232269-26-0

Basic information

• Product Name: 1,2-dibutoxy-1,2-dichloro-ethene
• Synonyms: 1,2-dibutoxy-1,2-dichloro-ethene
• CAS NO: 232269-26-0
• Molecular Weight: 241.158
• Mol File: 232269-26-0.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1,2-dibutoxy-1,2-dichloro-ethene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-dibutoxy-1,2-dichloro-ethene(232269-26-0)
• EPA Substance Registry System: 1,2-dibutoxy-1,2-dichloro-ethene(232269-26-0)

Safety Data

• Hazardous Substances Data: 232269-26-0(Hazardous Substances Data)

Downstream Products

• 1066-26-8 sodium acetylide 
• 2372-45-4 sodium butanolate 
• 106-98-9 1-butylene 
• 114620-78-9 butoxy-chloro-acetyl chloride 

Relevant articles and documents

Carbenes as substrates: Bimolecular fragmentation of alkoxychlorocarbenes

Fragmentation reactions of n-butoxychlorocarbene (9), isobutoxychlorocarbene (10), and benzyloxychlorocarbene (2) were studied by product analysis and by laser flash photolysis (LFP). The carbenes were generated photochemically from 3-alkyl-3-chlorodiazirines in (1) MeCN solution; (2) 5.77 M pyridine in MeCN; (3) 0.504 M tetrabutylammonium chloride (Bu4NCl) in MeCN; or (4) 5.77 M pyridine + 0.504 M Bu4NCl in MeCN. In MeCN, 9 gave mainly HCl-capture product, n-butyl dichloromethyl ether (45.1%), carbene dimer (9.8%), and azine (14.6%). Fragmentation products 1- butene (14,4%), 2-butyl chloride (6.0%), and 1-butyl chloride (10.2%) were limited. With added pyridine. HCl was scavenged, the dichloromethyl ether was suppressed, and 1-butene (42.1%), 2-butyl chloride (7.3%), and butyl chloride (24.1%) were dominant. With added Bu4NCl, 1-butyl chloride increased to 46.4%. With both pyridine and Bu4NCl, 1-butyl choride was 63% of the product, with 1-butene at 22.8%. A similar pattern was observed with carbene 10. Products in MeCN included isobutene (23%), 1- and 2-butene (8-9%), tert- butyl chloride (1, 7%), 2-butyl chloride (5.8%), isobutyl chloride (0.4%), isobutyl dichloromethyl ether (53%), and carbene dimer (8%). The isobutyl chloride fragmentation product increased from 0.4% in MeCN, to 7.3% with pyridine, to 32% with Bu4NCl, and to 38% with both addends. With 2, benzyl chloride increased from 83% in MeCN to 91% with added pyridine and Bu4NCl. The increase in chloride displacement products are attributed to bimolecular attacks of chloride ions at the α-carbon atoms of the carbenes, particularly 9 and 10. LFP kinetic studies show that the rate constants for fragmentation of these carbenes increase linearly with the concentration of added Bu4NCl in pyridine-MeCN. Second-order rate constant (k2) as a function of [Cl-] (M-1 s-1, 24 °C) for the fragmentations are 8.2 x 106 (9), 2.7 x 106 (10), and 2.2 x 106 (2). The decrease in k2 as R in ROCCI changes from n- butyl to isobutyl to benzyl is in accord with a S(N)2-like mechanism for the carbene fragmentations in which the benzyl case involves the competitive incursion of S(N)1-like fragmentation.