(1E,3E)-1,4-Dichloro-1,3-butadiene

Base Information

• Chemical Name: (1E,3E)-1,4-Dichloro-1,3-butadiene
• CAS No.: 3588-12-3
• Molecular Formula: C4H4Cl2
• Molecular Weight: 122.982
• Mol file: 3588-12-3.mol

Synonyms:trans,trans-1,4-dichlorobutadiene;trans,trans-1,4-Dichlor-butadien-(1,3);(E,E)-1,4-dichlorobutadiene;E,E-1,4-dichlorobutadiene;trans,trans-1,4-dichloro-1,3-butadiene;1t,4t-dichloro-buta-1,3-diene;(1E,3E)-1,4-Dichloro-buta-1,3-diene;

Chemical Property of (1E,3E)-1,4-Dichloro-1,3-butadiene

Chemical Property:

• Boiling Point: 60 °C (60 mmHg)
• PSA: 0.00000
• LogP: 2.49140

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1E,3E)-1,4-Dichloro-1,3-butadiene

There total 4 articles about (1E,3E)-1,4-Dichloro-1,3-butadiene 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:

1-chloro-1E,3-butadiene (16503-25-6) → 1,1-dichlorobuta-1,3-diene (6061-06-9) + 1,3,4-trichlorobutene (41601-58-5) + (E,E)-1,4-dichloro-1,3-butadiene (3588-12-3) + 1,1,4-trichloro-2-butene (41601-59-6,57808-36-3)

Guidance literature:

With 3-tert-butylbenzene-1,2-diol; chlorine; at -5 - 0 ℃; for 2.5h;

Reference yield:

cis-3,4-dichlorocyclobutene (2957-95-1) → cis,cis-1,4-dichloro-1,3-butadiene (3588-11-2) + cis,trans-1,4-dichloro-1,3-butadiene (3588-13-4) + (E,E)-1,4-dichloro-1,3-butadiene (3588-12-3)

Guidance literature:

Product distribution; Irradiation;

DOI:10.1021/ja00398a046

Reference yield:

(1Z,3Z)-1,4-bis(trimethylstannyl)-1,3-butadiene (112008-08-9) + (1E,3Z)-1,4-bis(trimethylstannyl)-1,3-butadiene (112008-09-0) + (1E,3E)-1,4-bis(trimethylstannyl)-1,3-butadiene (112008-10-3) → (trimethylstannyl)lithium (17946-71-3) + 1,4-dichloro-1,3-butadiene (2984-42-1,3588-11-2,3588-12-3,3588-13-4)

Guidance literature:

In tetrahydrofuran; Me3SnLi (prepd. from Me3SnCl and Li in THF) is added dropwise at 0°C to 1,4-dichloro-1,3-butadiene in THF. After being warmed to 25°C the mixt. is allowed to stir for 12 h.; removal of the solvent, the residue is extracted with pentaneand distilled, overall yield 60%, fractional distn. or GLPC;

upstream raw materials:

cis-3,4-dichlorocyclobutene

1-chloro-1E,3-butadiene

(1Z,3Z)-1,4-bis(trimethylstannyl)-1,3-butadiene

(1E,3Z)-1,4-bis(trimethylstannyl)-1,3-butadiene

Downstream raw materials:

2,3,4,5,2',3',4',5'-octaphenyl-1H,1'H-1,1'-buta-1,3-diene-1t,4t-diyl-bis-phosphole

Refernces

• 1、 Avagyan, S. P.,Airapetyan, R. Kh.,Kaplanyan, E. E.,Mkryan, G. M.. "CHEMISTRY OF DIENES AND THEIR DERIVATIVES. XIX. DIRECTION OF THE LOW-TEMPERATURE CHLORINATION OF 1-CHLORO-1,3-BUTADIENE (α-CHLOROBUTADIENE) IN THE PRESENCE OF AN INHIBITOR OF RADICAL REACTIONS". . p. 53 - 56. Retrieved 2007/10/02.
• 2、 Mao, Chung-Rei,Presser, Nathan,John, Lian-Shun,Moriarty, Robert M.,Gordon, Robert J.. "Production of Orbitally Forbidden Products in the IR-Laser-Induced Isomerization of cis-3,4-Dichlorocyclobutene". . p. 2105 - 2106. Retrieved 2007/10/02.