100-07-2

Basic information

• Product Name: 4-Methoxybenzoyl chloride
• Synonyms: 4-methoxy-benzoicacichloride;4-methoxy-benzoylchlorid;Benzoyl chloride, 4-methoxy-;Benzoyl chloride, methoxy-;Benzoyl chloride, p-methoxy-;methoxy-benzoylchlorid;pentaanisoylchloride;p-Methoxybenzoic acid chloride
• CAS NO: 100-07-2
• Molecular Formula: C₈H₇ClO₂
• Molecular Weight: 170.59
• EINECS: 202-816-4
• Product Categories: Aromatic Halides (substituted);Absolute Configuration Determination (Exciton Chirality CD Method);Amino Group Labeling Reagents for HPLC;Analytical Chemistry;Biochemistry;Enantiomer Excess & Absolute Configuration Determination;Exciton Chirality CD Method (for Hydroxyl Groups);HPLC Labeling Reagents;Hydroxyl Group Labeling Reagents for HPLC;Nucleosides, Nucleotides & Related Reagents;Protecting Agents for Hydroxyl and Amino Groups;Protecting Agents, Phosphorylating Agents & Condensing Agents;UV Detection (HPLC Labeling Reagents);Halogenated Heterocycles ,Pyrimidines
• Mol File: 100-07-2.mol
• Article Data: 263

Chemical Properties

• Melting Point: 22 °C(lit.)
• Boiling Point: 262-263 °C(lit.)
• Flash Point: 190 °F
• Appearance: Clear colorless to brown/Liquid After Melting
• Density: 1.260 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.0104mmHg at 25°C
• Refractive Index: n20/D 1.581(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: It reacts in water.
• Sensitive: Moisture Sensitive
• Stability: Stable, but reacts violently with water. Ensure no moisture enters the container in which this material is stored, to prevent pr
• Merck: 14,673
• BRN: 471918
• CAS DataBase Reference: 4-Methoxybenzoyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methoxybenzoyl chloride(100-07-2)
• EPA Substance Registry System: 4-Methoxybenzoyl chloride(100-07-2)

Safety Data

• Hazard Codes: C,F
• Statements: 14-34-67-65-63-48/20-11
• Safety Statements: 26-36/37/39-45-62-16
• RIDADR: UN 1729 8/PG 2
• WGK Germany: 1
• RTECS: CA0270000
• F: 10-21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 100-07-2(Hazardous Substances Data)

Usage

Chemical Properties

4-methoxybenzoyl chloride appears as an amber-colored crystalline solid. Melting point 72 °F. Corrosive to metals and skin. Vapors may cause serious burns to the eyes. Decompose with water or alcohol, soluble in acetone and benzene.

Uses

4-Methoxybenzoyl chloride is used in the synthesis of stilbene and dihydrostilbene derivatives as potential anti-cancer agents. It is also used in the synthesis of coumarin dimers with potential HIV-1 activity.

Application

4-Methoxybenzoyl chloride is one of the reactive acylating agents that can react with carboxylic acids, alcohols and amines to yield respective carboxylic anhydrides, esters and amides.4-Methoxybenzoyl chloride can be used as radical precursor in visible-light photocatalysis to synthesize various heterocyclic compounds.It can be used to synthesize acylphosphine ligands for the rhodium-catalyzed hydrosilylation of alkenes.Incorporation of 4-methoxybenzoyl chloride modified indium tin oxide (ITO) as cathode for the fabrication of organic light-emitting diodes (OLEDs) has been reported.1,3 diketones synthesized from 4-methoxybenzoyl chloride can be used in one pot synthesis of various pyrazole derivatives.It can also be used in the total synthesis of bioactive compounds like echinoside A and salinosporamide A.

Synthesis

4-Methoxybenzoyl chloride is synthesized from the direct chlorination of 4-methoxybenzoic acid by thionyl chloride.

General Description

4-methoxybenzoyl chloride appears as an amber-colored crystalline solid. Melting point 72°F. Corrosive to metals and skin. Vapors may cause serious burns to the eyes.

Air & Water Reactions

Fumes in air. Reacts exothermically with water (including moisture in air or soil) to form hydrochloric acid and insoluble anisic acid [Merck 11th ed. 1989].

