| Identification | More | [Name]
p-Toluidine | [CAS]
106-49-0 | [Synonyms]
4-AMINO-1-METHYLBENZENE
4-AMINOTOLUENE
4-METHYLANILINE
4-TOLUIDINE
AKOS BBS-00003676
LABOTEST-BB LTBB000471
P-AMINOTOLUENE
PARA-TOLUIDINE
P-METHYLANILINE
P-TOLUIDINE
P-TOLYLAMINE
1-Amino-4-methylbenzene
4-Aminotoluen
4-aminotoluen(czech)
4-methyl-benzenamin
4-Methylbenzenamine
4-methyl-Benzenamine
Aniline, p-methyl-
aniline,4-methyl-
Benzenamine, 4-methyl- | [EINECS(EC#)]
203-403-1 | [Molecular Formula]
C7H9N | [MDL Number]
MFCD00007906 | [Molecular Weight]
107.15 | [MOL File]
106-49-0.mol |
| Chemical Properties | Back Directory | [Appearance]
White lustrous plates or leaflets. Soluble in alcohol and ether; very slightly soluble
in water. Combustible. | [Melting point ]
41-46 °C(lit.) | [Boiling point ]
200 °C(lit.) | [density ]
0.973 g/mL at 25 °C(lit.)
| [vapor density ]
3.9 (vs air)
| [vapor pressure ]
0.26 mm Hg ( 25 °C)
| [refractive index ]
1.5636 | [Fp ]
192 °F
| [storage temp. ]
2-8°C
| [solubility ]
Soluble in ethanol, pyridine, diethyl ether, acetone, carbon tetrachloride, methanol, carbon disulfide, oils and dilute acids. | [form ]
powder
| [pka]
5.08(at 25℃) | [color ]
tan to brown
| [Specific Gravity]
0.962 | [Stability:]
Stable. Incompatible with strong oxidizing agents, strong acids. | [explosive limit]
6.6% | [Water Solubility ]
1.1 g/100 mL | [Sensitive ]
Air & Light Sensitive | [Detection Methods]
GC,NMR | [Merck ]
14,9536 | [BRN ]
471281 | [Dielectric constant]
4.9800000000000004 | [Exposure limits]
TLV-TWA skin 2 ppm (～9 mg/m3) (ACGIH);
Suspected Human Carcinogen (ACGIH). | [LogP]
1.39-1.44 at pH7.4-7.5 | [CAS DataBase Reference]
106-49-0(CAS DataBase Reference) | [NIST Chemistry Reference]
p-Toluidine(106-49-0) | [EPA Substance Registry System]
106-49-0(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T,N | [Risk Statements ]
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R36:Irritating to the eyes.
R40:Limited evidence of a carcinogenic effect.
R43:May cause sensitization by skin contact.
R50:Very Toxic to aquatic organisms. | [Safety Statements ]
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S36/37:Wear suitable protective clothing and gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S61:Avoid release to the environment. Refer to special instructions safety data sheet . | [RIDADR ]
UN 3451 6.1/PG 2
| [WGK Germany ]
2
| [RTECS ]
XU3150000
| [F ]
8-23 | [Autoignition Temperature]
899 °F | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
II | [HS Code ]
38220000 | [Safety Profile]
Confirmed carcinogen.
