4-溴-2-(甲基硫代)噻唑 | 204513-62-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 4-溴-2-(甲基硫代)噻唑
• 中文别名: 2-甲硫基-4-溴噻唑
• 英文名称: 4-bromo-2-(methylsulfanyl)-1,3-thiazole
• 英文别名: 4-Bromo-2-(methylthio)thiazole；4-bromo-2-methylsulfanyl-1,3-thiazole
• CAS: 204513-62-2
• 化学式: C₄H₄BrNS₂
• mdl: MFCD07787376
• 分子量: 210.118
• InChiKey: YGCKEBOZMZSIDW-UHFFFAOYSA-N

物化性质

• 沸点：
  279.3±32.0 °C(Predicted)
• 密度：
  1.81±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  66.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934100090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302,H317,H319

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 4-Bromo-2-(Thiomethyl)Thiazole
: SYX00338
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.

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SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Acute toxicity, Oral (Category 4), H302
Eye irritation (Category 2), H319
Skin sensitisation (Category 1), H317
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Xn Harmful R22
R36
R43
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Warning
Hazard statement(s)
Harmful if swallowed.
May cause an allergic skin reaction.
Causes serious eye irritation.
Precautionary statement(s)
Wear protective gloves.
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
Other hazards
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.

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SECTION 3: Composition/information on ingredients
Substances
Molecular weight : 210,12 g/mol
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
4-Bromo-2-(Thiomethyl)Thiazole
Acute Tox. 4; Eye Irrit. 2; Skin <= 100 %
Sens. 1; H302, H317, H319
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
4-Bromo-2-(Thiomethyl)Thiazole
Xn, R22R36R43 <= 100 %
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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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
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
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
Nature of decomposition products not known.
Advice for firefighters
Wear self-contained breathing apparatus for firefighting 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 vapours, mist or gas. Ensure
adequate ventilation. Avoid breathing dust.
For personal protection see section 8.
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.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Storage class (TRGS 510): Non Combustible Solids
Specific end use(s)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

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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
Face shield and safety glasses 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).
Control of environmental exposure
Do not let product enter drains.

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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 No data available
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- No data available
octanol/water
p) Auto-ignition 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
Stable under recommended storage conditions.
Possibility of hazardous reactions
No data available
Conditions to avoid
No data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
In the event of fire: see section 5

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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 sensitisation
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
No data available
Specific target organ toxicity - repeated exposure
No data available
Aspiration hazard
No data available
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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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
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.
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. 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
For this product a chemical safety assessment was not carried out

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-溴-2-(甲基硫代)噻唑 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 4-bromo-2-(methylsulfonyl)thiazole
  参考文献：
  名称：

  磺酰噻唑的光氧化还原催化氨甲基化

  摘要：

  开发了叔胺的光氧化还原催化脂肪族C(sp 3 )–H噻唑化反应，通过磺酰噻唑的氨甲基化提供具有生物价值的烷基化噻唑。该反应不含金属和氧化剂，底物范围广泛，可耐受脂肪胺和芳香胺。在室温温和条件下类药分子的克级反应和后期功能化中的成功应用证明了该方案的实用性和成本效益。

  DOI：

  10.1039/d4gc00718b
• 作为产物：
  描述：

  2,4-二溴噻唑 、 sodium thiomethoxide 以 乙醇 为溶剂， 反应 6.0h， 以88%的产率得到4-溴-2-(甲基硫代)噻唑
  参考文献：
  名称：

  12,13-氮丙啶基埃坡霉素。甲基酮和杂芳族膦酸酯的三取代烯烃键的立体选择性合成以及有效抗肿瘤剂的设计、合成和生物学评价

  摘要：

  描述了一系列 12,13-氮丙啶埃坡霉素 B 类似物的合成和生物学评价。这些化合物是通过一种实用的通用方法获得的，该方法涉及以 12,13-烯属甲基酮作为起始材料，通过臭氧分解埃坡霉素 B 然后钨诱导的环氧化物部分脱氧获得。氮丙啶结构基序的连接是通过应用 Ess-Kürti-Falck 氮丙啶化来实现的，而杂环侧链则是通过基于立体选择性膦酸酯的烯化作用引入的。为了确保后一种富电子杂环反应的高 (E) 选择性，有必要对古老的 Horner-Wadsworth-Emmons 反应进行前所未有的改进，使用 2-氟乙氧基膦酸酯，可能被证明在有机合成中具有普遍价值。这些研究导致发现了迄今为止报道的一些最有效的埃坡霉素。配备了适应现代药物递送技术的官能团，这些化合物中的一些表现出皮摩尔的效力，使它们成为抗体药物偶联物 (ADC) 的有效载荷，而其中一些化合物显示出令人印象深刻的抗耐药性人类癌细胞的活性，使其成为理想潜在的医疗应用。

  DOI：

  10.1021/jacs.7b02655

文献信息

• [EN] AZIRIDINE CONTAINING EPOTHILONE ANALOGS, METHODS OF SYNTHESIS, METHODS OF TREATMENT, AND DRUG CONJUGATES<br/>[FR] ANALOGUES D'ÉPOTHILONE CONTENANT DE L'AZIRIDINE, PROCÉDÉS DE SYNTHÈSE, MÉTHODES DE TRAITEMENT, ET CONJUGUÉS MÉDICAMENTEUX DE CEUX-CI
  申请人：UNIV RICE WILLIAM M

  公开号：WO2018191394A1

  公开（公告）日：2018-10-18

  In one aspect, the present disclosure provides epothilone analogs of the formula: (I) wherein the variables are as defined herein. In another aspect, the present disclosure also provides methods of preparing the compounds disclosed herein. In another aspect, the present disclosure also provides pharmaceutical compositions and methods of use of the compounds disclosed herein. Additionally, drug conjugates with cell targeting moieties of the compounds are also provided.

