16390-07-1

Basic information

• Product Name: 4-chloro-1'-(4-methoxyphenyl)benzohydrazide
• Synonyms: 4-chloro-1'-(4-methoxyphenyl)benzohydrazide;N-(P-CHLOROBENZOYL)-N-(P-METHOXYPHENYL)HYDRAZINE;N-(P-DHLOROBENZOYL)-N-(P-METHOXYPHENYL)HYDRAZINE;4-Chlorobenzoic acid 1-(4-methoxyphenyl)hydrazide;4-Chloro-N1-(4-methoxyphenyl)benzohydrazide;N-(4-Methoxyphenyl)-4-chlorobenzohydrazide;Einecs 240-441-8;Benzoic acid, 4-chloro-, 1-(4-Methoxyphenyl)hydrazide
• CAS NO: 16390-07-1
• Molecular Formula: C₁₄H₁₃ClN₂O₂
• Molecular Weight: 276.71822
• EINECS: 240-441-8
• Mol File: 16390-07-1.mol
• Article Data: 0

Chemical Properties

• Boiling Point: 391.7°C at 760 mmHg
• Flash Point: 190.7°C
• Appearance: /
• Density: 1.298g/cm³
• Vapor Pressure: 2.42E-06mmHg at 25°C
• Refractive Index: 1.631
• PKA: 1.28±0.11(Predicted)
• CAS DataBase Reference: 4-chloro-1'-(4-methoxyphenyl)benzohydrazide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chloro-1'-(4-methoxyphenyl)benzohydrazide(16390-07-1)
• EPA Substance Registry System: 4-chloro-1'-(4-methoxyphenyl)benzohydrazide(16390-07-1)

Safety Data

• Hazardous Substances Data: 16390-07-1(Hazardous Substances Data)

Usage

Description

4-chloro-1'-(4-methoxyphenyl)benzohydrazide is a hydrazide derivative of benzoic acid with a molecular formula of C14H13ClN2O2. It features a chloro group and a methoxyphenyl group attached to the benzene ring, endowing it with potential biological activities and a wide range of applications.

Uses

Used in Pharmaceutical Industry:
4-chloro-1'-(4-methoxyphenyl)benzohydrazide is used as a pharmaceutical agent for its anti-inflammatory and analgesic properties, offering potential therapeutic benefits in managing pain and inflammation.
Used in Chemical Industry:
4-chloro-1'-(4-methoxyphenyl)benzohydrazide is used as a corrosion inhibitor, providing protection against metal corrosion in various industrial applications, such as in the manufacturing of pipelines, storage tanks, and other metal structures.
Used in Organic Synthesis:
4-chloro-1'-(4-methoxyphenyl)benzohydrazide is used as a precursor in the synthesis of other organic compounds, contributing to the development of new chemical entities with diverse applications in various fields.
Overall, 4-chloro-1'-(4-methoxyphenyl)benzohydrazide is a versatile chemical compound with potential applications in the pharmaceutical, chemical, and organic synthesis industries, as well as in other areas where its unique properties can be harnessed for beneficial purposes.

InChI:InChI=1/C14H13ClN2O2/c1-19-13-8-6-12(7-9-13)16-17-14(18)10-2-4-11(15)5-3-10/h2-9,16H,1H3,(H,17,18)

Synthetic route

N1-(4-chlorobenzoyl)-4-methoxyphenylhydrazine (16390-07-1) + 1-{4-[3-(4-phenyl-piperazin-1-yl)-propoxy]-phenyl}-propan-1-one (36115-62-5) → (4-Chloro-phenyl)-(5-methoxy-3-methyl-2-{4-[3-(4-phenyl-piperazin-1-yl)-propoxy]-phenyl}-indol-1-yl)-methanone; hydrochloride (134858-69-8)

