75066-88-5

Basic information

• Product Name: Benzene, (3-methyl-1,3-butadienyl)-, (Z)-
• Synonyms: [(1Z)-3-methylbuta-1,3-dienyl]benzene;(Z)-(3-methyl-1,3-butadienyl)benzene;(Z)-3-Methyl-1-phenylbuta-1,3-diene;((Z)-3-Methyl-buta-1,3-dienyl)-benzene
• CAS NO: 75066-88-5
• Molecular Formula: C11H12
• Molecular Weight: 144.21300
• Mol File: 75066-88-5.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Benzene, (3-methyl-1,3-butadienyl)-, (Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, (3-methyl-1,3-butadienyl)-, (Z)-(75066-88-5)
• EPA Substance Registry System: Benzene, (3-methyl-1,3-butadienyl)-, (Z)-(75066-88-5)

Safety Data

• Hazardous Substances Data: 75066-88-5(Hazardous Substances Data)

Upstream product

• 15082-44-7 dilithium phenyl acetic acid 
• 19654-17-2 2-benzylthiobenzothiazole 
• 100-52-7 benzaldehyde 
• 847661-07-8 2,2,2-trifluoroethyl 2-methylprop-2-ene-1-sulfonate 
• 847661-08-9 S-(2,2,2-trifluoroethyl) 2-methylprop-2-ene-1-sulfothioate 
• 64275-72-5 (2-methylprop-2-en-1-yl)triphenylphosphonium bromide 
• 80674-39-1 threo-3-Hydroxy-4-methyl-2-phenyl-4-pentensaeure 
• 4303-59-7 2-methylallyltriphenylphosphonium chloride 
• 1530-49-0 methallyltributylphosphonium chloride 
• 78-85-3 2-methylpropenal 
• 67219-33-4 2-phenylmethanesulfonyl-benzothiazole 
• 1463-04-3 (3-methylbut-3-en-1-ynyl)benzene 

Relevant articles and documents

One-pot synthesis of 1-aryl-3-methyl-1,3-dienes using methallyl(trimethyl) silane and aldehydes and their low temperature (Z)→(E) isomerization induced by sulfur dioxide

2-Methylprop-2-ene-1-sulfonyl fluorides can be easily prepared via the ene reaction of methallylsilanes and SO2. In the presence of a base, aldehydes and 2-methylprop-2-ene-1-sulfonyl fluorides give 1,3-(E) and (Z)-dienes. Their (Z)→(E) isomerization by classical means fails or leads to their polymerization. It is shown that SO2 can isomerize 1-aryl-3-methyl-1,3-dienes at low temperature, without formation of sulfolenes (cheletropic addition/elimination). Preliminary mechanistic studies suggest that SO2 adds to 1,3-dienes forming 1,4-diradical intermediates that are responsible for the (Z)→(E) isomerizations.

Stereochemistry of direct olefin formation from carbonyl compounds and lithiated heterocyclic sulfones

The conditions for the title reaction were studied for the 2-benzothiazole and 2-pyridine series and for some examples in the 2-pyrimidine series.The olefin preparations were generally observed to be more efficient for 2-BT-sulfone systems.From the data of the hundred cases studied, it can be concluded that (E)-olefins are obtained: (i) from saturated BT-sulfones and aromatic aldehydes; and (ii) from benzylic BT-sulfones and branched saturated aldehydes (isobutyraldehyde, pivalaldehyde) or α,β-ethylenic or aromatic aldehydes. (Z)-olefins arise: (i) fom propargylic BT-sulfones and saturated or aromatic aldehydes; and (ii) from allylic or benzylic Pyr-sulfones and saturated aldehydes.Possible mechanisms for this new olefination procedure were examined. - heteroaromatic sulfones, organolithium derivatives, intramolecular ipso reactions, stereochemistry, elimination, olefination.

Additions of Carboxylic Acid Dianions to α,β-Unsaturated Carbonyl Compounds - Control of the 1,2-/1,4-Regioselectivity by Steric Substituent Effects

Dilithium carboxylic acid dianions 1 attack α,β-unsaturated aldehydes (2) 1,2-regiospecifically with formation of the unsaturated β-hydroxy carboxylic acids 3/4.Additionally, the addition of the phenylacetate dianion 1a can be conducted to the threo-isomer with high selectivity by reversible reaction. - α,β-Enones (8) add 1 irreversibly in 1,2- and 1,4-position.Depending on the substitution pattern, the whole range from pure 1,2- to pure 1,4-adduct is covered.The influence of the 1-counterion M and of the solvent is significant; the 1,4-portion increases with the complexing effect of M and with the Lewis-basicity of the solvent.