51-68-3

Basic information

• Product Name: 2-(Dimethylamino)ethyl (4-chlorphenoxy)acetate
• Synonyms: (4-chlorophenoxy)-aceticaci2-(dimethylamino)ethylester;(4-Chlorophenoxyaceticacid2-cdimethylan-ino)ethylester;(Dimethylamino)ethyl p-chlorophenoxyacetate;(Dimethylamino)ethyl-4-(chlorophenoxy)acetic acid;(p-Chlorophenoxy)acetic acid 2-(dimethylamino)ethyl ester;(p-Chlorophenoxy)acetic acid beta-(dimethylamino)ethyl ester;(p-chlorophenoxy)-aceticaci2-(dimethylamino)ethylester;2-(Dimethylamino)ethyl (4-chlorophenoxy)acetate
• CAS NO: 51-68-3
• Molecular Formula: C₁₂H₁₆ClNO₃
• Molecular Weight: 257.71
• EINECS: 200-116-3
• Mol File: 51-68-3.mol

Chemical Properties

• Melting Point: 138-140 °C
• Boiling Point: 345.941 °C at 760 mmHg
• Flash Point: 163.019 °C
• Appearance: /
• Density: 1.2038 (rough estimate)
• Vapor Pressure: 5.95E-05mmHg at 25°C
• Refractive Index: 1.5200 (estimate)
• PKA: 8.17±0.28(Predicted)
• CAS DataBase Reference: 2-(Dimethylamino)ethyl (4-chlorphenoxy)acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(Dimethylamino)ethyl (4-chlorphenoxy)acetate(51-68-3)
• EPA Substance Registry System: 2-(Dimethylamino)ethyl (4-chlorphenoxy)acetate(51-68-3)

Safety Data

• Hazardous Substances Data: 51-68-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H16ClNO3/c1-14(2)7-8-16-12(15)9-17-11-5-3-10(13)4-6-11/h3-6H,7-9H2,1-2H3

Synthetic route

meclofenoxate hydrochloride (3685-84-5) → meclofenoxate (51-68-3)

Conditions	Yield
With triethylamine In chloroform	78%

2-(dimethylamino)ethyl phenoxyacetate (50837-15-5) → meclofenoxate (51-68-3)

Conditions	Yield
With tetraethylammonium chloride; trichloroacetonitrile In acetonitrile at 23℃; for 2h; Electrochemical reaction; Inert atmosphere;	52%

2-(N,N-dimethylamino)ethanol (108-01-0) + 4-chlorophenyloxyacetyl chloride (4122-68-3) → meclofenoxate (51-68-3)

2-(N,N-dimethylamino)ethanol (108-01-0) + 2-(4-chlorophenoxy)-1,3-propanedioic acid diethyl ester (24101-91-5) → meclofenoxate (51-68-3)

Conditions	Yield
With sodium hydride In toluene for 10h; Heating; Yield given;

2-(N,N-dimethylamino)ethanol (108-01-0) + (4-chlorophenoxy)malonic acid (2130-69-0) → meclofenoxate (51-68-3)

Conditions	Yield
With toluene-4-sulfonic acid In xylene for 5h; Heating;

2-(N,N-dimethylamino)ethanol (108-01-0) + 2-(4-Chloro-phenoxy)-propanedioyl dichloride → meclofenoxate (51-68-3)

Conditions	Yield
In chloroform Ambient temperature; Yield given;

2-(4-chlorophenoxy)-1,3-propanedioic acid diethyl ester (24101-91-5) → meclofenoxate (51-68-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / NaOH / H2O / 2 h / Heating 2: 4-toluenesulfonic acid / xylene / 5 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 72 percent / NaOH / H2O / 2 h / Heating 2: SOCl2 / dimethylformamide / 2.5 h / Heating 3: CHCl3 / Ambient temperature View Scheme

(4-chlorophenoxy)malonic acid (2130-69-0) → meclofenoxate (51-68-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2 / dimethylformamide / 2.5 h / Heating 2: CHCl3 / Ambient temperature View Scheme

4-chloro-phenol (106-48-9) → meclofenoxate (51-68-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) NaOEt / 1.) EtOH, 40 deg C, 10 min, 2.) 40 - 50 deg C, 9 h 2: NaH / toluene / 10 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 1.) NaOEt / 1.) EtOH, 40 deg C, 10 min, 2.) 40 - 50 deg C, 9 h 2: 72 percent / NaOH / H2O / 2 h / Heating 3: 4-toluenesulfonic acid / xylene / 5 h / Heating View Scheme
Multi-step reaction with 4 steps 1: 1.) NaOEt / 1.) EtOH, 40 deg C, 10 min, 2.) 40 - 50 deg C, 9 h 2: 72 percent / NaOH / H2O / 2 h / Heating 3: SOCl2 / dimethylformamide / 2.5 h / Heating 4: CHCl3 / Ambient temperature View Scheme

4-Chlorophenoxyacetic acid (122-88-3) → meclofenoxate (51-68-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: SOCl2 View Scheme
Multi-step reaction with 3 steps 1: thionyl chloride / 2 h / 75 °C 2: chloroform 3: triethylamine / chloroform View Scheme

4-chlorophenyloxyacetyl chloride (4122-68-3) → meclofenoxate (51-68-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: chloroform 2: triethylamine / chloroform View Scheme

