2,4-二硝基苯酯 | 4232-27-3

• 物质功能分类: 化学试剂 - 有机试剂 - 硝基化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 中文名称: 2,4-二硝基苯酯
• 中文别名: 2,4-二硝基乙酸苯酯
• 英文名称: 2,4-dinitrophenyl acetate
• 英文别名: (2,4-dinitrophenyl) acetate
• CAS: 4232-27-3
• 化学式: C₈H₆N₂O₆
• mdl: MFCD00041876
• 分子量: 226.145
• InChiKey: CDMLJWCAUSWULM-UHFFFAOYSA-N

物化性质

• 熔点：
  69 °C
• 沸点：
  367.74°C (rough estimate)
• 密度：
  1.6136 (rough estimate)
• 保留指数：
  1513

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 海关编码：
  2915390090

SDS

Name:	2 4-Dinitrophenyl Acetate Material Safety Data Sheet
Synonym:	None
CAS:	4232-27-3

Section 1 - Chemical Product MSDS Name:2 4-Dinitrophenyl Acetate Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
4232-27-3	Phenol, 2,4-dinitro-, acetate (ester)	100	224-189-6

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation. The toxicological properties of this material have not been fully investigated.
Skin:
May cause skin irritation. The toxicological properties of this material have not been fully investigated.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid immediately.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 4232-27-3: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 71.00 - 73.00 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: N/A
Explosion Limits, upper: N/A
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C8H6N2O6
Molecular Weight: 226.15

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, nitrogen.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 4232-27-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Phenol, 2,4-dinitro-, acetate (ester) - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 4232-27-3: No information available.
Canada
CAS# 4232-27-3 is listed on Canada's NDSL List.
CAS# 4232-27-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 4232-27-3 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2,4-二硝基苯酯 在 HEPES buffer 作用下， 生成 2,4-二硝基酚
  参考文献：
  名称：

  一种用于酯水解的自组装纳米纤维催化剂

  摘要：

  基于超分子体系的催化粒子已在催化领域取得显着进步。在这项工作中，合成了组氨酸功能化的自组装肽两亲物 (PAs)，以形成具有内部有序性的自组装高纵横比纳米纤维，可以呈现能够酯水解的咪唑基团。通过透射电子显微镜和圆二色性研究了构成催化颗粒的分子的自组装。用组氨酸残基设计反应位点以催化 2,4-二硝基苯乙酸酯 (DNPA) 的水解。通过紫外-可见光谱和 Michaelis-Menten 酶动力学模型在纳米纤维存在下观察到 DNPA 的酶水解。

  DOI：

  10.1021/ja075044n
• 作为产物：
  描述：

  2,4-二硝基酚 、 乙酰氯 在 吡啶 作用下， 以 乙醚 为溶剂， 反应 12.0h， 以55%的产率得到2,4-二硝基苯酯
  参考文献：
  名称：

  Investigations on substituent and solvent effects on solvolysis reactions Part IX. The influence of polar substituents on the imidazole catalyzed hydrolysis of 2,4-dinitrophenyl acetates in water

  摘要：

  咪唑催化水解极性取代的2,4-二硝基苯乙酸酯的反应在不同温度下已被研究。观察到的速率与咪唑在羧基碳原子上的双分子亲核加成相一致，随后在水中快速水解N-乙酰咪唑。酯分子酸部分中极性取代基对水解反应的影响可以通过电荷间的偶极-偶极相互作用来描述，正如极性取代乙酸乙酯的中性水解一样。

  DOI：

  10.1039/a901004a

文献信息

• Catalysis and inhibition of ester hydrolysis in the presence of resorcinarene hosts functionalized with dimethylamino groups
  作者：Giorgio Cevasco、Sergio Thea、Daniele Vigo、Andrew Williams、Flora Zaman

  DOI：10.1002/poc.1101

  日期：2006.10

  Complexation and catalysis of two calixresorcinarene (RES) derivatives with nucleophilic N,N-dimethylamino functions attached to their upper rims in the hydrolysis of carboxylate and sulfonate esters of 4-nitrophenol and 2,4-dinitrophenol have been investigated. Rate constants obey the complexation equation:

  在4-硝基苯酚和2,4-二硝基苯酚的羧酸酯和磺酸酯的水解过程中，研究了两种杯形异戊二烯（RES）衍生物的亲核N，N-二甲基氨基官能团的络合和催化作用。速率常数服从复杂方程：
• Ruthenium(III) chloride catalyzed acylation of alcohols, phenols, thiols, and amines
  作者：Surya Kanta De

  DOI：10.1016/j.tetlet.2004.02.071

  日期：2004.3

  Ruthenium(III) chloride catalyzes the acylation of a variety of phenols, alcohols, thiols, and amines under mild conditions. Some of the major advantages of this method are high yields, short reaction times, ease of operation, and compatibility with other protecting groups.

