Chloroacetone

Chloroacetone
IUPAC name Chloropropanone
Other names Acetonyl chloride, chloropropanone, 1-chloro-2-propanone, monochloroacetone, 1-chloro-2-ketopropane, 1-chloro-2-oxypropane UN 1695
Identifiers
CAS number	78-95-5 Y
PubChem	6571
ChemSpider	6323 Y
UNII	60ZTR74268 Y
ChEBI	CHEBI:47220 Y
RTECS number	UC0700000
Jmol-3D images	Image 1
SMILES ClCC(=O)C
InChI InChI=1S/C3H5ClO/c1-3(5)2-4/h2H2,1H3 Y Key: BULLHNJGPPOUOX-UHFFFAOYSA-N Y InChI=1/C3H5ClO/c1-3(5)2-4/h2H2,1H3 Key: BULLHNJGPPOUOX-UHFFFAOYAY
Properties
Molecular formula	C3H5ClO
Molar mass	92.52 g mol−1
Appearance	Colorless liquid, oxidizes to amber
Density	1.15 g/cm3 at 20°C
Melting point	-44.5 °C, 229 K, -48 °F
Boiling point	119 °C, 392 K, 246 °F
Solubility in water	10 g/100 mL at 20 °C
Solubility	alcohol, ether, chloroform[1]
Vapor pressure	1.5 kPa
Hazards
Flash point	35 °C
Autoignition temperature	610 °C
Explosive limits	3.4% - ?[2]
LD50	100 mg/kg (rats, oral)[3]
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Chloroacetone is a chemical compound with the formula CH₃COCH₂Cl. At STP it is a colourless liquid with a pungent odour.^[4] On exposure to light, it turns to a dark yellow-amber colour.^[5] It was used as a tear gas in World War I.^[6]

Applications

Chloroacetone is used to make dye couplers for colour photography, and is an intermediate in chemical manufacturing^[3]. It is also used in the Feist-Benary synthesis of furans^[7].

See also

• Use of poison gas in World War I
• Bromoacetone

References

1. ^ Lide, David R. (1998). Handbook of Chemistry and Physics (87 ed.). Boca Raton, FL: CRC Press. pp. 3–100. ISBN 0849305942. 
2. ^ "ICSC:NENG0760 International Chemical Safety Cards (WHO/IPCS/ILO) CDC/NIOSH". Center for Disease Control. 2006-10-11. http://www.cdc.gov/niosh/ipcsneng/neng0760.html. Retrieved 2009-04-17. 
3. ^ ^{a b} Hathaway, Gloria J.; Proctor, Nick H. (2004). Proctor and Hughes' Chemical Hazards of the Workplace (5 ed.). Wiley-Interscience. pp. 143–144. ISBN 9780471268833. http://books.google.com/?id=y3-Ef3y53PkC&pg=PA143&dq=Chloroacetone. Retrieved 2009-04-16. 
4. ^ "Occupational Safety and Health Guideline for Chloroacetone". U.S. Department of Labor - Occupational Safety & Health Administration. http://www.osha.gov/SLTC/healthguidelines/chloroacetone/recognition.html. Retrieved 2008-06-06. 
5. ^ "CHLOROACETONE". International Programme on Chemical Safety. http://www.inchem.org/documents/icsc/icsc/eics0760.htm. Retrieved 2008-06-06. 
6. ^ Haber, Ludwig Fritz (1986). The Poisonous Cloud: Chemical Warfare in the First World War. Oxford University press. ISBN 0198581424. 
7. ^ Li, Jie-Jack; Corey, E. J. (2004). Name Reactions in Heterocyclic Chemistry. Wiley-Interscience. pp. 160. ISBN 9780471302155. http://books.google.com/?id=1N-MZVSesTcC&pg=PA160&dq=Chloroacetone. Retrieved 2009-04-16. 

External links

• The Halogenation of Carbonyls

This article about an organic compound is a stub. You can help Wikipedia by expanding it.v · Categories: Organochlorides Lachrymatory agents World War I chemical weapons Ketones Organic compound stubs Wikimedia Foundation. 2010. Игры ⚽ Поможем решить контрольную работу Deportivo Pinozá Horace Smith (New Brunswick politician) Look at other dictionaries: chloroacetone — chloracetonas statusas T sritis chemija formulė ClCH₂COCH₃ atitikmenys: angl. chloroacetone rus. хлорацетон ryšiai: sinonimas – chlorpropanonas …   Chemijos terminų aiškinamasis žodynas chloroacetone — /klawr oh as i tohn , klohr /, n. a colorless, lachrymatory, poisonous liquid, C3H5ClO, used chiefly in organic synthesis and in the manufacture of insecticides and perfumes. [CHLORO 2 + ACETONE] * * * …   Universalium chloroacetone — noun The chlorinated derivative of acetone CH CO CHCl used in tear gas and in organic synthesis …   Wiktionary chloroacetone — /klawr oh as i tohn , klohr /, n. a colorless, lachrymatory, poisonous liquid, C3H5ClO, used chiefly in organic synthesis and in the manufacture of insecticides and perfumes. [CHLORO 2 + ACETONE] …   Useful english dictionary Phenylacetone — Phenylacetone …   Wikipedia Chloroform — IUPAC name …   Wikipedia Poison gas in World War I — The use of poison gas in World War I was a major military innovation. The gases ranged from disabling chemicals, such as tear gas and the severe mustard gas, to lethal agents like phosgene and chlorine. This chemical warfare was a major component …   Wikipedia Thiazole — Chembox new ImageFile = Thiazole numbering.png ImageFile1 = Thiazole3d.png ImageSize = 100px IUPACName = OtherNames = Section1 = Chembox Identifiers CASNo = 288 47 1 PubChem = SMILES = N1=CSC=C1 Section2 = Chembox Properties Formula = MolarMass …   Wikipedia White Cross (chemical warfare) — White Cross (Weisskreuz) is a World War I chemical warfare agent consisting of one or more lachrymatory agents: bromoacetone (BA), bromobenzyl cyanide (Camite), bromomethyl ethyl ketone (homomartonite, Bn stoff), chloroacetone (Tonite, A stoff),… …   Wikipedia Chloraceton — Strukturformel Allgemeines Name Chloraceton Andere Namen …   Deutsch Wikipedia 18+ © Academic, 2000-2024 Contact us: Technical Support, Advertising Dictionaries export, created on PHP, Joomla, Drupal, WordPress, MODx. Mark and share Search through all dictionaries Translate… Search Internet Share the article and excerpts Direct link … Do a right-click on the link above and select “Copy Link”