3535-37-3

Basic information

• Product Name: 3,4-DIMETHOXYBENZOYL CHLORIDE
• Synonyms: 3,4-DIMETHOXYBENZENE-1-CARBONYL CHLORIDE;3,4-DIMETHOXYBENZOYL CHLORIDE;BUTTPARK 94\04-06;3,4-Dimethoxybenzoyl chloride ,98%;3,4-Dimethoxybenzoic acid chloride;3,4-DiMethoxybenzoyl chloride, 98% 5GR;3,4-Dimethoxy-1-benzenecarbonyl chloride;VERATROYL CHLORIDE
• CAS NO: 3535-37-3
• Molecular Formula: C₉H₉ClO₃
• Molecular Weight: 200.62
• EINECS: 222-568-0
• Product Categories: Aromatic Halides (substituted)
• Mol File: 3535-37-3.mol
• Article Data: 118

Chemical Properties

• Melting Point: 70-73 °C(lit.)
• Boiling Point: 95-98°C 1mm
• Flash Point: 95-98°C/1mm
• Appearance: Off-white to gray/Crystals, Flakes or Chunks
• Density: 1.2799 (rough estimate)
• Vapor Pressure: 0.00129mmHg at 25°C
• Refractive Index: 1.5230 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: soluble in Toluene
• Sensitive: Moisture Sensitive
• BRN: 783596
• CAS DataBase Reference: 3,4-DIMETHOXYBENZOYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DIMETHOXYBENZOYL CHLORIDE(3535-37-3)
• EPA Substance Registry System: 3,4-DIMETHOXYBENZOYL CHLORIDE(3535-37-3)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 10-21
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 3535-37-3(Hazardous Substances Data)

Usage

Chemical Properties

off-white to grey crystals, flakes or chunks

Uses

Different sources of media describe the Uses of 3535-37-3 differently. You can refer to the following data:
1. 3,4-Dimethoxybenzoyl Chloride is a benzoyl chloride derivative used in the preparation of a variety of biologically active compounds such as bronchodilators
2. 3,4-Dimethoxybenzoyl chloride has been used in synthesis of:(+)-5-(3,4-dimethoxyphenyl)-4-[[N-[(4S)-2-oxo-4-(phenylmethyl)-2-oxazolidinyl]]carbonyl] oxazole and its enantiomerN-(2,5-dibromophenyl)-3,4-dimethoxybenzamide

InChI:InChI=1/C9H9ClO3/c1-12-7-4-3-6(9(10)11)5-8(7)13-2/h3-5H,1-2H3

Synthetic route

Veratric acid (93-07-2) → 3,4-dimethoxybenzoic acid chloride (3535-37-3)

Conditions	Yield
With pyridine; thionyl chloride In benzene	100%
With thionyl chloride In dichloromethane at 40℃; for 4h; Solvent;	100%
With thionyl chloride at 20℃; for 5h;	100%

1-(3,4-dimethoxyphenyl)ethanone (1131-62-0) → 3,4-dimethoxybenzoic acid chloride (3535-37-3)

Conditions	Yield
Stage #1: 1-(3,4-dimethoxyphenyl)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;	77%
Stage #1: 1-(3,4-dimethoxyphenyl)ethanone With pyridine; sulfur monochloride In chlorobenzene at 20℃; Stage #2: With thionyl chloride In chlorobenzene at 20 - 132℃;	47%
With pyridine; disulfur dichloride at 70 - 136℃; for 22h;	79 %Spectr.