Reactivity Profile

ANISOYL CHLORIDE reacts exothermically with bases, including amines. Incompatible with water, strong oxidizing agents, alcohols. Sealed containers held at room temperature may explode, due to slow decomposition that builds up pressure. This situation is more dangerous with heat. May react vigorously or explosively with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].

Hazard

Solutions corrosive to tissue. Explosion risk when in closed containers due to pressure caused by decomposition at room temperature.

Health Hazard

Vapor irritates mucous membranes. Contact of liquid with eyes or skin causes severe irritation. Ingestion causes severe irritation of mouth and stomach.

Fire Hazard

Special Hazards of Combustion Products: Irritating hydrogen chloride fumes may be formed.

Flammability and Explosibility

Notclassified

Chemical Reactivity

Reactivity with Water Reacts slowly to generate hydrogen chloride (hydrochloric acid). The reaction is not hazardous; Reactivity with Common Materials: Corrodes metal slowly; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Flush with water, rinse with sodium bicarbonate or lime solution; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

Safety Profile

Corrosive to skin, eyes, mucous membranes, and other tissue.Evolves HCl by hydrolysis. A storage hazard; can explode spontaneously at room temperature. When heated to decomposition it emits toxic fumes of Cland may explode.

storage

Stored in a closed container can cause an explosion due to the pressure caused by decomposition, should be stored at low temperature (5°C).

InChI:InChI=1/C8H7ClO2/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5H,1H3

Synthetic route

4-methoxybenzoic acid (100-09-4) → 4-methoxy-benzoyl chloride (100-07-2)

Conditions	Yield
With thionyl chloride Reflux;	100%
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 2h; Reflux;	100%
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 35℃; for 1h;	100%

p-methoxybenzotrichloride (3335-36-2) + 4-methoxybenzoic acid (100-09-4) → 4-methoxy-benzoyl chloride (100-07-2)

Conditions	Yield
With iron(III) oxide at 128℃; for 2.3h; Autoclave;	96.7%

carbon monoxide (201230-82-2) + para-iodoanisole (696-62-8) → 4-methoxy-benzoyl chloride (100-07-2)

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0); benzyltriphenylphosphonium chloride In toluene at 110℃; under 38002.6 Torr; for 24h; Glovebox; Autoclave; Inert atmosphere;	95%

para-iodoanisole (696-62-8) + 4-nitro-benzoyl chloride (122-04-3) → p-nitrobenzene iodide (636-98-6) + 4-methoxy-benzoyl chloride (100-07-2)

Conditions	Yield
With (Xantphos)Pd(4-C6H4NO2)(I) In benzene at 90℃; for 20h; Kinetics; Solvent; Reagent/catalyst; Temperature; Sealed tube; Inert atmosphere;	A n/a B 95%

para-iodoanisole (696-62-8) + ortho-toluoyl chloride (933-88-0) → 4-methoxy-benzoyl chloride (100-07-2)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 100℃; for 12h;	89%

1-(4-methoxyphenyl)ethanone (100-06-1) → 4-methoxy-benzoyl chloride (100-07-2)

Conditions	Yield
Stage #1: 1-(4-methoxyphenyl)ethanone With pyridine; disulfur dichloride In chlorobenzene at 20℃; for 2h; Stage #2: With sulfuryl dichloride In chlorobenzene at 20 - 132℃; for 15.5h; Reagent/catalyst; Temperature;	86%
Stage #1: 1-(4-methoxyphenyl)ethanone With pyridine; sulfur monochloride In chlorobenzene at 20℃; Stage #2: With thionyl chloride In chlorobenzene at 20 - 132℃;	63%
With pyridine; disulfur dichloride at 137℃; for 20h; Reagent/catalyst; Temperature; Concentration;	91 %Spectr.

