17302-37-3

Basic information

• Product Name: Dimethyldecane, 2,2-
• Synonyms: Dimethyldecane, 2,2-
• CAS NO: 17302-37-3
• Molecular Formula: C₁₂H₂₆
• Molecular Weight: 170.33
• Product Categories: Aliphatics, Miscellaneous Reagents
• Mol File: 17302-37-3.mol

Chemical Properties

• Melting Point: -50.8°C (estimate)
• Boiling Point: 201°C
• Flash Point: 70.1°C
• Appearance: /
• Density: 0.7406
• Vapor Pressure: 0.467mmHg at 25°C
• Refractive Index: 1.4169
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Dimethyldecane, 2,2-(CAS DataBase Reference)
• NIST Chemistry Reference: Dimethyldecane, 2,2-(17302-37-3)
• EPA Substance Registry System: Dimethyldecane, 2,2-(17302-37-3)

Safety Data

• Hazardous Substances Data: 17302-37-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Dimethyldecane, 2,2is used as a key component in the synthesis of various pharmaceutical compounds. Its unique structural properties allow it to serve as an intermediate or building block in the development of new drugs, contributing to the advancement of medical treatments.
Used in Drug Manufacturing:
In the manufacture of drugs, Dimethyldecane, 2,2plays a crucial role as a raw material or precursor in the production process. Its compatibility with other chemical compounds and its ability to undergo various chemical reactions make it an essential ingredient in the formulation of different medications.

Synthesis Reference(s)

Synthesis, p. 662, 1974 DOI: 10.1055/s-1974-23397

InChI:InChI=1/C12H26/c1-5-6-7-8-9-10-11-12(2,3)4/h5-11H2,1-4H3

Upstream product

• 111-66-0 oct-1-ene 
• 630-19-3 pivalaldehyde 
• 94-36-0 dibenzoyl peroxide 
• 629-27-6 1-Iodooctane 
• 594-19-4 tert.-butyl lithium 
• 507-20-0 tertiary butyl chloride 
• 111-83-1 1-bromo-octane 
• 677-22-5 tert-butylmagnesium chloride 
• 463-11-6 1-Fluoro-octane 
• 106-99-0 buta-1,3-diene 
• 3386-35-4 1-octyl p-toluenesulfonate 
• 111-85-3 n-chlorooctane 
• 4911-58-4 5,5-dimethyl-hex-1-en-3-yne 
• 84718-85-4 (+/-)-2,2-dimethyl-3,4-decadiene 

Relevant articles and documents

Co-Catalyzed Cross-Coupling Reaction of Alkyl Fluorides with Alkyl Grignard Reagents

The cross-coupling reaction of unactivated alkyl fluorides with alkyl Grignard reagents by a CoCl2/LiI/1,3-pentadiene catalytic system is described. The present reaction smoothly cleaved C-F bonds under mild conditions and achieved alkyl-alkyl cross-coupling even when sterically hindered tertiary alkyl Grignard reagents were employed. Since alkyl fluorides are inert toward many reagents and catalytic intermediates, the use of the present reaction enables a new multistep synthetic route to construct carbon frameworks by combining conventional transformations.

Synthesis of mixed silylene-carbene chelate ligands from nheterocyclic silylcarbenes mediated by nickel

The NiII -mediated tautomerization of the N-heterocyclic hydrosilylcarbene L2Si(H)(CH2)NHC1, where L2 = CH(C=CH2)(CMe)(NAr)2, Ar = 2,6-iPr2C6H3 ; NHC = 3,4,5-trimethylimidazol-2-yliden-6-yl, leads to the first N-heterocyclic silylene (NHSi)-carbene (NHC) chelate ligand in the dibromo nickel(II) complex [L1SiD(CH2)(NHC)NiBr2]2 (L1 = CH(MeC=NAr)2). Reduction of 2 with KC8 in the presence of PMe3 as an auxiliary ligand afforded, depending on the reaction time, the N-heterocyclic silyl-NHC bromo NiII complex [L2Si(CH2)NHCNiBr(PMe3)] 3 and the unique Ni0 complex [h2(Si-H){L2Si(H)(CH2)NHC}Ni(PMe3)2] ,inf>4 featuring an agostic Si-H→!Ni bonding interaction. When 1,2-bis(dimethylphosphino)ethane (DMPE) was employed as an exogenous ligand, the first NHSi-NHC chelate-ligand-stabilized Ni0 complex [L1SiD(CH2)NHCNi(dmpe)] 5 could be isolated. Moreover, the dicarbonyl Ni0 complex 6, [L1SiD-(CH2)NHCNi(CO)2], is easily accessible by the reduction of 2 with K(BHEt3) under a CO atmosphere. The complexes were spectroscopically and structurally characterized. Furthermore, complex 2 can serve as an efficient precatalyst for Kumada-Corriu-type cross-coupling reactions.

Copper-Catalyzed Regioselective Hydroalkylation of 1,3-Dienes with Alkyl Fluorides and Grignard Reagents

Copper complexes generated in situ from CuCl2, alkyl Grignard reagents, and 1,3-dienes play important roles as catalytic active species for the 1,2-hydroalkylation of 1,3-dienes by alkyl fluorides through C-F bond cleavage. The alkyl group is introduced to an internal carbon atom of the 1,3-diene regioselectively, thus giving rise to the branched terminal alkene product. Making the switch: A copper-hydride species, generated by the treatment of a copper salt with alkyl Grignard reagents, catalyzes the 1,2-hydroalkylation of 1,3-dienes by alkyl fluorides and Grignard reagents. The alkyl group of the alkyl fluoride is selectively introduced to an internal carbon atom of the 1,3-diene and the Grignard reagent acts as hydride source to give the branched terminal alkene, even in the presence of alkenes and alkynes.