1-(3,4-Dimethoxy-benzoyl)-3-methyl-3H-imidazol-1-ium; chloride (93342-78-0) → 1-methyl-1H-imidazole (616-47-7) + 3,4-dimethoxybenzoic acid chloride (3535-37-3)

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

(3,4-dimethoxyphenyl)methanol (93-03-8) → 3,4-dimethoxybenzoic acid chloride (3535-37-3)

Conditions	Yield
With phosphorus pentachloride In diethyl ether at 0℃;

thionyl chloride (7719-09-7) + Veratric acid (93-07-2) → 3,4-dimethoxybenzoic acid chloride (3535-37-3)

phosphorus pentachloride (10026-13-8, 874483-75-7) + Veratric acid (93-07-2) + CS2 → 3,4-dimethoxybenzoic acid chloride (3535-37-3)

3-methoxy-4-hydroxybenzoic acid (121-34-6) → 3,4-dimethoxybenzoic acid chloride (3535-37-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: KOH / ethanol; H2O / 25 h / Heating 2: SOCl2 / 3 h / Heating View Scheme

Veratric acid (93-07-2) + N-ethyl-N-(6-hydroxyhexyl)-6-methoxy-1,2,3,4-tetrahydro-2-naphthylamine (69788-97-2) → 3,4-dimethoxybenzoic acid chloride (3535-37-3)

methyl 3,4-dimethoxybenzoate (2150-38-1) → 3,4-dimethoxybenzoic acid chloride (3535-37-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / methanol; water / 2 h / Reflux 2: thionyl chloride / 2 h / Reflux View Scheme

oxalyl dichloride (79-37-8) + Veratric acid (93-07-2) → 3,4-dimethoxybenzoic acid chloride (3535-37-3)

Conditions	Yield
In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h;

1-iodo-3,4-dimethoxybenzene (5460-32-2) + butyryl chloride (141-75-3) → 3,4-dimethoxybenzoic acid chloride (3535-37-3)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 100℃; for 16h; Sealed tube; Inert atmosphere;

3,4-dimethoxy-benzaldehyde (120-14-9) → 3,4-dimethoxybenzoic acid chloride (3535-37-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium permanganate / acetone; water 2: thionyl chloride / 2 h / Reflux View Scheme

2-carbomethoxyaniline (134-20-3) + 3,4-dimethoxybenzoic acid chloride (3535-37-3) → methyl N-(3,4-dimethoxybenzoyl)anthranilate (67836-52-6)

Conditions	Yield
With pyridine In dichloromethane at 20℃; for 0.5h;	100%

diisopropylamine (108-18-9) + 3,4-dimethoxybenzoic acid chloride (3535-37-3) → 3,4-dimethoxy-N,N-bis-(methylethyl)benzamide (156300-76-4)

Conditions	Yield
In benzene for 3h; 0 deg C to RT;	100%
With triethylamine In dichloromethane at 0 - 20℃; for 12h;	73%

methyl-3,4-dihydro-6,7-dimethoxy-1-methylisoquinoline-3-carboxylate (78083-81-5) + 3,4-dimethoxybenzoic acid chloride (3535-37-3) → methyl 1,2,3,4-tetrahydro-6,7-dimethoxy-1-methylene-2-veratroylisoquinoline-3-carboxylate (78083-82-6)

Conditions	Yield
With triethylamine In benzene for 3h; Heating;	100%

2-(3-methoxyphenyl)-ethanol (5020-41-7) + 3,4-dimethoxybenzoic acid chloride (3535-37-3) → 3,4-dimethoxybenzoic acid 2-(3-methoxyphenyl)ethyl ester

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0℃;	100%
With dmap; triethylamine In dichloromethane at 20℃; for 16h;

3,4-dimethoxybenzoic acid chloride (3535-37-3) + (+/-)-3-amino-1-[3-(3,4-methylenedioxyphenoxy)propyl]-piperidine (619329-87-2) → (+/-)-3,4-dimethoxy-N-{1-[3-(3,4-methylenedioxyphenoxy)propyl]-3-piperidyl}benzamide

Conditions	Yield
In ethyl acetate at 20℃; for 14h;	100%

Methyl 2-aminothiophene-3-carboxylate (4651-81-4) + 3,4-dimethoxybenzoic acid chloride (3535-37-3) → methyl 2-(3,4-dimethoxybenzamido)thiophene-3-carboxylate (773071-56-0)

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; for 12h;	100%
With triethylamine In dichloromethane at 20℃; Cooling with ice;	15%
With triethylamine In dichloromethane at 0 - 20℃;	15%

