Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
M-페닐렌다이아민
1,3-벤젠다이아민 · M-페닐렌다이아민 · m-페닐렌디아민 · m-페닐렌다이아민및그염류 · 1,3-다이아미노벤젠 · 1,3-다이아미노페닐렌 · 1,3-벤젠디아민 · 1,3-페닐렌다이아민
식별자 및 물리적 특성
| CAS No. | 108-45-2 |
|---|---|
| 분자식 | C6H8N2 |
| 평균 분자량 | 108.14 g/mol |
| 단동위원소 질량 | 108.06874826 g/mol |
| SMILES | Nc1cccc(N)c1 |
| InChIKey | WZCQRUWWHSTZEM-UHFFFAOYSA-N |
| PubChem CID | 7935 |
| ChEMBL | CHEMBL1595914 |
| ChEBI | CHEBI:8092 |
| EC No. | 203-584-7 |
| DTXSID | DTXSID4021137 |
| 현지명 | M-페닐렌다이아민 |
화학 및 물리적 성질
| XLogP | -0.3 |
|---|---|
| 극성 표면적 | 52 |
| 수소 결합 공여자 수 | 2 |
| 수소 결합 수용자 수 | 2 |
| 회전 가능 결합 수 | 0 |
| 무거운 원자 수 | 8 |
| 형식 전하 | 0 |
| 복잡도 | 64.9 |
| 물질 분류 | Nitrogen Compounds -> Amines, Aromatic |
| 화장품 | Cosmetic ingredients (m-Phenylenediamine) -> CIR (Cosmetic Ingredient Review) |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| 농약 | Pesticide -> EPA IRIS |
| LogP(분배 계수) | log Kow = -0.330.0 |
| 밀도 | 1.0696 at 136 °F (NTP, 1992) - Denser than waterwill sink1.0096 g/cu cm at 58 °CDensity = 1.1391.14 g/cm³1.139 @25 °C1,139 g/cm3 |
| Color/Form | WHITE CRYSTALS BECOMING RED ON EXPOSURE TO AIRColorless needlesRHOMBIC CRYSTALS FROM ALCOHOLCOLORLESS RHOMBIC NEEDLESDark oxidation products /are/ present in compound exposed to moist air. |
| 용해도 | less than 1 mg/mL at 66 °F (NTP, 1992)SOL IN WATER, METHANOL, ETHANOL, CHLOROFORM, ACETONE, DIMETHYLFORMAMIDE, METHYL ETHYL KETONE, DIOXANESLIGHTLY SOL IN ETHER, CARBON TETRACHLORIDE, ISOPROPANOL, DIBUTYL PHTHALATE. VERY SLIGHTLY SOL IN BENZENE, TOLUENE, XYLENE, BUTANOL.In water, 2.38X10+5 mg/l at 20 degSolubility in water: soluble350g/L |
| 인화점 | 280 °F (NTP, 1992)187 °C c.c.>230 °F |
| 끓는 점 | 540 to 543 °F at 760 mmHg (NTP, 1992)284-287 °C540-543 °F287 °C @760 [mm Hg]282-284 °C |
| Decomposition | WHEN HEATED TO DECOMP, IT EMITS TOXIC FUMES OF NITROGEN OXIDES. |
| 녹는점 | 145 to 147 °F (NTP, 1992)145-147 °F62-63 °C65 °C64-66 °C |
| 증기 밀도 | 3.7 (vs air) |
| 증기압 | 0.62 mm Hg ( 100 °C) |
| 굴절률 | 1.6339 |
| 저장 조건 | Store below +30°C. |
| 물리적 상태 | 펠릿 |
| pKa(산도 계수) | 5.11, 2.50(at 20℃) |
| 색상 | 노란색에서 밝은 황갈색 또는 갈색 회색 |
| pH | 8 (100g/l, H2O, 20℃) |
| 용해도 | 350 g/L (25 ºC) |
| 비열 | Cp(crystal): 1.48 J/(g·K), at 25℃ |
| Merck | 14,7283 |
| BRN | 471357 |
| 헨리 상수 | 7.9×103 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| 안정성 | 공기에 민감한 |
| 화장품 원료 기능 | 머리 염색 |
| InChI | 1S/C6H8N2/c7-5-2-1-3-6(8)4-5/h1-4H,7-8H2 |
| InChIKey | WZCQRUWWHSTZEM-UHFFFAOYSA-N |
| SMILES | Nc1cccc(N)c1 |
| LogP(분배 계수) | -0.39 at 20℃ |
| NIST | 1,3-Benzenediamine(108-45-2) |
| EPA | 1,3-Phenylenediamine (108-45-2) |
화학적 성질
m-Phenylenediamine is a colorless to white crystalline substance that turns red upon exposure to air
안전 및 규제
| GHS 분류 | DangerH301: Toxic if swallowed [Danger Acute toxicity, oral]P203, P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P318, P321, P330, P333+P317, P337+P317, P361+P364, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)H301+H311+H331 (23.9%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oralacute toxicity, dermalacute toxicity, inhalation] |
|---|---|
| 규제 정보 | Chemical: 1,3-Benzenediamine1,3-Benzenediamine is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3-Benzenediamine 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: 28-05-2020 https://echa.europa.eu/registration-dossier/-/registered-dossier/143861,3-Phenylenediamine: Does not have an individual approval but may be used under an appropriate group standardThe 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.) |
| 기타 안전 정보 | IMAP assessments - 1,3-Benzenediamine: Human health tier II assessment |
| 운송 라벨(DOT) | Poison |
| 화재 위험 | This chemical is combustible. Dust may form explosive mixtures in air (NTP, 1992)Combustible. Gives off irritating or toxic fumes (or gases) in a fire. |
| 화재 가능성 | FIRE POINT: 175 °C.Combustible when exposed to heat or flame. |
