1-chloro-3-methylbutane - 1-cloro-3-metilbutano

1-chloro-3-methylbutane
1-chloro-3-methylbutane.tif
1-chloro-3-methylbutane-3D.gif
IUPAC name
1-chloro-3-methylbutane
General
Other names Isoamyl
chloride 3-methylbutyl
chloride Isopentyl chloride
4-chloro-2-methylbutane
1-chloro-3,3-dimethylpropane
Semi-developed formula CH 3 -CH (CH 3 ) -CH 2 -CH 2 Cl
Molecular formula C5H11Cl
Identifiers
CAS number 107-84-6[1]
ChemSpider 7605
PubChem 7893
SOME 87D3ZL9F7A
Physical properties
Appearance liquid colorless
Density 880 kg/; 0,88 g/cm³
Molar mass 106.59 g / mol
Melting point −104 °C (169 K)
Boiling point 100 °C (373 K)
Vapor pressure 46,2 ± 0,2 mmHg
Refractive index (n D ) 1,409
Chemical properties
Solubility in water 320 mg / L
log P 2,91
Family Haloalkane
Dangerousness
Flash point 289 K (16 °C)
NFPA 704

NFPA 704.svg

3
0
0
Explosive limits 1,5% - 7,4%
Related compounds
cloroalcanos 1-chloro-2-methylpropane
1-chloro-4-methylpentane
dichloroalkanes 1,3-dichlorobutane
chloroalkenes 1-cloro-3-metil-2-buteno
Values ​​in the SI and under standard conditions
(25 and 1 atm ), unless otherwise indicated.

The 1-chloro-3-methylbutane is an organic compound of molecular formula C 5 H 11 Cl . It is a haloalkane nonlinear five carbons where one atom of chlorine is attached to one of the terminal carbons. [ 2 ] [ 3 ] [ 4 ]

This compound also receives the names of isoamyl chloride , chloride 3-methylbutyl , isopentyl chloride , 4-chloro-2-methylbutane and 1-chloro-3,3-dimethylpropane . [ 2 ]

Physical and chemical properties

A room temperature , 1-chloro-3-methylbutane is a liquid nearly colorless with a density of 0.880 g / cm³ , lower than the water but greater than that of the ethanol . It has its boiling point at 100 ° C and its melting point at -104 ° C.

The value of the logarithm of its partition coefficient , log P ≃ 2.91, indicates that it is more soluble in nonpolar solvents than in polar solvents . Its solubility in water is very low, of the order of 320 mg / L . [ 3 ] It is incompatible with strong oxidizing agents. [ 5 ]

Synthesis

The synthesis of 1-chloro-3-methylbutane can be made from 3-methyl-1-butanol using silica chloride (SiO 2 -Cl) as the chlorinating agent. With this method a yield of 82% is achieved . [ 6 ] This reaction can also be carried out using carbon tetrachloride and methanol in the presence of molybdenum hexacarbonyl as a catalyst at 150 ° C. As products, in addition to 1-chloro-3-methylbutane, the esters of methyl isovalerate and isoamyl isolvalerate are obtained . [ 7 ]

Applications

1-Chloro-3-methylbutane has been used in coupling reactions with alkylboron compounds (Suzuki-Miyaura reaction) promoted by complexes of palladium and nickel . [ 8 ] [ 9 ] Also in the preparation of alkanesulfonyl chlorides which are obtained by free radical addition when reacted with chlorine and sulfur dioxide . Generally, a mixture of isomers is formed, the ratio of which is influenced by the stability of the intermediate alkyl radicals. [ 10 ]

This chloroalkane has also been used in the synthesis of substituted 1,2,4- triazole and 1,2,4-thiadiazole derivatives, compounds that have biological activity . [ 11 ] Other applications are in the production of 2,3,3,3-tetrafluoro-1-propene —compound used as a refrigerant and extinguishing agent in fires— [ 12 ] and as a solvent in the manufacture of polymers based in halogenated isoolefins [ 13 ] and in thermoplastic elastomers . [ 14 ]

Precautions

1-Chloro-3-methylbutane is a highly flammable liquid and vapor compound with a flash point of 16 ° C. [ 5 ]

See also

The following compounds are isomers of 1-chloro-3-methylbutane:

References

  1. CAS number
  2. a b 1-Chloro-3-methylbutane (PubChem)
  3. a b Isoamyl Chloride ( ChemSpider )
  4. 1-Chloro-3-methylbutane (Chemical Book)
  5. a b 1-Chloro-3-methylbutane. Safety data sheet (TCI America)
  6. Mohanazadeh, F.; Momeni, A.R. (1996). «Conversion of alcohols to alkyl chlorides with silica chloride». Organic Preparations and Procedures International 28 (4): 492-494. Consultado el 15 de febrero de 2020.
  7. Khusnutdinov, R.I.; Shchadneva, N.A.; Burangulova, R.Yu.; Muslimov, Z.S.; Dzhemilev, U.M. (2006). «Oxidation of monohydric and dihydric alcohols with CCl4 catalyzed by molybdenum compounds». Russian Journal of Organic Chemistry 42 (11): 1615-1621. Consultado el 15 de febrero de 2020.
  8. Kantchev, E. A. B.; Organ, M. G. (2009). «48.1.2.2.3 Variation 3: Couplings of Alkyl Boron Compounds (Suzuki–Miyaura Reaction) Mediated by Palladium and Nickel». Science of Synthesis 48: 63. Consultado el 15 de febrero de 2020.
  9. Sandrock, D.L. (2013). «1.1.4.2.1.4 With Alkyl Electrophiles». Science of Synthesis: Cross Coupling and Heck-Type Reactions 1: 328. Consultado el 15 de febrero de 2020.
  10. Drabowicz, J.; Kiełbasiński, P.; Łyżwa, P.; Zając, A.; Mikołajczyk, M. (2008). «39.1.2.1.1.1 Variation 1: Reaction of Alkanes with Chlorine and Sulfur Dioxide or Trioxide». Science of Sy7nthesis 39: 20.
  11. Dilanyan, E.R.; Hovsepyan, T.R.; Melik-Ohanjanyan, R.G. (2008). «Synthesis of some substituted 1,2,4-triazole and 1,3,4-thiadiazole derivatives». Chemistry of Heterocyclic Compounds 44 (11): 1395-1397. Consultado el 15 de febrero de 2020.
  12. Method for preparing 2,3,3,3-tetrafluoro-1-propene and method for recycling 2-chloro-3,3,3-trifluoropropene free of impurities (2015) Abedera Tif Baba-Ahmad et al. Patente JP2018538346A
  13. Method for producing halogenated isoolefin-based polymer (2016) Kato, Y.; Ikari, Y. Patente US20180112016A1
  14. Process for producing thermoplastic elastomer, and thermoplastic elastomer (2016) Kato, Y.; Ikari, Y. Patente US10472452B2