4-氯噻吩[2,3-D]嘧啶 | 14080-59-2

• 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-氯噻吩[2,3-D]嘧啶
• 中文别名: 4-氯-二噻酚并[2,3-D]嘧啶；4-氯噻吩并[2,3-D]嘧啶；4-氯噻吩[2,3-d]嘧啶
• 英文名称: 4-chlorothieno[2,3-d]pyrimidine
• 英文别名: 4-chlorothiophene[2,3-d]pyrimidine；4-Chlor-thieno<2,3-d>pyrimidin
• CAS: 14080-59-2
• 化学式: C₆H₃ClN₂S
• mdl: MFCD01312373
• 分子量: 170.622
• InChiKey: NZCRUBBNZGVREM-UHFFFAOYSA-N

物化性质

• 熔点：
  109-113°C
• 沸点：
  285.7±20.0 °C(Predicted)
• 密度：
  1.531±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于二氯甲烷、二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S45
• 危险类别码：
  R25,R36
• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302+H312+H332,H315,H319,H335
• 储存条件：
  2-8℃

SDS

Name:	4-Chlorothieno[2 3-d]pyrimidine Material Safety Data Sheet
Synonym:	None Known
CAS:	14080-59-2

Section 1 - Chemical Product MSDS Name:4-Chlorothieno[2 3-d]pyrimidine Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
14080-59-2	4-Chlorothieno[2,3-d]pyrimidine	100	unlisted

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. May be harmful if absorbed through the skin.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
No information found.

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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 not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
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:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Avoid generating dusty conditions. Provide ventilation.

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

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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 ventilation to keep airborne concentrations low.
Exposure Limits CAS# 14080-59-2: 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:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: pale yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 104.4-106.5 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C6H3N2ClS
Molecular Weight: 170.623

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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:
Dust generation.
Incompatibilities with Other Materials:
Oxidizing agents, alcohols, amines, bases.
Hazardous Decomposition Products:
Hydrogen chloride, carbon monoxide, oxides of nitrogen, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 14080-59-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Chlorothieno[2,3-d]pyrimidine - Not listed by ACGIH, IARC, or NTP.

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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 6 Keep under nitrogen.
S 22 Do not breathe dust.
S 24/25 Avoid contact with skin and eyes.
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# 14080-59-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 14080-59-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 14080-59-2 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：

  4-氯噻吩[2,3-D]嘧啶 在 肼 作用下， 反应 2.0h， 生成 s-Triazolo<1,2-c>thieno<3,2-e>pyrimidin
  参考文献：
  名称：

  Robba,M. et al., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1968, vol. 266, p. 128 - 130

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 2-formylaminothiophene-3-carboxylate 在 三氯氧磷 作用下， 反应 21.5h， 生成 4-氯噻吩[2,3-D]嘧啶
  参考文献：
  名称：

  微波辅助合成2-氨基噻吩-3-羧酸衍生物，3 H-噻吩并[2,3 - d ]嘧啶-4-酮和4-氯噻吩并[2,3 - d ]嘧啶

  摘要：

  两分钟的微波辐射允许合成几种2-氨基噻吩-3-羧酸衍生物。还报道了它们在微波辐射下有效转化为噻吩并[2,3 - d ]嘧啶-4-酮和相应的4-氯衍生物。

  DOI：

  10.1016/j.tetlet.2007.05.136

文献信息

• [EN] PYRROLOTRIAZINONE DERIVATIVES AS PI3K INHIBITORS<br/>[FR] DÉRIVÉS DE PYRROLOTRIAZINONE EN TANT QU'INHIBITEURS DES PI3K
  申请人：ALMIRALL SA

  公开号：WO2014060432A1

  公开（公告）日：2014-04-24

  New pyrrolotriazinone derivatives having the chemical structure of formula (I), are disclosed; as well as process for their preparation, pharmaceutical compositions comprising them and their use in therapy as inhibitors of Phosphoinositide 3-Kinases (PI3Ks)

  新的吡咯三唑酮衍生物具有化学结构式（I），公开；以及它们的制备方法，包括它们的药物组合物和它们作为磷脂酰肌醇3-激酶（PI3Ks）抑制剂在治疗中的应用。
• [EN] COMPOUNDS MODULATING PROTEIN RECRUITMENT AND/OR DEGRADATION<br/>[FR] COMPOSÉS MODULANT LE RECRUTEMENT ET/OU LA DÉGRADATION DE PROTÉINES
  申请人：ORIONIS BIOSCIENCES INC

  公开号：WO2021126973A1

  公开（公告）日：2021-06-24

  The invention provides cereblon binders for the degradation of proteins by the ubiquitin proteasome pathway for therapeutic applications.

