33234-36-5

Basic information

• Product Name: 2-CHLORO-3-METHOXYBENZOIC ACID 97
• Synonyms: 2-CHLORO-3-METHOXYBENZOIC ACID 97;BENZOICACID,2-CHLORO-3-METHOXY;2-Chloro-3-Methoxybenzoic acid 97%
• CAS NO: 33234-36-5
• Molecular Formula: C₈H₇ClO₃
• Molecular Weight: 186.59
• Mol File: 33234-36-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 161-165 °C
• Boiling Point: 315 °C at 760 mmHg
• Flash Point: 144.3 °C
• Appearance: /
• Density: 1.352 g/cm³
• Vapor Pressure: 0.00019mmHg at 25°C
• Refractive Index: 1.562
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 2.84±0.25(Predicted)
• CAS DataBase Reference: 2-CHLORO-3-METHOXYBENZOIC ACID 97(CAS DataBase Reference)
• NIST Chemistry Reference: 2-CHLORO-3-METHOXYBENZOIC ACID 97(33234-36-5)
• EPA Substance Registry System: 2-CHLORO-3-METHOXYBENZOIC ACID 97(33234-36-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• Hazardous Substances Data: 33234-36-5(Hazardous Substances Data)

Usage

General Description

2-Chloro-3-methoxybenzoic acid 97 is a chemical compound with the molecular formula C8H7ClO3. It is a white solid with a purity of 97%, and it is commonly used in the pharmaceutical and agrochemical industries as an intermediate for the synthesis of various compounds. 2-CHLORO-3-METHOXYBENZOIC ACID 97 is known to have anti-inflammatory and analgesic properties, making it a potential candidate for the development of new drugs. It is also used as a building block in the production of dyes, pigments, and other organic compounds. Its high purity and versatility make it a valuable chemical in various industrial applications.

InChI:InChI=1/C8H7ClO3/c1-12-6-4-2-3-5(7(6)9)8(10)11/h2-4H,1H3,(H,10,11)

Synthetic route

carbon dioxide (124-38-9) + 2,3-dichloroanisole (1984-59-4) → 1-chloro-3-methoxy-benzene (2845-89-8) + 2-Chloroanisole (766-51-8) + 2-chloro-6-methoxybenzoic acid (3260-89-7) + 2-chloro-3-methoxybenzoic acid (33234-36-5)

Conditions	Yield
With tetrabutylammomium bromide In N,N-dimethyl-formamide at 5℃; electrolysis (I=0.4 A); Yields of byproduct given;	A n/a B n/a C n/a D 78%
With tetrabutylammomium bromide In N,N-dimethyl-formamide at 5℃; electrolysis (I=0.4 A); Yields of byproduct given;	A n/a B n/a C 78% D n/a

3-Methoxybenzoic acid (586-38-9) → 2-chloro-3-methoxybenzoic acid (33234-36-5)

Conditions	Yield
Stage #1: 3-Methoxybenzoic acid With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran at 0℃; for 2h; Stage #2: With hexachloroethane In tetrahydrofuran at 0 - 65℃; for 2.5h; Stage #3: With hydrogenchloride at 20℃;	47%
With hexachloroethane; 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran at 0 - 65℃; for 2.5h;	47%

2-chloro-1-methoxy-3-methylbenzene (90807-19-5) → 2-chloro-3-methoxybenzoic acid (33234-36-5)

Conditions	Yield
With permanganate(VII) ion

2-chloro-3-methoxy benzaldehyde (54881-49-1) → 2-chloro-3-methoxybenzoic acid (33234-36-5)

Conditions	Yield
With potassium permanganate; water
With permanganate(VII) ion

2-chloro-3-methoxy benzaldehyde (54881-49-1) → 2-chloro-3-methoxybenzyl alcohol (52516-43-5) + 2-chloro-3-methoxybenzoic acid (33234-36-5)

Conditions	Yield
With potassium hydroxide at 60 - 70℃;

2-amino-3-methoxybenzoic acid (3177-80-8) → 6,6'-dimethoxy-1,1'-biphenyl-2,2'-dicarboxylic acid (77982-83-3, 85314-52-9, 103420-84-4) + 2-chloro-3-methoxybenzoic acid (33234-36-5)

