120-71-8

Basic information

• Product Name: 2-Methoxy-5-methylaniline
• Synonyms: 2-Amino-4-methylphenolmethylether;2-Amino-p-cresol methyl ether;2-Amino-p-cresolmethylether;2-methoxy-5-methyl-benzenamin;2-Methoxy-5-methylbenzenamine;2-methoxy-5-methyl-Benzenamine;3-amino-para-cresol,methylether;4-Methyl-2-aminoanisole
• CAS NO: 120-71-8
• Molecular Formula: C₈H₁₁NO
• Molecular Weight: 137.18
• EINECS: 204-419-1
• Product Categories: Intermediates of Dyes and Pigments;Anilines, Aromatic Amines and Nitro Compounds
• Mol File: 120-71-8.mol
• Article Data: 25

Chemical Properties

• Melting Point: 50-52 °C(lit.)
• Boiling Point: 235 °C(lit.)
• Flash Point: >230 °F
• Appearance: Brown to black/Crystalline Chunks
• Density: 1.0252 (rough estimate)
• Vapor Density: 4.7 (vs air)
• Vapor Pressure: 0.0381mmHg at 25°C
• Refractive Index: 1.5647 (estimate)
• PKA: 4.66±0.10(Predicted)
• Water Solubility: Slightly soluble in hot water.
• BRN: 637071
• CAS DataBase Reference: 2-Methoxy-5-methylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methoxy-5-methylaniline(120-71-8)
• EPA Substance Registry System: 2-Methoxy-5-methylaniline(120-71-8)

Safety Data

• Hazard Codes: T,Xi
• Statements: 45-22
• Safety Statements: 53-45
• WGK Germany: 3
• RTECS: BZ6720000
• F: 9
• HazardClass: IRRITANT
• Hazardous Substances Data: 120-71-8(Hazardous Substances Data)

Usage

Reactivity Profile

2-Methoxy-5-methylaniline is sensitive to moisture and temperatures greater than 104°F. Incompatible with strong oxidizing agents .

Fire Hazard

2-Methoxy-5-methylaniline is nonflammable.

Potential Exposure

p-Cresidine is used as an intermediate in the production of various azodyes, printing inks, and pigments; including 11 dyes that are produced commercially in the United States. Human exposure to p-Cresidine occurs primarily through inhalation of

General Description

White to silver-gray odorless crystals.

Safety Profile

Confirmed carcinogen with experimental carcinogenic and neoplastigenic data. Moderately toxic by ingestion. A skin and eye irritant. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also ESTERS.

Shipping

UN2811 Toxic solids, organic, n.o.s., Hazard Class: 6.1; Labels: 6.1-Poisonous materials, Technical Name Required

Uses

p-Cresidine is a reagent used in the preparation of enaminones acting as anticonvulsants. Also used in the preparation of crescent oligoamides.

Air & Water Reactions

Insoluble in water.

Chemical Properties

brown to black crystalline chunks

Hazard

A possible carcinogen.

Chemical Properties

p-Cresidine is a white crystalline solid.

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides.

Carcinogenicity

p-Cresidine is reasonably anticipated to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in experimental animals.

InChI:InChI=1/C8H11NO/c1-6-5-7(9)3-4-8(6)10-2/h3-5H,9H2,1-2H3

Synthetic route

2-Methoxi-5-methylphenylazid (77721-47-2) → Cresidine (120-71-8)

Conditions	Yield
With lithium aluminium tetrahydride	100%
With lithium aluminium tetrahydride In diethyl ether

4-methoxy-3-nitrotoluene (119-10-8) → Cresidine (120-71-8)

Conditions	Yield
With palladium on carbon; hydrogen In ethanol at 20℃; under 28443.9 Torr; for 22h;	99%
With ammonium sulfide; ethanol
With hydrogenchloride; tin at 50℃;
With iron; acetic acid

