113647-42-0

Basic information

• Product Name: 3-Bromo-but-1-yne
• CAS NO: 113647-42-0
• Molecular Weight: 132.988
• Mol File: 113647-42-0.mol

Chemical Properties

• CAS DataBase Reference: 3-Bromo-but-1-yne(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromo-but-1-yne(113647-42-0)
• EPA Substance Registry System: 3-Bromo-but-1-yne(113647-42-0)

Safety Data

• Hazardous Substances Data: 113647-42-0(Hazardous Substances Data)

Upstream product

• 2028-63-9 but-3-yn-2-ol 

Downstream Products

• 52884-19-2 4-Mesityl-3-methyl-but-1-in-4-ol 
• 49770-21-0 Ethyl-(2-methyl-1-phenyl-but-3-ynyl)-amine 
• 49770-22-1 Isopropyl-(2-methyl-1-phenyl-but-3-ynyl)-amine 
• 49770-23-2 Isobutyl-(2-methyl-1-phenyl-but-3-ynyl)-amine 
• 1596-40-3 phenyl α-methylpropargyl ether 
• 13610-10-1 Buta-1,2-dienyl-phenylether 
• 13610-06-5 but-3-yn-2-yl(phenyl)sulfane 
• 13610-04-3 1,2-butadienyl phenyl sulfide 
• 1791-36-2 3-Phenylseleno-but-1-in 
• 77877-61-3 1-Phenylseleno-buta-1,2-dien 
• 52884-18-1 4-(p-Tolyl)-3-methyl-but-1-in-4-ol 
• 52884-20-5 4-(p-Nitrophenyl)-3-methyl-but-1-in-4-ol 
• 51207-10-4 3-ethyl-1-phenyl-2-propyn-1-ol 
• 52884-17-0 2-methyl-1-phenyl-2,3-butadien-1-ol 

Relevant articles and documents

Evidence for the Reactive Spin State of 1,4-Dehydrobenzenes

Two approaches have been used to investigate the spin state(s) of 1,4-dehydrobenzene produced in the solution thermolysis of diethynyl olefins.One method relies on the "spin correlation effect" which postulates a relationship between the spin state of a caged radical pair and the ratio of cage and escape reactions (C/E) which may occur in the pair.When the 2,3-di-n-propyl-1,4-dehydrobenzene biradical (4) abstracts hydrogen from 1,4-cyclohexadiene, a radical pair is generated.If a mixture of 1,4-cyclohexadiene-d0 and-d4 is employed, it is possible, by performing a VPC-MS analysis, to determined the C/E ratio leading from the radical pair to the reduced product, o-dipropylbenzene (10).When this method was applied to the reaction of (Z)-4,5-diethynyl-4-octene (3), C/E was found to be 0.6, independent of the concentration of 1,4-cyclohexadiene (between 0.1 and 10 M) in the chlorobenzene reaction solution.This result indicates the presence of the singlet state of 4 in the reaction of 3.Additional support for this analysis came from the reaction of 3,4-dimethyl-1,5-hexadiyn-3-ene (11) in hexachloroacetone solvent in a 1H NMR probe.The single polarized signal (emission) observed is attributed to the major product of the reaction, 1,4-dichloro-2,3-dimethylbenzene (12), obtained by chlorine abstraction from the solvent.The interpretation of this result indicates solvent trapping of the singlet state of the intermediate 2,3-dimethyl-1,4-dehydrobenzene, consistent with the chemical trapping study.These experimental approaches indicate that at least a substantial portion of the products formed from 1,4-dehydrobenzenes at elevated temperatures arise from the singlet state of the biradical.This suggests that either the singlet is the ground state or, if the triplet is lower in energy, the rate of intersystem crossing from the singlet must be 9 s-1 at 200 deg C.