N-((2,2-dimethyl-2H-pyrano[3,2-b]pyridin-6-yl)methyl)aniline (1342891-17-1) + 3,4-dimethoxybenzoic acid chloride (3535-37-3) → N-((2,2-dimethyl-2H-pyrano[3,2-b]pyridin-6-yl)methyl)-3,4-dimethoxy-N-phenylbenzamide (1342891-18-2)

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	100%
With triethylamine In dichloromethane at 20℃;	98%

malonic acid dimethyl ester (108-59-8) + 3,4-dimethoxybenzoic acid chloride (3535-37-3) → dimethyl 2-(3,4-dimethoxybenzoyl)malonate

Conditions	Yield
Stage #1: malonic acid dimethyl ester With triethylamine; magnesium chloride In acetonitrile at 0℃; for 0.5h; Stage #2: 3,4-dimethoxybenzoic acid chloride In acetonitrile at 20℃; for 16h;	100%

2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylic acid ethyl ester (40106-13-6) + 3,4-dimethoxybenzoic acid chloride (3535-37-3) → ethyl 2-[(3,4-dimethoxybenzoyl)amino]-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylate

Conditions	Yield
With pyridine at 20℃; for 1h;	100%

2-(3,4-dimethoxyphenyl)-ethylamine (120-20-7) + 3,4-dimethoxybenzoic acid chloride (3535-37-3) → N-<2-(3,4-dimethoxyphenyl)ethyl>-3,4-dimethoxyphenylacetamide (102011-15-4)

Conditions	Yield
With sodium hydroxide In dichloromethane; water at 0℃; for 1.5h; Sealed tube;	99%
With calcium oxide; benzene
With sodium hydroxide In 1,4-dioxane

4-methylsulfanylaniline (104-96-1) + 3,4-dimethoxybenzoic acid chloride (3535-37-3) → 3,4-Dimethoxy-N-(4-methylsulfanyl-phenyl)-benzamide

Conditions	Yield
With Amberlite IRA-68 In ethyl acetate Ambient temperature;	99%

3,4-dimethoxybenzoic acid chloride (3535-37-3) + benzyl alcohol (100-51-6) → benzyl 3,4-dimethoxybenzoate

Conditions	Yield
With Amberlite IRA-68 In ethyl acetate Ambient temperature;	99%
With triethylamine In acetonitrile at 20℃; for 3h;	15%

3,4-dimethoxybenzoic acid chloride (3535-37-3) + 1-benzyl-3-[(2,2-dimethoxyethyl)amino]piperidine (204979-42-0) → (+/-)-N-(1-benzyl-3-piperidyl)-N'-(2,2-dimethoxyethyl)-3.4-dimethoxybenzamide (204979-43-1)

Conditions	Yield
In acetonitrile at 20℃; for 0.5h;	99%
With triethylamine In tetrahydrofuran at 20℃; for 3h;	2.11 g

naphthalen-2-ylamine (91-59-8) + 3,4-dimethoxybenzoic acid chloride (3535-37-3) → 3,4-dimethoxy-N-(naphthalen-2-yl)benzamide (331270-79-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	99%

1-benzoyloxy-5-methoxy naphthalene (64725-89-9) + 3,4-dimethoxybenzoic acid chloride (3535-37-3) → 8-benzoyloxy-4-methoxy-1-veratroylnaphthalene

Conditions	Yield
With aluminium trichloride In various solvent(s) at 0℃;	98%

tert-butylamine (75-64-9) + 3,4-dimethoxybenzoic acid chloride (3535-37-3) → N-(tert-butyl)-3,4-dimethoxybenzamide (349107-92-2)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; for 10h; Inert atmosphere;	98%
With triethylamine In dichloromethane at 0 - 25℃; for 5h;
With triethylamine In dichloromethane at 20℃; for 5h;
Stage #1: 3,4-dimethoxybenzoic acid chloride With triethylamine In diethyl ether at 0℃; for 0.25h; Stage #2: tert-butylamine In diethyl ether at 20℃; for 3h;	1.52 g

tert-butyl (1-methyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridin-7-yl)carbamate + 3,4-dimethoxybenzoic acid chloride (3535-37-3) → tert-butyl (4-(3,4-dimethoxybenzoyl)-1-methyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-b]pyridin-7-yl)carbamate

