2,5-双(4-吡啶)-1,3,4-噻二唑 | 15311-09-8

• 物质功能分类: 医药中间体 - 杂环化合物 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2,5-双(4-吡啶)-1,3,4-噻二唑
• 中文别名: 2,5-双(4-吡啶基)-1,3,4-噻二唑；2,5-双(4-氮苯基)-1,3,4-噻重氮
• 英文名称: 2,5-bis(4-pyridyl)-1,3,4-thiadiazole
• 英文别名: 2,5-bis(pyrid-4-yl)-1,3,4-thiadiazole；2,5-bis-(4-pyridyl)-1,3,4-thiadiazole；2,5-bis(4-pyridyl)1,3,4-thiadiazole；2,5-di(4-pyridyl)-1,3,4-thiadiazole；1,3,4-thiadiazole-2,5-di-4-pyridyl；bpt；2,5-dipyridin-4-yl-1,3,4-thiadiazole
• CAS: 15311-09-8
• 化学式: C₁₂H₈N₄S
• 分子量: 240.288
• InChiKey: UQDBUNOBHAOPPJ-UHFFFAOYSA-N

物化性质

• 熔点：
  237-244 °C
• 沸点：
  475.9±55.0 °C(Predicted)
• 密度：
  1.3072 (rough estimate)
• 稳定性/保质期：
  遵循规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  79.8
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 危险品标志：
  T
• 危险类别码：
  R36/37/38
• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P362,P403+P233,P501
• 危险性描述：
  H315,H319,H335
• 安全说明：
  S26,S36/37/39
• 储存条件：
  存于阴凉干燥处。

SDS

Name:	2 5-Bis-(4-Pyridyl)-1 3 4-Thiadiazole 95% Material Safety Data Sheet
Synonym:	1,3,4-Thiazole, 2,5-Bis (4-Piridinyl)-; Pyridine, 4,4'-(1,3,4-Thiadiazole-s,5-Diyl)Di-
CAS:	15311-09-8

Section 1 - Chemical Product MSDS Name:2 5-Bis-(4-Pyridyl)-1 3 4-Thiadiazole 95% Material Safety Data Sheet
Synonym:1,3,4-Thiazole, 2,5-Bis (4-Piridinyl)-; Pyridine, 4,4'-(1,3,4-Thiadiazole-s,5-Diyl)Di-

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
15311-09-8	2,5-Bis(4-Pyridyl)-1,3,4-Thiadiazole	95%	239-353-2

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

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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. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

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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 breathing is difficult, give oxygen. Get medical aid. Do NOT use mouth-to-mouth resuscitation. If breathing has ceased apply artificial respiration using oxygen and a suitable mechanical device such as a bag and a mask.
Notes to Physician:
Treat symptomatically and supportively.

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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.
Extinguishing Media:
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:
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. Remove contaminated clothing and wash before reuse. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed.
Avoid ingestion and inhalation. Use with adequate ventilation.
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 adequate general or local exhaust ventilation to keep airborne concentrations below the permissible exposure limits.
Exposure Limits CAS# 15311-09-8: 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: brown
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 239.00 - 240.00 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: C12H8N4S
Molecular Weight: 240.28

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, sulfur oxides (SOx), including sulfur oxide and sulfur dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 15311-09-8: UT8570500 LD50/LC50:
Not available.
Carcinogenicity:
2,5-Bis(4-Pyridyl)-1,3,4-Thiadiazole - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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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: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 15311-09-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 15311-09-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 15311-09-8 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

反应信息

• 作为反应物：
  描述：

  2,5-双(4-吡啶)-1,3,4-噻二唑 以 甲醇 、 水 为溶剂， 生成 [Cu(2,5-bis(4-pyridyl)-1,3,4-thiadiazole)(H2O)(SO4)]
  参考文献：
  名称：

  由角二吡啶基配体和CuII，CdII，CoII盐组装而成的配位聚合物：晶体结构和性质。

  摘要：

  基于连接单元2,5-双（4-吡啶基）-1,3,4-噻二唑（L（1））或2,5-双（3-吡啶基）-1,3的六个新的金属-有机配位网络1,4-恶二唑（L（3））和无机Cu（II），Cd（II）和Co（II）盐已制备，并通过单晶X射线分析对其结构进行了表征。使用L（1）与三种不同的Cu（II）盐Cu（OAc）（2）.H（2）O，Cu（NO（3））（2）.3H（2）O和CuSO（ 4）.5H（2）O，分别是两种不同的一维（1-D）配位聚合物，[[Cu（2）L（1）（mu-OAc）（4）]（CHCl（3））（ 2）]（n）（1）[三斜度，空间群P1，a = 7.416（3）A，b = 8.207（3）A，c = 14.137（5）A，alpha = 100.333（7）度，beta = 105.013（6）度，gamma = 94.547（6）度，Z = 1]和[[CuL（1）（NO（3））（2）]（CHCl（3））（0

