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スルファニル酸

Sulfanilic acid

HCID 8479
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
121-57-3
標準SMILES
Nc1ccc(S(=O)(=O)O)cc1
InChIKey
HVBSAKJJOYLTQU-UHFFFAOYSA-N
分子式
C6H7NO3S
平均分子量
173.19 g/mol
単同位体質量
173.01466408

概要

4-aminobenzene sulfonic acid appears as white powder with faint purple tinge. Grayish-white flat crystals. Becomes anhydrous at around 212 °F. Low toxicity (used medicinally).

名称と識別子

優先名称
Sulfanilic acid
IUPAC
4-aminobenzenesulfonic acid
現地名
スルファニル酸
英語名
Sulfanilic acid
分子式
C6H7NO3S
分子量
173.19

名称と別名

SULFANILIC ACID4-Aminobenzenesulfonic acid121-57-3Sulphanilic acidp-Aminobenzenesulfonic acidAniline-4-sulfonic acidAniline-p-sulfonic acidSulfanilsaeureAniline-p-sulphonic acidp-Aminophenylsulfonic acidp-Anilinesulfonic acidKyselina sulfanilova
名称をさらに表示
スルファニル酸アニリン-p-スルホン酸4-アミノベンゼン-1-スルホン酸アニリン-4-スルホン酸p-スルホアニリン1-アミノベンゼン-4-スルホン酸p-アニリンスルホン酸4-アミノベンゼンスルホン酸p-アミノベンゼンスルホン酸p-アミノベンゼンスルホン酸(スルファニル酸)4-スルホアニリンP‐アミノベンゼンスルホン酸4-アミノベンゼンスルホン酸標準品p - アミノベンゼンスルホン酸( スルファニル酸)スルファニル酸 [生化学用]sulfanilic4-aminobenzenesulfonateSULFANILLIC ACIDP-SULFANILIC ACIDSUFANILIC ACID
p-sulfoaniline4-Sulfoaniline4-Sulfanilic acidNSC 7170CCRIS 4576CHEBI:27500HSDB 5590EINECS 204-482-5

データベース識別子

CAS
121-57-3、97675-28-0
PubChem CID
8479
DTXSID
DTXSID6024464
ChEMBL
CHEMBL1566888
ChEBI
CHEBI:27500
UNII
434Z8C2635
EC Number
204-482-5、307-598-5
Nikkaji
J2.924F

物性

構造計算による物性補完中

XLogP
-0.6
極性表面積
88.8 Ų
水素結合供与体数
2
水素結合受容体数
4
回転可能結合数
1
重原子数
11
形式電荷
0
複雑度
210

実験および物理化学的性質

Chemical ClassesNitrogen Compounds -> Aminobenzenesulfonic Acids
PesticidesEnvironmental transformation -> Pesticide transformation products (metabolite, successor)
LogP · 3 件

log Kow = -2.16

-0.9

-2.16

Density · 4 件

1.485 at 77 °F (NTP, 1992) - Denser than water; will sink

1.485 at 25 °C/4 °C

1.49 g/cm³

1.485 @25 °C

Color/FormOrthorhombic plates or monoclinic from water
Solubility · 6 件

less than 1 mg/mL at 68 °F (NTP, 1992)

Insoluble in ethanol and ether

Soluble in fuming hydrochloric acid

Slowly sol in water: about 1% at 20 °C, about 1.45% at 30 °C, about 1.94% at 40 °C

In water, 10.68 g/L at 20 °C; 14.68 g/L at 30 °C

Solubility in water: poor

Decomposition · 2 件

When heated to decomposition it emits toxic vapors of /nitrogen oxides and sulfur oxides/.

