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Methyl 4-acetamido-5-chloro-2-methoxybenzoate

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Name

Methyl 4-acetamido-5-chloro-2-methoxybenzoate

EINECS 223-840-1
CAS No. 4093-31-6 Density 1.312 g/cm3
PSA 64.63000 LogP 2.16660
Solubility 1.14g/L at 25℃ Melting Point 153-156 °C
Formula C11H12ClNO4 Boiling Point 440.2 °C at 760 mmHg
Molecular Weight 257.674 Flash Point 220 °C
Transport Information N/A Appearance white to light beige fine crystalline powder
Safety 24/25-36-26 Risk Codes 20/21/22-36/37/38
Molecular Structure Molecular Structure of 4093-31-6 (Methyl 4-acetamido-5-chloro-2-methoxybenzoate) Hazard Symbols HarmfulXn
Synonyms

o-Anisicacid, 4-acetamido-5-chloro-, methyl ester (7CI,8CI);4-Acetamido-5-chloro-2-methoxybenzoic acid methyl ester;4-Acetylamino-5-chloro-2-methoxybenzoic acid methyl ester;Methyl2-methoxy-4-acetamido-5-chlorobenzoate;Methyl2-methoxy-4-acetylamino-5-chlorobenzoate;Methyl4-(acetylamino)-5-chloro-2-(methyloxy)benzoate;Methyl 4-acetamido-5-chloro-o-anisate;Methyl4-acetylamino-5-chloro-2-methoxybenzoate;

Article Data 17

Methyl 4-acetamido-5-chloro-2-methoxybenzoate Synthetic route

4093-29-2

methyl 4-(acetylamino)-o-anisate

4093-31-6

methyl 2-methoxy 4-acetamido 5-chloro benzoate

Conditions
ConditionsYield
With N-chloro-succinimide In N,N-dimethyl-formamide at 40 - 65℃; for 9h; Temperature;90.3%
With palladium diacetate; copper diacetate; copper dichloride In dichloromethane at 90℃; for 48h;30%
With sodium hypochlorite for 1h; Yield given;
With N-chloro-succinimide In N,N-dimethyl-formamide
20896-27-9

methyl 4-amino-5-chloro-2-methoxybenzoate

108-24-7

acetic anhydride

4093-31-6

methyl 2-methoxy 4-acetamido 5-chloro benzoate

Conditions
ConditionsYield
With acetic acid at 50℃; for 5h;80%
20896-27-9

methyl 4-amino-5-chloro-2-methoxybenzoate

64-19-7

acetic acid

75-36-5

acetyl chloride

4093-31-6

methyl 2-methoxy 4-acetamido 5-chloro benzoate

Conditions
ConditionsYield
for 12h; Reflux;67%
538372-32-6

6-amino-5-nitro-pyridine-2-carboxylic acid methyl ester

A

imidazo[4,5-b]pyridine-pyrrole

imidazo[4,5-b]pyridine-pyrrole

B

4093-31-6

methyl 2-methoxy 4-acetamido 5-chloro benzoate

Conditions
ConditionsYield
hydrogen In palladium-carbonA n/a
B 63%
27492-84-8

Methyl 4-amino-2-methoxybenzoate

4093-31-6

methyl 2-methoxy 4-acetamido 5-chloro benzoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2O / 1.) room temp., 30 min., 2.) 60-70 deg C, 1 h
2: aq. sodium hypochlorite / 1 h
View Scheme
Multi-step reaction with 2 steps
1: N-chloro-succinimide / acetonitrile / 3 h / Reflux
2: 12 h / Reflux
View Scheme
20896-27-9

methyl 4-amino-5-chloro-2-methoxybenzoate

4093-31-6

methyl 2-methoxy 4-acetamido 5-chloro benzoate

Conditions
ConditionsYield
With acetic acid In acetic anhydride
4093-28-1

methyl 4-acetamido-2-hydroxybenzoate

4093-31-6

methyl 2-methoxy 4-acetamido 5-chloro benzoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / N,N-dimethyl-formamide
2: N-chloro-succinimide / N,N-dimethyl-formamide
View Scheme
65-49-6

