化工社化工社 化学情報印刷レポート · 研究参考用
4,4'-ビ[2-クロロアニリン]
4,4'-ジアミノ-3,3'-ジクロロビフェニル · クリタンC-126 · 3,3'-ジクロロベンジジン · 3,3'-ジクロロビフェニル-4,4'-ジアミン · 3,3'-ジクロロ-[1,1'-ビフェニル]-4,4'-ジアミン · 4,4'-ビ[2-クロロアニリン] · 3,3'-ジクロロ-4,4'-ジアミノジフェニル · 3,3'-ジクロロ-1,1'-ビフェニル-4,4'-ジアミン
![4,4'-ビ[2-クロロアニリン] の分子構造式](/img/chemical/7070.png)
識別子と物理属性
| CAS No. | 86349-58-8 |
|---|---|
| 分子式 | C12H10Cl2N2 |
| 平均分子量 | 253.12 g/mol |
| 単同位体質量 | 252.02210368 g/mol |
| SMILES | Nc1ccc(-c2ccc(N)c(Cl)c2)cc1Cl |
| InChIKey | HUWXDEQWWKGHRV-UHFFFAOYSA-N |
| PubChem CID | 7070 |
| ChEMBL | CHEMBL314470 |
| ChEBI | CHEBI:82315 |
| EC No. | 202-109-0 |
| DTXSID | DTXSID6020432 |
| 現地名 | 4,4'-ビ[2-クロロアニリン] |
化学・物理的性質
| XLogP | 3.5 |
|---|---|
| 極性表面積 | 52 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 1 |
| 重原子数 | 16 |
| 形式電荷 | 0 |
| 複雑度 | 213 |
| 物質分類 | Hazardous Air Pollutants (HAPs)Nitrogen Compounds -> Benzidine and DerivativesCarcinogensSemi-Volatile Organic Compound (SVOC) |
| pH | Weak base |
| SpringerMaterials Properties | Crystal structure |
| 農薬 | Pesticide -> EPA IRIS |
| LogP（分配係数） | log Kow = 3.51 |
| Color/Form | Needles from alcohol or benzeneWhite crystalline solidGray to purple, crystalline solid |
| 溶解度 | 0.07 % at 59 °F (NIOSH, 2024)Solubility in water: 2-4% at 22 °C and pH 4.6 to pH 8.9 /Dihydrochloride salt/In water, 3.1 mg/L at 25 °CModerately soluble in alcoholreadily soluble in etherSoluble in acetic acid, benzene, and ethanolSlightly soluble in dilute hydrochloric acidエタノール、ベンゼン、氷酢酸に可溶 (Windholz et al., 1983)3.114mg/L(25℃) |
| 沸点 | 788 °F at 760 mmHg (NIOSH, 2024)368 °C402 °C @760 [mm Hg]398.89°C (rough estimate) |
| Decomposition | When heated to decomposition it emits very high toxic fumes of /hydrogen chloride and nitrogen oxides./ |
| 融点 | 270 to 271 °F (NTP, 1992)132.5 °C132-133 °C270-271 °F132.5°C |
| Physical Description | 3,3'-dichlorobenzidine is a gray to purple crystalline powder. Insoluble in water. Very toxic. Used in the dye industry, curing agent for isocyanate terminated resins.Gray to purple, crystalline solid[NIOSH]GREY-TO-PURPLE CRYSTALS.Gray to purple, crystalline solid. |
| Dissociation Constants | pKa1 = 1.6pKa2 = 3.2 |
| 密度 | 1.3171 (rough estimate) |
| 蒸気圧 | 4.2 x 10-7 at 25 °C (estimated, Howard, 1989) |
| 屈折率 | 1.6400 (estimate) |
| 引火点 | 10 °C |
| 貯蔵条件 | 2-8°C |
| pKa（酸解離定数） | 2.70±0.10(Predicted) |
| ヘンリー定数 | 4.5 x 10-8 atmm3/mol at 25 °C (estimated, Howard, 1989) |
| 安定性 | 安定。強力な酸化剤とは相容れない。 |
| 主な用途 | 洗浄剤化粧品環境食品および飲料パーソナルケア |
| InChI | 1S/C12H10Cl2N2/c13-9-5-7(1-3-11(9)15)8-2-4-12(16)10(14)6-8/h1-6H,15-16H2 |
| InChIKey | HUWXDEQWWKGHRV-UHFFFAOYSA-N |
| SMILES | Clc1c(ccc(c1)c2cc(c(cc2)N)Cl)N |
| CAS データベース | 91-94-1(CAS DataBase Reference) |
| NISTの化学物質情報 | [1,1'-Biphenyl]-4,4'-diamine, 3,3'-dichloro-(91-94-1) |
| EPAの化学物質情報 | 3,3'-Dichlorobenzidine (91-94-1) |
化学的特性
colourless to white crystalline solid
安全性と法規制
| GHS 分類 | DangerH312: Harmful in contact with skin [Warning Acute toxicity, dermal]P203, P261, P272, P273, P280, P302+P352, P317, P318, P321, P333+P317, P362+P364, P391, P405, and P501 (click each P-code to see the statement)H312 (100%): Harmful in contact with skin [Warning Acute toxicity, dermal] |
|---|---|
| 規制情報 | Chemical: [1,1'-Biphenyl]-4,4'-diamine, 3,3'-dichloro-3,3-Dichlorobenzidine: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.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.) |
| その他の安全情報 | IMAP assessments - [1,1'-Biphenyl]-4,4'-diamine, 3,3'-dichloro-: Environment tier I assessment |
| 輸送ラベル（DOT） | Poison |
| 火災危険 | Combustible. (NTP, 1992)Combustible. Gives off irritating or toxic fumes (or gases) in a fire. |
| 健康有害性 | Excerpt from NIOSH Pocket Guide for 3,3'-Dichlorobenzidine (and its salts): |
