66582-09-0

Basic information

• Product Name: Benzene, 1-(3,3-dimethyl-1-butynyl)-4-methoxy-
• CAS NO: 66582-09-0
• Molecular Formula: C13H16O
• Molecular Weight: 188.269
• Mol File: 66582-09-0.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: Benzene, 1-(3,3-dimethyl-1-butynyl)-4-methoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-(3,3-dimethyl-1-butynyl)-4-methoxy-(66582-09-0)
• EPA Substance Registry System: Benzene, 1-(3,3-dimethyl-1-butynyl)-4-methoxy-(66582-09-0)

Safety Data

• Hazardous Substances Data: 66582-09-0(Hazardous Substances Data)

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 917-92-0 3,3-Dimethylbut-1-yne 
• 507-20-0 tertiary butyl chloride 
• 768-60-5 4-methoxyphenylacetylen 
• 507-19-7 t-butyl bromide 
• 14630-42-3 (3,3-dimethyl-1-butynyl)trimethylsilane 
• 52418-50-5 4,4-dimethyl-2-pentynoic acid 
• 1950-68-1 4-methoxybenzenesulfonyl hydrazide 
• 33675-41-1 1-bromo-2-(4-methoxyphenyl)acetylene 
• 1539-54-4 4-(tert-butyl)-2, 6-dimethyl-1,4-dihydropyridine-3,5-dicarbonitrile 
• 100-07-2 4-methoxy-benzoyl chloride 
• 5720-07-0 4-methoxyphenylboronic acid 
• 115505-36-7 (3,3-dimethyl-1-butynyl)(phenyl)(tetrafluoroborato)-λ³-iodane 

Downstream Products

• 65853-51-2 3,3-dimethyl-1-(4-methoxyphenyl)butan-2-one 
• 85157-92-2 1-(4-methoxyphenyl)-3,3-dimethylbutan-1-one 
• 79958-53-5 (E)-1-(3,3-dimethylbut-1-en-1-yl)-4-methoxybenzene 
• 79958-52-4 1-[(1Z)-3,3-dimethylbut-1-en-1-yl]-4-methoxybenzene 
• 349421-55-2 N-(4-methoxyphenyl)-3,3-dimethylbutanamide 
• 924264-87-9 C₁₄H₁₈O₃ 
• 1286189-64-7 (E)-2-(4-methoxyphenyl)-4,4-dimethylpent-2-enoic acid 
• 1286189-76-1 1-(1-deuterio-3,3-dimethylbut-1-enyl)-4-methoxybenzene 
• 1283231-70-8 (E)-2-(1-(4-methoxyphenyl)-3,3-dimethylbut-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 214898-09-6 4-{3-[4-(3,3-dimethyl-but-1-ynyl)-phenoxy]-propyl}-imidazole-1-carboxylic acid tert-butyl ester 
• 184031-04-7 4-(3,3-dimethylbutynyl)phenol 
• 85157-90-0 (E)-1-Chlor-1-(4-methoxyphenyl)-3,3-dimethyl-1-buten 
• 85157-91-1 (Z)-1-Chlor-1-(4-methoxyphenyl)-3,3-dimethyl-1-buten 
• 104142-11-2 1,1-di(4-methoxyphenyl)-3,3-dimethyl-but-1-ene 

Relevant articles and documents

Fast "Wittig-Like" Reactions As a Consequence of the Inorganic Enamine Effect

(Chemical Equation Presented). The tungsten alkylidyne [CF3-ONO]W≡CC(CH3)3(THF)2 (3) {where CF3-ONO = (MeC6H3[C(CF3)2O])2N3-} supported by a trianionic pincer-type ligand demonstrates enhanced nucleophilicity in unusually fast "Wittig-like" reactions. Experiments are designed to provide support for an inorganic enamine effect that is the origin of the enhanced nucleophilicity. Treating complex 3 with various carbonyl-containing substrates provides tungsten-oxo-vinyl complexes upon oxygen atom transfer. The rates of reactivity of 3 are compared with the known alkylidyne (DIPP)3W≡CC(CH3)3 (DIPP = 2,6-diisopropylphenoxide). In all cases (except acetone), complex 3 exhibits significantly faster overall rates than (DIPP)3W≡CC(CH3)3. New oxo-vinyl complexes are characterized by NMR, combustion analysis and single crystal X-ray diffraction. Treating 3 with acid chlorides provides the tungsten oxo chloride species [CF3-ONO]W(O)Cl (4) and disubstituted alkynes. In the case of acetone the oxo-vinyl complex results in two rotational isomers 10syn and 10anti. The rate of isomerization was determined for the forward and reverse directions and was complimented with DFT calculations.

CsF-Mediated in Situ Desilylation of TMS-Alkynes for Sonogashira Reaction

A practical and mild set of conditions for the Sonogashira reaction utilizing CsF-mediated in situ TMS-alkyne desilylation followed by Sonogashira coupling has been developed for the synthesis of a variety of alkynyl benzenes and heteroarenes in good to excellent yields. This methodology demonstrates excellent functional group tolerance and simple purification, which allows large-scale industrial applications. This one-pot protocol enables a high-yielding Sonogashira coupling with volatile alkynes by avoiding challenging isolation of free alkynes.

Pd-Catalyzed decarboxylative alkynylation of alkynyl carboxylic acids with arylsulfonyl hydrazides via a desulfinative process

In the presence of a Pd(ii)/P-ligand catalytic system, decarboxylative alkynylation of alkynyl carboxylic acids and arylsulfonyl hydrazides by desulfinative coupling could provide aryl alkynes in satisfactory yields by either judiciously selecting palladium catalysts or modulating phosphine ligands under mild conditions. The reported coupling reactions are very practical as they do not require the protection of inert gas or oxygen and are tolerant to many functional groups.