3-Methoxysalicylic acid supplier

Name
3-Methoxysalicylic acid
EINECS 212-888-9
CAS No. 877-22-5
Article Data28
CAS DataBase
Density 1.351 g/cm³
Solubility
Melting Point 147-150 °C(lit.)
Formula C₈H₈O₄
Boiling Point 315.7 °C at 760 mmHg
Molecular Weight 168.149
Flash Point 131.7 °C
Transport Information
Appearance beige powder
Safety 26-37/39-36
Risk Codes 36/37/38-20/21/22
Molecular Structure
Hazard Symbols Xi,Xn
Synonyms Salicylicacid, 3-methoxy- (4CI);m-Anisic acid, 2-hydroxy- (8CI);2-Hydroxy-3-methoxybenzoic acid;3-Methoxy-2-hydroxybenzoic acid;NSC 134533;NSC 408167;o-Vanillic acid;
PSA 66.76000
LogP 1.09900

Synthetic route

: 1521-38-6
2,3-dimethoxybenzoic acid

: 877-22-5
3-methoxysalicylic acid

Conditions

Conditions	Yield
With piperazine In N,N-dimethyl acetamide at 150℃; for 0.2h; Substitution;	94%
With hydrogen bromide

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

: 877-22-5
3-methoxysalicylic acid

Conditions

Conditions	Yield
With potassium hydroxide; sodium tetrahydroborate; air; palladium on activated charcoal In methanol at 20℃; for 48h;	89%
With sodium chlorite; sodium dihydrogenphosphate; dimethyl sulfoxide In water Ambient temperature;	83%
With potassium hydroxide at 215℃;

: 4383-05-5
2-hydroxy-3-methoxybenzyl alcohol

: 877-22-5
3-methoxysalicylic acid

Conditions

Conditions	Yield
With sodium tetrahydroborate; 1% Pd/C; water; potassium hydroxide In methanol at 20℃; for 48h; In air;	89%

: 586-38-9
3-Methoxybenzoic acid

: 877-22-5
3-methoxysalicylic acid

Conditions

Conditions	Yield
With 2,2,6,6-tetramethylpiperidinyl-lithium; oxygen In tetrahydrofuran at 0 - 20℃;	54%
With [Fe(II)(N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)-1,2-ethylenediamine)(CH3CN)2](ClO4)2; dihydrogen peroxide In water; acetonitrile at 20℃; Inert atmosphere; regioselective reaction;	52 %Spectr.

: 124-38-9
carbon dioxide

: 90-05-1
2-methoxy-phenol

A: 121-34-6
3-methoxy-4-hydroxybenzoic acid

B: 877-22-5
3-methoxysalicylic acid

Conditions

Conditions	Yield
Stage #1: 2-methoxy-phenol With potassium hydroxide In water at 120℃; for 2h; Dean-Stark; Stage #2: carbon dioxide In 1-methyl-pyrrolidin-2-one at 118℃; for 2h; Temperature; Solvent; High pressure; regioselective reaction;	A 48% B n/a

...Expand

: 2-acetoxy-1-methoxy-3-propyl-benzene

: 877-22-5
3-methoxysalicylic acid

: 196601-61-3
2-benzenesulfonyloxy-3-methoxy-benzoic acid

: 877-22-5
3-methoxysalicylic acid

Conditions

Conditions	Yield
With sodium hydroxide

: 109-72-8, 29786-93-4
n-butyllithium

: 60-29-7
diethyl ether

: 90-05-1
2-methoxy-phenol

A: 877-22-5
3-methoxysalicylic acid

B: 2169-28-0
2-methoxy-3-hydroxybenzoic acid

Conditions

Conditions	Yield
anschliessendes Behandeln mit CO2;

...Expand

: 90-05-1
2-methoxy-phenol

: 877-22-5
3-methoxysalicylic acid

Conditions

Conditions	Yield
With potassium carbonate anschliessend Erhitzen mit Kohlendioxid, jeweils auf 180grad;

: 57544-05-5
8-methoxy-3-nitro-2-(4-methoxyphenyl)-2H-chromene

A: 877-22-5
3-methoxysalicylic acid

B: 91735-21-6
3-Hydroxy-8-methoxy-2-(4-methoxy-phenyl)-chromen-4-one

C: 100-09-4
4-methoxybenzoic acid

Conditions

Conditions	Yield
With dimethyl sulfoxide for 0.166667h;