| 건강 유해성 | SYMPTOMS: Symptoms of exposure to this chemical may include skin sensitization reactions, eye irritation and injury, skin irritation, dermatitis, blackened skin and bronchial asthma. Other symptoms may include allergic skin reactions, irritation of the mucous membranes, nose, throat and lungs, coughing, burning sensation, runny nose, sore throat, methemoglobinemia, cyanosis, headache, dizziness, drowsiness, mental confusion, pulmonary edema, kidney and liver damage, central nervous system effects and conjunctivitis. Eye contact may cause discomfort, tearing, blurring of vision, reddening, partial clouding of the cornea and swelling of the eye and surrounding tissue. Dysuria and eosinophiluria may also occur. Exposure may also result in respiratory tract irritation. |
| 유해성 요약 | In acute studies at lethal doses (650 mg/kg), animals have tremors, convulsions, cyanosis, and methemoglobinemia. In subchronic studies, rats have increased liver weights. Critical Effects are irritationConfirmed Animal Carcinogen with Unknown Relevance to Humans[ACGIH] Danger of skin sensitization[MAK] |
| 반응성 그룹 | Amines, Aromatic |
| EC 분류 | Symbol: T, NR: 23/24/25-36-43-50/53-68S: (1/2)-28-36/37-45-60-61 |
| UN 분류 | UN Hazard Class: 6.1UN Pack Group: III |
| Special Reports | ITC/USEPAInformation Review #102 (Draft) m-Phenylenediamine (1979)TRDB/USEPATechnical Support Document (Draft) Phenylenediamines (1984)NIOSH: Current Intelligence Bulletin 2,4-Diaminoanisole #19 (1978)TSCA CHIPs present a preliminary assessment of 1,4-Benzenediamine's potential for injury to human health & the environment (available at EPA's TSCA Assistance Office: (202) 554-1404 or (800) 424-9065).PHENYLENEDIAMINESRESPONSE TO INTERAGENCY TESTING COMMITTEEFED REGIST 47(5) 973 (1982). EVIDENCE IS GIVEN SUPPORTING TESTING OF THE CLASS OF COMPOUNDS PHENYLENEDIAMINES FOR THEIR TOXIC EFFECTS ON HUMAN HEALTH AND THE ENVIRONMENT. THE RESULTS OF TOXICITY TESTING OF 22 COMPOUNDS ARE TABULATED AS ARE THE EFFECTS FOR WHICH TESTING IS BEING CONSIDERED FOR 13 COMPOUNDS, AND THE USES OR POTENTIAL USES OF 47 PHENYLENEDIAMINES. |
| TSCA 요건 | 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. 1,3-Benzenediamine is included on this list.Manufacturers and processors of meta-phenylenedimine are required to conduct health efffects, chemical fate and environmental effects testing under TSCA section 4. |
| 소화 | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:Use water spray, powder. |
| 응급 조치 | Fresh air, rest. Refer for medical attention.Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Refer for medical attention . |
| 응급 처치 | 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. |
| 안전 보관 | Separated from strong oxidants and food and feedstuffs. Keep in the dark. Well closed. |
| 보관 조건 | KEEP WELL CLOSED & PROTECTED FROM LIGHT. |
| 비화재 누출 대응 | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| 처리 방법 | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.Recommendable method: Incineration. Peer-review: (Peer-review conclusions of an IRPTC expert consultation (May 1985)) |
| 누출 처리 | Personal protection: complete protective clothing including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. |
| Isolation and Evacuation | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Eye Prevention | Wear safety goggles, face shield or eye protection in combination with breathing protection. |
| Fire Prevention | NO open flames. |
| Inhalation Risk | A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °Con spraying or dispersing, however, much faster. |
