2-Chloropropionic acid

2-Chloropropionic acid
2-Chloropropionic acid
Names
Preferred IUPAC name
2-Chloropropanoic acid
Other names
α-Chloropropanoic acid
α-Chloropropionic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.009.049 Edit this at Wikidata
EC Number
  • 209-952-3
RTECS number
  • UE8575000
UNII
UN number 2511
  • InChI=1S/C3H5ClO2/c1-2(4)3(5)6/h2H,1H3,(H,5,6) checkY
    Key: GAWAYYRQGQZKCR-UHFFFAOYSA-N checkY
  • InChI=1/C3H5ClO2/c1-2(4)3(5)6/h2H,1H3,(H,5,6)
    Key: GAWAYYRQGQZKCR-UHFFFAOYAW
  • ClC(C(=O)O)C
Properties
C3H5ClO2
Molar mass 108.52 g·mol−1
Appearance Colorless liquid
Density 1.18 g/mL
Melting point −13 °C (9 °F; 260 K)
Boiling point 78 °C (172 °F; 351 K) at 10 mmHg
Miscible
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic, corrosive
GHS labelling:
GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation markGHS08: Health hazard
Danger
H301, H302, H310, H314, H331, H371, H373
P260, P261, P262, P264, P270, P271, P280, P301+P312, P301+P330+P331, P302+P350, P303+P361+P353, P304+P340, P305+P351+P338, P309+P311, P310, P311, P314, P321, P322, P330, P361, P363, P403+P233, P405, P501
Flash point 101 °C (214 °F; 374 K)
Safety data sheet (SDS) External MSDS
Related compounds
Related compounds
 Propionic acid
Chloroacetic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

2-Chloropropionic acid (2-chloropropanoic acid) is the chemical compound with the formula CH3CHClCO2H. This colorless liquid is the simplest chiral chlorocarboxylic acid, and it is noteworthy for being readily available as a single enantiomer. The conjugate base of 2-chloropropionic acid (CH3CHClCO2−), as well as its salts and esters, are known as 2-chloropropionates or 2-chloropropanoates.[1]

Preparation

Racemic 2-chloropropionic acid is produced by chlorination of propionyl chloride followed by hydrolysis of the 2-chloropropionyl chloride.[1] Enantiomerically pure (S)-2-chloropropionic acid can be prepared from L-alanine via diazotization in hydrochloric acid.[2] Other α-amino acids undergo this reaction.

Reactions

Reduction of (S)-2-chloropropionic acid with lithium aluminium hydride affords (S)-2-chloropropanol, the simplest chiral chloro-alcohol. This alcohol undergoes cyclization upon treatment with potassium hydroxide, which causes dehydrohalogenation to give the epoxide, (R)-propylene oxide (methyloxirane).[3]

2-Chloropropionyl chloride reacts with isobutylbenzene to give, after hydrolysis, ibuprofen.[1]

Safety

In general, α-halocarboxylic acids and their esters are good alkylating agents and should be handled with care. 2-Chloropropionic acid is a neurotoxin.[4]

See also

References

  1. ^ a b c Samel, Ulf-Rainer; Kohler, Walter; Gamer, Armin Otto; Keuser, Ullrich (2005). "Propionic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_223. ISBN 978-3527306732.
  2. ^ Koppenhoefer, Bernhardt; Schurig, Volker (1988). "(S)-2-Chloroalkanoic Acids of High Enantiomeric Purity from (S)-2-Amino Acids: (S)-2-Chloropropanoic Acid". Organic Syntheses. 66: 151. doi:10.15227/orgsyn.066.0151.
  3. ^ Bernhard Koppenhoefer; Volker Schurig (1988). "(R)-Alkyloxiranes of High Enantiomeric Purity from (S)-2-Chloroalkanoic Acids Via (S)-2-Chloro-1-Alkanols: (R)-Methyloxirane". Organic Syntheses. 66: 160. doi:10.15227/orgsyn.066.0160.
  4. ^ Simpson MG, Wyatt I, Jones HB, Gyte AJ, Widdowson PS, Lock EA (1996). "Neuropathological changes in rat brain following oral administration of 2-chloropropionic acid". Neurotoxicology. 17 (2): 471–480. PMID 8856742.

Read other articles:

Commentarii de Bello Gallico

Commentarii de Bello Gallico (Commentaries on the Gallic War) Halaman pertama De bello Gallico dalam manuskrip tahun 1469PengarangJulius Caesar, Aulus Hirtius (VIII)BahasaLatin KlasikSubjekSejarah, etnografi, sejarah militerPenerbitJulius CaesarTanggal terbit58–49 SMDiikuti olehCommentarii de Bello Civili  Commentarii de Bello Gallico (Indonesia: Komentar mengenai Perang Galiacode: id is deprecated ) atau Bellum Gallicum (Indonesia: Perang Galiacode: id is deprecated ) adalah...