| 有害性の概要 | 3,3'-Dichlorobenzidine is a gray-to-purple colored crystalline solid. It changes from a solid to a gas very slowly. 3,3'-Dichlorobenzidine salt is the major form in actual use. It is a stable, off-white colored crystalline solid that does not evaporate. Neither 3,3'-dichlorobenzidine nor its salt are found naturally in the environment. They are manufactured for pigments for printing inks, textiles, plastics and enamels, paint, leather, and rubber.3,3'-Dichlorobenzidine was used in the past in the production of dyes and pigmentsit is no longer used to manufacture dyes in the United States. No information is available on the acute (short-term), reproductive or developmental effects of 3,3'-dichlorobenzidine in humans. Chronic (long-term) exposure may result in effects on the gastrointestinal, respiratory, and central nervous system (CNS) in humans. A human study detected a possible association between benzidine-based azodyes (including 3,3'-dichlorobenzidine). Animal studies, via the oral route, have reported an increased incidence of tumors at a variety of sites. EPA has classified 3,3'-dichlorobenzidine as a Group B2, probable human carcinogen.Liver injury occurs in animals in subchronic feeding studies. [ACGIH] A skin, eye, and respiratory tract irritant[ICSC] See 3,3'-Dichlorobenzidine dihydrochloride. See Benzidine. |
| 反応性グループ | Aryl Halides |
| EC 分類 | Symbol: T, NR: 45-21-43-50/53S: 53-45-60-61Note: E |
| Special Reports | USEPAAmbient Water Quality Criteria Doc: Dichlorobenzidine (1980) EPA 440/5-80-040.[USEPAAmbient Water Quality Criteria Doc: Dichlorobenzidine (1980) EPA 440/5-80-040Available from, as of February 25, 2015: http://water.epa.gov/scitech/swguidance/standards/upload/2001_10_12_criteria_ambientwqc_dichlorobenzidine80.pdf]FDA/NCTRAcute Toxicity of Aromatic Amines, 5th Rpt FDA/77-1029 (1979).Metabolism of Azo Dyes to Potentially Carcinogenic Aromatic Amines, Technical Rpt for Exp No 196/NIOSHFDA/224-78-0004 (1979).DHHS/ATSDRToxicological Profile for 3,3'-Dichlorobenzidine (1989) ATSDR/TP-89/09, NTIS PB90-171455[HHS/ ATSDRToxicological Profile for 3,3'-Dichlorobenzidine (December 1998). Available from, as of February 25, 2015: http://www.atsdr.cdc.gov/toxprofiles/index.asp]For more Special Reports (Complete) data for 3,3'-DICHLOROBENZIDINE (7 total), please visit the HSDB record page. |
| RCRA 要件 | U073As stipulated in 40 CFR 261.33, when 3,3'-dichlorobenzidine, 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). |
| OSHA Standards | This section applies to any area in which the 13 carcinogens addressed by this section are manufactured, processed, repackaged, released, handled, or stored, but shall not apply to transshipment in sealed containers, except for the labeling requirements under paragraphs (e)(2), (3) and (4) of this section. 3,3'-Dichlorobenzidine (and its salts) is one of the 13 carcinogens. |
| Reactivity Profile | A halide- and amine-substituted aromatic compound. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides. |
| 消火 | This compound is not very flammable but any fire involving this compound may produce dangerous vapors. You should evacuate the area. All firefighters should wear full-body protective clothing and use self-contained breathing apparatuses. You should extinguish any fires involving this chemical with a dry chemical, carbon dioxide, foam, or halon extinguisher. (NTP, 1992)Use fine water spray, dry powder, carbon dioxide. |
| 応急処置措置 | Fresh air, rest. Seek medical attention if you feel unwell.Remove contaminated clothes. Rinse and then wash skin with water and soap. Seek medical attention if you feel unwell.Rinse with plenty of water (remove contact lenses if easily possible).Rinse mouth. Refer for medical attention . |
| 応急処置 | 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.(General first aid procedures) |
| 安全保管 | Provision to contain effluent from fire extinguishing. Separated from food and feedstuffs. Well closed. Store only in original container. Store in an area without drain or sewer access. |
