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Cas Database

1119-51-3

1119-51-3

Identification

  • Product Name:5-Bromo-1-pentene

  • CAS Number: 1119-51-3

  • EINECS:214-281-4

  • Molecular Weight:149.03

  • Molecular Formula: C5H9Br

  • HS Code:29033036

  • Mol File:1119-51-3.mol

Synonyms:1-Bromo-4-pentene;4-Pentenyl bromide;1-Pentene, 5-bromo-;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi

  • Signal Word:Warning

  • Hazard Statement:H226 Flammable liquid and vapourH315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:TRC
  • Product Description:5-Bromo-1-pentene
  • Packaging:5g
  • Price:$ 50
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  • Manufacture/Brand:TCI Chemical
  • Product Description:5-Bromo-1-pentene >95.0%(GC)
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  • Manufacture/Brand:TCI Chemical
  • Product Description:5-Bromo-1-pentene >95.0%(GC)
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  • Manufacture/Brand:SynQuest Laboratories
  • Product Description:5-Bromopent-1-ene
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:5-Bromo-1-pentene 95%
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:5-Bromo-1-pentene 95%
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  • Manufacture/Brand:Oakwood
  • Product Description:5-Bromo-1-pentene 98%
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  • Manufacture/Brand:Medical Isotopes, Inc.
  • Product Description:5-Bromo-1-pentene
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  • Manufacture/Brand:Medical Isotopes, Inc.
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  • Manufacture/Brand:Matrix Scientific
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Relevant articles and documentsAll total 31 Articles be found

-

Gilbert,Nursten

, p. 527,533 (1972)

-

Cobalt-Mediated η5-Pentadienyl/Alkyne [5 + 2] Cycloaddition Reactions: Substitution Effects, Bicyclic Synthesis, and Photochemical η4-Cycloheptadiene Demetalation

Ylijoki, Kai E. O.,Kirk, Andrew D.,B?cklein, Sebastian,Witherell, Ross D.,Stryker, Jeffrey M.

, p. 3335 - 3357 (2015)

The preparation of seven-membered carbocycles via traditional organic synthesis is difficult, yet essential, due to the prevalence of these moieties in bioactive compounds. As we report, the Co-mediated pentadienyl/alkyne [5 + 2] cycloaddition reaction generates kinetically stable η2,η3-cycloheptadienyl complexes in high yield at room temperature, which isomerize to the thermodynamically preferred η5-cycloheptadienyl complexes upon heating at 60-70 °C. Here we describe an extended investigation of this reaction manifold, exploring substituent effects and extending the reaction to tandem cycloaddition/nucleophilic cyclizations, generating fused bicyclic compounds. We also describe a new high-yielding photolytic method for the decomplexation of organic cycloheptadienes from Co(I) complexes. Both C5Me5 (Cp?) and C5H5 (Cp) half-sandwich complexes are active in [5 + 2] cycloaddition with alkynes, with Cp? generally providing higher yields of cycloheptadienyl complexes. Cp cycloheptadienyl complexes, however, are resistant to thermal η2,η3 ' η5 isomerization. The reaction remains limited to open pentadienyl complexes incorporating substituents in the terminal (1 and 5) positions, except for the unsubstituted CpCo(η5-cycloheptadienyl)+ complex, which is modestly reactive. Incorporation of tethered latent nucleophiles allows cyclization onto the intermediate cycloheptadienyl cations, producing bicyclo[5.3.0]decadiene and bicyclo[5.4.0]undecadiene systems with complete diastereocontrol. A selection of intermediate complexes have been crystallographically characterized. Addition of tethered malonate nucleophiles occurs reversibly with equilibration to a thermodynamic elimination product, while enolate nucleophiles cyclize reliably under kinetic control. The resulting bicyclic products are decomplexed in high (>90%) yield by UV photolysis in the presence of allyl bromide to provide the organic bicyclic diene with complete retention of ring fusion geometry and without double-bond isomerization.

An original synthesis of highly ordered organosilica with a high content of thiol groups

Alauzun, Johan,Mehdi, Ahmad,Reye, Catherine,Corriu, Robert J. P.

