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

2-(3-Amino-4-chlorobenzoyl)benzoic Acid is a useful synthetic intermediate. It is used to prepare protein kinase C phosphorylates synthetic fluorescent reporter.

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

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

Downstream Products

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

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.

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).