| 消火手順 | Wear self contained breathing apparatus for fire fighting if necessary.Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. |
| 保管条件 | Stable under recommended storage conditions.PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/ |
| 清掃方法 | Use of sodium hypochlorite bleach solution to decontaminate 3,3'-dichlorobenzidine was partially effective. An aqueous solution of 5% tetrapotassium pyrophosphate and 10% sodium ethyl hexyl sulfate when blended in a jet sprayer effectively removed 3,3'-dichlorobenzidine from a worker area (90-99% reduction). Once removed from the work site and collected in a central location, it was then determined that the diazotization reaction (the addition of sulfate, ice and sodium nitrate occurred to eliminate any detectable dichlorobenzine from the washings.PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/ACCIDENTAL RELEASE MEASURES /Personal precautions, protective equipment and emergency procedures/ Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided.Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal. |
| 非火災時の漏出対応 | SMALL SPILLS AND LEAKAGE: You should dampen the solid spill material with acetone, then 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 adsorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a strong soap and water solution. Do not reenter the contaminate area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. |
| 処分方法 | Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U073, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.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.Incineration (820 °C, 0.5 sec for primary combustion1200 °C, 1.0 sec for secondary combustion). The formation of elemental chlorine can be prevented through injection of steam or methane into the combustion process. Nitrogen oxide may be abated through the use of thermal or catalytic devices. Recommendable method: Incineration. Not recommendable method: Discharge to sewer.Incineration: (1500 °F, 0.5 sec for primary combustion2200 °F, 1.0 sec for secondary combustion). The formation of elemental chlorine can be prevented through injection of steam or methane into the combustion process. Nitrogen oxide may be abated through the use of thermal or catalytic devices.For more Disposal Methods (Complete) data for 3,3'-DICHLOROBENZIDINE (11 total), please visit the HSDB record page. |
| 漏出処分 | Personal protection: complete protective clothing including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Sweep spilled substance into sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. |
| Preventive Measures | Employees working with 3,3'-dichlorobenzidine (or its salts) within an isolated system, such as a "glove box" shall wash their hands and arms upon completion of the assigned task and before engaging in other activities not associated with the isolated system.SRP: Contaminated protective clothing should be segregated in a manner such 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.SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.Employees shall be required to shower after the last exit of the day.For more Preventive Measures (Complete) data for 3,3'-DICHLOROBENZIDINE (23 total), please visit the HSDB record page. |
| Isolation and Evacuation | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: |
| 毒性学的情報 | CDC-ATSDR Toxicological Profile |
| Treatment | Treatment for 3,3'-dichlorobenzidine poisoning is usually supportive. (L124) |
| Cancer Sites | Reproductive[in animals: liver & bladder cancer] |
