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5-나이트로-o-톨루딘

2-Methyl-5-Nitroaniline

HCID 7444
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
99-55-8
표준 SMILES
Cc1ccc([N+](=O)[O-])cc1N
InChIKey
DSBIJCMXAIKKKI-UHFFFAOYSA-N
분자식
C7H8N2O2
평균 분자량
152.15 g/mol
단동위원소 질량
152.0585775

개요

5-nitro-o-toluidine is a bright yellow powder. (NTP, 1992)

이름 및 식별자

우선 이름
2-Methyl-5-Nitroaniline
IUPAC
2-methyl-5-nitroaniline
현지명
5-나이트로-o-톨루딘
영어명
2-Methyl-5-nitroaniline
분자식
C7H8N2O2
분자량
152.15

이름 및 동의어

2-Methyl-5-nitroaniline99-55-85-NITRO-O-TOLUIDINEScarlet G Base2-Methyl-5-nitrobenzenamine4-Nitro-2-aminotolueneFast Scarlet GPNOTFast Scarlet G Base3-Nitro-6-methylanilineDevol Scarlet BFast scarlet base G
이름 더 보기
5-나이트로-o-톨루딘5-나이트로-o-톨루이딘5-나이트로-o-톨루이딘및나이트로-o-톨루이딘하이드로클로라이드2-메틸-5-니트로아닐린2-AMINO-4-NITROTOLUENEpnot[qr]CI 37105NCI-C01843
6-Methyl-3-nitroanilineDaito Scarlet Base GDiabase Scarlet G5-Nitro-2-toluidineScarlet Base NSPBenzenamine, 2-methyl-5-nitro-1-Amino-2-methyl-5-nitrobenzeneFast Red SG Base

데이터베이스 식별자

CAS
99-55-8
PubChem CID
7444
DTXSID
DTXSID4020959
ChEMBL
CHEMBL324642
ChEBI
CHEBI:66891
UNII
433MYH2DWM
EC Number
151-712-4、202-765-8
Nikkaji
J95.089K

물성

구조 계산 물성

XLogP
1.9
극성 표면적
71.8 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
3
회전 가능 결합 수
0
무거운 원자 수
11
형식 전하
0
복잡도
155

실험 및 물리화학적 성질

Chemical ClassesNitrogen Compounds -> Nitroanilines
SpringerMaterials PropertiesDiffusion
LogP · 2건

log Kow = 1.87

1.87

Density1.365 deg 15 C/deg 4 C
Color/FormYellow monoclinic prisms
Solubility · 4건

less than 1 mg/mL at 66 °F (NTP, 1992)

Soluble in acetone, benzene, ether, ethanol, chloroform

In water, 1 g/100 mL at 19 °C

13.5 [ug/mL] (The mean of the results at pH 7.4)

Decomposition · 2건

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

Decomposes exothermically when heated to 150 °C

Melting Point · 3건

219 to 225 °F (NTP, 1992)

105.5 °C

107 °C

Vapor Pressure · 2건

0.000975 [mmHg]

0.000013 [mm Hg] @20 °C

Physical Description · 3건

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 6건

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P203, P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P318, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P318, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

유해성 정보

Regulatory Information · 4건

Chemical: Benzenamine, 2-methyl-5-nitro-

Benzenamine, 2-methyl-5-nitro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenamine, 2-methyl-5-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)

REACH registered substance: 5-nitro-o-toluidine (EC: 202-765-8)

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - Benzenamine, 2-methyl-5-nitro-: Human health tier II assessment
DOT LabelPoison
Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Health HazardsSYMPTOMS: Symptoms of exposure to this chemical include methemoglobinemia and respiratory distress.
Hazards Summary · 2건

Several Japanese workers were admitted to the hospital with severe liver damage after handling repeatedly (12-20 times) 5-nitro-o-toluidine for 4-5 hours at a time. Workers had scooped the powder by hand while wearing respirators. [Gut 2002 Feb;50(2):266-70] Methemoglobinemia is a potential adverse effect after exposure to this agent. [HSDB]

