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Sigma-Aldrich

3-Methoxyphenol

96%

Synonym(s):

3-Hydroxyanisol, Resorcinol monomethyl ether

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About This Item

Linear Formula:
CH3OC6H4OH
CAS Number:
150-19-6
Molecular Weight:
124.14
Beilstein:
1209898
EC Number:
205-754-6
MDL number:
MFCD00002267
UNSPSC Code:
12352100
PubChem Substance ID:
24859737
NACRES:
NA.22

Quality Level

100

Assay

96%

form

liquid

refractive index

n20/D 1.552 (lit.)

bp

113-115 °C/5 mmHg (lit.)

density

1.131 g/mL at 25 °C (lit.)

SMILES string

COc1cccc(O)c1

InChI

1S/C7H8O2/c1-9-7-4-2-3-6(8)5-7/h2-5,8H,1H3

InChI key

ASHGTJPOSUFTGB-UHFFFAOYSA-N

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Application

3-Methoxyphenol was used in synthesis of:
  • C(4) symmetric calix[4]resorcinarene
  • 2-nitroso-5-methoxyphenol
  • 6-methoxy-2(3H)-benzoxazolone

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Skin Irrit. 2

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

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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Alejandro Cordero Vargas et al.
Organic letters, 5(20), 3717-3719 (2003-09-26)
[reaction: see text] A short synthesis of (+/-)-10-norparvulenone and (+/-)-O-methylasparvenone was developed starting from commercially available m-methoxyphenol, hinging on a xanthate-mediated addition-cyclization sequence for the construction of the alpha-tetralone subunit.
L G Fenoll et al.
Biophysical chemistry, 84(1), 65-76 (2000-03-21)
Tyrosinase hydroxylates 3-hydroxyanisole in the 4-position. The reaction product accumulates in the reaction medium with a lag time (tau) which diminishes with increasing concentrations of enzyme and lengthens with increasing concentrations of substrate, thus fulfilling all the predictions of the
Mario C Foti et al.
The Journal of organic chemistry, 73(6), 2408-2411 (2008-02-26)
The m-methoxy group is normally electron-withdrawing (EW), sigma(m) = +0.12, sigma(m+) = +0.05. The strong EW activity of a phenoxyl radical's O* atom causes the m-methoxy group to become electron-donating (ED), sigma(m)(+) = -0.14. In valence bond terms, this can
Improved procedures for the preparation of 2-nitro-5-methoxyphenol and 6-methoxy-2 (3H)-benzoxazolone from 3-methoxyphenol.
Maleski RJ.
Synthetic Communications, 23(3), 343-348 (1993)
L G Fenoll et al.
Biological chemistry, 381(4), 313-320 (2000-06-06)
The relationship between the structure and activity of meta- and para-hydroxylated monophenols was studied during their tyrosinase-catalysed hydroxylation and the rate-limiting steps of the reaction mechanism were identified. The para-hydroxylated substrates permit us to study the effect of a substituent
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