| 相互作用 | Admin in conjunction with other chem: 9 groups of 22 (& 1 of 96) male Wistar rats were given the following cmpd alone or in sequence for a period of 4 wk per cmpd: Ortho-N-butyl-N-(4-hydroxybutyl)nitrosamine (0.01% in drinking-water), N-(4-(5-nitro-2-furyl)-2-thiazolyl)formamide (0.15% in diet), N-fluorenylacetamide (0.025% in diet), & 3,3'-dichlorobenzidine (0.3% in diet). An untreated control group consisted of 12 rats. The animals were killed when 40 wk old. 3,3'-Dichlorobenzidine when given in sequence with 1 or more of the other cmpd induced histological changes of liver (cystic change of bile ducts & oval cell proliferation) in 44-60% of animals (p< 0.05 when compared with ... /control group/). No change was seen in liver when 3'3-dichlorobenzidine was given alone. Incidence of urinary bladder tumors was not significantly incr when 3,3'-dichlorobenzidine was added to diet.A synergistic role for 3,3'-dichlorobenzidine in the development of bladder cancer has been suggested. This was proposed in a study in which no carcinomas were found in any rats admin one of the following: 0.03% 3,3'-dichlorobenzidine in the diet, 0.001% BBN (N-butyl-N-(hydroxybutyl)nitrosamine) in drinking water, 0.0005% 2-acetylaminofluorene (2-AAF) in the diet, or 0.04% N-[4-(5-nitro-2-furyl)-2-thiazolyl]formamide (FANFT) in the diet for a period of 40 wk ... . However, when BBN plus 3,3'-dichlorobenzidine were fed together at the same dose levels as above, there was a marked incr in the presence of papillary or nodular hyperplasia in the rat bladder, and the appearance of one papilloma. Based on these findings, the authors suggested that 3,3'-dichlorobenzidine had a synergistic effect on the cacinogenicity of BBN. In rats sequentially admin BBN (0.01%), FANFT (0.15%), 2-AAF (0.025%), and 3,3'-dichlorobenzidine (0.03%) for 4 wk each, the incidence of bladder cancer after admin of the 4 chemicals was no different than after admin of the first 3, suggesting no interactive effect of any type for 3,3'-dichlorobenzidine ...DCB, 3,3'-dichlorobenzidine, is used primarily as an intermediate in the manufacture of diarylide yellow or azo red pigments for printing ink, textile, paint, and plastics. It is also used in tattoo inks. In this article, we investigate light-induced toxicity of DCB in both bacteria and human Jurkat T-cells. DCB itself is not toxic or mutagenic to Salmonella typhimurium TA102, but is photomutagenic at concentrations as low as 2 microM and phototoxic at concentrations >100 microM when bacteria are exposed to DCB and light at the same time (1.2 J/cm2 of UVA and 2.1 J/cm2 of visible light). Furthermore, DCB is both photocytotoxic and photogenotoxic to human Jurkat T-cells. Under a light irradiation dose of 2.3 J/cm2 of UVA and 4.2 J/cm2 of visible light, it causes the Jurkat T-cells to become nonviable in a DCB dose-dependent manner and the nonviable cells reaches 60% at DCB concentrations higher than 50 microM. At the same time, DNA fragmentation is observed for cells exposed to both DCB and light, determined by single cell gel electrophoresis (alkaline comet assay). As much as 5% (average) DNA fragmentation was observed when exposed to 200 microM DCB and light irradiation. This suggests that DCB can penetrate the cell membrane and enter the cell. Upon light activation, DCB in the cells can cause various cellular damages, leading to nonviable Jurkat T-cells. It appears, the nonviable cells are not caused solely by fragmentation of cellular DNA, but by other damages such as to proteins and cell membranes, or DNA alkylation. Therefore, persons exposed to DCB through environmental contamination or through tattoo piercing using DCB-containing inks must not only concern about its toxicity without exposing to light, but also its phototoxicity. |
| 標的器官 | Cancer, Dermal (Skin), Hepatic (Liver), Renal (Urinary System or Kidneys)Bladder, liver, lung, skin, gastrointestinal tract |
| 健康影響 | The salt form of 3,3'-dichlorobenzidine may cause respiratory infections, stomach upset, and dermatitis. 3,3'-Dichlorobenzidine is also believed to be a possible carcinogen. (L124) |