1-bromo-4-methoxy-benzene (104-92-7) + carbon monoxide (201230-82-2) → 4-methoxy-benzoyl chloride (100-07-2)

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; tri-tert-butyl phosphine; benzyltriphenylphosphonium chloride In toluene at 110℃; under 3040.2 Torr; for 24h; Kinetics; Catalytic behavior; Pressure; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; Glovebox; Schlenk technique; Sealed tube;	84%

t-butyl 4-methoxybenzoate (833-79-4) → 4-methoxy-benzoyl chloride (100-07-2)

Conditions	Yield
With phosphorus trichloride In acetonitrile at 80℃; for 3h; Time; Schlenk technique;	76%
With phosphorus trichloride In acetonitrile at 80℃; for 3h; Schlenk technique; Sealed tube;

para-iodoanisole (696-62-8) + aroyl chloride → 4-methoxy-benzoyl chloride (100-07-2)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 100℃; for 12h;	68%

(tris-tertbutylphosphine) p-anisoylpalladium chloride → 4-methoxy-benzoyl chloride (100-07-2)

Conditions	Yield
With carbon monoxide In chloroform-d1 at 20℃; under 3800.26 Torr; for 0.166667h; Pressure; Temperature; Reagent/catalyst; Glovebox;	59%

tetrachloromethane (56-23-5) + tert-butylhypochlorite (507-40-4) + 4-methoxy-benzaldehyde (123-11-5) → 4-methoxy-benzoyl chloride (100-07-2)

1-(p-methoxybenzoyl)-3-methylimidazolium chloride (61166-15-2) → 1-methyl-1H-imidazole (616-47-7) + 4-methoxy-benzoyl chloride (100-07-2)

Conditions	Yield
In dichloromethane at 25℃; Rate constant; Equilibrium constant;

4-methoxybenzoic acid (100-09-4) → benzoyl chloride (98-88-4) + 4-methoxy-benzoyl chloride (100-07-2)

Conditions	Yield
With Benzotrichlorid; iron(III) chloride In benzene at 55℃; Product distribution; Rate constant; Thermodynamic data; ΔE(excit.), var. temp.;

1-(p-methoxybenzoyl)-3-methoxymethylimidazolium chloride (93342-84-8) → 4-methoxy-benzoyl chloride (100-07-2) + 1-(methoxymethyl)imidazole (20075-26-7)

Conditions	Yield
In dichloromethane at 25℃; Rate constant; Equilibrium constant;

1-(p-methoxybenzoyl)-3-benzylimidazolium chloride (93342-85-9) → 1-benzylimidazole (4238-71-5) + 4-methoxy-benzoyl chloride (100-07-2)

Conditions	Yield
In dichloromethane at 25℃; Rate constant; Equilibrium constant;

4-methoxybenzoyl radical (2652-68-8) → 4-methoxy-benzoyl chloride (100-07-2)

Conditions	Yield
With tetrachloromethane In various solvent(s) at 22.9℃; Rate constant;

(Z)-2-Butene (590-18-1) + p-toluenesulfonyl chloride (98-59-9) + benzyl isothiocyanate (3173-56-6) → 4-methoxy-benzoyl chloride (100-07-2) + C28H31NO8S2

Conditions	Yield
Yield given. Multistep reaction. Yields of byproduct given;

thionyl chloride (7719-09-7) + 4-methoxybenzoic acid (100-09-4) → 4-methoxy-benzoyl chloride (100-07-2)

phosphorus pentachloride (10026-13-8, 874483-75-7) + 4-methoxybenzoic acid (100-09-4) → 4-methoxy-benzoyl chloride (100-07-2)

oxalyl dichloride (79-37-8) + sodium anisate → 4-methoxy-benzoyl chloride (100-07-2)

Conditions	Yield
With benzene

phosphorus pentachloride (10026-13-8, 874483-75-7) + 1,2-bis(4-methoxyphenyl)-1,2-ethanediol (4464-76-0, 39090-28-3, 39090-30-7, 42565-21-9, 66768-20-5, 122798-27-0) → 4-methoxy-benzoyl chloride (100-07-2)

Conditions	Yield
hydroanisoin;

4-hydroxy-benzoic acid (99-96-7) → 4-methoxy-benzoyl chloride (100-07-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: KOH / ethanol / Heating 2: SOCl2 View Scheme
Multi-step reaction with 2 steps 1: KOH / ethanol 2: SOCl2 View Scheme
Multi-step reaction with 2 steps 1.1: potassium hydroxide 1.2: Reflux 2.1: thionyl chloride / Reflux View Scheme

4-hydroxy-benzoic acid (99-96-7) + Nα-Fmoc-Nim-tert-butyloxycarbonyl-L-tryptophan 4-hydroxymethylphenoxy resin → 4-methoxy-benzoyl chloride (100-07-2) + aminoacyl chlorotrityl resin

