Product Name

  • Name

    2-(Dimethylamino)ethyl (4-chlorphenoxy)acetate

  • EINECS 200-116-3
  • CAS No. 51-68-3
  • Article Data11
  • CAS DataBase
  • Density 1.179 g/cm3
  • Solubility
  • Melting Point 138-140 °C
  • Formula C12H16ClNO3
  • Boiling Point 345.941 °C at 760 mmHg
  • Molecular Weight 257.717
  • Flash Point 163.019 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 51-68-3 (2-(Dimethylamino)ethyl (4-chlorphenoxy)acetate)
  • Hazard Symbols
  • Synonyms Aceticacid, (4-chlorophenoxy)-, 2-(dimethylamino)ethyl ester (9CI);Acetic acid,(p-chlorophenoxy)-, 2-(dimethylamino)ethyl ester (6CI,8CI);(p-Chlorophenoxy)acetic acid 2-(dimethylamino)ethyl ester;(p-Chlorophenoxy)acetic acid b-(dimethylamino)ethyl ester;2-(Dimethylamino)ethyl(p-chlorophenoxy)acetate;ANP 235;Analux;Cerebon;Cetrexin;Clocete;Dimethylaminoethyl p-chlorophenoxyacetate;EN 1627;Licidril;Meclofenoxane;Meclofenoxate;Meclophenoxate;NSC 169411;Proseryl;
  • PSA 38.77000
  • LogP 1.82360

Synthetic route

meclofenoxate hydrochloride
3685-84-5

meclofenoxate hydrochloride

meclofenoxate
51-68-3

meclofenoxate

Conditions
ConditionsYield
With triethylamine In chloroform78%
2-(dimethylamino)ethyl phenoxyacetate
50837-15-5

2-(dimethylamino)ethyl phenoxyacetate

meclofenoxate
51-68-3

meclofenoxate

Conditions
ConditionsYield
With tetraethylammonium chloride; trichloroacetonitrile In acetonitrile at 23℃; for 2h; Electrochemical reaction; Inert atmosphere;52%
2-(N,N-dimethylamino)ethanol
108-01-0

2-(N,N-dimethylamino)ethanol

4-chlorophenyloxyacetyl chloride
4122-68-3

4-chlorophenyloxyacetyl chloride

meclofenoxate
51-68-3

meclofenoxate

2-(N,N-dimethylamino)ethanol
108-01-0

2-(N,N-dimethylamino)ethanol

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

2-(4-chlorophenoxy)-1,3-propanedioic acid diethyl ester

meclofenoxate
51-68-3

meclofenoxate

Conditions
ConditionsYield
With sodium hydride In toluene for 10h; Heating; Yield given;
2-(N,N-dimethylamino)ethanol
108-01-0

2-(N,N-dimethylamino)ethanol

(4-chlorophenoxy)malonic acid
2130-69-0

(4-chlorophenoxy)malonic acid

meclofenoxate
51-68-3

meclofenoxate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In xylene for 5h; Heating;
2-(N,N-dimethylamino)ethanol
108-01-0

2-(N,N-dimethylamino)ethanol

2-(4-Chloro-phenoxy)-propanedioyl dichloride

2-(4-Chloro-phenoxy)-propanedioyl dichloride

meclofenoxate
51-68-3

meclofenoxate

Conditions
ConditionsYield
In chloroform Ambient temperature; Yield given;
2-(4-chlorophenoxy)-1,3-propanedioic acid diethyl ester
24101-91-5

2-(4-chlorophenoxy)-1,3-propanedioic acid diethyl ester

meclofenoxate
51-68-3

meclofenoxate

Conditions
ConditionsYield
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

(4-chlorophenoxy)malonic acid

meclofenoxate
51-68-3

meclofenoxate

Conditions
ConditionsYield
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

4-chloro-phenol

meclofenoxate
51-68-3

meclofenoxate

Conditions
ConditionsYield
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

4-Chlorophenoxyacetic acid

meclofenoxate
51-68-3

meclofenoxate

Conditions
ConditionsYield
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

4-chlorophenyloxyacetyl chloride

meclofenoxate
51-68-3

meclofenoxate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: chloroform
2: triethylamine / chloroform
View Scheme
2-phenoxyacetic acid
122-59-8

2-phenoxyacetic acid

meclofenoxate
51-68-3

meclofenoxate

Conditions
ConditionsYield
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

1-bromo dodecane

meclofenoxate
51-68-3

meclofenoxate

C22H37ClNO3(1+)*Br(1-)

