3740-05-4

Basic information

• Product Name: [(1Z)-3,3-dimethylbut-1-en-1-yl]benzene
• Synonyms: (Z)-1-Phenyl-3,3-dimethyl-1-butene
• CAS NO: 3740-05-4
• Molecular Formula: C₁₂H₁₆
• Molecular Weight: 160.2554
• Mol File: 3740-05-4.mol
• Article Data: 55

Chemical Properties

• Boiling Point: 223.3°C at 760 mmHg
• Flash Point: 82.4°C
• Density: 0.89g/cm³
• Vapor Pressure: 0.145mmHg at 25°C
• Refractive Index: 1.534
• CAS DataBase Reference: [(1Z)-3,3-dimethylbut-1-en-1-yl]benzene(CAS DataBase Reference)
• NIST Chemistry Reference: [(1Z)-3,3-dimethylbut-1-en-1-yl]benzene(3740-05-4)
• EPA Substance Registry System: [(1Z)-3,3-dimethylbut-1-en-1-yl]benzene(3740-05-4)

Safety Data

• Hazardous Substances Data: 3740-05-4(Hazardous Substances Data)

Upstream product

• 16636-96-7 di-tert-butylzinc 
• 536-74-3 phenylacetylene 
• 75-77-4 chloro-trimethyl-silane 
• 14371-19-8 cis-β-methoxystyrene 
• 594-19-4 tert.-butyl lithium 
• 16212-06-9 phenyl styryl sulfone 
• 38442-51-2 tert-butylmercury chloride 
• 677-22-5 tert-butylmagnesium chloride 
• 591-50-4 iodobenzene 
• 95835-72-6 (CH₃)3CCHCHB(OCH(CH₃)2)2 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 917-92-0 3,3-Dimethylbut-1-yne 
• 3677-81-4 diphenylboronchloride 
• 5123-17-1 bromodiphenylborane 

Downstream Products

• 3846-66-0 (E)-1-tert-butyl-2-phenylethene 
• 14198-16-4 1-Methylsulfinyl-3-phenyl-2-tert.butyl-propan 
• 3854-53-3 2,2-Dimethyl-3-benzyl-buten-⁽³⁾ 
• 131792-84-2 (E)-2,3,3-Trimethyl-1-phenyl-1-butene 
• 23586-64-3 (3,3-dimethylbut-1-ene-1,1-diyl)dibenzene 
• 181132-55-8 1-deuterio-3,3-dimethyl-1-phenyl-1-butene 
• 23586-62-1 (Z)-1-deuterio-3,3-dimethyl-1-phenyl-1-butene 
• 125315-95-9 (E)-(1-iodo-3,3-dimethylbut-1-en-1-yl)benzene 
• 125315-96-0 (Z)-(3,3-Dimethyl-1-iodo-1-butenyl)benzene 
• 1321204-48-1 5,5-dimethyl-3-phenyl-3-hexene-2-ol 
• 139556-26-6 (-)-(S)-3,3-dimethyl-1-phenyl-butan-1-ol 
• 1325730-32-2 (S)-2-(3,3-dimethyl-1-phenylbutyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 17314-92-0 (3,3-dimethylbutyl)benzene 

Relevant articles and documents

Photosensitized cis-trans Izomerization of β-Alkylstyrenes

Triplet sensitized izomerization of a series of β-alkylstyrenes has been investigated with the use of various sensitizers.Among the olefins employed β-t-butyl- and β-t-pentylstyrene were found to give remarkably high ratios of the cis-isomers ( >80percent

Facile and environmentally benign Zn-mediated cyclopropanation of electron-deficient 2-iodoethyl-substituted olefins via radical 3-exo-trig manner

An efficient, simple, cheap, and environmentally benign preparation of cyclopropanes via 3-exo-trig manner from various electron-deficient 2-iodoethyl-substituted olefins with zinc powder in a mixture of f-butyl alcohol and water was achieved.

An Amine-Assisted Ionic Monohydride Mechanism Enables Selective Alkyne cis-Semihydrogenation with Ethanol: From Elementary Steps to Catalysis

The selective synthesis of Z-alkenes in alkyne semihydrogenation relies on the reactivity difference of the catalysts toward the starting materials and the products. Here we report Z-selective semihydrogenation of alkynes with ethanol via a coordination-induced ionic monohydride mechanism. The EtOH-coordination-driven Cl- dissociation in a pincer Ir(III) hydridochloride complex (NCP)IrHCl (1) forms a cationic monohydride, [(NCP)IrH(EtOH)]+Cl-, that reacts selectively with alkynes over the corresponding Z-alkenes, thereby overcoming competing thermodynamically dominant alkene Z-E isomerization and overreduction. The challenge for establishing a catalytic cycle, however, lies in the alcoholysis step; the reaction of the alkyne insertion product (NCP)IrCl(vinyl) with EtOH does occur, but very slowly. Surprisingly, the alcoholysis does not proceed via direct protonolysis of the Ir-C(vinyl) bond. Instead, mechanistic data are consistent with an anion-involved alcoholysis pathway involving ionization of (NCP)IrCl(vinyl) via EtOH-for-Cl substitution and reversible protonation of Cl- ion with an Ir(III)-bound EtOH, followed by β-H elimination of the ethoxy ligand and C(vinyl)-H reductive elimination. The use of an amine is key to the monohydride mechanism by promoting the alcoholysis. The 1-amine-EtOH catalytic system exhibits an unprecedented level of substrate scope, generality, and compatibility, as demonstrated by Z-selective reduction of all alkyne classes, including challenging enynes and complex polyfunctionalized molecules. Comparison with a cationic monohydride complex bearing a noncoordinating BArF- ion elucidates the beneficial role of the Cl- ion in controlling the stereoselectivity, and comparison between 1-amine-EtOH and 1-NaOtBu-EtOH underscores the fact that this base variable, albeit in catalytic amounts, leads to different mechanisms and consequently different stereoselectivity.

Reductive Difunctionalization of Aryl Alkenes with Sodium Metal and Reduction-Resistant Alkoxy-Substituted Electrophiles

A general method for alkali-metal-promoted reductive difunctionalization of alkenes has been developed by means of reduction-resistant alkoxy-substituted electrophiles. A series of 1,2-diboration and 1,2-dicarbofunctionalization products can be synthesize

Heck Reaction of Electronically Diverse Tertiary Alkyl Halides

The efficient Pd-catalyzed Heck reaction of diverse tertiary alkyl halides with alkenes has been developed. Unactivated tertiary alkyl halides efficiently react at room temperature under visible light irradiation with no exogenous photosensitizers required. For activated tertiary alkyl halides, the same catalytic system works well without light. These methods offer a general access to electronically diverse alkenes possessing quaternary and functionalized tertiary allylic carbon centers. The substituents at these centers include alkyl-, carbalkoxy-, tosyl-, phosphonyl-, and boronate groups. It was also shown that the end-game mechanism of this transformation may vary depending on the type of the substrates used.