118-04-7

Basic information

• Product Name: 2-(3-Amino-4-chloro-benzoyl)benzoic acid
• Synonyms: 2-(3-amino-4-chlorobenzoyl)-benzoicaci;2-(4-CHLORO-3-AMINOBENZOYL) BENZOIC ACID;2-(3'-AMINO-4'-CHLOROBENZOYL)BENZOIC ACID;2-(3-AMINO-4-CHLOROBENZOYL)BENZOIC ACID;LABOTEST-BB LT00012586;3-Amino-2-Carboxy-4-Chlorobenzophenone;BENZOIC ACID, 2-(3-AMINO-4-CHLOROBENZOYL);2-(3-Amino-4-chlorobenzoyl)benzoicacid（NH2-CBB）
• CAS NO: 118-04-7
• Molecular Formula: C₁₄H₁₀ClNO₃
• Molecular Weight: 275.69
• EINECS: 204-230-4
• Product Categories: Organic acids
• Mol File: 118-04-7.mol
• Article Data: 3

Chemical Properties

• Melting Point: 181.5-182.0 °C(Solv: ethanol (64-17-5))
• Boiling Point: 538.6 °C at 760 mmHg
• Flash Point: 279.5 °C
• Appearance: white crystal
• Density: 1.418 g/cm³
• Vapor Pressure: 1.97E-12mmHg at 25°C
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 3.24±0.36(Predicted)
• CAS DataBase Reference: 2-(3-Amino-4-chloro-benzoyl)benzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3-Amino-4-chloro-benzoyl)benzoic acid(118-04-7)
• EPA Substance Registry System: 2-(3-Amino-4-chloro-benzoyl)benzoic acid(118-04-7)

Safety Data

• Hazardous Substances Data: 118-04-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-(3-Amino-4-chloro-benzoyl)benzoic acid is used as a synthetic intermediate for the preparation of protein kinase C phosphorylates, which are essential in the development of drugs targeting protein kinases. These kinases play a crucial role in various cellular processes, including cell growth, differentiation, and apoptosis, making them attractive targets for therapeutic intervention in various diseases, such as cancer and inflammatory disorders.
Used in Chemical Research:
2-(3-Amino-4-chloro-benzoyl)benzoic acid is also used as a synthetic intermediate in the preparation of synthetic fluorescent reporters. These reporters are valuable tools in chemical and biological research, as they allow for the visualization and tracking of specific molecules or cellular processes. The unique structure of 2-(3-Amino-4-chloro-benzoyl)benzoic acid enables the development of fluorescent reporters with specific properties, such as emission wavelengths, quantum yields, and photostability, which can be tailored to the needs of various research applications.

InChI:InChI=1/C14H10ClNO3/c15-11-6-5-8(7-12(11)16)13(17)9-3-1-2-4-10(9)14(18)19/h1-7H,16H2,(H,18,19)/p-1

Synthetic route

2-(4'-chloro-3'-nitrobenzoyl)benzoic acid (85-54-1) → NSC 74496 (118-04-7)

Conditions	Yield
With hydrogen; sodium carbonate; Pt/Al2O3 In water at 60 - 80℃; under 15001.2 - 30002.4 Torr;	98%
Stage #1: 2-(4'-chloro-3'-nitrobenzoyl)benzoic acid With sodium nitrate; potassium carbonate; 5-chloroanthranilic acid; potassium iodide; copper(l) chloride at 60 - 70℃; for 3h; Stage #2: With ammonium chloride; sodium hydrogensulfite at 20 - 50℃; for 1.5h; Concentration;	95%
With chromium dichloride; manganese; chloro-trimethyl-silane In tetrahydrofuran Reduction;	70%
With hydrogenchloride; tin(ll) chloride In ethanol

2-(4-chlorobenzoyl)benzoic acid (85-56-3) → NSC 74496 (118-04-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: NO2/HNO3 / Ambient temperature 2: SnCl2, aq. HCl / ethanol View Scheme

acetic anhydride (108-24-7) + NSC 74496 (118-04-7) → 2-(3-acetylamino-4-chloro-benzoyl)-benzoic acid

Conditions	Yield
With acetic acid

NSC 74496 (118-04-7) → 2-chloro-3-hydroxy-anthraquinone (733053-53-7)

Conditions	Yield
With sulfuric acid; acetic acid Diazotization.Erhitzen der mit konz.Schwefelsaeure versetzten Diazoloesung auf 200grad;

NSC 74496 (118-04-7) → 1-amino-4-bromo-2-chloro-anthraquinone (4859-54-5) + 2-amino-1-bromo-3-chloro-anthraquinone (117-01-1)

Conditions	Yield
With sulfuric acid Behandeln der mit Wasser versetzten Reaktionsloesung mit Brom;

NSC 74496 (118-04-7) → 1-amino-2-chloro-9,10-anthraquinone (117-07-7) + 2-amino-3-chloro-9,10-anthracenedione (84-46-8)

Conditions	Yield
With sulfuric acid

NSC 74496 (118-04-7) → 2-amino-3-chloro-9,10-anthracenedione (84-46-8)

Conditions	Yield
With sulfuric acid at 200℃;

NSC 74496 (118-04-7) → 2-(3-amino-4-chloro-benzyl)-benzoic acid (858842-54-3)

