Methyl 4-acetamido-5-chloro-2-methoxybenzoate
- Product Name
- Methyl 4-acetamido-5-chloro-2-methoxybenzoate
- CAS No.
- 4093-31-6
- Chemical Name
- Methyl 4-acetamido-5-chloro-2-methoxybenzoate
- Synonyms
- MetoclopraMide Related CoMpound B;Metoclopramide EP Impurity B;lfn 642-23-9;5-CHLOROMETHOPABATE;LABOTEST-BB LT00441083;MetoclopraMide chloride;Metoclopramide RC B (USP);Metoclopramide BP Impurity B;MetocloprBmide EP Impurity B;Methyl 4-(Acetylamino)-5-chloro-2-m
- CBNumber
- CB5404478
- Molecular Formula
- C11H12ClNO4
- Formula Weight
- 257.67
- MOL File
- 4093-31-6.mol
Methyl 4-acetamido-5-chloro-2-methoxybenzoate Property
- 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
- Benzoic acid, 4-(acetylamino)-5-chloro-2-methoxy-, methyl ester (4093-31-6)
Safety
- Hazard Codes
- Xn
- Risk Statements
- 20/21/22-36/37/38
- Safety Statements
- 24/25-36-26
- WGK Germany
- 3
- TSCA
- Yes
- HS Code
- 29242990
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
N-Bromosuccinimide Price
- Product number
- PHR2284
- Product name
- Metoclopramide Related Compound B
- Purity
- Pharmaceutical Secondary Standard; Certified Reference Material
- Packaging
- 100MG
- Price
- $743
- Updated
- 2025/07/31
- Product number
- 463450
- Product name
- Methyl 4-acetamido-5-chloro-2-methoxybenzoate
- Purity
- 99%
- Packaging
- 25g
- Price
- $32.2
- Updated
- 2025/07/31
- Product number
- 1440820
- Product name
- Metoclopramide Related Compound B
- Purity
- United States Pharmacopeia (USP) Reference Standard
- Packaging
- 15mg
- Price
- $1250
- Updated
- 2025/07/31
- Product number
- M275070
- Product name
- Methyl4-Acetylamino-5-chloro-2-methoxybenzoate
- Packaging
- 10g
- Price
- $80
- Updated
- 2021/12/16
- Product number
- E970
- Product name
- Methyl 4-acetamido-5-chloro-2-methoxybenzoate
- Packaging
- 5g
- Price
- $15
- Updated
- 2021/12/16
Methyl 4-acetamido-5-chloro-2-methoxybenzoate Chemical Properties,Usage,Production
Chemical Properties
white to light beige fine crystalline powder
Uses
Methyl 4-Acetylamino-5-chloro-2-methoxybenzoate (Metoclopramide EP Impurity B; Metoclopramide USP Related Compound B) is an biotransformed metabolite of Metoclopramide (M338685), an dopamine D2 receptor antagonist and antiemetic agent.
Uses
Methyl 4-Acetylamino-5-chloro-2-methoxybenzoate is an biotransformed metabolite of Metoclopramide (M338685), an dopamine D2 receptor antagonist and antiemetic agent.
Synthesis
4093-29-2
4093-31-6
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
Methyl 4-acetamido-5-chloro-2-methoxybenzoate Preparation Products And Raw materials
Raw materials
Preparation Products
Methyl 4-acetamido-5-chloro-2-methoxybenzoate Suppliers
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View Lastest Price from Methyl 4-acetamido-5-chloro-2-methoxybenzoate manufacturers
- Product
- Methyl 4-acetamido-5-chloro-2-methoxybenzoate 4093-31-6
- Price
- US $0.00-0.00/Kg/Drum
- Min. Order
- 1KG
- Purity
- 98%min
- Supply Ability
- 500kg
- Release date
- 2021-09-14
- Product
- LABOTEST-BB LT00441083 4093-31-6
- Price
- US $30.00-20.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 200000KG
- Release date
- 2024-08-01
- Product
- Methyl 4-Acetamido-5-Chloro-2-Methoxybenzoate 4093-31-6
- Price
- US $0.00-0.00/Kg
- Min. Order
- 1Kg
- Purity
- 99%
- Supply Ability
- 1-10000kgs
- Release date
- 2023-07-25