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109622

Sigma-Aldrich

2-Methoxybenzaldehyde

98%

Synonym(s):

o-Anisaldehyde, Salicylaldehyde methyl ether

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About This Item

Linear Formula:
CH3OC6H4CHO
CAS Number:
135-02-4
Molecular Weight:
136.15
Beilstein/REAXYS Number:
606301
EC Number:
205-171-7
MDL number:
MFCD00003308
UNSPSC Code:
12352100
PubChem Substance ID:
24846928
NACRES:
NA.22

Quality Level

100

assay

98%

form

solid

bp

238 °C (lit.)

mp

34-40 °C (lit.)

density

1.127 g/mL at 25 °C (lit.)

SMILES string

[H]C(=O)c1ccccc1OC

InChI

1S/C8H8O2/c1-10-8-5-3-2-4-7(8)6-9/h2-6H,1H3

InChI key

PKZJLOCLABXVMC-UHFFFAOYSA-N

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General description

2-Methoxybenzaldehyde is used as a starting material to synthesize corrosion-inhibiting Schiff bases. Also used as a flavor and fragrance ingredient.

Application

2-Methoxybenzaldehyde has been used to examine the acaricidal activity of Periploca sepium oil and its active component against Tyrophagus putrescentiae.
2-Methoxybenzaldehyde has been used to obtain good enantioselectivities using Cu(OAc)(2)-bis(oxazolines) via hydrogen bonding in asymmetric Henry reaction.

Biochem/physiol Actions

Naturally-occurring aromatic aldehyde with acaricidal activity. May condense with L-tryptophan in foods to form the corresponding phenolic tetrahydro-β-carboline-3-carboxylic acid which is a potent antioxidant.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

244.4 °F - closed cup

flash_point_c

118 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Eun-Young Jeong et al.
Journal of food protection, 75(1), 118-122 (2012-01-10)
The aim of this study was to examine the acaricidal activity of Periploca sepium oil and its active component against Tyrophagus putrescentiae. Based on its 50% lethal dose (LD(50) ) value, P. sepium oil (8.45 μg/cm(2)) was highly active against
Ninghua Yin et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 153, 1-5 (2015-08-19)
A facile fluorescence switch with Schiff base units was designed and achieved by nucleophilic addition and dehydration reaction. The fluorescence of the probe can be regulated by metal ions (Al(3+) and Cu(2+)). The whole process shows that the weak fluorescence
Olga V Kupriyanova et al.
Drug testing and analysis, 12(8), 1154-1170 (2020-05-18)
N-(2-Methoxybenzyl)-2,5-dimethoxyphenethylamines (NBOMes) are synthetic phenethylamine derivatives emerging on the global drug market and reported to be associated with untoward effects in people who use drugs. Its action involves agonism at serotonin 5-HT2A receptors, affecting cognitive and behavioral processes. However, certain
Zhi-Huai Li et al.
Chirality, 24(12), 1092-1095 (2012-09-25)
Immobilized Cu(OAc)(2)-bis(oxazolines) via hydrogen bonding by SBA-15 was applied to asymmetric Henry reaction, and good enantioselectivities were obtained (up to 83% ee) between 2-methoxybenzaldehyde and CH(3)NO(2) in isopropyl alcohol (iPrOH). The catalyst could be reused seven times without any obvious
Chao-Bin Xue et al.
Bioorganic & medicinal chemistry, 15(5), 2006-2015 (2007-01-30)
Phenoloxidase (PO), also known as tyrosinase, is a key enzyme in insect development, responsible for catalyzing the hydroxylation of tyrosine into o-diphenols and the oxidation of o-diphenols into o-quinones. Inhibition of PO may provide a basis for novel environmentally friendly

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