2,3-다이아미노톨루엔

2,3-Diaminotoluene

HCID 17593CAS 2687-25-4

기본 정보

표준 SMILES
Cc1cccc(N)c1N
InChIKey
AXNUJYHFQHQZBE-UHFFFAOYSA-N
분자식
C7H10N2
평균 분자량
122.17 g/mol
단동위원소 질량
122.08439832

이름 및 식별자

우선 이름
2,3-Diaminotoluene
IUPAC
3-methylbenzene-1,2-diamine
현지명
2,3-다이아미노톨루엔
영어명
2,3-DIAMINOTOLUENE
분자식
C7H10N2
분자량
122.17

이름 및 동의어

2,3-DIAMINOTOLUENE3-methylbenzene-1,2-diamine2687-25-43-Methyl-1,2-benzenediamine3-Methyl-o-phenylenediamine1,2-Benzenediamine, 3-methyl-3-Methyl-1,2-phenylenediamine2,3-Tolylenediamine2,3-Toluylenediamine1,2-Diamino-3-methylbenzeneDTXSID4027494Toluene, 2,3-diamino-
이름 더 보기
2,3-다이아미노톨루엔3-메틸-1,2-벤젠디아민1,2-다이아미노-3-메틸벤젠2,3-디아미노톨루엔2,3-톨루엔다이아민2,3-톨릴렌다이아민2-아미노-3-메틸아닐린3-메틸-1,2-벤젠다이아민톨루엔-2,3-다이아민톨루엔-2,3-디아민2,3-DAT25KGS/DRUM2.3-DiaMinotol2,3-Dhamphetamine2,3-Diaminotoluone2,3-Diaminetoluene2,3-TOLUENEDIAMINE
1-Methyl-2,3-phenylenediamineSR8WC7LLQ2DTXCID807494RefChem:441961220-248-5Toluene-2,3-diamine2,3-Diaminotoluene-d32-Amino-3-methylphenylamine

데이터베이스 식별자

CAS
2687-25-4
PubChem CID
17593
DTXSID
DTXSID4027494
ChEMBL
CHEMBL3183504
UNII
SR8WC7LLQ2
EC Number
220-248-5
Nikkaji
J7.647C

물성

구조 계산 물성

XLogP
0.9
극성 표면적
52 Ų
수소 결합 공여자 수
2
수소 결합 수용자 수
2
회전 가능 결합 수
0
무거운 원자 수
9

실험 및 물리화학적 성질

Chemical ClassesNitrogen Compounds -> Amines, Aromatic
Color/FormCrystals
SolubilityVery soluble in acetone, benzene, ethanol
Boiling Point255 °C
DecompositionWhen heated to decomposition it emits toxic vapors of /nitrogen oxides/.
Melting Point63.5 °C

물리화학적 성질

녹는점
59 · 59-65 °C (lit.)
끓는 점
225 °C · 225°C
밀도
1.0343 · 1.0343 (rough estimate)
굴절률
1.5103 · 1.5103 (estimate)
인화점
225 °C · 225°C
저장 조건
Keep in dark place,Inert atmosphere,Room temperature

화학적 성질

brown powder

안전 및 규제

GHS 분류

GHS Classification · 6건

Danger

H301 (45.5%): Toxic if swallowed [Danger Acute toxicity, oral]

P203, P260, P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P301+P316, P301+P317, P302+P352, P304+P340, P305+P351+P338, P316, P317, P318, P319, P321, P330, P332+P317, P333+P317, P337+P317, P361+P364, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 264 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Warning

H302: Harmful if swallowed [Warning Acute toxicity, oral]

유해성 정보

Regulatory Information · 3건

Chemical: 1,2-Benzenediamine, 3-methyl-

1,2-Benzenediamine, 3-methyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,2-Benzenediamine, 3-methyl- 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: Cease Manufacture Update: 06-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/24442

Other Safety InformationIMAP assessments - Ortho-toluenediamines: Human health tier II assessment
Hazards Summary · 2건

External application to rabbit eyes scored 7 on a scale of 1-10 (10 being most severe) for degree of injury (2,3/3,4 mixture); Emergency treatment: Methemoglobinemia; [HSDB] Commercial mixture (2,3/3,4-TDA[40/60]): Oral LD50 (rat) = 660 mg/kg; Dermal LD50 (rabbit) => 5750 mg/kg; A mild skin and eye irritant; Toxic to reproduction and development, likely to be genotoxic, and possesses carcinogenic potential; [OECD SIDS] Ortho-TDA (mixture of 3,4 [50%], 2,3 [45%], and 2,4 [1%] TDA isomers): Causes male reproductive toxicity (decreased body weights and number of spermatids/g testes) and couple/developmental toxicity (decreased number of implantation sites and delivered pups and increased post-implantation loss and pup mortality) in gavage study of rats at 250 mg/kg/day; [EPA TSCA] See 2,4-Diaminotoluene.