Poison by ingestion and intraperitoneal
routes. Mutation data reported. A severe
skin and eye irritant. Flammable when
exposed to heat, flame, or oxidizers. Can
react vigorously on contact with oxidzing
materials. To fight fire, use foam, CO2, dry
chemical. When heated to decomposition it
emits highly toxic fumes of NOx. See also o-
TOLUIDINE and ANILINE. | [Hazardous Substances Data]
106-49-0(Hazardous Substances Data) | [Toxicity]
LD50 orally in Rabbit: 336 mg/kg LD50 dermal Rabbit 890 mg/kg |
| Hazard Information | Back Directory | [General Description]
Colorless solid. Melting point 44°C (111°F). Specific gravity 1.046. Vapor heavier than air. Produces toxic oxides of nitrogen during combustion. May be absorbed through the skin. Used in dyes, and in organic chemical manufacturing. | [Reactivity Profile]
P-TOLUIDINE(106-49-0) neutralizes acids to form salts plus water in exothermic reactions. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated in combination with strong reducing agents, such as hydrides. Can react vigorously with oxidizing reagents. Emits very toxic fumes of oxides of nitrogen when heated to decomposition. Hypergolic reaction with red fuming nitric acid [Kit and Evered, 1960, p. 239, 242]. | [Air & Water Reactions]
Very slightly soluble in water. | [Health Hazard]
Absorption of toxic quantities by any route causes cyanosis (blue discoloration of lips, nails, skin); nausea, vomiting, and coma may follow. Repeated inhalation of low concentrations may cause pallor, low-grade secondary anemia, fatigability, and loss of appetite. Contact with eyes causes irritation. | [Potential Exposure]
para-Toluidine is used in dyes, and in organic chemical manufacturing | [Fire Hazard]
Special Hazards of Combustion Products: Toxic and flammable vapors may form in fire. | [First aid]
Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim warm and quiet. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Medical observation is recommended for 24-48 hours after breathing overexposure, as pulmonary edema may be delayed. As first aid for pulmonary edema, a doctor or authorized paramedic may consider administering a drug or other inhalation therapy. | [Shipping]
UN3451 Toluidines, solid, Hazard Class: 6.1; Labels: 6.1-Poisonous materials | [Incompatibilities]
para-Toluidine is 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. p-Toluidine neutralizes acids to form salts plus water in exothermic reactions. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated in combination with strong reducing agents, such as hydrides. Hypergolic reaction with red fuming nitric acid | [Chemical Properties]
p-Toluidine is a colorless solid. | [Chemical Properties]
White lustrous plates or leaflets. Soluble in alcohol and ether; very slightly soluble
in water. Combustible. | [Waste Disposal]
Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal. Controlled incineration (oxides of nitrogen are removed from the effluent gas by scrubbers and/or thermal devices). | [Uses]
Manufacture of various dyes and other organic chemicals. o-Isomer also in printing textiles blue black; making colors fast to acids. p-Isomer also as a reagent for lignin, nitrite, phloroglucinol. | [Uses]
p-Toluidine is an intermediate in the production of dyes, organic chemicals and aromatic azo compounds. It serves as a component of accelerators for cyanoacrylate glues. Furthermore, it acts as a bidentate Schiff base ligand through condensation with salicylaldehyde. It reacts with catecholamine to form a dye which is useful for spectrophotometric determination of catecholamine drugs. | [Uses]
p-Toluidine is used as an intermediate in themanufacture of various dyes. It is also usedas a reagent for lignin and nitrites. | [Definition]
ChEBI: An aminotoluene in which the amino substituent is para to the methyl group. | [Synthesis Reference(s)]
Tetrahedron Letters, 32, p. 2759, 1991 DOI: 10.1016/0040-4039(91)85078-J
Journal of the American Chemical Society, 89, p. 5311, 1967 DOI: 10.1021/ja00996a055 | [Carcinogenicity]
In an 18-month p-toluidine hydrochloride diet carcinogenicity
study, maleCDrats (1000 and 2000 ppmfor 18 months)
did not develop statistically significant increases of tumors;
however,CD-1male and female mice (1000 ppmfor 6 months
and then 500 ppmfor additional 12 months; or 2000 ppm for 6
months and then 1000 ppm for additional 12 months) showed
significant increases in liver carcinomas: in males at both dose
levels and in females at the high dose level. | [Purification Methods]
In general, methods similar to those for purifying aniline can be used. It can be separated from the o-and m-isomers by fractional crystallisation from its melt. p-Toluidine has been crystallised from hot water (charcoal), EtOH, *benzene, pet ether or EtOH/water (1:4), and dried in a vacuum desiccator. It can also be sublimed at 30o under vacuum. For further purification, use has been made of the oxalate, the sulfate and acetylation. The oxalate, formed as described for o-toluidine, is filtered, washed and recrystallised three times from hot distilled water. The base is regenerated with aqueous Na2CO3 and recrystallised three times from distilled water. [Berliner & May J Am Chem Soc 49 1007 1927.] Alternatively, p-toluidine is converted to its acetyl derivative which, after repeated crystallisation from EtOH, is hydrolysed by refluxing (50g) in a mixture of 500mL of water and 115mL of conc H2SO4 until a clear solution is obtained. The amine sulfate is isolated, suspended in water, and NaOH is added. The free base is distilled twice from zinc dust under vacuum. The p-toluidine is then recrystallised from pet ether and dried in a vacuum desiccator or in a vacuum for 6hours at 40o. The benzoyl derivative has m 158o (from EtOH). [Berliner & Berliner J Am Chem Soc 76 6179 1954, Moore et al. J Am Chem Soc 108 2257 1986, Beilstein 12 H 880, 12 I 140, 12 II 482, 12 III 2017, 12 IV 1866.] |
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