5-对甲基苯基-2-氨基-1,3,4-噻二唑 | 26907-54-0

• 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: 5-对甲基苯基-2-氨基-1,3,4-噻二唑
• 中文别名: 2-氨基-5-(4-甲氧苯基)-1,3,4-噻二唑；2-氨基-5-(4-甲基苯基)-1,3,4-噻二唑
• 英文名称: 2-amino-5-(4-methylphenyl)-1,3,4-thiadiazole
• 英文别名: 5-(4-methylphenyl)-1,3,4-thiadiazol-2-amine；5-(p-tolyl)-1,3,4-thiadiazol-2-amine；2-amino-5-(p-tolyl)-1,3,4-thiadiazole；2-Amino-5-p-tolyl-1,3,4-thiadiazol
• CAS: 26907-54-0
• 化学式: C₉H₉N₃S
• mdl: MFCD00469688
• 分子量: 191.257
• InChiKey: ZLDPCNCAFSBFCX-UHFFFAOYSA-N

物化性质

• 熔点：
  218-222 °C
• 沸点：
  364.9±35.0 °C(Predicted)
• 密度：
  1.281±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  80
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26
• 危险类别码：
  R22,R36/37/38
• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存储条件：2-8°C，避光，并保存在惰性气体环境中。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 2-Amino-5-(4-methylphenyl)-1,3,4-thiadiazole
CAS-No. : 26907-54-0
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Acute toxicity, Oral (Category 4)
Skin irritation (Category 2)
Eye irritation (Category 2)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Harmful if swallowed. Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H302 Harmful if swallowed.
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R22 Harmful if swallowed.
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : 2-Amino-5-(p-tolyl)-1,3,4-thiadiazole
5-(p-Tolyl)-1,3,4-thiadiazol-2-amine
Formula : C9H9N3S
Molecular Weight : 191,25 g/mol
Component Concentration
2-Amino-5-(4-methylphenyl)-1,3,4-thiadiazole
CAS-No. 26907-54-0 -

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Section 4. FIRST AID MEASURES
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx), Sulphur oxides
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested
and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
Use respirators and components tested and approved under appropriate government standards
such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 218 - 222 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- log Pow: 2,17
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. Causes respiratory tract irritation.
Ingestion Harmful if swallowed.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes Causes serious eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed
professional waste disposal service to dispose of this material. Dissolve or mix the material with a
combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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Section 15. REGULATORY INFORMATION
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
no data available

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Section 16. OTHER INFORMATION
Further information
Copyright 2012 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

反应信息

• 作为反应物：
  描述：

  5-对甲基苯基-2-氨基-1,3,4-噻二唑 在 sodium hydroxide 、 对甲苯磺酰叠氮 、 苄基三甲基氯化铵 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以72.4%的产率得到2-叠氮-5-(4-甲基苯基)-1,3,4-噻二唑
  参考文献：
  名称：

  [1,3,4]噻二唑[3,2-a] -1,2,3-三唑并[4,5-d]嘧啶-9（3H）-one衍生物的合成及抗过敏活性。一世。

  摘要：

  一系列6取代的[1,3,4]噻二唑[3,2-a] -1,2,3-三唑并[4,5-d]嘧啶-9（3H）-一衍生物4a-z为通过下列连续反应由5-取代的1,3,4-噻二唑-2-胺5合成：用双（2,4,6-三氯苯基）丙二酸酯进行嘧啶闭环，硝化，氯化，胺化，氢化和重氮化。通过交替合成4来证实4的结构，该合成涉及5-取代的2-叠氮基-1,3,4-噻二唑13与氰基乙酸乙酯的反应，然后进行Dimroth重排和闭环。评估了产品的抗过敏活性（抗-被动性腹膜过敏，抗-被动性皮肤过敏和抗慢反应物质）。

  DOI：

  10.1248/cpb.40.357
• 作为产物：
  描述：

  4-methylbenzaldehyde thiosemicarbazone 在 溴 作用下， 以 溶剂黄146 为溶剂， 生成 5-对甲基苯基-2-氨基-1,3,4-噻二唑
  参考文献：
  名称：

