吡啶-(2-偶氮-4)间苯二酚 - CAS号 1141-59-9

物化性质

熔点：

192-202 °C(lit.)
沸点：

355.48°C (rough estimate)
密度：

1.2579 (rough estimate)
溶解度：

可溶于DMSO（少许）、甲醇（少许）
稳定性/保质期：

1. 如果遵照规格使用和储存，则不会分解，未有已知危险反应，避免与氧化物接触。 2. 与金属离子形成水溶性或不溶于水的配合物，多数为红色或红紫色。

计算性质

辛醇/水分配系数(LogP)：

2.3
重原子数：

16
可旋转键数：

2
环数：

2.0
sp3杂化的碳原子比例：

0.0
拓扑面积：

78.1
氢给体数：

2
氢受体数：

5

安全信息

TSCA：

Yes
危险等级：

6.1
危险品标志：

Xi
安全说明：

S26,S36
危险类别码：

R36/37/38
WGK Germany：

3
海关编码：

2933399090
危险品运输编号：

2811
包装等级：

III
危险类别：

6.1
储存条件：

请将贮藏器密封，并将其存放在阴凉、干燥处。同时，确保工作环境有良好的通风或排气设施。

SDS

SDS：7983a31b26c0289b552f631f5d10c197

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Name:	4-(2-Pyridylazo)Resorcinol 99% (Titr.) Material Safety Data Sheet
Synonym:	PAR; 1,3-Benzenediol, 4-(2-Pyridinylazo)-
CAS:	1141-59-9

Section 1 - Chemical Product MSDS Name:4-(2-Pyridylazo)Resorcinol 99% (Titr.) Material Safety Data Sheet
Synonym:PAR; 1,3-Benzenediol, 4-(2-Pyridinylazo)-

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1141-59-9	4-(2-Pyridylazo)Resorcinol	99%	214-528-6

Hazard Symbols: XI
Risk Phrases: 36/37/38

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea.
Inhalation:
Causes respiratory tract irritation.
Chronic:
No information found.

Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
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:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
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:
Treat symptomatically and supportively.

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.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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.

Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation. Wash clothing before reuse.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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 adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 1141-59-9: 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.

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: orange
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 188 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C11H9N3O2
Molecular Weight: 215.21

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1141-59-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-(2-Pyridylazo)Resorcinol - Not listed by ACGIH, IARC, or NTP.

Section 12 - ECOLOGICAL INFORMATION

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

Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 22 Do not breathe dust.
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
WGK (Water Danger/Protection)
CAS# 1141-59-9: No information available.
Canada
CAS# 1141-59-9 is listed on Canada's NDSL List.
CAS# 1141-59-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1141-59-9 is listed on the TSCA inventory.

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途：光度法测定过渡金属（如Bi³⁺、Co²⁺、Fe³⁺、Pd²⁺、Ni²⁺、NbO₄⁺、In³⁺、La³⁺、Tn⁴⁺）的试剂，以及等离子体显色剂。EDTA配合滴定法用于检测Al³⁺、Bi³⁺、Ca³⁺、Cu²⁺、Ga³⁺ 等金属的指示剂；硝酸铅溶液沉淀滴定MoO₄²⁻、PO₄³⁻、WO₄²⁻ 等物质的指示剂。

反应信息

作为反应物：

描述：

吡啶-(2-偶氮-4)间苯二酚在 potassium chloride 作用下，以甲醇、水、乙腈为溶剂，反应 0.18h，生成

参考文献：

名称：

三元复合物形成赋予的具有改善的光物理特性和细胞渗透性的锌光笼

摘要：

光笼络合物可以控制金属离子的可用性，以询问细胞信号通路。我们描述了新的光笼，{双[（2-吡啶基）甲基]氨基}（9-氧代-2-氧杂蒽基）乙酸（XDPAdeCage，1），它利用2-氧杂蒽酮乙酸基团来介导光脱羧反应。XDPAdeCage 以 27% 的量子产率光解，并以 4.6 pM 的亲和力结合 Zn2+，在光解后降低超过 4 个数量级。为了与我们之前通过光脱羧释放 Zn2+ 的方法进行比较，还制备了使用间硝基苄基发色团的类似光笼{双[（2-吡啶基）甲基]氨基}（间硝基苯基）乙酸（DPAdeCage，2）并表征。2-氧杂蒽酮醋酸发色团的优点包括激发红移和在优选的解笼锁波长下具有更高的消光系数。[Zn(XDPAdeCage)]+ 与阴离子配体吡啶硫酮的中性三元复合物具有膜渗透性，这避免了利用侵入性技术引入细胞内 Zn2+ 波动的需要。使用荧光成像，我们已经证实了 Zn2+ 跨膜转运；此外，RT-PCR

