恶唑-5-甲酸甲酯 | 121432-12-0

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 恶唑-5-甲酸甲酯
• 中文别名: 恶唑-5-羧酸甲酯
• 英文名称: methyl oxazole-5-carboxylate
• 英文别名: Methyl 5-oxazolecarboxylate；methyl 1,3-oxazole-5-carboxylate
• CAS: 121432-12-0
• 化学式: C₅H₅NO₃
• mdl: MFCD00144774
• 分子量: 127.1
• InChiKey: JGJDORZNOSWWDS-UHFFFAOYSA-N

物化性质

• 熔点：
  44-46 °C
• 沸点：
  184.0±13.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  52.3
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Name:	Methyl 5-oxazolecarboxylate 96% Material Safety Data Sheet
Synonym:
CAS:	121432-12-0

Section 1 - Chemical Product MSDS Name:Methyl 5-oxazolecarboxylate 96% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
121432-12-0	Methyl 5-oxazolecarboxylate, 96%	96	unlisted

Hazard Symbols: Not available.
Risk Phrases:

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Appearance: slightly yellow.
Not available.
Target Organs: None.
Potential Health Effects
The toxicological properties of this material have not been investigated. Use appropriate procedures to prevent opportunities for direct contact with the skin or eyes and to prevent inhalation.

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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 immediately.
Skin:
Get medical aid. Flush skin with plenty of soap and water for at least 15 minutes while removing contaminated clothing and shoes.
Remove contaminated clothing and shoes.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Get medical aid immediately.
Inhalation:
Get medical aid immediately. Remove from exposure to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
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 agent most appropriate to extinguish fire.

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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.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry place. Keep container closed when not in use.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels.
Exposure Limits +--------------------+-------------------+-------------------+-----------------+ | Chemical Name | ACGIH | NIOSH |OSHA - Final PELs| |--------------------|-------------------|-------------------|-----------------| | Methyl 5-oxazolecar|none listed |none listed |none listed | | boxylate, 96% | | | | +--------------------+-------------------+-------------------+-----------------+ OSHA Vacated PELs: Methyl 5-oxazolecarboxylate, 96%: No OSHA Vacated PELs are listed for this chemical.
Personal Protective Equipment Eyes: Wear chemical goggles.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin.
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 a respirator's use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Not available.
Appearance: slightly yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 40.00 - 42.00 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
NFPA Rating: Not published.
Explosion Limits, Lower: Not available.
Upper: Not available.
Decomposition Temperature:
Solubility:
Specific Gravity/Density:
Molecular Formula: C5H5NO3
Molecular Weight: 127.09

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, strong oxidants.
Incompatibilities with Other Materials:
Not available.
Hazardous Decomposition Products:
Irritating and toxic fumes and gases.
Hazardous Polymerization: Not available.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 121432-12-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Methyl 5-oxazolecarboxylate, 96% - Not listed by ACGIH, IARC, NIOSH, NTP, or OSHA.
See actual entry in RTECS for complete information.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Chemical waste generators must determine whether a discarded chemical is classif as a hazardous waste.
US EPA guidelines for the classification determination are listed in 40 CFR Part Additionally, waste generators must consult state and local hazardous waste regu ensure complete and accurate classification.
RCRA P-Series: None listed.
RCRA U-Series: None listed.

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Section 14 - TRANSPORT INFORMATION

CDG/CPL
Not classified as hazardous for supply.
Canadian TDG
No information available.

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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# 121432-12-0: No information available.
United Kingdom Occupational Exposure Limits
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
WHMIS: Not available.
CAS# 121432-12-0 is not listed on Canada's Ingredient Disclosure List.
Exposure Limits
US FEDERAL
TSCA
CAS# 121432-12-0 is not listed on the TSCA inventory.
It is for research and development use only.
Health & Safety Reporting List
None of the chemicals are on the Health & Safety Reporting List.
Chemical Test Rules
None of the chemicals in this product are under a Chemical Test Rule.
Section 12b
None of the chemicals are listed under TSCA Section 12b.
TSCA Significant New Use Rule
None of the chemicals in this material have a SNUR under TSCA.
SARA
Section 302 (RQ)
None of the chemicals in this material have an RQ.
Section 302 (TPQ)
None of the chemicals in this product have a TPQ.
Section 313
No chemicals are reportable under Section 313.
Clean Air Act:
This material does not contain any hazardous air pollutants.
This material does not contain any Class 1 Ozone depletors.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

