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4-ニトロ安息香酸

4-Nitrobenzoic Acid

HCID 6108
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基本情報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
62-23-7
標準SMILES
O=C(O)c1ccc([N+](=O)[O-])cc1
InChIKey
OTLNPYWUJOZPPA-UHFFFAOYSA-N
分子式
C7H5NO4
平均分子量
167.12 g/mol
単同位体質量
167.02185764

名称と識別子

優先名称
4-Nitrobenzoic Acid
IUPAC
4-nitrobenzoic acid
現地名
4-ニトロ安息香酸
英語名
4-Nitrobenzoic acid
分子式
C7H5NO4
分子量
167.12

名称と別名

4-NITROBENZOIC ACIDp-Nitrobenzoic acid62-23-7Benzoic acid, 4-nitro-Nitrodracylic acid4-Nitrodracylic acid1-Carboxy-4-nitrobenzenep-Nitrobenzenecarboxylic acidBenzoic acid, p-nitro-p-Nitrodracylic acidDTXSID3020966para-nitrobenzoic acid
名称をさらに表示
4-ニトロ安息香酸p-ニトロ安息香酸pニトロ安息香酸P‐ニトロ安息香酸4-ニトロ安息香酸(P-)PNBA4-Nitrobenzoicp-nitrobenzoicPARA-NITROBENZOATE-Nitrobenzoic AcidPARA NITRO-BENZOIC ACID19/KG
G83NWR61OWNSC-7707DTXCID90966CHEBI:262350RefChem:100048200-526-2Kyselina p-nitrobenzoovaMFCD00007352

データベース識別子

CAS
62-23-7
PubChem CID
6108
DTXSID
DTXSID3020966
ChEMBL
CHEMBL101263
ChEBI
CHEBI:262350
UNII
G83NWR61OW
EC Number
200-526-2
Nikkaji
J2.346I、J485.889A

物性

構造計算による物性補完中

XLogP
1.9
極性表面積
83.1 Ų
水素結合供与体数
1
水素結合受容体数
4
回転可能結合数
1
重原子数
12
形式電荷
0
複雑度
190

実験および物理化学的性質

pHpH = 2.80
LogP · 2 件

log Kow = 1.89

1.89

Density · 3 件

1.55 at 90 °F (NTP, 1992) - Denser than water; will sink

1.5997

1.61 g/cm³

Color/Form · 4 件

Monoclinic leaf from water crystallization

Monoclinic leaflets, plates from benzene crystallization

Colorless crystals

Yellow-white crystals

Solubility · 6 件

less than 1 mg/mL at 79 °F (NTP, 1992)

SOL IN ALCOHOL, HOT WATER

Insoluble in cold water

One gram dissolves in 2380 mL water, 110 mL alcohol, 12 mL methanol, 150 mL chloroform, 45 mL ether, 20 mL acetone; slightly soluble in benzene, carbon disulfide; insol in petroleum ether.

In water, 200 mg/L at 25 °C

Solubility in water, g/100ml at 25 °C: 0.03 (poor)

Flash Point · 3 件

396 °F (NTP, 1992)

202 °C

201 °C c.c.

Boiling PointSublimes (NTP, 1992)
Decomposition · 2 件

When heat to decomposition it emits toxic fumes of /nitrogen oxides/.

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

This chemical does not meet GHS hazard criteria for 0.3% (1 of 386) of reports.

Warning

H302 (99.7%): Harmful if swallowed [Warning Acute toxicity, oral];H319 (81.1%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H332 (18.1%): Harmful if inhaled [Warning Acute toxicity, inhalation];H335 (16.3%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P304+P340, P305+P351+P338, P317, P319, P330, P337+P317, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 386 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 1 of 386 reports by companies.;There are 14 notifications provided by 385 of 386 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

危険有害性情報

Regulatory Information · 4 件

Chemical: Benzoic acid, 4-nitro-

Benzoic acid, 4-nitro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzoic acid, 4-nitro- 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: 17-06-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/29494;Status: Active Update: 24-01-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/13844;Status: Active Update: 21-12-2012 https://echa.europa.eu/registration-dossier/-/registered-dossier/7213

