4-aminobenzenesulfonamide
Sulfanilamide
CAS: 63-74-1
Molecular Formula: C6H8N2O2S
4-aminobenzenesulfonamide - Names and Identifiers
4-aminobenzenesulfonamide - Physico-chemical Properties
| Molecular Formula | C6H8N2O2S |
| Molar Mass | 172.2 |
| Density | 1.08 |
| Melting Point | 164-166°C(lit.) |
| Boling Point | 400.5±47.0 °C(Predicted) |
| Water Solubility | 7.5 g/L at 25 ºC |
| Solubility | Soluble in acetone, glycerin, hydrochloric acid, boiling water and caustic solution, slightly soluble in water, almost insoluble in chloroform, ether, petroleum ether and benzene. |
| Vapor Presure | 0.00001 hPa (70 °C) |
| Appearance | White particles or powdered crystals |
| Color | white to faintly beige |
| Odor | Odorless |
| Maximum wavelength(λmax) | 257nm(H2O)(lit.) |
| Merck | 14,8925 |
| BRN | 511852 |
| pKa | pKa 10.65(H2Ot = 25.0±0.5I = 0.2) (Uncertain) |
| PH | 5.8-6.1 (5g/l, H2O, 20℃) |
| Storage Condition | 2-8°C |
| Sensitive | Easily absorbing moisture |
| Refractive Index | 1.6490 (estimate) |
| MDL | MFCD00007939 |
| Physical and Chemical Properties | Characteristics of white particles or powder Crystal, odorless. The taste was slightly bitter. Melting Point: 165~166 ℃ relative density: 1.08g/cm3 solubility: slightly soluble in cold water, ethanol, methanol, ether and acetone, soluble in boiling water, glycerin, hydrochloric acid, potassium hydroxide and sodium hydroxide solution, insoluble in chloroform, ether, benzene, petroleum ether. |
| Use | Used in the pharmaceutical industry, is the main raw material for the synthesis of sulfonamides |
4-aminobenzenesulfonamide - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 40 - Limited evidence of a carcinogenic effect |
| Safety Description | S24/25 - Avoid contact with skin and eyes. S36 - Wear suitable protective clothing. S22 - Do not breathe dust. |
| WGK Germany | 3 |
| RTECS | WO8400000 |
| FLUKA BRAND F CODES | 10 |
| TSCA | Yes |
| HS Code | 29350090 |
| Hazard Class | 8 |
| Toxicity | LD50 orally in mice: 3.8 g/kg (Marshall) |
4-aminobenzenesulfonamide - Upstream Downstream Industry
4-aminobenzenesulfonamide - Reference
| Reference Show more | 1. Kollinger, Kefei, niudejun, et al. Screening of sulfonamide sensitive strains by UV mutagenesis and its application in the detection of milk sulfonamide antibiotics [J]. Modern food science and technology, 2019, 35(5):296-303. 2. [IF = 9.229] Yi Jia et al."Effective Nitrate-to-Ammonia Electroreduction. Acs Appl Mater Inter. 2021;13(38):45521-45527 |
4-aminobenzenesulfonamide - Nature
Open Data Verified Data
white particles or powder crystals, odorless. The taste was slightly bitter. Slightly soluble in cold water, ethanol, methanol, ether and acetone, soluble in boiling water, glycerol, hydrochloric acid, potassium hydroxide and sodium hydroxide solution, insoluble in chloroform, ether, benzene, petroleum ether. Density 1. 08g/cm3, melting point
165~166 deg C.
Last Update：2024-01-02 23:10:35
4-aminobenzenesulfonamide - Introduction
No smell. The taste is slightly sweet after being bitter at the beginning, and it gradually becomes deeper when encountering sunlight. A neutral reaction to litmus. The pH of 0-5% aqueous solution is 5-8-6-1. The maximum absorption wavelength is 257 and 313nm. Half lethal dose (dog, oral) 2000mg/kg. It's irritating.