Conditions	Yield
With hydrogenchloride; acetic acid at 80℃; for 6h;	83%

5-methyl-2-furanone (591-12-8) + N1-(4-chlorobenzoyl)-4-methoxyphenylhydrazine (16390-07-1) → 5-Methoxy-2-methylindole-3-acetic acid (2882-15-7) + [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid (53-86-1)

Conditions	Yield
With sulfuric acid In acetonitrile for 24h; Fischer indole reaction; Heating;	A n/a B 65%

N1-(4-chlorobenzoyl)-4-methoxyphenylhydrazine (16390-07-1) + 1-<4-(2-carboxyethyl)phenoxy>-3-1-(N4-phenyl-piperazinyl)>propane (134858-58-5) → (1-(4-Chloro-benzoyl)-5-methoxy-2-{4-[3-(4-phenyl-piperazin-1-yl)-propoxy]-phenyl}-1H-indol-3-yl)-acetic acid; hydrochloride (134858-68-7)

Conditions	Yield
With hydrogenchloride; acetic acid at 80℃; for 6h;	56%

N1-(4-chlorobenzoyl)-4-methoxyphenylhydrazine (16390-07-1) + 1-{4-[3-(4-phenyl-piperazin-1-yl)-propoxy]-phenyl}-ethanone (66118-10-3) → 1-(4-chlorobenzoyl)-6-methoxy-2-<4-<3-N1-(N4-phenylpiperazinyl)propoxy>phenyl>indole dihydrochloride (134858-70-1)

Conditions	Yield
With hydrogenchloride; acetic acid at 80℃; for 6h;	46%

levulinic-4-14C acid (70481-61-7) + N1-(4-chlorobenzoyl)-4-methoxyphenylhydrazine (16390-07-1) → 2-<14C>-Indometacin (135581-00-9)

Conditions	Yield

2-(3-oxobutyl)benzoic acid (7114-76-3) + N1-(4-chlorobenzoyl)-4-methoxyphenylhydrazine (16390-07-1) → 2-[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-ylmethyl]-benzoic acid

Conditions	Yield
With phosphoric acid In toluene Fischer indole synthesis; Heating;

N1-(4-chlorobenzoyl)-4-methoxyphenylhydrazine (16390-07-1) + 3-(3'-oxobutyl)benzoic acid (99450-00-7) → 3-[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-ylmethyl]-benzoic acid

Conditions	Yield
With phosphoric acid In toluene Fischer indole synthesis; Heating;

N1-(4-chlorobenzoyl)-4-methoxyphenylhydrazine (16390-07-1) + 4-(4-carboxyphenyl)butan-2-one (74248-66-1) → 4-[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-1H-indol-3-ylmethyl]-benzoic acid

Conditions	Yield
With phosphoric acid In toluene Fischer indole synthesis; Heating;

N1-(4-chlorobenzoyl)-4-methoxyphenylhydrazine (16390-07-1) + [3-(3-oxo-butyl)-phenoxy]-acetic acid → 2-(3-{ [1-(4-Chlorobenzoyl)-2-Methyl-5-(methoxy)-1H-indol-3-yl]methyl}phenoxy)acetic acid

Conditions	Yield
With phosphoric acid In toluene Fischer indole synthesis; Heating;

N1-(4-chlorobenzoyl)-4-methoxyphenylhydrazine (16390-07-1) + [2-(3-oxo-butyl)-phenoxy]-acetic acid → 2-(2-{[1-(4-Chlorobenzoyl)-2-methyl-5-(methoxy)-1H-indol-3-yl]methyl }phenoxy)acetic acid

Conditions	Yield
With phosphoric acid In toluene Fischer indole synthesis; Heating;

N1-(4-chlorobenzoyl)-4-methoxyphenylhydrazine (16390-07-1) + 2-[4-(3-OXOBUTYL)PHENOXY]ACETIC ACID (926206-19-1) → 2-(4-{ [1-(4-Chlorobenzoyl)-2-methyl-5-(methoxy)-1H-indol-3-yl]methyl }phenoxy)acetic acid

