4-硝基马尿酸 | 2645-07-0

• 物质功能分类: 化学试剂 - 有机试剂 - 芳香酸
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-硝基马尿酸
• 中文别名: 对硝基马尿酸；N-(4-硝基苯甲酰基)甘氨酸
• 英文名称: 4-nitrohippuric acid
• 英文别名: 2-(4-nitrobenzamido)acetic acid；p-nitrobenzoylglycine；(4-nitrobenzoyl)glycine；N-(carboxymethyl)-4-nitrobenzamide；2-[(4-nitrobenzoyl)amino]acetic acid
• CAS: 2645-07-0
• 化学式: C₉H₈N₂O₅
• mdl: MFCD00007349
• 分子量: 224.173
• InChiKey: XCMUCRMMVDSVEL-UHFFFAOYSA-N

物化性质

• 熔点：
  131-133 °C(lit.)
• 沸点：
  365.56°C (rough estimate)
• 密度：
  1.4656 (rough estimate)
• 物理描述：
  4-nitrohippuric acid is a yellow powder. (NTP, 1992)
• 溶解度：
  1 to 5 mg/mL at 72° F (NTP, 1992)
• 稳定性/保质期：
  如果按照规格使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 安全说明：
  S24/25
• WGK Germany：
  3
• 海关编码：
  2924299090
• RTECS号：
  MC0785000
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H317,H319
• 储存条件：
  请将密封于阴凉干燥环境中。

SDS

Name:	4-Nitrohippuric acid 98% Material Safety Data Sheet
Synonym:	N-(4-Nitrobenzoyl)glycin
CAS:	2645-07-0

Section 1 - Chemical Product MSDS Name:4-Nitrohippuric acid 98% Material Safety Data Sheet
Synonym:N-(4-Nitrobenzoyl)glycin

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
2645-07-0	4-Nitrohippuric acid	98.0	220-156-5

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.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. 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.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Get medical aid immediately.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
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.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
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:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels.
Exposure Limits CAS# 2645-07-0: 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: 131 - 133 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C9H8N2O5
Molecular Weight: 224.17

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong bases.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 2645-07-0: MC0785000 LD50/LC50:
Not available.
Carcinogenicity:
4-Nitrohippuric acid - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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Section 12 - ECOLOGICAL INFORMATION
Other No information available.

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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.
WGK (Water Danger/Protection)
CAS# 2645-07-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 2645-07-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 2645-07-0 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

N-(4-硝基苯甲酰)甘氨酸是甘氨酸（HY-Y0966）的一种衍生物。

反应信息

• 作为反应物：
  描述：

  4-硝基马尿酸 在 ammonium hydroxide 、 iron(II) sulfate 作用下， 生成 对氨基马尿酸
  参考文献：
  名称：

  ON THE SEROLOGICAL SPECIFICITY OF PEPTIDES

  摘要：

  带有关于肽的血清学特性研究可能最终有助于理解蛋白质沉淀反应的想法，已经准备了含有氨基苯甲酰化二肽的抗原，即甘氨酰甘氨酸、甘氨酰-d-亮氨酸、d-亮氨酰甘氨酸和d-亮氨酰-d-亮氨酸。这四种抗原在血清学上被发现有所不同，它们的特异性取决于携带游离羧基的末端氨基酸的结构，也在较小程度上取决于第二个氨基酸。这些结果是通过沉淀和抑制试验获得的。与酶特异性观察的类比被讨论。

  DOI：

  10.1084/jem.55.5.781
• 作为产物：
  描述：

  2-<4-Nitrophenyl>-oxazol-5-on 在 hydroxide 作用下， 生成 4-硝基马尿酸
  参考文献：
  名称：

  Structure-reactivity studies on the equilibrium reaction between phenolate ions and 2-aryloxazolin-5-ones: data consistent with a concerted acyl-group-transfer mechanism

  摘要：

  DOI：

  10.1021/ja00542a028

文献信息

• Synthesis and spectral properties of new ethylene glycol bridged oxazol-5-ones: High Stokes' shift fluorophores sensitive to solvent polarity
  作者：Gulsiye Ozturk Urut、Dilek Bayramin、Serap Alp

  DOI：10.1016/j.molliq.2017.09.092

  日期：2017.12

  384–418 nm and emission maxima at 430–607 nm, respectively. The solvatofluorism study of 3a and 3c revealed that their emission wavelengths are very sensitive to solvent polarity and are red shifted in polar solvents. 3a and 3c fluorophores exhibited high Stokes shift values between 4158 and 7921 cm− 1.

  合成了一组新的并结合有醛单元的乙二醇链的恶唑-5-酮荧光团，并进行了结构表征。根据对恶唑-5-酮部分的取代，可以区分出两对化合物：一对带有甲苯基单元，另一对带有硝基苯基单元。这些对之间的差异是乙二醇链的长度。在七种不同极性的不同溶剂中对新的恶唑-5-酮衍生物的吸收和发射性质进行了评估，它们分别在384-418 nm和430-607 nm处显示出强烈的吸收最大值。3a和3c的溶剂氟研究结果表明，它们的发射波长对溶剂极性非常敏感，在极性溶剂中会发生红移。3a和3c荧光团在4158和7921 cm -1之间显示出较高的斯托克斯位移值。
• Structural effects of N-aromatic acyl-amino acid conjugates on their deconjugation in the cecal contents of rats: implication in design of a colon-specific prodrug with controlled conversion rate at the target site
  作者：Hyesik Kong、Hyunjeong Kim、Heejeong Do、Yonghyun Lee、Sungchae Hong、Jeong-Hyun Yoon、Yunjin Jung、Young Mi Kim