| 生態毒性値 | LC50Species: Daphnia magna (Water Flea) age <24 hr neonateConditions: freshwater, renewal, 22.3. (22-22.6 °C), pH 8.43 (8.33-8.61), hardness 170 (163-183) mg/L CaCO3, alkalinity 108 (88-131) mg/L CaCO3, dissolved oxygen 98.4% (94.8-100.8%)Concentration: 1050 ug/L for 48 hr (95% confidence interval: 810-1360 ug/L) /98% purity/Species: Pimephales promelas (Fathead Minnow) age 30 days, length 20 mm, weight 0.103 gConditions: freshwater, flow through, 22 (21.7-22.5) °C, pH 7.24 (6.76-7.54), hardness 51.6 (50.9-51.9) mg/L CaCO3, alkalinity 43 (36-46) mg/L CaCO3, dissolved oxygen 83.1% (73.7-88.5%)Concentration: 2080 ug/L for 96 hr /98% purity/Conditions: freshwater, flow through, 21.5 (20.7-22) °C, pH 6.83 (6.55-7.11), hardness 50.9 (50.1-52.7) mg/L CaCO3, alkalinity 49.6 (46.4-51.2) mg/L CaCO3, dissolved oxygen 81.2% (74.3-85.4%)Concentration: 1770 ug/L for 96 hr (95% confidence interval: 1640-1920 ug/L) /98% purity/Species: Pimephales promelas (Fathead Minnow) age 30 days, length 15 mm, weight 0.053 gConditions: freshwater, static, 22.3 (21.8-22.7) °C, pH 6.67 (6.45-6.77), hardness 49 (47.9-49.9) mg/L CaCO3, alkalinity 49.7 (48.4-51.2) mg/L CaCO3, dissolved oxygen 76.7% (67.3-84%)Concentration: 1050 ug/L for 96 hr (95% confidence interval: 820-1340 ug/L) /98% purity/For more Ecotoxicity Values (Complete) data for 3,3'-DICHLOROBENZIDINE (6 total), please visit the HSDB record page. |
| 環境中動態 | TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 33,720 and 15,885 measured in two soils(2) and a Koc range of 721 to 3,965 measured in a variety of sediment soils(3) indicate that 3,3'-dichlorobenzidine is expected to have low to no mobility in soil(SRC). 3,3'-Dichlorobenzidine is a weak base with pKa values of 3.2 and 1.6(4), indicating that this compound will exist primarily in the neutral form. Aromatic amines like 3,3'-dichlorobenzidine and substituted anilines are known to bind to soils containing a large organic carbon content due to the ability of the aromatic amino group to form covalent bonds with humic and fulvic material in soils(5)these complexes are often irreversibly bound and immobile(5). Volatilization of 3,3'-dichlorobenzidine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.8X10-11 atm-cu m/mole(SRC), developed using a fragment constant estimation method(6). 3,3'-Dichlorobenzidine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.1X10-6 mm Hg(SRC), determined from a fragment constant method(6). A 1% of theoretical BOD using activated sludge in the Japanese MITI test indicates that 3,3'-dichlorobenzidine is not readily biodegradable(7). Biodegradation is expected to occur slowly in soils(SRC) and it has been reported that 3,3'-dichlorobenzidine may last for months in soil(8). When incubated in soil under aerobic conditions, only 2% mineralization occurred in 32 weeks(2)under anaerobic conditions no mineralization occurred in a year(2). 3,3'-Dichlorobenzidine absorbs strongly at wavelengths >290 nm(9) and has been shown to photolyze rapidly in aqueous solution(10)therefore, it may be susceptible to direct photolysis on soil surfaces exposed to sunlight(SRC).[(1) Swann RL et alRes Rev 85: 17-28 (1983) (2) Boyd SA et alEnviron Toxicol Chem 3: 201-8 (1984) (3) Donaldson FP, Nyman MCEnviron Toxicol Chem 24: 1022-28 (2005) (4) Nyman MC et alEnviron Sci Technol 31: 1068-73 (1997) (5) Adrian P et alChemosphere 18: 1599-609 (1989) (6) US EPAEstimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of Mar 21, 2015: http://www.epa.gov/oppt/exposure/pubs/episuitedl.htm (7) NITEChemical Risk Information Platform (CHRIP). Biodegradation and Bioconcentration. Tokyo, Japan: Natl Inst Tech Eval. Available from, as of Mar 22, 2015: http://www.safe.nite.go.jp/english/db.html (8) USEPAHigh Production Volume (HPV) Challenge Program. Test Plan for 3,3-Dichlorobenzidine Dihydrochloride (CAS No. 612-83-9), June 2006. Available from, as of Mar 21, 2015: http://www.epa.gov/chemrtk/pubs/summaries/viewsrch.htm (9) NISTNIST Chemistry WebBook.AQUATIC FATE: Based on a classification scheme(1), Koc values of 33,720 and 15,885 measured in two soils(2) and a Koc range of 721 to 3,965 measured in a variety of sediments(3) indicate that 3,3'-dichlorobenzidine is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 2.8X10-11 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). According to a classification scheme(6), a BCF range of 43-856 measured in fish(7-9), suggest bioconcentration in aquatic organisms is moderate to high. A 1% of theoretical BOD using activated sludge in the Japanese MITI test indicates that 3,3'-dichlorobenzidine is not readily biodegradable(9). 