288 °C

Melting Point · 2 件

Decomposes without melting at 550 °F (NTP, 1992)

安全と法規制

安全情報は参考情報です。供給元の安全データシート(SDS)、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 6 件

Warning

H315: Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P272, P280, P302+P352, P305+P351+P338, P321, P332+P317, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

Warning

H315 (98.6%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P272, P280, P302+P352, P305+P351+P338, P321, P332+P317, P333+P317, P337+P317, P362+P364, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory Information · 5 件

Chemical: Benzenesulfonic acid, 4-amino-

Regulation (EC) No 1107/2009 (amended)

Benzenesulfonic acid, 4-amino- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenesulfonic acid, 4-amino- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 11-12-2015 https://echa.europa.eu/registration-dossier/-/registered-dossier/14240

Benzenesulphonic acid, 4-amino-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Sulfanilic acid and its sodium salt: Human health tier II assessment
DOT LabelCorrosive
Fire Hazards · 2 件

Flash point data for this chemical are not available, however it is probably combustible. (NTP, 1992)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

Health HazardsSYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes and mucous membranes.

化学と産業

薬理情報

Mechanism of Action · 1 件

Many idiosyncratic non-steroidal anti-inflammatory drugs (NSAIDs) cause GI, liver and bone marrow toxicity in some patients which results in GI bleeding/ulceration/fulminant hepatic failure/hepatitis or agranulocytosis/aplastic anemia. The toxic mechanisms proposed have been reviewed. Evidence is presented showing that idiosyncratic NSAID drugs form prooxidant radicals when metabolized by peroxidases known to be present in these tissues. Thus GSH, NADH and/or ascorbate were cooxidised by catalytic amounts of NSAIDs and hydrogen peroxide in the presence of peroxidase. During GSH and NADH cooxidation, oxygen uptake and activation occurred. Furthermore the formation of NSAID oxidation products was prevented during the cooxidation indicating that the cooxidation involved redox cycling of the first formed NSAID radical product. The order of prooxidant catalytic effectiveness of fenamate and arylacetic acid NSAIDs was mefenamic acid>tolfenamic acid>flufenamic acid, meclofenamic acid or diclofenac. Diphenylamine, a common moiety to all of these NSAIDs was a more active prooxidant for NADH and ascorbate cooxidation than these NSAIDs which suggests that oxidation of the NSAID diphenylamine moiety to a cation and/or nitroxide radical was responsible for the NSAID prooxidant activity. The order of catalytic effectiveness found for sulfonamide derivatives was sulfaphenazole>sulfisoxazole>dapsone>sulfanilic acid>procainamide>sulfamethoxazole>sulfadiazine>sulfadimethoxine whereas sulfanilamide, sulfapyridine or nimesulide had no prooxidant activity. Although indomethacin had little prooxidant activity, its major in vivo metabolite, N-deschlorobenzoyl indomethacin had significant prooxidant activity. Aminoantipyrine the major in vivo metabolite of aminopyrine or dipyrone was also more prooxidant than the parent drugs. It is hypothesized that the NSAID radicals and/or the resulting oxidative stress initiates the cytotoxic processes leading to idiosyncratic toxicity.

Metabolism/MetabolitesYIELDS P-ACETAMIDOBENZENESULFONIC ACID IN RABBIT: DANIEL, JW, TOXICOL APPL PHARMAC, 4, 572 (1962). /FROM TABLE/
Absorption, Distribution and Excretion · 2 件

4-Aminobenzene sulfonic acid can be absorbed from the gastrointestinal tract. Absorption through the lungs appears to be possible; absorption of an intratracheally-instilled solution of 4- aminobenzene sulfonic acid has been detected in the rat. Accumulation does not take place in mammals; excretion after oral administration mainly occurs within 24 hr. 4-Aminobenzene sulfonic acid is excreted either unchanged or as the N-acetyl metabolite, in the urine in rabbits, and in the urine and the feces in rats.

