potassium 5-methyl-1,3,4-oxadiazole-2-carboxylate | 888504-28-7

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: potassium 5-methyl-1,3,4-oxadiazole-2-carboxylate
• 英文别名: potassium 5-methyl-[1,3,4]oxadiazol-2-carboxylate；potassium;5-methyl-1,3,4-oxadiazole-2-carboxylate
• CAS: 888504-28-7
• 化学式: C₄H₃N₂O₃*K
• 分子量: 166.178
• InChiKey: BRHMYHXNUGVBCU-UHFFFAOYSA-M

物化性质

• 熔点：
  258.3 °C (decomp)
• 溶解度：
  可溶于水

计算性质

• 辛醇/水分配系数(LogP)：
  -4.25
• 重原子数：
  10
• 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：
  79
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  存储条件：2～8℃，惰性气体保护下保存。

SDS

---

SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 5-Methyl-1,3,4-Oxadiazole-2-Carboxylic Acid,
Potassium Salt
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

---

SECTION 2: Hazards identification
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
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.

---

SECTION 3: Composition/information on ingredients
Substances
Molecular weight : 166,18 g/mol
No components need to be disclosed according to the applicable regulations.

---

SECTION 4: First aid measures
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
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

---

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

---

SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapours, mist or gas.
For personal protection see section 8.
Environmental precautions
No special environmental precautions required.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

---

SECTION 7: Handling and storage
Precautions for safe handling
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

---

SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
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
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
No special environmental precautions required.

---

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

---

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

---

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.

---

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

---

SECTION 13: Disposal considerations
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

---

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

---

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

---

SECTION 16: Other information
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.

制备方法与用途

应用

5-甲基-1,3,4-恶二唑-2-羧酸钾在常温常压下是灰白色固体，可溶于水。它主要用作有机合成和医药化学中间体，可用于药物分子拉替拉韦和雷特格韦的合成。

制备

向甲苯（32 L）中加入甲基四唑（29.7 mol）和三乙胺（3.03公斤，30.0 mol），缓慢滴加草酰氯乙酯（29.4 mol）。在滴加过程中保持温度低于5度，并在0~5度下搅拌反应1小时。通过过滤除去三乙胺氯化氢盐，用27升冷甲苯清洗固体。

将合并后的滤液冷却至0度，然后缓慢加入到50度、15 L的甲苯热溶液中，在70度下持续搅拌1小时。随后将反应冷却至20度，并用5 L 10%盐水洗涤甲苯溶液。接着将甲苯旋干，再加入乙醇直至终体积约40 L，然后在10度下冷却反应混合物。

向该浓浆液中加入KOH，在室温下搅拌40分钟后，可以观察到恶二唑K盐结晶析出。通过过滤收集固体，并在真空下干燥过夜即可得到5-甲基-1,3,4-恶二唑-2-羧酸钾。

反应信息

• 作为反应物：
  描述：

  potassium 5-methyl-1,3,4-oxadiazole-2-carboxylate 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 乙腈 为溶剂， 反应 1.0h， 生成 5-甲基-1,3,4-噁二唑-2-羰酰氯
  参考文献：
  名称：

  开发HIV整合酶抑制剂Raltegravir钾的第二代高效生产路线

  摘要：

  通过氨基mid肟DMAD加合物6的热重排，开发了合成raltegravir钾1的生产路线，以构建关键的，高度官能化的羟基嘧啶酮核心7。利用该路线1，以九个线性化学步骤制备，总产率为22％。随后开发了第二代合成方法，解决了最初合成方法中的关键化学，生产率和环境影响问题。新合成的亮点包括高度选择性的甲基化，高3-4倍的生产率以及所产生的有机废物和含水废物减少了65％。有效的第二代生产路线提供了拉格韦韦钾1 总产量的35％。

  DOI：

  10.1021/op100257r
• 作为产物：
  描述：

  5-甲基-1,3,4-噁二唑-2-羧酸乙酯 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 生成 potassium 5-methyl-1,3,4-oxadiazole-2-carboxylate
  参考文献：
  名称：

  新型甾体 1,3,4-恶二唑的杀虫活性的设计、合成和研究

  摘要：

  设计并合成了一系列具有取代的1,3,4-恶二唑结构的新型甾体衍生物，并评估了目标化合物对五种蚜虫的杀虫活性。大多数测试的化合物表现出对鼠尾草（Hausmann）、桃蚜和柑橘蚜的有效杀虫活性。化合物20g和24g对E. lanigerum 的活性最高，LC 50值分别为 27.6 和 30.4 μg/mL。E. lanigerum中肠细胞的超微结构变化通过透射电子显微镜检测，表明这些甾体恶唑衍生物可能通过破坏昆虫中肠细胞的线粒体和核膜来发挥其杀虫活性。此外，田间试验表明，化合物20g表现出与阳性对照毒死蜱和噻虫嗪对E. lanigerum的效果相似，在200 μg/mL剂量下21天后达到89.5%的控制率。我们还通过测定三种杀虫剂解毒酶的活性研究了E. lanigerum 中目标化合物的水解和代谢。复合物20g50 μg/mL 对羧酸酯酶的抑制作用类似于已知的抑制剂磷酸三苯酯。上述结果证明了

