4-Bromotetrahydropyran

Base Information

• Chemical Name: 4-Bromotetrahydropyran
• CAS No.: 25637-16-5
• Molecular Formula: C5H9BrO
• Molecular Weight: 165.03
• Hs Code.: 29321900
• European Community (EC) Number: 687-292-9
• DSSTox Substance ID: DTXSID00537841
• Nikkaji Number: J3.543.919F
• Wikidata: Q72512776
• Mol file: 25637-16-5.mol

Synonyms:4-Bromotetrahydropyran;25637-16-5;4-BROMO-TETRAHYDROPYRAN;4-bromooxane;4-Bromotetrahydro-2H-pyran;4-bromo-tetrahydro-2H-pyran;MFCD07371501;2H-Pyran, 4-bromotetrahydro-;4-BROMOOXACYCLOHEXANE;4-bromanyloxane;monobromo tetrahydropyran;4-bromo-tetrahydro-pyran;SCHEMBL622798;DTXSID00537841;IVBVKTPDEWDNRW-UHFFFAOYSA-N;AKOS005256357;AM90079;CS-W003396;GS-4332;HY-W003396;PB24975;5-Hydroxy-1H-indole-2-carboxylic?acid;SY002700;B5600;EN300-154517;4-Bromooxacyclohexane, 4-Bromotetrahydro-2H-pyran;A817934;W-206965

Chemical Property of 4-Bromotetrahydropyran

Chemical Property:

• Vapor Pressure: 1.366mmHg at 25°C
• Refractive Index: 1.492
• Boiling Point: 177.986 °C at 760 mmHg
• Flash Point: 69.202 °C
• PSA: 9.23000
• Density: 1.475 g/cm³
• LogP: 1.56030
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 163.98368
• Heavy Atom Count: 7
• Complexity: 50

Purity/Quality:

98%, ^*data from raw suppliers

4-Bromo-tetrahydropyran ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COCCC1Br
• Uses: Reactant for:Nickel-catalyzed alkyl-alkyl Suzuki coupling reactions with boron reagentsPreparation of a selective small-molecule melanocortin-4 receptor agonist with efficacy in a pilot study of sexual dysfunction in humansPreparation of aliphatic hydrocarbons via nickel-catalyzed Suzuki cross-coupling with alkylboranesPreparation of anthranilic acids as antibacterial agents with human serum albumin binding affinityPreparation of antiatherogenic antioxidant di-tert-butyldihydrobenzofuranols via Grignard reactions with di-tert-butyl(hydroxy)benzaldehyde derivativesSynthesis of gephyrotoxin via the Schmidt reaction 4-Bromo-tetrahydropyran is a useful reactant in organic synthesis.

Technology Process of 4-Bromotetrahydropyran

There total 5 articles about 4-Bromotetrahydropyran 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: 88.0%

Tetrahydro-pyran-4-ol (2081-44-9) → 4-bromotetrahydro-2H-pyran (25637-16-5)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0 - 20 ℃; for 16h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.6b01592

Reference yield:

Tetrahydro-pyran-4-ol (2081-44-9) + hydrogen bromide (10035-10-6,12258-64-9) → 4-bromotetrahydro-2H-pyran (25637-16-5) + 1,3,5-tribromo-pentane (128813-74-1)

Guidance literature:

at 100 - 120 ℃;

DOI:10.1039/jr9490002749

Reference yield:

tetrahydro-2H-pyran-4-carboxylic acid (5337-03-1) → 4-bromotetrahydro-2H-pyran (25637-16-5)

Guidance literature:

With [bis(acetoxy)iodo]benzene; potassium bromide; at 25 ℃; Irradiation;

DOI:10.1021/acs.oprd.0c00130

upstream raw materials:

Tetrahydro-pyran-4-ol

formaldehyd

homoalylic alcohol

hydrogen bromide

Downstream raw materials:

1,3,5-tribromo-pentane

4-nitro-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole

1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole-4-amine

Refernces

• 1、 Kanazawa, Junichiro,Koyamada, Kenta,Miyamoto, Kazunori,Uchiyama, Masanobu,Watanabe, Ayumi. "Decarboxylative Bromination of Sterically Hindered Carboxylic Acids with Hypervalent Iodine(III) Reagents". supporting information. p. 1328 - 1334. Retrieved 2020/08/14.
• 2、 Strotman, Neil A.,Sommer, Stefan,Fu, Gregory C.. "Hiyama reactions of activated and unactivated secondary alkyl halides catalyzed by a nickel/norephedrine complex". . p. 3556 - 3558. Retrieved 2008/02/14.