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3-Methoxysalicylaldehyde

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CAS:148-53-8
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CAS:148-53-8
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3-Methoxysalicylaldehyde manufacturers

3-Methoxysalicylaldehyde Basic information
Product Name:3-Methoxysalicylaldehyde
Synonyms:TIMTEC-BB SBB000109;2-Hydroxy-3-methoxybenzaldehyde, 2-Hydroxy-m-anisaldehyde, 3-Methoxysalicylaldehyde;2-HYDROXY-3-METHOXYBENZALDEHYDE / O-VANILLIN;Adjacent vanillin;3-Methoxysalicyladehyde;NC 005;NSC 2150;2-Hydroxy-3-Methoxybenzaldehyde-13C6,d3
CAS:148-53-8
MF:C8H8O3
MW:152.15
EINECS:205-715-3
Product Categories:Aromatics;Aldehydes;Building Blocks;C8;Carbonyl Compounds;Chemical Synthesis;Aromatic Aldehydes & Derivatives (substituted);Organic Building Blocks;bc0001
Mol File:148-53-8.mol
3-Methoxysalicylaldehyde Structure
3-Methoxysalicylaldehyde Chemical Properties
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)
pkapK1:7.912 (25°C)
form Low Melting Solid
color Pale yellow to brown
Water Solubility slightly soluble
Sensitive Air Sensitive
BRN 471913
Stability:Hygroscopic
InChI1S/C8H8O3/c1-11-7-4-2-3-6(5-9)8(7)10/h2-5,10H,1H3
InChIKeyJJVNINGBHGBWJH-UHFFFAOYSA-N
SMILESCOc1cccc(C=O)c1O
LogP1.370
CAS DataBase Reference148-53-8(CAS DataBase Reference)
NIST Chemistry ReferenceBenzaldehyde, 2-hydroxy-3-methoxy-(148-53-8)
EPA Substance Registry SystemBenzaldehyde, 2-hydroxy-3-methoxy- (148-53-8)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-36/37/38
Safety Statements 23-36-24/25-36/37/39-27-26
WGK Germany 3
RTECS CU6530000
10-23
TSCA TSCA listed
HS Code 29124900
Storage Class13 - Non Combustible Solids
Hazard ClassificationsEye Irrit. 2
MSDS Information
ProviderLanguage
3-Methoxysalicylaldehyde English
SigmaAldrich English
ACROS English
ALFA English
3-Methoxysalicylaldehyde Usage And Synthesis
Chemical PropertiesPale yellow to brown low melting solid
Useso-Vanillin has been used to study the solvent-free reaction between o-vanillin and p-toluidine using NMR, DSC and XRD analysis. It was used in the synthesis of new ligand for Fe(III) and Al(lII).
Useso-Vanillin has been used to study the solvent-free reaction between o-vanillin and p-toluidine using NMR, DSC and XRD analysis. It was used in the synthesis of new ligand for Fe(III) and Al(lII). It is also used in the study of mutagenesis and as a synthetic precursor for pharmaceuticals.
UsesA positional isomer of Vanillin. o-Vanillin is a more potent antioxidant than Vanillin.
DefinitionChEBI: A member of the class of benzaldehydes that is salicylaldehyde substituted by a methoxy group at position 3.
Hazardortho-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 Actionso-Vanillin induces DNA damage as detected by comet assay.
Synthesis
N-Formylpiperidine

2591-86-8

3-METHOXY-2-(TRIMETHYLSILYL)PHENYL TRIFLUOROMETHANESULFONATE,95.0+%(GC)

217813-03-1

3-Piperidinoanisole

32040-06-5

3-Methoxysalicylaldehyde

148-53-8

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
Tag:3-Methoxysalicylaldehyde(148-53-8) Related Product Information
Anisole 3,7-Dimethyl-7-hydroxyoctanal 3-Hydroxybenzaldehyde (Trifluoromethoxy)benzene Cuminaldehyde CHLOROPHOSPHONAZO III p-Anisaldehyde Ethyl vanillin Benzaldehyde Vanillin 3,5-Dimethoxybenzaldehyde 4-Hydroxybenzaldehyde o-Anisaldehyde 2,6-Dimethoxybenzaldehyde 4-Dimethylaminobenzaldehyde Veratraldehyde 3-Methoxybenzaldehyde Salicylaldehyde

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