  在一个方面，本公开提供了公式为：(I)的紫杉醇类似物，其中变量如本文所定义。在另一个方面，本公开还提供了制备本文所披露化合物的方法。在另一个方面，本公开还提供了药物组合物和使用本文所披露化合物的方法。此外，还提供了具有细胞靶向基团的药物偶联物。
• [EN] ARYLTHIAZOLYL PIPERIDINES AND RELATED COMPOUNDS AS MODULATORS OF SURVIVAL MOTOR NEURON (SMN) PROTEIN PRODUCTION<br/>[FR] ARYLTHIAZOLYL PIPÉRIDINES ET COMPOSÉS ASSOCIÉS COMME MODULATEURS DE LA PRODUCTION DE PROTÉINE DE NEURONE MOTEUR DE SURVIE (SMN)
  申请人：US HEALTH

  公开号：WO2011130515A1

  公开（公告）日：2011-10-20

  Aryl substituted thiazol-2-yl-piperidines and related compounds useful as modulators of survival motor neuron (SMN) protein production are provided herein. Without being bound to any particular theory it is believed the aryl substituted thiazol-2-yl-piperidines and related compounds provided herein act to increase production of the SMN2 form of survival motor neuron protein. These compounds are useful for treating spinal muscular atrophy. Pharmaceutical compositions containing a carrier and one or more of the aryl substituted thiazol-2-yl-piperidine or related compounds described herein are also provided. Methods of treating spinal muscular atrophy are also provided by this disclosure.

  本文提供了取代基为芳基的噻唑-2-基哌啶和相关化合物，可用作调节存活运动神经元（SMN）蛋白产生的调节剂。虽然不受任何特定理论的约束，但人们认为本文提供的取代基为芳基的噻唑-2-基哌啶和相关化合物可增加存活运动神经元蛋白的SMN2形式的产生。这些化合物适用于治疗脊髓性肌萎缩症。本文还提供了含有载体和本文所述的一种或多种取代基为芳基的噻唑-2-基哌啶或相关化合物的药物组合物。本公开还提供了治疗脊髓性肌萎缩症的方法。
• [EN] EPOTHILONE ANALOGS, METHODS OF SYNTHESIS, METHODS OF TREATMENT, AND DRUG CONJUGATES THEREOF<br/>[FR] ANALOGUES D'ÉPOTHILONE, PROCÉDÉS DE SYNTHÈSE, PROCÉDÉS DE TRAITEMENT, ET CONJUGUÉS MÉDICAMENTEUX DE CEUX-CI
  申请人：UNIV RICE WILLIAM M

  公开号：WO2017066606A1

  公开（公告）日：2017-04-20

  In one aspect, the present disclosure provides epothilone analogs of the formula (I) wherein the variables are as defined herein. In another aspect, the present disclosure also provides methods of preparing the compounds disclosed herein. In another aspect, the present disclosure also provides pharmaceutical compositions and methods of use of the compounds disclosed herein. Additionally, drug conjugates with cell targeting moieties of the compounds are also provided.

  在一个方面，本公开提供了公式（I）中变量如本文所定义的紫杉醇类似物。在另一个方面，本公开还提供了制备本文披露的化合物的方法。在另一个方面，本公开还提供了药物组合物和使用本文披露的化合物的方法。此外，还提供了具有细胞靶向基团的药物共轭物。
• Small-molecule anticancer agents kill cancer cells by harnessing reactive oxygen species in an iron-dependent manner
  作者：Sara R. Fedorka、Kevin So、Ayad A. Al-Hamashi、Ibtissam Gad、Ronit Shah、Veronika Kholodovych、Hanan D. Alqahtani、William R. Taylor、L. M. Viranga Tillekeratne

  DOI：10.1039/c7ob03086j

  日期：——

  In the course of generating a library of open-chain epothilones, we discovered a new class of small molecule anticancer agents that has no effect on tubulin but instead kills selected cancer cell lines by harnessing reactive oxygen species in an iron-dependent manner.

  在生成开链环烯菌素类药物库的过程中，我们发现了一类新型的小分子抗癌药物，它对微管蛋白没有影响，而是通过以铁为依赖的方式利用活性氧种类杀死特定的癌细胞系。
• Data-Rich Experimentation Enables Palladium-Catalyzed Couplings of Piperidines and Five-Membered (Hetero)aromatic Electrophiles
  作者：Aaron C. Sather、Theodore A. Martinot

  DOI：10.1021/acs.oprd.9b00233

  日期：2019.8.16

  palladium-catalyzed C–N cross-coupling methodology, high-throughput experimentation was used to identify a catalyst capable of fusing piperidine-based nucleophiles with five-membered (hetero)aromatic bromides. A decomposition pathway for the standard electrophile was found, and a base screen was used to identify conditions that suppress this undesired transformation. Building on this, systematic optimization using

  为了规避钯催化的C–N交叉偶联方法中的电流限制，使用了高通量实验来鉴定能够将基于哌啶的亲核试剂与五元（杂）芳族溴化物融合的催化剂。发现了标准亲电试剂的分解途径，并且使用基础筛选来鉴定抑制该不希望有的转化的条件。在此基础上，使用“实验设计”方法进行系统优化可提供温和的反应条件，然后将其应用于各种偶联伙伴。