C22H37ClNO3(1+)*Br(1-)

Conditions
ConditionsYield
In acetone at 55℃; for 24h;81%
methanol
67-56-1

methanol

meclofenoxate
51-68-3

meclofenoxate

(4-chloro-phenoxy)-acetic acid methyl ester
4841-22-9

(4-chloro-phenoxy)-acetic acid methyl ester

Conditions
ConditionsYield
In water stability of meclofenoxate;
meclofenoxate
51-68-3

meclofenoxate

4-Chlorophenoxyacetic acid
122-88-3

4-Chlorophenoxyacetic acid

Conditions
ConditionsYield
In water at 30℃; stability of meclofenoxate;
meclofenoxate
51-68-3

meclofenoxate

C22H37ClNO3(1+)*C8H5Cl2O3(1-)

C22H37ClNO3(1+)*C8H5Cl2O3(1-)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetone / 24 h / 55 °C
2: sodium hydroxide / water / Heating
View Scheme
meclofenoxate
51-68-3

meclofenoxate

C22H37ClNO3(1+)*C9H8ClO3(1-)

C22H37ClNO3(1+)*C9H8ClO3(1-)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetone / 24 h / 55 °C
2: sodium hydroxide / water / Heating
View Scheme
meclofenoxate
51-68-3

meclofenoxate

C22H37ClNO3(1+)*C10H10ClO3(1-)

C22H37ClNO3(1+)*C10H10ClO3(1-)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetone / 24 h / 55 °C
2: sodium hydroxide / water / Heating
View Scheme
meclofenoxate
51-68-3

meclofenoxate

C22H37ClNO3(1+)*C6H2Cl2NO2(1-)

C22H37ClNO3(1+)*C6H2Cl2NO2(1-)

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetone / 24 h / 55 °C
2: sodium hydroxide / water / Heating
View Scheme
meclofenoxate
51-68-3

meclofenoxate

C22H37ClNO3(1+)*C8H5Cl2O3(1-)

C22H37ClNO3(1+)*C8H5Cl2O3(1-)

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

Meclofenoxate Specification

The Meclofenoxate, with the CAS registry number 51-68-3, is also known as (p-Chlorophenoxy)acetic acid 2-(dimethylamino)ethyl ester. Its EINECS number is 200-116-3. This chemical's molecular formula is C12H16ClNO3 and molecular weight is 257.71. What's more, its systematic name is 2-(Dimethylamino)ethyl (4-chlorophenoxy)acetate. Its classification code is Drug / Therapeutic Agent. This chemical is a drug used to treat the symptoms of senile dementia and Alzheimer's disease. It is an ester of dimethylethanolamine and 4-chlorophenoxyacetic acid. It is generally considered safe. However, possible side effects may include nausea or mild dizziness. 

Physical properties of Meclofenoxate are: (1)ACD/LogP: 1.626; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.91; (4)ACD/LogD (pH 7.4): 0.79; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.47; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 26.57; (9)#H bond acceptors: 4; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 7; (12)Polar Surface Area: 38.77 Å2; (13)Index of Refraction: 1.52; (14)Molar Refractivity: 66.487 cm3; (15)Molar Volume: 218.656 cm3; (16)Polarizability: 26.357×10-24cm3; (17)Surface Tension: 39.79 dyne/cm; (18)Density: 1.179 g/cm3; (19)Flash Point: 163.019 °C; (20)Enthalpy of Vaporization: 59.006 kJ/mol; (21)Boiling Point: 345.941 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Preparation: this chemical can be prepared by esterification between parachlorophenoxyacetic acid and dimethylamine ethanol. Another kind of preparation method is that stir and dropwise add phosphorus oxychloride to the chloroform solution of parachlorophenoxyacetic acid and equimolar triethylamine. The yield is about 54%.

You can still convert the following datas into molecular structure:
(1)SMILES: Clc1ccc(OCC(=O)OCCN(C)C)cc1
(2)Std. InChI: InChI=1S/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
(3)Std. InChIKey: XZTYGFHCIAKPGJ-UHFFFAOYSA-N

The toxicity data is as follows:  

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 758mg/kg (758mg/kg) BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Farmakologiya i Toksikologiya Vol. 38, Pg. 154, 1975.
mouse LD50 oral 1750mg/kg (1750mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 386, 1972.
rabbit LD50 intravenous 150mg/kg (150mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 386, 1972.
rat LD50 oral 2600mg/kg (2600mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 386, 1972.

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