p-Toluidine CAS 106-49-0
Introduction：Basic information about p-Toluidine CAS 106-49-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
p-Toluidine Basic information
| Product Name: | p-Toluidine |
| Synonyms: | P-TOLUIDINE;Benzenamine,4-methyl-;benzenamine,-methyl-;benzeneamine,4-methyl-;benzeneamine,-methyl-;c.i. Azoic coupling component 107;c.i.37107;c.i.azoiccouplingcomponent107 |
| CAS: | 106-49-0 |
| MF: | C7H9N |
| MW: | 107.15 |
| EINECS: | 203-403-1 |
| Product Categories: | Azo dye;API intermediates;Intermediates of Dyes and Pigments;Anilines (Building Blocks for Liquid Crystals);Building Blocks for Liquid Crystals;Functional Materials;Intermediates;Amines;Aromatics;Miscellaneous Reagents;amine;Furans;K00001 |
| Mol File: | 106-49-0.mol |
p-Toluidine Chemical Properties
| 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. | Store below +30°C. |
| solubility | Soluble in ethanol, pyridine, diethyl ether, acetone, carbon tetrachloride, methanol, carbon disulfide, oils and dilute acids. |
| pka | 5.08(at 25℃) |
| form | powder |
| color | tan to brown |
| Specific Gravity | 0.962 |
| PH | 7.8 (7g/L) |
| explosive limit | 6.6% |
| Water Solubility | 1.1 g/100 mL |
| Sensitive | Air & Light Sensitive |
| Merck | 14,9536 |
| BRN | 471281 |
| Dielectric constant | 4.9800000000000004 |
| Exposure limits | TLV-TWA skin 2 ppm (～9 mg/m3) (ACGIH);Suspected Human Carcinogen (ACGIH). |
| Stability: | Stable. Incompatible with strong oxidizing agents, strong acids. |
| InChI | 1S/C7H9N/c1-6-2-4-7(8)5-3-6/h2-5H,8H2,1H3 |
| InChIKey | RZXMPPFPUUCRFN-UHFFFAOYSA-N |
| SMILES | Cc1ccc(N)cc1 |
| 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 | p-Toluidine (106-49-0) |
Safety Information
| Hazard Codes | T,N |
| Risk Statements | 23/24/25-36-40-43-50 |
| Safety Statements | 28-36/37-45-61-28A |
| RIDADR | UN 3451 6.1/PG 2 |
| WGK Germany | 2 |
| RTECS | XU3150000 |
| F | 8-23 |
| Autoignition Temperature | 899 °F |
| TSCA | TSCA listed |
| HazardClass | 6.1 |
| PackingGroup | II |
| HS Code | 38220000 |
| Storage Class | 6.1A - Combustible acute toxic Cat. 1 and 2 very toxic hazardous materials |
| Hazard Classifications | Acute Tox. 3 Dermal Acute Tox. 3 Inhalation Acute Tox. 3 Oral Aquatic Acute 1 Aquatic Chronic 2 Carc. 2 Eye Irrit. 2 Skin Sens. 1A |
| Hazardous Substances Data | 106-49-0(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: 336 mg/kg LD50 dermal Rabbit 890 mg/kg |
| Chemical Properties | White lustrous plates or leaflets. Soluble in alcohol and ether; very slightly solublein water. Combustible. |
| Chemical Properties | p-Toluidine is a colorless solid. |
| Uses | p-Toluidine is used as an intermediate in themanufacture of various dyes. It is also usedas a reagent for lignin and nitrites. |
| 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. |
| 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 |
| 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 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]. |
| 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. |
| Health Hazard | p-Toluidine is a mild to moderate irritanton the skin. The irritant effect on rabbits’eyes was strong. The toxic properties ofp-toluidine are similar to its ortho- and meta isomers and aniline. The clinical signs of tox icity are methemoglobinemia, anemia, andcyanosis. The major metabolite in urine afteroral application in male rats was 2-amino-5-methylphenol, which was excreted alongwith 3.5% unchanged p-toluidine (ACGIH1986). Exposure to 40-ppm concentrationfor 1 hour resulted in severe poisoning inhumans. |
| Fire Hazard | Special Hazards of Combustion Products: Toxic and flammable vapors may form in fire. |
| Safety Profile | Confirmed carcinogen.Poison by ingestion and intraperitonealroutes. Mutation data reported. A severeskin and eye irritant. Flammable whenexposed to heat, flame, or oxidizers. Canreact vigorously on contact with oxidzingmaterials. To fight fire, use foam, CO2, drychemical. When heated to decomposition itemits highly toxic fumes of NOx. See also o-TOLUIDINE and ANILINE. |
| Potential Exposure | para-Toluidine is used in dyes, and in organic chemical manufacturing |
| Carcinogenicity | In an 18-month p-toluidine hydrochloride diet carcinogenicitystudy, maleCDrats (1000 and 2000 ppmfor 18 months)did not develop statistically significant increases of tumors;however,CD-1male and female mice (1000 ppmfor 6 monthsand then 500 ppmfor additional 12 months; or 2000 ppm for 6months and then 1000 ppm for additional 12 months) showedsignificant increases in liver carcinomas: in males at both doselevels and in females at the high dose level. |
| Shipping | UN3451 Toluidines, solid, Hazard Class: 6.1; Labels: 6.1-Poisonous materials |
| 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.] |
| 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 |
| Toxics Screening Level | The initial threshold screening level (ITSL) for p-Toluidine is 0.03 μg/m3 based on an annual averaging time. |
| 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). |
p-Toluidine Preparation Products And Raw materials
| Raw materials | Sodium sulfide-->4-Nitrotoluene-->Sodium sulfide nonahydrate |
| Preparation Products | 4-Chlorotoluene-->5-Methyl-2-phenyl-1,2-dihydropyrazol-3-one-->4-Bromotoluene-->4-Aminobenzotrifluoride-->Pigment Red 122-->3-Nitrotoluene-->4-Methyl-2-nitroaniline-->6-Quinolinecarbaldehyde-->6-Quinolinylmethanol-->FUCHSIN BASIC-->4-Aminotoluene-3-sulfonic acid-->p-Fluorotoluene-->2-(4-Aminophenyl)-6-methyl-1,3-benzothiazole-7-sulfonic acid-->ACID BLUE 25-->2-Nitro-p-cresol-->1-(4-METHYLPHENYL)PIPERAZINE-->1R-cis-Permethrinic acid-->Acid Green 25-->4-Fluorobenzotrifluoride-->N-(3-Hydroxyphenyl)-4-toluidine-->5-Amino-2-methylbenzenesulfonic acid-->3,5-dinitrotoluene |