関連反応

116 件
反応記録を作成
HRID 21678 の反応式
HRID 21678反応物としてuspto-grants-1995_06
HRID 95939 の反応式
HRID 95939反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 126233 の反応式
HRID 126233反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 135939 の反応式
HRID 135939反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 151652 の反応式
HRID 151652反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 180566 の反応式
HRID 180566反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 194329 の反応式
HRID 194329反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 198318 の反応式
HRID 198318反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
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化合物ノート

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このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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ノートを作成反応を作成見積依頼を出す

288 °C decomposes without melting

Vapor Pressure0.0000002 [mmHg]
Food Contact SubstancesFCS -> FDA Inventory of Food Contact Substances Listed in 21 CFR
Physical Description · 4 件

4-aminobenzene sulfonic acid appears as white powder with faint purple tinge. Grayish-white flat crystals. Becomes anhydrous at around 212 °F. Low toxicity (used medicinally).

Dry Powder

Greyish-white solid; [Hawley] White to grey solid; [ICSC] Light grey fine crystals and fragments; [MSDSonline]

WHITE POWDER OR WHITE-TO-GREY CRYSTALS.

Dissociation ConstantspKa = 3.25 at 25 °C; pKa = 3.34 at 15 °C

物理化学的性質

融点
300 °C · >300 °C(lit.)
沸点
288 ℃ · 288 ℃
比重(密度)
1.485 · 1.485
蒸気圧
0 Pa · 0Pa at 25℃
屈折率
1.55 · 1.5500 (estimate)
貯蔵温度
30 °C · Store below +30°C.
溶解性
10 g/リットル · 10g/リットル
酸解離定数(Pka)
3.24 · 3.24(at 25℃)
外見
個体
色
ホワイトからオフホワイト
PH
2.5 · 2.5 (10g/l, H2O, 20℃)
水溶解度
0.1 g/100mL · 0.1g/100mL(20℃)
Merck
14 · 14,8926
BRN
908765 · 908765
Henry's Law Constant
1.1 · 1.1×107 mol/(m3Pa) at 25℃, HSDB (2015)
安定性
安定。強力な酸化剤とは相容れない。
InChI
1S/C6H7NO3S/c7-5-1-3-6(4-2-5)11(8,9)10/h1-4H,7H2,(H,8,9,10)
InChIKey
HVBSAKJJOYLTQU-UHFFFAOYSA-N
SMILES
Nc1ccc(cc1)S(O)(=O)=O
LogP
-2.3 at · -2.3 at 25℃
CAS データベース
121 · 121-57-3(CAS DataBase Reference)
NISTの化学物質情報
4 · Benzenesulfonic acid, 4-amino-(121-57-3)
EPAの化学物質情報
Sulfanilic acid (121-57-3)

化学的性質

化学的特性greyish-white crystals or powder

Hazards Summary · 1 件

An eye and mild skin irritant; May cause skin sensitization; In monohydrate form at room temperature; Becomes anhydrous near 100 deg C; [ICSC] Sensitizing in 5 of 6 guinea pig and 1 of 2 mouse skin tests; [IUCLID] Emergency medical treatment: irritants; [HSDB] May cause skin, eye, and mucous membrane irritation; [CAMEO] An irritant; [MSDSonline]

Reactive GroupAmines, Phosphines, and Pyridines
EC ClassificationSymbol: Xi; R: 36/38-43; S: (2)-24-37
Reactivity Profile4-AMINOBENZENE SULFONIC ACID is an amino acid. Reacts weakly with both acids and bases.
Atmospheric Standards · 1 件

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Sulfanilic acid is produced, as an intermediate or a final product, by process units covered under this subpart.

Chemical DangersDecomposes on heating at 288 °C, on burning and on contact with strong acids. This produces toxic fumes including nitrogen oxides and sulfur oxides. Reacts violently with strong bases.
Air and Water ReactionsInsoluble in water.

安全と保護具

Fire Fighting · 2 件

Fires involving this compound can be extinguished using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

Use water spray, powder, foam, carbon dioxide.

First Aid Measures · 4 件

Fresh air, rest.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth.

