116412-83-0

Basic information

• Product Name: 4-Chloro-3,4'-DimethoxyBenzophenone
• Synonyms: 4-CHLORO-(3,4-DIMETHOXY)-BENZOPHENONE 98+%;4-Chloro-3',4'-dimethoxybenzophenone
• CAS NO: 116412-83-0
• Molecular Formula: C₁₅H₁₃ClO₃
• Molecular Weight: 276.71
• EINECS: 404-610-1
• Product Categories: Naphthyridine,Quinoline
• Mol File: 116412-83-0.mol
• Article Data: 13

Chemical Properties

• Melting Point: 111-112 °C(Solv: ethanol (64-17-5))
• Boiling Point: 414.5°Cat760mmHg
• Flash Point: 167.2°C
• Appearance: /
• Density: 1.216g/cm³
• Storage Temp.: 2-8°C
• Solubility: Chloroform; Dichloromethane; DMSO; Ethyl Acetate; Methanol
• CAS DataBase Reference: 4-Chloro-3,4'-DimethoxyBenzophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-3,4'-DimethoxyBenzophenone(116412-83-0)
• EPA Substance Registry System: 4-Chloro-3,4'-DimethoxyBenzophenone(116412-83-0)

Safety Data

• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61
• Hazardous Substances Data: 116412-83-0(Hazardous Substances Data)

Usage

Uses

4-Chloro-3'',4''-dimethoxybenzophenone is an intermedioate in the synthesis of Dimethomorph-d8 (D460532), a labelled agricultural fungicide.

Synthetic route

1,2-dimethoxybenzene (91-16-7) + 4-chloro-benzoyl chloride (122-01-0) → FeCl3 + 4-chloro-3',4'-dimethoxy benzophenone (116412-83-0)

Conditions	Yield
	A n/a B 93%

1,2-dimethoxybenzene (91-16-7) + para-chlorobenzoic acid (74-11-3) → 4-chloro-3',4'-dimethoxy benzophenone (116412-83-0)

Conditions	Yield
With boron trifluoride diethyl etherate at 80 - 90℃; for 0.05h; Microwave irradiation; chemoselective reaction;	89%

3,4-dimethoxy-benzaldehyde (120-14-9) + (4-chlorphenyl)magnesium bromide (873-77-8) → 4-chloro-3',4'-dimethoxy benzophenone (116412-83-0)

Conditions	Yield
Stage #1: 3,4-dimethoxy-benzaldehyde; (4-chlorphenyl)magnesium bromide In tetrahydrofuran Stage #2: With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene In dichloromethane	86%

1,2-dimethoxybenzene (91-16-7) + 4-chloro-benzoyl chloride (122-01-0) + 1,1,2,2-tetrachloroethane (79-34-5) → 4-chloro-3',4'-dimethoxy benzophenone (116412-83-0)

Conditions	Yield
With FeCl3; graphite	84.3%
With FeCl3; graphite	84.3%
graphite	81.3%

1,2-dimethoxybenzene (91-16-7) + 4-chlorotrichloromethylbenzene (5216-25-1) + 1,1,2,2-tetrachloroethane (79-34-5) → 4-chloro-3',4'-dimethoxy benzophenone (116412-83-0)

Conditions	Yield
graphite In water	79.5%

1,2-dimethoxybenzene (91-16-7) + 4-chloro-benzoyl chloride (122-01-0) → 4-chloro-3',4'-dimethoxy benzophenone (116412-83-0)

Conditions	Yield
With Cl4Fe(1-)*C9H7N3O2*H(1+) In neat (no solvent) at 100℃; for 3h; Friedel-Crafts Acylation; Inert atmosphere;	70%
With aluminium trichloride In dichloromethane for 0.5h; Friedel-Crafts reaction;	53%
With aluminium trichloride In benzene at 55 - 60℃; for 2.5h; Friedel-Crafts reaction;

para-chlorobenzoic acid (74-11-3) → 4-chloro-3',4'-dimethoxy benzophenone (116412-83-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 2 h / 20 °C / Reflux 2: aluminum (III) chloride / dichloromethane / 2 h / 0 °C / Reflux View Scheme

benzene-1,2-diol (120-80-9) → 4-chloro-3',4'-dimethoxy benzophenone (116412-83-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydroxide / water / 1.33 h / 10 - 15 °C / Inert atmosphere; Large scale 1.2: 4.7 h / 20 - 50 °C / Inert atmosphere; Large scale 2.1: iron(III) chloride / hexane / 2.8 h / 120 °C / Inert atmosphere; Large scale View Scheme

