2,4-二甲基噻唑-5-羧酸乙酯 | 7210-77-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2,4-二甲基噻唑-5-羧酸乙酯
• 中文别名: 2,4-二甲基噻唑-5-甲酸乙酯；2，4-二甲基噻唑-5-羧酸乙酯
• 英文名称: ethyl 2,4-dimethyl-1,3-thiazole-5-carboxylate
• 英文别名: ethyl 2,4-dimethylthiazole-5-carboxylate
• CAS: 7210-77-7
• 化学式: C₈H₁₁NO₂S
• mdl: MFCD00052874
• 分子量: 185.247
• InChiKey: BXOIIRQIGYJTTB-UHFFFAOYSA-N

物化性质

• 熔点：
  46-50 °C
• 沸点：
  254.3±20.0 °C(Predicted)
• 密度：
  1.164±0.06 g/cm3(Predicted)
• 闪点：
  >110℃
• 溶解度：
  DMF：30 mg/ml； DMSO：20 mg/ml；乙醇：50 mg/ml；乙醇:PBS (pH 7.2) (1:10): 0.1 mg/ml
• 稳定性/保质期：
  遵照规格使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  67.4
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险类别码：
  R36/37/38
• 海关编码：
  2934100090
• 安全说明：
  S24/25
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  密封于阴凉干燥处。

SDS

Name:	Ethyl 2 4-dimethylthiazole-5-carboxylate Material Safety Data Sheet
Synonym:	None Known
CAS:	7210-77-7

Section 1 - Chemical Product MSDS Name:Ethyl 2 4-dimethylthiazole-5-carboxylate Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
7210-77-7	Ethyl 2,4-dimethylthiazole-5-carboxyla	ca. 98	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. May be harmful if inhaled.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: 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.
Ingestion:
If swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
If inhaled, remove to fresh air. 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 chemical 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. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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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# 7210-77-7: Personal Protective Equipment Eyes: Wear chemical splash goggles.
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: Powder and chunks
Color: off-white to yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 48 - 50 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: C8H11NO2S
Molecular Weight: 185.25

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Oxidizing agents, reducing agents, acids, bases.
Hazardous Decomposition Products:
Hydrogen cyanide, sulfur dioxide, carbon monoxide, oxides of nitrogen, carbon dioxide, sulfuric acid, nitric acid.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 7210-77-7 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Ethyl 2,4-dimethylthiazole-5-carboxylate - 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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
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: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 7210-77-7: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 7210-77-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 7210-77-7 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：

  2,4-二甲基噻唑-5-羧酸乙酯 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 以90%的产率得到2,4-二甲基-1,3-噻唑-5-羧酸
  参考文献：
  名称：

  噻唑和苯并噻唑衍生物作为具有体内抗炎特性的选择性大麻素CB2激动剂的构效关系

  摘要：

  CB 2受体激动剂用作缺乏精神病副作用的抗炎药的强大治疗潜力引起了人们的极大兴趣。我们在本文中描述了新型噻唑和苯并噻唑衍生物的合理设计和合成，以及它们对CB1和CB2受体的结合亲和力和功能活性的评估。具有通式的串联ñ - （3-戊基苯并[ d ]噻唑-2（3 H ^） -亚基）甲酰胺（化合物6A-6D）显示出朝向CB 2受体具有最高的亲和力和选择性与ķ我S IN皮摩尔或低纳摩尔范围和选择性指数（K i hCB1 / K ihCB2）达到429倍。值得注意的是，在低纳摩尔范围内的EC 50 s的细胞测定中，这些化合物还显示出激动性功能活性。更有趣的是，化合物6d（3-（三氟甲基）苯甲酰胺衍生物）在小鼠模型中表现出显着的抗DSS诱导的急性结肠炎的保护作用。