  设计，合成和分子对接的新型取代的基于靛红的吡唑啉和噻二唑啉作为抗肿瘤药物的结构对接

  摘要：

  癌症，被认为是世界上最严重的疾病，导致820万人死亡，并且到2030年这一比率可能翻一番。我们在此报告了一系列新的3-（2-（p-取代）-2-（（5-苯基- -1,3,4-噻二唑-2-基）亚氨基）-2-（对-取代的）亚乙基）二氢吲哚-2-酮（15 - 19）和5-取代的5'-取代的苯基-2'，4'二氢螺[二氢吲哚-3,3'-吡唑] -2-酮衍生物（20 - 24）作为有效的抗癌剂。评估了这些化合物对60个癌细胞系的国家癌症研究所的体外抗肿瘤活性。在所有合成的化合物中，两种化合物15和16对GI 50均显示出显着的抗肿瘤活性非小细胞肺癌的（MG-MID）值分别为0.65和0.72 µM。为了深入了解与表皮生长因子受体激酶酶的结合方式，对这些化合物进行了进一步的对接研究。

  DOI：

  10.1007/s00044-017-1781-5

文献信息

• Synthesis and CNS depressant activity of some novel 3-[5-substituted 1,3,4-thiadiazole-2-yl]-2-styryl quinazoline-4(3H)-ones
  作者：Varsha Jatav、Pradeep Mishra、Sushil Kashaw、J.P. Stables

  DOI：10.1016/j.ejmech.2007.02.004

  日期：2008.1

  anticonvulsant activity in one or more test models. All except 4e and 4f exhibited significant sedative-hypnotic activity via actophotometer screen. CNS depressant activity screened with the help of the forced swim pool method resulted into some potent compounds. From the experimental observation it can be concluded that synthesized compounds exhibited relatively better sedative-hypnotic and CNS depressant activities

  合成了一系列新型的3- [5-取代苯基-1,3,4-噻二唑-2-基] -2-苯乙烯基喹唑啉-4（3H）-并评估其抗惊厥，镇静催眠和中枢神经系统抑制活性。在以30、100和300mg / kg体重腹腔注射小鼠后，在最大电击诱发癫痫发作（MES）和皮下戊四氮（scPTZ）诱发的癫痫发作模型中检查了2-苯乙烯基喹唑啉-4（3H）-衍生物。老鼠。使用转子法评估神经毒性。在18种化合物中，只有4a，4d，4e，4j和4k在一个或多个测试模型中显示出抗惊厥活性。通过光度计屏幕，除4e和4f外，所有其他药物均显示出明显的镇静催眠活性。借助于强制游泳池法筛选的中枢神经系统抑制剂活性产生了一些有效的化合物。
• Synthesis, antibacterial and antifungal activity of some novel 3-[5-(4-substituted phenyl) 1,3,4-thiadiazole-2-yl]-2-styryl quinazoline-4(3H)-ones
  作者：Varsha Jatav、Sushil Kashaw、Pradeep Mishra

  DOI：10.1007/s00044-007-9047-2

  日期：2008.6

  3-[5-substituted phenyl-1,3,4-thiadiazole-2-yl]-2-styryl quinazoline-4(3H)-ones were synthesized and evaluated for antibacterial activity against pathogenic strains of Staphylococcus aureus (MTCC no. 96), Bacillus subtilis (MTCC no. 619), Pseudomonas aeruginosa (MTCC no. 424) and Escherichia coli (MTCC no. 40) and antifungal activity against Aspergillus niger, Candida albicans and Fusarium oxysporum

  合成了一系列新型的3- [5-取代的苯基-1,3,4-噻二唑-2-基] -2-苯乙烯基喹唑啉-4（3H）-，并评估了其对 金黄色葡萄球菌 致病菌株的抗菌活性 （ MTCC编号96）， 枯草芽孢杆菌 （MTCC编号619）， 铜绿假单胞菌 （MTCC编号424）和 大肠杆菌 （MTCC编号40）以及对 黑曲霉，白色念珠菌 和 尖孢镰刀菌的 抗真菌活性 。采用杯板法测定化合物的最小抑菌浓度（MIC）值。一些化合物表现出与诺氟沙星相当的活性。本报告揭示了合成的2-苯乙烯基-喹唑啉-4（3H）-一具有比抗真菌活性更好的抗菌作用。
• Synthesis and evaluation of the trypanocidal activity of a series of 1,3,4-thiadiazoles derivatives of R-(+)-limonene benzaldehyde-thiosemicarbazones
  作者：Solange C. Martins、Vânia C. Desoti、Danielle Lazarin-Bidóia、Fábio Vandresen、Cleuza C. da Silva、Tania Ueda-Nakamura、Sueli de O. Silva、Celso V. Nakamura