화학 및 산업

약리 정보

Metabolism/Metabolites · 1건

5-Nitro-ortho-toluidine was identified as a product of the microbial transformation by Mucrosporium sp. of 2,4-dinitrotoluene, a compound common in water discharges and effluents from ammunition plants, ammunition loading facilities and sites for the destruction of stockpiled weapons ... . 5-Nitro-ortho-toluidine was identified as an intermediate in the anaerobic biotransformation of 2,4-dinitrotoluene added to a sample of municipal activated sludge ... . 5-Nitro-ortho-toluidine is formed enzymatically from 2,4-dinitrotoluene by liver and lung microsomal fractions from mice ... by liver microsomal and cytosolic fractions from rats ... and by intestinal microorganisms from rats and mice ... . 5-Nitro-ortho-toluidine and its N-acetyl derivative were identified as minor metabolites of 2,4-(14)C-dinitrotoluene when this compound was administered orally to male and female Fischer 344 rats at doses of 35, 63 or 100 mg/kg bw ... . Human intestinal microflora catalyse the reductive metabolism of 2,4-dinitrotoluene to 5-nitro-ortho-toluidine and 4-amino-2-nitrotoluene via nitroso intermediates ... .

용도 및 제조

Uses · 5건

Workers are exposed during production or handling of more than 35 commercial dyes (orange or red) of which 5-nitro-o-toluidine is the major component; [ACGIH]

4-Nitro-o-toluidine is used as a diazo component.

CHEM INT FOR PIGMENTS-EG, CI PIGMENT RED 22 & DYES-EG, AZOIC DIAZO COMPONENT.

5-Nitro-ortho-toluidine has been used as an intermediate in the synthesis of Pigment Red 17 and Pigment Red 22. It has also been used as a precursor in the synthesis of a wide assortment of azo dyes of various red, yellow, orange, violet and brown hues ... . As an azoic diazo component, 5-nitro-ortho-toluidine is used with naphthol derivatives to form azo dyes in situ on fabric and yarns. Dyeing with naphthol dyes takes place in two phases: the textile is first immersed in a solution of azoic coupling component, naphthol, and then allowed to react with an azoic diazonium component consisting of an aromatic amine converted first to a diazonium derivative ... .

Substance listed with specific concentration in tattoo ink and/or permanent make up according to EU Commission Regulation 2020/2081. The concentration limit (by weight) is 0.0005%.

관련 반응

861건
반응 기록 만들기
HRID 13770 반응식
HRID 13770반응물로uspto-grants-2010_06
HRID 13772 반응식
HRID 13772반응물로uspto-grants-2010_06
HRID 71424 반응식
HRID 71424반응물로uspto-grants-2014_09
HRID 74103 반응식
HRID 74103반응물로uspto-grants-2014_09
HRID 76533 반응식
HRID 76533반응물로uspto-grants-2014_09
HRID 104122 반응식
HRID 104122반응물로Training data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 171859 반응식
HRID 171859반응물로Training data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 191386 반응식
HRID 191386반응물로Training data from https://doi.org/10.1039/C8SC04228D (6/10)
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새 노트새 반응견적 요청하기

5-nitro-o-toluidine is a bright yellow powder. (NTP, 1992)

Dry Powder

Yellow crystals; [ACGIH]

Dissociation ConstantspKa = 2.345 (conjugate acid)

