디아니시딘
3,3'-다이메톡시벤지딘 · 디p-아미노디메톡시디페닐 · 디메톡시벤지딘 · 다이아니시딘베이스 · 디아니시딘 · 3,3'-다이메톡시벤지딘(오쏘-디아니시딘) · 3,3'-다이메톡시벤지딘(오쏘-디아니시딘)및그염류 · 3,3'-디메톡시-[1,1-비페닐]-4,4'-디아민

식별자 및 물리적 특성
| CAS No. | 119-90-4 |
|---|---|
| 분자식 | C14H16N2O2 |
| 평균 분자량 | 244.29 g/mol |
| 단동위원소 질량 | 244.12117775 g/mol |
| SMILES | COc1cc(-c2ccc(N)c(OC)c2)ccc1N |
| InChIKey | JRBJSXQPQWSCCF-UHFFFAOYSA-N |
| PubChem CID | 8411 |
| ChEMBL | CHEMBL398363 |
| ChEBI | CHEBI:82321 |
| EC No. | 204-355-4 |
| DTXSID | DTXSID3025091 |
| 현지명 | 디아니시딘 |
화학 및 물리적 성질
| XLogP | 2.2 |
|---|---|
| 극성 표면적 | 70.5 |
| 수소 결합 공여자 수 | 2 |
| 수소 결합 수용자 수 | 4 |
| 회전 가능 결합 수 | 3 |
| 무거운 원자 수 | 18 |
| 형식 전하 | 0 |
| 복잡도 | 236 |
| 물질 분류 | Hazardous Air Pollutants (HAPs)Carcinogens |
| Polymers | Nitrogen Compounds -> Amines, Polyaromatic |
| pH | WEAK BASE |
| LogP(분배 계수) | log Kow = 1.81 |
| Color/Form | LEAFLETS OR NEEDLES FROM WATERColorless crystals that turn a violet color on standing. |
| 용해도 | less than 0.1 mg/mL at 68 °F (NTP, 1992)Sol in alc, benzene, etherSol in chloroform, acetonePROBABLY SOL IN MOST ORG SOLVENTS AND LIPIDSIn water, 60 mg/l @ 25 °CSolubility in water, g/100ml at 25 °C: 0.006H2O: 약간 용해됨 |
| 인화점 | 403 °F (NTP, 1992)206 °C206 °C (403 °F) (closed cup)206 °C c.c. |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Decomposition | When heated to decomp it emits toxic fumes of /nitrogen oxides/. |
| 녹는점 | 279 to 280 °F (NTP, 1992)137 °C137.5 °C279 °F137-138 °C(lit.) |
| 증기 밀도 | 8.5 (NTP, 1992) - Heavier than airwill sink (Relative to Air)8.43 (air= 1) |
| 증기압 | negligible |
| 끓는 점 | 387.21°C (rough estimate) |
| 밀도 | 1.1079 (rough estimate) |
| 굴절률 | 1.6000 (estimate) |
| 저장 조건 | Store at RT. |
| pKa(산도 계수) | 4.71±0.10(Predicted) |
| 물리적 상태 | 결정성 분말 |
| 색상 | 핑크~베이지 브라운 |
| 용해도 | 알코올, 벤젠, 에테르, 클로로포름, 아세톤, 대부분의 유기 용매 및 지질에 용해됩니다. 물에 약간 용해됩니다. |
| Merck | 14,2991 |
| BRN | 1879884 |
| 헨리 상수 | 2.1×105 mol/(m3Pa) at 25℃, HSDB (2015) |
| InChI | 1S/C14H16N2O2/c1-17-13-7-9(3-5-11(13)15)10-4-6-12(16)14(8-10)18-2/h3-8H,15-16H2,1-2H3 |
| InChIKey | JRBJSXQPQWSCCF-UHFFFAOYSA-N |
| SMILES | COc1cc(ccc1N)-c2ccc(N)c(OC)c2 |
| NIST | Benzidine, 3,3'-dimethoxy-(119-90-4) |
| EPA | 3,3'-Dimethoxybenzidine (119-90-4) |
화학적 성질
o-Dianisidine, crystallizes dimorphically, rarely in needles, with mp 133°C , often in flakes with mp 137-138°C . It forms colorless crystals, but commercial products have a tinge of violet. It is sparingly soluble in water but soluble in alcohol, ether, and benzene. One gram of ethyl acetate dissolves 0.285 g of o-dianisidine at 73°C . The pure compound is stable upon exposure to air, but commercial products turn violet. o-Dianisidine is resistant to water but sensitive to oxidizing agents.
안전 및 규제
| GHS 분류 | DangerH302: Harmful if swallowed [Warning Acute toxicity, oral]P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral] |
|---|---|
| 규제 정보 | Chemical: [1,1'-Biphenyl]-4,4'-diamine, 3,3'-dimethoxy-Hazard Traits - CarcinogenicityThe 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 - Benzidine congeners: Human health tier II assessment |
| 운송 라벨(DOT) | Poison |
| 화재 위험 | This chemical is combustible. (NTP, 1992)Combustible. Gives off irritating or toxic fumes (or gases) in a fire. |
| 화재 가능성 | Combustible when exposed to heat or flame. |
| 건강 유해성 | Excerpt from NIOSH Pocket Guide for o-Dianisidine: |
| 유해성 요약 | 3,3'-Dimethoxybenzidine is used as an intermediate in the production of dyes and pigments. No information is available on the acute (short-term), chronic (long-term), reproductive, developmental, or carcinogenic effects of 3,3'-dimethoxybenzidine in humans. Animal studies have reported effects on the liver, kidneys, spleen, and bladder, and endocrine effects, gastritis, intestinal hemorrhage, and weight loss from chronic oral exposure. Increased incidences of tumors in several organs have been reported in rats orally exposed to 3,3'-dimethoxybenzidine or its salt. EPA has classified 3,3'-dimethoxybenzidine as a Group B2, probable human carcinogen.Causes liver injury and tumors in experimental animals[HSDB] No published epidemiology studies on dye workers and cancerCurrently, dye production in closed systems with low risk to workers[NTP] Classified by NIOSH as a carcinogen--reduce exposure to lowest feasible concentration[NIOSH] Symptoms: Irritation skin[CAMEO] |
| 반응성 그룹 | Ethers |
| EC 분류 | Symbol: T |
용도
용도
o-Dianisidine is a starting material for the production of disazo dyes and pigments. Like benzidine and o-tolidine, o-dianisidine forms colors with numerous oxidizing agents, e.g., copper, cobalt, and gold ions. o-Dianisidine is quantitatively determined by titration with nitrite using potassium iodide and starch paper as the indicator. o-Dianisidine can be detected in the urine using potassium 1,2-naphthoquinone4-sulfonate after extraction. A rapid and easy method is based on the color formed with cyanogen bromide. Its detection limit is 0.05 mg/kg. The free o-dianisidine base and the dihydrochloride are marketed in moist forms with a 10-30% water content.
일반 설명
Colorless crystals or a light brown powder. Turns violet on standing. Carcinogen.
제조 및 합성 방법
제조 방법
2-Nitroanisole is reduced (H2-catalyst or iron-formic acid) to o-anisidine or (benzidine-type reaction) to o-dianisidine [119-90-4], both of which are important as dye intermediates.