, p. 347 - 349 (2006)

Well ordered bridged organosilica highly functionalised with disulfide groups were obtained by self-assembly of α,ω-bis(trimethoxysilyl) alkyldisulfide under hydrophilic conditions; the reduction of disulfide cores to SH groups gave rise to material having a high mercury ion adsorption capacity. The Royal Society of Chemistry 2006.

Phospho-Cope Rearrangement of Sodium Allylvinylphosphinate

Loewus, David I.

, p. 2292 - 2296 (1981)

Sodium allylvinylphosphinate (1) rearranges thermally to sodium hydrogen pent-4-enephosphonate (3) in virtually quantitative yield.The reaction probably constitutes a phospho-Cope rearrangement and presumably proceeds by way of the monomeric metaphosphonate 2 as a reactive intermediate.The half-time for the reaction is 4.67 h in water at 193.6+/- 1.0 deg C and 6.03 h in ethanol.By contrast, ethyl allylvinylphosphinate reacts in ethanol to give a mixture of compounds; although some of the product expected for a phospho-Cope is present in the mixture, the rearrangement is slower than that of the anion by a factor of at least 16.The mechanistic implications of these facts are discussed.

Dimethylamine as a Substrate in Hydroaminoalkylation Reactions

Bielefeld, Jens,Doye, Sven

, p. 15155 - 15158 (2017)

Transition-metal-catalyzed hydroaminoalkylations of alkenes have made great progress over the last decade and are heading to become a viable alternative to the industrial synthesis of amines through hydroformylation of alkenes and subsequent reductive amination. In the past, one major obstacle of this progress has been an inability to apply these reactions to the most important amines, methylamine and dimethylamine. Herein, we report the first successful use of dimethylamine in catalytic hydroaminoalkylations of alkenes with good yields. We also report applicability for a variety of alkenes to show the tolerance of the reaction towards different functional groups. Additionally, we present a catalytic dihydroaminoalkylation reaction using dimethylamine, which has never been reported before.

Simple and high yield access to octafunctional azido, amine and urea group bearing cubic spherosilicates

Sch?fer, Sandra,Kickelbick, Guido

, p. 221 - 226 (2017)

Spherosilicates and polyhedral oligomeric silsesquioxanes represent unique well-defined rigid building blocks for molecular and hybrid materials. Drawbacks in their synthesis are often low yields and the restricted presence of functional groups either based on incomplete transformation of all corners or the reactivity of the functional groups. Particularly amine-functionalization reveals some synthetic challenges. In this study we report the synthesis of a new class of octafunctionalized hydrogen bond forming spherosilicates via a facile route based on octabromo alkyl functionalized cubic spherosilicates. Four different alkyl chain lengths, namely C4, C5, C6 and C11, were realized starting from ω-alkenylbromides via hydrosilylation of Q8M8H. Using sodium azide in a mixture of acetonitrile:DMF = 10:1, the octaazide was obtained quantitatively and could be rapidly transformed in an octaamine cube via catalytic hydrogenation over Pd/C in absolute ethanol. The following reaction to hydrogen bond forming spherosilicates was performed in situ by adding propyl isocyanate. All transformations proceed quantitatively at the eight corners of the cube, which was evidenced by NMR spectroscopy and ESI-MS measurements. The Q8-target compound can be separated after each reaction step over simple chemical workup while no cage rearrangement was observed. The structures were confirmed using 1H, 13C, 29Si-NMR, FT-IR, elemental analysis and ESI-MS. The method opens a high yield route (overall isolated yield 83-88%) for structural building blocks in hybrid materials.