Conditions	Yield
Multi-step reaction with 2 steps 1: KOH / ethanol 2: SOCl2 View Scheme
Multi-step reaction with 2 steps 1: alcohol; KOH 2: SOCl2 View Scheme

Ethyl 4-hydroxybenzoate (120-47-8) + (+-)-methylphosphonic acid ethyl ester chloride → 4-methoxy-benzoyl chloride (100-07-2) + aminoacyl chlorotrityl resin

Conditions	Yield
Multi-step reaction with 3 steps 1: NaOEt / 3 h / Heating 2: KOH / ethanol 3: SOCl2 View Scheme

ethyl 4-methoxybenzoate (94-30-4) → 4-methoxy-benzoyl chloride (100-07-2) + aminoacyl chlorotrityl resin

Conditions	Yield
Multi-step reaction with 2 steps 1: KOH / ethanol 2: SOCl2 View Scheme

4-hydroxy-benzoic acid (99-96-7) + source of vinyl group → 4-methoxy-benzoyl chloride (100-07-2) + aminoacyl chlorotrityl resin

Conditions	Yield
Multi-step reaction with 4 steps 1: conc. H2SO4 / Heating 2: NaOEt / 3 h / Heating 3: KOH / ethanol 4: SOCl2 View Scheme

4-methoxyphenylacetamide (3424-93-9) → 4-methoxy-benzoyl chloride (100-07-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 93 percent / TiCl4 / dioxane; H2O / 19 h / Heating 2: oxalyl chloride / CH2Cl2 / 0 - 20 °C View Scheme

4-hydroxy-benzoic acid (99-96-7) + aqueous solution of pH 4,3 → 4-methoxy-benzoyl chloride (100-07-2) + hydrogen persulfide

Conditions	Yield
Multi-step reaction with 2 steps 2: thionyl chloride / 2 h / Heating View Scheme

methyl 4-methoxybenzoate (121-98-2) → 4-methoxy-benzoyl chloride (100-07-2) + hydrogen persulfide

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / KOH / methanol; H2O / 4 h / Heating 2: thionyl chloride / 1 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 6percent aq. KOH 2: SOCl2 View Scheme

isobutylamine (78-81-9) + 4-methoxy-benzoyl chloride (100-07-2) → N-isobutyl-4-methoxybenzamide (7464-51-9)

Conditions	Yield
With triethylamine In benzene	100%

1,12-Diaminododecane (2783-17-7) + 4-methoxy-benzoyl chloride (100-07-2) → C28H40N2O4 (27890-95-5)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2h; Inert atmosphere;	100%
With potassium hydroxide In 1,2-dichloro-ethane
With potassium hydroxide

4-methoxy-benzoyl chloride (100-07-2) + tert-butylamine (75-64-9) → N-tert-butyl-4-methoxybenzamide (19486-73-8)

Conditions	Yield
With sodium hydroxide In dichloromethane	100%
With dmap; sodium hydroxide In dichloromethane at 0 - 20℃;	100%
In tetrahydrofuran at 0℃;	86%

diphenylphosphinous acid methyl ester (4020-99-9) + 4-methoxy-benzoyl chloride (100-07-2) → (diphenylphosphoryl)(4-methoxyphenyl)methanone (87361-23-7)

Conditions	Yield
at 25℃;	100%
In toluene at 60℃; for 2h; Michaelis-Arbuzov reaction;	77%

N-methoxylamine hydrochloride (593-56-6) + 4-methoxy-benzoyl chloride (100-07-2) → N-methoxy-4-methoxylbenzamide (24056-08-4)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 2h;	100%
With sodium carbonate In water; benzene at 20℃; for 18h; Cooling;	98%
With potassium carbonate In water; ethyl acetate at 0 - 20℃;	98%

methyl 3,4-dihydro-1-methyl-β-carboline-3-carboxylate (51372-96-4) + 4-methoxy-benzoyl chloride (100-07-2) → methyl 2-(4-methoxybenzoyl)-2,3,4,9-tetrahydro-1-methylene-1H-pyrido<3,4-b>indole-3-carboxylate (84576-15-8)

