14366-10-0

Basic information

• Product Name: 1-chlorobutane-2,3-dione 2-oxime
• Synonyms: 1-chlorobutane-2,3-dione 2-oxime;4-Chloro-3-hydroxyimino-2-butanone;Einecs 238-337-2
• CAS NO: 14366-10-0
• Molecular Formula: C₄H₆ClNO₂
• Molecular Weight: 135.54894
• EINECS: 238-337-2
• Mol File: 14366-10-0.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 235.1°Cat760mmHg
• Flash Point: 96°C
• Appearance: /
• Density: 1.29g/cm³
• Vapor Pressure: 0.0176mmHg at 25°C
• Refractive Index: 1.489
• CAS DataBase Reference: 1-chlorobutane-2,3-dione 2-oxime(CAS DataBase Reference)
• NIST Chemistry Reference: 1-chlorobutane-2,3-dione 2-oxime(14366-10-0)
• EPA Substance Registry System: 1-chlorobutane-2,3-dione 2-oxime(14366-10-0)

Safety Data

• Hazardous Substances Data: 14366-10-0(Hazardous Substances Data)

Usage

Derivative of

1-chloro-2-butanone

Functional group

Oxime

Pharmaceutical industry

Synthesis of various drugs

Agrochemicals

Production of agrochemicals

Research applications

Building block for the synthesis of other organic compounds

Other uses

a. Reagent in organic synthesis
b. Intermediate in the production of fine chemicals and flavor compounds

Toxicity

Poses health hazards and is toxic

Safety precautions

Proper safety measures should be taken when handling the compound

InChI:InChI=1/C4H6ClNO2/c1-3(7)4(2-5)6-8/h8H,2H2,1H3

Upstream product

• 78-94-4 methyl vinyl ketone 
• 6322-49-2 4-chloro-2-butanone 

Downstream Products

• 80322-63-0 3-acetyl-6-ethoxy-5,6-dihydro-4H-1,2-oxazine 
• 130223-62-0 12-acetyl-9-phenyl-2,10-dioxa-1,11-diazatricyclo-<7.4.0.0^3,7>trideca-4,11-diene 
• 69097-37-6 trans-3-acetyl-5-methyl-6-phenyl-5,6-dihydro-4H-1,2-oxazine 
• 69097-37-6 cis-3-acetyl-5-methyl-6-phenyl-5,6-dihydro-4H-1,2-oxazine 
• 105623-55-0 1-Chloro-butane-2,3-dione 2-[O-(1-methoxy-1-methyl-ethyl)-oxime] 
• 80322-65-2 3-acetyl-5,6-dihydro-6-methoxy-6-methyl-4H-1,2-oxazine 
• 105623-57-2 3-acetyl-4a,5,6,7-tetrahydro-4H-furo<3,2-e>-1,2-oxazine 
• 69097-36-5 3-acetyl-6-methyl-6-phenyl-5,6-dihydro-4H-1,2-oxazine 
• 14366-16-6 C₂₄H₂₀N₆O₁₀ 
• 14366-14-4 C₂₀H₁₅N₅O₈ 
• 14366-15-5 C₂₄H₂₂N₄O₆ 
• 5559-62-6 1-chloro-2,3-dioxo-butane 

Relevant articles and documents

Addition and Cycloaddition Reactions of the Electrophilic Vinyl Nitroso Compounds 3-Nitrosobut-3-en-2-one, 2-Nitrosopropenal, and Ethyl 2-Nitrosopropenoate

1-Chlorobutane-2,3-dione 2-oxime (2a) reacts with sodium carbonate and, in the presence of olefins, gives the oxazines (4) stereoselectively and in good yield. 3-Nitrosobut-3-en-2-one (1a) is postulated to be the intermediate in these reactions.Similar additions occur with 3-chloro-2-hydroxyiminopropanal (2b) and with ethyl bromopyruvate 2-oxime (3), although the oxazines are generally formed in lower yield.Competition experiments using pairs of olefins indicate that the intermediate (1a) adds preferentially to electron-rich olefins.The vinyl nitroso intermediates (1) act as electrophiles towards indole; the products are the corresponding 3-alkylindoles (11).Analogous reactions are observed with pyrrole, 1-methylpyrrole, 1,3-dimethoxybenzene, and NN-dimethylaniline; with 3-methylindole, addition takes place at the 3-position to give the cycloadducts (12). 3-Nitrosopent-3-en-2-one (19) has been generated from 4-chloropentane-2,3-dione 3-oxime.This vinyl nitroso intermediate also undergoes cycloaddition to olefins, in competition with a hydrogen shift from the terminal methyl group which leads to isomerisation to pent-2-ene-2,3-dione 3-oxime (20).