...Expand

: 57543-87-0
8-methoxy-3-nitro-2-phenyl-2H-chromene

A: 877-22-5
3-methoxysalicylic acid

B: 88252-61-3
8-methoxy flavonol

C: 65-85-0
benzoic acid

Conditions

Conditions	Yield
With dimethyl sulfoxide for 0.166667h;

...Expand

: 148-53-8
3-methoxy-2-hydroxybenzaldehyde

potassium hydroxide: potassium hydroxide

: 877-22-5
3-methoxysalicylic acid

Conditions

Conditions	Yield
at 215℃;

: 124-38-9
carbon dioxide

: 13052-77-2
sodium 2-methoxyphenolate

: 877-22-5
3-methoxysalicylic acid

Conditions

Conditions	Yield
unter Druck;
at 115℃;
at 200℃;

: 1521-38-6
2,3-dimethoxybenzoic acid

diluted hydrobromic acid: diluted hydrobromic acid

: 877-22-5
3-methoxysalicylic acid

: 15719-64-9, 15719-76-3, 97762-63-5
methylammonium carbonate

sodium-salt of guaiacol: sodium-salt of guaiacol

A: 877-22-5
3-methoxysalicylic acid

B: 19829-72-2
2,3-dihydroxyterephthalic acid

Conditions

Conditions	Yield
at 230℃;

...Expand

: 2-acetoxy-1-ethyl-3-methoxy-benzene

aqueous KMnO4: aqueous KMnO4

: 877-22-5
3-methoxysalicylic acid

Conditions

Conditions	Yield
anschliessende Hydrolyse;

: 196601-61-3
2-benzenesulfonyloxy-3-methoxy-benzoic acid

diluted NaOH-solution: diluted NaOH-solution

: 877-22-5
3-methoxysalicylic acid

: 124-38-9
carbon dioxide

: 13052-77-2
sodium 2-methoxyphenolate

A: 877-22-5
3-methoxysalicylic acid

B: 19829-72-2
2,3-dihydroxyterephthalic acid

Conditions

Conditions	Yield
at 230℃;

...Expand

: 586-38-9
3-Methoxybenzoic acid

A: 99-50-3
3,4-Dihydroxybenzoic acid

B: 121-34-6
3-methoxy-4-hydroxybenzoic acid

C: 877-22-5
3-methoxysalicylic acid

D: 99-06-9
3-Carboxyphenol

Conditions

Conditions	Yield
With air In water pH=8.4; Product distribution; G-values; Further Variations:; dose; γ-Irradiation;

...Expand

: 586-38-9
3-Methoxybenzoic acid

A: 121-34-6
3-methoxy-4-hydroxybenzoic acid

B: 877-22-5
3-methoxysalicylic acid

C: 99-06-9
3-Carboxyphenol

Conditions

Conditions	Yield
With dinitrogen monoxide In water pH=8.6; Product distribution; G-values; Further Variations:; dose; γ-Irradiation;

...Expand

: 586-38-9
3-Methoxybenzoic acid

A: 121-34-6
3-methoxy-4-hydroxybenzoic acid

B: 877-22-5
3-methoxysalicylic acid

C: 2612-02-4
5-methoxysalicylic acid

D: 99-06-9
3-Carboxyphenol

Conditions

Conditions	Yield
With dinitrogen monoxide; potassium hexacyanoferrate(III) In water Product distribution; γ-Irradiation;

...Expand

: 86-51-1
2,3-dimethyoxybenzaldehyde

: 877-22-5
3-methoxysalicylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: alcoholic KOH-solution 2: diluted hydrobromic acid View Scheme

: 2426-85-9
2-Hydroxy-3-methoxybenzaldehyde benzenesulfonate

: 877-22-5
3-methoxysalicylic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: permanganate; magnesium sulfate 2: NaOH-solution View Scheme

: 298-14-6
potassium hydrogencarbonate

: 90-05-1
2-methoxy-phenol

: 877-22-5
3-methoxysalicylic acid

Conditions

Conditions	Yield
With salicylic acid decarboxylase from Trichosporon moniliiforme In aq. phosphate buffer at 30℃; for 24h; Kolbe-Schmidt Synthesis; Enzymatic reaction; regioselective reaction;

