16714-77-5

Basic information

• Product Name: 1,3-dichlorobutan-2-one
• Synonyms: 1,3-dichlorobutan-2-one;1,3-Dichloro-2-butanone;Einecs 240-767-0
• CAS NO: 16714-77-5
• Molecular Formula: C₄H₆Cl₂O
• Molecular Weight: 140.99584
• EINECS: 240-767-0
• Mol File: 16714-77-5.mol

Chemical Properties

• Boiling Point: 189.51°C (rough estimate)
• Flash Point: 59°C
• Appearance: /
• Density: 1.3116
• Vapor Pressure: 1.78mmHg at 25°C
• Refractive Index: 1.4686 (estimate)
• CAS DataBase Reference: 1,3-dichlorobutan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-dichlorobutan-2-one(16714-77-5)
• EPA Substance Registry System: 1,3-dichlorobutan-2-one(16714-77-5)

Safety Data

• Hazardous Substances Data: 16714-77-5(Hazardous Substances Data)

Usage

Physical state

Colorless liquid

Odor

Pungent

Usage

Reagent in organic synthesis

Application

Production of various chemical compounds

Application

Solvent in industrial processes

Application

Intermediate in manufacturing of pharmaceuticals and agrochemicals

Hazard

Potentially toxic compound

Safety concern

Causes irritation to skin, eyes, and respiratory system upon exposure

Precaution

Handle with caution

InChI:InChI=1/C4H6Cl2O/c1-3(6)4(7)2-5/h3H,2H2,1H3

Upstream product

• 56-23-5 tetrachloromethane 
• 116496-45-8 1,3-dichloro-2-chloromethyl-but-1-ene 
• 69295-21-2 3-Chlor-2-chlormethyl-but-1-en 
• 78-93-3 butanone 
• 51107-31-4 2-Chloro-2-(1-chloroethyl)oxirane 
• 187399-76-4 2-Chloro-2-(chloromethyl)-3-methyloxirane 
• 80212-73-3 (Z)-2-Chlor-2-chlormethyl-3-methyloxiran 
• 80212-73-3 (E)-2-Chlor-2-chlormethyl-3-methyloxiran 
• 67-56-1 methanol 
• 593-71-5 Chloroiodomethane 
• 535-13-7 2-chloro-propanoic acid, ethyl ester 
• 7647-01-0 hydrogenchloride 
• 64-19-7 acetic acid 
• 7732-18-5 water 

Downstream Products

• 503-64-0 (Z)-but-2-enoic acid 
• 107-93-7 (E)-but-2-enoic acid 
• 598-78-7 (R,S)-2-chloropropionic acid 
• 3724-65-0 2-butenoic acid 
• 4358-59-2 (Z)-methyl but-2-enoate 
• 623-43-8 crotonic acid methyl ester 
• 6342-57-0 ethylglyoxal dimethylacetal 
• 80-62-6 methacrylic acid methyl ester 
• 3136-17-2 Methyl β-methoxybutyrate 

Relevant articles and documents

Cu(OTf)2-catalyzed α-halogenation of ketones with 1,3-dichloro-5,5'-dimethylhydantoin and N-bromosuccinimide

Copper(II) triflate catalyses efficiently the α-halogentaion of aryl or alkyl ketones with l.3-diehloro-5.5'-dimethylhydantoin and N-bromosuccinimde to give the corresponding α,α-dichloroketones and α-bromoketones in high yield with excellent product selectivity.

Conformational analysis, Part 32. NMR, solvation and theoretical investigation of conformational isomerism in 3-fluorobutan-2-one and 3,3-difluorobutan-2-one

The solvent and temperature dependence of the 1H and 13C NMR spectra of 3-fluorobutan-2-one (FB) and 3,3-difluorobutan-2-one (DFB) are reported and the 4JHF, 1JCF and 2JCF couplings analysed using ab initio calculations and solvation theory. The solvent dependence of the IR spectra (carbonyl band) was also measured. In FB, ab initio theory at the 6-31G**/MP2 level gives only two energy minima for the cis (F-C-C=O 22°) and trans (F-C-C=O 178°) rotamers. The gauche rotamer was not a minimum in the energy surface. Assuming only the cis and trans forms, the observed couplings when analysed by solvation theory lead to the energy difference (Ecis - Etrans) between the cis and trans rotamers of 3.7 kcal mol-1 in the vapour phase, decreasing to 2.5 kcal mol-1 in CCl4 and to 0.1 kcal mol-1 in DMSO. In all solvents used the trans rotamer is more stable than the cis. The vapour state energy difference compares very well with that calculated [3.67 kcal mol-1 including a zero-point energy correction (ZPE)]. In DFB ab initio calculations at this level and also at (6-311G**/MP2 and ZPE) gave only one minimum in the potential energy surface corresponding to the cis rotamer (C-C-C=O 0°). The 1H and 13C NMR data, 4JHF, 1JCF and 2JCF couplings do not change with solvent confirming that there is only one rotamer in solution for DFB, in agreement with the ab initio calculations.

A Simple and Unambiguous Synthesis of α,α- and α,α'-Dihalogeno Ketones

A convenient method for the unambiguous preparation of α,α'-dihalogeno ketones 3 from in situ-generated chloromethyllithium and α-chloro or α-bromo carboxylic acid esters 1 at -78 deg C, is described.The unambiguous prparation of α,α-dihalogeno ketones 7 by using in situ-generated dihalogenomethyllithium and carboxylic acid esters 5 at -78 deg C is also reported.

An Easy Synthesis of α-Chloro-α'-bromo or α,α'-Dichloro Ketones

The reaction of α-chloro or α-bromo carboxylic acid esters (1) with in situ-generated chloromethyllithium (1: 1.5 molar ratio) at -78 deg C in the presence of lithium bromide leads, after hydrolysis, to the corresponding α,α'-dichloro or α-chloro-α'-bromo ketones (2), respectively.

Chlorination of Aliphatic Ketones in Methanol

The chlorination of aliphatic ketones in methanol has been examined.The product distributions in methanol differ substantially from those obtained by chlorination in carbon tetrachloride.The reaction in methanol favors addition of chlorine to the least substituted carbon α to the carbonyl group.The effect is especially pronounced if an α carbon bearing two substituents is present.The distribution of products is determined by the relative stability of the enol ethers formed from the ketone under the reaction conditions.

Halogen Epoxides, 4. Synthesis, Stability and Reactions of 2-Chloro-2-(1-chloroalkyl)oxiranes with AgBF4

Reactions of 3-chloroperbenzoic acid with 2,3-dichloro-1-butene (1a), 2,3-dichloro-3-methyl-1-butene (1b), (Z)- and (E)-1,2-dichloro-2-butene (1c, d) and with 1,2-dichloro-3-methyl-2-butene (1e) afforded the corresponding epoxides (2a - e).They rearranged slowly at room temperature and fast at elevated temperatures to form the corresponding isomeric α,α'-dichloroketones (3a, b).Reactions of the epoxides with AgBF4 produced α-chloro-α'-fluoroketones.