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

化学と産業

薬理情報

Metabolism/Metabolites · 3 件

THE NITRO GROUP OF P-NITROBENZOIC ACID IS REDUCED BY LIVER MICROSOMAL ENZYMES TO P-AMINOBENZOIC ACID. /FROM TABLE/

Eleven strains of Pseudomonas were isolated by selective enrichment on 4-nitrotoluene. They an utilized 4-nitrotoluene, 4-nitrobenzyl alcohol or 4-nitrobenzoate as sole sources of carbon and nitrogen. One strain, TW3, was used for more detailed studies. 4-Nitrotoluene-grown cells of TW3 take up O2 when incubated in the presence of 4-nitrobenzyl alcohol, 4-nitrobenzaldehyde and 4-nitrobenzoate. PHLC analysis of culture supernatants showed that 4-nitrobenzaldehyde and 4-nitrobenzoate were formed when 4-nitrotoluene-grown cells were incubated with 4-nitrobenzyl alcohol, whereas only 4-nitrobenzoate was found when they were incubated with 4-nitrobenzaldehyde. ... It is proposed that the pathway for 4-nitrotoluene catabolism proceeds via 4-nitrobenzyl alcohol, 4-nitrobenzaldehyde and 4-nitrobenzoate and ultimately to protocatechuate with release of the nitro group as ammonium.

The metabolism of the nitrotoluenes was compared in hepatocytes isolated from male Fischer 344 rats. ... Metabolites were separated by reverse phase HPLC and identified by coelution with standards on HPLC, specific enzyme hydrolysis and GC-MS analysis. 4-Nitrotoluene was metabolized to s-(4-nitrobenzyl) glutathione (68%), 4-nitrobenzyl alcohol (12%), sulfate and glucuronide conjugates of 4-nitrobenzyl alcohol (6%) and 4-nitrobenzoic acid (2%) (expressed as percentage of total metabolism).

Absorption, Distribution and Excretion · 2 件

POSSIBLE ABSORPTION FROM SKIN OF GUINEA PIG. /FROM TABLE/

EXCRETED PRINCIPALLY UNCHANGED, ABOUT 10-20% REDUCED TO P-AMINOBENZOIC ACID AND ACETYLATED. /FROM TABLE/

用途と製造

Uses · 5 件

Used as a reagent for alkaloids and thorium and in the production of pharmaceuticals and dyes; [HSDB] Used for organic synthesis; [Hawley]

Manufacturing intermediates. Also as a reagent for alkaloids and thorium.

Intermediate for 4-aminobenzoic acid.

Primarily in the manufacture of dyes.

Organic synthesis

関連反応

602 件
反応記録を作成
HRID 2421 の反応式
HRID 2421反応物としてuspto-grants-1998_03
HRID 2422 の反応式
HRID 2422反応物としてuspto-grants-1998_03
HRID 2423 の反応式
HRID 2423反応物としてuspto-grants-1998_03
HRID 2425 の反応式
HRID 2425反応物としてuspto-grants-1998_03
HRID 2426 の反応式
HRID 2426反応物としてuspto-grants-1998_03
HRID 2427 の反応式
HRID 2427反応物としてuspto-grants-1998_03
HRID 2428 の反応式
HRID 2428反応物としてuspto-grants-1998_03
HRID 2429 の反応式
HRID 2429反応物としてuspto-grants-1998_03
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350 °C

Melting Point · 3 件

468 °F (NTP, 1992)

Sublimes

242 °C

Vapor Pressure · 2 件

0.00000253 [mmHg]

Vapor pressure, Pa at 50 °C: 1

Heat of Combustion3881 kJ/mol
Physical Description · 4 件

P-nitrobenzoic acid appears as odorless pale yellow crystals. (NTP, 1992)

Large Crystals

Yellowish-white solid; [Hawley] Yellow crystalline powder; [MSDSonline]

WHITE-TO-YELLOW CRYSTALS.