물리화학적 성질

녹는점
103 · 103-106 °C(lit.)
끓는 점
294.61 °C · 294.61°C (rough estimate)
밀도
1.2333 · 1.2333 (estimate)
굴절률
1.6276 · 1.6276 (estimate)
저장 조건
2 · Keep in dark place,Sealed in dry,2-8°C
용해도
클로로포름(약간 용해됨), 메탄올(약간 용해됨)
물리적 상태
결정성 분말
산도 계수 (pKa)
2.34 · 2.34±0.10(Predicted)
색상
황토색에서 노란색-주황색까지
수용성
19 · 19ºC에서 <0.1g/100mL
BRN
879021 · 879021
Henry's Law Constant
1.2 · 1.2×103 mol/(m3Pa) at 25℃, HSDB (2015)
안정성
안정적인. 강한 산화제, 산 염화물, 산 무수물, 산, 클로로포르메이트와 호환되지 않습니다.
InChI
1S/C7H8N2O2/c1-5-2-3-6(9(10)11)4-7(5)8/h2-4H,8H2,1H3
InChIKey
DSBIJCMXAIKKKI-UHFFFAOYSA-N
SMILES
Cc1ccc(cc1N)[N+]([O-])=O
NIST
2 · Benzenamine, 2-methyl-5-nitro-(99-55-8)
EPA
2 · 2-Methyl-5-nitroaniline (99-55-8)

The major hazards encountered in the use and handling of 5-nitro-o-toluidine stem from its toxicologic properties. Dermal or inhalation exposure to this yellow, crystalline substance may occur from its production, handling, or use as a chemical intermediate for dyes and pigments. The EPA has designated 5-nitro-o-toluidine as a Group C carcinogen, ie, it is considered to be possibly carcinogenic to humans. If contact with this substance should occur, irrigate exposed eyes with copious amounts of tepid water for at least 15 minutes, and wash exposed skin thoroughly with soap and water. This substance is a candidate for rotary kiln and fluidized bed forms of incineration.

Reactive GroupNitro, Nitroso, Nitrate, and Nitrite Compounds, Organic
Special Reports · 2건

USEPA; Health and Environmental Effects Profile for 2-Methyl-5-nitroaniline EPA/600/X-87/091 (1989).

Bioassay of 5-Nitro-o-toluidine for Possible Carcinogenicity (1978) Technical Rpt Series No. 107 DHEW Pub No. (NIH) 78-1357, U.S. Department of Health Education and Welfare, National Cancer Institute, Bethesda, MD 20014

RCRA Requirements · 1건

U181; As stipulated in 40 CFR 261.33, when 5-nitro-o-toluidine, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

Reactivity Profile5-NITRO-O-TOLUIDINE is incompatible with strong oxidizing agents, acids, acid chlorides, acid anhydrides and chloroformates. (NTP, 1992)
DOT Emergency Guidelines · 5건

/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Health: TOXIC; inhalation, ingestion, or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. /Mononitrotoluidines; Nitrotoluidines (mono)/

/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors, and sewers explosion hazards. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. /Mononitrotoluidines; Nitrotoluidines (mono)/

/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas. /Mononitrotoluidines; Nitrotoluidines (mono)/

/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Mononitrotoluidines; Nitrotoluidines (mono)/

For more DOT Emergency Guidelines (Complete) data for 5-NITRO-O-TOLUIDINE (8 total), please visit the HSDB record page.

Air and Water ReactionsInsoluble in water. This compound is sensitive to moisture, light, or prolonged exposure to air.

안전 및 보호

Fire FightingFires involving this material should be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1건

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.

Fire Fighting Procedures · 1건

This chemical may burn but does not easily ignite. Use dry chemical, carbon dioxide, water spray, or alcohol or polymer foam extinguishers. Poisonous gases including nitrogen oxides are produced in fire. If materials or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Notify local health and fire officials and pollution control agencies. From a secure, explosion-proof location, use water spray to cool exposed containers. If cooling streams are ineffective (venting sound increases in volume and pitch, tank discolors, or shows any signs of deforming), withdraw immediately to a secure position. If employees are expected to fight fires, they must be trained and equipped.

Storage Conditions · 1건

Prior to working with this chemical you should be trained on its proper handling and storage. Store in tightly closed containers in a cool, well ventilated area away from oxidizers, strong acids, acid cholrides, acid anhydrides, chloroformates. Where possible, automatically pump liquid from drums or other storage containers to process containers. Sources of ignition such as smoking and open flames are prohibited where this chemical is handled, used, or stored. Metal containers involving the transfer of 5 gallons or more of this chemical should be grounded and bonded. Drums must be equipped with self-closing valves, pressure vacuum bungs, and flame arresters. Use only non-sparking tools and equipment, especially when opening and closing containers of this chemical. Wherever this chemical is used, handled, manufactured, or stored, use explosion-proof electrical equipment and fittings.