Conditions	Yield
With pyridine at 20℃;	98%

1-indoline (496-15-1) + 3,4-dimethoxybenzoic acid chloride (3535-37-3) → (3,4-dimethoxyphenyl)(indolin-1-yl)methanone (128581-33-9)

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;	98%

3,4-dimethoxyaniline (6315-89-5) + 3,4-dimethoxybenzoic acid chloride (3535-37-3) → N-(3,4-dimethoxyphenyl)-3,4-dimethoxybenzamide (59699-54-6)

Conditions	Yield
With pyridine In dichloromethane	97%
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere;	88%
With diethyl ether; potassium carbonate
With triethylamine In dichloromethane

N-methoxylamine hydrochloride (593-56-6) + 3,4-dimethoxybenzoic acid chloride (3535-37-3) → 3,4-dimethoxy-N-methoxybenzamide (25563-13-7)

Conditions	Yield
With potassium carbonate In water; ethyl acetate at 0 - 20℃;	97%
With potassium carbonate In water; ethyl acetate at 0 - 20℃;
Stage #1: N-methoxylamine hydrochloride With potassium carbonate In water; ethyl acetate Stage #2: 3,4-dimethoxybenzoic acid chloride In water; ethyl acetate at 0 - 20℃; for 5h;

3,4-dimethoxybenzoic acid chloride (3535-37-3) + N,N-dipropargylamine hydrochloride → 3,4-dimethoxy-N,N-bis(prop-2-yn-1-yl)benzamide (1300021-71-9)

Conditions	Yield
Stage #1: N,N-dipropargylamine hydrochloride With dmap; triethylamine In dichloromethane at 20℃; for 0.25h; Inert atmosphere; Stage #2: 3,4-dimethoxybenzoic acid chloride In dichloromethane at 0 - 20℃; for 3.5h; Inert atmosphere;	97%
Stage #1: N,N-dipropargylamine hydrochloride With triethylamine; trifluoroacetic acid In dichloromethane at 20℃; for 0.25h; Inert atmosphere; Stage #2: 3,4-dimethoxybenzoic acid chloride In dichloromethane at 0 - 20℃; for 3.5h; Inert atmosphere;

(S)-4-Benzyl-3-(2-methyleneamino-acetyl)-oxazolidin-2-one (1062211-31-7) + 3,4-dimethoxybenzoic acid chloride (3535-37-3) → (S)-4-Benzyl-3-[5-(3,4-dimethoxy-phenyl)-oxazole-4-carbonyl]-oxazolidin-2-one

Conditions	Yield
With trimethyl-pro-azaphosphatrane In tetrahydrofuran 1.) 0 deg C, 20 min, 2.) room temperature, 30 min;	96%

(R)-4-Benzyl-3-(2-methyleneamino-acetyl)-oxazolidin-2-one + 3,4-dimethoxybenzoic acid chloride (3535-37-3) → (R)-4-Benzyl-3-[5-(3,4-dimethoxy-phenyl)-oxazole-4-carbonyl]-oxazolidin-2-one

Conditions	Yield
With trimethyl-pro-azaphosphatrane In tetrahydrofuran 1.) 0 deg C, 20 min, 2.) room temperature, 30 min;	96%

3',4'-dimethoxyacetanilide (881-70-9) + 3,4-dimethoxybenzoic acid chloride (3535-37-3) → 2-acetylamino-3',4,4'-5-tetramethoxybenzophenone (189001-13-6)

Conditions	Yield
With tin(IV) chloride; trichlorophosphate In dichloromethane Friedel-Crafts reaction; Heating;	96%

