598-38-9

Basic information

• Product Name: 2,2-DICHLOROETHANOL
• Synonyms: 2,2-DICHLOROETHANOL;2,2-DICHLOROETHYL ALCOHOL;2,2-DICHLORO-1-HYDROXYETHANE;2,2-dichloro-ethano;Dichloroethanol
• CAS NO: 598-38-9
• Molecular Formula: C₂H₄Cl₂O
• Molecular Weight: 114.96
• EINECS: 209-931-9
• Product Categories: Alcohols;C2 to C6;Oxygen Compounds
• Mol File: 598-38-9.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 146 °C(lit.)
• Flash Point: 173 °F
• Appearance: colourless to light yellow liquid
• Density: 1.404 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.86mmHg at 25°C
• Refractive Index: n20/D 1.473(lit.)
• Storage Temp.: Refrigerator
• Solubility: Chloroform
• PKA: 13.09±0.10(Predicted)
• Stability: Stable. Combustible. Incompatible with oxidizing agents.
• CAS DataBase Reference: 2,2-DICHLOROETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2-DICHLOROETHANOL(598-38-9)
• EPA Substance Registry System: 2,2-DICHLOROETHANOL(598-38-9)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-40
• Safety Statements: 7-23-36/37/39-45
• WGK Germany: 3
• RTECS: KK4100000
• Hazardous Substances Data: 598-38-9(Hazardous Substances Data)

Usage

Description

2,2-Dichloroethanol, also known as ethylene dichloride or 1,2-dichloroethane, is an organic compound with the chemical formula C2H4Cl2. It is a colourless to light yellow liquid that is used as a reagent in various chemical processes. Its molecular structure features two chlorine atoms attached to the carbon atoms of an ethylene molecule, which contributes to its unique chemical properties and applications.

Uses

Used in Chemical Synthesis:
2,2-Dichloroethanol is used as a reagent in the preparation of tunable molecular catalysts via functionalizing the methylene bridge of bis(N-heterocyclic carbene) ligands. This application takes advantage of its chemical properties to facilitate the synthesis of catalysts that can be tailored for specific chemical reactions.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,2-dichloroethanol is utilized as a solvent for the synthesis of various drugs and active pharmaceutical ingredients. Its ability to dissolve a wide range of compounds makes it a versatile and valuable component in the development of new medications.
Used in Industrial Chemical Production:
2,2-Dichloroethanol is also employed in the production of other industrial chemicals, such as ethylene glycol, which is used in the manufacturing of antifreeze, polyester fibers, and polyethylene terephthalate (PET) plastics. Its role in these processes highlights its importance in the broader chemical industry.
Used in Laboratory Research:
Due to its unique chemical properties, 2,2-dichloroethanol is often used in laboratory settings for research purposes. It serves as a valuable tool for chemists to study various chemical reactions and develop new synthetic methods, contributing to the advancement of chemical science.

Air & Water Reactions

Water soluble.

Reactivity Profile

2,2-DICHLOROETHANOL is incompatible with oxidizing agents.

Fire Hazard

2,2-DICHLOROETHANOL is combustible.

InChI:InChI=1/C2H4Cl2O/c3-2(4)1-5/h2,5H,1H2

Upstream product

• 79-43-6 dichloro-acetic acid 
• 79-02-7 2,2-dichloroacetaldehyde 
• 108743-23-3 Acetaldehyd-mono-<2,2-dichlor-ethylacetal> 
• 64020-50-4 2-(2,2-dichloroethoxy)-2-phenyl-1,3-dioxolane 
• 84336-27-6 diethoxyphosphoryldichloroacetaldehyde 
• 201601-92-5 Phosphoric acid 2,2-dichloro-ethyl ester (2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-2-hydroxymethyl-tetrahydro-furan-3-yl ester 
• 103413-89-4 Dichlorethyl-p-nitrobenzoat 
• 94670-22-1 1-[1-(2,2-Dichloro-ethoxy)-ethyl]-4-methoxy-benzene 
• 94670-09-4 {4-[1-(2,2-Dichloro-ethoxy)-ethyl]-phenyl}-dimethyl-amine; compound with perchloric acid 
• 94669-98-4 1-(4-methoxy-3-nitrophenyl)ethyl 2,2-dichloroethyl ether 
• 23273-87-2 C₂H₃Cl₂ 
• 127935-87-9 2,2-dichloroethyl nitrite 
• 67796-29-6 (2,2-dichloro-ethoxy)-methanol 
• 75-89-8 2,2,2-trifluoroethanol 

Downstream Products

• 28049-04-9 3-phenylpropionic acid 2,2-dichloroethyl ester 
• 37934-98-8 benzoic acid 2,2-dichloroethyl ester 
• 79-43-6 dichloro-acetic acid 
• 862893-88-7 γ-butyrolactone 
• 335370-72-4 2,2-dichloroethyl benzyl ether 
• 69395-06-8 Diphenylphosphorsaeure-2,2-dichlorethylester 
• 75-89-8 2,2,2-trifluoroethanol 
• 94669-98-4 1-(4-methoxy-3-nitrophenyl)ethyl 2,2-dichloroethyl ether 
• 94670-09-4 {4-[1-(2,2-Dichloro-ethoxy)-ethyl]-phenyl}-dimethyl-amine; compound with perchloric acid 