Cleanup Methods · 1건

Evacuate persons not wearing protective equipment from area of spill or leak until cleanup is complete. Remove all ignition sources. Use HEPA vacuum or wet method to reduce dust during clean-up. Do not dry sweep. Collect powdered material in the most convenient and safe manner and deposit in sealed containers. Ventilate area of spill or leak after clean-up is complete. It may be necessary to contain and dispose of this chemical as a hazardous waste. If material or contaminated runoff enters waterways, notify downstream users of potentially contaminated waters. Contact your Department of Environmental Protection or your regional office of the federal EPA for specific recommendations. If employees are required to clean-up spills, they must be properly trained and equipped.

Nonfire Spill Response · 1건

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol 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.

Disposal Methods · 3건

[40 CFR 240-280, 300-306, 702-799 (7/1/2006)] Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U181, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaiminant (>/= 100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal.

A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.

Preventive Measures · 3건

Wear protective gloves and clothing to prevent any reasonable probability of skin contact. Safety equipment suppliers/manufacturers can provide recommendations on the most protective glove/clothing material for your operation. All protective clothing (suits, gloves, footwear, headgear) should be clean, available each day, and put on before work. Contact lenses should not be worn when working with this chemical. Wear dust-proof chemical goggles and face shield unless full facepiece respiratory protection is worn. Employees should wash immediately with soap when skin is wet or contaminated. Provide emergency showers and eyewash.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Isolation and EvacuationExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Threshold Limit Values (TLV) · 4건

1.0 [mg/m3], inhalable fraction and vapor

8 hr Time Weighted Avg (TWA): 1 mg/cu m (inhalable fraction)

Excursion Limit Recommendation: Excursions in worker exposure levels may exceed 3 times the TLV-TWA for no more than a total of 30 minutes during a work day, and under no circumstances should they exceed 5 times the TLV-TWA, provided that the TLV-TWA is not exceeded.

A3: Confirmed animal carcinogen with unknown relevance to humans.

Protective Action Criteria (PAC) · 3건

3.0 [mg/m3]

19 [mg/m3]

110 [mg/m3]

Personal Protective Equipment (PPE) · 2건

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)

Where the potential for exposure to this chemical, use a MSHA/NIOSH approved supplied-air-respirator with a full facepiece operated in the positive pressure mode or with a full facepiece, hood, or helmet in the continuous flow mode, or use a MSHA/NIOSH approved self-contained breathing apparatus operated in a pressure-demand or other positive-pressure mode).

독성 정보

Ecotoxicity Values · 4건

EC50; Species: Pseudokirchneriella subcapitata (Green algae, log growth phase); Conditions: freshwater, static, 25 °C, pH 6.0-7.5; Concentration: 101.5 uM for 96 hr (95% confidence interval: 59.4-175.5 uM); Effect: decreased population abundance /formulated product/

EC50; Species: Daphnia magna (Water flea, first instar larvae); Conditions: freshwater, static, 20 °C, pH 7.2-8.6, hardness 26 mg/L CaCO3, alkalinity 45 mg/L CaCO3, dissolved oxygen 8.7 mg/L (8.6-8.8 mg/L); Concentration: 22500 ug/L for 48 hr; Effect: intoxication, immobilization /formulated product/

LC50; Species: Pimephales promelas (Fathead minnow, juvenile, length 2.4 cm, weight 0.28 g); Conditions: freshwater, static, 20.3 °C (19.5-22.0 °C), pH 7.6 (6.0-9.2), hardness 29.6 mg/L CaCO3 (12.0-43.0 mg/L), alkalinity 31.0 mg/L CaCO3 (15.0-60.0 mg/L), dissolved oxygen 7.2 mg/L (2.8-9.4 mg/L); Concentration: 68800 ug/L for 96 hr (95% confidence interval: 64200-74200 ug/L) /95-99% purity/