Last Update：2022-10-16 17:27:30
4-aminobenzenesulfonamide - Safety
Open Data Verified Data
- can be used as a drug to inhibit the growth and reproduction of bacteria. Taking a large number of sulfonamides, can be due to absorption and excretion of loss of balance and death. Dog oral LD502000mg/kg. A large number of sulfanilamide can cause loss of appetite, Nausea, Vomit, Diarrhea and other side effects, the impact on the liver, kidney, can also cause tinnitus, dizziness, Head Pain, and even a variety of mental symptoms, until death. The operator should wear protective gear.
- The bag is lined with plastic bag, or the bag is lined with plastic bag, and the middle layer is packed with kraft paper bag and coat fiber bag. Generally 40kg per bag. Store in a cool, ventilated, dry place, heat, sun, moisture. According to the general provisions of the storage and transportation of chemicals.
Last Update：2022-01-01 10:55:47
4-aminobenzenesulfonamide - Nature
| storage conditions | 2-8°C |
| solubility | 5.37g/l |
| acidity coefficient (pKa) | pKa 10.65(H2O t = 25.0±0.5 I = 0.2) (Uncertain) |
| morphology | powder |
| color | white to faintly beige |
| Odor | Odorless |
| PH value | 5.8-6.1 (5g/l, H2O, 20℃) |
| pH range of acid-base indicator discoloration | 5.8 - 6.1 (0.5% aq.sol.) |
| water solubility | 7.5 g/L at 25 °C |
| maximum wavelength (& lambda;max) | 257nm(H2O)(lit.) |
| Merck | 14,8925 |
| BRN | 511852 |
| InChIKey | FDDDEECHVMSUSB-UHFFFAOYSA-N |
| NIST chemical information | Benzenesulfonamide, 4-amino-(63-74-1) |
| EPA chemical information | Sulfanilamide (63-74-1) |
Last Update：2024-04-09 19:04:55
4-aminobenzenesulfonamide - Uses and synthesis methods
product features
Sulfonamide is also called p-aminobenzene sulfonamide, sulfonamide, p-aniline sulfonamide, p-sulfonamide aniline. The precipitated from the ethanol aqueous solution is a white leaf-like crystal or crystalline powder, odorless, slightly bitter and then sweet, and changes color when exposed to light. Relative molecular mass 172.22. Relative density 1.08. Melting point 165~166 ℃. Insoluble in benzene, ether, chloroform, soluble in water (g/l): 2.6 at 10 ℃, 7.5 at 25 ℃, 17.0 at 40 ℃, 40.0 at 60 ℃, 477 at 100 ℃, soluble in ethanol, 1g per 37ml of ethanol, 1g per 5ml of acetone, soluble in glycerin, propylene glycol, soluble in hydrochloric acid and sodium hydroxide (potassium) solution, sulfa amine aqueous solution litmus test paper is neutral, pH of 0.5% aqueous solution = 5.8~6.1. The color becomes darker under light. A large amount of sulfanilamide in humans can cause nausea, vomiting, diarrhea, affect the liver and kidneys, and can also cause tinnitus, dizziness, headache, and even various neurological symptoms until death. The dog's oral LD50 2000mg/kg.
[pharmacodynamics] the mechanism of action is to interfere with the synthesis of nucleic acid required by pathogenic microorganisms, so that bacteria lack nutrition and stop growth, development and reproduction. It has inhibitory effect on hemolytic streptococcus, staphylococcus and meningococcus.
[Pharmacokinetics] Oral administration is easy to be absorbed from the gastrointestinal tract and is widely distributed in the body. It can penetrate the blood-brain barrier into the brain tissue and the placental barrier into the fetus. Excretion is faster, mainly metabolites are excreted from the kidneys.
[clinical application] is mainly used for traumatic infection caused by hemolytic streptococcus and staphylococcus, and local wound infection.
