5-Bromo-1-pentene

Base Information

• Chemical Name: 5-Bromo-1-pentene
• CAS No.: 1119-51-3
• Molecular Formula: C5H9Br
• Molecular Weight: 149.03
• Hs Code.: 29033036
• European Community (EC) Number: 214-281-4
• DSSTox Substance ID: DTXSID7061512
• Nikkaji Number: J97.476E
• Wikidata: Q72448965
• Mol file: 1119-51-3.mol

Synonyms:5-Bromo-1-pentene;1119-51-3;5-Bromopent-1-ene;1-Pentene, 5-bromo-;1-Bromo-4-pentene;4-Pentenyl bromide;5-Bromopentene;5-bromo-pent-1-ene;EINECS 214-281-4;5-bromo-pentene;Pent-4-enyl bromide;SCHEMBL2925;5-Bromo-1-pentene, 95%;DTXSID7061512;GEO-00538;MFCD00000264;AKOS005146110;CS-W018483;GS-3547;AM20080066;B1474;FT-0600928;FT-0660355;EN300-79870;J-640298;J-660002;J-800302;Q-200532

Chemical Property of 5-Bromo-1-pentene

Chemical Property:

• Appearance/Colour: clear colourles to yellow liquid
• Vapor Pressure: 14.3mmHg at 25°C
• Melting Point: -106.7°C (estimate)
• Refractive Index: n20/D 1.463(lit.)
• Boiling Point: 126.2 °C at 760 mmHg
• Flash Point: 31 °C
• PSA: 0.00000
• Density: 1.248 g/cm³
• LogP: 2.34750
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Ethyl Acetate
• Water Solubility.: Immiscible with water.
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 147.98876
• Heavy Atom Count: 6
• Complexity: 32.9

Purity/Quality:

99% ^*data from raw suppliers

5-Bromo-1-pentene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-24/25-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Halogenated Aliphatics, Unsaturated
• Canonical SMILES: C=CCCCBr
• Uses: 5-Bromo-1-pentene is widely utilized in the stereoselective synthesis of 7alpha-(3-carboxypropyl) estradiol. It plays an important role as starting material in the synthesis of a variety of compounds including DL-histrionicotoxin and benzophenone containing fatty acids.

Technology Process of 5-Bromo-1-pentene

There total 18 articles about 5-Bromo-1-pentene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.1%

1,5-dibromo-pentane (111-24-0) → bromopentene (1119-51-3)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; In N,N-dimethyl-formamide; at 140 ℃; for 4h; Time; Temperature; Reagent/catalyst; Large scale;

Reference yield: 80.0%

n-Pent-4-enyl alcohol (821-09-0) → bromopentene (1119-51-3)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0 - 20 ℃; for 2.5h;

DOI:10.1016/j.tet.2004.09.021

Reference yield:

Tetrahydrofurfuryl chloride (3003-84-7) → bromopentene (1119-51-3)

Guidance literature:

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;

DOI:10.1021/ja00399a026

upstream raw materials:

n-Pent-4-enyl alcohol

1,2,5-tribromopentane

1,4-dibromopentane

1,5-dibromo-pentane

Downstream raw materials:

diethyl (4-pentenyl)malonate

2-(pent-4-enyl)-isoindoline-1,3-dione

5-fluoro-pent-1-ene

2-benzoylhept-6-enoic acid ethyl ester

Refernces

• 1、 Ylijoki, Kai E. O.,Kirk, Andrew D.,B?cklein, Sebastian,Witherell, Ross D.,Stryker, Jeffrey M.. "Cobalt-Mediated η5-Pentadienyl/Alkyne [5 + 2] Cycloaddition Reactions: Substitution Effects, Bicyclic Synthesis, and Photochemical η4-Cycloheptadiene Demetalation". . p. 3335 - 3357. Retrieved 2015.
• 2、 Loewus, David I.. "Phospho-Cope Rearrangement of Sodium Allylvinylphosphinate". . p. 2292 - 2296. Retrieved 1981.
• 3、 Sch?fer, Sandra,Kickelbick, Guido. "Simple and high yield access to octafunctional azido, amine and urea group bearing cubic spherosilicates". . p. 221 - 226. Retrieved 2017.
• 4、 Jones, Ian W.,Monguchi, Yasunari,Dawson, Alice,Carducci, Michael D.,Mash, Eugene A.. "Synthesis of 1,10-dimethylbicyclo[8.8.8]hexacosane and 1,10- dihydroxybicyclo[8.8.8]hexacosane". . p. 2841 - 2843. Retrieved 2005.
• 5、 Imoto et al.. "-". . p. 314,316. Retrieved 1963.
• 6、 Baughman, Travis W.,Sworen, John C.,Wagener, Kenneth B.. "The facile preparation of alkenyl metathesis synthons". . p. 10943 - 10948. Retrieved 2004.
• 7、 Zidan, Montserrat,McCallum, Terry,Swann, Rowan,Barriault, Louis. "Formal Bromine Atom Transfer Radical Addition of Nonactivated Bromoalkanes Using Photoredox Gold Catalysis". supporting information. p. 8401 - 8406. Retrieved 2020/11/03.