DOI：

10.1021/jacs.9b05504
作为产物：

描述：

在硫脲作用下，以 aq. buffer 为溶剂，生成吡啶-(2-偶氮-4)间苯二酚

参考文献：

名称：

一种用于选择性和高灵敏度测定硫脲的新型比色化学传感器：一种分子键盘锁的方法

摘要：

使用 4-(2-pridylazo) 间苯二酚 (PAR) 设计和开发了一种新型简单的可逆比色化学传感器。比色受体 PAR 已成功应用于 Hg 2+离子的测定，然后 PAR-Hg 2+复合物已用于水性缓冲介质中的硫脲 (TU) 测量。该化学传感器在水溶液中存在 Hg 2+时表现出明显的颜色变化，从黄色变为鲜红色。此外，所得的 PAR-Hg 2+复合物通过肉眼检测到 TU，显示水溶液中从 PAR-Hg 2+恢复到 PAR。Hg 2+的检测限高达 3.01 nmol/LTU 为 8.5 nmol/L。实现了使用 PAR 和 Hg 2+的比色测量的操作简单性和成本效益。基于此，设计的方法很好地用于测定工业和环境样品中的分析物。两种化学输入（Hg 2+ , TU）之间的分子转换会导致 IMPLICATION 分子逻辑门，该门已被顺序集成以处理顺序信息处理设备。

DOI：

10.1002/jccs.202000485
作为试剂：

描述：

酚磺乙胺在硝酸、 potassium thioacyanate 、铜、 potassium nitrate 、吡啶-(2-偶氮-4)间苯二酚作用下，以乙醇、水为溶剂，反应 0.33h，以100%的产率得到

参考文献：

名称：

A novel visible spectrophotometric method for the determination of ethamsylate in pharmaceutical preparations and biological samples

摘要：

A highly sensitive visible spectrophotometric method has been developed to determine ethamsylate in this paper, which is based on using Cu(II) as spectroscopic probe reagent. The study indicates that in the presence of SCN- and KNO3, Cu(II) is reduced to Cu(I) by ethamsylate at pH 5.0, and the in situ formed Cu(I) reacts with SCN- to form into the white emulsion CuSCN that could be stayed upon the surface of water. According to the amount of residual Cu(II), the amount of ethamsylate can be indirectly determined. Under the optimal conditions, Beer's law is applicable in the range of 0.2-9.0 mu g/mL (7.60 x 10(-7)-3.42 x 10(-5) mol/L) for aqueous standard solution of ethamsylate with linear correlation coefficient of 0.9998. The detection limit and relative standard deviation are 0.12 mu g/mL and 1.5%, respectively. And the molar absorption coefficient of the indirect determination of ethamsylate is 1.0 x 10(5) L/mol cm. The method is successfully applied to determine ethamsylate in pharmaceutical preparations and biological samples. (C) 2009 Elsevier B.V. All rights reserved.

DOI：

10.1016/j.saa.2009.12.039

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文献信息

Oxidative Release of Copper from Pharmacologic Copper Bis(thiosemicarbazonato) Compounds

作者：John J. Sirois、Lillian Padgitt-Cobb、Marissa A. Gallegos、Joseph S. Beckman、Christopher M. Beaudry、James K. Hurst

DOI：10.1021/acs.inorgchem.8b00853

日期：2018.8.6

2-Pyridylazoresorcinol complexation was used to demonstrate that Cu(II) release by reaction with peroxynitrite species involved rate-limiting homolysis of the peroxy O–O bond to generate secondary oxidizing radicals (NO2•, •OH, and CO3•–). Because the potentials for CuII(btsc) oxidation and reduction are ligand-dependent, varying by as much as 200 mV, it is clearly advantageous in designing therapeutic methodologies

从铜-双-硫代嘧啶铜氮杂铜络合物向细胞内递送治疗性或分析性铜的机制通常涉及内源性还原剂将单电子还原为Cu（I）类似物的机制，从而使金属离子不稳定且与bis--不牢固地配位。硫半脲（btsc）配体。但是，本文所述的电化学和光谱研究表明，Cu II（btsc）和Zn II ATSM（btsc =二乙酰基-双（4-甲基硫代半碳氮杂））复合物的单电子氧化在生理氧化剂范围内发生，导致还存在未被认可的铜释放的氧化途径。H 2 O 2氧化Cu II（btsc）由髓过氧化物酶或辣根过氧化物酶，HOCl和牛磺酸氯胺（它们主要是由MPO催化反应在活化的中性粒细胞中产生的氯化剂）以及过氧化亚硝酸盐类（ONOOH，ONOOCO 2 –）催化的被证明。与还原不同，氧化反应通过不可逆的配体氧化进行，最终释放出Cu（II）。2-吡啶基偶氮间苯二酚络合物用于证明通过与过氧亚硝酸盐类物质反应释放Cu（II）涉及限速过氧O-
Formation of the<i>N</i>,<i>N</i>-Bidentate Chelates of 2-(2-Pyridylazo)phenolic Ligands with Nickel(II) in Nonaqueous Solvents

