1-chloro-3-methylbutane - 1-cloro-3-metilbutano
chloride Isopentyl chloride
|Semi-developed formula||CH 3 -CH (CH 3 ) -CH 2 -CH 2 Cl|
|Density||880 kg/m³; 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|
|Solubility in water||320 mg / L|
|Flash point||289 K (16 °C)|
|NFPA 704|| |
|Explosive limits||1,5% - 7,4%|
|cloroalcanos|| 1-chloro-2-methylpropane |
|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 ]
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 ]
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 ]
The following compounds are isomers of 1-chloro-3-methylbutane:
- CAS number
- 1-Chloro-3-methylbutane (PubChem)
- Isoamyl Chloride ( ChemSpider )
- 1-Chloro-3-methylbutane (Chemical Book)
- 1-Chloro-3-methylbutane. Safety data sheet (TCI America)
- 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.
- 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.
- Kantchev, E. A. B.; Organ, M. G. (2009). «188.8.131.52.3 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.
- Sandrock, D.L. (2013). «184.108.40.206.1.4 With Alkyl Electrophiles». Science of Synthesis: Cross Coupling and Heck-Type Reactions 1: 328. Consultado el 15 de febrero de 2020.
- Drabowicz, J.; Kiełbasiński, P.; Łyżwa, P.; Zając, A.; Mikołajczyk, M. (2008). «220.127.116.11.1.1 Variation 1: Reaction of Alkanes with Chlorine and Sulfur Dioxide or Trioxide». Science of Sy7nthesis 39: 20.
- 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.
- 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
- Method for producing halogenated isoolefin-based polymer (2016) Kato, Y.; Ikari, Y. Patente US20180112016A1
- Process for producing thermoplastic elastomer, and thermoplastic elastomer (2016) Kato, Y.; Ikari, Y. Patente US10472452B2