  氯化钌（III）在温和的条件下催化各种酚，醇，硫醇和胺的酰化反应。该方法的一些主要优点是产率高，反应时间短，易于操作以及与其他保护基的相容性。
• Metal ion promoted transesterifications of carboxylate esters. A structure/activity study of the efficacy of Zn2+ and La3+ to catalyze the methanolysis of some aryl and aliphatic esters
  作者：Alexei A. Neverov、N. E. Sunderland、R. Stan Brown

  DOI：10.1039/b414763d

  日期：——

  The methanolysis of various aryl and aliphatic carboxylate esters promoted by methoxide, 1,5,9-triazacyclododecane : Zn2+(-OCH3) and La3+(-OCH3), were studied and the derived rate constants (kOCH3, kcat3:Zn(OCH3) and kcatLa(OCH3)) correlated in various ways. The metal ion catalyzed reactions are very much faster than the background reactions in some cases reaching up to 7 x 10(6)-fold acceleration

  研究了甲醇，1,5,9-三氮杂环十二烷：Zn2 +（-OCH3）和La3 +（-OCH3）促进的各种芳基和脂族羧酸酯的甲醇分解，并得出了速率常数（kOCH3，kcat3：Zn（OCH3）和kcatLa（OCH3））以各种方式相关。当存在浓度为5 mmol dm（-3）时，金属离子催化的反应比背景反应快得多，在某些情况下可达到7 x 10（6）倍的加速。两种金属的数据均显示出与离去基团的pKa呈非线性布朗斯台德相关性，并根据随着pKa增加到大于约14.7的值而从金属配位四面体中间体的形成到分解的速率限制步骤的变化进行了分析。 。对数kOCH3反应对vs的曲线图。每个金属离子的log kcat值表示对芳基酯的敏感性较低，而对脂族酯的敏感性较高。提出了观察的机械原理。
• Reactions of aryl acetates with secondary alicyclic amines in ethanol/water mixtures: Effect of the solvent composition on the kinetics and mechanism
  作者：Enrique A. Castro、Daniela Millan、Raul Aguayo、Paola R. Campodónico、José G. Santos

  DOI：10.1002/kin.20598

  日期：2011.12

  We report a kinetic study on the reactions of secondary alicyclic amines toward 4‐nitrophenyl, 2,4‐dinitrophenyl, and 2,4,6‐trinitrophenyl acetates (1, 2, and 3) in ethanol/water mixtures of different compositions. It is found that (i) the intermediate in the reaction of 1 is stabilized in a mixture of 90 vol% ethanol; (ii) for the reaction of 2, the mechanism is stepwise in water but concerted in

  我们报告了在不同组成的乙醇/水混合物中仲脂环族胺对4-硝基苯基，2,4-二硝基苯基和2,4,6-三硝基苯基乙酸酯（1、2和3）的反应的动力学研究。发现（i）在1的反应中的中间体在90体积％的乙醇的混合物中稳定；（ii）对于2的反应，其机理是在水中逐步进行的，但在混合物中是一致的；（iii）对于3的反应，该机理在整个组成范围内是一致的；（ⅳ）的效果 NO 2胜过溶剂作用；（v）可以排除反应核心中的优先溶剂化。©2011 Wiley Periodicals，Inc.国际化学杂志Kinet 43：687–693，2011
• The E1cb route for ester hydrolysis; volumes of activation as an additional criterion of mechanism
  作者：Neil S. Isaacs、Tariq S. Najem

  DOI：10.1039/p29880000557

  日期：——

  of esters which possess an acidic proton at the α or vinylogous position can, in principle, hydrolyse by the E1cb route via a ketenoid intermediate. To the kinetic evidence for such a mechanism in the hydrolyses of 4-hydroxybenzoates, malonates, acetoacetates and fluorenecarboxylates is now added the further criterion of volumes of activation. Values of ΔV‡ for reactions proceeding by the E1cb route

  原则上，在α或乙烯基位置具有酸性质子的酯的水解可以通过酮类中间体通过E 1cb途径进行水解。对于这种在4-羟基苯甲酸酯，丙二酸酯，乙酰乙酸酯和芴羧酸酯水解中的机理的动力学证据，现在增加了活化体积的进一步标准。Δ的值V ‡为反应由出发Ë 1CB路线是正和对比度与由更通常与水解相关的负值乙AC 2机构。

表征谱图