: 877-22-5
3-methoxysalicylic acid

: 134419-47-9
5-iodo-3-methoxysalicylic acid

Conditions

Conditions	Yield
With Iodine monochloride; silver nitrate In pyridine; chloroform at 20℃; for 2h;	100%
With Iodine monochloride In acetic acid 1.) 20 deg C, 2 h, 2.) 70 deg C, 1 h;	54%

: 877-22-5
3-methoxysalicylic acid

: 106-95-6
allyl bromide

: C14H16O4

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃; for 17h;	100%

: 67-56-1
methanol

: 877-22-5
3-methoxysalicylic acid

: 6342-70-7
3-methoxymethylsalicylate

Conditions

Conditions	Yield
With hydrogenchloride for 2h; Heating;	98%
With sulfuric acid for 16h; Reflux;	96%
With sulfuric acid for 48h; Heating;	95%

: 75-09-2
dichloromethane

: 877-22-5
3-methoxysalicylic acid

: 1591954-10-7
C9H8O4

Conditions

Conditions	Yield
With potassium phosphate tribasic trihydrate In N,N-dimethyl-formamide at 100℃; under 760.051 Torr; for 6h; Green chemistry;	98%

: 110-53-2
1-Bromopentane

: 877-22-5
3-methoxysalicylic acid

: 3-methoxy-2-pentyloxybenzoic acid

Conditions

Conditions	Yield
With hydrogenchloride; sodium hydroxide; potassium carbonate In ethanol; water; N,N-dimethyl-formamide	97%

: 877-22-5
3-methoxysalicylic acid

: 56-36-0
tributyltin acetate

: tri-n-butyltin 3-methoxysalicylate

Conditions

Conditions	Yield
In ethanol; toluene byproducts: acetic acid; equimolar amts. of Sn-compd. and the benzoic acid are mixed with toluene/EtOH (3:1), mixt. refluxed (4 h); the azeotrope acetic acid/EtOH/toluene followed by the azeotrope toluene/EtOH is distilled off to 50% of its initial vol., evapn. (reduced pressure);	97%

: 877-22-5
3-methoxysalicylic acid

: 20718-78-9
2-Hydroxy-3-methoxy-5-nitrobenzoic acid

Conditions

Conditions	Yield
With sulfuric acid; nitric acid In dichloromethane at 0 - 20℃; for 3h; Nitration;	94%
With nitric acid at 48℃; im Rohr;
With nitric acid; acetic acid at 0℃;
With sulfuric acid; nitric acid at 0 - 20℃; for 3h; Inert atmosphere;

: 877-22-5
3-methoxysalicylic acid

: 62-53-3
aniline

: 52607-63-3
(E)-5-(2-phenyldiazenyl)-2-hydroxy-3-methoxybenzaldehyde

Conditions

Conditions	Yield
Stage #1: aniline With hydrogenchloride; sodium nitrite In water at 0℃; for 1.5h; Stage #2: 3-methoxysalicylic acid In water at 0℃; for 1h; Alkaline conditions;	94%

: 877-22-5
3-methoxysalicylic acid

: 6342-70-7
3-methoxymethylsalicylate

Conditions

Conditions	Yield
With methanol; sulfuric acid In methanol for 96h;	91.2%

: 108-73-6
3,5-dihydroxyphenol

: 877-22-5
3-methoxysalicylic acid

: 6563-47-9
1,3-dihydroxy-5-methoxy-9H-xanthen-9-one

Conditions

Conditions	Yield
With eaton’s reagent at 80℃; for 0.333333h;	91%
With zinc(II) chloride; trichlorophosphate
With zinc(II) chloride; trichlorophosphate Condensation; cyclization; Heating;

: 121882-74-4
tris(p‐tolyl)bismuth dibromide

: 877-22-5
3-methoxysalicylic acid

: bis(3‐methoxysalicylato)tris(p‐tolyl)bismuth(V)

Conditions

Conditions	Yield
With triethylamine In toluene for 2h; Inert atmosphere;	91%

: 121882-74-4
tris(p‐tolyl)bismuth dibromide

: 877-22-5
3-methoxysalicylic acid

: bis(3‐methylbenzoato)tris(p‐tolyl)bismuth(V)