2-Nitro-2'-methoxy-5'-methyl-azobenzol (29530-48-1) → 1,2-diamino-benzene (95-54-5) + Cresidine (120-71-8) + 2-[2-methoxy-5-methylphenyl]-1-oxido-2H-benzotriazole

Conditions	Yield
With lithium perchlorate In methanol; dichloromethane at 20℃; Cyclization; Electrolysis;	A n/a B n/a C 83%

4-Methylanisole (104-93-8) → Cresidine (120-71-8)

Conditions	Yield
With O-(4-nitrobenzoyl)hydroxylammonium trifluoromethanesulfonate; iron(II) bromide; silver(I) triflimide In 2,2,2-trifluoroethanol; water at 30℃; for 2h;	56%
With hydroxylamine triflate; iron(II) sulfate In water; acetonitrile at 20℃; for 16h;	53%
Stage #1: p-methylanizole With pyridine; tetra-n-butylammonium tetrakis(pentafluorophenyl)borate; trifluorormethanesulfonic acid In dichloromethane at 25℃; Inert atmosphere; Electrochemical reaction; Stage #2: With piperidine In acetonitrile at 80℃; for 12h; Inert atmosphere;	13%
Multi-step reaction with 2 steps 1: 1.)phenyliodine(III) bis(trifluoroacetate) (PIFA), 2.) Me3SiN3 / 1.) (CF3)2CHOH, r. t. 2: 100 percent / LAH View Scheme

2-Nitro-2'-methoxy-5'-methyl-azobenzol (29530-48-1) → 1,2-diamino-benzene (95-54-5) + 2-(2'-methoxy-5'-methylphenyl)-2H-benzotriazole (58380-86-2) + Cresidine (120-71-8)

Conditions	Yield
With sodium hydroxide; lithium perchlorate In tetrahydrofuran; water at 20℃; Cyclization; Electrolysis;	A n/a B 50% C n/a

4-methoxy-3-nitrotoluene (119-10-8) → Cresidine (120-71-8) + 2-methoxy-5-methyl-4-chloroaniline (6376-14-3)

Conditions	Yield
With hydrogenchloride; tin

4-methyl-2-nitrophenol (119-33-5) → Cresidine (120-71-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: K2CO3; xylene 2: tin; hydrochloric acid / 50 °C View Scheme

para-chlorotoluene (106-43-4) + potassium permanganate → Cresidine (120-71-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: HNO3+H2SO4 2: potassium hydroxide / 110 °C 3: ammonium sulfide; alcohol View Scheme

1-chloro-4-methyl-2-nitro-benzene (89-60-1) → Cresidine (120-71-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium hydroxide / 110 °C 2: ammonium sulfide; alcohol View Scheme

toluene (108-88-3) → Cresidine (120-71-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: iodine; iron; chlorine 2: HNO3+H2SO4 3: potassium hydroxide / 110 °C 4: ammonium sulfide; alcohol View Scheme

2-Bromoacetyl bromide (598-21-0) + Cresidine (120-71-8) → 2-bromo-N-(2-methoxy-5-methylphenyl)acetamide

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	100%

7-iodo-benzofuran-5-sulfonyl chloride (856678-58-5) + Cresidine (120-71-8) → 7-iodo-N-(2-methoxy-5-methylphenyl)-1-benzofuran-5-sulfonamide (856678-59-6)

Conditions	Yield
With pyridine In dichloromethane at 20℃;	99%

Cresidine (120-71-8) + tetramethylammonium trifluoromethanethiolate → 2-isothiocyanato-1-methoxy-4-methylbenzene

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 0.166667h;	99%

C18H17N3O10S3 (101309-08-4) + Cresidine (120-71-8) → C26H25N5O11S3 (101309-09-5)

Conditions	Yield
Stage #1: C18H17N3O10S3 With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 1.5h; Stage #2: Cresidine With sodium hydroxide In water; acetone at 0 - 25℃; pH=6;	96%

phosgene (75-44-5) + Cresidine (120-71-8) → 1,3-bis(2-methoxy-5-methylphenyl)urea (84379-37-3)