Conditions	Yield
With hydrogenchloride; ammonium hydroxide; sodium hydroxide; hydroxylamine hydrochloride; copper(II) sulfate; sodium nitrite Yield given. Multistep reaction. Yields of byproduct given;

2-amino-3-methoxybenzoic acid (3177-80-8) → 6,6'-dimethoxy-1,1'-biphenyl-2,2'-dicarboxylic acid (77982-83-3, 85314-52-9, 103420-84-4) + 3-methoxydithiosalicylic acid (20557-42-0) + 2-chloro-3-methoxybenzoic acid (33234-36-5)

Conditions	Yield
With hydrogenchloride; ammonium hydroxide; sodium disulfite; iron(III) chloride; copper(II) sulfate; sodium nitrite Multistep reaction. Title compound not separated from byproducts;

2-Chloro-3-methoxybenzoic acid methyl ester (59425-26-2) → 2-chloro-3-methoxybenzoic acid (33234-36-5)

Conditions	Yield
With sodium hydroxide

2-chloro-3-methoxy benzaldehyde (54881-49-1) + natrium carbonate containing permanganate → 2-chloro-3-methoxybenzoic acid (33234-36-5)

1-methoxy-3-methyl-2-nitro-benzene (5345-42-6) → 2-chloro-3-methoxybenzoic acid (33234-36-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: tin (II)-chloride; hydrochloric acid 3: permanganate; alkali View Scheme
Multi-step reaction with 3 steps 1: tin (II)-chloride; hydrochloric acid 3: permanganate; alkali View Scheme

2-methoxy-6-methylbenzeneamine (50868-73-0) → 2-chloro-3-methoxybenzoic acid (33234-36-5)

Conditions	Yield
Multi-step reaction with 2 steps 2: permanganate; alkali View Scheme

methyl 2-amino-3-methoxybenzoate (5121-34-6) → 2-chloro-3-methoxybenzoic acid (33234-36-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) aq. HCl, NaNO2, (ii) CuCl, aq. HCl 2: aq. NaOH View Scheme

methyl 3-methoxybenzoate (5368-81-0) → 2-chloro-3-methoxybenzoic acid (33234-36-5)

Conditions	Yield
Multi-step reaction with 4 steps 1: (nitration) 2: H2 / Pd-C 3: (i) aq. HCl, NaNO2, (ii) CuCl, aq. HCl 4: aq. NaOH View Scheme

methyl 3-methoxy-2-nitrobenzoate (5307-17-5) → 2-chloro-3-methoxybenzoic acid (33234-36-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: H2 / Pd-C 2: (i) aq. HCl, NaNO2, (ii) CuCl, aq. HCl 3: aq. NaOH View Scheme

2-thiazolylamine (96-50-4) + 2-chloro-3-methoxybenzoic acid (33234-36-5) → 9-methoxy-5H-[1,3]-thiazolo[2,3-b]quinazolin-5-one

Conditions	Yield
With copper; potassium carbonate In N,N-dimethyl-formamide at 25℃; for 0.25h; sonication;	94%
With copper Ullmann condensation; Sonication;

3,5-dimethylphenyl iodide (22445-41-6) + 2-chloro-3-methoxybenzoic acid (33234-36-5) → 3-chloro-4-methoxy-3',5'-dimethyl-[1,1'-biphenyl]-2-carboxylic acid (1421706-52-6)

Conditions	Yield
With silver (II) carbonate; palladium diacetate; potassium carbonate; acetic acid at 120℃; for 24h; Inert atmosphere;	87%

2-chloro-3-methoxybenzoic acid (33234-36-5) → 6-bromo-2-chloro-3-methoxybenzoic acid

Conditions	Yield
With bromine In water at 60℃;	83%

(9aS)-3-(3-bromo-4-fluorophenyl)-1,3,4,6,7,8,9,9a-octahydropyrazino[2,1-c][1,4]oxazine + 2-chloro-3-methoxybenzoic acid (33234-36-5) → [(3R,9aS)-3-(3-bromo-4-fluorophenyl)-3,4,6,7,9,9a-hexahydro-1H-pyrazino[2,1-c][1,4]oxazin-8-yl]-(2-chloro-3-methoxyphenyl)methanone