物理化学的性質

融点
237 · 237-240 °C(lit.)
沸点
295.67 °C · 295.67°C (rough estimate)
比重(密度)
1.61 · 1.61
屈折率
1.628 · 1.6280 (estimate)
闪点
237 °C · 237 °C
貯蔵温度
30 °C · Store below +30°C.
溶解性
0.42 g/リットル · 0.42g/リットル
酸解離定数(Pka)
3.41 · 3.41(at 25℃)
外見
結晶性粉末
色
ライトイエロー
PH
3.1 · 3.1 (0.42g/l, H2O, 20℃)(saturated solution)
水溶解度
0.1 g/100 · <0.1 g/100 mL で 26 ºC
Merck
14 · 14,6589
BRN
973593 · 973593
Specific Activity
50 · 50-60 mCi/mmol
Henry's Law Constant
3.2 · 3.2×103 mol/(m3Pa) at 25℃, Abraham and Jr. (2019)
安定性
安定。可燃性。強酸化剤、シアン化物、強塩基とは相容れない。
InChI
1S/C7H5NO4/c9-7(10)5-1-3-6(4-2-5)8(11)12/h1-4H,(H,9,10)
InChIKey
OTLNPYWUJOZPPA-UHFFFAOYSA-N
SMILES
OC(=O)c1ccc(cc1)[N+]([O-])=O
LogP
1.89 · 1.890
CAS データベース
62 · 62-23-7(CAS DataBase Reference)
NISTの化学物質情報
4 · Benzoic acid, 4-nitro-(62-23-7)
EPAの化学物質情報
p-Nitrobenzoic acid (62-23-7)

化学的性質

化学的特性light yellow crystalline powder

Fire Hazards · 2 件

This chemical is combustible. (NTP, 1992)

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Risk of explosion on contact with potassium hydroxide.

Fire PotentialCombustible
Health Hazards · 1 件

SYMPTOMS: Symptoms of exposure to this compound include irritation of the skin, eyes, mucous membranes and upper respiratory tract.;ACUTE/CHRONIC HAZARDS: This compound may be harmful by inhalation, ingestion or skin absorption. It is an irritant of the skin, eyes, mucous membranes and upper respiratory tract. When heated to decomposition it emits toxic fumes of carbon monoxide, carbon dioxide and nitrogen oxides. (NTP, 1992)

Hazards Summary · 1 件

A skin, eye, mucous membrane, and upper respiratory tract irritant; [CAMEO] No significant increase in tumors in animal feeding studies; [NTP] An irritant; Effects in high-dose animal studies include convulsions, methemoglobinemia, and acute tubular necrosis; [MSDSonline]

Reactive GroupAcids, Carboxylic;Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic
Special Reports · 2 件

European Chemicals Bureau; IUCLID Dataset, 4-Nitrobenzoic Acid (CAS # 62-23-7) (2000 CD-ROM edition). Available from the Database Query page at: http://ecb.jrc.it/esis/esis.php as of December 27, 2007.

DHHS/NTP; Toxicology and Carcinogenesis Studies of p-Nitrobenzoic Acid in F344/N Rats and B6C3F1 Mice (Feed Studies) Technical Report Series # 442 (1994) NIH Pub #94-3358

Reactivity ProfileP-NITROBENZOIC ACID is incompatible with strong oxidizers. It is also incompatible with strong bases (potassium hydroxide). It may react with cyanides. (NTP, 1992)
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. 4-Nitrobenzoic acid is produced, as an intermediate or a final product, by process units covered under this subpart.

Chemical DangersReacts with bases, reducing agents and strong oxidants. Decomposes on heating and on burning. This produces toxic fumes including nitrogen oxides.
Physical DangersDust explosion possible if in powder or granular form, mixed with air. If dry, it can be charged electrostatically by swirling, pneumatic transport, pouring, etc.
Air and Water ReactionsInsoluble in water.

安全と保護具

Fire Fighting · 2 件

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)

Use foam, dry powder, carbon dioxide.

First Aid Measures · 4 件

Fresh air, rest.

Remove contaminated clothes. Rinse and then wash skin with water and soap.

Rinse with plenty of water (remove contact lenses if easily possible).

Rinse mouth. Refer for medical attention .

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.;SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.;INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.;INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

Safe StorageSeparated from strong oxidants, bases and strong reducing agents.
Exposure Control and Personal Protection1.0 [mg/m3], inhalable fraction[German Research Foundation (DFG)]
Nonfire Spill Response · 1 件

SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing 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.;STORAGE PRECAUTIONS: You should store this chemical under ambient temperatures, and keep it away from oxidizing materials. (NTP, 1992)

Disposal Methods · 1 件

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant life; and conformance with environmental and public health regulations.

Spillage DisposalPersonal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers.
Eye PreventionWear safety spectacles.
Fire PreventionNO open flames.
Inhalation RiskA nuisance-causing concentration of airborne particles can be reached quickly when dispersed, especially if powdered.
Skin PreventionProtective gloves.