[use] this product is a sulfonamide drug poisoning is low, can be used for infants, pregnant women, women and menstruation, but should not be taken in large quantities. It is effective for hemolytic streptococcal infections (erysipelas, puerperal fever, tonsillitis), urinary tract infections (gonorrhea), etc.; it is also an intermediate for the synthesis of other sulfa drugs (such as sulfamidine, sulfamethazine and sulfamethoxazine, etc.).
chemical properties
white particles or powdered crystals, odorless. The taste is slightly bitter. Slightly soluble in cold water, ethanol, methanol, ether and acetone, soluble in boiling water, glycerin, hydrochloric acid, potassium hydroxide and sodium hydroxide solution, insoluble in chloroform, ether, benzene, petroleum ether.
use
1. It is used in the pharmaceutical industry and is the main raw material for the synthesis of sulfonamides
2. Used as a reagent for the determination of nitrite, also used in the pharmaceutical industry
3. Intermediates used in the synthesis of other sulfa drugs, occasionally used for wound disinfection and sterilization
4. p-aminobenzenesulfonamide is an intermediate of the herbicide sulfa and an intermediate of pharmaceutical sulfa.
5. this product is an important intermediate of sulfonamides.
6, veterinary drugs, external anti-inflammatory drugs, used for analysis and detection.
7. The antibacterial spectrum is broad, and it has antibacterial effects on Gram-positive and negative bacteria such as hemolytic streptococcus, Neisseria meningitidis, Staphylococcus. This product is topical and can be absorbed by self-wound surface. It is used for traumatic infection of hemolytic streptococcus and staphylococcus. It can also be used for rapid hemostasis of wounds.
production method
1, prepared by chlorosulfonation, amination, hydrolysis and neutralization of acetanilide. Raw material consumption quota: acetanilide (99%)1032 kg/t, chlorosulfonic acid (96%)4521 kg/t, liquid ammonia (99.8%)535 kg/t, liquid alkali (30%)863 kg/t.
2. the preparation methods are as follows.
(1) Use acetanilide as raw material
The reaction of acetanilide and chlorosulfonic acid at 40~50 ℃, then cooling, slowly adding water for acid decomposition, while precipitation, drying and filtering to obtain acetaminobenzenesulfonyl chloride, and then ammoniation, ammoniation temperature Control at 40~45 ℃, and then hydrolyze and acidify.
(2) mixed diphenylurea method
Monophenylurea and diphenylurea (called mixed urea) are condensed from aniline and urea, which are then obtained by chlorosulfonation, amination, hydrolysis, and acid analysis. The reaction process is as follows.
① condensation firstly, aniline hydrochloride and urea are condensed and reacted at a temperature of 101~110 ℃ for 3~4h to obtain mixed diphenylurea.
② chlorosulfonation Press chlorosulfonic acid into a sulfonation pot, cool and stir, when the temperature drops below 10 ℃, evenly add mixed phenylurea under stirring condition, make the reaction temperature gradually rise, finish the feeding, keep the temperature at 46~50 ℃ for 2 hours, cool to below 10 ℃, add water for acid decomposition. Control the decomposition temperature not to exceed 15 ℃, continue to stir for 20min after adding water, and then precipitate and wash with water to obtain mixed phenylurea sulfonyl chloride.
③ ammoniated 2% ammonia water is put into an ammoniating pot, cooled to 25 ℃, mixed phenylurea sulfonyl chloride is put into stirring, the temperature is controlled to 40 ℃, and the heat preservation reaction is carried out for 3 hours to obtain ammoniated liquid.
④ hydrolysis, neutralization, raise the ammonia solution to above 90 ℃, add 3% lye, continue to raise the temperature to 108~112 ℃, carry out hydrolysis for 5 hours, move into a neutralization crystallization pot, add hydrochloric acid to neutralize crystallization, cool the crystallization solution to 20 ℃, crystallize, filter, wash with water and dry to obtain the finished product.