Further Studies of Substitution Reactions of Stannyl and Germyl Anionoids with Alkyl Bromides. Rearrangement of the 6-Hepten-2-yl Moiety

Kitching, William,Olszowy, Henry A.,Harvey, Karen

, p. 1893 - 1904 (1982)

The stereochemical outcomes of reactions of (trimethyltin)lithium, (dimethylphenyltin)lithium, (methyldiphenyltin)lithium, and (triphenyltin)lithium in tetrahydrofuran with trans- and cis-2-,3-, and 4-methylcyclohexyl bromides have been determined on the basis of 1H and 13C NMR spectroscopy.The (C6H5)3SnLi reactions proceed stereospecifically with inversion at carbon, while the (CH3)3SnLi reactions are nonstereospecific, as observed previously in some other systems. cis- and trans-2-methoxybromocyclohexanes and -cyclopentanes were also reacted with (CH3)3SnLi, and lowyields of (2-methoxycyclohexyl)- and (2-methoxycyclopentyl)trimethylstannanes were isolated.On the basis of 13C NMR spectra and deoxystannylation reactions , the former is largely ( 90percent) trans while the latter is exlusively trans.The pronounced stereochemical distinction between reactions of (CH3)3SnLi and (C6H5)3SnLi with cyclohexyl bromides is not observed in corresponding reactions of (CH3)3GeLi and (C6H5)3GeLi; both are nonspecific.Certain reactions of cyclopropylcarbinyl bromide and 6-bromo-1-hexene with R3SnLi and R3GeLi (R=CH3 or C6H5) were also studied.Rearranged product (allylcarbinyl) was observed in the reaction of cyclopropylcarbinyl bromide with (CH3)3SnLi, but cyclopentylmethyl products (from cyclization of any hex-5-enyl free radical) was not observed in any case.However, with the secondary 6-bromo-1-heptene all reagents studied (with the exception of (C6H5)3SnLi) afforded rearranged (2-methylcyclopentyl)methyl products, consistent with the intervention of the free radical, wich cyclizes rapidly.Some further estimates of the conformational A values of R3Ge and R3Sn are reported, and triphenyl derivatives have significantly larger values.

Synthesis of 1,10-dimethylbicyclo[8.8.8]hexacosane and 1,10- dihydroxybicyclo[8.8.8]hexacosane

Jones, Ian W.,Monguchi, Yasunari,Dawson, Alice,Carducci, Michael D.,Mash, Eugene A.

, p. 2841 - 2843 (2005)

(Chemical Equation Presented) 1,10-Dimethylbicyclo[8.8.8]hexacosane (1) and 1,10-dihydroxybicyclo[8.8.8]hexacosane (2) were prepared in 4% yield over seven steps and in 18% yield over three steps, respectively, starting from 1,10-cyclooctadecanedione. The identities and out,out conformations of these compounds were established by single-crystal X-ray analysis.

A Direct Synthesis of ω-Bromo-1-alkenes

Kraus, George A.,Landgrebe, Kevin

, p. 885 (1984)

-

-

Imoto et al.

, p. 314,316 (1963)

-

-

Smith,L.M. et al.

, p. 2361 - 2366 (1978)

-

The facile preparation of alkenyl metathesis synthons

Baughman, Travis W.,Sworen, John C.,Wagener, Kenneth B.

, p. 10943 - 10948 (2004)

We report synthetic methodology allowing the preparation of any length alkenyl halide from inexpensive starting reagents. Standard organic transformations were used to prepare straight chain α-olefin halides in excellent overall yields with no detectable olefin isomerization and full recovery of any unreacted starting material. Reported transformations can be used for the selective incorporation of pure α-olefin metathesis sites in highly functionalized molecules.

Novel synthetic method 5 -bromo -1 - pentene (by machine translation)

-

Paragraph 0021; 0031-0042, (2020/06/30)

N, N - dimethylformamide is used as a starting raw material, N, N-dimethylformamide is used as a solvent and is heated; 5 - bromo -1 - pentene crude product is obtained by reaction of hexamethylphosphoric acid triamine as a catalyst; crude product is washed twice with brine; and high-purity 1,5 - bromo -1 -1 - 5 - pentene is obtained by rectification 5 . To the method, the existing synthesis process and post-treatment are simplified, the reaction yield is improved, the production stability is improved, and the production cost is reduced. (by machine translation)

Formal Bromine Atom Transfer Radical Addition of Nonactivated Bromoalkanes Using Photoredox Gold Catalysis

Zidan, Montserrat,McCallum, Terry,Swann, Rowan,Barriault, Louis

supporting information, p. 8401 - 8406 (2020/11/03)