 

 

Georgios Samaras

Georgios Samaras Informasi pribadiTanggal lahir 21 Februari 1985 (umur 39)Tempat lahir Heraklion, YunaniTinggi 1,93 m (6 ft 4 in)Posisi bermain StrikerInformasi klubKlub saat ini CelticNomor 9Karier junior1994–2000 OFI Crete2000–2002 HeerenveenKarier senior*Tahun Tim Tampil (Gol)2002–2006 Heerenveen 88 (25)2006–2008 Manchester City 55 (8)2008 → Celtic (pinjaman) 16 (5)2008– Celtic 109 (32)Tim nasional‡2004–2006 Yunani U-21 5 (0)2006– Yunani 52 (7) * Pena...

 

 

Idol Star Athletics Championships

Idol Star Athletics ChampionshipsGenreOlahragaNegara asalKorea SelatanBahasa asliKoreaJmlh. seri17Rilis asliJaringanMBCRilis25 September 2010 (2010-09-25) –sekarang Idol Star Athletics Championships (Hangul: 아이돌스타 육상 선수권 대회) adalah sebuah acara televisi Korea Selatan yang disiarkan pertama kali pada tahun 2010. Acara tersebut menampilkan para selebritas, terutama penyanyi fan grup idola pop Korea, yang berkompetisi dalam lomba multi-olahraga. Acar...

كريستينا الصورية

هذه المقالة يتيمة إذ تصل إليها مقالات أخرى قليلة جدًا. فضلًا، ساعد بإضافة وصلة إليها في مقالات متعلقة بها. (يونيو 2021) القديسة كريستينا من صور القديسة كريستينا، من صنع موريز سشلاشتر، (حوالي 1889) معلومات شخصية الميلاد أواخر القرن 3صور، لبنان الوفاة 300 ب.م.بولسينا  مواطنة روما ...

 

 

The Ne'er-do-Weel

This article is about the play. For other uses, see Ne'er do well. Cabinet card of W.S. Gilbert in about 1880 by Elliott & Fry The Ne'er-do-Weel is a three-act drama written by the English dramatist W. S. Gilbert. It is the second of three plays that he wrote at the request of the actor Edward Sothern. The story concerns Jeffery Rollestone, a gentleman who becomes a vagabond after Maud, the girl he loves, leaves him. He meets Gerard, an old school chum who arranges for him to have a good ...

 

 

Kinsale Head gas field

Kinsale Head gas fieldCountryIrelandRegionCeltic SeaOffshore/onshoreOffshoreOperatorsKinsale Energy LimitedField historyDiscovery1971Start of productionOctober 1978Peak year1995[1]AbandonmentJuly 2020ProductionPeak of production (gas; billion cubic meters per year)2.8 The Kinsale Head gas field is a depleted offshore natural gas field in the Celtic Sea, located 50 km (31 mi) off the southern coast of County Cork, Ireland. Discovered in 1971[1][2] near the Ol...

Международный географический союз

Международный географический союз Тип Международная организация Дата основания 1922 Расположение Дели, Индия Сфера деятельности География Сайт igu-online.org  Медиафайлы на Викискладе Почтовая марка Бразилии 1956 года, посвящённая XVIII Международному географическому конгрес�...

 

 

Roma 12

Roma 12Surat Roma 11:33-12:5 pada Codex Carolinus edisi Tischendorf (Monumenta, halaman 155).KitabSurat RomaKategoriSurat-surat PaulusBagian Alkitab KristenPerjanjian BaruUrutan dalamKitab Kristen6← pasal 11 pasal 13 → Roma 12 (disingkat Rom 12) adalah bagian Surat Paulus kepada Jemaat di Roma dalam Perjanjian Baru di Alkitab Kristen. Pengarangnya adalah Rasul Paulus, tetapi dituliskan oleh Tertius, seorang Kristen yang saat itu mendampingi Paulus.[1][2] Teks Roma ...

 

 

Glasiasi Huron

Ilustrasi glasiasi Huron yang terjadi 2,5 miliar tahun yang lalu, rata-rata suhu terendah Bumi pada glasiasi ini berlangsung 100 juta tahun setelah permulaan glasiasi Huron.[1] Glasiasi Huron (atau glasiasi Makganyene)[2] adalah suatu peristiwa glasiasi yang berlangsung dari 2,5 miliar tahun yang lalu hingga 2,1 miliar tahun yang lalu[3] pada periode Siderium dan Riasium pada masa Paleoproterozoikum. Glasiasi Huron terjadi setelah peristiwa oksigenasi besar yang mening...

Capitol Hill, Seattle

Neighborhood in Seattle, Washington, United StatesCapitol HillNeighborhoodCapitol Hill as seen from 9th Avenue and Pine Street, looking eastCapitol Hill's location in SeattleCountryUnited StatesStateWashingtonCitySeattleCity CouncilDistrict 3Neighborhood CouncilEast DistrictPolice DistrictEast Precinct, E1-3Established[1]February 4, 1886 (annexation by Seattle)Founded byJames A. MooreNamed forPotential state capitolArea[2] • Total1.64 sq mi (4.2 km2...