作者：Yoshihiro Kudo、Noboru Yoshida、Masatoshi Fujimoto

DOI：10.1246/bcsj.59.795

日期：1986.3

N,N-bidentate 1:2 complexes of nickel(II) with various N,N,O-terdentate 2-(2-pyridylazo)phenolic ligands was detected spectrophotometrically in ethyl acetate and was examined with respect to the influences of Bronsted bases, the counter anions in the nickel(II) salts employed, solvent basicity, and the steric requirements around the donor nitrogen atoms in the ligand in the 1:2 complex. It is concluded

在乙酸乙酯中通过分光光度法检测镍 (II) 与各种 N,N,O-三齿 2-(2-吡啶偶氮) 酚配体的 N,N-二齿 1:2 配合物的形成，并检查了布朗斯台德碱、所用镍 (II) 盐中的抗衡阴离子、溶剂碱度以及 1:2 配合物中配体中供体氮原子周围的空间要求。得出的结论是，溶液中 N,N-二齿复合物的稳定性主要取决于 NiX2 和溶剂中抗衡阴离子 X 的碱度。在1-(2-吡啶偶氮)-2-萘酚的情况下，由于萘环的空间位阻高，即使在二恶烷等低碱度的溶剂中也未观察到N,N-二齿络合物的形成.
Charge-transfer interaction of 4-(2-pyridylazo)resorcinol with nitroaromatics: Insights from experimental and theoretical results

作者：Animesh Karmakar、Bula Singh

DOI：10.1016/j.molliq.2017.04.005

日期：2017.6

Molecular charge-transfer (CT) complexation of the donor 4-(2-pyridylazo)resorcinol (1P) with selected nitroaromatic acceptors as like, 2,4-DNP, 3,5-DNSA, 3,5-DNBA, and PA have been studied in methanol at room temperature. Among the selected nitroaromatics we have isolated 1P-3,5-DNSA and 1P-PA complexes and characterized them using FT-IR, 1H NMR studies, and elemental analysis. UV–vis studies revealed

供体4-（2-吡啶基偶氮）间苯二酚（1P）与选定的硝基芳香族受体（如2,4-DNP，3,5-DNSA，3,5-DNBA和PA ）的分子电荷转移（CT）络合物具有在室温下在甲醇中进行了研究。在选定的硝基芳族化合物中，我们分离出1P -3,5-DNSA和1P -PA配合物，并使用FT-IR，1 H NMR研究和元素分析对它们进行了表征。UV-vis研究表明，在1P相互作用下用硝基芳族化合物会产生电荷转移带，其吸收区与供体和受体明显不同。基态的滴定度研究表明存在一个同构点，这也表明分子之间有很强的质子传递平衡。还进行了荧光猝灭研究，以发现Stern-Volmer结合常数（K SV）和猝灭效率。FT-IR和1 H NMR研究表明，络合是由于急性氢键相互作用引起的。理论计算（DFT）还提出了H键加合物的形成。
Phenylmethoxybis(tetrazolium) ion-association complexes with an anionic indium(III) — 4-(2-pyridylazo)resorcinol chelate

作者：Teodora Stefanova、Kiril Gavazov

DOI：10.2478/s11532-012-0149-4

日期：2013.2.1

Abstract
Complex formation and liquid-liquid extraction were studied in systems containing indium(III), 4-(2-pyridylazo)resorcinol (PAR), phenylmethoxybis(tetrazolium) salt (MBT), water and chloroform. The following MBTs, which differ only by the number of -NO2 groups in their cationic parts, were used: 3,3′-(3,3′-dimetoxy-4,4′-biphenylene)bis(2,5-diphenyl-2H-tetrazolium chloride) (Blue Tetrazolium chloride, BT), 3,3′-(3,3′-dimetoxy-4,4′-biphenylene)bis[2-(4-nitrophenyl)-5-phenyl-2H-tetrazolium chloride] (Nitro Blue Tetrazolium chloride, NBT) and 3,3′-(3,3′-dimetoxy-4,4′-biphenylene)bis[2,5-di(4-nitrophenyl)-2H-tetrazolium chloride] (Tetranitro Blue Tetrazolium chloride, TNBT). The composition of the formed ternary complexes was determined, In:PAR:MBT=1:2:2, and the optimum conditions for their extraction found: pH, shaking time, concentration of the reagents and the sequence of their addition. Some key constants were estimated: constants of extraction (Kex), constants of association (β) and constants of distribution (KD). BT appears to be the best MBT for extraction of the In(III)-PAR species, [In3+(OH)3(PAR)2]4−, (Log Kex=10.9, Log β=9.8, Log KD=1.12, R%=92.7%). Several additional characteristics concerning its application as extraction-spectrophotometric reagent were calculated: limit of detection (LOD = 0.12 µg cm−3), limit of quantification (LOD = 0.40 µg cm−3) and Sandell’s sensitivity (SS =1.58 ng cm−2); Beer’s law is obeyed for In(III) concentrations up to 3.2 µg mL−1 with a molar absorptivity coefficient of 7.3×104 L mol−1 cm−1 at λmax=515 nm.