Conditions	Yield
With phosphoric acid In toluene Fischer indole synthesis; Heating;

4-(2-hydroxyphenyl)butan-2-one (61844-32-4) + N1-(4-chlorobenzoyl)-4-methoxyphenylhydrazine (16390-07-1) + Br-CH(Me)-COOR → 2-(2-{ [1-(4-Chlorobenzoyl)-2-methyl-5-(methoxy)-1H-indol-3-yl]methyl}phenoxy)propanoic acid

Conditions	Yield
Stage #1: 4-(2-hydroxyphenyl)butan-2-one; Br-CH(Me)-COOR With potassium carbonate In N,N-dimethyl-formamide Stage #2: N1-(4-chlorobenzoyl)-4-methoxyphenylhydrazine With phosphoric acid In toluene Fischer indole synthesis; Heating; Stage #3: hydrolysis;

4-(3-hydroxyphenyl)-2-butanone (56363-73-6) + N1-(4-chlorobenzoyl)-4-methoxyphenylhydrazine (16390-07-1) + Br-CH(Me)-COOR → 2-(3-{ [ 1-(4-Chlorobenzoyl)-2-methyl-5-(methoxy)-1H-indol-3-yl]methyl }phenoxy)propanoic acid

Conditions	Yield
Stage #1: 4-(3-hydroxyphenyl)butan-2-one; Br-CH(Me)-COOR With potassium carbonate In N,N-dimethyl-formamide Stage #2: N1-(4-chlorobenzoyl)-4-methoxyphenylhydrazine With phosphoric acid In toluene Fischer indole synthesis; Heating; Stage #3: hydrolysis;

N1-(4-chlorobenzoyl)-4-methoxyphenylhydrazine (16390-07-1) + 4-(4-hydroxyphenyl)-2-oxobutane (5471-51-2) + Br-CH(Me)-COOR

Conditions	Yield
Stage #1: 4-(4-hydroxyphenyl)-2-oxobutane; Br-CH(Me)-COOR With potassium carbonate In N,N-dimethyl-formamide Stage #2: N1-(4-chlorobenzoyl)-4-methoxyphenylhydrazine With phosphoric acid In toluene Fischer indole synthesis; Heating; Stage #3: hydrolysis;

4-(2-hydroxyphenyl)butan-2-one (61844-32-4) + N1-(4-chlorobenzoyl)-4-methoxyphenylhydrazine (16390-07-1) + Br-C(Me)2-COOR → 2-(2-{ [1-(4-Chlorobenzoyl)-2-methyl-5-(methoxy)-1H-indol-3-yl]methyl }phenoxy)-2-methylpropanoic acid

Conditions	Yield
Stage #1: 4-(2-hydroxyphenyl)butan-2-one; Br-C(Me)2-COOR With potassium carbonate In N,N-dimethyl-formamide Stage #2: N1-(4-chlorobenzoyl)-4-methoxyphenylhydrazine With phosphoric acid In toluene Fischer indole synthesis; Heating; Stage #3: hydrolysis;

4-(3-hydroxyphenyl)-2-butanone (56363-73-6) + N1-(4-chlorobenzoyl)-4-methoxyphenylhydrazine (16390-07-1) + Br-C(Me)2-COOR → 2-(3-{ [1-(4-Chlorobenzoyl)-2-methyl-5-(methoxy)-1H-indol-3-yl]methyl }phenoxy)-2-methylpropanoic acid

Conditions	Yield
Stage #1: 4-(3-hydroxyphenyl)butan-2-one; Br-C(Me)2-COOR With potassium carbonate In N,N-dimethyl-formamide Stage #2: N1-(4-chlorobenzoyl)-4-methoxyphenylhydrazine With phosphoric acid In toluene Fischer indole synthesis; Heating; Stage #3: hydrolysis;