 

 

Синелобый амазон

Синелобый амазон Научная классификация Домен:ЭукариотыЦарство:ЖивотныеПодцарство:ЭуметазоиБез ранга:Двусторонне-симметричныеБез ранга:ВторичноротыеТип:ХордовыеПодтип:ПозвоночныеИнфратип:ЧелюстноротыеНадкласс:ЧетвероногиеКлада:АмниотыКлада:ЗавропсидыКласс:Пт�...

 

 

Diocese of Pontus

Diocese of the Roman Empire For other uses, see Pontus. Diocese of PontusDioecesis PonticaΔιοίκησις ΠόντουDiocese of the Roman Empire314–535548–7th centuryThe Diocese of Pontus c. 400.CapitalAmaseiaHistorical eraLate Antiquity• Established 314• replaced by the theme system 660s Today part of Turkey The Diocese of Pontus (Latin: Dioecesis Pontica, Greek: Διοίκησις Πόντου/Ποντικῆς) was a diocese of the later Roman Empire, incorporati...

中华人民共和国国家元首列表

  提示：此条目页的主题不是中華人民共和國最高領導人。 中华人民共和国 中华人民共和国政府与政治系列条目 执政党 中国共产党 党章、党旗党徽 主要负责人、领导核心 领导集体、民主集中制 意识形态、组织 以习近平同志为核心的党中央 两个维护、两个确立 全国代表大会 （二十大） 中央委员会 （二十届） 总书记：习近平 中央政治局 常务委员会 中央书记处 �...

 

 

美国众议院

此條目需要补充更多来源。 (2021年7月4日)请协助補充多方面可靠来源以改善这篇条目，无法查证的内容可能會因為异议提出而被移除。致使用者：请搜索一下条目的标题（来源搜索：美国众议院 — 网页、新闻、书籍、学术、图像），以检查网络上是否存在该主题的更多可靠来源（判定指引）。 美國眾議院 United States House of Representatives第118届美国国会众议院徽章 众议院旗...

 

 

2012 Missouri State Bears football team

American college football season 2012 Missouri State Bears footballConferenceMissouri Valley Football ConferenceRecord3–8 (3–5 MVFC)Head coachTerry Allen (7th season)Offensive coordinatorRob Christophel (7th season)Offensive schemeSpreadDefensive coordinatorD. J. Vokolek (7th season)Base defense3–4Home stadiumPlaster Sports ComplexSeasons← 20112013 → 2012 Missouri Valley Football Conference standings vte Conf Overall Team   W ...

Population census in Hong Kong

Population census in Hong KongCensus and Statistics DepartmentHKSARFormed1967Headquarters21/F, Wanchai Tower,12 Harbour Road,Wan Chai, Hong Kongvte Population censuses / by-censuses in Hong Kong are conducted by the Census and Statistics Department (C&SD) of the Hong Kong SAR Government. The aim is to provide up-to-date benchmark statistics on the demographic and socio-economic characteristics of the population and on its geographical distribution. Since 1961, a population census has bee...

 

 

United States Secretary of Housing and Urban Development

Head of the U.S. Dept. of Housing and Urban Development; member of the Cabinet United States Secretary of Housing and Urban DevelopmentSeal of the departmentFlag of the departmentIncumbentAdrianne TodmanActing since March 22, 2024Department of Housing and Urban DevelopmentStyleMadam Secretary (informal)The Honorable (formal)Member ofCabinetReports toPresidentSeatRobert C. Weaver Federal Building, Washington, D.C.AppointerThe Presidentwith Senate advice and consentTerm lengthNo fixed...

 

 

Led Zeppelin I

Led ZeppelinAlbum studio karya Led ZeppelinDirilis12 Januari 1969DirekamOktober 1968, Olympic Studios, LondonGenreHard rock, heavy metal, blues-rockDurasi44:26BahasaInggrisLabelAtlanticProduserJimmy PageKronologi Led Zeppelin Led Zeppelin(1969) Led Zeppelin II(1969)Led Zeppelin II1969 Singel dalam album Led Zeppelin I Good Times Bad Times/Communication BreakdownDirilis: 1969 (US) Led Zeppelin adalah album pertama dari band asal Inggris, Led Zeppelin. Album ini direkam pada bulan Oktober 1...

2014 United States Grand Prix

2014 United States Grand Prix Race 17 of 19 in the 2014 Formula One World Championship← Previous raceNext race → Layout of the Circuit of the AmericasRace details[1][2]Date 2 November 2014Official name 2014 Formula 1 United States Grand PrixLocation Circuit of the Americas, Travis County, Austin, TexasCourse Permanent racing facilityCourse length 5.513 km (3.426 miles)Distance 56 laps, 308.405[n 1] km (191.634 miles)Weather SunnyAttendance 107,...

 

 

2012 Cardiff Council election

Local election in Cardiff, Wales 2012 Cardiff City and County Council election ← 2008 3 May 2012 2017 → All 75 seats to Cardiff Council38 seats needed for a majority   First party Second party Third party   Leader Heather Joyce Rodney Berman David Walker Party Labour Liberal Democrats Conservative Leader's seat Llanrumney Plasnewydd Lisvane Seats before 14 35 17 Seats won 46/75 16/75 7/74 Seat change 32 19 10 Popular vote 36,148 15,878 ...