  DOI：

  10.1016/j.ejmech.2019.07.002
• 作为产物：
  描述：

  硫代乙酰胺 、 2-氯乙酰乙酸乙酯 以 乙醇 为溶剂， 反应 24.0h， 以91.3%的产率得到2,4-二甲基噻唑-5-羧酸乙酯
  参考文献：
  名称：

  噻唑和苯并噻唑衍生物作为具有体内抗炎特性的选择性大麻素CB2激动剂的构效关系

  摘要：

  CB 2受体激动剂用作缺乏精神病副作用的抗炎药的强大治疗潜力引起了人们的极大兴趣。我们在本文中描述了新型噻唑和苯并噻唑衍生物的合理设计和合成，以及它们对CB1和CB2受体的结合亲和力和功能活性的评估。具有通式的串联ñ - （3-戊基苯并[ d ]噻唑-2（3 H ^） -亚基）甲酰胺（化合物6A-6D）显示出朝向CB 2受体具有最高的亲和力和选择性与ķ我S IN皮摩尔或低纳摩尔范围和选择性指数（K i hCB1 / K ihCB2）达到429倍。值得注意的是，在低纳摩尔范围内的EC 50 s的细胞测定中，这些化合物还显示出激动性功能活性。更有趣的是，化合物6d（3-（三氟甲基）苯甲酰胺衍生物）在小鼠模型中表现出显着的抗DSS诱导的急性结肠炎的保护作用。

  DOI：

  10.1016/j.ejmech.2019.07.002

文献信息

• BENZAZEPINE DERIVATIVES, PROCESS FOR THE PREPARATION OF THE SAME AND USES THEREOF
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP1186604A1

  公开（公告）日：2002-03-13

  Compounds of the general formula (I): or salts thereof, which exhibit CCR5 antagonism and exert preventive and therapeutic effects against HIV infections: wherein R1 is a 5- to 6-membered aromatic ring which bears a substituent represented by the general formula: R-Z1-X-Z2- (wherein R1 is hydrogen or optionally substituted hydrocarbyl; X is optionally substituted alkylene; and Z1 and Z2 are each a heteroatom) and may be further substituted, with R being optionally bonded to the aromatic ring to form another ring; Y is optionally substituted imino; and R2 and R3 are each optionally substituted aliphatic hydrocarbyl or an optionally substituted hetero-alicyclic group.

  具有一般公式(I)的化合物： 或其盐，具有CCR5拮抗作用，并对HIV感染具有预防和治疗作用：其中R1是一个5至6成员的芳香环，带有一个由一般公式表示的取代基：R-Z1-X-Z2-（其中R1是氢或可选地取代的碳氢基；X是可选地取代的亚烷基；Z1和Z2都是杂原子）并可进一步取代，R可可选地与芳香环结合形成另一个环；Y是可选地取代的亚胺；R2和R3各自是可选地取代的脂肪族碳氢化合物或一个可选地取代的杂环脂肪族基团。
• [EN] IMIDAZO-PYRIDINE COMPOUNDS AS PAD INHIBITORS<br/>[FR] COMPOSÉS IMIDAZO-PYRIDINE À UTILISER EN TANT QU'INHIBITEURS DE PAD
  申请人：JUBILANT BIOSYS LTD

  公开号：WO2019077631A1

  公开（公告）日：2019-04-25

  Heterocyclic compounds of Formula (I), (II), and (III) are described herein along with their polymorphs, stereoisomers, prodrugs, solvates, co-crystals, intermediates, pharmaceutically acceptable salts, and metabolites thereof. The compounds described herein, their polymorphs, stereoisomers, prodrugs, solvates, co-crystals, intermediates, pharmaceutically acceptable salts, and metabolites thereof are PAD4 inhibitors and may be useful in the treatment of various disorders, for example rheumatoid arthritis, vasculitis, systemic lupus erythematosis, cutaneous lupus erythematosis, ulcerative colitis, cancer, cystic fibrosis, asthma, multiple sclerosis and psoriasis. The process of preparation of the compounds of Formula (I), (II), and (III), their polymorphs, stereoisomers, prodrugs, solvates, co-crystals, intermediates, pharmaceutically acceptable salts, and metabolites thereof, along with a pharmaceutical composition comprising a compound of Formula (I), Formula (II), Formula (III), or a pharmaceutically acceptable salt thereof have also been described.