Conditions	Yield
In tetrahydrofuran; pyridine for 3h; Heating;	89%
In tetrahydrofuran	60%

bis(trichloromethyl) carbonate (32315-10-9) + methyl (S)-2,5-diaminopentanoate dihydrochloride (40216-82-8, 60080-69-5) + Cresidine (120-71-8) → C24H32N4O6

Conditions	Yield
Stage #1: bis(trichloromethyl) carbonate; Cresidine With triethylamine In tetrahydrofuran at 0 - 20℃; for 2.5h; Stage #2: methyl (S)-2,5-diaminopentanoate dihydrochloride With triethylamine In tetrahydrofuran at 65℃; for 12h;	89%

2,4-dioctyloxy-5-nitrobenzoyl chloride (271261-75-7) + Cresidine (120-71-8) → 3-(2,4-dioctyloxy-5-nitrobenzoylamino)-4-methoxytoluene (271261-76-8)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃; Substitution;	88.7%

diisopropyl (chloroethynyl)phosphonate (41459-62-5) + Cresidine (120-71-8) → [N,N'-bis-(2-methoxy-5-methylphenyl)carbamimidoylmethyl]phosphonic acid diisopropyl ester

Conditions	Yield
With potassium carbonate In acetonitrile for 14h; Reflux;	88%

3,5-di-tert-butyl-2-hydroxybenzaldehyde (37942-07-7) + Cresidine (120-71-8) → C23H31NO2

Conditions	Yield
With formic acid In methanol for 10h; Inert atmosphere; Reflux;	88%

2-(4'-aminophenyl)-4-quinolinecarboxylic acid (94205-62-6) + Cresidine (120-71-8) → 4-(4-hydroxycarbonyl-2-quinolyl)-4'-amino-2'-methyl-5'-methoxyazobenzene

Conditions	Yield
Stage #1: 2-(4'-aminophenyl)-4-quinolinecarboxylic acid With hydrogenchloride; sodium nitrite at 2℃; for 0.5h; Stage #2: Cresidine With hydrogenchloride; sodium acetate at 10 - 20℃; for 16h; pH=4.5;	87%

Cresidine (120-71-8) + 2-(4'-aminophenyl)-6-bromo-4-quinolinecarboxylic acid (475474-43-2) → 4-(4-hydroxycarbonyl-6-bromo-2-quinolyl)-4'-amino-2'-methyl-5'-methoxyazobenzene

Conditions	Yield
Stage #1: 2-(4'-aminophenyl)-6-bromo-4-quinolinecarboxylic acid With hydrogenchloride; sodium nitrite at 2℃; for 0.5h; Stage #2: Cresidine With hydrogenchloride; sodium acetate at 10 - 20℃; pH=4.5;	87%

Cresidine (120-71-8) → 4-bromo-2-methoxy-5-methylaniline (873980-68-8)

Conditions	Yield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 20℃; for 18h;	86%
With bromine In dichloromethane at 0 - 23℃; for 16h;	51%
With bromine In dichloromethane at 0 - 20℃;	50%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 16h;

cyclohexanone (108-94-1) + 3-phenyl-2,2-dihydroxy-3-oxopropionic acid ethyl ester (134390-45-7) + Cresidine (120-71-8) → ethyl 1-(2-methoxy-5-methylphenyl)-2-phenyl-4,5-dihydro-1H-indole-3-carboxylate

Conditions	Yield
With benzoic acid In toluene at 65℃; for 36h;	85%

5-chlorothiophene-2-carbonyl chloride (42518-98-9) + Cresidine (120-71-8) → C13H12ClNO2S

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 8h; Cooling with ice;	85%

1,8-dihydroxy-4,5-dinitro-anthraquinone (81-55-0) + Cresidine (120-71-8) → 1,8-dihydroxy-4-((2-methoxy-5-methylphenyl)amino)-5-nitroanthracene-9,10-dione