  DOI：10.1002/bdd.763

  日期：2011.9

  N-aromatic acyl-amino acid conjugates was examined in the cecal contents. On incubation of conjugates with glycine, D or/and L forms of alanine or phenylalanine in the cecal contents, the conjugates with D amino acids were not hydrolysed. The other conjugates are susceptible to the hydrolysis, the rates of which decreased as the size of the substituent on the 2-position of the amino acids increased. The conjugates

  N-芳族酰基-氨基酸缀合物具有靶向结肠的特性，这意味着此类缀合物是稳定的并且在到达大肠之前不被吸收，在大肠中它们被微生物转化（水解）为具有治疗活性的母体药物。为了研究N-芳族酰基-氨基酸缀合物对大肠去结合的结构影响，在盲肠内容物中检查了各种N-芳族酰基-氨基酸缀合物的水解。在将共轭物与甘氨酸，盲肠内容物的D或/和L形式的丙氨酸或苯丙氨酸一起孵育后，具有D氨基酸的共轭物不被水解。其他缀合物易于水解，其速率随着氨基酸2-位上取代基大小的增加而降低。具有甘氨酸和牛磺酸的烷基类似物（2-4个碳原子）的结合物具有抗水解性，而牛磺酸和甘氨酸的结合物则被有效地水解。N-芳族酰基-甘氨酸缀合物的水解通过芳族酰基部分上的吸电子基团的对位取代而得到增强，反之亦然。尽管邻位上的甲基，甲氧基或氯基阻止了水解，但位上的羟基却加速了水解。我们的数据可能为设计大肠内转化率受控的结肠特异性前药提供有用的信息。N-芳族酰基
• PREPARATION OF<i>N</i>-ACYL DERIVATIVES OF AMINO ACIDS FROM ACYL CHLORIDES AND AMINO ACIDS IN THE PRESENCE OF CATIONIC SURFACTANTS. A VARIATION OF THE SCHOTTEN-BAUMANN METHOD OF BENZOYLATION OF AMINO ACIDS
  作者：Branko S. Jursic、Donna Neumann

  DOI：10.1081/scc-100000582

  日期：2001.1

  A very efficient method for the preparation of N-acylamino acids from the corresponding acyl chloride and amino acid is described. Amino acids, potassium carbonate, acyl chloride, and a catalytic amount of cationic surfactants were mixed in tetrahydrofuran and refluxed without ever obtaining a clear reaction mixture. After hot filtration, the product was isolated from the hot tetrahydrofuran solution

  描述了一种从相应的酰氯和氨基酸制备 N-酰基氨基酸的非常有效的方法。将氨基酸、碳酸钾、酰氯和催化量的阳离子表面活性剂混合在四氢呋喃中并回流，但从未获得澄清的反应混合物。热过滤后，产物以非常高或几乎定量的产率从热的四氢呋喃溶液中分离出来。
• The reduction of aromatic nitro groups on solid supports using sodium hydrosulfite (Na2S2O4)
  作者：Randall A Scheuerman、David Tumelty

  DOI：10.1016/s0040-4039(00)00959-x

  日期：2000.8

  An improved method for reducing aromatic nitro compounds on solid-phase supports using sodium hydrosulfite is presented. Conditions have been optimized to enable the use of this reagent for reductions on both polyethyleneglycol-polystyrene (PEG) resins and traditional polystyrene (PS) resins.

  提出了一种使用亚硫酸氢钠还原固相载体上芳族硝基化合物的改进方法。已对条件进行了优化，以使该试剂可用于还原聚乙二醇-聚苯乙烯（PEG）树脂和传统聚苯乙烯（PS）树脂。
• Acid-catalyzed cyclocondensation of nitriles. Part IV. Synthesis and spasmolytic activity of 1-substituted 3-aminoisoquinolines and their derivatives
  作者：A. V. Sereda、G. B. Lapa、I. E. Sukhov、L. F. Belova、S. Ya. Sokolov、A. I. Miroshnikov、O. N. Tolkachev

  DOI：10.1007/bf02464152

  日期：1997.4

  Biologically active compounds with an isoquinoline nucleus are widely used in medicine (papaverine, No-Spa, salsoline, etc.). Earlier, we have developed a simple and efficient method for the synthesis of 3-aminoisoquinolines and the corresponding 3-iminocarbonylamino derivatives [ I, 2]. The purpose of this work was to obtain acyl derivatives of 3-aminoisoquinolines, substituted at the amino group

  具有异喹啉核的生物活性化合物广泛用于医药（罂粟碱、No-Spa、沙索碱等）。早些时候，我们开发了一种简单有效的方法来合成 3-氨基异喹啉和相应的 3-亚氨基羰基氨基衍生物 [I, 2]。这项工作的目的是获得氨基取代的 3-氨基异喹啉的酰基衍生物，并研究 3-氨基异喹啉及其衍生物的解痉活性。最初的 3-氨基异喹啉 (IIIa-IIIc) 是使用先前描述的方法合成的 [1, 2]。该程序的第一步在于芳基乙腈的酸催化环缩合反应。这是一个三阶段过程（参见方案 1），包括中间体 Nimidoylnitrilium 离子 (II) 和 3-氨基异喹啉 (III) 的形成；反应机理在别处[1]中详细讨论过。尽管最终 3-氨基异喹啉基氨基酰亚胺 IV 的产率相当低 (50 - 72%)，但产品始终包含未反应的初始腈和 3-氨基异喹啉（二聚产物）[1, 2]。下面我们将证明增加第一阶段的持续时间会导致更完全的试剂消耗。色谱估计表明，反应物料中