Relevant articles and documents

Predominant role of basicity of leaving group in α-effect for nucleophilic ester cleavage

It has been found that α-effects in nucleophilic reactions, unexpectedly large nucleophilicity due to adjacent unpaired electrons, are strongly dependent on the structure of substrate. The nucleophilic cleavages of 4-nitrobenzoate esters and 4-methylbenzo

Acylphosphonate hemiketals - Formation rate and equilibrium. The electron-withdrawing effect of dimethoxyphosphinyl group

Examination of alcoholic solutions of dimethyl acetylphosphonate (1) and dimethyl benzoylphosphonate (2) by 31P NMR spectroscopy reveals the presence of considerable amounts of hemiketals. Because of the great difference between the 31P chemical shifts of acylphosphonates (ca. 0 ppm) and their hemiketals (17-21 ppm), 31P NMR spectroscopy is a uniquely suitable method for studying the rates and equilibria of hemiketal formation of acylphosphonates with different alcohols. The equilibrium constants Kf, K′f (K′f = Kf[ROH]), pseudo-first-order rate constants k′f, the second order rate constants, kf for hemiketal formation from dimethyl acetylphosphonate with various alcohols, as well as the reverse reaction rate constants, kr to starting materials, were determined. The kinetic isotope effect of 2.8 for the forward reaction kf (EtOH addition) and the backward reaction kr indicates a general catalysis pathway. On the other hand, the calculated values of the enthalpies of activation ΔH? = 10.37 kcal mol-1 (forward), ΔH? = 13.66 kcal mol-1 (backward) and the entropies of activation, ΔS? = -17.25 cal mol-1 K-1 (forward), ΔS? = -9.82 cal mol-1 K-1 (backward) are not in accord with high molecularity of the reaction (1 cal = 4.184 J). Our analysis led to the conclusion that this is probably due to the fact that the transition state is mainly reactant-like with the development of only limited extent of bond formation. Various plausible reaction pathways for hemiketal formation are discussed. In addition, we have calculated the value of 2.65 σ* for the P(O)(OMe)2 group based on proton affinity obtained from heats of formation (ΔHf) of applying the MNDO techniques. The following linear correlation between pKa values and PA values of hemiketals of the form (Me)(R)C(OH)(OCH2X) was developed: pKa = PA - 356.58 + 9.18 [σ*(Me) + σ*(R) + 0.2σ*(X)].

Cyclization-Activated Prodrugs: N-(Substituted 2-hydroxyphenyl and 2-hydroxypropyl)carbamates Based on Ring-Opened Derivatives of Active Benzoxazolones and Oxazolidinones as Mutual Prodrugs of Acetaminophen

N-(Substituted 2-hydroxyphenyl)- and N-(substituted 2-hydroxypropyl)carbamates based on masked active benzoxazolones (model A) and oxazolidinones (model B), respectively, were synthesized and evaluated as potential drug delivery systems.A series of alkyl and aryl N-(5-chloro-2-hydroxyphenyl)carbamates 1 related to model A was prepared.These are open drugs of the skeletal muscle relaxant chlorzoxazone.The corresponding 4-acetamidophenyl ester named chloracetamol is a mutual prodrug of chloroxazone and acetaminophen.Chlorzacetamol and two other mutual prodrugs of active bezoxazolones and acetaminophen were obtained in a two-step process via condensation of 4-acetamidophenyl 1,2,2,2-tetrachloroethyl carbonate with the appropiate anilines.Based on model B, two mutual prodrugs of acetaminophen and active oxazolidinones (metaxalone and mephenoxalone) were similarly obtained using the appropiate amines.All the carbamate prodrugs prepared were found to release the parent drugs in aqueous (pH 6-11) and plasma (pH 7.4) media.The detailed mechanistic study of prodrugs 1 carried out in aqueous medium at 37 deg C shows a change in the Broensted-type relationship log t1/2 vs pKa of the leaving groups ROH: log t1/2 = 0.46pKa - 3.55 for aryl and trihalogenoethyl esters and log t1/2 = 1.46pKa - 16.03 for alkyl esters.This change is consistent with a cyclization mechanism involving a change in the rate-limiting step from formation of a cyclic tetrahedral intermediate (step k1) to departure of the leaving group ROH (step k2) when the leaving group ability decreases.This mechanism occurs for all the prodrugs related to model A.Regeneration of the parent drugs from mutual prodrugs related to model B takes place by means of a rate-limiting elimination-addition reaction (E1cB mechanism).This affords acetaminophen and the corresponding 2-hydroxypropyl isocyanate intermediates which cyclize at any pH to the corresponding oxazolidinone drugs.As opposed to model A, the rates of hydrolysis of mutual prodrugs of model B clearly exhibit a catalytic role of the plasma.It is concluded from the plasma studies that the carbamate substrates can be enzymatically transformed into potent electrophiles, i.e., isocyanates.In the case of the present study, the prodrugs are 2-hydroxycarbamates for which the propinquity of the hydroxyl residue and the isocyanate group enforces a cyclization reaction.This mechanistic particularity precludes their potential toxicity in terms of potent electrophiles capable of modifying critical macromolecules.