Product Name

  • Name

    2-Methoxy-5-methylaniline

  • EINECS 204-419-1
  • CAS No. 120-71-8
  • Article Data25
  • CAS DataBase
  • Density 1.039 g/cm3
  • Solubility Slightly soluble in hot water
  • Melting Point 50-52 °C(lit.)
  • Formula C8H11NO
  • Boiling Point 235.398 °C at 760 mmHg
  • Molecular Weight 137.181
  • Flash Point 102.068 °C
  • Transport Information
  • Appearance brown to black crystalline chunks
  • Safety 53-45
  • Risk Codes 45-22
  • Molecular Structure Molecular Structure of 120-71-8 (2-Methoxy-5-methylaniline)
  • Hazard Symbols ToxicT， IrritantXi
  • Synonyms o-Anisidine,5-methyl- (7CI,8CI);1-Amino-2-methoxy-5-methylbenzene;2-Methoxy-5-methylbenzenamine;3-Amino-4-methoxytoluene;4-Methyl-2-aminoanisole;5-Methyl-2-methoxyaniline;5-Methyl-o-anisidine;Cresidine;Krezidin;NSC 406904;NSC 6162;m-Amino-p-cresol methyl ether;p-Cresidine;
  • PSA 35.25000
  • LogP 2.16700

Synthetic route

2-Methoxi-5-methylphenylazid
77721-47-2

2-Methoxi-5-methylphenylazid

Cresidine
120-71-8

Cresidine

Conditions
ConditionsYield
With lithium aluminium tetrahydride100%
With lithium aluminium tetrahydride In diethyl ether
4-methoxy-3-nitrotoluene
119-10-8

4-methoxy-3-nitrotoluene

Cresidine
120-71-8

Cresidine

Conditions
ConditionsYield
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

2-Nitro-2'-methoxy-5'-methyl-azobenzol

A

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

B

Cresidine
120-71-8

Cresidine

C

2-[2-methoxy-5-methylphenyl]-1-oxido-2H-benzotriazole

2-[2-methoxy-5-methylphenyl]-1-oxido-2H-benzotriazole

Conditions
ConditionsYield
With lithium perchlorate In methanol; dichloromethane at 20℃; Cyclization; Electrolysis;A n/a
B n/a
C 83%
...Expand
4-Methylanisole
104-93-8

4-Methylanisole

Cresidine
120-71-8

Cresidine

Conditions
ConditionsYield
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

2-Nitro-2'-methoxy-5'-methyl-azobenzol

A

1,2-diamino-benzene
95-54-5

1,2-diamino-benzene

B

2-(2'-methoxy-5'-methylphenyl)-2H-benzotriazole
58380-86-2

2-(2'-methoxy-5'-methylphenyl)-2H-benzotriazole

C

Cresidine
120-71-8

Cresidine

Conditions
ConditionsYield
With sodium hydroxide; lithium perchlorate In tetrahydrofuran; water at 20℃; Cyclization; Electrolysis;A n/a
B 50%
C n/a
...Expand
4-methoxy-3-nitrotoluene
119-10-8

4-methoxy-3-nitrotoluene

A

Cresidine
120-71-8

Cresidine

B

2-methoxy-5-methyl-4-chloroaniline
6376-14-3

2-methoxy-5-methyl-4-chloroaniline

Conditions
ConditionsYield
With hydrogenchloride; tin
4-methyl-2-nitrophenol
119-33-5

4-methyl-2-nitrophenol

Cresidine
120-71-8

Cresidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: K2CO3; xylene
2: tin; hydrochloric acid / 50 °C
View Scheme
para-chlorotoluene
106-43-4

para-chlorotoluene

potassium permanganate

potassium permanganate

Cresidine
120-71-8

Cresidine

Conditions
ConditionsYield
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

1-chloro-4-methyl-2-nitro-benzene

Cresidine
120-71-8

Cresidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium hydroxide / 110 °C
2: ammonium sulfide; alcohol
View Scheme
toluene
108-88-3

toluene

Cresidine
120-71-8

Cresidine

Conditions
ConditionsYield
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

2-Bromoacetyl bromide

Cresidine
120-71-8

Cresidine

2-bromo-N-(2-methoxy-5-methylphenyl)acetamide

2-bromo-N-(2-methoxy-5-methylphenyl)acetamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃;100%
7-iodo-benzofuran-5-sulfonyl chloride
856678-58-5

7-iodo-benzofuran-5-sulfonyl chloride

Cresidine
120-71-8

Cresidine

7-iodo-N-(2-methoxy-5-methylphenyl)-1-benzofuran-5-sulfonamide
856678-59-6

7-iodo-N-(2-methoxy-5-methylphenyl)-1-benzofuran-5-sulfonamide

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃;99%
Cresidine
120-71-8

Cresidine

tetramethylammonium trifluoromethanethiolate

tetramethylammonium trifluoromethanethiolate

2-isothiocyanato-1-methoxy-4-methylbenzene

2-isothiocyanato-1-methoxy-4-methylbenzene

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 0.166667h;99%
C18H17N3O10S3
101309-08-4