LC50; Species: Pimephales promelas (Fathead minnow, juvenile, weight 0.09 g, length 1.9 cm); Conditions: freshwater, static, 20 °C, pH 7.2-8.6, hardness 26 mg/L CaCO3, alkalinity 45 mg/L CaCO3, dissolved oxygen 8.2 mg/L (8.2-8.3 mg/L); Concentration: 71300 ug/L for 96 hr /formulated product/

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 690 and 810 reported in sewage sludge(2), indicates that 5-nitro-o-toluidine is expected to have low mobility in soil(SRC). Volatilization of 5-nitro-o-toluidine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.3X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 5-Nitro-o-toluidine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 9.8X10-4 mm Hg(SRC), determined from a fragment constant method(4). 5-Nitro-o-toluidine was reported to degrade 100% after 104 days in studies using activated sludge from a wastewater treatment plant with no previous exposure to nitroaromatic compounds, as well as in studies using inoculum from a plant that routinely treats dinitrotoluene-contaminated wastewater(5). Degradation products identified were 2,4-diaminotoluene, 4-nitrotoluene, and 6-nitroindazole(5).

AQUATIC FATE: Based on a classification scheme(1), Koc values of 690 and 810 reported in sewage sludge(2), indicates that 5-nitro-o-toluidine is 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 8.3X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4) According to a classification scheme(5), an estimated BCF of 5.5(SRC), from its log Kow of 1.87(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 5-Nitro-o-toluidine is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). 5-Nitro-o-toluidine was reported to degrade 100% after 104 days in studies using activated sludge from a wastewater treatment plant with no previous exposure to nitroaromatic compounds, as well as in studies using inoculum from a plant that routinely treats dinitrotoluene-contaminated wastewater(8). Degradation products identified were 2,4-diaminotoluene, 4-nitrotoluene, and 6-nitroindazole(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 5-nitro-o-toluidine, which has an estimated vapor pressure of 9.8X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 5-nitro-o-toluidine 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 1.4 days(SRC), calculated from its rate constant of 1.2X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 2-Methyl-5-nitrobenzenamine does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Food Survey Values5-Nitro-o-toluidine was detected not quantified as a volatile flavor component of Idaho Russet Burbank baked potatoes(1).
Adverse EffectsOccupational hepatotoxin - Primary hepatotoxins: the toxic effect to the liver is the principal adverse effect of the chemical.
Ongoing Test Status · 1건

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.[Available from: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=99-55-8]

Effluent Concentrations5-Nitro-o-toluidinehas been detected at levels ranging from 0.0020 to 0.10 mg/L in waste water effluent from a plant manufacturing 2,4,6-trinitrotoluene(1).
Medical SurveillanceBlood methemoglobin levels. Complete blood count (LBC). Liver function disease.
Soil Adsorption/MobilityKoc values of 690 and 810 were reported for 5-nitro-o-toluidine in sewage sludge(1). According to a classification scheme(2), these Koc values suggest that 5-nitro-o-toluidine is expected to have low mobility in soil.
Human Toxicity Excerpts · 3건

/SIGNS AND SYMPTOMS/ Methemoglobinemia is the major toxic effect observed following excessive absorption of 5-nitro-o-toluidine.. Symptoms of exposure include bluish lips and/or fingernails, headache, nausea, and fatigue

/SIGNS AND SYMPTOMS/ Methemoglobinemia ... is also the major toxic effect observed in workers following excessive exposure. In addition, upon dermal contact the compounds may irritate the skin and cause dermatitis.

