1612-03-9

Basic information

• Product Name: (3-methylbut-1-yn-1-yl)benzene
• Synonyms: (3-Methylbut-1-yn-1-yl)benzene; 1-Phenyl-3-methyl-1-butyne; benzene, (3-methyl-1-butyn-1-yl)-; Benzene, (3-methyl-1-butynyl)-; Isopropyl-phenyl-acetylene
• CAS NO: 1612-03-9
• Molecular Formula: C₁₁H₁₂
• Molecular Weight: 144.213
• Mol File: 1612-03-9.mol

Chemical Properties

• Boiling Point: 215.2°C at 760 mmHg
• Flash Point: 80.1°C
• Density: 0.92g/cm³
• Vapor Pressure: 0.219mmHg at 25°C
• Refractive Index: 1.525
• CAS DataBase Reference: (3-methylbut-1-yn-1-yl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: (3-methylbut-1-yn-1-yl)benzene(1612-03-9)
• EPA Substance Registry System: (3-methylbut-1-yn-1-yl)benzene(1612-03-9)

Safety Data

• Hazardous Substances Data: 1612-03-9(Hazardous Substances Data)

Upstream product

• 3355-29-1 1,1-dimethyl-3-phenylprop-2-ynyl chloride 
• 2307-69-9 toluene-4-sulfonic acid isopropyl ester 
• 536-74-3 phenylacetylene 
• 102921-26-6 (1,2-dibromoethyl)benzene 
• 30615-19-1 isopropylmercury(II) chloride 
• 1719-19-3 2-Methyl-4-phenyl-3-butyn-2-ol 
• 33987-89-2 1-(isopropylsulfonyl)-2-phenylacetylene 
• 109431-70-1 4-phenylbut-3-yn-2-yl acetate 
• 628-71-7 1-Heptyne 
• 1776-66-5 triisopropylborane 
• 5324-64-1 2-(benzenesulfonyl)ethynylbenzene 
• 1539-32-8 4-isopropyl-2,6-dimethyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid diethyl ester 
• 1191-99-7 2,3-dihydro-2H-furan 
• 875-79-6 1,2-dimethylindole 

Downstream Products

• 21020-31-5 3-methyl-1-phenyl-1,2-butadiene 
• 54373-02-3 2-methyl-4-phenyl-2-hydroperoxy-3-butyne 
• 849667-40-9 2-isopropyl-3-phenyl-cycloprop-2-enecarboxylic acid ethyl ester 
• 1283231-63-9 (Z)-4,4,5,5-tetramethyl-2-(3-methyl-1-phenylbut-1-en-2-yl)-1,3,2-dioxaborolane 
• 1377578-89-6 2-isopropyl-2-phenyl-1H-pyrrolo[3,2-c]pyridine 
• 1377578-72-7 2-isopropyl-3-phenyl-1H-pyrrolo[3,2-c]pyridine 
• 1351520-77-8 (Z)-2-isopropyl-1-phenyl-1-hexene 
• 1351520-81-4 (E)-2-isopropyl-1-phenyl-1-hexene 
• 1283231-73-1 (Z)-4,4,5,5-tetramethyl-2-(3-methyl-1-phenylbut-1-en-1-yl)-1,3,2-dioxaborolane 

Relevant articles and documents

Enantioselective Three-Component Coupling of Heteroarenes, Cycloalkenes and Propargylic Acetates

Asymmetric coupling proceeds efficiently between propargylic acetates, cycloalkenes and electron-rich heteroarenes including indoles, pyrroles, activated furans and thiophenes. 2,3-Disubstituted tetrahydrofurans and pyrrolidines are produced in trans conf

An Enzymatic Platform for Primary Amination of 1-Aryl-2-alkyl Alkynes

Propargyl amines are versatile synthetic intermediates with numerous applications in the pharmaceutical industry. An attractive strategy for efficient preparation of these compounds is nitrene propargylic C(sp3)-H insertion. However, achieving this reacti

Z-Selective Synthesis of α-Sulfanyl Carbonyl Compounds from Internal Alkynes and Thiols via Photoredox Catalysis

A synthetically useful Z-selective cascade formal thiyl radical addition, 1,3-double bond isomerization, oxygen trapping reaction, can be promoted by Eosin B under visible light, leading to the construction of 2-aryl- and alkylthio enone derivatives in good yields. An accurate study on the reactivity of different thiols and the screening of the reaction conditions, allowed us to extend this reaction to a large number of substrates, showing a good functional groups tolerance while highlighting the limitations of this procedure. Background experiments and mechanistic studies were also. performed to rationalize this cascade process. The usefulness of this methodology was finally demonstrated via the transformation of a series of α-sulfanyl-enone adducts through selected oxidation reactions, stereoselective synthesis of cyclopropyl ketones, indanones, and pyrazole compounds. (Figure presented.).

