounds such as ]:<ref>A student lab procedure for the Wittig sequence shown, only using the related methyl ester.</ref> |
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==References== |
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==References== |
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{{Reflist}} |
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<references/> |
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==Footnotes== |
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{{notelist|1}} |
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==External links== |
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{{Chemical agents}} |
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