Conditions

Conditions	Yield
With triethylamine In toluene for 2h; Inert atmosphere;	87%

: 877-22-5
3-methoxysalicylic acid

: 400-98-6
4-trifluoromethyl-2-nitroaniline

: 900147-76-4
C15H10ClF3N2O4

Conditions

Conditions	Yield
With phosphorus trichloride In chlorobenzene at 150℃; for 1h;	85%

: 89430-08-0
C20H15N2PS2

: 877-22-5
3-methoxysalicylic acid

: 8-methoxy-2-thioxo-2,3-dihydro-4H-1,3-benzoxazin-4-one

Conditions

Conditions	Yield
In dichloromethane	84%

: 877-22-5
3-methoxysalicylic acid

: 669067-80-5
4-(6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-yl)-butan-1-amine

: 1353004-57-5
N-(4-(6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-yl)-butyl)-2-hydroxy-3-methoxybenzamide

Conditions

Conditions	Yield
Stage #1: 3-methoxysalicylic acid With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 0.0833333h; Stage #2: 4-(6,7-dimethoxy-3,4-dihydroisoquinoline-2(1H)-yl)-butan-1-amine In tetrahydrofuran at 20℃;	83%

: 877-22-5
3-methoxysalicylic acid

: 917-54-4
methyllithium

: 703-98-0
1-(2-hydroxy-3-methoxyphenyl)ethanone

Conditions

Conditions	Yield
In tetrahydrofuran at 0 - 65℃; for 32h; Inert atmosphere;	83%
In tetrahydrofuran at 0 - 20℃; Inert atmosphere;

: 877-22-5
3-methoxysalicylic acid

: benzyl (3-methoxy-2-pentyloxyphenyl)carbonate

Conditions

Conditions	Yield
With diphenylphosphoranyl azide; triethylamine; benzyl alcohol In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; argon; toluene	82%

: 119072-55-8, 7188-38-7
tert-butylisonitrile

: 877-22-5
3-methoxysalicylic acid

: 104-88-1
4-chlorobenzaldehyde

: 2450-71-7
Propargylamine

: 1620025-59-3
N-(2-(tert-butylamino)-1-(4-chlorophenyl)-2-oxoethyl)-2-hydroxy-3-methoxy-N-(prop-2-yn-1-yl)benzamide

Conditions

Conditions	Yield
In methanol at 20℃; Ugi Condensation;	82%

...Expand

: 877-22-5
3-methoxysalicylic acid

: 392660-78-5
4-(7-nitro-3,4-dihydroisoquinoline-2(1H)-yl)butan-1-amine

: 1353004-56-4
2-hydroxy-3-methoxy-N-(4-(7-nitro-3,4-dihydroisoquinoline-2(1H)-yl)butyl)benzamide

Conditions

Conditions	Yield
Stage #1: 3-methoxysalicylic acid With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃; for 0.0833333h; Stage #2: 4-(7-nitro-3,4-dihydroisoquinoline-2(1H)-yl)butan-1-amine In tetrahydrofuran at 20℃;	79%

: 877-22-5
3-methoxysalicylic acid

: 67-64-1
acetone

: 2-oxopropyl 2-hydroxy-3-methoxybenzoate

Conditions

Conditions	Yield
With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In water at 60℃; for 8h;	79%

: 67-56-1
methanol

: 877-22-5
3-methoxysalicylic acid

: Mn(2+)*ClO4(1-)*6H2O

: 121-44-8
triethylamine

: 1402833-30-0
C17H18MnO10(1-)*C6H16N(1+)

Conditions

Conditions	Yield
With air for 3h;	78%

...Expand

: 877-22-5
3-methoxysalicylic acid

: 100-44-7
benzyl chloride

: 210706-41-5
2-Benzyloxy-3-methoxy-benzoic acid benzyl ester

Conditions

Conditions	Yield
Stage #1: 3-methoxysalicylic acid; benzyl chloride With potassium carbonate In N,N-dimethyl-formamide Reflux; Inert atmosphere; Stage #2: In methanol at 20℃;	74%
With potassium carbonate In N,N-dimethyl-formamide at 95℃;