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere;	78%

ethanol (64-17-5) + 2-chloro-3-methoxybenzoic acid (33234-36-5) → ethyl 2-chloro-3-methoxybenzoate (1261743-55-8)

Conditions	Yield
With sulfuric acid Reflux;	65%

3,5-dimethylphenyl iodide (22445-41-6) + 2-chloro-3-methoxybenzoic acid (33234-36-5) → 3-chloro-4-methoxy-3',5'-dimethyl-1,1'-biphenyl (1344681-45-3)

Conditions	Yield
Stage #1: 3,5-dimethylphenyl iodide; 2-chloro-3-methoxybenzoic acid With palladium diacetate; acetic acid; silver carbonate at 150℃; for 16h; Stage #2: With silver carbonate In dimethyl sulfoxide at 170℃; for 4h; regioselective reaction;	64%

4-(4-chlorobenzoyl)piperidine (53220-41-0) + 2-chloro-3-methoxybenzoic acid (33234-36-5) → (1-(2-chloro-3-methoxybenzoyl)piperidin-4-yl)(4-chlorophenyl)methanone

Conditions	Yield
Stage #1: 2-chloro-3-methoxybenzoic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: 4-(4-chlorobenzoyl)piperidine In N,N-dimethyl-formamide at 20℃;	59%

tert-butylisonitrile (119072-55-8, 7188-38-7) + ((3S,4R)-4-(benzyloxy)-3,4-dihydroisoquinolin-3-yl)methanol (1307770-71-3) + 2-chloro-3-methoxybenzoic acid (33234-36-5) → C30H33ClN2O5 + C30H33ClN2O5

Conditions	Yield
In methanol at 20℃; for 0.25h; Ugi Condensation; diastereoselective reaction;	A 51% B n/a

2-chloro-3-methoxybenzoic acid (33234-36-5) + methyl 1,2,3,4-tetrahydro-5,8-dimethoxy-6-naphthylacetate (84390-70-5) → methyl 7-(2-chloro-3-methoxybenzoyl)-1,2,3,4-tetrahydro-5,8-dimethoxy-6-naphthylacetate (84390-74-9)

Conditions	Yield
With trifluoroacetic anhydride at 60℃; for 144h;	49%

2-chloro-3-methoxybenzoic acid (33234-36-5) + (1,4-Dimethoxy-6-methoxymethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetic acid methyl ester (84390-87-4) → methyl 7-(2-chloro-3-methoxybenzoyl)-1,2,3,4-tetrahydro-5,8-dimethoxy-2-methoxymethyl-6-naphthylacetate (84390-88-5)

Conditions	Yield
With trifluoroacetic anhydride at 60℃; for 144h;	47%

2-methoxy-phenylamine (90-04-0) + 2-chloro-3-methoxybenzoic acid (33234-36-5) → N-(2-methoxyphenyl)-3-methoxyanthranilic acid (88377-30-4)

Conditions	Yield
With i-Amyl alcohol; copper; potassium carbonate

2-chloro-3-methoxybenzyl alcohol (52516-43-5) + 2-chloro-3-methoxybenzoic acid (33234-36-5) → 2-chloro-3-methoxy benzaldehyde (54881-49-1)

Conditions	Yield
With potassium hydroxide at 60 - 70℃;

2-chloro-3-methoxybenzoic acid (33234-36-5) + aniline (62-53-3) → 2-anilino-3-methoxy-benzoic acid (59425-27-3)

Conditions	Yield
With copper; potassium carbonate
With copper diacetate In N,N-dimethyl-formamide at 90℃;

2-chloro-3-methoxybenzoic acid (33234-36-5) + 4-Ethoxyaniline (156-43-4) → 3-methoxy-2-p-phenetidino-benzoic acid (860530-56-9)

Conditions	Yield
With pentan-1-ol; copper; potassium carbonate

2-chloro-3-methoxybenzoic acid (33234-36-5) → 2-Chloro-3-hydroxy benzoic acid (51786-10-8)

Conditions	Yield
With hydrogen bromide

2-chloro-3-methoxybenzoic acid (33234-36-5) → 4,5-dimethoxyacridine (357622-01-6)