2-phenoxyacetic acid (122-59-8) → meclofenoxate (51-68-3)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: trichloroacetonitrile; tetraethylammonium chloride / acetonitrile / 2 h / 23 °C / Electrochemical reaction; Inert atmosphere View Scheme

1-bromo dodecane (112-29-8) + meclofenoxate (51-68-3) → C22H37ClNO3(1+)*Br(1-)

Conditions	Yield
In acetone at 55℃; for 24h;	81%

methanol (67-56-1) + meclofenoxate (51-68-3) → (4-chloro-phenoxy)-acetic acid methyl ester (4841-22-9)

Conditions	Yield
In water stability of meclofenoxate;

meclofenoxate (51-68-3) → 4-Chlorophenoxyacetic acid (122-88-3)

Conditions	Yield
In water at 30℃; stability of meclofenoxate;

meclofenoxate (51-68-3) → C22H37ClNO3(1+)*C8H5Cl2O3(1-)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetone / 24 h / 55 °C 2: sodium hydroxide / water / Heating View Scheme

meclofenoxate (51-68-3) → C22H37ClNO3(1+)*C9H8ClO3(1-)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetone / 24 h / 55 °C 2: sodium hydroxide / water / Heating View Scheme

meclofenoxate (51-68-3) → C22H37ClNO3(1+)*C10H10ClO3(1-)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetone / 24 h / 55 °C 2: sodium hydroxide / water / Heating View Scheme

meclofenoxate (51-68-3) → C22H37ClNO3(1+)*C6H2Cl2NO2(1-)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetone / 24 h / 55 °C 2: sodium hydroxide / water / Heating View Scheme

meclofenoxate (51-68-3) → C22H37ClNO3(1+)*C8H5Cl2O3(1-)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetone / 24 h / 55 °C 2: sodium hydroxide / water / Heating View Scheme

Upstream product

• 108-01-0 2-(N,N-dimethylamino)ethanol 
• 24101-91-5 2-(4-chlorophenoxy)-1,3-propanedioic acid diethyl ester 
• 2130-69-0 (4-chlorophenoxy)malonic acid 
• 106-48-9 4-chloro-phenol 
• 3685-84-5 meclofenoxate hydrochloride 
• 122-59-8 2-phenoxyacetic acid 
• 50837-15-5 2-(dimethylamino)ethyl phenoxyacetate 
• 4122-68-3 4-chlorophenyloxyacetyl chloride 
• 122-88-3 4-Chlorophenoxyacetic acid 

Downstream Products

• 4841-22-9 (4-chloro-phenoxy)-acetic acid methyl ester 
• 122-88-3 4-Chlorophenoxyacetic acid 

Relevant articles and documents

Chlorination Reaction of Aromatic Compounds and Unsaturated Carbon-Carbon Bonds with Chlorine on Demand

Chlorination with chlorine is straightforward, highly reactive, and versatile, but it has significant limitations. In this Letter, we introduce a protocol that could combine the efficiency of electrochemical transformation and the high reactivity of chlorine. By utilizing Cl3CCN as the chloride source, donating up to all three chloride atom, the reaction could generate and consume the chlorine in situ on demand to achieve the chlorination of aromatic compounds and electrodeficient alkenes.

Esterquat herbicidal ionic liquids (HILs) with two different herbicides: Evaluation of activity and phytotoxicity

Herbicidal ionic liquids (HILs) constitute a new concept in crop protection products. Their main advantage is the potential to combine the efficiency of traditional herbicides with low vapour pressure and adjustable water solubility which leads to improved environmental safety in the agricultural sector. Among many strategies to obtain new HILs, esterquats seem to be well suited for modification since both the cation and anion may be constituents of herbicides. In the framework of this study 16 new esterquat HILs were synthetized based on standard herbicides: 2,4-D, MCPA, MCPP, 4-CPA, Clopyralid and Dicamba. Germination tests performed on agricultural soil using cornflower indicated the best two HILs. Furthermore, analysis of the toxicological effects of HILs on wheat plants revealed an additional advantage of the two selected HILs. The glutathione (GSH) content and glutathione S-transferase (GST) activity showed a lower oxidative stress level in wheat plants treated with examined HILs, respectively, in comparison to a mixture of reference compounds. Finally the Ames test was applied in order to analyse the mutagenic activity of the two selected HILs.

POTENTIAL CEREBRAL STIMULANTS: ESTERS OF 2-DIMETHYLAMINOETHANOL WITH SOME LIPOPHILIC CARBOXYLIC ACIDS

2-Dimethylaminoethyl esters of 2,2-dimethylpropanoic, heptanoic, octanoic, decanoic, hexadecanoic, cyclopentylacetic, cycloheptylacetic, 2-cyclopenthylhexanoic, (4-chlorophenoxy)fumaric, and 2-(4-chlorophenoxy)succinic acid were prepared by reactions of the acid chlorides with 2-dimethylaminoethanol and were transformed to crystalline salts for pharmacological testing.The ester IX (hydrogen fumarate VUFB-14005) was found to antagonize significantly halothan amnesia in rats and the ester X (hydrogen fumarate VUFB-14004) proved to be an anticholinergic spasmolytic agent.