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o-Anisidine
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Name

o-Anisidine

 EINECS 201-963-1
CAS No. 90-04-0 Density 1.092 g/cm3
PSA 35.25000 LogP 1.85860
Solubility water: 13g/L (20 °C) Melting Point 3-6 °C
Formula C7H9NO Boiling Point 225 °C
Molecular Weight 123.155 Flash Point 107 °C
Transport Information UN 2431 6.1/PG 3 Appearance light red or light yellow oily liquid
Safety 53-45 Risk Codes 45-23/24/25-68
Molecular Structure Molecular Structure of 90-04-0 (o-Anisidine) Hazard Symbols ToxicT,IrritantXi
Synonyms

o-Anisidine;o-Anisidine(8CI);1-Amino-2-methoxybenzene;2-Aminoanisole;2-Aminomethoxybenzene;2-Methoxy-1-aminobenzene;2-Methoxyaniline;2-Methoxybenzenamine;2-Methoxyphenylamine;NSC 3122;o-Aminoanisole;o-Aminomethoxybenzene;o-Methoxyaniline;o-Methoxyphenylamine;

Article Data 321

o-Anisidine Synthetic route

578-57-4

2-bromoanisole

90-04-0

2-methoxy-phenylamine

Conditions
ConditionsYield
With bis(tri-ortho-tolylphosphine)palladium(0); (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine; ammonia; sodium t-butanolate In 1,4-dioxane at 100℃; for 12h; Inert atmosphere;95%
With ammonium hydroxide In water at 20℃; for 9h; Green chemistry;94%
With [N,N'-bis(5-sulfonatosalicylidene)-1,2-diaminoethane]copper disodium salt; ammonia; sodium hydroxide In water at 120℃; for 12h; sealed tube;90%
91-23-6

2-Nitroanisole

90-04-0

2-methoxy-phenylamine

Conditions
ConditionsYield
With borane-ammonia complex In methanol; water at 20℃; for 0.0833333h;99%
With hydrogen In neat (no solvent) at 59.84℃; under 30003 Torr; for 3.5h; Autoclave;99.1%
With sodium tetrahydroborate In methanol; water at 20℃; for 0.0833333h; Sealed tube; Green chemistry;99%
529-28-2

4-iodoanisol

90-04-0

2-methoxy-phenylamine

Conditions
ConditionsYield
With ammonium hydroxide In water at 20℃; for 9h; Green chemistry;95%
With ammonium hydroxide; caesium carbonate In acetonitrile for 7h; Reflux; Green chemistry;91%
With iron(III) oxide; sodium hydroxide; copper(l) iodide; ammonia In ethanol; water at 90℃; for 16h;90%
766-51-8

2-Chloroanisole

90-04-0

2-methoxy-phenylamine

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium (0); lithium hexamethyldisilazane; CyJohnPhos; 1,1,1-triphenylsilylamine In toluene at 100℃; for 17h;98%
With bis(tri-ortho-tolylphosphine)palladium(0); (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine; ammonia; sodium t-butanolate In 1,4-dioxane at 100℃; for 24h; Inert atmosphere;89%
With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; N-[2-(di(1-adamantyl)phosphino)phenyl]morpholine; ammonia; sodium t-butanolate In 1,4-dioxane at 20℃; for 14h; Inert atmosphere; chemoselective reaction;88%
20442-97-1

2-methoxylphenyl azide

90-04-0

2-methoxy-phenylamine

Conditions
ConditionsYield
With zinc(II) tetrahydroborate In 1,2-dimethoxyethane for 3h; Ambient temperature;89%
Stage #1: 2-methoxylphenyl azide With hydrazine hydrate for 0.166667h; Inert atmosphere;
Stage #2: for 12h; Irradiation; chemoselective reaction;		87%
With water for 5h; Inert atmosphere; UV-irradiation; Sealed tube; chemoselective reaction;66%
766-51-8

2-Chloroanisole

A

7287-75-4

N,N-bis(2-methoxyphenyl)amine

B

90-04-0

2-methoxy-phenylamine

Conditions
ConditionsYield
With ((+/-)-binap)Ni[P(OPh)3]2*2PhCH3; ammonia; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In 1,4-dioxane at 120℃; for 18h; Inert atmosphere; Sealed tube;A n/a
B 70%
With C28H30Cl5N3Pd; ammonia; lithium isopropoxide; sodium t-butanolate In 1,4-dioxane at 100℃; for 2h; Reagent/catalyst; Inert atmosphere; Schlenk technique;A n/a
B 68%
13513-82-1