: 110-86-1
pyridine

: 877-22-5
3-methoxysalicylic acid

: 6156-78-1
manganese (II) acetate tetrahydrate

: C62H58Mn3N6O18*4H2O

Conditions

Conditions	Yield
With tetra-n-butylammonium permanganate for 48h;	72%

...Expand

: 877-22-5
3-methoxysalicylic acid

: 108-24-7
acetic anhydride

: 2554-82-7
2-acetoxy-3-methoxybenzoic acid

Conditions

Conditions	Yield
With phosphoric acid for 2h; Heating;	71%

: 877-22-5
3-methoxysalicylic acid

: 100-51-6
benzyl alcohol

: benzyl 2-hydroxy-3-methoxybenzoate

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃;	70%
With dicyclohexyl-carbodiimide In tetrahydrofuran at 20℃;	27%

: 877-22-5
3-methoxysalicylic acid

: 85272-31-7
di-tert-butylsilyl bis(trifluoromethanesulfonate)

: C16H24O4Si

Conditions

Conditions	Yield
With 2,6-dimethylpyridine In acetonitrile at 0 - 22℃; for 16h; Inert atmosphere;	70%

: 671207-19-5
N-((3R)-1-[(6-fluoro-2-naphthyl)methyl]pyrrolidin-3-yl)-2-piperidin-4-ylideneacetamide

: 877-22-5
3-methoxysalicylic acid

: 671204-59-4
N-{(3R)-1-[(6-fluoro-2-naphthyl)methyl]pyrrolidin-3-yl}-2-[1-(2-hydroxy-3-methoxybenzoyl)piperidin-4-ylidene]acetamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃;	67%

3-Methoxysalicylic acid Chemical Properties

The Molecular formula of 2-HYDROXY-m-ANISIC ACID(877-22-5): C₈H₈O₄
The Molecular Weight of 2-HYDROXY-m-ANISIC ACID(877-22-5): 168.15
The Molecular Structure of 2-HYDROXY-m-ANISIC ACID(877-22-5):

EINECS: 212-888-9
Melting point: 147-150 °C(lit.)
Boiling Point: 315.7 °C at 760 mmHg
Flash Point: 131.7 °C
Index of Refraction: 1.585
Molar Refractivity: 41.74 cm³
Molar Volume: 124.3 cm³
Polarizability: 16.54 10^-24 cm³
Surface Tension: 56.5 dyne/cm
Density: 1.351 g/cm³
Enthalpy of Vaporization: 58.8 kJ/mol
Vapour Pressure: 0.000182 mmHg at 25°C
BRN: 2209642
IUPAC Name: 2-hydroxy-3-methoxybenzoic acid
Synonyms: GUAIACOL-3-CARBOXYLIC ACID;3-METHOXYSALICYLIC ACID;3-METHOXYSALICYLIC ACID MONOHYDRATE;3-METHOXY-2-HYDROXYBENZOIC ACID;2-hydroxy-3-methoxy-benzoicaci;2-hydroxy-m-anisicaci;3-hydroxy-m-anisicacid;acideorthovanillique;

3-Methoxysalicylic acid Toxicity Data With Reference

ipr-rat LD50:2056 mg/kg

COREAF Comptes Rendus Hebdomadaires des Seances de l’Academie des Sciences. 243 (1956),609.

3-Methoxysalicylic acid Safety Profile

Moderately toxic by intraperitoneal route. When heated to decomposition it emits acrid smoke and fumes.
The Hazard Codes of 2-HYDROXY-m-ANISIC ACID(877-22-5):

Xi,Xn
The Risk Statements information of 2-HYDROXY-m-ANISIC ACID(877-22-5):
20/21/22: Harmful by inhalation, in contact with skin and if swallowed
36/37/38: Irritating to eyes, respiratory system and skin
The Safety Statements information of 2-HYDROXY-m-ANISIC ACID(877-22-5):
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
37/39: Wear suitable gloves and eye/face protection
WGK Germany: 3
RTECS: BZ4840000

Product Name

3-Methoxysalicylic acid

Synthetic route

3-Methoxysalicylic acid Chemical Properties

3-Methoxysalicylic acid Toxicity Data With Reference

3-Methoxysalicylic acid Safety Profile

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