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95-53-4

Basic Information
CAS No.: 95-53-4
Name: Benzenamine, 2-methyl-
Article Data: 557
Cas Database
Molecular Structure:
Molecular Structure of 95-53-4 (Benzenamine, 2-methyl-)
Formula: C7H9N
Molecular Weight: 107.155
Synonyms: NSC 15348;o-Aminotoluene;o-Methylaniline;o-Methylbenzenamine;o-Tolylamine;o-Toluidine(8CI);1-Amino-2-methylbenzene;2-Amino-1-methylbenzene;2-Aminotoluene;2-Methyl-1-aminobenzene;2-Methylaniline;2-Methylbenzenamine;2-Methylphenylamine;2-Tolylamine;
EINECS: 202-429-0
Density: 0.992 g/cm3
Melting Point: -23 °C
Boiling Point: 200.4 °C at 760 mmHg
Flash Point: 84 °C
Solubility: 1.5 g/100 mL (25 °C) in water
Appearance: Light beige purple liquid
Hazard Symbols: ToxicT, DangerousN, FlammableF
Risk Codes: 45-23/25-36-50-35-20/22-10-39/23/24/25-23/24/25-11
Safety: 53-45-61-36/37/39-26-36/37-16-7
Transport Information: UN 2920 8/PG 1
PSA: 26.02000
LogP: 2.15840
Synthetic route
88-72-2

1-methyl-2-nitrobenzene

95-53-4

o-toluidine

Conditions
ConditionsYield
With hydrogen; palladium In methanol at 25℃; under 2327.2 Torr; for 1.5h;100%
With hydrogen; Pd in AV-17-8-Pd In ethanol at 40℃;100%
With hydrogen; Pd in AV-17-8-Pd In ethanol at 40℃; under 760 Torr; Rate constant;100%
31656-92-5

1-azido-2-methyl-benzene

95-53-4

o-toluidine

Conditions
ConditionsYield
With aluminum oxide; sodium formate; potassium hydroxide In neat (no solvent) for 1h; Milling;100%
With hydrogen; MCM-silylamine Pd(II) In methanol at 20℃; for 1h; Reduction;94%
With zinc(II) tetrahydroborate In 1,2-dimethoxyethane for 3h; Ambient temperature;90%
611-21-2

N,2-dimethylaniline

95-53-4

o-toluidine

Conditions
ConditionsYield
With dichloro(dimethylglyoxime)(dimethylglyoximato)cobalt(III); (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; triethylamine In acetonitrile at -78℃; for 24h; Reagent/catalyst; Sealed tube; Inert atmosphere; Irradiation;100%
Multi-step reaction with 2 steps
1: hydrogen; nickel / 300 - 330 °C
2: hydrogen; reduced nickel / 200 °C
View Scheme
17512-73-1

2-methylphenylhydroxamic acid

95-53-4

o-toluidine

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 90℃; for 2h; Lossen rearrangement;99%
With potassium carbonate In dimethyl sulfoxide at 90℃; for 2h; Lossen Rearrangement;99%
Stage #1: 2-methylphenylhydroxamic acid With acetic anhydride; potassium carbonate In dimethyl sulfoxide at 50℃; for 2h; Lossen Rearrangement;
Stage #2: With hydrogenchloride In water; dimethyl sulfoxide at 0℃;
71%
Stage #1: 2-methylphenylhydroxamic acid With potassium carbonate In dimethyl sulfoxide at 90℃; for 3h; Lossen Rearrangement;
Stage #2: With hydrogenchloride In water; dimethyl sulfoxide at 20℃; for 0.0833333h;
95-46-5

2-methylphenyl bromide

95-53-4

o-toluidine

Conditions
ConditionsYield
With copper(I) oxide; ammonium hydroxide In 1-methyl-pyrrolidin-2-one at 80℃; for 20h;96%
With ammonium hydroxide In water at 20℃; for 9h; Green chemistry;92%
With ammonium hydroxide; L-2-O-methyl-chiro-inositol; copper(II) acetate monohydrate In 1-methyl-pyrrolidin-2-one at 110℃; for 12h;88%
584-90-7

2,2'-dimethylazobenzene

95-53-4

o-toluidine

Conditions
ConditionsYield
With ammonium acetate; zinc In methanol at 20℃; for 0.05h;95%
With formic acid; zinc In methanol at 20℃; for 0.1h;94%
With ammonium formate; nickel In methanol at 20℃; for 0.1h;94%
584-90-7

trans-di-o-tolyl-diazene

95-53-4

o-toluidine

Conditions
ConditionsYield
With nickel; hydrazinium monoformate In methanol for 0.1h; Heating;94%
94-69-9

2'-methylformanilide

A

67-56-1

methanol

B

95-53-4

o-toluidine

Conditions
ConditionsYield
With potassium phosphate; C29H55FeNOP2; hydrogen In tetrahydrofuran at 110℃; under 15001.5 Torr; for 3h; Catalytic behavior;A n/a
B 94%
With C24H38Cl2N3PRu; potassium tert-butylate; hydrogen In isopropyl alcohol at 110℃; under 30402 Torr; for 30h; Autoclave; Glovebox;
97-56-3

o-aminoazotoluene

A

95-53-4

o-toluidine

B

95-70-5

2-methyl-p-phenylenediamine

Conditions
ConditionsYield
With formic acid; zinc In methanol at 20℃; for 0.2h;A 93%
B 92%
With zinc; hydrazinium monoformate In methanol for 0.2h; Heating;A n/a
B 92%
With ammonium formate; magnesium In methanol at 20℃; for 0.25h;A n/a
B 90%
615-37-2

ortho-methylphenyl iodide

95-53-4

o-toluidine

Conditions
ConditionsYield
With ammonium hydroxide In water at 20℃; for 9h; Green chemistry;93%
With ammonium hydroxide; caesium carbonate In acetonitrile for 8h; Reflux; Green chemistry;90%
With lithium amide; (CyPF-t-Bu)PdCl2 In 1,2-dimethoxyethane at 80℃; for 24h;81%
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  • ORTHO TOLUIDINE

  • Casno:

    95-53-4

    ORTHO TOLUIDINE

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Specification

The o-Toluidine, with the cas registry number 95-53-4, has the IUPAC name of 2-methylaniline. This is a kind of light yellow to light amber chemical, with the product categories including Intermediates of Dyes and Pigments; Azo dye; Amines; Aromatics; Mutagenesis Research Chemicals. Besides, it is slightly soluble in water and soluble in ethanol and ethyl ether, and is incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides.