3,3'-Dichlorobenzidine is expected to biodegrade slowly in water. The half-life of 3,3'-dichlorobenzidine in a lake water and sediment slurry was approximately 150 days(2). Half-lives of 4-26 weeks and 16-101 weeks have been estimated for the biodegradation of 3,3'-dichlorobenzidine in surface water and anaerobic groundwater, respectively(11). 3,3'-Dichlorobenzidine has been shown to undergo rapid photolysis in aqueous solution yielding monochlorobenzidine, benzidine and other water insoluble products(12,13). The short half-life of this reaction (approximately 1 minute)(13) suggests that photolysis in sunlit surface waters will be an important environmental fate process(SRC). Hydrolysis is not an important environmental fate process for 3,3'-dichlorobenzidine(14).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 3,3'-dichlorobenzidine, which has an estimated vapor pressure of 4.1X10-6 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 3,3'-dichlorobenzidine 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 10 hours(SRC), calculated from its rate constant of 4.0X10-11 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(2). 3,3'-Dichlorobenzidine absorbs strongly at wavelengths >290 nm(3) and has been shown to photolyze rapidly in aqueous solution(4)therefore, it is expected to be susceptible to direct photolysis by sunlight(SRC). Particulate-phase 3,3'-dichlorobenzidine may be removed from the air by wet and dry deposition(SRC).[(1) Bidleman TFEnviron Sci Technol 22: 361-367 (1988) (2) US EPAEstimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of Mar 21, 2015: http://www.epa.gov/oppt/exposure/pubs/episuitedl.htm (3) NIST |
| 有害作用 | 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. |
| 暴露経路 | The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.inhalation, skin absorption, ingestion, skin and/or eye contactOral (L124)inhalation (L124)dermal (L124) |
| 毒性の概要 | IDENTIFICATION AND USE: 3,3'-Dichlorobenzidine (DCB) is gray to purple, crystalline solid. It is used in the United States primarily in the manufacture of pigments for printing ink, textiles, paper, paint, rubber, and plastics and as a curing agent for isocyanate-containing polymers and solid urethane plastics. HUMAN EXPOSURE AND TOXICITY: Dermal exposure to 3,3'-DCB base has caused dermatitis in dye workers. A significant increase in cancer of the blood cells (mostly leukemia) was found among dye-manufacturing workers exposed only to 3,3'-DCB. DCB is capable of inducing DNA damage and some cellular stress responses in HepG2 cells. It has caused unscheduled DNA synthesis in human fibroblasts. Effective biological monitoring was achieved by a combination of monitoring hemoglobin adducts with spot samplings of urinary DCB excretion. DCB is reasonably anticipated to be a human carcinogen. ANIMAL STUDIES: DCB or its dihydrochloride caused tumors in several species of experimental animals, at several different tissue sites, and by several different routes of exposure. Dietary administration of DCB caused mammary-gland cancer (adenocarcinoma) in rats of both sexes, granulocytic leukemia and Zymbal-gland cancer (carcinoma) in male rats, urinary-bladder cancer (transitional-cell or papillary transitional-cell carcinoma) in hamsters and in female dogs, and liver cancer (hepatocellular carcinoma) in female dogs. Subcutaneous injection of DCB caused