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3-Methoxyphenol

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Name

3-Methoxyphenol

EINECS 205-754-6
CAS No. 150-19-6 Density 1.109 g/cm3
PSA 29.46000 LogP 1.40080
Solubility slightly soluble in water Melting Point -17 °C
Formula C7H8O2 Boiling Point 244.3 °C at 760 mmHg
Molecular Weight 124.139 Flash Point 119.1 °C
Transport Information UN 2810 6.1/PG 3 Appearance Clear pink red liquid
Safety 26-36/37/39 Risk Codes 20/21/22-36/38-41-36/37/38
Molecular Structure Molecular Structure of 150-19-6 (3-Methoxyphenol) Hazard Symbols HarmfulXn
Synonyms

m-Hydroxyanisol;m-Hydroxyanisole;m-Methoxyphenol;Phenol,m-methoxy- (8CI);1-Hydroxy-3-methoxybenzene;3-Hydroxyanisole;NSC 21735;Resorcinol methyl ether;Resorcinol monomethylether;m-Guaiacol;

Article Data 266

3-Methoxyphenol Synthetic route

3-methoxybenzenediazonium tetrafluoroborate

150-19-6

O-methylresorcine

Conditions
ConditionsYield
With water Heating;100%
10365-98-7

3-methoxyphenylboronic acid

150-19-6

O-methylresorcine

Conditions
ConditionsYield
With oxygen; triethylamine In 2-methyltetrahydrofuran at 20℃; under 760.051 Torr; for 24h; Green chemistry;99%
With pyrene-1,6-dione; oxygen; isopropyl alcohol at 20℃; under 760.051 Torr; for 40h; Irradiation; Green chemistry;98%
With C18H28Cl2CuN2O4 In water at 26℃; for 0.333333h;96%

C13H23NOSi

150-19-6

O-methylresorcine

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride; dihydrogen peroxide; potassium hydrogencarbonate In tetrahydrofuran; methanol; water at 20℃; for 16h; Inert atmosphere;99%
766-85-8

3-methoxy-1-iodobenzene

150-19-6

O-methylresorcine

Conditions
ConditionsYield
With β-D-glucose; copper(II) acetate monohydrate; potassium hydroxide In water; dimethyl sulfoxide at 20 - 120℃; for 24h;99%
With copper(I) oxide; water; potassium carbonate; Sucrose at 140℃; for 18h; Sealed tube; Inert atmosphere;92%
With copper(l) iodide; triethanolamine; tetrabutylammomium bromide; water; potassium hydroxide at 120℃; for 24h; Inert atmosphere;89%
151-10-0

1,3-Dimethoxybenzene

150-19-6

O-methylresorcine

Conditions
ConditionsYield
With 1,3-dimethyl-2-imidazolidinone; sodium hexamethyldisilazane In tetrahydrofuran at 185℃; for 12h; further reagent: LDA;98%
With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydride; N-methylaniline In diethyl ether; xylene at 120℃; for 6.5h;95%
With lithium thioethoxide In N,N-dimethyl-formamide at 135℃; for 0.25h; Inert atmosphere; Microwave irradiation;90%
2398-37-0

3-methoxyphenyl bromide

150-19-6

O-methylresorcine

Conditions
ConditionsYield
With potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos In 1,4-dioxane; water at 100℃; for 1.5h;98%
With copper(I) oxide; tetra(n-butyl)ammonium hydroxide; 1,10-phenanthroline-4,7-diol In water at 110℃; for 24h; Inert atmosphere; Schlenk technique; Sealed tube; Green chemistry;96%
With copper(l) iodide; potassium hydroxide In water at 120℃; for 12h; Inert atmosphere;90%
77-78-1

dimethyl sulfate

108-46-3

recorcinol

150-19-6

O-methylresorcine

Conditions
ConditionsYield
With tetrabutylammomium bromide; sodium hydroxide In water; toluene at 20℃; Solvent;96.8%
With sodium hydrogencarbonate at 50℃; for 1h; Williamson synthesis;80%
With sodium hydrogencarbonate at 60℃; for 1h;79%
5451-83-2

acetic acid 3-methoxyphenyl ester

150-19-6

O-methylresorcine

Conditions
ConditionsYield
With silica-supported phosphomolybdic acid In methanol at 20℃; for 2h;96%
With potassium carbonate In methanol at 20℃;50%
With methanol; potassium carbonate at 20℃;50%
10365-98-7

3-methoxyphenylboronic acid

7722-84-1

dihydrogen peroxide

150-19-6

O-methylresorcine

Conditions
ConditionsYield
With ammonium bicarbonate In water at 20℃; for 2h; Schlenk technique;96%

C10H12O4

150-19-6

O-methylresorcine

Conditions
ConditionsYield
With sodium tetrahydroborate In ethanol at 20℃; for 1h;95%

3-Methoxyphenol Consensus Reports

Reported in EPA TSCA Inventory.

