4-Methyl-2-nitroaniline
4-Methyl-2-nitroaniline
CAS: 89-62-3
Molecular Formula: C7H8N2O2
4-Methyl-2-nitroaniline - Names and Identifiers
4-Methyl-2-nitroaniline - Physico-chemical Properties
| Molecular Formula | C7H8N2O2 |
| Molar Mass | 152.15 |
| Density | 1,164 g/cm3 |
| Melting Point | 115-116 °C (lit.) |
| Boling Point | 169°C (21 mmHg) |
| Flash Point | 157°C |
| Water Solubility | Soluble in water (0.2 g/L at 20°C). |
| Solubility | 0.2g/l |
| Vapor Presure | 0.06Pa at 25℃ |
| Appearance | Fine Crystalline Powder |
| Color | Orange to orange-brown |
| BRN | 879506 |
| pKa | 0.46±0.10(Predicted) |
| Storage Condition | −20°C |
| Refractive Index | 1.6276 (estimate) |
| Physical and Chemical Properties | characteristic orange-red combustible crystals. |
| Use | Used as a dye intermediate |
4-Methyl-2-nitroaniline - Risk and Safety
| Risk Codes | R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R33 - Danger of cumulative effects R51/53 - Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. |
| Safety Description | S28 - After contact with skin, wash immediately with plenty of soap-suds. S36/37 - Wear suitable protective clothing and gloves. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. |
| UN IDs | UN 2660 6.1/PG 3 |
| WGK Germany | 3 |
| RTECS | XU8227250 |
| TSCA | Yes |
| HS Code | 29214300 |
| Hazard Note | Irritant |
| Hazard Class | 6.1 |
| Packing Group | III |
| Toxicity | LD50 intraperitoneal in mouse: > 500mg/kg |
4-Methyl-2-nitroaniline - Upstream Downstream Industry
| Raw Materials | Benzenesulfonyl chloride p-Toluidine Sulfuric acid Sodium hydroxide Nitric acid |
| Downstream Products | Toluidine Red |
4-Methyl-2-nitroaniline - Nature
Open Data Verified Data
Orange flammable crystals. The relative density was 1. 164. Melting Point 117 °c. Flash point 157.2 °c. Soluble in ethanol and concentrated sulfuric acid.
Last Update：2024-01-02 23:10:35
4-Methyl-2-nitroaniline - Preparation Method
Open Data Verified Data
p-Toluidine is acylated with p-Toluenesulfonyl chloride to protect its amino group, then nitrated with nitric acid, and the p-Toluenesulfonyl group is removed by hydrolysis with sulfuric acid and neutralized to a finished product.
Last Update：2022-01-01 10:51:45
4-Methyl-2-nitroaniline - Use
Open Data Verified Data
color base of ice dye, such as Red Group GL. For cotton fiber and viscose fiber dyeing and printing color. They are also useful as intermediates in the manufacture of organic pigments such as toluidine red and hanshahuang G.
Last Update：2022-01-01 10:51:45
4-Methyl-2-nitroaniline - Safety
Open Data Verified Data
- This product is toxic. See O-nitroaniline.
- the iron drum is packed with plastic bags. 50kg or lookkg per barrel. Store in a dry, ventilated place to avoid sun exposure and prevent heat and moisture. Hazardous materials shall be stored and transported according to regulations.