Visible-light-mediated alkylation of 4-alkyl-1,4-dihydropyridines with alkenyl sulfones

Herein we report a mild, general protocol for visible-light-mediated alkylation of 4-alkyl-1,4-dihydropyridines with alkenyl sulfones. The protocol permits efficient functionalization of sulfones with a broad range of cyclic and acyclic secondary and tert

Nickel-Catalyzed Sonogashira Coupling Reactions of Nonactivated Alkyl Chlorides under Mild Conditions

The two nickel chlorides1and2with [P,S] and [P,Se] bidentate ligands, respectively, were synthesized and used as catalysts for Sonogashira coupling reaction. Both1and2are efficient catalysts for Sonogashira C(sp3)-C(sp) coupling reactions. Comp

Phosphorus(III)-Mediated, Tandem Deoxygenative Geminal Chlorofluorination of 1,2-Diketones

Tetrasubstituted carbon containing two different halogen substituents was constructed in a single-step operation by utilizing the carbene-like reactivity of dioxaphospholene through the tandem reaction of electrophilic and nucleophilic halogenating reagents. It was crucial to devise non-dealkylatable phosphoramidite, which enabled the efficient formation of geminal chlorofluorides from various 1,2-diketones with (PhSO2)2NF and n-Bu4NCl. In addition, selective functionalization of the chlorine substituent was demonstrated, and the absence of halogen scrambling was confirmed.

Iron-Catalyzed Cross-Coupling of Alkynyl and Styrenyl Chlorides with Alkyl Grignard Reagents in Batch and Flow

Transition-metal-catalyzed cross-coupling chemistry can be regarded as one of the most powerful protocols to construct carbon–carbon bonds. While the field is still dominated by palladium catalysis, there is an increasing interest to develop protocols that utilize cheaper and more sustainable metal sources. Herein, we report a selective, practical, and fast iron-based cross-coupling reaction that enables the formation of Csp?Csp3 and Csp2?Csp3 bonds. In a telescoped flow process, the reaction can be combined with the Grignard reagent synthesis. Moreover, flow allows the use of a supporting ligand to be avoided without eroding the reaction selectivity.

RETRACTED ARTICLE: Copper-Catalyzed Decarboxylative C(sp2)-C(sp3) and C(sp)-C(sp3) Coupling of Substituted Cinnamic Acids and 3-Phenyl Propiolic Acid with N-Tosyl Oxaziridines

A mild and efficient strategy for decarboxylative C(sp2)-C(sp3) and C(sp)-C(sp3) coupling of α,β-unsaturated carboxylic acids such as substituted cinnamic acids and 3-phenyl propiolic acid with N-Tosyl oxaziridines was developed. The corresponding products were achieved in moderate to good yields with excellent stereoselectivity. Base-free and oxidant-free conditions allow good functional group tolerance. Radical inhibitors such as TEMPO and BHT completely suppressed the reactions suggesting a radical mechanism was involved. This study is supposed to broaden the frontier of oxaziridines' chemistry and to open up a novel cascade for alkylating reagents.

Trimethylsilyl-Protected Alkynes as Selective Cross-Coupling Partners in Titanium-Catalyzed [2+2+1] Pyrrole Synthesis

Trimethylsilyl (TMS)-protected alkynes served as selective alkyne cross-coupling partners in titanium-catalyzed [2+2+1] pyrrole synthesis. Reactions of TMS-protected alkynes with internal alkynes and azobenzene under the catalysis of titanium imido comple

Application of Hantzsch Ester and Meyer Nitrile in Radical Alkynylation Reactions

The first example of constructing a Csp3-Csp bond with substituted Hantzsch ester and Meyer nitrile is reported. When benziodoxole-activated alkyne was applied as the alkynyl donor, products containing Csp3-Csp bonds involving primary, secondary, and tertiary carbon centers were achieved in up to 97% yields. K2S2O8 was the optimum radical initiator in this reaction.