(Z)-1-Bromooctadec-9-ene

Base Information

• Chemical Name: (Z)-1-Bromooctadec-9-ene
• CAS No.: 6110-53-8
• Deprecated CAS: 1192430-70-8
• Molecular Formula: C₁₈H₃₅Br
• Molecular Weight: 331.38
• Hs Code.: 2903399090
• European Community (EC) Number: 228-074-1
• DSSTox Substance ID: DTXSID40884225
• Nikkaji Number: J227.302K
• Wikidata: Q82862936
• Mol file: 6110-53-8.mol

Synonyms:Oleyl bromide;(Z)-1-Bromooctadec-9-ene;6110-53-8;9-Octadecene, 1-bromo-, (9Z)-;(Z)-1-Bromo-9-octadecene;(Z)-9-Octadecen-1-yl bromide;9-Octadecene, 1-bromo-, (Z)-;EINECS 228-074-1;1-Bromo-cis-9-octadecene;Z-9-octadecenyl bromide;C18H35Br;SCHEMBL129710;(9Z)-1-Bromo-9-octadecene;C18-H35-Br;DTXSID40884225;Oleyl bromide, >=99% (GC);RRQWVJIFKFIUJU-KTKRTIGZSA-N;BP-29910;E84570;A868803

Chemical Property of (Z)-1-Bromooctadec-9-ene

Chemical Property:

• Vapor Pressure: 1.48E-05mmHg at 25°C
• Refractive Index: 1.472
• Boiling Point: 377.3 °C at 760 mmHg
• Flash Point: 179 °C
• PSA: 0.00000
• Density: 0.996 g/cm³
• LogP: 7.41880
• Storage Temp.: −20°C
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• XLogP3: 9.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 15
• Exact Mass: 330.19221
• Heavy Atom Count: 19
• Complexity: 175

Purity/Quality:

97% ^*data from raw suppliers

Oleyl Bromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCCCCC=CCCCCCCCCBr
• Isomeric SMILES: CCCCCCCC/C=C\CCCCCCCCBr
• Uses: Oleyl Bromide, can be used as the starting material in the synthesis of oleylphosphonates as potential inhibitors of diacylglycerol lipase (DAGL) and monoacylglycerol lipase (MAGL).

Technology Process of (Z)-1-Bromooctadec-9-ene

There total 12 articles about (Z)-1-Bromooctadec-9-ene 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: 100.0%

oleoyl alcohol (143-28-2,593-47-5,84286-21-5) → (Z)-1-bromo-9-octadecene (13044-38-7,62871-05-0,6110-53-8)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 0 - 20 ℃; for 0.5h;

DOI:10.1021/jm5020082

Reference yield: 100.0%

oleyl methanesulfonate (35709-09-2) → (Z)-1-bromo-9-octadecene (13044-38-7,62871-05-0,6110-53-8)

Guidance literature:

With lithium bromide; In acetone; at 20 ℃; for 20h; Reflux;

Reference yield: 100.0%

→ (Z)-1-bromo-9-octadecene (13044-38-7,62871-05-0,6110-53-8)

Guidance literature:

upstream raw materials:

oleoyl alcohol

oleyl methanesulfonate

hydrogen bromide

Methyl oleate

Downstream raw materials:

11-eicosenoic acid

trans-11-eicosenoic acid

cis-octadec-9-enethiol

N,N-dimethyl-N-oleylamine

Refernces

Synthesis and transfection efficiencies of new lipophilic polyamines

10.1021/jm0607101

The research focuses on the synthesis and evaluation of a series of lipophilic polyamines for DNA delivery and transfection efficiency. These polyamines, containing varying chain lengths and structures, were covalently attached to a 3,4-bis(oleyloxy)-benzyl motif and additionally linked via amide linkers for some derivatives. The study aimed to understand how the number and position of positive charges along the polyamine scaffold influence DNA delivery and transfection efficiency, competing with commercially available transfection reagents like Lipofectamine 2000. The experiments involved synthesizing the polyamine derivatives, evaluating their cytotoxicity in Chinese hamster ovary (CHO) cells, assessing their DNA delivery capabilities using AlexaFluor-488-labeled DNA, and measuring green fluorescent protein (GFP) expression after transfection with an eGFP DNA plasmid. Reactants used in the synthesis included 3,4-bis(oleyloxy)benzaldehyde, oleyl bromide, potassium carbonate, and various amines, while analyses were performed using techniques like NMR spectroscopy, high-resolution mass spectrometry, and flow cytometry to assess DNA uptake and GFP expression.

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