4-氯-6-甲基噻吩[2,3-D]嘧啶 | 106691-21-8

• 物质功能分类: 医药中间体 - 杂环化合物 - 嘧啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 中文名称: 4-氯-6-甲基噻吩[2,3-D]嘧啶
• 中文别名: 4-氯-6-甲基噻吩并[2,3-d]嘧啶
• 英文名称: 4-chloro-6-methylthieno<2,3-d>pyrimidine
• 英文别名: 6-Methyl-4-chlorothieno<2,3-d>pyrimidine；4-chloro-6-methylthieno[2,3-d]-pyrimidine；4-chloro-6-methylthieno[2,3-d]pyrimidine；4-chloro-6-methyl-thieno[2,3-d]pyrimidine
• CAS: 106691-21-8
• 化学式: C₇H₅ClN₂S
• mdl: MFCD03030440
• 分子量: 184.649
• InChiKey: NNEBWENPZIGRQK-UHFFFAOYSA-N

物化性质

• 熔点：
  88-91℃ (sublm)
• 沸点：
  301.3±37.0 °C(Predicted)
• 密度：
  1.445±0.06 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 安全说明：
  S26
• 危险类别码：
  R36
• WGK Germany：
  3
• 海关编码：
  2934999090
• 危险标志：
  GHS07
• 危险性描述：
  H302,H319
• 危险性防范说明：
  P305 + P351 + P338
• 储存条件：
  室温和干燥环境

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 4-Chloro-6-Methylthieno[2,3-D]Pyrimidine
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.
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
Acute toxicity, Oral (Category 4), H302
Eye irritation (Category 2), H319
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
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)
H302 Harmful if swallowed.
H319 Causes serious eye irritation.
Precautionary statement(s)
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 : 184,65 g/mol
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
4-Chloro-6-Methylthieno[2,3-D]Pyrimidine
Acute Tox. 4; Eye Irrit. 2; <= 100 %
H302, H319
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
4-Chloro-6-Methylthieno[2,3-D]Pyrimidine
Xn, R22R36 <= 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
No data available
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
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).
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
Other decomposition products - No data available
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.
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: Other information
Full text of H-Statements referred to under sections 2 and 3.
Acute Tox. Acute toxicity
Eye Irrit. Eye irritation
H302 Harmful if swallowed.
H319 Causes serious eye irritation.
Full text of R-phrases referred to under sections 2 and 3
Xn Harmful
R22 Harmful if swallowed.
R36 Irritating to eyes.
Further information
Copyright 2014 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：

  4-氯-6-甲基噻吩[2,3-D]嘧啶 在 溶剂黄146 、 锌 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以72%的产率得到6-甲基噻吩并[2,3-d]嘧啶
  参考文献：
  名称：

  噻吩并[3,2- c ]吡啶，噻吩并[2,3- d ]哒嗪和噻吩并[2,3- d ]嘧啶环体系衍生的reissert化合物的制备

  摘要：

  在呋喃[3,2- c ]吡啶，噻吩并[3,2- c ]吡啶，噻吩并[2,3- d哒嗪和噻吩并呋喃]中对比了三丁基氰化锡，三甲基甲硅烷基氰和氰化钾在Reissert反应中的使用。[2，3- d ]嘧啶环系统。

  DOI：

  10.1002/jhet.5570230247
• 作为产物：
  描述：

  2-氨基-5-甲基-噻吩-3-甲酸乙酯 在 五氯化磷 、 三氯氧磷 作用下， 反应 24.0h， 生成 4-氯-6-甲基噻吩[2,3-D]嘧啶
  参考文献：
  名称：

  基于4-氨基噻吩并[2,3-d]嘧啶的新型蛋白激酶CK2抑制剂的设计与合成

  摘要：

  我们先前研究工作的扩展已导致在4-氨基噻吩并[2,3-d]嘧啶衍生物中鉴定出许多新的与ATP竞争的CK2抑制剂。在研究过程中获得的活性最高的化合物是3-（5-对甲苯基-噻吩并[2,3-d]嘧啶-4-基氨基）苯甲酸5e（NHTP23，IC 50  = 0.01μM）， 3-（5-苯基-噻吩并[2,3-d]嘧啶-4-基氨基）-苯甲酸，5g（NHTP25，IC 50  = 0.065μM）和3-（6-甲基-5-苯基-噻吩并[2 ，3-d]嘧啶-4-基氨基）-苯甲酸，5n（NHTP33，IC 50 = 0.008μM）。研究了测试的4-氨基噻吩并[2,3-d]嘧啶衍生物的结构-活性关系，并提出了它们与CK2 ATP受体位点的结合方式。讨论了分子内氢键对化合物结构的负面影响。

  DOI：

  10.1016/j.ejmech.2016.03.004

文献信息

• Discovery and Optimization of Pyrrolopyrimidine Inhibitors of Interleukin-1 Receptor Associated Kinase 4 (IRAK4) for the Treatment of Mutant MYD88^L265P Diffuse Large B-Cell Lymphoma
  作者：James S. Scott、Sébastien L. Degorce、Rana Anjum、Janet Culshaw、Robert D. M. Davies、Nichola L. Davies、Keith S. Dillman、James E. Dowling、Lisa Drew、Andrew D. Ferguson、Sam D. Groombridge、Christopher T. Halsall、Julian A. Hudson、Scott Lamont、Nicola A. Lindsay、Stacey K. Marden、Michele F. Mayo、J. Elizabeth Pease、David R. Perkins、Jennifer H. Pink、Graeme R. Robb、Alan Rosen、Minhui Shen、Claire McWhirter、Dedong Wu