category
Pesticides
toxicity classification
Poisoning
acute toxicity
oral-rat LD50: 3900 mg/kg; oral-mouse LD50: 3000 mg/kg
flammability hazard characteristics
Combustible in open flames, high temperatures, and strong oxidants; combustion emits nitrogen oxides and sulfur oxides to stimulate smoke
storage and transportation features
The packaging is complete, light and light; the warehouse is ventilated, away from open flames, high temperature, and stored separately from the oxidant
fire extinguishing agent
foam, carbon dioxide, dry powder, sand, 1211
Last Update：2024-04-09 01:59:49
4-aminobenzenesulfonamide - Security information
| WGK Germany | 3 |
| RTECS number | WO8400000 |
| F | 10 |
| TSCA | Yes |
| HazardClass | 8 |
| customs code | 29350090 |
| toxic substance data | 63-74-1(Hazardous Substances Data) |
| Toxicity | LD50 orally in mice: 3.8 g/kg (Marshall) |
Last Update：2024-04-09 20:49:11
4-aminobenzenesulfonamide - Reference Information
| Product characteristics | sulfonamides, also known as sulfanilamide, sulfonamide, P-aniline sulfonamide, P-sulfonamide aniline. From the ethanol solution in the precipitation of white leaf-like crystal or crystalline powder, odorless, taste first slightly bitter and then sweet, light discoloration. Relative molecular mass 172.22. The relative density was 1.08. The melting point was 165-166 °c. Insoluble in benzene, ether, chloroform, soluble in water (g/l): 10 ℃ 2.6, 25 ℃ 7.5, 40 ℃ 17.0, 60 ℃ 40.0, 100 ° C 477, also soluble in ethanol, ethanol soluble 1g per, acetone soluble 1g per 5ml, soluble in glycerol, propylene glycol, soluble in hydrochloric acid and sodium hydroxide (potassium) solution, the litmus paper of sulfanilamide aqueous solution is neutral, and the pH of 0.5% aqueous solution is 5.8~6.1. Color darkened under light. Humans take a large number of sulfonamides, can cause Nausea, Vomit, Diarrhea, the liver, kidney effects, but also cause tinnitus, vertigo, Head Pain, and even a variety of neurological symptoms, until death. Dog oral LD50 2000mg/kg. [pharmacodynamics] The mechanism of action is to interfere with the synthesis of nucleic acids required by pathogenic microorganisms, so that the bacteria lack nutrition and stop growth, development and reproduction. The hemolytic Streptococcus, Staphylococcus and meningococcus have inhibition and killing effect. [pharmacokinetics] Oral easily absorbed from the gastrointestinal tract, widely distributed in the body, can penetrate the blood-brain barrier into the brain tissue, and can penetrate the placental barrier into the fetus. Rapid excretion, mainly metabolites from the kidney. [clinical application] it is mainly used for traumatic infection caused by hemolytic Streptococcus and Staphylococcus, and local wound infection. [use] This product is a low toxicity of sulfonamides, infants, pregnant women, maternal and menstrual period can be used, but not a lot of use. It is effective for hemolytic streptococcal infection (erysipelas, puerperal fever, tonsillitis), urinary tract infection (gonorrhea), etc. It is also an intermediate for synthesizing other sulfonamides (such as sulfamidine, sulfamethazine and sulfamethoxazine).. |
| Chemical properties | white particles or powder crystals, odorless. The taste was slightly bitter. Slightly soluble in cold water, ethanol, methanol, ether and acetone, soluble in boiling water, glycerol, hydrochloric acid, potassium hydroxide and sodium hydroxide solution, insoluble in chloroform, ether, benzene, petroleum ether. |
| Use | used in the pharmaceutical industry, is the main raw material of the synthesis of sulfonamides used as a reagent for the determination of nitrite, also used in the pharmaceutical industry for the synthesis of other sulfa drug intermediates, even for wound Disinfection sterilization sulfanilamide is an intermediate of the herbicide sulfasalazine, is also an intermediate of the pharmaceutical sulfonamides. This product is an important intermediate of sulfonamides. veterinary drug, external anti-inflammatory drug, used for analysis and detection. The antibacterial spectrum is broad, and it has antibacterial effect on Gram-positive and negative bacteria such as hemolytic Streptococcus, Neisseria meningitidis and Staphylococcus. This product is a local medication, self-absorption of part of the surface. For hemolytic Streptococcus and Staphylococcus aureus and other traumatic infections. It can also be used for rapid hemostasis of wounds. |