  公式（I）、（II）和（III）的杂环化合物以及它们的多晶形态、立体异构体、前药、溶剂合物、共晶体、中间体、药学上可接受的盐和代谢物在本文中被描述。本文描述的化合物、它们的多晶形态、立体异构体、前药、溶剂合物、共晶体、中间体、药学上可接受的盐和代谢物是PAD4抑制剂，可能在治疗各种疾病中有用，例如类风湿关节炎、血管炎、系统性红斑狼疮、皮肤红斑狼疮、溃疡性结肠炎、癌症、囊性纤维化、哮喘、多发性硬化和牛皮癣。还描述了制备公式（I）、（II）和（III）的化合物、它们的多晶形态、立体异构体、前药、溶剂合物、共晶体、中间体、药学上可接受的盐和代谢物的过程，以及包含公式（I）、公式（II）、公式（III）的化合物或其药学上可接受的盐的药物组合物。
• Design, synthesis and biological evaluation of novel thiazole-derivatives as mitochondrial targeting inhibitors of cancer cells
  作者：Xin Dang、Shuwen Lei、Shuhua Luo、Yixin Hu、Juntao Wang、Dongdong Zhang、Dan Lu、Faqin Jiang、Lei Fu

  DOI：10.1016/j.bioorg.2021.105015

  日期：2021.9

  production assay to assess the selected compounds inhibitory effect on HeLa cells energy production. The results displayed the test compounds significantly restrained ATP production of cancer cells. Overall, we have designed and synthesized a series of compounds which exhibited significant cytotoxicity against cancer cells and effectively inhibited mitochondrial energy production.

  线粒体是细胞维持必要代谢活动的关键能量生产来源。针对功能失调的线粒体特征一直是线粒体相关疾病研究的热点。对癌性线粒体代谢的研究是肿瘤治疗中持续关注的问题。在此，我们基于我们早期对线粒体靶向剂的研究，着手评估新型 TPP-噻唑衍生物家族的抗癌活性。具体而言，我们设计并合成了一系列 TPP-噻唑衍生物，并通过 MTT 测定显示大多数合成的化合物有效抑制了三种癌细胞系（HeLa、PC3 和 MCF-7）。在结构修改后，我们探索了 SAR 关系并确定了最有希望的化合物R13（IC50 of 5.52 μM) 用于进一步研究。同时，我们进行了 ATP 产生测定以评估所选化合物对 HeLa 细胞能量产生的抑制作用。结果显示测试化合物显着抑制癌细胞的ATP产生。总体而言，我们设计并合成了一系列对癌细胞具有显着细胞毒性并有效抑制线粒体能量产生的化合物。
• One-Pot Telescoped Synthesis of Thiazole Derivatives from β-Keto Esters and Thioureas Promoted by Tribromoisocyanuric Acid
  作者：Marcio de Mattos、Vitor de Andrade

  DOI：10.1055/s-0037-1610243

  日期：2018.12

  and quinoxalines, respectively. This approach enables telescoping of the two steps into a single process. A simple and efficient one-pot protocol has been developed for the synthesis of thiazole derivatives from readily available starting materials. Tribromoisocyanuric acid was successfully used for α-monohalogenation of β-keto esters in aqueous medium, which in the presence of thiourea and DABCO produced

  献给W.布鲁斯Kover教授在他的80之际届周年 抽象的 已经开发了一种简单有效的一锅操作规程，用于从易于获得的起始原料合成噻唑衍生物。三溴异氰尿酸已成功用于水性介质中的β-酮酯的α-单卤代反应，在硫脲和DABCO的存在下，其产率高达87％，生成了相应的2-氨基噻唑。反应扩展至硫代乙酰胺和邻苯二胺导致分别产生2-甲基噻唑和喹喔啉。这种方法可以将两个步骤伸缩到一个流程中。 已经开发了一种简单有效的一锅操作规程，用于从易于获得的起始原料合成噻唑衍生物。三溴异氰尿酸已成功用于水性介质中的β-酮酯的α-单卤代反应，在硫脲和DABCO的存在下，其产率高达87％，生成了相应的2-氨基噻唑。反应扩展至硫代乙酰胺和邻苯二胺导致分别产生2-甲基噻唑和喹喔啉。这种方法可以将两个步骤伸缩到一个流程中。
• Dehydroamino acids
  申请人：——