| 상호 작용 | Paraoxon (diethyl-p-nitrophenylphosphate) is the toxic, but non-mutagenic metabolite of the organophosphorus ester insecticide parathion. ... A mutagenic synergy when paraoxon was incubated with plant activated m-phenylenediamine (mPDA) or with direct acting 2-acetoxyacetylaminofluorene ... and Salmonella typhimurium tester strains /was discovered/. ... /With/ non-toxic concn of plant activated mPDA and paraoxon a 10-fold incr in the mutant yield of S. typhimurium was observed. The mutagenicity of the plant activated mPDA product required that O-acetyltransferase (OAT) be expressed by the S. typhimurium tester strain. However, the paraoxon dependent mutagenic synergy was observed using the direct acting arylamine metabolite, 2AAAF, with strains YG1024, TA98 and TA98/1,8-DNP6 regardless of their OAT activity. This mutagenic synergy is dependent upon the presence of an activated acetylated form of the arylamine. The data presented here demonstrate that this mutagenic synergy is limited to paraoxon and not to the parent compound (parathion) or to a major metabolite of parathion (p-nitrophenol). |
| 표적 장기 | Hepatic |
| 환경 거동 | TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 16(SRC), determined from a measured log Kow of -0.33(2) and a recommended regression-derived equation(3), indicates that 1,3-benzenediamine is expected to have very high mobility in soil(SRC). However, anilines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(4,5)therefore, mobility may be much lower in some soils(SRC). Volatilization of 1,3-benzenediamine is not expected to be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 1.3X10-9 atm-cu m/mole(SRC), from its extrapolated vapor pressure, 2.1X10-3 mm Hg(6), and measured water solubility, 2.4X10+5 mg/l(7). 1,3-Benzenediamine is not expected to volatilize from dry soil surfaces based on its extrapolated vapor pressure(6). Limited biodegradation data indicate 1,3-benzenediamine may be resistant to biodegradation in soilsoil microflora did not cleave the benzene ring of 1,3-benzenediamine in 64 days(8).AQUATIC FATE: Based on a recommended classification scheme(1), an estimated Koc value of 16(SRC), determined from a measured log Kow of -0.33(2) and a recommended regression-derived equation(3), indicates that 1,3-benzenediamine is not expected to adsorb to suspended solids and sediment in water(SRC). However, aromatic amines are recognized as having a strong affinity to organic carbon, suggesting that this compound may bind strongly to suspended organic material in water(4,5). 1,3-Benzenediamine is not expected to volatilize from water surfaces(3,SRC) based on an estimated Henry's Law constant of 1.3X10-9 atm-cu m/mole(SRC), derived from its extrapolated vapor pressure, 2.1X10-3 mm Hg(6), and measured water solubility, 2.4X10+5 mg/l(7). 1,3-Benzenediamine may exist partially in the ionized form at environmental pH's based on pKa values of 2.65 and 4.88 at 25 °C(8). Volatilization of the ionized form is not expected to be an important fate process(SRC). According to a classification scheme(9), BCF values of 1.3 to 4.6 and <1.6 to 24 measured for 1,3-benzenediamine in carp at 2 and 0.2 mg/l, respectively(10), suggest that bioconcentration in aquatic organisms is low(SRC). 1,3-Benzenediamine in the water column may be susceptible to significant photooxidation via hydroxyl and peroxy radicalshalf-lives for these photooxidations may be on the order of 19-30 sunlight hours(11). Aqueous screening studies indicate 1,3-benzenediamine may be susceptible to microbial degradation(SRC)60% degradation was observed after 5 days using an acclimated activated sludge inoculum(12). 1,3-Benzenediamine was reported to be toxic to 3 unacclimated sludges at concns greater than 50 ppm(13).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,3-benzenediamine, which has an extrapolated vapor pressure of 2.1X10-3 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,3-benzenediamine 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 about 1.9 hours(3,SRC). 1,3-Benzenediamine absorbs light in the environmental spectrum(4), which suggests a potential for direct photolysis in the environment(SRC). |