The characteristics of this chemical are as follows: (1)ACD/LogP: 1.40; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.36; (4)ACD/LogD (pH 7.4): 1.4; (5)ACD/BCF (pH 5.5): 6.23; (6)ACD/BCF (pH 7.4): 6.77; (7)ACD/KOC (pH 5.5): 125.77; (8)ACD/KOC (pH 7.4): 136.81; (9)#H bond acceptors: 1; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 26.02; (13)Index of Refraction: 1.567; (14)Molar Refractivity: 35.31 cm3; (15)Molar Volume: 107.9 cm3; (16)Polarizability: 13.99 ×10-24 cm3; (17)Surface Tension: 39.5 dyne/cm; (18)Density: 0.992 g/cm3; (19)Flash Point: 84 °C; (20)Enthalpy of Vaporization: 43.66 kJ/mol; (21)Boiling Point: 200.4 °C at 760 mmHg; (22)Vapour Pressure: 0.325 mmHg at 25°C; (23)Exact Mass: 107.073499; (24)MonoIsotopic Mass: 107.073499; (25)Topological Polar Surface Area: 26; (26)Heavy Atom Count: 8; (27)Formal Charge: 0; (28)Complexity: 70.8.

The production method of this chemical is as below: go through the catalytic hydrogenation and reduction of ortho-nitrotoluene to get this chemical. And if you use the hydrogenation catalyst of copper (Cu), the reaction temperature is 260 °C, and you could also use the nickel catalyzator.

As to its usage, it is widely applied in many ways. It could be used as the intermediate of pigment, pesticide, pharmaceutic and organic synthesis; It could be used as the analysis reagent.

When you are dealing with this chemical, you should be very careful and then take some measures to protect yourself. For one thing, it is toxic which could at low levels cause damage to health.  It will have danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed. Besides, it may cause cancer. For another thing, it is dangerous for the environment which may present an immediate or delayed danger to one or more components of the environment. This is very toxic to aquatic organisms. In addition, it is highly flammable which may catch fire in contact with air, only needing brief contact with an ignition source, and its has a very low flash point or evolve highly flammable gases in contact with water.

Due to so many dangers, you should take the following instructions to protect yourself. Wear suitable protective clothing, gloves and eye/face protection. If iin case of accident or if you feel unwell seek medical advice immediately (show the label where possible), and if in case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, avoid exposure - obtain special instructions before use. And while keeping it, keep container tightly closed, away from sources of ignition - No smoking. Lastly, remember not to release to the environment, and you could also refer to special instructions/safety data sheet.

Additionally, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: CC1=CC=CC=C1N
(2)InChI: InChI=1S/C7H9N/c1-6-4-2-3-5-7(6)8/h2-5H,8H2,1H3
(3)InChIKey: RNVCVTLRINQCPJ-UHFFFAOYSA-N 

Below are the toxicity information of this chemical:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo oral 150mg/kg (150mg/kg) BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN
U.S. Public Health Service, Public Health Bulletin. Vol. 271, Pg. 49, 1941.
frog LDLo oral 151mg/kg (151mg/kg) BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN
U.S. Public Health Service, Public Health Bulletin. Vol. 271, Pg. 49, 1941.
mammal (species unspecified) LD50 oral 1700mg/kg (1700mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 32(10), Pg. 25, 1988.
man TCLo inhalation 25mg/m3 (25mg/m3) KIDNEY, URETER, AND BLADDER: URINE VOLUME INCREASED

KIDNEY, URETER, AND BLADDER: HEMATURIA

BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 14(8), Pg. 7, 1970.
mouse LD50 intraperitoneal 150mg/kg (150mg/kg)   National Technical Information Service. Vol. AD691-490,
mouse LD50 oral 520mg/kg (520mg/kg) BLOOD: NORMOCYTIC ANEMIA

BLOOD: PIGMENTED OR NUCLEATED RED BLLOD CELLS

BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN
IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. Vol. 27, Pg. 155, 1982.
 
rabbit LD50 oral 840mg/kg (840mg/kg) BLOOD: NORMOCYTIC ANEMIA

BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN

BLOOD: PIGMENTED OR NUCLEATED RED BLLOD CELLS
IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. Vol. 27, Pg. 155, 1982.
 
rabbit LD50 skin 3250uL/kg (3.25mL/kg)   American Industrial Hygiene Association Journal. Vol. 23, Pg. 95, 1962.
 
rat LC50 inhalation 862ppm/4H (862ppm) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: TREMOR

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
National Technical Information Service. Vol. OTS0570956,
rat LD50 oral 670mg/kg (670mg/kg) BLOOD: NORMOCYTIC ANEMIA

BLOOD: PIGMENTED OR NUCLEATED RED BLLOD CELLS

BLOOD: METHEMOGLOBINEMIA-CARBOXYHEMOGLOBIN
IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. Vol. 27, Pg. 155, 1982.
 

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