First Aid · 1 件

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Safe StorageSeparated from strong acids and strong bases.
Cleanup Methods · 1 件

SLUDGE FROM A MUNICIPAL SEWAGE TREATMENT PLANT WAS ACCLIMATED AS SEED IN A CONTINUOUS FLOW, COMPLETELY MIXED LABORATORY REACTOR. A SUBSTRATE CONTAINING A MIXTURE OF GLUCOSE, PHENOL & SULFANILIC ACID WAS FED AT DIFFERENT FOOD-TO-MICROORGANISM RATIOS. REMOVAL RATE WAS DETERMINED AS TOTAL ORGANIC C (TOC) MEASUREMENTS. ANALYSES FOR EACH SUBSTRATE IN THE INFFLUENT & EFFLUENT SAMPLES WERE MADE.

Nonfire Spill Response · 1 件

SMALL SPILLS AND LEAKAGE: If you spill this chemical, you should dampen the solid spill material with water, then transfer the dampened material to a suitable container. Use absorbent paper dampened with water to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Wash all contaminated surfaces with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Disposal Methods · 1 件

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

Spillage Disposal · 1 件

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered sealable containers. If appropriate, moisten first to prevent dusting. Wash away remainder with plenty of water.

Isolation and EvacuationExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Eye PreventionWear safety goggles or eye protection in combination with breathing protection if powder.
Fire PreventionNO open flames.
Inhalation RiskA harmful concentration of airborne particles can be reached quickly when dispersed, especially if powdered.

毒性情報

Interactions · 3 件

WHEN GIVEN ORALLY IN SUFFICIENT AMT (100-500 MG/KG IN RATS), THE CHELATOR /ETHYLENE DIAMINETETRAACETATE/ INCREASES THE RATES OF ABSORPTION OF HEPARIN.../&/ SULFANILIC ACID...ALL LIPID-INSOL SUBSTANCES WHICH ORDINARILY ARE POORLY ABSORBED FROM GI TRACT.

BILE SALTS, DISODIUM EDTA, TETRACYCLINE, OR SODIUM LAURYL SULFATE PRESENT IN THE GUT LUMEN OF THE RAT INCREASED THE TRANSFER OF SULFANILIC ACID FROM THE SMALL INTESTINE TO THE THORACIC DUCT LYMPH.

The effect of mitomycin C (MMC) pre-administration intravenously on the absorption of drugs from rat stomach has been examined by means of the in-situ loop technique. 48 hr after the MMC-treatment, the absorption of salicylic acid, aspirin and sulphanilic acid was not influenced but that of sulphanilamide was significantly increased compared with the control. At 96 hr, a differential effect of MMC on the absorption of each drug was seen: the absorption of weakly acidic drugs was significantly decreased while that of bases and strong sulphonic acid increased. The decreased absorption of salicylic acid and aspirin correlated with the reduced gastric mucosal blood flow. At 96 hr there were severe hemorrhagic lesions in the gastric mucosa. The increase in absorption of poorly absorbed drugs could be ascribed to the increased permeability of the blood-gastric epithelium barrier as was evidenced by leakage of Evans Blue.

Ecotoxicity ValuesLC50; Species: Pimephales promelas (Fathead Minnow) weight 0.3-1 g; Conditions: freshwater, static, 22 °C, pH 7.2-7.9, hardness 40-48 mg/L CaCO3, alkalinity 30-35 mg/L CaCO3, dissolved oxygen >40%; Concentration: 100400 ug/L for 96 hr
Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that sulfanilic acid is expected to have very high mobility in soil(SRC). The pKa of sulfanilic acid is 3.25 at 25 °C(3), indicating that this compound will partially exist in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of sulfanilic acid from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.9X10-13 atm-cu m/mole(SRC), using a fragment constant estimation method(2). Sulfanilic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Based on results of the majority of eight separate laboratory determinations, it can be concluded that sulfanilic acid is not readily biodegradable(5). Sulfanilic acid, present at 100 mg/L, reached 8% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(5) which also indicates the compound is not readily biodegradable(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that sulfanilic acid is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 8.9X10-13 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). According to a classification scheme(4), an estimated BCF of 3(SRC), from a log Kow of -2.16(5) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Sulfanilic acid absorbs UV light at wavelengths >290 nm(6) and may be susceptible to direct photolysis in sunlit water(SRC). Based on results of the majority of eight separate laboratory determinations, it can be concluded that sulfanilic acid is not readily biodegradable(7). Sulfanilic acid, present at 100 mg/L, reached 8% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(8) which also indicates the compound is not readily biodegradable(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), sulfanilic acid, which has an estimated vapor pressure of 1X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase sulfanilic acid may be removed from the air by wet or dry deposition(SRC). Sulfanilic acid absorbs UV light at wavelengths >290 nm(3), and therefore may be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsSkin Sensitizer - An agent that can induce an allergic reaction in the skin.
Signs and Symptoms · 2 件