/CASE REPORTS/ Of 15 workers in the same factory who handled 5-nitro-o-toluidine, three were hospitalized with symptoms of acute liver dysfunction. Suspecting a link between liver dysfunction and working conditions, ... workplace factors /were correlated/ with clinical findings in all 15 workers. ... Blood biochemistry tests indicated liver damage in seven of 15 study subjects. Workers who handled 5-nitro-o-toluidine and nitrosyl sulfuric acid often loosened their respiratory protective equipment shortly after 5-nitro-o-toluidine powder had been dispersed into the air of the room. No potential hepatotoxins were present except for 5-nitro-o-toluidine. Six of the affected workers had handled 5-nitro-o-toluidine 12 to 20 times; the seventh worker had handled the powder three times; and the other eight workers without liver dysfunction had handled the material once or twice. No other significant differences in background were evident between the affected and unaffected workers, such as age, sex, or protective measures. Histological findings during recovery from liver damage were similar to those of acute viral hepatitis. None of the 15 subjects has demonstrated liver damage since the factory was closed. ...

Artificial Pollution Sources5-Nitro-o-toluidine's production and use in the synthesis of dye pigments(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 1건

AEROBIC: 5-Nitro-o-toluidine was readily consumed in enrichment cultures using an inoculum from a munitions wastewater treatment plant(1). 5-Nitro-o-toluidine was reported to degrade 100% after 104 days in studies using activated sludge from a wastewater treatment plant with no previous exposure to nitroaromatic compounds, as well as in studies using inoculum from a plant that routinely treats dinitrotoluene-contaminated wastewater(2). Degradation products identified were 2,4-diaminotoluene, 4-nitrotoluene, and 6-nitroindazole(2).

Carcinogen Classification · 6건

5-Nitro-ortho-toluidine

Group 3: Not classifiable as to its carcinogenicity to humans

Volume 48: (1990) Some Flame Retardants and Textile Chemicals, and Exposures in the Textile Manufacturing Industry

1990

1989

5-Nitro-o-toluidine

규제 정보

RCRA Requirements · 1건

U181; As stipulated in 40 CFR 261.33, when 5-nitro-o-toluidine, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

CERCLA Reportable Quantities · 1건

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

안전 데이터

wgk
3
tsca
TSCA listed
rtecs
XU8225000
ridadr
UN 2660 6.1/PG 3
독성
LD50 orl-rat: 574 mg/kg NCIMR* NIH-71-E-2144,73
HS 번호
29214300
risk_code
23/24/25-40-52/53
hazard_code
T,Xi
safety_code
36/37-45-61
포장분류
III
위험 등급
6.1
기존화학 물질
KE-24453
위험 참고 사항
Irritant
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralAquatic Chronic 3Carc. 2
스토리지 클래스
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
유해 물질 데이터
99-55-8(Hazardous Substances Data)
Impurities
5-Nitro-ortho-toluidine is available commercially with a purity of 99% ... .
U.S. Imports · 2건

(1977) 7.10X10+6 G (PRINCPL CUSTMS DISTS)

(1982) 2.48X10+7 G (PRINCPL CUSTMS DISTS)

U.S. Production · 4건

2023: 50,000 - <250,000 lb

(1978) PROBABLY GREATER THAN 9.08X10+6 G

(1982) PROBABLY GREATER THAN 2.27X10+6 G

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#4830]

Consumption PatternsESSENTIALLY 100% AS CHEM INT FOR PIGMENTS & DYES.
Industry UsesIntermediate
Methods of Manufacturing · 3건

o-Toluidine is nitrated at -10 °C by slow addition of nitric acid to a solution of the amine in 98% sulfuric acid. On quenching the nitration mixture in water and allowing the temperature to rise, a solution is obtained from which the sulfate of the product crystallizes on cooling, leaving most of the 6-nitro-o-toluidine byproduct in solution.

REACTION OF O-ACETOTOLUIDIDE WITH NITRIC ACID IN CONCENTRATED SULFURIC ACID AND SUBSEQUENT SAPONIFICATION.