  公开号：US20020161237A1

  公开（公告）日：2002-10-31

  Compounds of formula 1 and 1-1, 1 wherein R 1 is hydrogen, hydroxy, amino or halogen, R 2 is hydrogen, hydroxy, or halogen and R 3 is hydrogen (Formula 1) or R 1 is hydrogen and R 2 and R 3 taken together with the ethenylene group connecting them form phenyl, pyrrole, pyrroline, oxopyrroline, pyrazole, triazole, or imidazole (Formula 1-1), A is 2 R 4 R 5 are hydrogen, methyl, ethyl or halogen except that R 4 r 5 cannot both be hydrogen; and 1) B is hydrogen, or lower alkyl; or 2) B is 3 where R 6 R 7 R 8 and R 9 are independently hydrogen, hydroxy, aminosulfonyl, halogen, lower alkoxy, cyano, amino, lower alkyl, lower alkyl amino, or nitro; or 3) B is 4 where R 10 is hydrogen, hydroxy, halogen, or lower alkyl and C is a five- or six- membered ring with 0 to 3 heteroatoms which heteroatoms are selected from nitrogen, oxygen, and sulfur, which ring may be unsubstituted or mono- or di- substituted with lower alkyl, cycloalkyl, amino, or substituted amino; 4) B is 5 where X and Y are independently methylene or nitrogen; or 5) B is 6 where at leat one of T, U, V, or W is nitrogen, and any of T, U, V or W which is carbon may be substituted with lower alkyl, lower alkyl amino, lower alkoxy, hydroxy, aminosulfonyl, halogen, cyano, amino, or nitro; or 6) B is 7 where Y is carbon or nitrogen; or 7) B is a five-membered aromatic ring with 1 to 3 heteratoms selected from nitrogen, oxygen, and sulfur which ring may be unsubstituted or mono- or di-substituted with lower alkyl, cycloalky, trifluoroloweralkyl, amino, halogen, substituted amino, or which ring may be fused with a 5 or 6 membered aromatic ring containing 0 to 3 heteroatoms which heteroatoms are selected from nitrogen, oxygen, and sulfur; and pharmaceutically acceptable salts thereof, and related prodrugs, pharmaceutical compositions and methods of treatment, which compounds are useful for treating psoriasis.

  式1和1-1的化合物， 其中R1是氢，羟基，氨基或卤素，R2是氢，羟基或卤素，R3是氢（式1）或R1是氢，R2和R3连同连接它们的乙烯基团形成苯基，吡咯，吡咯烯，氧代吡咯烯，吡唑，三唑或咪唑（式1-1），A是 R4R5是氢，甲基，乙基或卤素，但R4R5不能同时为氢；和 1）B是氢或低碳烷基；或 2）B是 R6R7R8和R9独立地是氢，羟基，氨基磺酰基，卤素，低烷氧基，氰基，氨基，低烷基，低烷基氨基或硝基； 或3）B是 R10是氢，羟基，卤素或低碳烷基，C是具有0到3个异原子的五元或六元环，这些异原子选自氮，氧和硫，该环可以未取代或单取代或双取代为低烷基，环烷基，氨基或取代氨基； 4）B是 X和Y独立地是亚甲基或氮；或 5）B是 至少T，U，V或W中的一个是氮，任何是碳的T，U，V或W可以被低烷基，低烷基氨基，低烷氧基，羟基，氨基磺酰基，卤素，氰基，氨基或硝基取代；或 6）B是 Y是碳或氮； 或 7）B是具有1到3个异原子的氮，氧和硫中选择的五元芳香环，该环可以未取代或单取代或双取代为低烷基，环烷基，三氟低烷基，氨基，卤素，取代氨基，或该环可以与含有0到3个异原子的五元或六元芳香环融合，这些异原子选自氮，氧和硫；及其药学上可接受的盐，相关的前药，药物组合物和治疗方法，这些化合物对治疗牛皮癣有用。