3-Methoxyphenol Specification

The Resorcinol monomethyl ether is an organic compound with the formula C7H8O2. The IUPAC name of this chemical is 3-methoxyphenol. With the CAS registry number 150-19-6, it is also named as 1-Hydroxy-3-methoxybenzene. The product's category is Aromatic Ethers. It is clear pink red liquid which is slightly soluble in water and stable under normal temperature and pressure. Additionally, thsi chemical should be sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.52; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.52; (4)ACD/LogD (pH 7.4): 1.51; (5)ACD/BCF (pH 5.5): 8.35; (6)ACD/BCF (pH 7.4): 8.3; (7)ACD/KOC (pH 5.5): 158.97; (8)ACD/KOC (pH 7.4): 157.95; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.534; (13)Molar Refractivity: 34.81 cm3; (14)Molar Volume: 111.8 cm3; (15)Polarizability: 13.8×10-24 cm3; (16)Surface Tension: 38.6 dyne/cm; (17)Enthalpy of Vaporization: 50.08 kJ/mol; (18)Vapour Pressure: 0.0196 mmHg at 25°C; (19)Rotatable Bond Count: 1; (20)Tautomer Count: 3; (21)Exact Mass: 124.05243; (22)MonoIsotopic Mass: 124.05243; (23)Topological Polar Surface Area: 29.5; (24)Heavy Atom Count: 9; (25)Complexity: 83.

Preparation of Resorcinol monomethyl ether: It can be obtained by 1,3-dimethoxy-benzene. This reaction needs reagent AlCl3 and NaI at temperature of 70-80 °C. The reaction time is 4.0 hours. The yield is 70%.

Uses of Resorcinol monomethyl ether: It can react with acetoacetic acid ethyl ester to get 7-methoxy-4-methyl-chromen-2-one. This reaction which is a kind of Pechmann condensation needs reagent [bmim]Cl*2AlCl3 at temperature of 30 °C. The reaction time is 10 min. The yield is 92%.

When you are using this chemical, please be cautious about it as the following:
It is not only harmful by inhalation, in contact with skin and if swallowed, but also irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection.

People can use the following data to convert to the molecule structure. 
1. SMILES:Oc1cccc(OC)c1
2. InChI:InChI=1/C7H8O2/c1-9-7-4-2-3-6(8)5-7/h2-5,8H,1H3
3. InChIKey:ASHGTJPOSUFTGB-UHFFFAOYAE

The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TCLo inhalation 230ug/m3/22W (0.23mg/m3) BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: HEADACHE

BEHAVIORAL: IRRITABILITY
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 37(3), Pg. 108, 1972.
mammal (species unspecified) LD50 oral 597mg/kg (597mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 45(10), Pg. 16, 1980.
mammal (species unspecified) LD50 skin 682mg/kg (682mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 45(10), Pg. 16, 1980.
mouse LC50 inhalation 11500mg/m3/4H (11500mg/m3)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 105, 1982.
mouse LD50 intraperitoneal 320mg/kg (320mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: TREMOR

BEHAVIORAL: ATAXIA
Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 46, Pg. 185, 1957.
mouse LD50 oral 312mg/kg (312mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 37(3), Pg. 108, 1972.
rat LC50 inhalation 11500mg/m3/4H (11500mg/m3)   "Toxicometric Parameters of Industrial Toxic Chemicals Under Single Exposure," Izmerov, N.F., et al., Moscow, Centre of International Projects, GKNT, 1982Vol. -, Pg. 105, 1982.
rat LD50 oral 597mg/kg (597mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 37(3), Pg. 108, 1972.
rat LD50 skin 682mg/kg (682mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 37(3), Pg. 108, 1972.

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