4Z,7Z,10Z,13Z-NONADECATETRAENYL BROMIDE

Base Information

• Chemical Name: 4Z,7Z,10Z,13Z-NONADECATETRAENYL BROMIDE
• CAS No.: 117567-53-0
• Molecular Formula: C₁₉H₃₁Br
• Molecular Weight: 339.359
• Mol file: 117567-53-0.mol

Synonyms:4Z,7Z,10Z,13Z-NONADECATETRAENYL BROMIDE

Chemical Property of 4Z,7Z,10Z,13Z-NONADECATETRAENYL BROMIDE

Chemical Property:

• PSA: 0.00000
• LogP: 7.13690
• Storage Temp.: −20°C

Purity/Quality:

95% ^*data from raw suppliers

Z-1-Bromononadeca-4,7,10,13-tetraene ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F+,Xn
• Statements: 12-19-20/21/22-36/37/38-40
• Safety Statements: 16-26-36

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4Z,7Z,10Z,13Z-NONADECATETRAENYL BROMIDE

There total 9 articles about 4Z,7Z,10Z,13Z-NONADECATETRAENYL BROMIDE 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: 76.0%

(Z,Z,Z,Z)-1-(tetrahydropyranyloxy)-4,7,10,13-nonadecatetraene (118207-24-2) → (Z,Z,Z,Z)-1-bromo-4,7,10,13-nonadecatetraene (117567-53-0)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In dichloromethane; for 10h; Ambient temperature;

DOI:10.1021/jo00263a049

Reference yield: 76.0%

2-[((4Z,7Z,10Z,13Z)-Nonadeca-4,7,10,13-tetraenyl)oxy]-tetrahydro-pyran (118207-24-2) → (Z,Z,Z,Z)-1-bromo-4,7,10,13-nonadecatetraene (117567-53-0)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In dichloromethane; 0 deg C to room temp. overnight;

DOI:10.1016/S0040-4039(00)95252-3

Reference yield:

1-bromooct-2-yne (18495-27-7) → (Z,Z,Z,Z)-1-bromo-4,7,10,13-nonadecatetraene (117567-53-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) EtMgBr, 2.) CuBr / 1.)THF, reflux, 1 h, 2.) THF, reflux, 12 h

2: 87 percent / H₂, ethylenediamine / P-2 nickel / ethanol / 4 h / 760 Torr

3: 97 percent / 50percent aq. TFA / CH₂Cl₂ / 3 h / 0 °C

4: 80 percent / PPh₃ / CH₂Cl₂ / 1 h / 0 °C

5: 91 percent / n-BuLi / hexane; tetrahydrofuran / 1.5 h / -78 - 0 °C

6: 1.) EtMgBr, 2.) CuBr / 1.) THF, reflux, 10 min, 2.) THF, reflux, 12 h

7: 65 percent / H₂ / P-2 nickel / ethanol / 5 h

8: 76 percent / CBr₄, PPh₃ / CH₂Cl₂ / 10 h / Ambient temperature

With n-butyllithium; carbon tetrabromide; ethylmagnesium bromide; hydrogen; ethylenediamine; triphenylphosphine; trifluoroacetic acid; copper(I) bromide; P-2 nickel; In tetrahydrofuran; ethanol; hexane; dichloromethane;

DOI:10.1021/jo00263a049

upstream raw materials:

2-[((4Z,7Z,10Z,13Z)-Nonadeca-4,7,10,13-tetraenyl)oxy]-tetrahydro-pyran

(Z,Z,Z,Z)-1-(tetrahydropyranyloxy)-4,7,10,13-nonadecatetraene

1-bromooct-2-yne

(3Z,6Z)-1-oxo-dodecadienal

Refernces

• 1、 Wagner, A.,Heitz, M.-P.,Mioskowski, C.. "DIRECT CONVERSION OF TETRAHYDROPYRANYLATED ALCOHOLS TO THE CORRESPONDING BROMIDES". . p. 557 - 558. Retrieved 2007/10/02.