  DOI：

  10.1021/ic034999d
• 作为产物：
  描述：

  dithioisonicotinic acid ; potassium-salt 在 一水合肼 作用下， 生成 2,5-双(4-吡啶)-1,3,4-噻二唑
  参考文献：
  名称：

  Koenig et al., Chemische Berichte, 1954, vol. 87, p. 825,834

  摘要：

  DOI：

文献信息

• Discrete half-sandwich Ir, Rh-based organometallic molecular boxes: synthesis, characterization, and their properties
  作者：Ying-Feng Han、Yue-Jian Lin、Guo-Xin Jin

  DOI：10.1039/c1dt10506j

  日期：——

  The treatment of binuclear complexes [Cp*2M2(μ-QA)Cl2] (M = Ir, 2a; M = Rh, 2b) (H2QA = 1,4-dihydroxyanthraquinone) with pyrazine or bifuncational pyridyl-based ligands (4,4′-dipyridine (bpy), E-1,2-bis(4-pyridyl)ethene (bpe), 2,5-bis(4-pyridyl)-1,3,4-oxadiazole (bpo), and 2,5-bis(4-pyridyl)-1,3,4-thiadiazol (bpt)) in the presence of AgOTf (OTf = CF3SO3) in CH3OH, gave the corresponding tetra-nuclear complexes, with a general formula of [Cp*4M4(μ-QA)2(μ-L)2](OTf)4 (M = Ir, 3a–7a; M = Rh, 3b–7b), respectively. The molecular structure of [Cp*4Ir4(μ-QA)2(μ-pyrazine)2](OTf)4 (3a) has been determined by single-crystal X-ray analysis, revealing that the metal centers were connected by pyrazine and bis-bidentate QA2− ligands to construct a rectangular cavity with the dimension of 7.30 × 8.41 × 6.92 Å. Complexes 3a and 3b were found to exhibit selective trapping of halocarbons properties.

  通过在CH3OH中与AgOTf（OTf = CF3SO3）存在的条件下处理二核配合物[Cp*2M2(μ-QA)Cl2]（M = Ir，2a；M = Rh，2b）（H2QA = 1,4-二羟基蒽醌）与吡嗪或基于4,4'双吡啶的双功能配体（4,4'-联吡啶（bpy）、E-1,2-双（4-吡啶基）乙烯（bpe）、2,5-双（4-吡啶基）-1,3,4-噁二唑（bpo）和2,5-双（4-吡啶基）-1,3,4-噻二唑（bpt）），分别得到相应的一般式为[Cp*4M4(μ-QA)2(μ-L)2](OTf)4的四核配合物（M = Ir，3a–7a；M = Rh，3b–7b）。通过单晶X射线分析确定了[Cp*4Ir4(μ-QA)2(μ-吡嗪)2](OTf)4（3a）的分子结构，揭示了金属中心通过吡嗪和双齿QA2−配体连接，构建了一个尺寸为7.30 × 8.41 × 6.92 Å的长方形孔穴。3a和3b配合物被发现具有选择性捕获卤代烃的性质。
• Hydrothermal synthesis of a one-dimensional Ni(II) coordination polymer with H-bonding left- and right-handed helical features
  作者：Gui-Lin Wen、Chao Sun、Lv-Ting Wang、Ying Yao、Xiao-Qing Xu、Ling-Bao Kong、Dong Tian、Mai Xu、Xiao-Yong Lu

  DOI：10.1080/24701556.2018.1500594

  日期：2018.3.4

  One new coordination polymer has been synthesized hydrothermally under the intervention of Ni(II) salts, 4,4′-sulfonyldibenzoate (H2sdba) with neutral linkers 2,5-bis(4-pyridyl)-1,3,4-thiadiazole (bpt), formulated as: [Ni(bpt)(sdba)(H2O)3]n (1). X-ray structural analysis reveals that polymer 1 displays one-dimensional zigzag chain with alternating intersectional terminal sdba units. The interactions