Redness.

Redness. Pain.

ICSC Environmental DataThe substance is harmful to aquatic organisms.
Soil Adsorption/Mobility · 1 件

Using a structure estimation method based on molecular connectivity indices(1), the Koc of sulfanilic acid can be estimated to be 10(SRC). According to a classification scheme(2), this estimated Koc value suggests that sulfanilic acid is expected to have very high mobility in soil. The pKa of sulfanilic acid is 3.25(3), indicating that this compound will partially exist in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).

Human Toxicity Excerpts · 2 件

/HUMAN EXPOSURE STUDIES/ ... Specific and non-specific binding of 4-aminobenzene sulfonic acid to immunoglobulins (lgD) has been detected in patients sensitized to tartrazine from which 4-aminobenzene sulfonic acid can be metabolically liberated. Patients with symptoms of recurrent urticaria have not shown hypersensitivity reactions to 4-aminobenzene sulfonic acid.

/HUMAN EXPOSURE STUDIES/ PATIENTS WITH RECURRENT URTICARIA OR ANGIOEDEMA WERE PROVOKED WITH SULFANILIC ACID. NO URTICARIAL REACTION FROM SULFANILIC ACID WAS NOTED.

Artificial Pollution SourcesSulfanilic acid's production and use as an intermediate in the production of dyes, pesticides, pharmaceuticals(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 1 件

AEROBIC: In a study assessing biodegradability by manometric respirometry conducted by the Commission of European Communities, five of the eight laboratories employed in the study determined sulfanilic acid was <20% biodegradable(1). A sixth laboratory where the inoculum was adapted to sulphonic acids found sulfanilic acid to be 70% biodegradable at 10 days and 90% biodegradable at 28 days(1). A seventh laboratory found duplicates on one occasion to give no removal while a single determination yielded 12% degradation(1). The eighth laboratory reported 6, 14 and 62% biodegradation after 28 days in three(1). Based on results of the majority of eight separate laboratory determinations, it can be concluded that sulfanilic acid is not readily biodegradable(1). Sulfanilic acid, present at 100 mg/L, reached 8% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(2) which also indicates the compound is not readily biodegradable(SRC).

Environmental Bioconcentration · 1 件

An estimated BCF of 3 was calculated in fish for sulfanilic acid(SRC), using a log Kow of -2.16(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Volatilization from Water/Soil · 1 件

The Henry's Law constant for sulfanilic acid is estimated as 8.9X10-13 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that sulfanilic acid is expected to be essentially nonvolatile from water surfaces(2). Sulfanilic acid's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Sulfanilic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1X10-9 mm Hg at 25 °C(SRC), determined from a fragment constant method(1).

法規制情報

Atmospheric Standards · 1 件

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Sulfanilic acid is produced, as an intermediate or a final product, by process units covered under this subpart.

安全データ

wgk
1
tsca
TSCA listed
rtecs
WP3895500
ridadr
UN 2790 8/PG 3
毒性
LD50 orally in Rabbit: 12300 mg/kg
hs_code
2921420090
risk_code
36/38-43-34
化審法
(3)-1971
hazard_code
C,Xi
safety_code
26-36/37/39-45-37-24-36/37
自然発火温度
>400 °C
Hazard Classifications
Eye Irrit. 2Skin Irrit. 2Skin Sens. 1
ストレージクラス
11 - Combustible Solids
有毒物質データの
121-57-3(Hazardous Substances Data)
危険度評価(NFPA 704基準/消防庁データ)
人的[青]=0

WHEN SULFANILIC ACID WAS ADMINISTERED ORALLY TO RATS, 53% OF THE ADMINISTERED DOSE WAS FOUND IN THE URINE.