毒性情報

Ecotoxicity Values · 2 件

LC50 Brachydanio rerio (Zebrafish) >500 mg/L/48-hr; static bioassay (OECD guideline 203)

LC50 Brachydanio rerio (Zebrafish) >500 mg/L/96 hr; static bioassay (OECD guideline 203)

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 250(SRC), determined from a log Kow of 1.89(2) and a regression-derived equation(3), indicates that 4-nitrobenzoic acid is expected to have moderate mobility in soil(SRC). The pKa of 4-nitrobenzoic acid is 3.44(4), indicating that this compound will exist almost entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization of 4-nitrobenzoic acid from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.8X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(6). 4-Nitrobenzoic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.5X10-6 mm Hg(SRC), determined from a fragment constant method(7). 4-Nitrobenzoic acid may biodegrade in soil(SRC) based on 62% degradation after 2 weeks in activated sludge inoculum during a Japanese MITI test(8), however, it took more than 64 days to decompose in a soil microflora inoculum with mineral salts medium(9).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 250(SRC), determined from a log Kow of 1.89(2) and a regression-derived equation(3), indicates that 4-nitrobenzoic 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 3.8X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). A pKa of 3.44(5) indicates 4-nitrobenzoic acid will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(6). According to a classification scheme(7), an estimated BCF of 3.2(SRC), from its log Kow(2) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 4-Nitrobenzoic acid is expected to biodegrade in water(SRC) based on 62% degradation after 2 weeks in activated sludge inoculum during a Japanese MITI test(9) and where it reached 52% of its BOD in river water collected from the Songhua River, China after 5 days(10).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 4-nitrobenzoic acid, which has an estimated vapor pressure of 2.5X10-6 mm Hg at 25 °C (SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 4-nitrobenzoic acid is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 27 days(SRC), calculated from its rate constant of 5.9X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 4-nitrobenzoic acid may be removed from the air by wet or dry deposition(SRC). 4-Nitrobenzoic acid, in isopropanol, was reduced at a wavelength of 316 nm to 4-aminobenzoic(4). Therefore, 4-nitrobenzoic is expected to undergo direct photolysis(SRC). The C6H4COOH radical was generated by photolysis of 4-nitrobenzoic acid using spin-trapping of photolysis products(5).

Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect
Exposure RoutesThe substance can be absorbed into the body by ingestion.
Ecotoxicity Excerpts · 1 件

/AQUATIC SPECIES/ The importance of nitroaromatic compounds as aquatic contaminants and the association of superoxide (O2-) mediated toxicity with the mammalian metabolism of a number of these compounds has led our laboratory to conduct an in vitro investigation of nitroaromatic-stimulated O2- production by freshwater fish. Utilizing cytochrome c reduction and cyanide-insensitive oxygen consumption assays for O2-, channel catfish (Ictalurus punctatus), largemouth bass (Micropterus salmoides) and rainbow trout (Salmo gairdneri) hepatic microsomes were exposed to nitrofurantoin (NF), p-nitrobenzoic acid (PNBA) and m-dinitrobenzene (MDNB). NF and PNBA were chosen for study as model nitroaromatic compounds, known to stimulate microsomal O2- generation in mammals; MDNB was chosen because it frequently contaminates aquatic systems. The results demonstrated that each of the three nitroaromatics is capable of significantly enhancing superoxide dismutase (SOD) inhibitable cytochrome c reduction and oxygen consumption, providing specific evidence of stimulated microsomal production of O2- by the fish species examined. The results also indicated chemical- and species-specific differences in stimulated O2- production. In both assay systems, enhancement by NF exceeded that produced by MDNB and, more pronouncedly, PNBA. Furthermore, although similar responses to all nitroaromatics were observed in microsomes isolated from catfish and bass, the assays employing trout microsomes demonstrated the greatest enhancement in NF and MDNB exposures. These findings suggest that the stimulation of O2- production may be an important mode of action for these common aquatic pollutants that merits further ecotoxicological assessment.

Signs and Symptoms · 4 件

Cough.

Redness.

Redness.

Nausea. Vomiting.

Ongoing Test Status · 1 件

The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=62-23-7]

Effluent Concentrations4-Nitrobenzoic acid was qualitatively found at an advance waste treatment facility in Seattle, Washington on November 5, 1976(1). 4-Nitrobenzoic acid was not detected in the wastewater of an ammunition plant in Stadtallendorf, Germany(2).
Soil Adsorption/Mobility · 1 件

The Koc of 4-nitrobenzoic acid is estimated as 250(SRC), using a log Kow of 1.89(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 4-nitrobenzoic acid is expected to have moderate mobility in soil. The pKa of 4-nitrobenzoic acid is 3.44(4), indicating that this compound will exist almost entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5).

