(3Z,6Z)-1-broMonona-3,6-diene

Base Information

• Chemical Name: (3Z,6Z)-1-broMonona-3,6-diene
• CAS No.: 90121-03-2
• Molecular Formula: C9H15Br
• Molecular Weight: 203.122
• Mol file: 90121-03-2.mol

Synonyms:(Z,Z)-1-bromonona-3,6-dien;(Z,Z)-3,6-nonadienyl bromide;3,6-Nonadiene,1-bromo-,(Z,Z);

Chemical Property of (3Z,6Z)-1-broMonona-3,6-diene

Chemical Property:

• PSA: 0.00000
• LogP: 3.68390

Purity/Quality:

92-95%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3Z,6Z)-1-broMonona-3,6-diene

There total 8 articles about (3Z,6Z)-1-broMonona-3,6-diene 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: 96.0%

(Z,Z)-1-hydroxynona-3,6-diene (53046-97-2,167820-65-7,53250-56-9) → (3Z,6Z)-1-bromonona-3,6-diene (90121-03-2)

Guidance literature:

With pyridine; triphenylphosphine dibromide 1:1 addition complex; In acetonitrile; for 1h; Ambient temperature;

DOI:10.1080/00397919208021119

Reference yield:

1-bromo-pent-2-yne (16400-32-1) → (3Z,6Z)-1-bromonona-3,6-diene (90121-03-2)

Guidance literature:

Multi-step reaction with 3 steps

1: DBU, CuI, HMPT / tetrahydrofuran

2: H₂, (C₂H₅)N / Lindlar catalyst / tetrahydrofuran

3: CBr₄, P(C₆H₅)3 / CH₂Cl₂ / 0.17 h / 0 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; carbon tetrabromide; (C₂H₅)N; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; dichloromethane;

DOI:10.1002/ardp.19843170317

Reference yield:

nona-3,6-diyn-1-ol (57386-91-1) → (3Z,6Z)-1-bromonona-3,6-diene (90121-03-2)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂, (C₂H₅)N / Lindlar catalyst / tetrahydrofuran

2: CBr₄, P(C₆H₅)3 / CH₂Cl₂ / 0.17 h / 0 °C

With carbon tetrabromide; (C₂H₅)N; hydrogen; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; dichloromethane;

DOI:10.1002/ardp.19843170317

upstream raw materials:

(Z,Z)-1-hydroxynona-3,6-diene

1-bromo-pent-2-yne

nona-3,6-diyn-1-ol

(Z)-6-((tert-butyldiphenylsilyl)oxy)hex-3-en-1-ol

Downstream raw materials:

(3E,8Z,11Z)-3,8,11-tetradecatrien-1-yl acetate

all cis-5,8,11,14,17-eicosapentaenoic acid

LTC5

LTD5

Refernces

• 1、 Cabezas, Jorge A.. "A new and efficient synthesis of (3E,8Z,11Z)-tetradeca-3,8,11-trienyl acetate, the major sex pheromone component of the tomato leafminer Tuta absoluta". . p. 407 - 410. Retrieved 2019/01/08.
• 2、 Viala, Jacques,Sandri, Jacqueline. "Total Stereospecific Synthesis of all cis-5,8,11,14,17-Eicosapentaenoic Acid (EPA)". . p. 4897 - 4900. Retrieved 2007/10/02.