Organic transformations mediated by photoredox catalysis have been at the forefront of reaction discovery. Recently, it has been demonstrated that binuclear Au(I) bisphosphine complexes, such as [Au2(μ-dppm)2]X2, are capable of mediating electron transfer to nonactivated bromoalkanes for the generation of a variety of alkyl radicals. The transfer reactions of bromine, derived from nonactivated bromoalkanes, are largely unknown. Therefore, we propose that unique metal-based mechanistic pathways are at play, as this binuclear gold catalyst has been known to produce Au(III) Lewis acid intermediates. The scope and proposed mechanistic overview for the formal bromine atom transfer reaction of nonactivated bromoalkanes mediated by photoredox Au(I) catalysis is presented. The methodology presented afforded good yields and a broad scope which include examples using bromoalkanes and iodoarenes.

Process route upstream and downstream products

Process route

1,5-dibromo-pentane
111-24-0

1,5-dibromo-pentane

bromopentene
1119-51-3

bromopentene

Conditions
Conditions Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; In N,N-dimethyl-formamide; at 140 ℃; for 4h; Time; Temperature; Reagent/catalyst; Large scale;
80.1%
With potassium tert-butylate; In tetrahydrofuran; toluene; at 0 ℃; for 0.5h;
69%
With N,N,N,N,N,N-hexamethylphosphoric triamide; at 195 - 220 ℃;
60%
With N,N,N,N,N,N-hexamethylphosphoric triamide; at 195 - 230 ℃;
59%
With N,N,N,N,N,N-hexamethylphosphoric triamide; at 220 ℃; for 0.0833333h;
57%
With N,N,N,N,N,N-hexamethylphosphoric triamide; at 180 ℃;
54%
With N,N,N,N,N,N-hexamethylphosphoric triamide; at 195 - 200 ℃;
47%
With 18-crown-6 ether; potassium hydroxide; at 200 ℃; for 7h; under 270.027 Torr;
47%
In N,N,N,N,N,N-hexamethylphosphoric triamide; 195 deg C then 220 deg C;
46%
With N,N,N,N,N,N-hexamethylphosphoric triamide; at 205 ℃; for 0.0833333h;
44%
With N,N,N,N,N,N-hexamethylphosphoric triamide; at 195 - 220 ℃; for 0.0833333h;
42%
With 18-crown-6 ether; potassium tert-butylate; In diethyl ether; for 1h;
37%
With N,N,N,N,N,N-hexamethylphosphoric triamide; at 195 ℃;
With N,N,N,N,N,N-hexamethylphosphoric triamide; Heating;
With 18-crown-6 ether; potassium tert-butylate; In diethyl ether;
n-Pent-4-enyl alcohol
821-09-0

n-Pent-4-enyl alcohol

bromopentene
1119-51-3

bromopentene

Conditions
Conditions Yield
With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0 - 20 ℃; for 2.5h;
80%
With pyridine; bromine; triphenylphosphine; In benzene;
73%
With pyridine; phosphorus tribromide; 1.) -5 deg C, 30 min, 2.) RT, 2 h;
60%
n-Pent-4-enyl alcohol; With phosphorus tribromide; In diethyl ether; at -30 - 20 ℃; for 16.5h;
With sodium bromide; In diethyl ether; for 21h;
60%
With phosphorus tribromide; In n-heptane; at -10 ℃; for 2h;
55%
With phosphorus tribromide; In Petroleum ether; at -20 ℃;
46%
With pyridine; phosphorus tribromide; at -30 - -25 ℃; weniger gut bei Kuehlung mit Eis;
With pyridine; phosphorus tribromide;
With phosphorus tribromide;
With pyridine; phosphorus tribromide; at -5 ℃; for 0.25h;
With pyridine; phosphorus tribromide; at -30 - -25 ℃; for 1.16667h;
With pyridine; phosphorus tribromide; In diethyl ether;
With pyridine; triphenylphosphine dibromide 1:1 addition complex; In dichloromethane;
With bromine; triphenylphosphine; Yield given; 1.) CH2Cl2, 15 min., 2.) pyridine, ambient. temp., 1 h;
With pyridine; phosphorus tribromide; In Petroleum ether; at 0 ℃; for 1h;
With pyridine; phosphorus tribromide;
With N-Bromosuccinimide; triphenylphosphine; In N,N-dimethyl-formamide; at 20 ℃;
Multi-step reaction with 2 steps
1: KOH / diethyl ether / 2 h / 10 - 15 °C
2: LiBr / acetone / 1 h / Heating
With potassium hydroxide; lithium bromide; In diethyl ether; acetone;
With phosphorus tribromide; In diethyl ether; at -15 - 20 ℃; for 1.5h; Reflux; Inert atmosphere; Schlenk technique;
With carbon tetrabromide; triphenylphosphine; In dichloromethane;
Tetrahydrofurfuryl chloride
3003-84-7

