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Cas Database |
| Name |
Methyl vanillate |
EINECS | 223-525-9 |
| CAS No. | 3943-74-6 | Density | 1.216 g/cm3 |
| PSA | 55.76000 | LogP | 1.18740 |
| Solubility | N/A | Melting Point |
64-67 °C(lit.) |
| Formula | C9H10O4 | Boiling Point | 286 °C at 760 mmHg |
| Molecular Weight | 182.176 | Flash Point | 120.2 °C |
| Transport Information | N/A | Appearance | pale yellow to beige powder and granules |
| Safety | 26-36-24/25 | Risk Codes | 36/37/38 |
| Molecular Structure |
|
Hazard Symbols |
 Xi
|
| Synonyms |
4-Hydroxy-3-methoxybenzoic acid methyl ester;Vanillic acid, methyl ester (8CI);Vanillic acid methyl ester;Methyl 3-methoxy-4-hydroxybenzoate;Methyl 4-hydroxy-3-methoxybenzoate;methyl 4-hydroxy-3-methoxy-benzoate;Vanillic acid, methyl ester;3-10-00-01410 (Beilstein Handbook Reference); |
Article Data | 74 |
Methyl vanillate Synthetic route
- 67-56-1
methanol
- 121-34-6
3-methoxy-4-hydroxybenzoic acid
- 3943-74-6
4-hydroxy-3-methoxybenzoic acid methyl ester
| Conditions | Yield |
|---|---|
| With hydrogenchloride for 12h; Reflux; | 100% |
| With hydrogenchloride In diethyl ether Fischer-Speier Esterification; Reflux; | 100% |
| With thionyl chloride at 0 - 20℃; Inert atmosphere; | 100% |
- 56441-97-5
methyl 4-(benzyloxy)-3-methoxybenzoate
- 3943-74-6
4-hydroxy-3-methoxybenzoic acid methyl ester
| Conditions | Yield |
|---|---|
| With hydrogen; palladium on activated charcoal In various solvent(s) at 20℃; under 760 Torr; for 6h; | 95% |
| Conditions | Yield |
|---|---|
| With perchloric acid; sodium percarbonate; vanadia for 2h; Cooling; | 94% |
| With 2,2':6,2''-terpyridine; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; sodium acetate; sodium hydroxide at 90℃; for 24h; Green chemistry; chemoselective reaction; | 83% |
| With 1-(ferrocenylbutyl)-4-(3-methylimidazolium) tetrafluoroborate; iodine; potassium carbonate at 50 - 60℃; for 22h; Inert atmosphere; | 40% |
| With oxygen; methylene blue at 10 - 15℃; for 144h; Mechanism; Irradiation; also with EtOH; also without irradiation in the presence of p-toluenesulfonic acid; | |
| With perchloric acid; dihydrogen peroxide; vanadia In water at 5℃; for 6h; oxidative esterification; | 83 % Chromat. |
- 1445-45-0
Trimethyl orthoacetate
- 121-34-6
3-methoxy-4-hydroxybenzoic acid
- 3943-74-6
4-hydroxy-3-methoxybenzoic acid methyl ester
| Conditions | Yield |
|---|---|
| microwave irradiation; | 90% |
| Conditions | Yield |
|---|---|
| With sulfuric acid; sodium hydrogencarbonate; mercury In methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate | 82% |
- 67-56-1
methanol
- 201230-82-2
carbon monoxide
- 90-05-1
2-methoxy-phenol
- 3943-74-6
4-hydroxy-3-methoxybenzoic acid methyl ester
| Conditions | Yield |
|---|---|
| With bis-triphenylphosphine-palladium(II) chloride; oxygen; potassium carbonate; potassium iodide at 100℃; under 6000.6 Torr; for 18h; | 76% |
| Conditions | Yield |
|---|---|
| With sodium hydroxide at 25℃; for 6h; | A 64% B n/a |
- 1135-24-6
(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid
A
- 3943-74-6
4-hydroxy-3-methoxybenzoic acid methyl ester
B
- 121-33-5
vanillin
C
- 84272-48-0
4-hydroxy-3-methoxybenzoylacetic acid
D
- 498-02-2
1-(3-methoxy-4-hydroxyphenyl)ethanone
| Conditions | Yield |
|---|---|
| With salcomine; oxygen In methanol at 25℃; under 7600 Torr; for 72h; | A 20% B 16% C n/a D n/a |
