4325-49-9

Basic information

• Product Name: 2-chloro-2-methylheptane
• Synonyms: heptane, 2-chloro-2-methyl-
• CAS NO: 4325-49-9
• Molecular Formula: C₈H₁₇Cl
• Molecular Weight: 148.6736
• Mol File: 4325-49-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 163.9°C at 760 mmHg
• Flash Point: 47.1°C
• Density: 0.864g/cm³
• Vapor Pressure: 2.64mmHg at 25°C
• Refractive Index: 1.424
• CAS DataBase Reference: 2-chloro-2-methylheptane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloro-2-methylheptane(4325-49-9)
• EPA Substance Registry System: 2-chloro-2-methylheptane(4325-49-9)

Safety Data

• Hazardous Substances Data: 4325-49-9(Hazardous Substances Data)

Upstream product

• 693-25-4 n-pentylmagnesium bromide 
• 18720-62-2 2-methyl-3-heptanol 
• 861567-70-6 3-iodo-2-methyl-heptane 
• 110-43-0 n-pentyl methyl ketone 
• 75-16-1 methylmagnesium bromide 
• 15870-10-7 2-methylhept-1-ene 
• 625-25-2 2-Methyl-2-heptanol 
• 75-36-5 acetyl chloride 
• 110-53-2 1-Bromopentane 

Downstream Products

• 1071-26-7 2,2-dimethylheptane 
• 627-97-4 2-methyl-2-heptene 
• 592-27-8 2-methylheptane 
• 15870-10-7 2-methylhept-1-ene 
• 625-25-2 2-Methyl-2-heptanol 
• 1068-19-5 4,4-dimethyl-heptane 

Relevant articles and documents

Solvolysis of 1,1-dimethyl-4-alkenyl chlorides: Evidence for π-participation

Tertiary 1,1-dimethyl-4-alkenyl chloride (1) solvolyzes with significantly reduced secondary β-deuterium kinetic isotope effect (substrate with two trideuteromethyl groups) and has a lower entropy and enthalpy of activation than the referent saturated analogue 4 (kH/kD = 1.30 ± 0.03 vs kH/kD = 1.79 ± 0.01; ΔΔH? = -9 kJ mol-1, ΔΔS? = -36 J mol-1 K-1, in 80% v/v aqueous ethanol), indicating participation of the double bond in the rate-determining step. Transition structure 1-TS computed at the MP2(fc)/6-31G(d) level of theory revealed that the reaction proceeds through a late transition state with considerably pronounced double bond participation and a substantially cleaved C-Cl bond. The doubly unsaturated compound 3 (1,1-dimethyl-4,8-alkadienyl chloride) solvolyzes with further reduction of the isotope effect, and a drastically lower entropy of activation (kH/kD = 1.14 ± 0.01; ΔS? = -152 ± 12 J mol-1 K-1, in 80% v/v aqueous ethanol), suggesting that the solvolysis of 3 proceeds by way of extended π-participation, i.e., the assistance of both double bonds in the rate-determining step.

Reactions of Saturated and Unsaturated Tertiary Alkyl Halides and Saturated Secondary Alkyl Iodides with Lithium Aluminum Deuteride. Convincing Evidence for a Single-Electron-Transfer Pathway

Reactions of saturated secondary and tertiary alkyl halides with LiAlH4 (LAH) and LiAlD4 (LAD) have been carried out, and convincing evidence for a single-electron-transfer (SET) pathway has been obtained. Reactions involving saturated alkyl halides with LAD provide a model system in which a halogen-atom radical chain process is not possible, and therefore, the observation of large quantities (in some cases >90 percent) of protium in the reduction product provides strong evidence for a radical intermediate and a SET pathway. Specifically, the reaction of 2-iodooctane (10) with LAD produced octane with a deuterium content as low as 21 percent. Also, the reaction of the tertiary halide 2-iodo-2-methylheptane (15) with LAD produced 2-methylheptane (16) with a deuterium content as low as 8 percent. The effect of stoichiometry, halogen type, and reaction vessel surface on these reactions was studied. Reaction of the unsaturated tertiary halide 6-iodo-6-methyl-1-heptene (25) with LAD was also studied and was found to proceed predominantly by a SET process involving a halogen-atom radical chain process. The possibility of a carbocation intermediate in all of these reactions is discussed.

Geminale Dialkylierung von Ketonen mit Grignard-Verbindungen und Methyltitan(IV)-chloriden

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