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3-Methoxysalicylic acid

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Name

3-Methoxysalicylic acid

EINECS 212-888-9
CAS No. 877-22-5 Density 1.351 g/cm3
PSA 66.76000 LogP 1.09900
Solubility N/A 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 N/A Appearance beige powder
Safety 26-37/39-36 Risk Codes 36/37/38-20/21/22
Molecular Structure Molecular Structure of 877-22-5 (3-Methoxysalicylic acid) Hazard Symbols IrritantXi,HarmfulXn
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;

Article Data 28

3-Methoxysalicylic acid Synthetic route

1521-38-6

2,3-dimethoxybenzoic acid

877-22-5

3-methoxysalicylic acid

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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

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
ConditionsYield
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
ConditionsYield
anschliessendes Behandeln mit CO2;
90-05-1

2-methoxy-phenol

877-22-5

3-methoxysalicylic acid

Conditions
ConditionsYield
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
ConditionsYield
With dimethyl sulfoxide for 0.166667h;

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 cm
Molar Volume: 124.3 cm
Polarizability: 16.54 10-24 cm
Surface Tension: 56.5 dyne/cm 
Density: 1.351 g/cm
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

1.   

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
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