用途と製造

Uses · 6 件

Used to make dyes and other organic chemicals; Also used as an analytical reagent (Ehrlich's reagent and determination of nitrites) and antibacterial; [Merck Index] Used in the paper, pulp, board, and polymer industries; Used as an additive to construction materials and foodstuffs; [IUCLID]

Pulp and Paper Processing [Category: Industry]

Manufacture of various dyes and organic chemicals; as reagent in analytical chemistry (Ehrlich's reagent, determination of nitrites)

Intermediate in the production of dyes, pesticides, pharmaceuticals.

CHEM INT FOR DYES (ESP AZO DYES), EG, C.I. ACID ORANGE 24

CHEM INT FOR ANALGESICS AND OTHER ORG CHEMS

ImpuritiesImpurities: aniline, 2,4-disulfanilic acid, 2- and 3-aminobenzenesulfonic acid.
U.S. Exports · 2 件

(1979) No Data

(1981) No Data

U.S. Imports · 2 件

(1979) 1.11X10+8 GRAMS (INCLUDES SALT)

(1981) 2.55X10+8 GRAMS (INCLUDES SALT)

U.S. Production · 6 件

2023: 7,300,000 lb

(1979) MORE THAN 4.54X10+6 GRAMS (INCL SALT)

(1981) MORE THAN 4.54X10+6 GRAMS (INCL SALT)

Benzenesulfonic acid, 4-amino- is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5446]

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Benzenesulfonic acid, 4-amino-. Aggregated National Production Volume: 10 to < 50 million pounds.

Industry UsesIntermediate
Methods of Manufacturing · 4 件

By heating aniline with weak fuming sulfuric acid and pouring the reaction product into water. /Monohydrate/

Readily prepared from aniline and sulfuric acid.

REACTION OF ANILINE WITH SULFURIC ACID OR SULFUR TRIOXIDE; BAKING OF ANILINE SULFATE TO EFFECT INTRAMOLECULAR REARRANGEMENT

Equimolar amounts of aniline and sulfuric acid are reacted in a lead-lined reactor. The reaction mass is spread on trays and baked in an oven at 190 - 220 °C, the water of the reaction being removed continuously. The process is complete if a sample dissolves clearly in a dilute alkaline solution and has practically no smell of aniline. The crude product is dissolved as a sodium salt in water that has been rendered alkaline with sodium carbonate solution; traces of aniline are removed by blowing with steam. The solution is clarified by filtration and can then be processed further immediately. The baking operation can be carried out in vacuo, which facilitates the removal of the water of the reaction.

Formulations/PreparationsGrade: Technical, pure, reagent.
Use ClassificationEnvironmental transformation -> Pesticide transformation products (metabolite, successor)
General Manufacturing Information · 3 件

Pharmaceutical and Medicine Manufacturing

Benzenesulfonic acid, 4-amino-: ACTIVE

APPLICATION OF 2000 PPM OF A FRUIT THINNING PREPARATION CONTAINING SULFANILIC ACID TO FULLY BLOOMED ORANGE TREES RESULTED IN AN INCREASE IN THINNING RATE FROM 37.6% OF THE CONTROL TO 60.8%.