skin and mammary-gland tumors in rats. Prenatal exposure to DCB in mice caused lymphoid leukemia, and dietary exposure caused liver cancer (hepatocellular carcinoma) in males. Purified and technical grade DCB had some direct mutagenic activity toward Salmonella typhimurium TA1538, but this was increased over 50-fold by activation. DCB injected ip into mice at low concentration increased, and at high concentration, decreased the sister chromatid exchange frequency in bone marrow cells.3,3’-Dichlorobenzidine's mechanism of toxicity derives mainly from the adduction of DNA by its metabolites. The formation of nitroso derivatives during metabolism, yielding a sulfinic acid amide with hemoglobin in erythrocytes, is suggested to be a mechanism for this adduct formation. 3,3’-Dichlorobenzidine can act on the aryl hydrocarbon receptor to induce the activity of cytochrome p-450 enzymes, which metabolize 3,3’-dichlorobenzidine, along with other polyhalogenated aromatics, into their toxic intermediates. (L124, A89, A90) |
| Signs and Symptoms | Cough. Sore throat.MAY BE ABSORBED!Skin sensitization, dermatitisheadache, dizzinesscaustic burnsfrequent urination, dysuriahematuria (blood in the urine)gastrointestinal upsetupper resp infection[potential occupational carcinogen]The salt form of 3,3'-dichlorobenzidine may cause sore throat, respiratory infections, stomach upset, headache, dizziness, caustic burns, and dermatitis. (L124) |
| 大気基準 | Listed as a hazardous air pollutant (HAP) generally known or suspected to cause serious health problems. The Clean Air Act, as amended in 1990, directs EPA to set standards requiring major sources to sharply reduce routine emissions of toxic pollutants. EPA is required to establish and phase in specific performance based standards for all air emission sources that emit one or more of the listed pollutants. 3,3'Dichlorobenzidine is included on this list. |
| CERCLA 報告数量 | 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 1 lb or 0.454 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). |
| 清浄水法要件 | The levels which may result in incremental increase of cancer risk over the lifetime are estimated at 10-5, 10-6, and 10-7. The corresponding recommended criteria are 0.103 ug/l, 0.010 ug/L, and 0.001 ug/L, respectively.Toxic pollutant designated pursuant to section 307(a)(1) of the Federal Water Pollution Control Act and is subject to effluent limitations. /Dichlorobenzidene/ |
| 州飲料水ガイドライン | (AZ) ARIZONA 0.020 ug/L(FL) FLORIDA 7.5 ug/L(MN) MINNESOTA 0.8 ug/L(NH) NEW HAMPSHIRE 0.021 ug/L |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | DD0550000 |
| 輸送番号（UN） | UN 3077 9/PG 3 |
| 毒性 | Acute oral LD50 for rats as free base or dihydrochloride are 7,070 and 3,820, respectively (Gerade and Gerade, 1974). |
| PRTR法 | 第1種指定化学物質 |
| 税関コード | 29215900 |
| 危険文句（R） | 45-21-43-50/53-52/53-39/23/24/25-23/24/25-11-51/53 |
| 化審法 | 一般化学物質 |
| 安衛法 | 特定化学物質障害予防規則:第1類物質,57,57-2 |
| 危険表示 | T,N,F |
| 安全措置（S） | 53-45-60-61-36/37-16-7 |
| 危険等級 | IRRITANTAcute Tox. 4 DermalAquatic Acute 1Aquatic Chronic 1Carc. 1BSkin Sens. 1 |
| 環境リスク評価 | 3,3'-ジクロロベンジジン(91-94-1) |
| 貯蔵分類 | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
| 有害物質データ | 91-94-1(Hazardous Substances Data) |
用途
用途
有機黄色顔料(ベンジジンエローG?GR、バルカン、ファストエローG,パーネントエローHR等)の中間物
使用
Intermediate in the manufacture of azo dyes and pigments for printing inks, textiles, paints, plastics, and crayons; curing agent for isocyanate-terminated polymers and resins; rubber compounding ingredient; analytical determination of gold; formerly used as chemical intermediate for direct red 61 dye.
一般的な説明
Gray to purple crystalline powder. Insoluble in water. Very toxic. Used in the dye industry, curing agent for isocyanate terminated resins.
製法・合成法
純化方法
Crystallise the benzidine from EtOH, pet ether (m 133o) or *benzene. [Beilstein 13 H 234, 13 I 67, 13 II 106, 13 III 477, 13 IV 384.] CARCINOGEN.