Last Update：2022-01-01 10:51:46
4-Methyl-2-nitroaniline - Reference Information
| Color index | 37110 |
| LogP | 0.568 at 23℃ |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Use | as a dye intermediate used as a color developing agent for dyeing and printing cotton and viscose fabrics, can also be used for the synthesis of organic pigments Red GL is mainly used for cotton dyeing and cotton printing, also used for viscose fiber, silk, nylon dyeing. The dye was bright red when coupled with phenol as and phenol AS-ITR. The coupling force is strong, and the coupling speed is medium. It is also used as an intermediate in the manufacture of lakes. This product is an important intermediate of azo dye, which is the color base of ice dye (Red Group GL). For cotton fiber and viscose fiber dyeing and printing color. And can be used for the production of toluidine red, toluidine purple, Hansha yellow G and other organic pigments. |
| production method | 1. P-toluidine and p-Toluenesulfonyl chloride are used as raw materials, which are obtained by condensation, nitration, hydrolysis and neutralization. The total yield of this method is about 80%. Industrial 2-nitro-p-toluidine should meet HG2-376-80. Raw material consumption quota: P-toluidine (100%)812kg/t, chlorobenzene 300kg/t, P-Toluenesulfonyl chloride (or benzenesulfonyl chloride)(100%)1300kg/t, caustic soda (100%)634kg/t, sulfuric acid (100%)2100kg/t, nitric acid (98%)552kg/t, hydrochloric acid (31%)93kg/t, soda ash (98%)580kg/t, sodium nitrite (98%)10kg/t, sodium bisulfite (industrial) 5kg/t. 2. From the methyl acetanilide by nitration, hydrolysis. Sulfuric acid with a relative density of 1.82 is cooled, P-methyl Acetanilide is added, and nitric acid with a relative density of 1.4 is added dropwise at 25-35 ℃ for about 3H, stirred for 2H, and put into ice water to precipitate crystals, filtration and washing with water gave o-nitro-p-methylacetanilide. It was added to sodium hydroxide solution at 80-90 ° C., refluxed for 3H, cooled to room temperature, filtered out the crystals, washed with ethanol to remove the oily matter, and then recrystallized with ethanol to obtain the finished product. Raw material consumption quota: P-toluidine (99%)793kg/t, P-Toluenesulfonyl chloride (97%)1300kg/t, chlorobenzene 292kg/t, soda ash 1076kg/t, nitric acid 494kg/t, sulfuric acid 3218kg/t. Method 1: using p-toluidine as raw material, after acylation with P-Toluenesulfonyl chloride (or benzenesulfonyl chloride), Nitration with concentrated nitric acid, hydrolysis with sulfuric acid, neutralization with alkali, filtration, drying and pulverization to obtain the finished product.. Method 2: with P-methyl acetanilide as raw material, the product was obtained by nitration and hydrolysis.. 198kg of 65% nitric acid and 145kg of 96% sulfuric acid were added to the nitrifying tank, and then of p-methylacetanilide was added, stirred, cooled to maintain the temperature of 28-30 ° C., and nitrated for 2H. The nitrates were then placed in 600L of water with stirring and filtered. The filter cake is put into a hydrolysis Pan and pulped with 700L of water, and then 114kg of 45% NaOH solution is added, followed by boiling hydrolysis. The mixture was cooled with stirring, filtered and the filter cake was dried at 60 °c to give about 80kg of 2-nitro-p-toluidine. Method 3: with P-toluidine as raw material, the product was obtained by phosgenation, nitration and hydrolysis.. 1500ml of water, 187.5G of p-toluidine and 177g of sodium bicarbonate were added to the reactor, and the temperature was raised to 50-55 ℃ with stirring. Phosgene was introduced to the end point when the pH value reached below 6.199.5-199.7g. In another reactor, 80ml of chlorobenzene, 6g of (I) and 1mL of a OP-10 aqueous solution (2 %), 3.85ml of dilute nitric acid (67.5%) were added dropwise with stirring, and the addition was completed in 1 hour. Temperature to 75-80 deg C, heat preservation 8H. 2ml of sodium nitrite aqueous solution was added intermittently during this period (2%), the reaction was completed, and the Chlorobenzene was distilled with water vapor. Cooling, filtration and drying gave (II) 8-8.2g. The autoclave was sealed by adding 150mL of water, 10g (II) and 0.6g of activated carbon, and the temperature was raised to 160-170 ℃ (about 0.45-0.80MPa). The reaction was maintained for 2-3H, cooled and filtered. The filter cake was dissolved with 150ml of sulfuric acid (25%) at 90-95 °c and filtered while hot to remove insolubles. Cooling, product precipitation, filtration. The filter cake was slurried with 7.5 of water, neutralized with aqueous ammonia to pH = 8.0-7.4, filtered, washed with water, and dried to give 7.9-g of a yellow powdery product. The total yield was 81%-86%. |
Last Update：2024-04-09 15:16:53
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Raw Materials for 4-Methyl-2-nitroaniline
Downstream Products for 4-Methyl-2-nitroaniline