  DOI：10.1007/s00044-016-1561-7

  日期：2016.6

  selectivity indexes. The vast majority of the monoterpene derivatives, substituted by R-(+)-limonene, presented better anti-T. cruzi activity than the non-substituted compounds. Regarding the cytotoxic profile, the compounds without the monoterpene R-(+)-limonene were, in general, less toxic. The present findings indicate that the 1,3,4-thiadiazoles derivatives of R-limonene have potential trypanocidal activity

  在这项研究中，我们合成了一系列R -（+）-mon烯苯甲醛-硫代半咔唑酮（2a - k）的1,3,4-噻二唑衍生物。我们还确定了LLCMK 2细胞的细胞毒性以及克氏锥虫，这些合成化合物以及一系列不含单萜R -（+）-柠檬烯（4a的1,3,4-噻二唑– k）。1,3,4-噻二唑化合物显示出显着的锥虫杀灭活性和高选择性指数。被R -（+）-柠檬烯取代的绝大多数单萜衍生物表现出更好的抗T.活性高于非取代化合物。关于细胞毒性特征，通常不含单萜R -（+）-柠檬烯的化合物毒性较小。目前的发现表明，R-柠檬烯的1,3,4-噻二唑衍生物具有潜在的锥虫杀虫活性，因此有必要进行进一步的研究以更好地了解这些物质对克氏锥虫的作用机理。
• PhI-Catalyzed Intramolecular Oxidative Coupling Toward Synthesis of 2-Amino-1,3,4-Thiadizoles
  作者：Yingzhi Han、Yadong Sun、Ablimit Abdukader、Bifu Liu、Duozhi Wang

  DOI：10.1007/s10562-018-2541-y

  日期：2018.11

  derivatives via intramolecular oxidative coupling of thiosemicarbazide, using the in situ generated hypervalent iodine(III) reagents is developed. The protocol can be carried out smoothly and provides a variety of thiadiazole derivatives in moderate to excellent yields.Graphical AbstractA highly efficient method for the synthesis of thiadiazole derivatives via PhI-catalyzed intramolecular oxidative coupling

  摘要 开发了一种利用原位生成的高价碘（III）试剂，通过氨基硫脲的分子内氧化偶联合成噻二唑衍生物的高效方法。该协议可以顺利进行，并以中等至优异的收率提供各种噻二唑衍生物。图形摘要一种高效的合成噻二唑衍生物的方法通过 PhI 催化分子内氧化偶联氨基硫脲。
• Molecular sieves promoted, ultrasound-mediated synthesis, biological evaluation and docking study of 3-(5-substituted-1,3,4-thiadiazol-2-ylimino)indolin-2-ones as a potential anticonvulsant agents
  作者：Anna Pratima G. Nikalje、Sameer I. Shaikh、Firoz A. Kalam Khan、Shoaib Shaikh、Jaiprakash N. Sangshetti

  DOI：10.1007/s00044-015-1458-x

  日期：2015.12

  In this work, the combined use of ultrasonic energy and molecular sieves was investigated for synthesis of 3-(5-substituted-1,3,4-thiadiazol-2-ylimino)indolin-2-one derivatives 5(a–j). The equimolar quantities of 5-substituted-1,3,4-thiadiazol-2-amine and isatin were sonicated in the presence of activated molecular sieves 3 Å at a temperature of 50 °C and at a frequency 20 kHz, and higher yields (73–92 %)

  在这项工作中，研究了超声能量和分子筛的联合使用，以合成3-（5-取代的1,3,4-噻二唑-2-ylimino）吲哚-2-酮衍生物5（a–j）。在活化分子筛3Å的存在下，在50°C的温度和20 kHz的频率下，对等摩尔量的5-取代的1,3,4-噻二唑-2-胺和靛红进行超声处理。与传统方法相比，使用超声波辐照可获得73-92％）和更快的反应时间（43-75分钟）。评估合成化合物在小鼠中的抗惊厥作用（MES和sc-PTZ模型）和行为活性（光度计）。化合物5b，5i和5j在剂量水平为100 mg / kg时，在0.5和4小时内对MES模型具有保护作用，而在相同剂量水平下，化合物5c对sc-PTZ模型具有保护作用。为了利用合成化合物的作用方式，进行了对钠通道受体的对接研究，结果显示了与受体的良好结合相互作用。还分析了合成化合物的ADME性质，并显示出有可能发展为良好的口服药物候选物。