Stereoselective thermal rearrangement of syn-7-(1,2-Butadienyl)-1-methylbicyclo[2.2.1]hept-2-ene [syn-7-(3-Methylallenyl)-1-methylnorbornene]

The synthesis and separate thermal rearrangements of (±)-(1R*,4S*,7S*)-7-[(R*)-1,2-butadienyl]-1- methylbicyclo[2.2.1]hept-2-ene (8a) and (±)-(1R*,4S*,7S*)-7-[(S*)-1,2-butadienyl]-1- methylbicyclo[2.2.1]hept-2-ene (8b) are described. Both 8a and 8b are shown to rearrange to (±)-cis-1-ethylidene-3a,4,5,7a-tetrahydro-6-methylindene (9) and (±)-cis-1-ethylindene-3a,4,5,7a-tetrahydro-3a-methylindene (10) with greater than 90% stereoselectivity. Epimer 8a gives predominantly (E)-9 and (Z)-10, whereas 8b gives predominantly (Z)-9 and (E)-10, results consistent with either a six-electron [σ2s + π2s + π2s] Cope or eight-electron [σ2s + π2s + (π2s + π2a)] augmented Cope process. Stereochemical assignments (8a vs 8b, (E)-9 vs (Z)-9, and (E)-10 vs (Z)-10) are based upon experiments in nuclear Overhauser effect (NOE) difference spectroscopy.

A mild method for the replacement of a hydroxyl group by halogen: 3. the dichotomous behavior of α-haloenamines towards allylic and propargylic alcohols

A study of the deoxyhalogenation of allylic and propargylic alcohols with tetramethyl-α-halo-enamines is reported. Primary allylic and primary and secondary propargylic alcohols gave the corresponding halides in high yields. Secondary allylic and propargylic alcohols yielded the corresponding secondary halides but the reaction also produced some rearranged primary halides (I > Br > Cl). The reactions with tertiary allylic and tertiary propargylic alcohols gave several products and was therefore of little synthetic value. However, the addition of triethylamine to the reaction mixture or the use of lithium alkoxide instead of alcohol brought about a major change of the course of the reaction which led to amides carrying an allyl or an allenyl group at C2. This was shown to result from a Claisen-Eschenmoser rearrangement of an intermediate α-allyloxy- or propargyloxy-enamine.

Synthesis of carbazoles based on gold-copper tandem catalysis

An efficient synthetic method for carbazoles has been developed employing diazo anilinoalkynes as substrates. Sequential activation of the orthogonal functional groups embedded in diazo anilinoalkyne substrates by tandem gold-copper catalysis leads to the formation of highly substituted carbazoles. Substrate scope reveals a broad tolerability toward the substitution on aryl groups.

Phase-Vanishing Methodology for Efficient Bromination, Alkylation, Epoxidation, and Oxidation Reactions of Organic Substrates

(Matrix presented) In cases where both reactants in a phase-vanishing reaction are less dense than the fluorous phase, an alternative to the U-tube method is to employ a solvent with greater density than the fluorous phase, such as 1,2-dibromoethane. This modification has been successfully applied to the methylation of a phenol derivative with dimethyl sulfate and to the m-CPBA-induced epoxidation of alkenes, N-oxide formation from nitrogen-containing compounds, and S-oxide or sulfone formation from organic sulfides.

A new method for the synthesis of plurisubstituted pyrroles

A versatile method for the synthesis of pyrroles is described using an intramolecular [3+2] cycloaddition reaction. This method allows the expedient preparation of 'plurisubstituted' compounds in which functionality is incorporated by choice, using appropriate readily available starting materials. Polycyclic pyrrole derivatives as well as 2-aryl monocyclic analogues are described. Several families of compounds are synthesized by sequential transformations. The method is designed to allow the creation of libraries with increased diversity of functionality by combinatorial or parallel synthesis.

An easy access to homopropargylic ethers

Chloromethyl ethers, obtained from alcohols, formaldehyde and HCl, react regioselectively, as shown previously in one case by L.Miginiac, with allenyl aluminium reagents derived from propargyl bromides and aluminium, to give homopropargyl ethers.No evidence for the presence of allenyl ethers was obtained in the cases described.This condensation is used to obtain a protected acetylenic synthon 1, required for the synthesis of an ecdysteroid analogue (1).

SYNTHESIS OF C27-SUBSTITUTED ECDYSTEROIDS, POTENTIAL TOOLS FOR BIOCHEMICAL STUDIES

A sequence of selective protection procedures is described, facilitating the efficient cleavage of the ecdysteroid side-chain, which can then be reconstructed; in this way, C-27 ether-linked analogues of ecdysteroids have been synthesized, one of which di