  DOI：10.1021/acs.jmedchem.7b01290

  日期：2017.12.28

  optimization of a series of pyrrolopyrimidine inhibitors of interleukin-1 receptor associated kinase 4 (IRAK4) using X-ray crystal structures and structure based design to identify and optimize our scaffold. Compound 28 demonstrated a favorable physicochemical and kinase selectivity profile and was identified as a promising in vivo tool with which to explore the role of IRAK4 inhibition in the treatment of mutant

  本文中，我们报告了使用X射线晶体结构和基于结构的设计来鉴定和优化我们的支架，优化了一系列白介素1受体相关激酶4（IRAK4）的吡咯并嘧啶抑制剂。化合物28表现出良好的理化和激酶选择性，并被认为是一种有前途的体内工具，可利用该工具探索IRAK4抑制作用在突变MYD88 L265P弥漫性大B细胞淋巴瘤（DLBCL）的治疗中的作用。化合物28已显示在体​​外高浓度下具有抑制NF-κB活化和ABC亚型ABC亚型生长的能力，但与低浓度下的BTK抑制剂联用则显示出更大的作用。在体内，化合物28和依鲁替尼的组合在ABC-DLBCL小鼠模型中导致肿瘤消退。
• [EN] ECTONUCLEOTIDE PYROPHOSPHATASE/PHOSPHODIESTERASE 1 (ENPP1) MODULATORS AND USES THEREOF<br/>[FR] MODULATEURS D'ECTONUCLÉOTIDES PYROPHOSPHATASES/PHOSPHODIESTÉRASES 1 (ENPP1) ET LEURS UTILISATIONS
  申请人：SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INST

  公开号：WO2021133915A1

  公开（公告）日：2021-07-01

  Provided herein are small molecule modulators of ectonucleotide pyrophosphatase/phosphodiesterase 1 (ENPP1), compositions comprising the compounds, and methods of using the compounds and compositions comprising the compounds.

  本文提供了外胞核苷酸焦磷酸酶/磷酸二酯酶1（ENPP1）的小分子调节剂，包括这些化合物的组合物，以及使用这些化合物和包含这些化合物的组合物的方法。
• Synthesis of 3-Azabicyclo[3.2.0]heptane-Derived Building Blocks via [3+2] Cycloaddition
  作者：Anton A. Homon、Oleksandr V. Hryshchuk、Serhii Trofymchuk、Oleg Michurin、Yuliya Kuchkovska、Dmytro S. Radchenko、Oleksandr O. Grygorenko

  DOI：10.1002/ejoc.201800972

  日期：2018.11.1

  Synthesis of 3‐azabicyclo[3.2.0]heptane‐derived building blocks via [3+2]cycloaddition of cyclobutene‐1‐carboxylate and azomethine ylide is described. It is shown that the title bicyclic scaffold is a three‐dimensional template which is well‐compatible with lead‐oriented parallel synthesis.

  描述了通过环丁烯-1-羧酸酯和甲亚胺叶立德的[3 + 2]环加成反应合成3-氮杂双环[3.2.0]庚烷的结构单元。结果表明标题双环支架是一个三维模板，与基于铅的平行合成很好地兼容。
• [EN] QUINOLINE AND QUINOXALINE DERIVATIVES AS KINASE INHIBITORS<br/>[FR] DÉRIVÉS DE QUINOLÉINE ET DE QUINOXALINE EN TANT QU'INHIBITEURS DE KINASE
  申请人：UCB PHARMA SA

  公开号：WO2011058110A1

  公开（公告）日：2011-05-19

  A series of quinoline and quinoxaline derivatives, substituted by a fused bicyclic pyridine or pyrimidine moiety attached via an alkylene chain optionally linked to a heteroatom, being selective inhibitors of P13 kinase enzymes, are accordingly of benefit in medicine, for example in the treatment of inflammatory, autoimmune, cardiovascular, neurodegenerative, metabolic, oncological, nociceptive or ophthalmic conditions.

  一系列喹啉和喹喔啉衍生物，通过一个融合的双环吡啶或嘧啶基团取代，并通过一个可选择连接到杂原子的烷基链，是选择性P13激酶酶抑制剂，在医学上具有益处，例如在炎症、自身免疫、心血管、神经退行性、代谢、肿瘤、疼痛或眼科疾病的治疗中。
• AMINO ACID COMPOUNDS AND METHODS OF USE
  申请人：Pliant Therapeutics, Inc.

  公开号：US20190276449A1

  公开（公告）日：2019-09-12

  The invention relates to compounds of formula (A) and formula (I): or a salt thereof, wherein R 1 , R 2 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , q and p are as described herein. Compounds of formula (A), formula (I), and pharmaceutical compositions thereof are αvβ6 integrin inhibitors that are useful for treating fibrosis such as idiopathic pulmonary fibrosis (IPF) and nonspecific interstitial pneumonia (NSIP).

  该发明涉及以下化合物的公式(A)和公式(I)：或其盐，其中R1、R2、R10、R11、R12、R13、R14、R15、R16、q和p如本文所述。公式(A)、公式(I)的化合物及其药物组合物是αvβ6整合素抑制剂，可用于治疗纤维化疾病，如特发性肺纤维化（IPF）和非特异性间质性肺炎（NSIP）。