C18H17N3O10S3

Cresidine
120-71-8

Cresidine

C26H25N5O11S3
101309-09-5

C26H25N5O11S3

Conditions
ConditionsYield
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

phosgene

Cresidine
120-71-8

Cresidine

1,3-bis(2-methoxy-5-methylphenyl)urea
84379-37-3

1,3-bis(2-methoxy-5-methylphenyl)urea

Conditions
ConditionsYield
In tetrahydrofuran; pyridine for 3h; Heating;89%
In tetrahydrofuran60%
bis(trichloromethyl) carbonate
32315-10-9

bis(trichloromethyl) carbonate

methyl (S)-2,5-diaminopentanoate dihydrochloride
40216-82-8, 60080-69-5

methyl (S)-2,5-diaminopentanoate dihydrochloride

Cresidine
120-71-8

Cresidine

C24H32N4O6

C24H32N4O6

Conditions
ConditionsYield
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%
...Expand
2,4-dioctyloxy-5-nitrobenzoyl chloride
271261-75-7

2,4-dioctyloxy-5-nitrobenzoyl chloride

Cresidine
120-71-8

Cresidine

3-(2,4-dioctyloxy-5-nitrobenzoylamino)-4-methoxytoluene
271261-76-8

3-(2,4-dioctyloxy-5-nitrobenzoylamino)-4-methoxytoluene

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; Substitution;88.7%
diisopropyl (chloroethynyl)phosphonate
41459-62-5

diisopropyl (chloroethynyl)phosphonate

Cresidine
120-71-8

Cresidine

[N,N'-bis-(2-methoxy-5-methylphenyl)carbamimidoylmethyl]phosphonic acid diisopropyl ester

[N,N'-bis-(2-methoxy-5-methylphenyl)carbamimidoylmethyl]phosphonic acid diisopropyl ester

Conditions
ConditionsYield
With potassium carbonate In acetonitrile for 14h; Reflux;88%
3,5-di-tert-butyl-2-hydroxybenzaldehyde
37942-07-7

3,5-di-tert-butyl-2-hydroxybenzaldehyde

Cresidine
120-71-8

Cresidine

C23H31NO2

C23H31NO2

Conditions
ConditionsYield
With formic acid In methanol for 10h; Inert atmosphere; Reflux;88%
2-(4'-aminophenyl)-4-quinolinecarboxylic acid
94205-62-6

2-(4'-aminophenyl)-4-quinolinecarboxylic acid

Cresidine
120-71-8

Cresidine

4-(4-hydroxycarbonyl-2-quinolyl)-4'-amino-2'-methyl-5'-methoxyazobenzene

4-(4-hydroxycarbonyl-2-quinolyl)-4'-amino-2'-methyl-5'-methoxyazobenzene

Conditions
ConditionsYield
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

Cresidine

2-(4'-aminophenyl)-6-bromo-4-quinolinecarboxylic acid
475474-43-2

2-(4'-aminophenyl)-6-bromo-4-quinolinecarboxylic acid

4-(4-hydroxycarbonyl-6-bromo-2-quinolyl)-4'-amino-2'-methyl-5'-methoxyazobenzene

4-(4-hydroxycarbonyl-6-bromo-2-quinolyl)-4'-amino-2'-methyl-5'-methoxyazobenzene

Conditions
ConditionsYield
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

Cresidine

4-bromo-2-methoxy-5-methylaniline
873980-68-8

4-bromo-2-methoxy-5-methylaniline

Conditions
ConditionsYield
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

cyclohexanone

3-phenyl-2,2-dihydroxy-3-oxopropionic acid ethyl ester
134390-45-7

3-phenyl-2,2-dihydroxy-3-oxopropionic acid ethyl ester

Cresidine
120-71-8

Cresidine

ethyl 1-(2-methoxy-5-methylphenyl)-2-phenyl-4,5-dihydro-1H-indole-3-carboxylate

ethyl 1-(2-methoxy-5-methylphenyl)-2-phenyl-4,5-dihydro-1H-indole-3-carboxylate

Conditions
ConditionsYield
With benzoic acid In toluene at 65℃; for 36h;85%
...Expand
5-chlorothiophene-2-carbonyl chloride
42518-98-9

5-chlorothiophene-2-carbonyl chloride

Cresidine
120-71-8

Cresidine

C13H12ClNO2S

C13H12ClNO2S

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 8h; Cooling with ice;85%
1,8-dihydroxy-4,5-dinitro-anthraquinone
81-55-0

