| Identification | More | [Name]
Methyl 4-acetamido-5-chloro-2-methoxybenzoate | [CAS]
4093-31-6 | [Synonyms]
4-ACETAMIDO-5-CHLORO-2-METHOXYBENZOIC ACID METHYL ESTER
4-ACETYLAMINO-5-CHLORO-2-METHOXY-BENZOIC ACID METHYL ESTER
LABOTEST-BB LT00441083
METHYL 4-ACETAMIDO-5-CHLORO-2-METHOXYBENZOATE
METHYL 4-ACETAMIDO-5-CHLORO-O-ANISATE
4-(acetylamino)-5-chloro-2-methoxy-benzoicacimethylester
Methyl 5-chloro-4-acetamino-2-methoxybenzoate
4-Acethylamino-2-Methoxy-5-Nitro Benzoic acid Methyl Ester
5-Chloro-4-acetamid-2-methoxy methyl benzoate
5-Chloro-4-acetamido-2-methoxybenzoic acid methylester
Methyl-2-methoxy-4-acetylamino-5-chlorobenzoate
Acetamido-5-chloro-2-methoxybenzoicacidmethylester
METHYL 4-(ACETYLAMIDO)-5-CHLORO-2-METHOXYBENZOATE
2-METHOXY-4-ACETAMIDO-5-CHLOROBENZOICACIDMETHYLESTER
5-CHLOROMETHOPABATE
N-ACETYL-4-AMINO-5-CHLORO-2-METHOXYBENZOIC ACID, METHYL ESTER
Benzoic acid, 4-(acetylamino)-5-chloro-2-methoxy-, methyl ester
METHYL 4-ACETAMIDO-5-CHLORO-2-METHOXYBENZOATE, 99+%
2-Methoxy-4-(acetylamino)-5-chlorobenzoic acid methyl ester | [EINECS(EC#)]
223-840-1 | [Molecular Formula]
C11H12ClNO4 | [MDL Number]
MFCD00048191 | [Molecular Weight]
257.67 | [MOL File]
4093-31-6.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light beige fine crystalline powder | [Melting point ]
153-156 °C
| [Boiling point ]
440.2±45.0 °C(Predicted) | [density ]
1.3248 (rough estimate) | [refractive index ]
1.6000 (estimate) | [storage temp. ]
2-8°C | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
13.16±0.70(Predicted) | [color ]
White to Off-White | [Water Solubility ]
1.14g/L at 25℃ | [InChI]
InChI=1S/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) | [InChIKey]
OUEXNQRVYGYGIK-UHFFFAOYSA-N | [SMILES]
C(OC)(=O)C1=CC(Cl)=C(NC(C)=O)C=C1OC | [LogP]
1.49 at 20℃ | [CAS DataBase Reference]
4093-31-6(CAS DataBase Reference) | [EPA Substance Registry System]
4093-31-6(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S24/25:Avoid contact with skin and eyes .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3 | [TSCA ]
Yes | [HS Code ]
29242990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Dermal
Acute Tox. 4 Inhalation
Acute Tox. 4 Oral |
| Hazard Information | Back Directory | [Chemical Properties]
white to light beige fine crystalline powder | [Uses]
Methyl 4-Acetylamino-5-chloro-2-methoxybenzoate is an biotransformed metabolite of Metoclopramide (M338685), an dopamine D2 receptor antagonist and antiemetic agent. | [Synthesis]
General procedure for the synthesis of methyl 4-acetamido-5-chloro-2-methoxybenzoate from methyl 4-acetamido-2-methoxybenzoate: 136g of N,N-dimethylformamide (DMF) was added as solvent in a 1L reaction flask, followed by the addition of 50g of methyl 4-acetamido-2-methoxybenzoate, and stirred until it was completely dissolved. To the solution was added 50 g of N-chlorosuccinimide (NCS), which was slowly heated to 40 °C and the reaction was maintained at this temperature for 5 hours. The reaction temperature was then raised to 65 °C and the reaction continued for 4 hours. Upon completion of the reaction, the reaction mixture was cooled to 0 °C and thermo-crystallization was carried out for 8 h. The crude product of methyl 4-acetamido-5-chloro-2-methoxybenzoate was obtained, while the mother liquor of N,N-dimethylformamide was recovered. The crude product was dissolved in 100 g of deionized water, heated to 50 °C and kept for 4 hours, then cooled to 5 °C for filtration. The filtered solid was dried to obtain a white crystalline product, methyl 4-acetamido-5-chloro-2-methoxybenzoate 52.1 g, with a molar yield of 90.3% and HPLC purity ≥99.8%. | [References]
[1] Patent: CN105523952, 2016, A. Location in patent: Paragraph 0029
[2] Journal of the American Chemical Society, 2006, vol. 128, # 23, p. 7416 - 7417
[3] Archiv der Pharmazie, 1980, vol. 313, # 4, p. 297 - 300
[4] Letters in Drug Design and Discovery, 2012, vol. 9, # 5, p. 489 - 493 |
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