Artificial Pollution Sources4-Nitrobenzoic acid's production and use in manufacturing intermediates and as a reagent for alkaloids and thorium(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 5 件

AEROBIC: Decomposition of nitrobenzoic acid took greater than 64 days by a soil microflora innoculum in mineral salts medium(1). After 180 minutes, little oxygen consumption by phenol adapted biological cultures occurred with 4-nitrobenzoic acid(2). The amounts of oxygen consumed after the 180 minute test time are 55 uL (endogenous), 64 uL (cells plus 100 mg/L 3-nitrobenzoic acid), and 346 uL (cells plus phenol - after 90 minutes) which results in a ratio of only 1.2 endogenous to 4-nitrobenzoic acid oxygen consumption(2). In a 2 week Japanese MITI test using 100 mg/L 4-nitrobenzoic acid and 30 mg/L sludge, 4-nitrobenzoic had a theoretical BOD of 62%(3). 4-Nitrobenzene reached 50.2% of its BOD in river water collected from Songhua River, China after 5 days. The river water samples contained about 8.0 mg/L dissolved oxygen, 800-3000/mL bacteria counts, pH 6.8-7.0, and temperatures of 15-20 °C(4).

AEROBIC: 4-Nitrobenzoic acid was deemed well degraded in the following tests: coupled units test, Zahn-Wellens test, MITI test, Sturm test, OECD Screen test with DOC removal at least 77 % in 28 days or less; but not in a closed bottle test where a theoretical BOD of 48% was obtained(1). In the AFNOR test, 4-nitrobenzoic acid gave 96 and 97 percent removal of DOC in 28 and 42 days, respectively, with no inhibition(2). The UV absorbency of the mononitrobenzoic acid compounds disappeared in 7 days when incubated with sewage effluent in the presence of oxygen, suggesting ring cleavage and possible mineralization(3). The lag time for the degradation of 16 mg/L of 4-nitrobenzoic acid was 3-5 days by wastewater and soil(4). The degradation of 4-nitrobenzoate by domestic sewage was inhibited by benzoate(5). According to the Japanese MITI test, 4-nitrobenzoic acid is considered to be readily biodegradable(6). Three moles of hydrogen are required to reduce the nitro group to an amino group in microbial transformations with the para nitro group being more readily reduced than the ortho group for nitrobenzoic acids(7).

AEROBIC: Based upon COD, 92% 4-nitrobenzoic acid was removed at a rate of 19.7 mg COD/g hour in adapted activated sludge(1). 4-Nitrobenzoic acid, as the sole source of carbon and nitrogen, gave rise to full growth of Nocardia V. at a concentration of 0.05% (w/v) after a lag of 4 days(2). The probable metabolic pathway for the breakdown of 4-nitrobenzoate in activated sludge is 4-nitrobenzoic acid to p-aminobenzoic acid to p-hydroxybenzoic acid to protocatechuic acid to beta-ketoadipic acid to succinic acid(3). 4-Nitrobenzoic acid biodegraded after a lag of 60-65 hours at a rate of 0.042-0.060 per hour which corresponds to a half-life of 140-170 hours using an electrolytic respirometer(4).

ANAEROBIC: Nitroaromatics are readily degraded to aromatic amines under anaerobic conditions by different kinds of microorganisms including intestinal microflora of some mammals(1). 4-Nitrobenzoic acid was stoichiometrically transformed to 4-aminobenzoic acid and was completely mineralized after prolonged exposure in a laboratory-scale 160 mL anaerobic sludge bed reactor(2). 4-Nitrobenzoic acid was inhibitory to biodegradation in diluted anaerobic primary digesting sludge with a lag period greater than 80 days(3). Under anaerobiosis, nitrobenzoic acids were transformed to aromatic amines, such as 4-aminobenzoic acid(4).

Sediment/Soil ConcentrationsSEDIMENT: 4-Nitrobenzoic acid was detected at 2 of 27 surface sediment sampling sites in the Havel and Spree Rivers, Germany(1).