| production method | from acetanilide by chlorosulfonation, amination, hydrolysis, neutralization. Raw material consumption quota: Acetanilide (99%)1032kg/t, chlorosulfonic acid (96%)4521kg/t, liquid ammonia (99.8%)535kg/t, liquid alkali (30%)863kg/t. There are several preparation methods. (1) with acetanilide as raw material, acetanilide and chlorosulfonic acid are reacted at 40~50 ℃, then cooled, slowly added into water for acid decomposition, and at the same time precipitation, drying and filtering to get acetaminophen benzene sulfonyl chloride, then ammoniation is carried out, and the ammoniation temperature is controlled at 40 to 45 ° C., followed by hydrolysis and acidification. (2) mixed diphenylurea method from aniline, urea condensation of monophenylurea and diphenylurea (known as mixed urea), and then chlorosulfonation, amination, hydrolysis, acid analysis obtained. The reaction process was as follows. (1) condensation aniline hydrochloride is condensed with urea and reacted at a temperature of 101-110 ° C. For 3-4H to give mixed diphenylurea. ② chlorosulfonation pressure chlorosulfonic acid into the sulfonation Pan, cooling and stirring, when the temperature dropped to below 10 ℃, mixing phenylurea is added uniformly under stirring, the reaction temperature gradually increased, the mixture was stirred at 46-50 °c for 2H, cooled to below 10 °c, and water was added for acid decomposition. The decomposition temperature was controlled not to exceed 15 ° C. After adding water, stirring was continued for 20min, followed by precipitation and washing with water to obtain mixed phenylurea sulfonyl chloride. (3) 2% ammonia water was put into an ammoniating Pan and cooled to 25 ° C., mixed phenylurea sulfonyl chloride was added under stirring, the temperature was controlled at 40 ° C., and the reaction was maintained for 3H to obtain an ammoniating solution. ④ hydrolysis and neutralization the ammoniation solution was heated to above 90 ℃, 3% alkali solution was added, and the temperature was continued to rise to 108~112 ℃, hydrolysis was carried out for 5H, transferred into neutralization crystallization pan, and hydrochloric acid was added to neutralize the crystallization, the crystallization solution was cooled to 20 ° C., crystallized, filtered, washed with water and dried to obtain a finished product. |
| category | pesticide |
| toxicity grade | poisoning |
| Acute toxicity | oral-rat LD50: 3900 mg/kg; Oral-mouse LD50: 3000 mg/kg |
| flammability hazard characteristics | flammable in open flame, high temperature, strong oxidant; combustion emissions of nitrogen oxides and sulfur oxides stimulate smoke |
| storage and transportation characteristics | The package is complete, light, light; The warehouse is ventilated, away from open flame, high temperature, separate from oxidant |
| fire extinguishing agent | foam, carbon dioxide, dry powder, sand, 1211 |
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:52:54
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View History
Raw Materials for 4-aminobenzenesulfonamide
Downstream Products for 4-aminobenzenesulfonamide
Asulam
Sulfaguanidine
4-AMINO-N-(6-CHLORO-5-METHOXY-4-PYRIMIDINYL)BENZENESULFONAMIDE
Fluorescent Brightener DCB
Sulfachloropyridazine sodium
SULFACHLOROPYRIDAZINE
AZOCASEIN
3,5-DIBROMOSULFANILAMIDE
2,6-Dibromoaniline
p-[[p-[ethyl(2-hydroxyethyl)amino]phenyl]azo]benzenesulphonamide
3,5-DICHLOROSULFANILAMIDE
p-[[4-[(2-hydroxyethyl)amino]-1-naphthyl]azo]benzenesulphonamide
Sulfaguanidine
4-AMINO-N-(6-CHLORO-5-METHOXY-4-PYRIMIDINYL)BENZENESULFONAMIDE
Fluorescent Brightener DCB
Sulfachloropyridazine sodium
SULFACHLOROPYRIDAZINE
AZOCASEIN
3,5-DIBROMOSULFANILAMIDE
2,6-Dibromoaniline
p-[[p-[ethyl(2-hydroxyethyl)amino]phenyl]azo]benzenesulphonamide
3,5-DICHLOROSULFANILAMIDE
p-[[4-[(2-hydroxyethyl)amino]-1-naphthyl]azo]benzenesulphonamide