1,2-dimethoxybenzene (91-16-7) + para-chloroacetophenone (99-91-2) → 4-chloro-3',4'-dimethoxy benzophenone (116412-83-0)

Conditions	Yield
With iron(III) chloride In hexane at 120℃; for 2.8h; Temperature; Inert atmosphere; Large scale;

Methyltriphenylphosphonium bromide (1779-49-3) + 4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → C16H15ClO2

Conditions	Yield
With sodium hydride	89%

4-acetylmorpholine (1696-20-4) + tert-Amyl alcohol (75-85-4) + sodium tert-pentoxide (14593-46-5) + 4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → dimethomorph

Conditions	Yield
With carbon dioxide In 5,5-dimethyl-1,3-cyclohexadiene; di-isopropyl ether; paraffin oil	82.2%

ethylene glycol (107-21-1) + 4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → 2-(4-chloro-phenyl)-2-(3,4-dimethoxy-phenyl)-[1,3]dioxolane (812685-05-5)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 40h; Heating;	82%

4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → (4-chlorophenyl)-(4,5-dimethoxy-2-nitrophenyl)methanone (681469-99-8)

Conditions	Yield
With nitric acid; acetic acid at 0 - 20℃; for 0.5h;	77%
With nitric acid; acetic acid

4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → 4-[3-(4-chlorophenyl)-5,6-dimethoxy-1H-2-indolyl]-2-butanone

Conditions	Yield
Multi-step reaction with 7 steps 1: 77 percent / HNO3; AcOH / 0.5 h / 0 - 20 °C 2: 67 percent / Fe; AcOH / H2O; ethyl acetate / 6 h / Heating 3: 78 percent / pyridine / 1 h / 20 °C 4: 86 percent / NaBH4 / ethanol / Heating 5: 76 percent / p-TsOH / CH2Cl2 / Heating 6: 81 percent / HCl / ethanol / Heating 7: 91 percent / KOH / methanol / 4 h / Heating View Scheme

4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → 2-[4-chlorophenyl(hydroxy)methyl]-4,5-dimethoxy-1-(4-methylphenylsulfonamido)benzene (924635-48-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 77 percent / HNO3; AcOH / 0.5 h / 0 - 20 °C 2: 67 percent / Fe; AcOH / H2O; ethyl acetate / 6 h / Heating 3: 78 percent / pyridine / 1 h / 20 °C 4: 86 percent / NaBH4 / ethanol / Heating View Scheme

4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → 2-(4-chlorobenzoyl)-4,5-dimethoxy-1-(4-methylphenylsufonamido)benzene (886493-87-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 77 percent / HNO3; AcOH / 0.5 h / 0 - 20 °C 2: 67 percent / Fe; AcOH / H2O; ethyl acetate / 6 h / Heating 3: 78 percent / pyridine / 1 h / 20 °C View Scheme

4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → 4-methyl-N-{2-[(4-chlorophenyl)(5-methylfuran-2-yl)methyl]-4,5-dimethoxyphenyl}benzenesulfonamide (924635-54-1)

Conditions	Yield
Multi-step reaction with 5 steps 1: 77 percent / HNO3; AcOH / 0.5 h / 0 - 20 °C 2: 67 percent / Fe; AcOH / H2O; ethyl acetate / 6 h / Heating 3: 78 percent / pyridine / 1 h / 20 °C 4: 86 percent / NaBH4 / ethanol / Heating 5: 76 percent / p-TsOH / CH2Cl2 / Heating View Scheme

4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → 4-[3-(4-chlorophenyl)-5,6-dimethoxy-1-(4-methylphenylsulfonyl)-1H-2-indolyl]-2-butanone (920457-61-0)

