190974-78-8

Basic information

• Product Name: 4-(2,4-DIMETHYLPHENYL)-1-BUTENE
• Synonyms: 4-(2,4-DIMETHYLPHENYL)-1-BUTENE;1-But-3-enyl-2,4-dimethylbenzene
• CAS NO: 190974-78-8
• Molecular Formula: C12H16
• Molecular Weight: 160.26
• Mol File: 190974-78-8.mol

Chemical Properties

• Boiling Point: 225°C at 760 mmHg
• Flash Point: 83.5°C
• Appearance: /
• Density: 0.876g/cm³
• Vapor Pressure: 0.133mmHg at 25°C
• Refractive Index: 1.507
• CAS DataBase Reference: 4-(2,4-DIMETHYLPHENYL)-1-BUTENE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2,4-DIMETHYLPHENYL)-1-BUTENE(190974-78-8)
• EPA Substance Registry System: 4-(2,4-DIMETHYLPHENYL)-1-BUTENE(190974-78-8)

Safety Data

• Hazardous Substances Data: 190974-78-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H16/c1-4-5-6-12-8-7-10(2)9-11(12)3/h4,7-9H,1,5-6H2,2-3H3

Upstream product

• 824-55-5 2,4-dimethyl-benzyl chloride 
• 1730-25-2 allylmagnesium bromide 
• 15764-16-6 2,4-dimethylbenzaldehyde 
• 591-87-7 Allyl acetate 

Relevant articles and documents

Umpolung of Carbonyl Groups as Alkyl Organometallic Reagent Surrogates for Palladium-Catalyzed Allylic Alkylation

Palladium-catalyzed allylic alkylation of nonstabilized carbon nucleophiles is difficult and remains a major challenge. Reported here is a highly chemo- and regioselective direct palladium-catalyzed C-allylation of hydrazones, generated from carbonyls, as a source of umpolung unstabilized alkyl carbanions and surrogates of alkyl organometallic reagents. Contrary to classical allylation techniques, this umpolung reaction utilizes hydrazones prepared not only from aryl aldehydes but also from alkyl aldehydes and ketones as renewable feedstocks. This strategy complements the palladium-catalyzed coupling of unstabilized nucleophiles with allylic electrophiles by providing an efficient and selective catalytic alternative to the traditional use of highly reactive alkyl organometallic reagents.

Conjugative interaction in styrenes

Conjugative interactions of the carbon-carbon double bond are fundamental in organic chemistry. In this work, equilibria are established among conjugated and unconjugated isomers of two β-substituted styrenes, 1-phenylbut-1-ene and 1-phenyl-3-methylbut-1-ene, and one α,β-disubstituted styrene, 2-phenyl-5-methylhex-2-ene, over a range of temperatures (the van't Hoff method) in hexamethylphosphoric triamide and potassium tert-butoxide. From the trans styrenes of the first two sets, an enthalpy of conjugative interaction of phenyl vis-a-vis alkyl (ΔΔH(ConjInter/Alk)) = -2.5 ± 0.2 kcal/mol [-5.1 kcal/mol defined as phenyl vis-a-vis hydrogen (ΔΔH(ConjInter/H))] is observed, while the cis styrenes reveal an attenuated ΔΔH(ConjInter/Alk) of -1.1 kcal/mol (ΔΔH(ConjInter/H)) = -2.7 kcal/ mol). The α-methyl group in the third set also leads to a reduced conjugative interaction. Entropy plays an important role in determining positions of equilibrium. Free energies of conjugation are reported for several sterically hindered o-methyl-substituted styrenes.