  在具有中性接头2,5-双（4-吡啶基）-1,3,4-噻二唑的Ni（II）盐4,4'-磺酰基二苯甲酸酯（H 2 sdba）的干预下水热合成了一种新的配位聚合物（bpt），公式为：[Ni（bpt）（sdba）（H 2 O）3 ] n（1）。X射线结构分析表明，聚合物1显示具有交替的交叉末端sdba单元的一维之字形链。伪水带与1 D链的相互作用导致3 D超分子网络的形成。有趣的是，介孔骨架1中同时出现了两种类型的氢键合左旋和右旋螺旋。
• SYNTHESIS OF SUBSTITUTED 1,3,4-THIADIAZOLES USING LAWESSON'S REAGENT
  作者：B. Gierczyk、M. Zalas

  DOI：10.1080/00304940509354950

  日期：2005.6

  oxychloride or sulfuric acid have been used in such reactions. Another route for 1,3,4-thiadiazole ring synthesis, is via exchange of the oxygen atom in 1,3,4-oxadiazole to sulfur, using tetraphosphorus decasulfide or thiourea;I2 however in our experience, this method does not work in many cases. Lawesson has described the thionation of 1 ,2-diacylhydrazineswith 2,4bis(4-methoxypheny1)1,2,3,4-dithiadiphosphetane

  含硫化合物具有许多特殊和独特的性质，这使它们继续受到关注。由于其广泛的生物活性谱，1,3,4-噻二唑已被检查为潜在的抗菌剂，“抗病毒？镇痛剂：抗肿瘤剂：抗惊厥药、消炎药～、药物、杀虫剂和杀菌剂。其中一些形成热致液晶并具有有趣的电光特性。6 此外，噻二唑已被用作腐蚀和氧化抑制剂^,^染料或金属离子络合剂~。~ ~ J ~ J 这类化合物最常用的合成方法包括硫酰肼或其他底物与 SCNNCS 部分的环化和脱水。'2,6 通常在此类反应中使用磷酰氯或硫酸。1,3,4-噻二唑环合成的另一种途径是通过将 1,3,4-恶二唑中的氧原子交换为硫，使用十硫化四磷或硫脲；I2 但是根据我们的经验，这种方法在许多情况下不起作用案件。Lawesson 描述了 1 ,2-二酰基肼与 2,4 双(4-甲氧基苯基)1,2,3,4-二噻二膦（劳森试剂）的硫化作用，然后是自发环化和脱氢硫化，这是一种改进的噻二唑环形成方法。
• Rapid synthesis of 2,5-disubtituted 1,3,4-thiadiazoles under microwave irradiation
  作者：Mounim Lebrini、Fouad Bentiss、Michel Lagrenée

  DOI：10.1002/jhet.5570420538

  日期：2005.7

  The one pot, three-components condensation of aromatic aldehydes, hydrazine and sulfur in ethanol under microwave irradiation provided symmetrically 3,5-disubstituted 1,3,4-thiadiazoles in high yields and good purity. This reaction must be conducted under pressure of hydrogen sulfide produced in-situ. The structure of the compounds was confirmed by 1H, 13C NMR, MS and elemental analysis.

  在微波辐射下，一锅三组分的芳香醛，肼和硫在乙醇中的缩合反应可对称地提供3,5-二取代的1,3,4-噻二唑，产率高且纯度高。该反应必须在原位产生的硫化氢的压力下进行。化合物的结构通过1 H，13 C NMR，MS和元素分析确认。
• Rational Design and Control of the Dimensions of Channels in Three‐Dimensional, Porous Metal‐Organic Frameworks Constructed with Predesigned Hexagonal Layers and Pillars
  作者：Cui‐Jin Li、Sheng Hu、Wei Li、Chi‐Keung Lam、Yan‐Zhen Zheng、Ming‐Liang Tong

  DOI：10.1002/ejic.200501121

  日期：2006.5

  New three-dimensional, microporous metal-organic frameworks exhibiting reversible water adsorption, constructed from hexagonal [Co3(imda)2] layers and N,N′-pillars, in which the dimensions of the channels are rationally adjustable by varying the lengths of pillars, have been designed, hydrothermally synthesized, and characterized. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

  新型三维微孔金属有机骨架具有可逆吸水性，由六边形 [Co3(imda)2] 层和 N,N'-柱构成，其中通道的尺寸可以通过改变柱的长度来合理调节，已被设计、水热合成和表征。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)