| Identification | More | [Name]
3-Methoxysalicylaldehyde | [CAS]
148-53-8 | [Synonyms]
2-HYDROXY-3-ANISALDEHYDE
2-HYDROXY-3-METHOXYBENZALDEHYDE
2-HYDROXY-M-ANISALDEHYDE
2-VANILLIN
3-METHOXY-2-HYDROXYBENZALDEHYDE
3-METHOXYSALICYLALDEHYDE
AKOS BBS-00003149
LABOTEST-BB LT00052811
O-VANILLIN
TIMTEC-BB SBB000109
2-hydroxy-3-methoxy-benzaldehyd
2-hydroxy-m-anisaldehyd
6-Formyl-2-methoxyphenol
6-Formylguaiacol
m-Anisaldehyde, 2-hydroxy-
Ortho vanillin
Orthovanilline
o-Vanilline
Oxy-2 methoxy-3 benzaldehyde
oxy-2methoxy-3benzaldehyde | [EINECS(EC#)]
205-715-3 | [Molecular Formula]
C8H8O3 | [MDL Number]
MFCD00003322 | [Molecular Weight]
152.15 | [MOL File]
148-53-8.mol |
| Chemical Properties | Back Directory | [Appearance]
Pale yellow to brown low melting solid | [Melting point ]
40-42 °C (lit.) | [Boiling point ]
265-266 °C (lit.) | [density ]
1.2143 (rough estimate) | [refractive index ]
1.4945 (estimate) | [Fp ]
>230 °F
| [storage temp. ]
Store below +30°C. | [solubility ]
Chloroform (Sparingly), Methanol (Slightly) | [form ]
Low Melting Solid | [pka]
pK1:7.912 (25°C) | [color ]
Pale yellow to brown | [Water Solubility ]
slightly soluble | [Sensitive ]
Air Sensitive | [BRN ]
471913 | [Stability:]
Hygroscopic | [InChI]
1S/C8H8O3/c1-11-7-4-2-3-6(5-9)8(7)10/h2-5,10H,1H3 | [InChIKey]
JJVNINGBHGBWJH-UHFFFAOYSA-N | [SMILES]
COc1cccc(C=O)c1O | [LogP]
1.370 | [CAS DataBase Reference]
148-53-8(CAS DataBase Reference) | [NIST Chemistry Reference]
Benzaldehyde, 2-hydroxy-3-methoxy-(148-53-8) | [EPA Substance Registry System]
148-53-8(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
S36:Wear suitable protective clothing .
S24/25:Avoid contact with skin and eyes .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S27:Take off immediately all contaminated clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [RTECS ]
CU6530000
| [F ]
10-23 | [TSCA ]
Yes | [HS Code ]
29124900 | [Storage Class]
13 - Non Combustible Solids | [Hazard Classifications]
Eye Irrit. 2 |
| Hazard Information | Back Directory | [Chemical Properties]
Pale yellow to brown low melting solid | [Uses]
A positional isomer of Vanillin. o-Vanillin is a more potent antioxidant than Vanillin. | [Definition]
ChEBI: A member of the class of benzaldehydes that is salicylaldehyde substituted by a methoxy group at position 3. | [Hazard]
ortho-Vanillin is harmful if ingested, irritating to eyes, skin and respiratory system, but has an unmistakable high LD50 of 1330 mg/kg in mice.
| [Biochem/physiol Actions]
o-Vanillin induces DNA damage as detected by comet assay. | [Synthesis]
GENERAL METHOD: A mixed solution of 3-methoxy-2-(trimethylsilyl)phenyl trifluoromethanesulfonate (53 μL, 0.20 mmol) with N-formylpiperidine (2.0 mmol) in acetonitrile (1.4 mL) was added to tetrabutylammonium fluoride (TBAF, 1.0 M acetonitrile solution, 0.60 mL, 0.60 mmol) under argon protection at room temperature. After the reaction mixture was stirred at the same temperature for 3 h, water (0.1 mL) was added. Subsequently, the reaction mixture was concentrated under reduced pressure. The residue was purified by fast silica gel column chromatography with the eluent ethyl acetate/hexane (1/20 to 1/8 containing 2% dichloromethane) to afford the target products 1-(3-methoxyphenyl)piperidine and o-vanillin. | [References]
[1] Tetrahedron, 2012, vol. 68, # 1, p. 179 - 189 |
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