The major hazards encountered in the use and handling of 2,3-diaminotoluene stem from its toxicologic properties. Toxic by inhalation and ingestion, exposure to this crystalline substance may occur from its use as a chemical intermediate for corrosion inhibitors, and antioxidants (eg, benzimidazolethiol derivatives). In activities and situations where over-exposure may occur, wear protective clothing and a self-contained breathing apparatus. If contact should occur, irrigate exposed eyes with copious amounts of tepid water for at least 15 minutes, and wash expsosed skin thoroughly with soap and water. Remove contaminated clothing and shoes at the site. While 2,3-diaminotoluene does not ignite easily, it may burn with the production of irritating or poisonous gases. Runoff from fire control water may cause pollution. For fires involving this substance, extinguish with dry chemical, CO2, Halon, water spray, fog, or standard foam. Small spills of 2,3-diaminotoluene should be placed in a clean, dry, covered container (if in solution, take up with sand or other noncombustible absorbent) for later disposal. For large spills of 2,3-diaminotoluene solution, dike far ahead of the spill for later disposal.

Special ReportsAnon; Diaminotoluenes, World Health Organization, 1211 Gen'eve 27, p. 1-67 (1987)
RCRA Requirements · 1건

U221; As stipulated in 40 CFR 261.33, when 2,3-Diaminotoluene 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).

TSCA Requirements · 1건

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1,2-Benzenediamine, 3-methyl is included on this list. Effective date: 4/29/83; Sunset date: 4/29/93.

안전 및 보호

Disposal Methods · 2건

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.

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

Preventive Measures · 5건

The worker should immediately wash the skin when it becomes contaminated. /Toluenediamine/

The worker should wash daily at the end of each work shift, and prior to eating, drinking, smoking, etc. /Toluenediamine/

Work clothing that becomes wet or significantly contaminated should be removed or replaced. /Toluenediamine/

Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises. /Toluenediamine/

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. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.

Personal Protective Equipment (PPE) · 5건

Wear appropriate personal protective clothing to prevent skin contact. /Toluenediamine/

Wear appropriate eye protection to prevent eye contact. /Toluenediamine/

Eyewash fountains should be provided in areas where there is any possbility that workers could be exposed to the substance; this is irrespective of the recommendation involving the wearing of eye protection. /Toluenediamine/

Facilities for quickly drenching the body should be provided within the immediate work area for emergency use where there is a possibility of exposure. [Note: It is intended that these facilities provide a sufficient quantity or flow of water to quickly remove the substance from any body areas likely to be exposed. The actual determination of what constitutes an adequate quick drench facility depends on the specific circumstances. In certain instances, a deluge shower should be readily available, whereas in others, the availability of water from a sink or hose could be considered adequate.] /Toluenediamine/

For more Personal Protective Equipment (PPE) (Complete) data for 2,3-DIAMINOTOLUENE (6 total), please visit the HSDB record page.

Immediately Dangerous to Life or Health (IDLH)NIOSH considers toluenediamine to be a potential occupational carcinogen. /Toluenediamine/

독성 정보

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 56(SRC), determined from a structure estimation method(2), indicates that 2,3-diaminotoluene is expected to have high mobility in soil(SRC). However, aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(3,4), suggesting that mobility may be much lower in some soils. Volatilization of 2,3-diaminotoluene from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 9.5X10-010 atm-cu m/mole(SRC), using a fragment constant estimation method(5). 2,3-Diaminotoluene is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 5.53X10-4 mm Hg at 25 °C(6). Biodegradation data in soil were not available(SRC, 2012).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 56(SRC), determined from a structure estimation method(2), indicates that 2,3-diaminotoluene 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 9.5X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of 0.71(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data in water were not available(SRC, 2012).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,3-diaminotoluene, which has a vapor pressure of 5.53X10-4 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 2,3-diaminotoluene 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 1.2 hours(SRC), calculated from its rate constant of 2.0X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 2,3-diaminotoluene will be removed from the atmosphere by wet and dry deposition. By analogy to toluene-2,4-diamine which absorbs light at wavelengths >294 nm(4), 2,3-diaminotoluene may be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Soil Adsorption/Mobility · 1건

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 2,3-diaminotoluene can be estimated to be 56(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2,3-diaminotoluene is expected to have high mobility in soil. However, aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(3,4), suggesting that mobility may be much lower in some soils(SRC). Aromatic amines (such as the toluidine isomers) have been observed to undergo rapid and reversible covalent bonding with humic materials in aqueous solution; the initial bonding reaction is followed by a slower and much less reversible reaction believed to represent the addition of the amine to quinoidal structures followed by oxidation of the product to give an amino-substituted quinone; these processes represent pathways by which aromatic amines may be converted to latent forms in the biosphere(5). The estimated pKa of 2,3-diaminotoluene is 4.91(6), indicating that this compound will exist partially in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(7).

