70380-66-4

Basic information

• Product Name: Benzene, 1-chloro-2-(dimethoxymethyl)-
• CAS NO: 70380-66-4
• Molecular Formula: C9H11ClO2
• Molecular Weight: 186.638
• Mol File: 70380-66-4.mol
• Article Data: 27

Chemical Properties

• CAS DataBase Reference: Benzene, 1-chloro-2-(dimethoxymethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1-chloro-2-(dimethoxymethyl)-(70380-66-4)
• EPA Substance Registry System: Benzene, 1-chloro-2-(dimethoxymethyl)-(70380-66-4)

Safety Data

• Hazardous Substances Data: 70380-66-4(Hazardous Substances Data)

Upstream product

• 89-98-5 2-chloro-benzaldehyde 
• 149-73-5 trimethyl orthoformate 
• 431-47-0 trifluoroacetic acid-methyl ester 
• 124-41-4 sodium methylate 
• 89712-45-8 N,N-dimethylformamide dimethyl sulfate adduct 
• 67-56-1 methanol 

Downstream Products

• 1125-88-8 benzaldehyde dimethyl acetal 
• 5406-38-2 2-(2-chlorophenyl)-1,3-dioxane 
• 2698-41-1 o-chlorobenzylidene malononitrile 
• 24393-43-9 ethyl 3-(2-chlorophenyl)-2-cyanoacrylate 
• 3533-10-6 3-(2-chlorophenyl)-2-cyanoprop-2-enamide 

Relevant articles and documents

Systematic Study of Regioselective Reductive Ring-Opening Reactions of 4,6- O-Halobenzylidene Acetals of Glucopyranosides

Reductive openings of cyclic acetals are widely used in modern synthetic organic chemistry for the regioselective introduction of protecting groups. A systematic study was performed on the applicability and efficacy of various hydride donor and protic or Lewis acid reagent combinations in the reductive ring opening of glucosidic 4,6-halobenzylidene acetals bearing an ortho-, meta-, and para-chloro- or -bromo substituent on the benzene ring. Most of the reagent combinations tested cleaved the 4,6-O-halobenzylidene acetal rings at O4 or O6 efficiently and with the expected regioselectivity. The LiAlH4-AlCl3 and the BH3·THF-TMSOTf combinations produced the 4-O-halobenzyl ether/6-OH products with complete regioselectivity and high yields. The use of Me3N·BH3-AlCl3 reagent system in toluene was also effective in cleaving the acetal ring at O6 but was accompanied by Al-chelation-assisted debenzylation side reactions. The NaCNBH3-HCl and the Et3SiH-BF3·Et2O combinations were highly effective in yielding the 6-halobenzyl ether/4-OH derivatives. Et3SiH, in combination with TfOH, produced the 6-O-ether/4-OH products in rapid reactions but also triggered silylation and reductive halobenzylation as secondary transformations. Reductive opening of the 1,3-dioxane ring of pyranosidic 4,6-O-halobenzylidene acetals by the proper reagent combination was found to be an efficient method for the regioselective introduction of versatile halobenzyl protecting groups onto the pyranose ring.

House bulb light-induced photochemical acetalization of carbonyl compounds catalyzed by Eosin Y

We have systematically studied the reactions of acetalization and found that high reaction efficiency can be achieved using cheap and readily available organic Eosin Y as catalyst. The reaction proceeds smoothly under house bulbs and shows excellent functional group tolerance. The substrates of the reaction system are compatible with aromatic aldehydes, aliphatic aldehydes, aromatic ketones, and cyclic ketones with high yields.

Silver-Catalyzed Olefination of Acetals and Ketals with Diazoesters to β-Alkoxyacrylates

The first silver-catalyzed reaction of acetals or ketals with diazoesters leading to trisubstituted or tetrasubstituted β-alkoxyacrylates is now reported. A broad range of acetals and ketals bearing different substituents is compatible with this protocol and thus provides an attractive approach for the synthesis of complex β-alkoxyacrylates. The power of this method was further demonstrated by the successful synthesis of picoxystrobin, which is one of the most popular agricultural fungicides commercialized by Dupont.