法規制情報

Regulatory Information · 4 件

Chemical: Benzoic acid, 4-nitro-

Benzoic acid, 4-nitro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzoic acid, 4-nitro- 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: 17-06-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/29494;Status: Active Update: 24-01-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/13844;Status: Active Update: 21-12-2012 https://echa.europa.eu/registration-dossier/-/registered-dossier/7213

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

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. 4-Nitrobenzoic 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
DH5075000
毒性
LD50 orally in Rabbit: 1960 mg/kg
hs_code
29163900
risk_code
22-41-36
化審法
(3)-1505
hazard_code
Xn
safety_code
26-39-24/25
Hazard Classifications
Acute Tox. 4 OralCarc. 2Eye Irrit. 2Muta. 2Repr. 2Skin Irrit. 2
ストレージクラス
11 - Combustible Solids
有毒物質データの
62-23-7(Hazardous Substances Data)
U.S. Production · 3 件

2023: <75,000 lb;2022: <75,000 lb;2021: <75,000 lb;2020: 75,000 - <500,000 lb

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#3874]

4-Nitrobenzoic acid 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).

Consumer UsesIntermediate
Industry UsesIntermediate;Lubricating agent
Methods of Manufacturing · 3 件

4-Nitrobenzoic acid is produced commercially by the oxidation of 4-nitrotoluene with molecular oxygen. Oxidation with 15% nitric acid at 175 °C produces the acid in 88.5% yield. ... /Another/ method involves the nitration and subsequent oxidation of polystyrene. This method uses the steric hindrance of the polymer chain to improve the para to ortho ratio of the product.

Oxidation of p-nitrotoluene with hot chromic acid mixture.

By oxidizing p-nitrotoluene by potassium hexacyanoferrate(III) in alkaline solution, potassium permanganate, or potassium dichromate.

General Manufacturing Information · 3 件

Petroleum Lubricating Oil and Grease Manufacturing;Synthetic Dye and Pigment Manufacturing;All Other Basic Organic Chemical Manufacturing

Benzoic acid, 4-nitro-: ACTIVE

Has bactericidal action against Staphylococci and Streptococci.

応用分野 · 3 件

用途中間体の製造、アルカロイド及びトリウム用試薬

使用4-Nitrobenzoic Acid is used in the synthesis of anti-Trypanosoma cruzi agents in the treatment of chagas disease.

一般的な説明Odorless pale yellow crystals.

調製方法 · 2 件

p-Nitrobenzoic acid is produced commercially by the oxidation of 4-nitrotoluene with molecular oxygen. Oxidation with 15 % nitric acid at 175 ℃ produces the acid in 88.5 % yield. An interesting method involves the nitration and subsequent oxidation of polystyrene. This method uses the steric hindrance of the polymer chain to improve the para to ortho ratio of the product.

純化方法Purify it as for 3-nitrobenzoic acid above. The amide has m 201.6o (from H2O). [Beilstein 9 III 1537, 9 IV 1072.]

上流・下流製品情報

上流原料

1-(4-ニトロフェニル)-2-アミノ-1,3-プロパンジオール重クロム酸ナトリウムクロラムフェニコール4-ニトロトルエンManganese ore powder

下流製品

オキシブプロカイン塩酸塩4-ニトロベンゾニトリル6‐キノリニルメタノール4-ニトロベンゾイル クロリドN-(4-アミノベンゾイル)-L-グルタミン酸4-ニトロ安息香酸メチル4-アミノ安息香酸 メチル4-(アセチルアミノ)ベンゾフェノン2-diethylaminoethyl 4-nitrobenzoate4-アミノ安息香酸4-アミノベンズアミジン·2塩酸塩p-アミノ安息香酸2-(イソブチルアミノ)エチル4-アミノ安息香酸イソプロピル4-ニトロ安息香酸 エチルバチルアルコール4-アミノ-N-(フェニル)ベンズアミド3,4-ジアミノ安息香酸プロカイン塩酸塩N-(2-(2-DIETHYLAMINO)ETHYL)-4-NITROBENZAMIDE4-アミノベンズアミド4-アミノフタル酸4,4'-(トリアゼン-1,3-ジイル)ビス(ベンゼンカルボイミドアミド)·2(N-アセチルグリシン)プロカイン

補足説明

定義ChEBI: A nitrobenzoic acid having the nitro group at the 4-position.

PURE CULTURE: A strain of Pseudomonas fluorescens is capable of using 4-nitrobenzoic acid as a sole source of organic carbon and nitrogen for aerobic growth(1). 4-Nitrobenzoic acid was able to support the growth of Nocardia erythropolis but was inhibitory to growth of N. opaca(2). Nocardia erythropolis and N. opaca oxidize 4-nitrobenzoate to carbon dioxide and ammonia(3).