  DOI：

  10.1021/acs.jafc.1c00088

文献信息

• 3,4-二苯基-4H-1,2,4-三唑衍生物及其制备 方法和应用
  申请人：上海翰森生物医药科技有限公司

  公开号：CN106349233B

  公开（公告）日：2021-06-01

  本发明公开了3,4‑二苯基‑4H‑1,2,4‑三唑衍生物及其制备方法和应用。具体地，本发明涉及具有式(I)结构的3,4‑二苯基‑4H‑1,2,4‑三唑衍生物、其立体异构体或其药学上可接受盐，其中式(I)中各取代基的定义与说明书中的定义相同。这些结构新颖的化合物具有热休克蛋白HSP90抑制活性，可用于治疗癌症、神经退行性疾病、炎症性疾病、自身免疫性疾病、缺血性脑损伤等用途，具有广阔的应用前景。
• [EN] PYRIDIN-3-YL ACETIC ACID DERIVATIVES AS INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION<br/>[FR] DÉRIVÉS D'ACIDE PYRIDIN-3-YLE ACÉTIQUE UTILISÉS COMME INHIBITEURS DE LA RÉPLICATION DU VIRUS DE L'IMMUNODÉFICIENCE HUMAINE
  申请人：VIIV HEALTHCARE UK (NO 5) LTD

  公开号：WO2017025915A1

  公开（公告）日：2017-02-16

  Disclosed are compounds of Formula (I), including pharmaceutically acceptable salts, pharmaceutical compositions comprising the compounds, methods for making the compounds and their use in inhibiting HIV integrase and treating those infected with HIV or AIDS.

  揭示了公式（I）的化合物，包括药学上可接受的盐，包含这些化合物的药物组合物，制备这些化合物的方法以及它们在抑制HIV整合酶和治疗HIV或艾滋病感染者中的用途。
• 4,5-二苯基异噁唑衍生物及其制备方法和应 用
  申请人：上海翰森生物医药科技有限公司

  公开号：CN106349180B

  公开（公告）日：2020-05-19

  本发明公开了4,5‑二苯基异噁唑衍生物及其制备方法和应用。具体地，本发明涉及具有式(I)结构4,5‑二苯基异噁唑衍生物、其立体异构体或其药学上可接受盐，其中式(I)中各取代基的定义与说明书中的定义相同。这些结构新颖的化合物具有热休克蛋白HSP90抑制活性，可用于治疗癌症、神经退行性疾病、炎症性疾病、自身免疫性疾病、缺血性脑损伤等用途，具有广阔的应用前景。
• [EN] AN IMPROVED PROCESS FOR THE PREPARATION OF RALTEGRAVIR<br/>[FR] PROCÉDÉ PERFECTIONNÉ POUR LA PRÉPARATION DE RALTÉGRAVIR
  申请人：AUROBINDO PHARMA LTD

  公开号：WO2016075605A1

  公开（公告）日：2016-05-19

  The present invention provides a process for the preparation of crystalline anhydrous compound of Formula (X), Further, the present invention relates to the use of compound of Formula (X) preparation of Raltegravir (I) or its pharmaceutically acceptable salt thereof.

  本发明提供了一种制备化合物分子式为(X)的结晶无水化合物的方法。此外，本发明涉及使用分子式为(X)的化合物制备拉替格韦(I)或其药用可接受盐。
• [EN] TRICYCLIC INHIBITORS OF HEPATITIS B VIRUS<br/>[FR] INHIBITEURS TRICYCLIQUES DU VIRUS DE L'HÉPATITE B
  申请人：OSPEDALE SAN RAFFAELE SRL

  公开号：WO2020030781A1

  公开（公告）日：2020-02-13

  The present invention relates to compounds that are inhibitors of hepatitis B virus (HBV). Compounds of this invention are useful alone or in combination with other agents for treating, ameliorating, preventing or curing HBV infection and related conditions. The present invention also relates to pharmaceutical compositions containing said compounds.

  本发明涉及抑制乙型肝炎病毒（HBV）的化合物。本发明的化合物可单独使用或与其他药剂结合用于治疗、改善、预防或治愈HBV感染及相关疾病。本发明还涉及含有上述化合物的药物组合物。