Conditions	Yield
In 2-methoxy-ethanol for 6h; Heating;	85%

Cresidine (120-71-8) → 2-iodo-4-methylanisole (50597-88-1)

Conditions	Yield
With toluene-4-sulfonic acid; sodium iodide In water; acetonitrile at 10 - 25℃; for 2h;	82%
With toluene-4-sulfonic acid; sodium iodide In water; acetonitrile at 10 - 20℃; for 2h; Inert atmosphere;	82%
With sulfuric acid Diazotization.Behandlung der Diazoniumsalz-Loesung mit KI, zuletzt auf dem Dampfbad;
With hydrogenchloride; potassium iodide; sodium nitrite Multistep reaction;

4-chloro-2-(2-pyrazinyl)-6-(trifluoromethyl)pyrimidine (438249-85-5) + Cresidine (120-71-8) → 4-(2-Methoxy-5-methylanilino)-2-(2-pyrazinyl)-6-trifluoromethylpyrimidine (438249-23-1)

Conditions	Yield
	81%

4-dodecyloxy-2-methoxy-5-nitro-benzoyl chloride (874210-52-3) + Cresidine (120-71-8) → 4-dodecyloxy-2-methoxy-N-(2-methoxy-5-methyl-phenyl)-5-nitro-benzamide (874210-63-6)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 18h;	77.1%

Upstream product

• 1313-82-2 Sodium sulfide 
• 106-43-4 4-Chlorotoluene 
• 104-93-8 4-Methylanisole 
• 89-60-1 4-Chloro-3-nitrotoluene 
• 772-54-3 N-BENZYLDIETHYLAMINE 
• 77-78-1 Dimethyl sulfate 
• 89-59-8 4-Chloro-2-nitrotoluene 

Downstream Products

• 2945-96-2 Direct Grey D 
• 82944-42-1 tetrasodium 3,3'-[(1,6-dihydro-6-oxo-1,3,5-triazine-2,4-diyl)bis[imino(5-methoxy-2-methyl-4,1-phenylene)azo]]bis(naphthalene-1,5-disulphonate) 
• 1937-34-4 tetrasodium 4,4'-[carbonylbis[imino(5-methoxy-2-methyl-4,1-phenylene)azo]]bis[5-hydroxynaphthalene-2,7-disulphonate] 
• 6471-78-9 4-Amino-5-methoxy-2-methylbenzensulfonic acid 
• 3354-97-0 trisodium 4-hydroxy-5-[[4-[[1-hydroxy-6-(phenylamino)-3-sulphonato-2-naphthyl]azo]-5-methoxy-2-methylphenyl]azo]naphthalene-2,7-disulphonate 
• 5489-77-0 DIRECT VIOLET 51 
• 61951-85-7 Reactive Yellow 84 
• 6227-14-1 Direct Violet 9 
• 6388-26-7 Direct Green 26 

Recommend Products

• 854225-15-3  2-(2-methoxy-5-methyl-anilino)-ethanol 
• 75-21-8  oxirane 
• 56843-30-2  acetic acid-(2-methoxy-5-methyl-4-nitro-anilide) 
• 108-24-7  acetic anhydride 
• 85968-72-5  acetoacetic acid-(2-methoxy-5-methyl-anilide) 
• 141-97-9  ethyl acetoacetate 
• 6962-44-3  N-(2-methoxy-5-methylphenyl)acetamide 
• 64-19-7  acetic acid 
• 79-22-1  methyl chloroformate 
• 39522-26-4  6-methyl-4H-benzo[1,4]oxazin-3-one 
• 79-04-9  chloroacetyl chloride 
• 85817-61-4  2-chloro-N-(2-methoxy-5-methylphenyl)acetamide 
• 116-41-6  N-(2-methoxy-5-methylphenyl)-4-methylbenzenesulfonamide 
• 98-59-9  p-toluenesulfonyl chloride