Conditions	Yield
Multi-step reaction with 6 steps 1: 77 percent / HNO3; AcOH / 0.5 h / 0 - 20 °C 2: 67 percent / Fe; AcOH / H2O; ethyl acetate / 6 h / Heating 3: 78 percent / pyridine / 1 h / 20 °C 4: 86 percent / NaBH4 / ethanol / Heating 5: 76 percent / p-TsOH / CH2Cl2 / Heating 6: 81 percent / HCl / ethanol / Heating View Scheme

4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → (2-amino-4,5-dimethoxyphenyl)-(4-chlorophenyl)methanone (886494-44-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 77 percent / HNO3; AcOH / 0.5 h / 0 - 20 °C 2: 67 percent / Fe; AcOH / H2O; ethyl acetate / 6 h / Heating View Scheme

4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → 3-chloro-6-(3,4-dimethoxybenzoyl)benzoic acid

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 82 percent / p-toluenesulfonic acid / toluene / 40 h / Heating 2.1: butyllithium / hexane; tetrahydrofuran / 2 h / -20 °C 2.2: tetrahydrofuran; hexane / 3 h 3.1: 1.35 g / aq. hydrochloric acid / 4 h / Heating View Scheme

4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → 5-chloro-2-[2-(3,4-dimethoxy-phenyl)-[1,3]dioxolan-2-yl]-benzenesulfonyl chloride

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 82 percent / p-toluenesulfonic acid / toluene / 40 h / Heating 2.1: butyllithium / hexane; tetrahydrofuran / 2 h / -20 °C 2.2: sulfur dioxide / tetrahydrofuran; hexane / 12 h / 20 °C 3.1: sulfuryl chloride / hexane / 0.5 h / 0 °C View Scheme

4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → 5-chloro-2-[2-(3,4-dimethoxy-phenyl)-[1,3]dioxolan-2-yl]-benzoic acid (1027937-58-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 82 percent / p-toluenesulfonic acid / toluene / 40 h / Heating 2.1: butyllithium / hexane; tetrahydrofuran / 2 h / -20 °C 2.2: tetrahydrofuran; hexane / 3 h View Scheme

4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → lithium; 5-chloro-2-[2-(3,4-dimethoxy-phenyl)-[1,3]dioxolan-2-yl]-benzenesulfinate

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 82 percent / p-toluenesulfonic acid / toluene / 40 h / Heating 2.1: butyllithium / hexane; tetrahydrofuran / 2 h / -20 °C 2.2: sulfur dioxide / tetrahydrofuran; hexane / 12 h / 20 °C View Scheme

4-acetylmorpholine (1696-20-4) + sodium tert-pentoxide (14593-46-5) + 4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → dimethomorph

Conditions	Yield
In di-isopropyl ether; toluene

tert-butyl alcohol (75-65-0) + 4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → dimethomorph

Conditions	Yield
In toluene; paraffin oil

4-acetylmorpholine (1696-20-4) + 4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → dimethomorph

Conditions	Yield
With potassium hydroxide In tetrahydrofuran

4-acetylmorpholine (1696-20-4) + p-Tolylaceton (2096-86-8) + 4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → 3-(4-chlorophenyl)-3-(3,4-dimethoxyphenyl)-3-hydroxy-1-morpholinopropan-1-one + dimethomorph

Conditions	Yield
With potassium hydroxide In water; toluene

4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → 4-chloro-3',4'-dimethoxydiphenylmethane (1239703-27-5)

Conditions	Yield
With aluminum (III) chloride; lithium aluminium tetrahydride for 2h; Reflux;

4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → 4-chloro-3',4'-dihydroxydiphenylmethanone (134612-84-3)

Conditions	Yield
With boron tribromide In dichloromethane at -78 - 20℃; for 4h;

4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → (3,4-dimethoxyphenyl)(4-chlorophenyl)methanone oxime (1385825-44-4)

Conditions	Yield
With hydroxylamine hydrochloride; sodium hydroxide In ethanol for 6h; Reflux;

