4-Chloro-2-pentene

4-Chloro-2-pentene
Identifiers
CAS Number	1458-99-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	4517784 ;
PubChem CID	5365840;
CompTox Dashboard (EPA)	DTXSID401350399 ;
	InChI InChI=1S/C5H9Cl/c1-3-4-5(2)6/h3-5H,1-2H3/b4-3+ Key: FKKCIOTUMHPTSB-ONEGZZNKSA-N ; InChI=1S/C5H9Cl/c1-3-4-5(2)6/h3-5H,1-2H3/b4-3+ Key: FKKCIOTUMHPTSB-ONEGZZNKSA-N;
	SMILES CC=CC(C)Cl;
Properties
Chemical formula	C5H9Cl
Molar mass	104.58 g·mol−1
Density	0.8988 g/cm3 at 20 °C
Boiling point	97 °C (207 °F; 370 K)
Refractive index (nD)	1.4322
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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.

Physical and chemical properties

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

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

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

^ ^a ^b ^c ^d Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 3.116. ISBN 9781498754293.
^ ^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.
^ 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.
^ 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.
^ Fleming; Ley, eds. (2002). "Product Subclass 40: Allylsilanes". Category 1, Organometallics. doi:10.1055/sos-SD-004-00909. ISBN 9783131121714.

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[crc-1] Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 3.116. ISBN 9781498754293.

[Levashova-2] 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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