N1-(4-chlorobenzoyl)-4-methoxyphenylhydrazine (16390-07-1) + 4-(4-hydroxyphenyl)-2-oxobutane (5471-51-2) + Br-C(Me)2-COOR → 2-(4-{ [1-(4-Chlorobenzoyl)-2-methyl-5-(methoxy)-1H-indol-3-yl]methyl }phenoxy)-2-methylpropanoic acid

Conditions	Yield
Stage #1: 4-(4-hydroxyphenyl)-2-oxobutane; Br-C(Me)2-COOR With potassium carbonate In N,N-dimethyl-formamide Stage #2: N1-(4-chlorobenzoyl)-4-methoxyphenylhydrazine With phosphoric acid In toluene Fischer indole synthesis; Heating; Stage #3: hydrolysis;

nickel(II) chloride hexahydrate + N1-(4-chlorobenzoyl)-4-methoxyphenylhydrazine (16390-07-1) → Ni(C14H13N2O2Cl)2Cl2 (234089-03-3)

Conditions	Yield
In methanol stiring (30 min, room temp.); soln. standing (room temp., 24 h), washing (acetone), recrystn. (methanol); elem. anal.;

copper(II) choride dihydrate + N1-(4-chlorobenzoyl)-4-methoxyphenylhydrazine (16390-07-1) → Cu(C14H13N2O2Cl)2Cl2 (234089-01-1)

Conditions	Yield
In methanol stiring (30 min, room temp.); soln. standing (room temp., 24 h), washing (acetone), recrystn. (methanol); elem. anal.;

iron(III) chloride hexahydrate + N1-(4-chlorobenzoyl)-4-methoxyphenylhydrazine (16390-07-1) → Fe(C14H13N2O2Cl)3(3+)*3Cl(1-) = [Fe(C14H13N2O2Cl)3]Cl3

Conditions	Yield
In methanol stiring (30 min, room temp.); soln. standing (room temp., 24 h), washing (acetone), recrystn. (methanol); elem. anal.;

chromium chloride hexahydrate + N1-(4-chlorobenzoyl)-4-methoxyphenylhydrazine (16390-07-1) → Cr(C14H13N2O2Cl)3(3+)*3Cl(1-) = [Cr(C14H13N2O2Cl)3]Cl3

Conditions	Yield
In methanol stiring (30 min, room temp.); soln. standing (room temp., 24 h), washing (acetone), recrystn. (methanol); elem. anal.;

manganese(II) chloride tetrahydrate + N1-(4-chlorobenzoyl)-4-methoxyphenylhydrazine (16390-07-1) → Mn(C14H13N2O2Cl)2Cl2 (234089-02-2)

Conditions	Yield
In methanol stiring (30 min, room temp.); soln. standing (room temp., 24 h), washing (acetone), recrystn. (methanol); elem. anal.;

cobalt(II) chloride hexahydrate + N1-(4-chlorobenzoyl)-4-methoxyphenylhydrazine (16390-07-1) → Co(C14H13N2O2Cl)2Cl2 (257297-50-0)

Conditions	Yield
In methanol stiring (30 min, room temp.); soln. standing (room temp., 24 h), washing (acetone), recrystn. (methanol); elem. anal.;

Downstream Products

• 257297-50-0 Co(C₁₄H₁₃N₂O₂Cl)2Cl₂ 
• 2882-15-7 5-Methoxy-2-methylindole-3-acetic acid 
• 53-86-1 [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid 
• 134858-70-1 1-(4-chlorobenzoyl)-6-methoxy-2-<4-<3-N¹-(N⁴-phenylpiperazinyl)propoxy>phenyl>indole dihydrochloride 
• 134858-68-7 (1-(4-Chloro-benzoyl)-5-methoxy-2-{4-[3-(4-phenyl-piperazin-1-yl)-propoxy]-phenyl}-1H-indol-3-yl)-acetic acid; hydrochloride 
• 135581-00-9 2-<14C>-Indometacin