128538-82-9

Basic information

• Product Name: 3,3-DICHLORO-2-METHOXYTETRAHYDROFURAN 98%
• Synonyms: 3,3-DICHLORO-2-METHOXYTETRAHYDROFURAN 98%;3,3-Dichloro-2-methoxytetrahydrofuran,98%
• CAS NO: 128538-82-9
• Molecular Formula: C5 H8 Cl2 O2
• Molecular Weight: 171.02
• Mol File: 128538-82-9.mol

Chemical Properties

• Boiling Point: 64°C/11mmHg
• Appearance: /
• CAS DataBase Reference: 3,3-DICHLORO-2-METHOXYTETRAHYDROFURAN 98%(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3-DICHLORO-2-METHOXYTETRAHYDROFURAN 98%(128538-82-9)
• EPA Substance Registry System: 3,3-DICHLORO-2-METHOXYTETRAHYDROFURAN 98%(128538-82-9)

Safety Data

• Hazardous Substances Data: 128538-82-9(Hazardous Substances Data)

Usage

Chemical Properties

Clear colourless to very slightly yellow liquid

Upstream product

• 67-56-1 methanol 
• 87459-26-5 2,2,4-trichlorobutanal 
• 75-64-9 tert-butylamine 
• 17557-41-4 (+/-)-2,3,3-Trichlorotetrahydrofuran 

Relevant articles and documents

SELECTIVE CLEAVAGE OF ASYMMETRIC ACETALS TO HEMIACETAL ACETATES. RING OPENING OF CHLORINATED 2-ALKOXYTETRAHYDROFURAN AND -TETRAHYDROPYRAN DERIVATIVES

Asymmetric acetals of α-chloro and α,α-dichloroaldehydes in acetic anhydride containing sulfuric acid afforded hemiacetal acetates at convenient rates at room temperature resp. at 127 deg C.The main product involved cleavage to the better stabilized α-alkoxycarbenium ion intermediate, with a typical ratio 87:13 for ethyl:methyl and 94:6 for propyl:2-chloroethyl.For 2-alkoxytetrahydrofuran and -tetrahydropyran substrates (alkyl = methyl, ethyl, 2-chloroethyl) ring cleavage was predominant (89-98percent).The kinetics were affected by several factors: the concentration of strong acid and of acetic anhydride (ionizing power of the medium), the ring size, nature and conformation of the 2-alkoxygroup and by a minor side-reaction that consumes acid by alkylation of its anion (OMe > OEt; eq.OMe > ax.OMe).

2,2,4-TRICHLOROBUTANAL: AN INVITATION TO THE SYNTHESIS OF HETEROCYCLIC COMPOUNDS

The title aldehyde (1) was obtained in 69percent isolated yield by chlorination of 4-chlorobutanol in the presence of dimethylformamide. 3,3-Dichloro-2-hydroxytetrahydrofuran (3a) or the 2-alkoxyderivatives 3b and 3c were produced by treating the hydrate 2a or the hemiacetals 2b and 2c resp. with base.With aqueous ammonia 1 rapidly formed the hemiaminal which then slowly afforded 3,3-dichloro-1-pyrroline (4).In a rapid reaction with primary alkylamines 1 was converted to N-alkyl-3,3-dichloro-2-hydroxypyrrolidines (5).The 2-hydroxyl group in 5 was reversibly exchanged in the presence of alcohols or amines. 5 were converted to N-alkyl-3,3-dichloro-1-pyrrolinium salts by an excess of trifluoroacetic acid.