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

General Description

4-chloro-1'-(4-methoxyphenyl)benzohydrazide is a chemical compound with a molecular formula of C14H13ClN2O2. It is a hydrazide derivative of benzoic acid and contains a chloro group and a methoxyphenyl group attached to the benzene ring. 4-chloro-1'-(4-methoxyphenyl)benzohydrazide has been studied for its potential biological activities, including its anti-inflammatory and analgesic properties. It has also been investigated for its potential use as a corrosion inhibitor and as a precursor for the synthesis of other organic compounds. Overall, 4-chloro-1'-(4-methoxyphenyl)benzohydrazide is a versatile chemical that has potential applications in various fields.

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