Several processes have been reported for the preparation of nitrotoluidines, including 5-nitro-ortho-toluidine. These include the reaction of nitrocresol with aqueous ammonia, the catalytic hydrogenation of aromatic nitro compounds in the presence of Raney copper, reacting aromatic nitro compounds with hydrogen sulfide in the presence of ammonia dissolved in dioxane, reacting 2,4-dinitrotoluene with hydrogen sulfide in a pyridine solution, and reacting 2,4-dinitrotoluene with carbon monoxide in the presence of cupric oxide and manganese dioxide... . 5-Nitro-ortho-toluidine has also been synthesized by the nitration of ortho-toluidine and the monoreduction of 2,4-dinitrotoluene with alcoholic ammonium sulfide ... . It can be prepared by the electrolytic reduction of ortho-nitrotoluene to orthotoluidine sulfate and subsequent nitration

Formulations/Preparations · 1건

Trade Names: Amarthol Fast Scarlet G Base; Amarthol Fast Scarlet G Salt; Azoene Fast Scarlet GC Base; Azoene Fast Scarlet GC Salt; Azofix Scarlet G Salt; Azogene Fast Scarlet G; Dainichi Fast Scarlet G Base; Daito Scarlet Base G; Devol Scarlet B; Devol Scarlet G Salt; Diabase Scarlet G; Diazo Fast Scarlet G; Fast Red SG Base; Fast Scarlet G; Fast Scarlet G Base; Fast Scarlet GC Base; Fast Scarlet G Salt; Fast Scarlet J Base; Fast Scarlet J Salt; Fast Scarlet M 4NT Base; Fast Scarlet T Base; Hiltonil Fast Scarlet G Base; Hiltonil Fast Scarlet GC Base; Hiltonil Fast Scarlet G Salt; Kayaku Scarlet G Base; Lake Scarlet G Base; Lithosol Orange R Base; Mitsui Scarlet G Base; Naphthanil Scarlet G Base; Naphtoelan Fast Scarlet G Base; Naphtoelan Fast Scarlet G Salt; Scarlet Base Ciba II; Scarlet Base Irga II; Scarlet Base NSP; Scarlet G Base; Sugai Fast Scarlet G Base; Symulon Scarlet G Base.

General Manufacturing Information · 2건

Synthetic Dye and Pigment Manufacturing

Benzenamine, 2-methyl-5-nitro-: ACTIVE

응용 분야

개요2-Methyl-5-nitroaniline, also known as 5-nitro-o-toluidine, is an intermediate compound in the synthesis of a wide range of azo dyes and is an in vivo metabolic product of 2,4-dinitrotoluene.

용도2-Methyl-5-nitroaniline may be employed as analytical standard for the surfactant mediated transformations (254nm) of 2,4-dinitrotoluene.

제조 방법

2-Methyl-5-nitrobenzenaminein concentrated sulfuric acid nitration.

상·하류 제품 정보

상류 원료

2-MethylacetanilideO-톨루이딘질산2-하이드록실아미노-4-니트로톨루엔Methanimidamide, N,N-dimethyl-N'-(2-methyl-5-nitrophenyl)-벤조산,4-아미노-5-메틸-2-니트로-(9CI)2-Bromo-4-nitrotoluene2-요오도-4-니트로톨루엔5-나이트로-o-톨루딘

하류 제품

3-클로로-6-니트로(1H)인다졸6-하이드록시인다졸6-아미노-3-클로로(1H)인다졸Disperse Yellow S-3GLPigment Fast Scarlet G3-요오도-6-니트로인다졸3-브로모-6-니트로인다졸Coating Brilliant Red6-니트로인다졸6-아미노-3-브로모(1H)INDAZOLEC.I. 염료 레드 85-나이트로-2-크레솔1-페닐-3,4-디히드로이소퀴놀린2,7-Naphthalenedisulfonic acid, 4-amino-6-[[4'-[(8-amino-1-hydroxy-5-sulfo-2-naphthalenyl)azo]-3,3'-dimethyl[1,1'-biphenyl]-4-yl]azo]-5-hydroxy-3-[(2-methyl-5-nitrophenyl)azo]-, trisodium salt5-나이트로-o-톨루딘

추가 설명

정의ChEBI: A C-nitro compound in which the nitro compound is meta to the amino group and para to the methyl group of o-toluidine.