4-甲基-1,3-噻唑-2(3H)-酮 | 32497-10-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-甲基-1,3-噻唑-2(3H)-酮
• 中文别名: 4-甲基噻唑-2(3H)-酮
• 英文名称: 4-methyl-2(3H)-thiazolone
• 英文别名: 4-methyl-2H-1,3-thiazolin-2-one；4-methyl-2-thiazolinone；4-methyl-3H-thiazol-2-one；4-Methyl-3H-thiazol-2-on；4-methyl-2-3H-thiazolone；4-Methyl-thiazolon-(2)；4-methyl-3H-1,3-thiazol-2-one
• CAS: 32497-10-2
• 化学式: C₄H₅NOS
• mdl: MFCD00970121
• 分子量: 115.156
• InChiKey: ZMEVDFFLOPFGCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2934100090

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 4-Methyl-1,3-thiazol-2(3h)-one
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: 4-Methyl-1,3-thiazol-2(3h)-one
CAS number: 32497-10-2

---

Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

---

Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

---

Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

---

Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

---

Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

---

Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C4H5NOS
Molecular weight: 115.2

---

Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, sulfur oxides.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-甲基-1,3-噻唑-2(3H)-酮 在 乙醚 、 五氯化磷 作用下， 生成 5-chloro-4-methyl-3H-thiazol-2-one
  参考文献：
  名称：

  Hantzsch, Chemische Berichte, 1927, vol. 60, p. 2538

  摘要：

  DOI：
• 作为产物：
  描述：

  2-ethoxy-4-methyl-thiazole 在 三溴化磷 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以80%的产率得到4-甲基-1,3-噻唑-2(3H)-酮
  参考文献：
  名称：

  SYNTHESIS OF THIAAZAHETEROCYCLE NUCLEOSIDE ANALOGUES

  摘要：

  The syntheses of thiazinone, thiazinedione and thiazolinone base modified nucleoside analogues have been discussed in both the deoxy- and ribosyl series. Both inter- and intramolecular N-glycosylations were evaluated.

  DOI：

  10.1081/ncn-120006829

文献信息

• Cardiotonic alkanoylthiazolones
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US04762849A1

  公开（公告）日：1988-08-09

  Novel alkanoylthiazolones enhance myocardial contractile force and are useful as cardiotonics in the treatment of heart failure.

  新型烷酰硫唑酮增强心肌收缩力，并在心力衰竭治疗中作为心力药物是有用的。
• Sonogashira Coupling of Functionalized Trifloyl Oxazoles and Thiazoles with Terminal Alkynes:  Synthesis of Disubstituted Heterocycles
  作者：Neil F. Langille、Les A. Dakin、James S. Panek

  DOI：10.1021/ol026099r

  日期：2002.7.1

  see text] This paper describes Sonogashira cross-coupling of functionalized 2-, 4-, and 5-trifloyl oxazoles and thiazoles with terminal alkynes. This methodology has been extended to 2,4-ditrifloylthiazoles, which results in regioselective cross-coupling at the C2-position of the thiazole. The resulting 2-alkynyl-4-trifloylthiazoles are effective electrophiles in a second palladium(0)-mediated cross-coupling

  [反应：参见正文]本文描述了功能化的2-，4-和5-三氟甲恶唑和噻唑与末端炔烃的Sonogashira交叉偶联。该方法已经扩展到2,4-二甲苯基噻唑，这导致在噻唑的C2位区域选择性交叉偶联。在第二个钯（0）介导的交叉偶联反应中，所得的2-炔基-4-三氟噻唑是有效的亲电子试剂。
• Synthesis of Five- and Six-Membered<i>N</i>-Phenylacetamido Substituted Heterocycles as Formyl Peptide Receptor Agonists
  作者：Claudia Vergelli、Igor A. Schepetkin、Giovanna Ciciani、Agostino Cilibrizzi、Letizia Crocetti、Maria Paola Giovannoni、Gabriella Guerrini、Antonella Iacovone、Liliya N. Kirpotina、Richard D. Ye、Mark T. Quinn

  DOI：10.1002/ddr.21370

  日期：2017.2

  Preclinical Research

  临床前研究
• Studies on bi-heterocyclic compounds. II. 5-Substituted thiazolones.
  作者：Hiroaki YAMAZAKI、Hidenori HARADA、Kenichi MATSUZAKI、Kimotomo YOSHIOKA、Muneaki TAKASE、Eiji OHKI

  DOI：10.1248/cpb.38.45

  日期：——

  Reactions of-methyl-2(3H)-thiazolones (5) with various N-alkoxycarbonyl pyridinium salts (6a-f) led to (N-alkoxycarbonyl dihydropyridyl)thiazolones (7a-f), oxidation of which yielded a new class of 5-pyridylthiazolones (8a-f). These reactions were applied to the synthesis of other azaarylthiazolones. Some of these azaarylthiazolones, particualrly 5-(4-pyridyl)thiazolones (8b, c) and 5-(4-quinolyl)thiazolones (14a, b), showed positive inotropic activity with little chronotropic effect on guinea pig left atria.

  用各种N-烷氧羰基吡啶镮盐(6a-f)与-甲基-2(3H)-噻唑啉酮(5)反应,得到(N-烷氧羰基二氢吡啶基)噻唑啉酮(7a-f)。使其氧化后得到一个新的5-吡啶基噻唑啉酮(8a-f)类化合物。将这些反应应用于其他氮杂芳基噻唑啉酮的合成。其中某些氮杂芳基噻唑啉酮,特别是5-(4-吡啶基)噻唑啉酮(8b,c)和5-(4-喹啉基)噻唑啉酮(14a,b),对豚鼠左心房表现出正性肌力作用,而对心率的作用很小。
• Synthesis of adamantane derivatives. LVIII. Reaction of 1-adamantyl chloride with some heterocyclic unsaturated silanes.
  作者：TADASHI SASAKI、AKIRA NAKANISHI、MASATOMI OHNO

  DOI：10.1248/cpb.30.2051

  日期：——

  Various silylated heterocycles having amide functionality were treated with 1-adamantyl chloride (1) in the presence of a Lewis acid to give the corresponding N-adamantylated heterocycles. If α-position to the reacting lactim nitrogen was substituted, the reaction no longer occurred, or the adamantylation occurred at the position other than the expected nitrogen. These facts are attributed to a steric blocking effect of the α-substituent. While the same treatment of the thioamide 46 gave the S-adamantylated product, 48 and 51 afforded in contrast the N- and S-adamantylated products, respectively ; this result can be explained in terms of steric effect. Analogously, silylated 2-pyrazolines and triazoles were adamantylated at nitrogen. The reactions of 2-trimethylsilylthiophene, furan and -pyridine with 1 failed to give site-selective monoadamantylation.

  在路易斯酸存在下，用 1-金刚烷酰氯（1）处理各种具有酰胺官能团的硅烷化杂环，得到相应的 N-金刚烷化杂环。如果反应的内酰胺氮的α位被取代，则不再发生反应，或者在预期氮以外的位置发生金刚烷基化反应。这些情况都归因于 α 取代基的立体阻滞效应。同样处理硫代酰胺 46 得到的是 S-金刚烷化产物，而 48 和 51 则分别得到了 N-和 S-金刚烷化产物；这一结果可以用立体效应来解释。类似地，硅烷化的 2-吡唑和三唑也在氮处发生了金刚烷化。2-三甲基硅基噻吩、呋喃和吡啶与 1 的反应未能产生位点选择性的单金刚烷化反应。

表征谱图