1-(2-methoxyphenyl)ethanol

90-04-0

2-methoxy-phenylamine

Conditions
ConditionsYield
With sodium azide; trifluoroacetic acid In hexane at 40℃; for 4h; Sealed tube;60%
With sodium azide; methanesulfonic acid; trifluoroacetic acid In hexane at 40℃; for 10h;60%
91-23-6

2-Nitroanisole

A

4342-43-2

2-methoxycyclohexanamine

B

90-04-0

2-methoxy-phenylamine

Conditions
ConditionsYield
With hydrogen In ethanol at 100℃; under 22502.3 Torr; for 10h; Autoclave;
100-66-3

methoxybenzene

A

90-04-0

2-methoxy-phenylamine

B

104-94-9

4-methoxy-aniline

Conditions
ConditionsYield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; tert-butyl N-tosyloxycarbamate at 20℃; for 12h; chemoselective reaction;A 37%
B 37%
With titanium; sulfuric acid; hydroxylamine In water; acetonitrile at 40℃; Electrochemical reaction;
With sulfuric acid; titanium(IV); hydroxylamine; acetic acid In water at 40℃; Electrochemical reaction; Inert atmosphere;
91-23-6

2-Nitroanisole

67-63-0

isopropyl alcohol

A

C10H21NO

B

90-04-0

2-methoxy-phenylamine

Conditions
ConditionsYield
With hydrogen In water at 130℃; under 3750.38 Torr; for 10h; Molecular sieve; Autoclave;

o-Anisidine Specification

The o-Anisidine with CAS registry number of 90-04-0 is also known as 1-Amino-2-methoxybenzene. The IUPAC name is 2-Methoxyaniline. It belongs to product categories of Intermediates of Dyes and Pigments; Intermediates. Its EINECS registry number is 201-963-1. In addition, the formula is C7H9NO and the molecular weight is 123.15. This chemical is a light red or light yellow oily liquid and should be stored in dry, ventilated place without sunlight, moisture and heat.

Physical properties about o-Anisidine are: (1)XLogP3: 1.2; (2)H-Bond Donor: 1; (3)H-Bond Acceptor: 2; (4)Rotatable Bond Count: 1; (5)Exact Mass: 123.068414; (6)MonoIsotopic Mass: 123.068414; (7)Topological Polar Surface Area: 35.2; (8)Heavy Atom Count: 9; (9)Complexity: 85; (10)Covalently-Bonded Unit Count: 1.

Preparation of o-Anisidine: it is prepared by reduction of o-nitrophenyl ether. The o-nitrophenyl ether can be obtained by oxy reaction of o-chlorotoluene. Sodium sulfide or iron can be used as reducing agent. The process is as follows. The first step at 70-78 °C and the second step at 118-120 °C.

(1) C6H4NClO2+CH3OH+NaOH→C7H7NO3+NaCl+H2O (2) 4C7H7NO3+6Na2S+7H2O→C7H6NO+3Na2S3O3+6NaOH

Uses of o-Anisidine: it can be used for making dyes, azoic dyes and naphthol as-ol and other dyes. It also can be used as dyes intermediate. Besides, it is used as reagent for testing codeine and alkaloid. What's more, this chemical is used to prepare pyridine-2-carboxylic acid o-anisidide by reaction with pyridine-2-carbonyl chloride. The reation needs reagent pyridine and the yield is about 40%.

o-Anisidine is used to prepare pyridine-2-carboxylic acid o-anisidide by reaction with pyridine-2-carbonyl chloride.

When you are using this chemical, please be cautious about it. As a chemical, it is toxic by inhalation, in contact with skin and if swallowed. It has possible risk of irreversible effects and may cause cancer. During using it, obtain special instructions before use. In case of accident or if you feel unwell seek medical advice immediately.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: COC1=CC=CC=C1N
2. InChI: InChI=1S/C7H9NO/c1-9-7-5-3-2-4-6(7)8/h2-5H,8H2,1H3
3. InChIKey: VMPITZXILSNTON-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 422mg/kg (422mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
mouse LD50 oral 1400mg/kg (1400mg/kg) KIDNEY, URETER, AND BLADDER: OTHER CHANGES

BLOOD: NORMOCYTIC ANEMIA

BLOOD: OTHER CHANGES		 IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. Vol. 27, Pg. 63, 1982.
rabbit LD50 oral 870mg/kg (870mg/kg) KIDNEY, URETER, AND BLADDER: OTHER CHANGES

BLOOD: OTHER CHANGES

BLOOD: NORMOCYTIC ANEMIA		 IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. Vol. 27, Pg. 63, 1982.
rat LD50 oral 1150mg/kg (1150mg/kg)   Trudy Leningradskogo Sanitarno-Gigienicheskogo Meditsinskogo Instituta. Vol. 128, Pg. 14, 1979.

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