5-恶唑甲酸甲酯是一种酯类衍生物，可用作化学试剂。

反应信息

• 作为反应物：
  描述：

  恶唑-5-甲酸甲酯 在 lithium aluminium tetrahydride 作用下， 生成 噁唑-5-甲醇
  参考文献：
  名称：

  Inactivation of O⁶-Alkylguanine-DNA Alkyltransferase. 1. Novel O⁶-(Hetarylmethyl)guanines Having Basic Rings in the Side Chain

  摘要：

  A number of novel guanine derivatives containing heterocyclic moieties at the O-6-position have been synthesized using a purine quaternary salt which reacts with alkoxides under mild conditions. Initially O-6-substituents were investigated in which the benzene ring of the known agent, O-6-benzylguanine, was replaced by unsubstituted heterocyclic rings. The ability of these agents to inactivate the DNA repair protein O-6-alkylguanine-DNA alkyltransferase (ATase), both as pure recombinant protein and in the human lymphoblastoid cell line Raji, has been compared with that of O-6-benzylguanine. The present paper focuses on O-6-substituents with basic rings, and under standard conditions several of them proved more effective than benzyl for inactivation of both recombinant and Raji ATase. Among the pyridine derivatives, the 2-picolyl compound 7 is not very active in contrast to the 3- and 4-picolyl compounds, and this influenced our choice of isomers of other basic ring systems for study. Since halogen substitution in the thiophene ring considerably increased the activity (17 versus 6), similar modifications in the pyridine series were examined. The more polar O-6-substituents in this study are on the whole compatible with the stereochemical requirements of the ATase protein, and their pharmacological properties may be valuable in subsequent in vivo investigations, particularly the thenyl (6), 5-thiazolylmethyl (12), 5-bromothenyl (17), and 2-chloro-4-picolyl (21) derivatives.

  DOI：

  10.1021/jm9708644
• 作为产物：
  描述：

  methyl 2-oxo-2-(1,2,4-triazol-1-yl)acetate 以60%的产率得到
  参考文献：
  名称：

  MEQUEATIAU, ANDRE;FLAMMANG, ROBERT;ABDELOUAHAB, FOUAD-BACHIR BEN, HETEROCYCLES, 29,(1989) N, C. 103-114

  摘要：

  DOI：

文献信息

• Discovery of Reldesemtiv, a Fast Skeletal Muscle Troponin Activator for the Treatment of Impaired Muscle Function
  作者：Scott E. Collibee、Gustave Bergnes、Chihyuan Chuang、Luke Ashcraft、Jeffrey Gardina、Marc Garard、Chris R. Jamison、Kevin Lu、Pu-Ping Lu、Alexander Muci、Antonio Romero、Ellen Valkevich、Wenyue Wang、Jeffrey Warrington、Bing Yao、Nickie Durham、James Hartman、Anna Marquez、Aaron Hinken、Julia Schaletzky、Donghong Xu、Darren T. Hwee、David Morgans、Fady I. Malik、Bradley P. Morgan

  DOI：10.1021/acs.jmedchem.1c01067

  日期：2021.10.28

  reported. Property-based optimization of high throughput screening hit 1 led to compounds with improved free exposure and in vivo muscle activation potency compared to the first-generation FSTA, tirasemtiv. Reldesemtiv demonstrated increased muscle force generation in a phase 1 clinical trial and is currently being evaluated in clinical trials for the treatment of amyotrophic lateral sclerosis.

  据报道，reldesemtiv 是一种第二代快速骨骼肌肌钙蛋白激活剂 (FSTA)，可在次最大刺激频率下增加力的产生。与第一代 FSTA tirasemtiv 相比，基于特性的高通量筛选命中1优化导致化合物具有更好的游离暴露和体内肌肉激活效力。Reldesemtiv 在 1 期临床试验中证明了肌肉力量的产生增加，目前正在临床试验中评估治疗肌萎缩侧索硬化症。
• Application of C–H Functionalization in the Development of a Concise and Convergent Route to the Phosphatidylinositol-3-kinase Delta Inhibitor Nemiralisib
  作者：Robert N. Bream、Hugh Clark、Dean Edney、Antal Harsanyi、John Hayler、Alan Ironmonger、Nadine Mc Cleary、Natalie Phillips、Catherine Priestley、Alastair Roberts、Philip Rushworth、Peter Szeto、Michael R. Webb、Katherine Wheelhouse