Artificial Pollution Sources2,3-Diaminotoluene's formation as a minor by-product during the industrial manufacture of other diaminotoluene isomers(1) may result in its release to the environment through various waste streams(SRC).
Environmental Bioconcentration · 1건

An estimated BCF of 3 was calculated in fish for 2,3-diaminotoluene(SRC), using an estimated log Kow of 0.71(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 · 1건

The Henry's Law constant for 2,3-diaminotoluene is estimated as 9.5X10-10 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2,3-diaminotoluene is expected to be essentially nonvolatile from water and moist soil surfaces(2). 2,3-Diaminotoluene is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 5.53X10-4 mm Hg(3).

규제 정보

RCRA Requirements · 1건

U221; As stipulated in 40 CFR 261.33, when 2,3-Diaminotoluene 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).

TSCA Requirements · 1건

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1,2-Benzenediamine, 3-methyl is included on this list. Effective date: 4/29/83; Sunset date: 4/29/93.

안전 데이터

wgk
3
tsca
TSCA listed
rtecs
XS9550000
ridadr
2811
독성
mouse,LD50,intraperitoneal,286mg/kg (286mg/kg),Genetica Polonica. Vol. 26, Pg. 109, 1985.
HS 번호
29214990

화학 및 산업

약리 정보

Metabolism/Metabolites · 1건

The acetylation of amino groups, oxidation of methyl groups, and ring hydroxylation appear to be the major metabolic steps. Phenolic metabolites and trace amounts of unchanged diaminotoluenes are excreted in the urine of experimental animals.

용도 및 제조

Uses · 4건

Used as a chemical intermediate for tolyltriazole (corrosion inhibitor); Manufactured by two US companies as 65:35 mixture of 3,4- and 2,3-diaminotoluenes; Also found as minor impurity in production of other diaminotoluene isomers; [HSDB] Only commercially available as 40:60 mixture of the ortho (2,3- and 3,4) isomers used as co-reactants or raw materials in the production of dyes, corrosion inhibitors, urethane products, and rubber antioxidants; Also used to lesser extent to make mercaptotoluimidazole and its zinc salt (specialty antioxidants in nitrile rubber elastomers) and as substitute for o-phenylenediamine in epoxy resin curing, polymer initiating, cross-linking, chain extending, and capping; The commercial mixture may be represented by CAS #'s 25376-45-8 and 26966-75-6 (although these CAS #'s may also be used for other isomeric mixtures); [OECD SIDS]

CHEM INT FOR TOLYLTRIAZOLE USED AS A CORROSION INHIBITOR; CHEM INT FOR ANTIOXIDANTS, EG, BENZIMIDAZOLETHIOL DERIVS

Commercial mixtures of 2,3- and 3,4- isomers, as well as the 2,4- and 2,6-isomers, are used as co- reactants or as raw materials in the manufacture of urethane products, dyes, corrosion inhibitors, and rubber antioxidants. Diaminotoluene isomers have relatively limited use as epoxy curing agents and as photographic developers. The most commonly marketed isomers and isomer mixtures are ... Ortho-DAT (3,4-, 2,3-isomers, as 60:40 mixture)...

Used mainly in the manufacture of dyes and dye intermediates /Toluenediamines/

U.S. Production · 6건

2023: 2,500,000 - <4,000,000 lb

(1977) AT LEAST 1.45X10+9 GRAMS

(1982) MORE THAN 2.27X10+6 G-AS ISOMERIC MIXT

1,2-Benzenediamine, 3-methyl- 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#5689]

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 1,2-Benzenediamine, 3-methyl-. Aggregated National Production Volume: 1 to < 10 million pounds.

Industry UsesPolymerization promoter
Methods of ManufacturingNITRATION OF M-NITROTOLUENE FOLLOWED BY CATALYTIC HYDROGENATION; BYPRODUCT IN THE MFR OF 2,4- & 2,6-TOLUENEDIAMINE (CHEM INTS FOR TOLUENE DIISOCYANATE)
General Manufacturing Information · 3건

All Other Basic Organic Chemical Manufacturing

1,2-Benzenediamine, 3-methyl-: ACTIVE

Formed as a minor by-product during the industrial manufacture of other diaminotoluene isomers

응용 분야

용도Inducer of CYP1A activity, and possible mutagenic carcinogen.

일반 설명The antitumour activity of Pd(II) and Pt(II) new complexes with 2,3-diaminotoluene was studied. 2,3-Diaminotoluene induced CYP1A activity.

공급사50 곳

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
苏州启航生物科技有限公司18151111370 · [email protected]
武汉欣扬瑞和化学科技有限公司153-07155313 15307155313 · [email protected]

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