| 유해 작용 | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. |
| 노출 경로 | The substance can be absorbed into the body by inhalation of its vapour, through the skin and by ingestion. |
| 독성 요약 | On the basis of the animal and clinical data included in this report, the CIR Expert Panel concludes that m-Phenylenediamine and m-Phenylenediamine Sulfate are safe for use in hair dyes at concentrations of up to 10%.Safe for use in cosmetics, with qualifications |
| Signs and Symptoms | Blue lips, fingernails and skin. Confusion. Convulsions. Dizziness. Headache. Nausea. Unconsciousness.MAY BE ABSORBED! Redness. Further see Inhalation.Redness. Pain. |
| ICSC Environmental Data | The substance is toxic to aquatic organisms. |
| EPA IRIS Information | m-PhenylenediamineHepatic6 x 10 ^-3 mg/kg-day |
| Soil Adsorption/Mobility | The Koc of 1,3-benzenediamine is estimated as approximately 16(SRC), using a measured log Kow of -0.33(1) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that 1,3-benzenediamine is expected to have very high mobility in soil(SRC). However, anilines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(4,5)therefore, mobility may be much lower in some soils(SRC). |
| TSCA Test Submissions | m-Phenylenediamine (CAS # 108-45-2) commercial grade, was evaluated for dermal carcinogenicity in 24-month skin-painting study with male and female C3H and C57BL/6 mice (40 and 20/sex/group, respectively) exposed daily to doses of 0.6 or 3.0 mg/day. Mice were sacrificed for histologic evaluation at a rate and time determined by incidence of tumor-bearing mice during the course of treatment. Study lethalities and survivors killed at termination of study were necropsied for examination of major organ systems and the brain to determine degree of substance absorption and potential systemic toxicity. Diagnosis of any gross pathology upon these analyses were confirmed histologically. In 24-month study, mortality was significantly higher in the 3 mg, B6 males, however no increased risk of skin tumors was established for either strain or sex of mice in association with treatment.meta-Phenylenediamine (CAS # 108-45-2) was evaluated for clastogenic effects in male and female Crl:CDBR mice (5-6/sex/group) following gavage dosing (2 doses, 24 hours apart) at concentrations of 0, 16, 33, and 65 mg/kg bodyweight. Five animals/sex/group were sacrificed for harvest of femur bone marrow and 1000 polychromatic erythrocytes/animal at 24 hours (all treatment groups) and 48 hours (0 and 65 mg/kg/day groups) after a second dose. Bone marrow smears were analyzed for treatment-related incidence of micronuclei in polychromatic erythrocytes. At all dose levels, in vivo observations included lethargy, half-closed eyes, and labored and/or rapid breathing. A solitary 65 mg/kg/day male found dead 24 hours after a second dose comprised the study mortality and weight loss in 33 and 65 mg/kg/day treatment groups was statistically significant. Upon cytogenetic evaluation, there was no statistically significant increase in micronucleated polychromatic erythrocytes in any treatment group relative to vehicle control (deionized water). The only statistically significant (p < 0.05Dunnett's test) finding from all bone marrow smears was a reduction in young, polychromatic erythrocytes.m-Phenylenediamine (CAS # 108-45-2) was evaluated for acute oral neurotoxicity in Crl:CDBR rats (12/sex/group) administered single gavage doses of 0, 75, 150, and 300 mg/kg (10 ml/kg in sterile water). Bodyweight, feed consumption, clinical signs, functional observational battery performance, fore-, and hindlimb grip strength, foot splay, and motor activity were assessed prior to