1,8-dihydroxy-4,5-dinitro-anthraquinone

Cresidine
120-71-8

Cresidine

1,8-dihydroxy-4-((2-methoxy-5-methylphenyl)amino)-5-nitroanthracene-9,10-dione

1,8-dihydroxy-4-((2-methoxy-5-methylphenyl)amino)-5-nitroanthracene-9,10-dione

Conditions
ConditionsYield
In 2-methoxy-ethanol for 6h; Heating;85%
Cresidine
120-71-8

Cresidine

2-iodo-4-methylanisole
50597-88-1

2-iodo-4-methylanisole

Conditions
ConditionsYield
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

4-chloro-2-(2-pyrazinyl)-6-(trifluoromethyl)pyrimidine

Cresidine
120-71-8

Cresidine

4-(2-Methoxy-5-methylanilino)-2-(2-pyrazinyl)-6-trifluoromethylpyrimidine
438249-23-1

4-(2-Methoxy-5-methylanilino)-2-(2-pyrazinyl)-6-trifluoromethylpyrimidine

Conditions
ConditionsYield
81%
4-dodecyloxy-2-methoxy-5-nitro-benzoyl chloride
874210-52-3

4-dodecyloxy-2-methoxy-5-nitro-benzoyl chloride

Cresidine
120-71-8

Cresidine

4-dodecyloxy-2-methoxy-N-(2-methoxy-5-methyl-phenyl)-5-nitro-benzamide
874210-63-6

4-dodecyloxy-2-methoxy-N-(2-methoxy-5-methyl-phenyl)-5-nitro-benzamide

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

2-Methoxy-5-methylaniline Chemical Properties

5-METHYL-o-ANISIDINE(120-71-8) is the chemical compound with the formula C8H11NO.Its molar weight is 137.18g/mol.
5-METHYL-o-ANISIDINE(120-71-8) is also named 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.
Melting Point: 50-52 oC(lit.)
Boiling Point: 235 oC(lit.)
Vapor Density: 4.7 (vs air)
Flash Point >230 oF
Water Solubility: Slightly soluble in hot water.
Index of Refraction: 1.549 
Molar Refractivity: 41.99 cm3 
Molar Volume: 131.9 cm3 
Surface Tension: 37.8 dyne/cm 
Enthalpy of Vaporization: 47.22 kJ/mol 
Vapour Pressure: 0.0502 mmHg at 25 oC
The chemical structure of 5-METHYL-o-ANISIDINE(120-71-8) is
.

2-Methoxy-5-methylaniline Uses

5-METHYL-o-ANISIDINE(120-71-8) is used as dye intermediate.

2-Methoxy-5-methylaniline Toxicity Data With Reference

1.   

skn-rbt 500 mg/24H MLD

   85JCAE    Prehled Prumyslove Toxikologie; Organicke Latky Marhold, J.,Prague, Czechoslovakia.: Avicenum,1986,721.
2.   

eye-rbt 100 mg/24H MOD

   85JCAE    Prehled Prumyslove Toxikologie; Organicke Latky Marhold, J.,Prague, Czechoslovakia.: Avicenum,1986,721.
3.   

mmo-sat 62,500 ng/plate

   ENMUDM    Environmental Mutagenesis. 7 (Suppl 5)(1985),1.
4.   

mma-sat 3330 ng/plate

   ENMUDM    Environmental Mutagenesis. 7 (Suppl 5)(1985),1.
5.   

mma-esc 2 mg/plate

   ENMUDM    Environmental Mutagenesis. 7 (Suppl 5)(1985),1.
6.   

otr-rat:emb 31 µg/plate

   JJATDK    JAT, Journal of Applied Toxicology. 1 (1981),190.
7.   

orl-rat LD50:1450 mg/kg

   HURC**    Huntingdon Research Center Reports .(Brooklandville, MD.: )1972.

2-Methoxy-5-methylaniline Consensus Reports

NTP 10th Report on Carcinogens. IARC Cancer Review: Group 2B IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 56.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Human Limited Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 27 ,1982,p. 91.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 27 ,1982,p. 91.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) . NCI Carcinogenesis Bioassay (feed); Clear Evidence: mouse, rat NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-142 ,1979. . Reported in EPA TSCA Inventory. Community Right-To-Know List.

2-Methoxy-5-methylaniline 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.
Hazard Codes: T,Xi
Risk Statements: 45-22
45:  May cause cancer 
22:  Harmful if swallowed  
Safety Statements: 53-45
53:  Avoid exposure - obtain special instruction before use 
45:  In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) 
WGK Germany: 3
RTECS: BZ6720000
F: 9
F9: Keep under nitrogen.
Hazardous Substances Data: 120-71-8(Hazardous Substances Data).

2-Methoxy-5-methylaniline Standards and Recommendations

DFG MAK: Confirmed Animal Carcinogen, Suspected Human Carcinogen

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