616-13-7 Usage
Description
1-Chloro-2-methylbutane is a halogenated organic building block that can be synthesized using 2-methylbutanol as a starting reagent. It has potential applications in the synthesis of various organic compounds due to its unique structure and properties.
Uses
Used in Organic Synthesis:
1-Chloro-2-methylbutane is used as a building block for the synthesis of various organic compounds. Its unique structure allows for the formation of Grignard reagents, which can be employed in the preparation of partially optically active (-)-alkylphenylcarbinols and partially optically active secondary carbinols.
Used in Spectroscopic Analysis:
The optically active form of 1-chloro-2-methylbutane, (+)(S)-1-chloro-2-methylbutane, has been evaluated using infrared and Raman spectroscopy in various phases (liquid, glass, and crystal). This allows for the study of its molecular structure and properties, which can be useful in understanding its behavior in different environments and potential applications.
Purification Methods
Purify the chloride by stirring vigorously with 95% H2SO4, replacing the acid when it becomes coloured, until the layer remains colourless after 12hours stirring. The amyl chloride is then washed with saturated Na2CO3 solution, then distilled water, and dried with anhydrous MgSO4, followed by filtration, and distillation through a 10-in Vigreux column (p 11). Alternatively a stream of oxygen containing 5% ozone is passed through the amyl chloride for three times as long as it takes to cause the first coloration of starch iodide paper by the exit gas. The liquid is washed with NaHCO3 solution to hydrolyze the ozonides and remove organic acids prior to drying and fractional distillation [Chien & Willard J Am Chem Soc 75 6160 1953]. The S(+)-enantiomer has b 50-51o/140mm, 100o/760, mm, [] D +1.64o (neat) [Brown et al. J Am Chem Soc 62 3437 1940]. [Beilstein 1 H 134, 1 I 46, 1 III 356, 1 IV 326.]
Check Digit Verification of cas no
The CAS Registry Mumber 616-13-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 6,1 and 6 respectively; the second part has 2 digits, 1 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 616-13:
(5*6)+(4*1)+(3*6)+(2*1)+(1*3)=57
57 % 10 = 7
So 616-13-7 is a valid CAS Registry Number.
InChI:InChI=1/C5H11Cl/c1-3-5(2)4-6/h5H,3-4H2,1-2H3
616-13-7Relevant articles and documents
Silylaminyl Radicals. Part 2. Free Radical Chain Halogenation of Hydrocarbons using N-Halogenobis(trialkylsilyl)amines
Cook, Malcolm D.,Roberts, Brian P.,Singh, Karamjit
, p. 635 - 644 (2007/10/02)
The liquid-phase halogenation of a number of hydrocarbons and of 1-chlorobutane by N-halogenobis(trialkylsilyl)amines has been studied using product analysis techniques.The reactions take place by free radical chain mechanisms which involve the propagation steps generalised in equations (A) and (B) (X=Br or Cl).At 353 K, the molar reactivities of toluene (benzylic C-H) and cyclohexane towards (R3Si)2N+RH(R3Si)2NH+R (A) R+(R3Si)2NXRX+(R3Si)2N (B) (Me3Si)2N are approximately equal and toluene is 5.2 times more reactive than perdeuteriotoluene.The relative rates of hydrogen abstraction by (Me3Si)2N and (ButMe2Si)2N from the primary, secondary, and tertiary C-H groups in 2-methylbutane show that the silylaminyl radicals are not only highly reactive but also sterically demanding.Thus, at 333 K the average primary C-H reactivity is 0.6 times that of the tertiary C-H towards attack by (Me3Si)2N, but 4.2 times that of the tertiary C-H towards attack by the more bulky (ButMe2Si)2N.Silylaminyl radicals are much more reactive in hydrogen abstraction than are analogous dialkylaminyl radicals and this difference is interpreted in terms of thermodynamic and polar effects which arise because of the ?-donor-?-acceptor nature of the trialkylsilyl substituent.
Studies on Sulphochlorination of Paraffins. IX. Regularities of the Sulphochlorination of Branched-chain Paraffins
Estel, D.,Mateew, K.,Pritzkow, W.,Schmidt-Renner, W.
, p. 262 - 268 (2007/10/02)
In the cases of 2-methylbutane and 2-methylpentane the formation of tertiary sulphochlorides in the sulphochlorination of the parent hydrocarbons could be established by means of 13C-n.m.r.-spectroscopy.The relative rates of the various C-H-bonds in 2-methylbutane, 2-methylpentane and 3-methylpentane in the sulphochlorination reaction were determined.The relative rates of the tertiary C-H-bonds in the sulphochlorination were considerably lower than the corresponding values for the chlorination of the branched-chain paraffins.