  这项发明提供了用于通过泛素蛋白酶体途径降解蛋白质的 cereblon 结合物，用于治疗应用。
• A Thieno[2,3-<i>d</i>]pyrimidine Scaffold Is a Novel Negative Allosteric Modulator of the Dopamine D₂ Receptor
  作者：Tim J. Fyfe、Barbara Zarzycka、Herman D. Lim、Barrie Kellam、Shailesh N. Mistry、Vsevolod Katrich、Peter J. Scammells、J. Robert Lane、Ben Capuano

  DOI：10.1021/acs.jmedchem.7b01565

  日期：2019.1.10

  Recently, a novel negative allosteric modulator (NAM) of the D2-like dopamine receptors 1 was identified through virtual ligand screening. This ligand comprises a thieno[2,3-d]pyrimidine scaffold that does not feature in known dopaminergic ligands. Herein, we provide pharmacological validation of an allosteric mode of action for 1, revealing that it is a NAM of dopamine efficacy and identify the structural

  最近，通过虚拟配体筛选鉴定了D 2样多巴胺受体1的新型负变构调节剂（NAM）。该配体包含在已知的多巴胺能配体中不具有的噻吩并[2,3- d ]嘧啶骨架。在此，我们提供了针对1的变构作用模式的药理学验证，表明这是多巴胺功效的NAM，并确定了这种变构的结构决定因素。我们发现关键的结构部分对于功能亲和力和负的协同作用很重要，而硫代嘧啶在5和6位的功能化导致类似物具有不同的协同作用谱。连续的化合物迭代产生了在功能亲和力方面表现出10倍改善的类似物，以及与多巴胺亲和力和功效增强的负协同性。此外，我们的研究揭示了一个片段样的核心，该核心保持了较低的μM亲和力和强大的负协同作用，并显着提高了配体效率。
• Unexpected CO bond formation in Suzuki coupling of 4-chlorothieno[2,3-<i>d</i>]pyrimidines
  作者：Enrico Perspicace、Stéphanie Hesse、Gilbert Kirsch、Mehdi Yemloul、Claude Lecomte

  DOI：10.1002/jhet.107

  日期：2009.5

  Palladium-catalyzed Suzuki reactions were performed on 4-chlorothieno[2,3-d]pyrimidines under classical heating conditions and under microwave irradiation. Some unexpected results were obtained during this study as two kinds of compounds were isolated depending on the conditions used. A careful investigation of experimental details has shown that the expected CC bond formation occurred when degassed

  钯催化的Suzuki反应是在4-氯噻吩并[2,3- d ]嘧啶上在经典加热条件下和在微波辐射下进行的。在此研究中，由于根据所用条件分离出两种化合物，因此获得了一些出乎意料的结果。对实验细节的仔细研究表明，当使用脱气溶剂时（在传统加热和微波加热中）都发生了预期的C C键形成，而在使用前未用氩气对溶剂脱气时发生了意外的C O键形成。J.杂环化​​学。，46，459（2009）。
• Cobalt-Catalyzed Preparation of N-Heterocyclic Organozinc Reagents from the Corresponding Heteroaryl Chlorides
  作者：Paul Knochel、Alexander Kremsmair、Simon Graßl、Christoph J. B. Seifert、Edouard Godineau

  DOI：10.1055/a-1534-0624

  日期：2021.11

  Various substituted and unsubstituted N-heteroaryl chlorides have been converted into their corresponding organozinc species using zinc dust in the presence of zinc pivalate and 10% CoCl2 in benzonitrile at 25 °C. The resulting heteroarylzinc reagents were obtained in 43–98% yield within 9–48 h and reacted with a broad range of electrophiles, leading to the functionalized heteroarenes.

  在新戊酸锌和 10% CoCl2 的苄腈溶液中，在 25 °C 下，使用锌粉将各种取代和未取代的 N-杂芳基氯化物转化为相应的有机锌物质。得到的杂芳基锌试剂在 9-48 小时内以 43-98% 的产率获得，并与广泛的亲电子试剂反应，产生功能化的杂芳烃。