7-bromo-6-methylamino-2,2-dimethyl-2-silatetralin (880550-62-9) + 3,4-dimethoxybenzoic acid chloride (3535-37-3) → N-(7-bromo-2,2-dimethyl-2-silatetralin-6-yl)-N-methylveratramide (880550-63-0)

Conditions	Yield
With potassium carbonate In dichloromethane at 20℃; for 24h;	96%

ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (4506-71-2) + 3,4-dimethoxybenzoic acid chloride (3535-37-3) → ethyl 2-[(3,4-dimethoxybenzoyl)amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate

Conditions	Yield
With pyridine at 20℃; for 1h;	96%

morpholine (110-91-8) + 3,4-dimethoxybenzoic acid chloride (3535-37-3) → 4-(3’,4’-dimethoxybenzoyl)morpholine (22792-13-8)

Conditions	Yield
In dichloromethane at 0℃; for 2h;	95%

(-)-menthol (2216-51-5) + 3,4-dimethoxybenzoic acid chloride (3535-37-3) → (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 3,4-dimethoxybenzoate

Conditions	Yield
With pyridine In diethyl ether at 48℃; Acylation; Heating;	95%

3,4-dimethoxybenzoic acid chloride (3535-37-3) + 3,5-dimethoxy-2-(methoxyacetyl)aniline (212512-28-2) → N-(3,5-dimethoxy-2-(2-methoxyacetyl)phenyl)-3,4-dimethoxybenzamide (1026457-04-4)

Conditions	Yield
With pyridine for 18h; Acylation; Heating;	95%
With dmap; N-ethyl-N,N-diisopropylamine at 80℃; Sealed tube;	67%

Upstream product

• 93-07-2 Veratric acid 
• 69788-97-2 N-ethyl-N-(6-hydroxyhexyl)-6-methoxy-1,2,3,4-tetrahydro-2-naphthylamine 
• 1131-62-0 1-(3,4-dimethoxyphenyl)ethanone 
• 79-37-8 oxalyl dichloride 
• 5460-32-2 1-iodo-3,4-dimethoxybenzene 
• 141-75-3 butyryl chloride 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 2150-38-1 methyl 3,4-dimethoxybenzoate 
• 121-34-6 3-methoxy-4-hydroxybenzoic acid 
• 10026-13-8 phosphorus pentachloride 
• 7719-09-7 thionyl chloride 
• 93-03-8 (3,4-dimethoxyphenyl)methanol 
• 93342-78-0 1-(3,4-Dimethoxy-benzoyl)-3-methyl-3H-imidazol-1-ium; chloride 

Downstream Products

• 52196-76-6 2-diazo-1-(3,4-dimethoxyphenyl)ethan-1-one 
• 102006-25-7 3,4-dimethoxy-benzoic acid-(1-methyl-[3]piperidyl ester) 
• 23095-65-0 2-(3,4-dimethoxy-benzoyl)-1,2-dihydro-isoquinoline-1-carbonitrile 
• 97077-93-5 veratric acid-(2-indol-3-yl-ethylamide) 
• 101867-39-4 3,4-dimethoxy-benzoic acid-(β-piperidino-isopropyl ester) 
• 122361-23-3 6,7-dimethoxy-2-(4-veratroyloxy-butyl)-1,2,3,4-tetrahydro-isoquinoline; hydrochloride 
• 76787-81-0 3-oxo-2-veratroyl-butyric acid ethyl ester 
• 67858-33-7 2-acetylphenyl-3,4-dimethoxybenzoate 
• 26578-71-2 3,4-dimethoxy-benzoic acid-(4-formyl-phenyl ester) 
• 1718-92-9 veratric acid p-anisidide 
• 102011-15-4 N-<2-(3,4-dimethoxyphenyl)ethyl>-3,4-dimethoxyphenylacetamide 
• 124113-14-0 16α-piperidino-3β-veratroyloxy-pregn-5-en-20-one 
• 2898-54-6 3,4,4'-trimethoxybenzophenone 
• 74697-54-4 3,4,4′-trihydroxybenzophenone 

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