2-Pentene, 1-bromo-

Base Information

• Chemical Name: 2-Pentene, 1-bromo-
• CAS No.: 7348-71-2
• Molecular Formula: C5H9Br
• Molecular Weight: 149.03
• European Community (EC) Number: 625-896-6
• DSSTox Substance ID: DTXSID001032587
• Nikkaji Number: J97.477C,J1.662.950B
• Wikidata: Q76306584
• Mol file: 7348-71-2.mol

Synonyms:2-Pentene, 1-bromo-;7348-71-2;20599-27-3;(E)-1-bromopent-2-ene;1-Bromo-2-pentene, predominantly trans;1-BROMO-2-PENTENE;(E)-1-BROMO-2-PENTENE;(2E)-1-Bromopent-2-Ene;1-Bromo-2-pentene,predominantly trans;1-bromo-trans-2-pentene;1-bromopent-2-ene;E-1-Bromo-2-pentene;trans-1-bromo-pent-2-ene;(2E)-1-Bromo-2-pentene;SCHEMBL968386;SCHEMBL968388;FTBPZRNURKMEFD-ONEGZZNKSA-N;DTXSID001032587;AKOS015913654;EN300-99054;1-Bromo-2-pentene, predominantly trans, 95%;A848886

Chemical Property of 2-Pentene, 1-bromo-

Chemical Property:

• Melting Point: -106.7°C (estimate)
• Refractive Index: n20/D 1.4785(lit.)
• Boiling Point: 122oC(lit.)
• Flash Point: 73 °F
• PSA: 0.00000
• Density: 1.26 g/mL at 25oC(lit.)
• LogP: 2.34750
• Storage Temp.: 2-8°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 2
• Exact Mass: 147.98876
• Heavy Atom Count: 6
• Complexity: 39.2

Purity/Quality:

99% ^*data from raw suppliers

1-Bromo-2-pentene, predominantly trans 95% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: C
• Statements: 10-34
• Safety Statements: 16-26-27-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC=CCBr
• Isomeric SMILES: CC/C=C/CBr
• Uses: cis-1-Bromo-2-pentene was used in the synthesis of (+)-polyoxamic acid. It was also used in the preparation of pheromones.

Technology Process of 2-Pentene, 1-bromo-

There total 7 articles about 2-Pentene, 1-bromo- 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: 84.0%

(E)-2-penten-1-ol (1576-96-1) → (E)-1-bromo-2-pentene (7348-71-2)

Guidance literature:

With pyridine; phosphorus tribromide; In diethyl ether; at -10 ℃; for 4h;

DOI:10.1016/S0009-3084(00)00137-7

Reference yield:

(E)-4,4,4-trifluorobut-2-en-1-yl methanesulfonate (170924-54-6) + Methyl 4,5-dimethyl-3-formylpyrrole-2-carboxylate (33317-04-3) → methyl 3-formyl-4,5-dimethyl-1-(4,4,4-trifluoro-2-butenyl)pyrrole-2-carboxylate + (E)-1-bromo-2-pentene (7348-71-2)

Guidance literature:

Reference yield:

2-pent-2-ynyloxy-tetrahydro-pyran (6261-21-8) → (E)-1-bromo-2-pentene (7348-71-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / LiAlH₄ / tetrahydrofuran / 2 h / Heating

2: 78 percent / Br₃P / pentane / 0.5 h / 0 °C

With lithium aluminium tetrahydride; phosphorus tribromide; In tetrahydrofuran; pentane;

DOI:10.1016/S0040-4039(00)85115-1

upstream raw materials:

(+)-pent-1-en-3-ol

(E)-2-penten-1-ol

2-pent-2-ynyloxy-tetrahydro-pyran

(E)-4,4,4-trifluorobut-2-en-1-yl methanesulfonate

Downstream raw materials:

trans-N,N'-dimethyl-2,5-dioxo-8-undecene-4,6-disulfonanilide

6-<(E)-2-pentenyl>-2-hydroxy-2-cyclohexen-1-one

Triphenyl-((E)-1-trimethylsilanyl-hex-3-enyl)-phosphonium; bromide

(4S,5S)-4-Benzyloxymethyl-2,2-dimethyl-5-((E)-oct-5-en-2-ynyl)-[1,3]dioxolane

Refernces

• 1、 Bonney, Karl J.,Braddock, D. Christopher. "A unifying stereochemical analysis for the formation of halogenated C 15-acetogenin medium-ring ethers from laurencia species via intramolecular bromonium ion assisted epoxide ring-opening and experimental corroboration with a model epoxide". . p. 9574 - 9584. Retrieved 2012.
• 2、 Mupparapu, Nagaraju,Lin, Yu-Hsin Cindy,Kim, Tae Ho,Elshahawi, Sherif I.. "Regiospecific Synthesis of Calcium-Independent Daptomycin Antibiotics using a Chemoenzymatic Method". supporting information. p. 4176 - 4182. Retrieved 2021/02/01.