Conditions	Yield
With ammonium hydroxide; copper(II) sulfate; zinc

NSC 74496 (118-04-7) → 2-(4-chloro-3-chlorosulfonyl-benzoyl)-benzoic acid (68592-12-1)

Conditions	Yield
With hydrogenchloride; acetic acid; sodium nitrite und anschliessed mit SO2 und CuCl2;

sulfuric acid (7664-93-9) + NSC 74496 (118-04-7) → 2-amino-3-chloro-9,10-anthracenedione (84-46-8)

Conditions	Yield
at 200℃;

sulfuric acid (7664-93-9) + NSC 74496 (118-04-7) → 1-amino-2-chloro-9,10-anthraquinone (117-07-7) + 2-amino-3-chloro-9,10-anthracenedione (84-46-8)

sodium cyanide (143-33-9) + NSC 74496 (118-04-7) + copper (I)-cyanide → 2-(4-chloro-3-cyano-benzoyl)-benzoic acid

Conditions	Yield
With hydrogenchloride; sodium nitrite

NSC 74496 (118-04-7) → 6'-chloro-2,3'-carbonyl-di-benzoic acid

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium nitrite; aqueous hydrochloric acid 2: aq. NaOH solution View Scheme

NSC 74496 (118-04-7) → 2-(4-chloro-3-sulfamoyl-benzoyl)-benzoic acid (5270-74-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous HCl; acetic acid; NaNO2 / und anschliessed mit SO2 und CuCl2 2: water; NH3 View Scheme

NSC 74496 (118-04-7) → 2-(4-chloro-3-sulfamoyl-benzoyl)-benzoic acid methyl ester (92433-89-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: aqueous HCl; acetic acid; NaNO2 / und anschliessed mit SO2 und CuCl2 2: water; NH3 3: thionyl chloride View Scheme

NSC 74496 (118-04-7) → 2-chloro-5-(1-chloro-3-oxo-phthalan-1-yl)-benzenesulfonyl chloride (68592-11-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous HCl; acetic acid; NaNO2 / und anschliessed mit SO2 und CuCl2 2: chloroform; phosphorus (V)-chloride View Scheme

NSC 74496 (118-04-7) → 2-chloro-5-(1-chloro-3-oxo-phthalan-1-yl)-benzenesulfonic acid amide (106522-14-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: aqueous HCl; acetic acid; NaNO2 / und anschliessed mit SO2 und CuCl2 2: water; NH3 3: thionyl chloride View Scheme

Upstream product

• 85-54-1 2-(4'-chloro-3'-nitrobenzoyl)benzoic acid 
• 85-56-3 2-(4-chlorobenzoyl)benzoic acid 

Downstream Products

• 4859-54-5 1-amino-4-bromo-2-chloro-anthraquinone 
• 117-01-1 2-amino-1-bromo-3-chloro-anthraquinone 
• 117-07-7 1-amino-2-chloro-9,10-anthraquinone 
• 84-46-8 2-amino-3-chloro-9,10-anthracenedione 
• 858842-54-3 2-(3-amino-4-chloro-benzyl)-benzoic acid 
• 68592-12-1 2-(4-chloro-3-chlorosulfonyl-benzoyl)-benzoic acid 
• 5270-74-6 2-(4-chloro-3-sulfamoyl-benzoyl)-benzoic acid 
• 92433-89-1 2-(4-chloro-3-sulfamoyl-benzoyl)-benzoic acid methyl ester 
• 68592-11-0 2-chloro-5-(1-chloro-3-oxo-phthalan-1-yl)-benzenesulfonyl chloride 
• 106522-14-9 2-chloro-5-(1-chloro-3-oxo-phthalan-1-yl)-benzenesulfonic acid amide 

Relevant articles and documents

Synthesis method of chlorthalidone medicine intermediate 2-(3-amino-4-chlorobenzoyl)benzoic acid

The invention discloses a synthesis method of a chlorthalidone medicine intermediate 2-(3-amino-4-chlorobenzoyl)benzoic acid. The method comprises the following steps: reacting 2-(3-nitro-4-chlorobenzoyl)benzoic acid with cuprous chloride and potassium iodide, washing the obtained reaction product, carrying out suction pumping, and dehydrating the reaction product to obtain 2-(3-amino-4-chlorobenzoyl)benzoic acid. The whole reaction time is controlled to be 8h or shorter, and the reaction yield can reach 90% or above. The method provides a new synthesis route, and lays a good foundation for further increase of the reaction yield.

Catalytic liquid-phase reduction of aromatic nitro compounds containing highly reactive functional groups

Improved procedures have been proposed for fast and selective hydrogenation of aromatic nitro compounds with the goal of obtaining practically important amines.

Transfer catalysis between two solids: Application to the reduction of nitroarenes

A wide range of aromatic nitro compounds can be reduced to anilines through the use of a Cr(II)/Mn0 redox couple in the presence of trimethylsilyl chloride [TMSCl, Eq. (1)]. Only 0.25 equivalents of chromium are required to reduce solid-supported nitroarenes (R = solid support); this represents a rare case of transfer catalysis between two solid phases. The reaction is also amenable to solution-phase synthesis (R = OH).