応用分野 · 7 件

解説p-アミノベンゼンスルホン酸:スルファニル酸ともいう.アニリンの硫酸塩を約200 ℃ に加熱すると得られる.板状晶(二水和物).100 ℃ 付近で無水和物となる.水,エタノールに微溶.解離定数K 5.93×10-4(25 ℃).医薬品(スルホンアミド剤)として使用される.染料用の中間体である.酸解離指数pKa=3.227(25℃)。水から再結晶すると1分子の結晶水が含まれるが,100℃付近で無水物となり,約288℃以上で分解する。アニリンの硫酸水素塩を約200℃に加熱することにより合成される。この反応は,スルファミン酸が生成したのち転位を経て起こるものと考えられている。このような転位はベーキング法baking processと呼ばれ,アミノスルホン酸類の一般的な製造法である。

用途染料?殺虫剤?医薬(鎮痛剤)?蛍光増白剤等の合成中間体

用途有機合成原料、染料中間体、医薬品原料。

用途窒素酸化物測定における被ジアゾ化物。

説明Sulfanilic acid (4-amino benzene sulfonic acid ) is an off-white crystalline solid which finds application in quantitative analysis of nitrate and nitrite ions. The solid acid exists as a zwitterion, and has an unusually high melting point.

使用Sulfanilic Acid (Sulfadimethoxine EP Impurity D) is a toxic metabolite of Tartrazine (T007700). Used as Ehrlich’s reagent, for detecting of nitrites. Antibacterial.

一般的な説明White powder with faint purple tinge. Grayish-white flat crystals. Becomes anhydrous at around 212°F. Low toxicity (used medicinally).

調製方法

純化方法Crystallise the acid (as dihydrate) from boiling water. Dry it at 105o for 2-3hours, then over 90% H2SO4 in a vacuum desiccator. The S-benzylisothiuronium salt has m 187o (from aqueous EtOH). [Beilstein 14 IV 2655.]

上流・下流製品情報

上流原料

アニリン硫酸水素

下流製品

アシッド オレンジ 7キシレン ファスト イエロー 2G4-[[5-メトキシ-4-[(4-メトキシフェニル)アゾ]-2-メチルフェニル]アゾ]ベンゼンスルホン酸ナトリウムDirect Red Brown RNオーラミンDirect Blending Brilliant Red D-10BLC.I.リアクティブグリーン191-アミノ-4-ナフトールC.I.リアクティブブルー194Sumilight Supra Orangl 2GLレモンイエロー23メチルオレンジ2,5-ジクロロ-4-[4-[[5-[[4-クロロ-6-[(4-スルホフェニル)アミノ]-1,3,5-トリアジン-2-イル]アミノ]-2-スルホフェニル]アゾ]-4,5-ジヒドロ-3-メチル-5-オキソ-1H-ピラゾール-1-イル]ベンゼンスルホン酸三ナトリウム4-クロロベンゼンスルホン酸水和物Fluorescent Brightener VBUダイレクトレッド80[S,(-)]-7-ヒドロキシ-3,7-ジメチルオクタナールジメチルアセタールDirect Blending Brilliant Red D-5BLピペロナールC.I.リアクティブレッド15スルファニル酸ナトリウム1-ナフチルアミンアニリン2,5ジスルホン酸N-ベンジルスルファニル酸ナトリウム3-ヒドロキシ-4-[(2-メトキシ-5-メチル-4-スルホフェニル)アゾ]-2-ナフタレンカルボン酸二ナトリウムサンセットエローFCF4-[[4-[(4-ヒドロキシ-2-メチルフェニル)アゾ]フェニル]アミノ]-3-ニトロベンゼンスルホン酸ナトリウムDirect Blend Rubine D-BLLnew red5-ベンゾイルアミノ-3-[5-[4-クロロ-6-(4-スルホフェニルアミノ)-1,3,5-トリアジン-2-イルアミノ]-2-スルホフェニルアゾ]-4-ヒドロキシナフタレン-2,7-ジスルホン酸テトラナトリウムp-アニスアルデヒドDirect Blending Yellow D-3RNL4-クロロベンゼンスルホニルクロリド7-アニリノ-4-ヒドロキシ-3-[2-メトキシ-5-メチル-4-(4-スルホフェニルアゾ)フェニルアゾ]ナフタレン-2-スルホン酸二ナトリウムReactive Violet 2Direct Blending Scarlet D-GLN

補足説明

定義ChEBI: An aminobenzenesulfonic acid that is aniline sulfonated at the para-position.