| With salcomine; oxygen In methanol at 25℃; under 7600 Torr; for 72h; Product distribution; also with following CH2N2/ether action, other products; | A 20% B 16% C n/a D n/a |
- 5368-81-0
methyl 3-methoxybenzoate
A
- 3943-74-6
4-hydroxy-3-methoxybenzoic acid methyl ester
B
- 6342-70-7
3-methoxymethylsalicylate
C
- 2905-82-0
methyl 5-methoxy-2-hydroxybenzoate
| Conditions | Yield |
|---|---|
| Stage #1: methyl 3-methoxybenzoate With 6,7-dichlorobenzo[d][1,2]dioxine-1,4-dione In chloroform at 50℃; for 24h; Stage #2: With water; sodium hydrogencarbonate In methanol at 50℃; for 1h; Inert atmosphere; Overall yield = 55 %; regioselective reaction; | A 20% B 18% C 17% |
- 186581-53-3, 908094-01-9
diazomethane
- 121-34-6
3-methoxy-4-hydroxybenzoic acid
- 3943-74-6
4-hydroxy-3-methoxybenzoic acid methyl ester
Methyl vanillate Chemical Properties
Molecular Formula: C9H10O4
Formula Weight: 182.17
EINECS: 223-525-9
Index of Refraction: 1.534
Molar Refractivity: 46.58 cm3
Molar Volume: 149.7 cm3
Surface Tension: 43.1 dyne/cm
Density: 1.216 g/cm3
Flash Point: 120.2 °C
Enthalpy of Vaporization: 54.61 kJ/mol
Boiling Point: 286 °C at 760 mmHg
Vapour Pressure: 0.00157 mmHg at 25 °C
Melting point: 64-67 °C(lit.)
Appearance: Pale yellow to beige powder and granules
Structure of Methyl vanillate (CAS NO.3943-74-6):
IUPAC Name: Methyl 4-hydroxy-3-methoxybenzoate
Canonical SMILES: COC1=C(C=CC(=C1)C(=O)OC)O
InChI: InChI=1S/C9H10O4/c1-12-8-5-6(9(11)13-2)3-4-7(8)10/h3-5,10H,1-2H3
InChIKey: BVWTXUYLKBHMOX-UHFFFAOYSA-N
Product Category of Methyl vanillate (CAS NO.3943-74-6): Fine Chemical & intermediates;Aromatic Esters
Methyl vanillate Toxicity Data With Reference
| 1. | ivn-mus LD50:180 mg/kg | CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#06782 . |
Methyl vanillate (CAS NO.3943-74-6) hasn't been listed as a carcinogen by NTP, IARC, ACGIH, or CA Prop 65. You can see actual entry in RTECS for complete information.
Methyl vanillate Safety Profile
Hazard Codes: 
Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-24/25
S24/25:Avoid contact with skin and eyes.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
Methyl vanillate Specification
Methyl vanillate , its cas register number is 3943-74-6. It also can be called Methyl 4-hydroxy-3-methoxybenzoate ; 4-Hydroxy-3-methoxybenzoic acid methyl ester ; and Vanillic acid, methyl ester . It should be stored in a cool, dry, well-ventilated area away from incompatible substances. It is hazardous, so the first aid measures and others should be known. Such as: When on the skin: first, should flush skin with plenty of water immediately for at least 15 minutes while removing contaminated clothing. Secondly, get medical aid. Or in the eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Then get medical aid soon. While, it's inhaled: Remove from exposure and move to fresh air immediately. Give artificial respiration while not breathing. When breathing is difficult, give oxygen. And as soon as to get medical aid. Then you have the ingesting of the product: If victim is conscious and alert, give 2-4 cupfuls of milk or water. Get medical aid immediately.
In addition, Methyl vanillate (CAS NO.3943-74-6) could be stable under normal temperatures and pressures. You must not take it with strong oxidants. And also prevent it to broken down into hazardous decomposition products: irritating and toxic fumes and gases.
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