4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → isopropyl((2S)-1-(((3,4-dimethoxylphenyl)(4-chlorophenyl)methyl)amino)-3-methyl-1-oxobutan-2-yl)carbamate (1496524-38-9)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydroxide; hydroxylamine hydrochloride / ethanol / 6 h / Reflux 2.1: ammonium hydroxide; zinc; ammonium acetate / ethanol / 1 h / Reflux 3.1: triethylamine; chloroformic acid ethyl ester / tetrahydrofuran / 1 h / 0 °C 3.2: 2 h / 20 °C View Scheme

4-chloro-3',4'-dimethoxy benzophenone (116412-83-0) → (3,4-dimethoxyphenyl)(4-chlorophenyl)methylamine (1016697-21-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide; hydroxylamine hydrochloride / ethanol / 6 h / Reflux 2: ammonium hydroxide; zinc; ammonium acetate / ethanol / 1 h / Reflux View Scheme

Upstream product

• 91-16-7 1,2-dimethoxybenzene 
• 122-01-0 4-chloro-benzoyl chloride 
• 93-07-2 Veratric acid 
• 155586-38-2 N,3,4-trimethoxy-N-methylbenzamide 
• 51833-36-4 4-chlorophenylmagnesium chloride 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 99-91-2 para-chloroacetophenone 
• 120-80-9 benzene-1,2-diol 
• 74-11-3 para-chlorobenzoic acid 
• 5216-25-1 4-chlorotrichloromethylbenzene 
• 79-34-5 1,1,2,2-tetrachloroethane 

Downstream Products

• 812685-05-5 2-(4-chloro-phenyl)-2-(3,4-dimethoxy-phenyl)-[1,3]dioxolane 
• 1385825-44-4 (3,4-dimethoxyphenyl)(4-chlorophenyl)methanone oxime 
• 1496524-38-9 isopropyl((2S)-1-(((3,4-dimethoxylphenyl)(4-chlorophenyl)methyl)amino)-3-methyl-1-oxobutan-2-yl)carbamate 
• 1016697-21-4 (3,4-dimethoxyphenyl)(4-chlorophenyl)methylamine 
• 110488-70-5 dimethomorph 
• 134612-84-3 4-chloro-3',4'-dihydroxydiphenylmethanone 
• 1239703-27-5 4-chloro-3',4'-dimethoxydiphenylmethane 
• 110488-70-5 dimethomorph 
• 1027937-58-1 5-chloro-2-[2-(3,4-dimethoxy-phenyl)-[1,3]dioxolan-2-yl]-benzoic acid 
• 886494-44-6 (2-amino-4,5-dimethoxyphenyl)-(4-chlorophenyl)methanone 
• 920457-61-0 4-[3-(4-chlorophenyl)-5,6-dimethoxy-1-(4-methylphenylsulfonyl)-1H-2-indolyl]-2-butanone 
• 924635-54-1 4-methyl-N-{2-[(4-chlorophenyl)(5-methylfuran-2-yl)methyl]-4,5-dimethoxyphenyl}benzenesulfonamide 
• 886493-87-4 2-(4-chlorobenzoyl)-4,5-dimethoxy-1-(4-methylphenylsufonamido)benzene 
• 924635-48-3 2-[4-chlorophenyl(hydroxy)methyl]-4,5-dimethoxy-1-(4-methylphenylsulfonamido)benzene 

Relevant articles and documents

Gold-based immunochromatographic strip assay for detecting dimethomorph in vegetables

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The invention discloses a dimethomorph production method in the technical field of pesticide production. The production method comprises: 1) synthesizing veratrole; 2) synthesizing 3,4-dimethoxy-4-chloro-benzophenone; 3) synthesizing acetylmorpholine; and 4) synthesizing dimethomorph. Sodium tert-butoxide is taken as a basic catalyst for synthesizing dimethomorph from 3,4-dimethoxy-4-chloro-benzophenone and acetylmorpholine, and a sodium hydroxide solution is used to perform alkali washing on a reactant in a reaction vessel. Sodium hydroxide has a catalytic effect on synthesis of dimethomorphfrom 3,4-dimethoxy-4-chloro-benzophenone and acetylmorpholine. The defect that the catalytic effect of sodium tert-butoxide is gradually reduced due to unstable chemical property of sodium tert-butoxide and degradation of sodium tert-butoxide when sodium tert-butoxide comes into water is overcome. The dimethomorph product is improved in conversion rate and purity.