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium carbonate; copper; isoamyl alcohol 2: phosphoryl chloride / 160 - 165 °C 3: sodium-amalgam; sodium hydrogencarbonate / 80 °C 4: concentrated sulfuric acid; acetic acid; sodium nitrite / Reagens 4:Wasser View Scheme

2-chloro-3-methoxybenzoic acid (33234-36-5) → 4,5-dimethoxy-9,10-dihydroacridine

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate; copper; isoamyl alcohol 2: phosphoryl chloride / 160 - 165 °C 3: sodium-amalgam; sodium hydrogencarbonate / 80 °C View Scheme

2-chloro-3-methoxybenzoic acid (33234-36-5) → 4,5-dimethoxyacridine-9(10H)-one (88377-28-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate; copper; isoamyl alcohol 2: phosphoryl chloride / 160 - 165 °C View Scheme

Upstream product

• 90807-19-5 2-chloro-1-methoxy-3-methylbenzene 
• 54881-49-1 2-chloro-3-methoxy benzaldehyde 
• 124-38-9 carbon dioxide 
• 1984-59-4 2,3-dichloroanisole 
• 50868-73-0 2-methoxy-6-methylbenzeneamine 
• 5307-17-5 methyl 3-methoxy-2-nitrobenzoate 
• 5368-81-0 methyl 3-methoxybenzoate 
• 5121-34-6 methyl 2-amino-3-methoxybenzoate 
• 5345-42-6 1-methoxy-3-methyl-2-nitro-benzene 
• 586-38-9 3-Methoxybenzoic acid 
• 59425-26-2 2-Chloro-3-methoxybenzoic acid methyl ester 
• 3177-80-8 2-amino-3-methoxybenzoic acid 

Downstream Products

• 88377-30-4 N-(2-methoxyphenyl)-3-methoxyanthranilic acid 
• 51786-10-8 2-Chloro-3-hydroxy benzoic acid 
• 88377-28-0 4,5-dimethoxyacridine-9(10H)-one 
• 61535-32-8 3-Benzyloxy-2-chloro-benzoyl chloride 
• 61535-31-7 3-Benzyloxy-2-chloro-benzoic acid 
• 183513-64-6 2-chloro 3-methoxy phenyl isocyanate 
• 86269-98-9 2-chloro-3-methoxybenzoyl chloride 
• 1616288-99-3 2-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-7-hydroxy-3,4-dihydroisoquinolin-1(2H)-one 
• 1616288-98-2 2-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-8-chloro-1-oxo-1,2,3,4-tetrahydroisoquinolin-7-yl diethylcarbamate 
• 22246-04-4 7-methoxy-3,4-dihydro-2H-isoquinolin-1-one 
• 1180495-74-2 2-amino-3-chloro-4-methoxy benzoic acid 

Relevant articles and documents

First general, direct, and regioselective synthesis of substituted methoxybenzoic acids by ortho metalation

(Chemical Equation Presented) New general methodology of value in aromatic chemistry based on ortho-metalation sites in o-, m-, and p-anisic acids (1-3) (Scheme 1) is described. The metalation can be selectively directed to either of the ortho positions by varying the base, metalation temperature, and exposure times. Metalation of o-anisic acid (1) with s-BuLi/TMEDA in THF at -78°C occurs exclusively in the position adjacente to the carboxylate. On the other hand, a reversal of regioselectivity is observed with n-BuLi/t-BuOK. With LTMP at 0°C, the two directors of m-anisic acid (2) function in concert to direct introduction of the metal between them while n-BuLi/t-BuOK removes preferentially the proton located ortho to the methoxy and para to the carboxylate (H-4). s-BuLi/TMEDA reacts with p-anisic acid (3) exclusively in the vicinity of the carboxylate. According to these methodologies, routes to very simple methoxybenzoic acids with a variety of functionalities that are not easily accessible by other means have been developed (Table 1).

Synthesis of a New Allosteric Carrier Containing Three Conformationally Related Subunits

A new allosteric carrier was prepared.This compound consists of three crown ether subunits in which conformational information is transferred through two biphenyl systems.This system is able to complex nonionic species in both external crown ether subunits.The allosteric cooperativity in this system was established and its ability to transport Hg(CN)2 has been studied.