Tetrahydrofurfuryl chloride

bromopentene
1119-51-3

bromopentene

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 1.) Na, 2.) H2O / diethyl ether
2: PBr3, pyridine
With pyridine; water; sodium; phosphorus tribromide; In diethyl ether;
Multi-step reaction with 2 steps
1: sodium-potassium; diethyl ether / und Zersetzen mit kaltem Wasser oder Eis
2: pyridine; phosphorus tribromoide / -30 - -25 °C / weniger gut bei Kuehlung mit Eis
With pyridine; potassium Sodium; diethyl ether; phosphorus tribromide;
2-(ω-bromopentylthio)-4,6-dimethylpyrimidine
15018-35-6

2-(ω-bromopentylthio)-4,6-dimethylpyrimidine

bromopentene
1119-51-3

bromopentene

2-bromo-4,6-dimethylpyrimidine hydrobromide

2-bromo-4,6-dimethylpyrimidine hydrobromide

2,2'-[1,5-pentanediylbis(thio)]bis(4,6-dimethylpyrimidine)
14961-48-9

2,2'-[1,5-pentanediylbis(thio)]bis(4,6-dimethylpyrimidine)

Conditions
Conditions Yield
at 170 - 200 ℃; under 15 Torr;
1.7 g
3.9 g
4.3 g
With sodium; at 170 - 200 ℃; under 15 Torr; 2.) CH3OH;
4.3 g
1.7 g
3.9 g
4-pentenyl acetate
1576-85-8

4-pentenyl acetate

bromopentene
1119-51-3

bromopentene

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 85 percent / LiAlH4 / diethyl ether / 3 h / 0 - 20 °C
2: 80 percent / carbon tetrabromide; triphenylphosphine / CH2Cl2 / 2.5 h / 0 - 20 °C
With lithium aluminium tetrahydride; carbon tetrabromide; triphenylphosphine; In diethyl ether; dichloromethane;
ethylene dibromide
106-93-4

ethylene dibromide

bromopentene
1119-51-3

bromopentene

Conditions
Conditions Yield
In diethyl ether;
1,4-dibromopentane
626-87-9

1,4-dibromopentane

bromopentene
1119-51-3

bromopentene

Conditions
Conditions Yield
With 2,3-Dimethylaniline; at 175 - 180 ℃;
toluene-4-sulfonic acid pent-4-enyl ester
19300-54-0

toluene-4-sulfonic acid pent-4-enyl ester

bromopentene
1119-51-3

bromopentene

Conditions
Conditions Yield
With lithium bromide; In acetone; for 1h; Yield given; Heating;
1,4-Pentadiene
591-93-5

1,4-Pentadiene

bromopentene
1119-51-3

bromopentene

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: 1) 9-BBN; 2) 6N NaOH, 30percent H2O2 / 1) 2h, THF; 2) 0 deg C; 3) 50 deg C
2: 46 percent / PBr3 / petroleum ether / -20 °C
With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide; phosphorus tribromide; In Petroleum ether;
Tetrahydrofurfuryl alcohol
97-99-4

Tetrahydrofurfuryl alcohol

bromopentene
1119-51-3

bromopentene

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: SOCl2, C5H5N2Na / diethyl ether
2: 1.) Triphenylphosphine, Br2 / 1.) CH2Cl2, 15 min., 2.) pyridine, ambient. temp., 1 h
With thionyl chloride; C5H5N2Na; bromine; triphenylphosphine; In diethyl ether;

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