The cobalt-catalyzed cross-coupling reaction of alkyl halides with alkyl Grignard reagents: A new route to constructing quaternary carbon centers

The cross-coupling of alkyl (pseudo)halides with alkyl Grignard reagents is catalyzed efficiently by a cobalt(II) chloride-lithium iodide-1,3-diene catalytic system, which provides a new synthetic tool for constructing sp 3 carbon chains. This system is particularly useful for creating quaternary carbon centers via the use of tertiary alkyl Grignard reagents. Various functional groups including esters, amides and carbamates are well tolerated.

Co-catalyzed cross-coupling of alkyl halides with tertiary alkyl Grignard reagents using a 1,3-butadiene additive

The cobalt-catalyzed cross-coupling of alkyl (pseudo)halides with alkyl Grignard reagents in the presence of 1,3-butadiene as a ligand precursor and LiI is described. Sterically congested quaternary carbon centers could be constructed by using tertiary alkyl Grignard reagents. This reaction proceeds via an ionic mechanism with inversion of stereochemistry at the reacting site of the alkyl halide and is compatible with various functional groups. The use of both 1,3-butadiene and LiI was essential for achieving high yields and high selectivities.

Copper nanoparticle-catalyzed cross-coupling of alkyl halides with Grignard reagents

A cross-coupling reaction between alkyl bromides and chlorides and various Grignard reagents was carried out in the presence of commercially available copper or copper oxide nanoparticles as a catalyst and an alkyne additive. The catalytic system shows high activity, a broad scope, and good functional group tolerance.

Copper-catalyzed cross-coupling reaction of Grignard reagents with primary-alkyl halides: Remarkable effect of 1-phenylpropyne

(Chemical Equation Presented) A general get-together: The Cu-catalyzed cross-coupling reaction of primary-alkyl halides with primary-, secondary-, and tertiary-alkyl and phenyl Grignard reagents proceeds efficiently in THF under reflux in the presence of 1-phenylpropyne (see scheme). The reaction is also applicable to alkyl mesylates (OMs) and tosylates (OTs). The reactivities of alkyl-X with a Grignard reagent increase in the order X = Cl F OMs OTs Br.

Effect of solvent and temperature on the lithium-iodine exchange of primary alkyl iodides: Reaction of t-butyllithium with 1-iodooctane in heptane-ether mixtures

The reaction of 1-iodooctane, a representative primary alkyl iodide, with t-BuLi at 0 °C in solvent systems composed of heptane and four dialkyl ethers in various proportions has been investigated. Coupling and elimination are unavoidable side reactions that accompany lithium-iodine exchange when the reactions are conducted at 0 °C. The exchange reaction, which is slow in pure hydrocarbon solvent, is significantly facilitated by the presence of essentially catalytic quantities of an ether co-solvent. An optimal ether-heptane ratio for each of the ethers surveyed maximizes the extent of lithium-iodine exchange between 1-iodooctane and t -BuLi but in no case does the yield of octyllithium, assayed as octane, exceed ～90% when reactions were conduced at 0 °C. At lower temperatures, in a solvent system composed of heptane-MTBE (19:1 by volume), side reactions are suppressed and the yield of octyllithium approaches quantitative.

Cu-catalyzed alkylation of Grignard reagents: A new efficient procedure

The presence of NMP (4-9 equiv.) clearly improves the yield and the chemoselectivity of the Cu-catalyzed alkylation of organomagnesium reagents. Thus, secondary and tertiary alkylmagnesium chlorides were used successfully for the first time in such a reaction and ester, amide, nitrile or keto groups are tolerated. The procedure is cheap, environmentally friendly and very easy to carry out (1-3% Li2CuCl4 or CuCl, THF, 20°C). It is an interesting alternative to the classical alkylation of organocuprates reagents. (C) 2000 Published by Elsevier Science Ltd.

Novel tridentate diamino organomanganese(II) complexes as homogeneous catalysts in manganese(II)/copper(I) catalyzed carbon-carbon bond forming reactions

The new, paramagnetic arylmanganese(II) complex Li[MnCl2(NCN)] (2, NCN [C6H3(CH2NMe2)2-2,6] -) has been obtained in high yield from the reaction of MnCl2 and [Li(NCN)]2 in a 2:1 molar ratio. In THF solution, 2 is likely an ionic species [Li(THF)n] [MnCl2(NCN)] (molecular weight determination and conductivity measurements), while magnetic measurements indicate that a high spin d5 manganese(II) center is present. Subsequent reaction of 2 with RLi afforded [MnR(NCN)] (R=Me (3a), n-Bu (3b)). Complex 2, using CuCl as a co-catalyst, is an effective catalyst system for cross-coupling of Grignard reagents with alkyl bromides and the 1,4-addition of organomagnesium halides to α,β-unsaturated ketones. No further additives or co-solvents are necessary. For both reactions a dramatic decrease in reaction times is observed when compared to standard manganese/copper systems. Alkyl bromides with unsaturated or heteroatom functionalities can be cross-coupled. Also, excellent reactivity towards normally unreactive β,β-disubstituted ketones has been observed in the 1,4-addition reaction.