2,4-다이나이트로페놀
2,4-다이나이트로페놀 · 2,4-디니트로페놀 · 2.4-디니트로페놀용액 · 알파-디나이트로페놀 · 알파-디니트로페놀 · 디니트로페놀 · 1-하이드록시-2,4-디니트로벤젠 · 1-하이드록시-2,4-다이나이트로벤젠
식별자 및 물리적 특성
| CAS No. | 51-28-5 |
|---|---|
| 분자식 | C6H4N2O5 |
| 평균 분자량 | 184.11 g/mol |
| 단동위원소 질량 | 184.01202123 g/mol |
| SMILES | O=[N+]([O-])c1ccc(O)c([N+](=O)[O-])c1 |
| InChIKey | UFBJCMHMOXMLKC-UHFFFAOYSA-N |
| PubChem CID | 1493 |
| ChEMBL | CHEMBL273386 |
| ChEBI | CHEBI:42017 |
| EC No. | 200-087-7 |
| DTXSID | DTXSID0020523 |
| 현지명 | 2,4-다이나이트로페놀 |
화학 및 물리적 성질
| XLogP | 1.7 |
|---|---|
| 극성 표면적 | 112 |
| 수소 결합 공여자 수 | 1 |
| 수소 결합 수용자 수 | 5 |
| 회전 가능 결합 수 | 0 |
| 무거운 원자 수 | 13 |
| 형식 전하 | 0 |
| 복잡도 | 220 |
| pH | pH range: 2.6 Colorless, 4.4 Yellow |
| LogP(분배 계수) | 1.67log Kow = 1.671.67 (estimated) |
| 냄새 | SWEET, MUSTY ODOR달콤한, 곰팡내 나는 |
| 맛 | BITTER TASTE |
| 밀도 | 1.68 at 68 °F (USCG, 1999) - Denser than waterwill sink1.683 g/cu cm at 24 °CRelative density (water = 1): 1.681.683 @ 24°C1,683 g/cm3 |
| Color/Form | Pale yellow platelets or leaflets from waterYellowish to yellow orthorhombic crystals |
| 용해도 | less than 1 mg/mL at 67.1 °F (NTP, 1992)2790Soluble in ethanol, ethyl ether, benzene, methanolSolubility at 15 °C (g/100 g solution): ethyl acetate 15.55acetone 35.90chloroform 5.39pyridine 20.08carbon tetrachloride 0.423toluene 6.36Soluble in aqueous alkaline solutionsIn water, 5,600 mg/L at 18 °C43,000 mg/L at 100 °C용해도 물에 거의 용해되지 않음에탄올, 벤젠에 용해됨 |
| 끓는 점 | Sublimes (when carefully heated) (NTP, 1992)318.03°C (rough estimate) |
| Decomposition | When heated to decomposition it emits toxic fumes of /nitroxides/.May explosively decompose on shock, friction, or concussion. |
| 녹는점 | 234 to 237 °F (NTP, 1992)115.5114.8 °C112 °C108-112 °C (lit.) |
| 증기 밀도 | 6.35 (NTP, 1992) - Heavier than airwill sink (Relative to Air)6.35 (Air = 1)Relative vapor density (air = 1): 6.366.35 (vs air) |
| 증기압 | 0.00039 [mmHg]3.9X10-4 mm Hg at 20 °C39(x 10-5 mmHg) at 20 °C (Schwarzenbach et al., 1988) |
| 굴절률 | 1.4738 (estimate) |
| 인화점 | 11 °C |
| 저장 조건 | 2-8°C |
| 물리적 상태 | 크리스탈 |
| pKa(산도 계수) | 3.96(at 15℃) |
| 색상 | 연노랑 |
| 용해도 | 0.6g/100mL(18℃) |
| Merck | 14,3280 |
| BRN | 1246142 |
| 헨리 상수 | 5.70 x 10-8(atmm3/mol) at 5 °C (average derived from six field experiments, Lüttke and Levsen, 1997) |
| 안정성 | 안정적인. 타기 쉬운. |
| 주요 응용 | 디스플레이 장치, 기록 재료, 잉크, 페인트, 식품 보존 방법, 유전자 발현 프로파일링 방법, 기생충 질환 치료, 신경 질환, 간질, 암, 케라틴 재료, 신생물, 감염성 질환, 호중구 감소증, 염색체 이상 검출, 위장관 내 세균 |
| InChI | 1S/C6H4N2O5/c9-6-2-1-4(7(10)11)3-5(6)8(12)13/h1-3,9H |
| InChIKey | UFBJCMHMOXMLKC-UHFFFAOYSA-N |
| SMILES | Oc1ccc(cc1[N+]([O-])=O)[N+]([O-])=O |
| NIST | Phenol, 2,4-dinitro-(51-28-5) |
| EPA | 2,4-Dinitrophenol (51-28-5) |
화학적 성질
light yellow crystal powder
안전 및 규제
| GHS 분류 | DangerH300: Fatal if swallowed [Danger Acute toxicity, oral]H311: Toxic in contact with skin [Danger Acute toxicity, dermal]H331: Toxic if inhaled [Danger Acute toxicity, inhalation]H372: Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]H400: Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]P260, P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P319, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement) |
|---|---|
| 규제 정보 | Chemical: Phenol, 2,4-dinitro-Hazard Traits - Hazard Trait UndefinedAuthoritative List - CA TACsCWA 303(c)Report - if used as a fragrance or flavor ingredientStatus: Active Update: 09-03-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/10875Phenol, 2,4-dinitro- (wetted with not less than 15% water by mass): HSNO Approval: HSR001273 Approved with controlsThe 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.) |
| 운송 라벨(DOT) | Flammable Solid Poison |
| 화재 위험 | Combustible. May explode if subjected to heat or flame. POISONOUS GAS IS PRODUCED WHEN HEATED. Vapors are toxic. Can detonate or explode when heated under confinement. (USCG, 1999)· 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.· Corrosives in 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.· Flammable/combustible material.· May be ignited by heat, sparks or flames.· DRIED OUT material may explode if exposed to heat, flame, friction or shock |
용도
용도
2,4-Dinitrophenol (DNP) can be used: As a reactant for catalytic reduction reactions.To activate carboxylic acids by converting them into dinitrophenyl (DNP) esters.To prepare the corresponding ester via acylation reaction using isobutyric anhydride catalyzed by hafnium triflate.As an effective cocatalyst to accelerate the activity and enantioselectivity of primary amine organocatalyst derived from natural primary amino acids for direct asymmetric aldol reaction. As an alternative activator to tetrazoles in the reaction of phosphoroamidites with nucleosides.
일반 설명
Solid yellow crystals. Explosive when dry or with less than 15% water. The primary hazard is from blast of an instantaneous explosion and not flying projectiles and fragments. slightly soluble in water and soluble in ether and solutions of sodium or potassium hydroxide.
제조 및 합성 방법
생산 방법
2,4-Dinitrochlorobenzene is hydrolyzed by heating with 6 % aqueous sodium hydroxide at 95 – 100 ℃ for 4 h. The product 2,4-Dinitrophenol is precipitated by addition of acid, filtered off, and washed to remove acid and also a small quantity of the more soluble 2,6-isomer. The yield is 95 %.