5312-73-2

Basic information

• Product Name: DICHLOROMETHYL N-BUTYL ETHER
• Synonyms: DICHLOROMETHYL N-BUTYL ETHER;N-BUTYL DICHLOROMETHYL ETHER;1-Dichloromethoxy-butane;Butyl Dichloromethyl Ether;Dichloromethyl Butyl Ether
• CAS NO: 5312-73-2
• Molecular Formula: C₅H₁₀Cl₂O
• Molecular Weight: 157.04
• Mol File: 5312-73-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 50 °C / 11mmHg
• Flash Point: 11.8oC
• Appearance: /
• Density: 1.11
• Vapor Pressure: 3.99mmHg at 25°C
• Refractive Index: 1.4360-1.4390
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: Acetone, Acetonitrile, Chloroform, DMSO (Slightly), Methanol (Slightly)
• Stability: Moisture Sensitive
• CAS DataBase Reference: DICHLOROMETHYL N-BUTYL ETHER(CAS DataBase Reference)
• NIST Chemistry Reference: DICHLOROMETHYL N-BUTYL ETHER(5312-73-2)
• EPA Substance Registry System: DICHLOROMETHYL N-BUTYL ETHER(5312-73-2)

Safety Data

• RIDADR: 1993
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 5312-73-2(Hazardous Substances Data)

Usage

General Description

DICHLOROMETHYL N-BUTYL ETHER is a clear, colorless liquid with a slightly sweet odor, commonly used as a solvent in various industrial applications. It is a volatile organic compound with the chemical formula C5H11Cl2O, and is known for its ability to dissolve a wide range of substances including paints, coatings, adhesives, and waxes. The chemical is also used as an intermediate in the production of other compounds, and has been utilized as a cleaning agent in some instances. However, it is important to handle DICHLOROMETHYL N-BUTYL ETHER with care, as it is considered harmful if swallowed, can cause skin and eye irritation, and may have adverse effects on the central nervous system if exposed to high concentrations. Therefore, proper safety precautions must be taken when working with this substance.

InChI:InChI=1/C5H10Cl2O/c1-2-3-4-8-5(6)7/h5H,2-4H2,1H3

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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.