摘要：研究了含铟(III)、4-(2-吡啶偶氮)邻苯二酚（PAR）、苯甲氧基双(四唑)盐（MBT）、水和氯仿的体系中的复合物形成和液液萃取。使用了以下仅在它们阳离子部分的-NO2基团数量上有所不同的MBT：3,3′-(3,3′-二甲氧基-4,4′-联苯)双(2,5-二苯基-2H-四唑氯化物)（蓝四唑氯化物，BT）、3,3′-(3,3′-二甲氧基-4,4′-联苯)双[2-(4-硝基苯基)-5-苯基-2H-四唑氯化物]（硝基蓝四唑氯化物，NBT）和3,3′-(3,3′-二甲氧基-4,4′-联苯)双[2,5-二(4-硝基苯基)-2H-四唑氯化物]（四硝基蓝四唑氯化物，TNBT）。确定了形成的三元复合物的组成，In:PAR:MBT=1:2:2，并找到了其萃取的最佳条件：pH值、摇动时间、试剂浓度以及它们添加的顺序。估计了一些关键常数：萃取常数（Kex）、结合常数（β）和分配常数（KD）。BT似乎是最适合提取In(III)-PAR物种，[In3+(OH)3(PAR)2]4−的MBT（Log Kex=10.9，Log β=9.8，Log KD=1.12，R%=92.7%）。计算了几个关于其作为萃取-光度试剂的应用的额外特征：检测限（LOD = 0.12 µg cm−3），定量限（LOD = 0.40 µg cm−3）和桑德尔灵敏度（SS =1.58 ng cm−2）；在λmax=515 nm处，对In(III)浓度达到3.2 µg mL−1的情况下，符合比尔定律，摩尔吸光系数为7.3×104 L mol−1 cm−1。
Synthesis and characterization of copper(I) coordination compounds with (1-(2-pyridylazo)-2-naphthol) and (4-(2-pyridylazo)resorcinol)

作者：M. Płotek、R. Starosta、W. Nitek、U.K. Komarnicka、G. Stochel、A. Kyzioł

DOI：10.1016/j.poly.2013.11.004

日期：2014.1

cuprous complexes with 1-(2-pyridylazo)-2-naphthol (PAN) or 4-(2-pyridylazo)resorcinol (PAR) and triphenylphosphines, [Cu(PAN)(PPh3)2]BF4 (1) and [Cu(PAR)(PPh3)2]BF4 (2), are described in this work. The structures of both compounds were characterized by NMR and UV–Vis spectroscopies, mass spectrometry, IR-ATR measurements and DFT calculations. The single crystal diffraction of both complexes confirmed

与1-（2-吡啶基偶氮）-2-萘酚（PAN）或4-（2-吡啶基偶氮）间苯二酚（PAR）和三苯基膦，[Cu（PAN）（PPh 3）2 ] BF 4（1）和[Cu（PAR）（PPh 3）2 ] BF 4（2），在此工作中进行了介绍。两种化合物的结构均通过NMR和UV-Vis光谱，质谱，IR-ATR测量和DFT计算来表征。两种配合物的单晶衍射证实，铜中心周围的配位多面体是扭曲的四面体。有趣的是，PAR和PAN配体在合成的配合物中不是平面的。配体仅通过两个氮原子与中心铜（I）离子配位：一个来自吡啶，一个来自偶氮基。来自羟基的氧原子不与铜形成键，而是参与强分子内氢键，该氢键稳定配体的构象。值得注意的是，这些键具有不同的特征。在复杂2我们观察到典型的O–H⋯N氢键，而在复杂的1中发生质子转移，导致O⋯H–N键形成。DFT数据证实了在X射线结构中观察到的H键的不同特征。

吡啶-(2-偶氮-4)间苯二酚 | 1141-59-9

物质功能分类

分子结构分类

物化性质

计算性质

安全信息

SDS

制备方法与用途

反应信息

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