treatment (baseline values), and at 1 hour, 24 hours, and 4 days post-treatment. Toxicity was demonstrated at all dose levels and generally to a greater extent in females. Females at the 150 and 300 mg/kg dose level, one and eight rats, respectively, were found dead prior to scheduled sacrifice, death occurring from 2-4 days after treatment. All study lethalities were found with pallor and staining. Significant weight loss within one day of dosing and persisting throughout Day 4 was common to 150 and 300 mg/kg treatment groups, while food consumption was adversely affected in a dose-related manner. A rebounding of food consumption and bodyweights was noted thereafter. Clinical signs were apparent from day of dosing and included dose-related pallor in females, and irregular head movements, coloration of urine and a tip-toe gait in males and females. The functional observational battery revealed significant general malaise, postural changes, and palpebral closure. High-dose females also showed diminished arousal. Measurements of fore- and hindlimb grip strength and foot splay were not indicative of a neurotoxicity at any treatment level. Motor activity was significantly depressed following treatment in all treatment groups relative to control (p </= .01), exhibiting a dose-related rate of recovery in the respective groups. Study authors attributed depressed motor activity to a general condition of malaise and reported no evidence of neurotoxicity.meta-Phenylenediamine (CAS # 108-45-2) was evaluated for subchronic oral neurotoxicity in male and female Crl:CDBR rats (10/sex/group) administered daily gavage doses of 0, 5, 10, and 20 mg/kg for 90 consecutive days. A functional observational battery and motor activity tests were conducted prior to dosing and at weeks 4, 8, and 13 during treatment. Male rats only exhibited minimal dose-related reductions in both horizontal (10 and 20 mg/kg groups) and vertical motor activity (20 mg/kg group) during treatment weeks 4 and 8 relative to controls. Study authors attributed these findings, which were not statistically significant, to general malaise characterized by lethargy rather than a direct effect of treatment on the central nervous system. Neuropathological evaluation at termination of study yielded no anomalies within the nervous system or skeletal muscle.For more TSCA Test Submissions (Complete) data for 1,3-BENZENEDIAMINE (8 total), please visit the HSDB record page. |
| Natural Pollution Sources | 1,3-Benzenediamine is of anthropogenic origin and is not known to be produced by natural sources. (SRC) |
| 수질 위해 등급(WGK) | 2 |
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | SS7700000 |
| 운송 번호(UN) | UN 1673 (PHENYLENEDIAMINES (o-, m-, p-)) |
| 독성 | LD50 in rats (mg/kg): 650 orally283 i.p. (Burnett) |
| 관세 코드 | 29215119 |
| 위험 문구(R) | 23/24/25-36-43-50/53-68-40 |
| 위험 표시 | T,N |
| 안전 문구(S) | 28-36/37-45-60-61-28A |
| 포장분류 | III |
| 위험 등급 | 6.1Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1Eye Irrit. 2Muta. 2Skin Sens. 1 |
| 기존화학 물질 | KE-02175 |
| F 고인화성물질 | 8-10-23 |
| 자연 발화 온도 | 560 °C |
| 저장 분류 | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| 유해 물질 데이터 | 108-45-2(Hazardous Substances Data) |
| 함량 및 규제정보 | 물질구분: 유독물질혼합물(제품)함량정보: 페닐렌디아민과 그 염류 및 이를 25% 이상 함유한 혼합물 |
| 유해화학물질 필터링 | 97-1-334 |
용도
용도
The appearance of the high purity of the m-phenylenediamine is snow white flake solid used as a synthetic electronic grade polyimide material and epoxy resin curing agent.
일반 설명
Colorless or white colored needles that turn red or purple in air. Melting point 64-66 C. Density 1.14 g / cm3. Flash point 280 F. May irritate skin and eyes. Toxic by skin absorption, inhalation or ingestion. Used in aramid fiber manufacture, as a polymer additive, dye manufacturing, as a laboratory reagent, and in photography.