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

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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)

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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

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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.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: PHR2284
Product name: Metoclopramide Related Compound B
Purity: Pharmaceutical Secondary Standard; Certified Reference Material
Packaging: 100MG
Price: $743
Updated: 2025/07/31

Sigma-Aldrich

Product number: 463450
Product name: Methyl 4-acetamido-5-chloro-2-methoxybenzoate
Purity: 99%
Packaging: 25g
Price: $32.2
Updated: 2025/07/31

Sigma-Aldrich

Product number: 1440820
Product name: Metoclopramide Related Compound B
Purity: United States Pharmacopeia (USP) Reference Standard
Packaging: 15mg
Price: $1250
Updated: 2025/07/31

TRC

Product number: M275070
Product name: Methyl4-Acetylamino-5-chloro-2-methoxybenzoate
Packaging: 10g
Price: $80
Updated: 2021/12/16

Frontier Specialty Chemicals

Product number: JK496903
Product name: Methyl 4-acetamido-5-chloro-2-methoxybenzoate
Purity: 99%
Packaging: 10g
Price: $21
Updated: 2021/12/16

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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

Methyl p-acetaminosalicylate Methyl formate Dimethyl sulfate

Preparation Products

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View Lastest Price from Methyl 4-acetamido-5-chloro-2-methoxybenzoate manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD

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

Shaanxi Dideu Medichem Co. Ltd

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

Changzhou Rokechem Technology Co., Ltd.

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

4093-31-6, Methyl 4-acetamido-5-chloro-2-methoxybenzoateRelated Search:

Kresoxim-methyl 2-Methoxybenzoic acid Methyl acrylate 4-Methoxybenzoic acid Methylparaben 4-Dimethylaminobenzoic acid 4-Aminobenzoic acid 3-Aminobenzoic acid Methyl acetate Acetaminophen 5-Chloro-2-methylbenzoic acid Bensulfuron methyl Thiophanate-methyl Methyl Parathion-methyl Methyl bromide Anthranilic acid Difluorochloromethane

4-(acetylamino)-5-chloro-2-methoxy-benzoicacimethylester

4-ACETYLAMINO-5-CHLORO-2-METHOXY-BENZOIC ACID METHYL ESTER

4-ACETAMIDO-5-CHLORO-2-METHOXYBENZOIC ACID METHYL ESTER

LABOTEST-BB LT00441083

METHYL 4-ACETAMIDO-5-CHLORO-2-METHOXYBENZOATE

METHYL 4-ACETAMIDO-5-CHLORO-O-ANISATE

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 5-chloro-4-acetamino-2-methoxybenzoate

4-Acethylamino-2-Methoxy-5-Nitro Benzoic acid Methyl Ester

METHYL 4-(ACETYLAMIDO)-5-CHLORO-2-METHOXYBENZOATE

2-METHOXY-4-ACETAMIDO-5-CHLOROBENZOICACIDMETHYLESTER

N-ACETYL-4-AMINO-5-CHLORO-2-METHOXYBENZOIC ACID, METHYL ESTER

5-CHLOROMETHOPABATE

Benzoic acid, 4-(acetylamino)-5-chloro-2-methoxy-, methyl ester

METHYL 4-ACETAMIDO-5-CHLORO-2-METHOXYBENZOATE, 99+%

methyl 2-methoxy 4-acetamido 5-chloro benzoate

Metoclopramide Impurity 2（Metoclopramide EP Impurity B）

4-acetamido-5-chloro-2-methoxy-3-methylbenzoate

2-Methoxy-4-(acetylamino)-5-chlorobenzoic acid methyl ester

MetoclopraMide chloride

MetoclopraMide Related CoMpound B

2-Methoxy-4-acetylaMino-5-chloro Methybenzoate

Methyl 4-acetamido-5-chloro-2-methoxybenzoate 99%

Metoclopramide RC B (USP)

Metoclopramide EP Impurity B

Metoclopramide BP Impurity B

Methyl 4 -Acetamido -5- Chloro - 2 – Methoxy Benzoate(Chloromethopabate) ()

Methyl 4-(Acetylamino)-5-chloro-2-m

2-METHOXY-4-ACETYLAMINO-5-CHLORO METHYL BENZOATE 4093-31-6

lfn 642-23-9

Metoclopramide Related Compound B (methyl 4-acetamido-5-chloro-2-methoxybenzoate) (1440820)

Metoclopramide USP Related Compound B

METHYL 4-ACETAMIDO 5- CHLORO 2-METHOXYBENZOATE (5- CHLORO METHOPABATE)

MetocloprBmide EP Impurity B

Metoclopramide Hydrochloride Monohydrate Impurity B

Metoclopramide Hydrochloride Monohydrate EP Impurity B

Metoclopramide EP Impurity B (Metoclopramide USP Related Compound B)

4093-31-6

CH3CONHC6H2ClOCH3CO2CH3

C11H12ClNO4

C10 to C11

Carbonyl Compounds

Building Blocks

Organic Building Blocks

Esters

Aromatic Esters

C10 to C11

Carbonyl Compounds

Esters

(for metoclopramide Hcl)

4093-31-6