4-Aminosalicylic acid

4093-31-6

methyl 2-methoxy 4-acetamido 5-chloro benzoate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sulfuric acid / 2 h / 20 °C
2: acetic acid / 1 h
3: sodium hydroxide / N,N-dimethyl-formamide
4: N-chloro-succinimide / N,N-dimethyl-formamide
View Scheme
4136-97-4

methyl 4-aminosalicylate

4093-31-6

methyl 2-methoxy 4-acetamido 5-chloro benzoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: acetic acid / 1 h
2: sodium hydroxide / N,N-dimethyl-formamide
3: N-chloro-succinimide / N,N-dimethyl-formamide
View Scheme
7206-70-4

4-amino-5-chloro-2-methoxybenzoic acid

4093-31-6

methyl 2-methoxy 4-acetamido 5-chloro benzoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: thionyl chloride / 5 h / 80 °C
2: acetic acid / 5 h / 50 °C
View Scheme

Methyl 4-acetamido-5-chloro-2-methoxybenzoate Specification

The IUPAC Name of Methyl 4-acetamido-5-chloro-o-anisate is methyl 4-acetamido-5-chloro-2-methoxybenzoate. With the CAS registry number 4093-31-6 and EINECS 223-840-1, it is also named as Benzoic acid, 4-(acetylamino)-5-chloro-2-methoxy-, methyl ester. The product's categories are Aromatic Esters; C10 to C11; Carbonyl Compounds; Esters. It is white to light beige fine crystalline powder which is stable under normal temperature and pressure. Additionally, this chemical should be sealed in the container, avoided direct sunshine and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.24; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.24; (4)ACD/LogD (pH 7.4): 2.24; (5)ACD/BCF (pH 5.5): 29.55; (6)ACD/BCF (pH 7.4): 29.55; (7)ACD/KOC (pH 5.5): 392.88; (8)ACD/KOC (pH 7.4): 392.88; (9)#H bond acceptors: 5; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 55.84 Å2; (13)Index of Refraction: 1.564; (14)Molar Refractivity: 63.87 cm3; (15)Molar Volume: 196.3 cm3; (16)Surface Tension: 44.9 dyne/cm; (17)Enthalpy of Vaporization: 69.73 kJ/mol; (18)Vapour Pressure: 5.99E-08 mmHg at 25°C; (19)Rotatable Bond Count: 4; (20)Tautomer Count: 4; (21)Exact Mass: 257.045486; (22)MonoIsotopic Mass: 257.045486; (23)Topological Polar Surface Area: 64.6; (24)Heavy Atom Count: 17; (25)Complexity: 297.

Preparation: The Methyl p-acetaminosalicylate reacts with dimethyl sulfate to get compound 1. After etherification, we can obtain acetaminophen- o-methoxy methyl formate. Using chlorine to chloridize the latter product, we get Methyl 4-acetamido-5-chloro-o-anisate.

Uses of Methyl 4-acetamido-5-chloro-o-anisate: It is the intermediate of metoclopramide. It also can be used to produce 4-acetylamino-5-chloro-2-methoxy-3-nitro-benzoic acid methyl ester. This reaction needs reagents conc. H2SO4 and fuming HNO3 at temperature of 10 °C. The reaction time is 5 min. The yield is 73%.

When you are using this chemical, please be cautious about it as the following:
It is not only harmful by inhalation, in contact with skin and if swallowed, but also irritating to eyes, respiratory system and skin. So people should avoid contact with skin and eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.

People can use the following data to convert to the molecule structure. 
1. SMILES:Clc1cc(c(OC)cc1NC(=O)C)C(=O)OC
2. InChI:InChI=1/C11H12ClNO4/c1-6(14)13-9-5-10(16-2)7(4-8(9)12)11(15)17-3/h4-5H,1-3H3,(H,13,14)
3. InChIKey:OUEXNQRVYGYGIK-UHFFFAOYAB

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