Conditions	Yield
With triethylamine In benzene 1.) R.T., 2.) 50 deg C, 2 h.;	100%

4-methoxy-benzoyl chloride (100-07-2) + diisopropylamine (108-18-9) → N,N-diisopropyl-4-methoxybenzamide (79606-43-2)

Conditions	Yield
With triethylamine In dichloromethane at 50℃; for 18h;	100%
With triethylamine In dichloromethane at 0 - 20℃; for 12h;	91%
With triethylamine In dichloromethane at 20℃; for 4h; Inert atmosphere;	81%

4-methoxy-benzoyl chloride (100-07-2) → 4-methoxybenzohydroxamic acid (10507-69-4)

Conditions	Yield
With hydroxylamine hydrochloride; sodium hydrogencarbonate In water; ethyl acetate at 20℃; for 0.0833333h;	100%
With hydroxylamine hydrochloride; sodium hydrogencarbonate In water; ethyl acetate at 20℃; for 0.0833333h;	95%
With hydroxylamine hydrochloride; potassium carbonate In water; ethyl acetate at 0 - 20℃; for 16h;	56%

3-amino-2-methyl-4-oxoquinazoline (1898-06-2) + 4-methoxy-benzoyl chloride (100-07-2) → 4-methoxy-N-(2-methyl-4-oxo-4H-quinazolin-3-yl)-benzamide (6761-15-5)

Conditions	Yield
With pyridine In benzene for 2h; Heating;	100%

4-methoxy-benzoyl chloride (100-07-2) + Potassium; 2-triisopropylsilanyloxy-butane-1-thiolate → 4-Methoxy-thiobenzoic acid S-(2-triisopropylsilanyloxy-butyl) ester

Conditions	Yield
In tetrahydrofuran at 0℃; for 2h;	100%

4-methoxy-benzoyl chloride (100-07-2) + 2-phenyl-2-propylamine (585-32-0) → 4-methoxy-N-(1-methyl-1-phenylethyl)benzamide (454479-63-1)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 18h;	100%
With triethylamine In dichloromethane for 12h;	87%
In tetrahydrofuran at 0℃;	84%
With triethylamine In dichloromethane Acylation;

4-methoxy-benzoyl chloride (100-07-2) + 1-(2,5-Dichlorophenyl)-2,2-bis(methylsulfanyl)ethanone (171897-89-5) → 4-methoxy-benzoic acid 1-(2,5-dichloro-phenyl)-2,2-bis-methylsulfanyl-vinyl ester

Conditions	Yield
Stage #1: 1-(2,5-Dichlorophenyl)-2,2-bis(methylsulfanyl)ethanone With sodium hydride In tetrahydrofuran Metallation; Stage #2: 4-methoxy-benzoyl chloride In tetrahydrofuran at 20℃; for 0.5h; Acylation;	100%

N-(p-methoxybenzyl)-N-tert-butylamine (22675-83-8) + 4-methoxy-benzoyl chloride (100-07-2) → N-tert-butyl-4-methoxy-N-(4-methoxy-benzyl)-benzamide (335596-11-7)

Conditions	Yield
With sodium hydroxide In dichloromethane for 24h;	100%

4-methoxy-benzoyl chloride (100-07-2) + N-tert-butylbenzylamine (3378-72-1) → N-benzyl-N-tert-butyl-4-methoxy-benzamide (133587-81-2)

Conditions	Yield
With sodium hydroxide In dichloromethane for 24h;	100%

Upstream product

• 100-09-4 Anisic acid 
• 7719-09-7 Thionyl chloride 

Downstream Products

• 66778-36-7 BENZAMIDE, 4-METHOXY-N-[2-[2-(1-METHYL-2-PIPERIDINYL)ETHYL]PHENYL]- 
• 3076-87-7 N,N'-(9,10-dihydro-4,8-dihydroxy-9,10-dioxoanthracene-1,5-diyl)bis[4-methoxybenzamide] 
• 4160-63-8 2-(4-METHOXYBENZOYL)THIOPHENE 
• 31430-18-9 NOCODAZOLE 
• 1951-25-3 Amiodarone 
• 66938-50-9 (4-Methoxy-3-nitrophenyl)-(thiophen-2-yl)methanone ,98% 
• 72432-10-1 Aniracetam 

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