  DOI：10.1021/acs.oprd.0c00486

  日期：2021.3.19

  describes the development of an improved and scalable method for the manufacture of nemiralisib, a phosphatidylinositol-3-kinase delta inhibitor. Incorporation of three consecutive catalytic reactions, including a palladium-catalyzed C–H functionalization and an iridium-catalyzed borylation, significantly simplified and shortened the synthetic sequence. The revised route was successfully implemented in a pilot

  本文介绍了一种改进的可扩展方法，用于生产nemiralisib（一种磷脂酰肌醇-3-激酶δ抑制剂）。结合三个连续的催化反应，包括钯催化的C–H功能化和铱催化的硼化反应，显着简化并缩短了合成顺序。修订后的路线已在多千克规模的中试工厂中成功实施，以交付大于100千克的产品。
• Development of Flexible and Scalable Routes to Two Phosphatidinylinositol-3-kinase Delta Inhibitors via a Common Intermediate Approach
  作者：Dean Edney、David G. Hulcoop、John H. Leahy、Lois E. Vernon、Mark D. Wipperman、Robert N. Bream、Michael R. Webb

  DOI：10.1021/acs.oprd.8b00006

  日期：2018.3.16

  development of a flexible route to two candidate drug molecules by a common intermediate approach. Key reactions include Negishi and Suzuki couplings to form biaryl bonds. Conditions for a Miyaura borylation of heteroaryl bromides were also developed. Heteroaryl trifluoroborates and aryl chlorides were used as coupling partners in the Suzuki reaction, thereby minimizing detrimental side reactions such as protodeboronation

  本文介绍了通过一种常见的中间方法开发和灵活地合成两种候选药物分子的途径。关键反应包括Negishi和Suzuki偶联形成联芳基键。还开发了对杂芳基溴进行宫浦硼化的条件。杂芳基三氟硼酸酯和芳基氯化物在Suzuki反应中用作偶联伙伴，从而使有害的副反应（如原脱硼烷基化和氧化均偶联）最小化。还开发了一套使用频哪醇硼酸酯与氟化氢钾作为添加剂的补充反应条件，并将其用于制备5千克用于早期临床试验的原料药。
• O.sup.6 -substituted guanine derivatives, a process for their
  申请人：Cancer Research Campaign Technology Limited

  公开号：US06043228A1

  公开（公告）日：2000-03-28

  O.sup.6 -hetarylalkyl- or naphthylalkylguanine derivatives of the formula ##STR1## wherein Y is H, ribosyl, deoxyribosyl, or R"XCHR', wherein X is O or S, R" and R"' are alkyl, or substituted derivatives thereof, R' is H, or alkyl or hydroxyalkyl R is (i) a cyclic group having at least one 5- or 6-membered heterocyclic ring, optionally with a carbocylic or heterocyclic ring fused thereto, the or each heterocyclic ring having at least one hereto atom chosen from O, N, or S, or a substituted derivative thereof; or (ii) naphthyl or a substituted derivative thereof and pharmaceutically acceptable salts thereof, exhibit the ability to deplete O.sup.6 -alkylguanine-DNA alkyltransferase (ATase) activity. A process for preparation of the compounds is described. The compounds have utility in combination with alkylating agents in the chemotherapeutic treatment of tumour cells.

  O.sup.6-芳基烷基或萘基烷基鸟嘌呤衍生物的公式为##STR1##其中Y为H、核糖基、脱氧核糖基或R"XCHR'，其中X为O或S，R"和R"'为烷基或其取代衍生物，R'为H、烷基或羟基烷基，R为（i）至少具有一个5-或6-成员杂环环的环状基团，可选地与碳环或杂环融合在一起，每个杂环环至少有一个从O、N或S中选择的杂原子，或其取代衍生物；或（ii）萘基或其取代衍生物和药学上可接受的盐，具有耗竭O.sup.6-烷基鸟嘌呤-DNA烷基转移酶（ATase）活性的能力。还描述了制备化合物的过程。该化合物在与烷化剂结合的化疗治疗肿瘤细胞中具有实用性。
• Process for the synthesis of 2-aminoxazole compounds
  申请人：AB Science

  公开号：US08080669B2

  公开（公告）日：2011-12-20

  The present invention relates to a process for synthesizing in good yield substituted 2-aminoaryloxazole compounds of formula I which are useful as certain tyrosine kinase inhibitors and more particularly as c-kit, bcr-abl, Flt-3 and mutant forms thereof.

  本发明涉及一种合成取代的2-氨基氧唑化合物(I式)的方法，该方法得率高，这些化合物可用作某些酪氨酸激酶抑制剂，特别是作为c-kit、bcr-abl、Flt-3和其突变形式的抑制剂。