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Meclofenoxate

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Name

Meclofenoxate

EINECS 200-116-3
CAS No. 51-68-3 Density 1.179 g/cm3
PSA 38.77000 LogP 1.82360
Solubility N/A 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 N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 51-68-3 (2-(Dimethylamino)ethyl (4-chlorphenoxy)acetate) Hazard Symbols N/A
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;

Article Data 11

Meclofenoxate Synthetic route

3685-84-5

meclofenoxate hydrochloride

51-68-3

meclofenoxate

Conditions
ConditionsYield
With triethylamine In chloroform78%
50837-15-5

2-(dimethylamino)ethyl phenoxyacetate

51-68-3

meclofenoxate

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

2-(N,N-dimethylamino)ethanol

4122-68-3

4-chlorophenyloxyacetyl chloride

51-68-3

meclofenoxate

108-01-0

2-(N,N-dimethylamino)ethanol

24101-91-5

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

51-68-3

meclofenoxate

Conditions
ConditionsYield
With sodium hydride In toluene for 10h; Heating; Yield given;
108-01-0

2-(N,N-dimethylamino)ethanol

2130-69-0

(4-chlorophenoxy)malonic acid

51-68-3

meclofenoxate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In xylene for 5h; Heating;
108-01-0

2-(N,N-dimethylamino)ethanol

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

51-68-3

meclofenoxate

Conditions
ConditionsYield
In chloroform Ambient temperature; Yield given;
24101-91-5

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

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
2130-69-0

(4-chlorophenoxy)malonic acid

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
106-48-9

4-chloro-phenol

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
122-88-3

4-Chlorophenoxyacetic acid

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

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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