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4421-08-3

Basic Information
CAS No.: 4421-08-3
Name: 4-Hydroxy-3-methoxybenzonitrile
Article Data: 81
Molecular Structure:
Molecular Structure of 4421-08-3 (4-Hydroxy-3-methoxybenzonitrile)
Formula: C8H7NO2
Molecular Weight: 149.149
Synonyms: 2-Methoxy-4-cyanophenol;3-Methoxy-4-hydroxybenzonitrile;4-Cyano-2-methoxyphenol;NSC 158285;
EINECS: 224-589-0
Density: 1.245 g/cm3
Melting Point: 85-87 °C(lit.)
Boiling Point: 291.559 °C at 760 mmHg
Flash Point: 130.131 °C
Appearance: beige crystalline powder
Hazard Symbols: HarmfulXn
Risk Codes: 20/21/22-36/37/38
Safety: 26-36/37/39
PSA: 53.25000
LogP: 1.27248
Synthetic route
121-33-5

vanillin

4421-08-3

3-methoxy-4-hydroxybenzonitrile

Conditions
ConditionsYield
With phenoxyamine hydrochloride In methanol; aq. phosphate buffer; water-d2 at 60℃; for 8h; pH=6.5;99%
With iron(III) chloride; hydroxylamine hydrochloride In N,N-dimethyl-formamide for 3h; Reagent/catalyst; Reflux;98%
With copper(II) oxide; hydroxylamine hydrochloride In neat (no solvent) for 0.0194444h; Mechanism; Reagent/catalyst; Microwave irradiation; Green chemistry;98%
2874-33-1

vanillin oxime

4421-08-3

3-methoxy-4-hydroxybenzonitrile

Conditions
ConditionsYield
With iron(III) chloride; silica gel In neat (no solvent) at 110℃; for 1.5h; Catalytic behavior; Concentration; Temperature; Green chemistry;98%
With silica gel for 0.0166667h; microwave irradiation;95%
With hydroxylamine hydrochloride; phosphorus pentoxide; silica gel for 0.0166667h; microwave irradiation;95%

vanillin oxime hydrochloride

4421-08-3

3-methoxy-4-hydroxybenzonitrile

Conditions
ConditionsYield
at 100℃; for 8h; Beckmann rearrangement;92%

potassiumhexacyanoferrate(II) trihydrate

203861-62-5

2-methoxy-4-iodophenol

4421-08-3

3-methoxy-4-hydroxybenzonitrile

Conditions
ConditionsYield
With tetrabutylammomium bromide; copper(II) acetate monohydrate In water at 180℃; for 22h;86%
203861-62-5

2-methoxy-4-iodophenol

potassium ferrocyanide

4421-08-3

3-methoxy-4-hydroxybenzonitrile

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 130℃; for 10h; Schlenk technique;86%
2024-83-1

veratronitrile

A

4421-08-3

3-methoxy-4-hydroxybenzonitrile

B

52805-46-6

2-methoxy-5-cyanophenol

Conditions
ConditionsYield
With sodium methylate; 1-dodecylthiol In N,N-dimethyl-formamide at 100℃; for 1h;A 83%
B 17%
1196-92-5

Vanillylamin

4421-08-3

3-methoxy-4-hydroxybenzonitrile

Conditions
ConditionsYield
With ammonium hydroxide; oxygen In tert-Amyl alcohol at 110℃; under 2250.23 Torr; for 15h; Autoclave; Green chemistry;83%
134283-49-1

(E)-4-hydroxy-3-methoxybenzaldehyde oxime

4421-08-3

3-methoxy-4-hydroxybenzonitrile

Conditions
ConditionsYield
at 120℃; for 2.5h; Beckmann rearrangement; Heating;73%
115109-49-4

2-(2-methoxy-4-cyanophenoxy)-acetic acid

4421-08-3

3-methoxy-4-hydroxybenzonitrile

Conditions
ConditionsYield
Stage #1: 2-(2-methoxy-4-cyanophenoxy)-acetic acid With triethylamine In N,N-dimethyl-formamide; toluene for 3h; Curtius rearrangement; Heating;
Stage #2: With potassium hydroxide; glycerol In ethanol; N,N-dimethyl-formamide; toluene for 2h; Heating; Further stages.;
70%
2150-38-1

methyl 3,4-dimethoxybenzoate

A

17345-61-8

3,4-dihydroxybenzonitrile

B

4421-08-3

3-methoxy-4-hydroxybenzonitrile

Conditions
ConditionsYield
With sodium hexamethyldisilazane In tetrahydrofuran at 185℃; for 24h;A 63%
B 23%
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Specification

The IUPAC name of Benzonitrile,4-hydroxy-3-methoxy- is 4-hydroxy-3-methoxybenzonitrile. With the CAS registry number 4421-08-3, it is also named as m-Anisonitrile, 4-hydroxy-. The product's categories are aromatic nitriles; anisoles, alkyloxy compounds & phenylacetates; nitriles; phenols; nitrogen compounds. In addition, it is beige crystalline powder.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.18; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.18; (4)ACD/LogD (pH 7.4): 1.05; (5)ACD/BCF (pH 5.5): 4.65; (6)ACD/BCF (pH 7.4): 3.44; (7)ACD/KOC (pH 5.5): 104.45; (8)ACD/KOC (pH 7.4): 77.14; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.568; (13)Molar Refractivity: 39.21 cm3; (14)Molar Volume: 119.7 cm3; (15)Polarizability: 15.54×10-24 cm3; (16)Surface Tension: 55.4 dyne/cm; (17)Enthalpy of Vaporization: 55.23 kJ/mol; (18)Vapour Pressure: 0.00111 mmHg at 25°C; (19)Rotatable Bond Count: 1; (20)Tautomer Count: 3; (21)Exact Mass: 149.047678; (22)MonoIsotopic Mass: 149.047678; (23)Topological Polar Surface Area: 53.2; (24)Heavy Atom Count: 11.

Preparation of Benzonitrile,4-hydroxy-3-methoxy-: It can be obtained by 4-hydroxy-3-methoxy-benzaldehyde with NH2OH*HCl and XY-zeolite at microwave irradiation in 1 min. The yield is 95%.

 

Uses of Benzonitrile,4-hydroxy-3-methoxy-: It reacts with acetic acid to get acetic acid 3-cyano-1-methoxy-6-oxo-cyclohexa-2,4-dienyl ester. This reaction which is Oxidation//acetoxylation needs reagent [(diacetoxy)iodo]benzene and solvent nitromethane. The reaction time is 10 min. The yield is 73 %.

When you are using this chemical, please be cautious about it as the following:
It is harmful by inhalation, in contact with skin and if swallowed. And it is 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 gloves and eye/face protection. 

People can use the following data to convert to the molecule structure. 
1. SMILES: N#Cc1cc(OC)c(O)cc1;
2. InChI: InChI=1/C8H7NO2/c1-11-8-4-6(5-9)2-3-7(8)10/h2-4,10H,1H3.