Wikipedia

4-Chloro-2-pentene

4-Chloro-2-pentene is an organic compound with the formula C5H9Cl. Its molecule is a linear chain of five carbon atoms, with a double bond between carbons 2 and 3 and a chlorine attached to carbon 4.

4-Chloro-2-pentene
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C5H9Cl/c1-3-4-5(2)6/h3-5H,1-2H3/b4-3+ ☒N
    Key: FKKCIOTUMHPTSB-ONEGZZNKSA-N ☒N
  • InChI=1S/C5H9Cl/c1-3-4-5(2)6/h3-5H,1-2H3/b4-3+
    Key: FKKCIOTUMHPTSB-ONEGZZNKSA-N
  • CC=CC(C)Cl
Properties
C5H9Cl
Molar mass 104.58 g·mol−1
Density 0.8988 g/cm3 at 20 °C[1]
Boiling point 97 °C (207 °F; 370 K)[1]
1.4322[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Physical and chemical properties

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At room temperature, 4-chloro-2-pentene is a liquid with a density of ca. 0.9 g/cm3 and a boiling point of 97 °C.[1]

Synthesis

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4-Chloro-2-pentene can be synthesized from its corresponding alcohol (3-pentene-2-ol) or from 1,3-pentadiene. In the latter case, 4-chloro-2-pentene can be obtained with a yield of 97%.[2]

Uses

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4-Chloro-2-pentene has been used to prepare quaternary ammonium salts based on N,N,N',N'-tetramethyldiaminomethane, an intermediate in the manufacture of ionol (2,6-di-tert-butyl-4-methylphenol).[2][3]

4-Chloro-2-pentene readily reacts with stannyl lithium at low temperature to provide respective allyl stannanes.[4] Likewise, allyl silanes can be prepared from 4-chloro-2-pentene by silylation of the corresponding Grignard reagents with an appropriate chlorosilane.[5]

References

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  1. ^ a b c d Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 3.116. ISBN 9781498754293.
  2. ^ a b Levashova, V. I.; Nikonorova, N. I. (2009). "Synthesis and properties of quaternary ammonium salts based on N,N′-tetramethyldiaminomethane and 4-chloro-2-pentene". Petroleum Chemistry. 49 (3): 250–253. doi:10.1134/S0965544109030116. S2CID 94555175.
  3. ^ Rakhmatullin, R. R.; Levashova, V. I.; Dekhtyar', T. F. (2013). "Synthesis and properties of quaternary ammonium salts on the basis of piperidine". Petroleum Chemistry. 53 (2): 134–138. doi:10.1134/S0965544113020102. S2CID 96967040.
  4. ^ Carreira; Drabowicz; Fuerstner; Krause; Moloney; Carreira; Fuerstner; Molander; Thomas; Echavarren; Gouverneur; Hopkinson; Hou; Landelle; López-Carrillo; Łyz˙Wa; Paquin; Peng; Schatz; Seßler; Snaith; Wong; Yeung; Zhang, eds. (2011). "Product Subclass 28: Allylstannanes". Knowledge Updates 2011/2. doi:10.1055/sos-SD-105-00108. ISBN 9783131642813.
  5. ^ Fleming; Ley, eds. (2002). "Product Subclass 40: Allylsilanes". Category 1, Organometallics. doi:10.1055/sos-SD-004-00909. ISBN 9783131121714.
 

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