26653-38-3

Basic information

• Product Name: 1-(buta-1,2-dien-1-yl)-4-methylbenzene
• Synonyms: 1-(buta-1,2-dien-1-yl)-4-methylbenzene
• CAS NO: 26653-38-3
• Molecular Weight: 144.216
• Mol File: 26653-38-3.mol

Chemical Properties

• CAS DataBase Reference: 1-(buta-1,2-dien-1-yl)-4-methylbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(buta-1,2-dien-1-yl)-4-methylbenzene(26653-38-3)
• EPA Substance Registry System: 1-(buta-1,2-dien-1-yl)-4-methylbenzene(26653-38-3)

Safety Data

• Hazardous Substances Data: 26653-38-3(Hazardous Substances Data)

Upstream product

• 74-85-1 ethene 
• 766-97-2 4-n-methylphenylacetylene 
• 203121-40-8 (R)-4-p-tolylbut-3-yn-2-ol 
• 5720-05-8 4-methylphenylboronic acid 
• 21020-24-6 3-chloro-but-1-yne 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 594-02-5 1,1-diiodoethane 
• 79756-90-4 4-(4-methylphenyl)but-3-yn-2-ol 

Downstream Products

• 1380423-63-1 (E)-benzyl 4-p-tolylbut-3-en-2-ylcarbamate 

Relevant articles and documents

PALLADIUM-CATALYZED SYNTHESIS OF ALLENES.

Substituted allenes are selectively obtained in good yields from the reaction of Grignard reagents with propargylic or allenic halides in the presence of catalytic amounts of palladium chloride, triphenylphosphine and diisobutyl aluminium hydride, in tetr

Kinetics and Mechanism of Allene Racemization Catalyzed by a Gold N-Heterocyclic Carbene Complex

The kinetics of the racemization of 1,3-disubstituted allenes catalyzed by (IPr)AuOTf (IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidine) has been investigated. The rate of gold-catalyzed allene racemization obeyed the following second-order rate law: rate = krac[allene][Au]. An analysis of the rate of the gold-catalyzed racemization of 1-aryl-1,2-butadienes as a function of allene electron donor ability established moderate depletion of electron density on the C1 allenyl carbon atom in the rate-limiting transition state for racemization. Analysis of the temperature dependence of the rate of racemization of 1-(p-tolyl)-1,2-butadiene established the activation parameters ΔH∞ = 8.3 ± 1 kcal mol-1 and ΔS∞ = -28 ± 4 eu. These observations were in accord with a mechanism for allene racemization involving turnover-limiting, intermolecular allene exchange followed by rapid allene stereomutation.

Enantioselective, Stereodivergent Hydroazidation and Hydroamination of Allenes Catalyzed by Acyclic Diaminocarbene (ADC) Gold(I) Complexes

The gold-catalyzed enantioselective hydroazidation and hydroamination reactions of allenes are presented herein. ADC gold(I) catalysts derived from BINAM were critical for achieving high levels of enantioselectivity in both transformations. The sense of enantioinduction is reversed for the two different nucleophiles, allowing access to both enantiomers of the corresponding allylic amines using the same catalyst enantiomer. Chiral allylic azides and amines are obtained by enantioselective hydroazidation and hydroamination of allenes catalyzed by acyclic diaminocarbene gold(I) catalysts derived from BINAM. The sense of enantioinduction is reversed for the two different nucleophiles, allowing easy access to both enantiomers with a single catalyst enantiomer.

Gold(I)-catalyzed stereoconvergent, intermolecular enantioselective hydroamination of allenes

Gold and silver: A 1:2 mixture of [{(S)-1}(AuCl)2] and AgBF 4 catalyzes the enantioselective hydroamination of chiral, racemic 1,3-disubstituted allenes with N-unsubstituted carbamates to form N-allylic carbamates in good yield, with high regio- and diastereoselectivity, and up to 92% ee (see scheme, Cbz=benzyloxycarbonyl). Copyright

Ruthenium-catalyzed coupling of unactivated olefins with unactivated alkynes

A new ruthenium-catalyzed coupling reaction of an olefin with an alkyne is presented. The C-H bond of the olefin formally undergoes trans addition to the C-C triple bond to produce conjugated dienes.