2-氧代-2,3-二氢-1H-咪唑-4-羧酸 | 39828-47-2

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 环羧酸
• 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-氧代-2,3-二氢-1H-咪唑-4-羧酸
• 英文名称: 2-Oxo-4-imidazolin-4-carbonsaeure
• 英文别名: 2-oxo-2,3-dihydro-1H-imidazole-4-carboxylic acid；2-oxo-1,3-dihydroimidazole-4-carboxylic acid
• CAS: 39828-47-2
• 化学式: C₄H₄N₂O₃
• mdl: MFCD02323264
• 分子量: 128.087
• InChiKey: XJSWLMGZMRUNLP-UHFFFAOYSA-N

物化性质

• 熔点：
  270 °C
• 密度：
  1.584±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  | 室温 干燥 |

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Oxo-2,3-dihydro-1H-imidazole-4-carboxylic acid
Synonyms:

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

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Section 3. Composition/information on ingredients.
Ingredient name: 2-Oxo-2,3-dihydro-1H-imidazole-4-carboxylic acid
CAS number: 39828-47-2

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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.

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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.

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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.

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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:

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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.

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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: C4H4N2O3
Molecular weight: 128.1

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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.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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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.

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

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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.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-氧代-2,3-二氢-1H-咪唑-4-羧酸 220.0 ℃ 、266.64 Pa 条件下， 生成 1,3-二氢咪唑-2-酮
  参考文献：
  名称：

  THE SYNTHESES OF 2-IMIDAZOLONE-4-CARBOXYLIC ACID AND 2-IMIDAZOLONE

  摘要：

  DOI：

  10.1021/ja01347a064
• 作为产物：
  描述：

  酒石酸 在 硫酸 、 三氧化硫 作用下， 生成 2-氧代-2,3-二氢-1H-咪唑-4-羧酸
  参考文献：
  名称：

  THE SYNTHESES OF 2-IMIDAZOLONE-4-CARBOXYLIC ACID AND 2-IMIDAZOLONE

  摘要：

  DOI：

  10.1021/ja01347a064

文献信息

• Chemistry of the neopolyoxins, pyrimidine and imidazoline nucleoside peptide antibiotics
  作者：Masakazu Uramoto、Kimie Kobinata、Kiyoshi Isono、Tsutomu Higashijima、Tatsuo Miyazawa、Ellen E. Jenkins、James A. McCloskey

  DOI：10.1016/0040-4020(82)80135-x

  日期：1982.1

  and C were isolated from the culture filtrate of Streptomyces cacaoi subsp. asoensis. Their absolute structures have been established on the basis of chemical and spectroscopic evidence. They are structural analogs of the polyoxins. As a nucleobase, neopolyoxin C possesses uracil, while neopolyoxins A and B contain the imidazoline moiety. A ring contraction reaction of pyrimidine nucleoside into imidazoline

  从可食链霉菌亚种的培养滤液中分离出新的几丁质合成酶抑制剂，新多恶菌素A，B和C。麻生太郎。它们的绝对结构是根据化学和光谱学证据确定的。它们是多氧合蛋白的结构类似物。作为多核新毒素C的核碱基，它具有尿嘧啶，而新多毒素A和B含有咪唑啉部分。嘧啶核苷到咪唑啉核苷的环收缩反应在核苷部分的结构确定中起关键作用。有人建议对新多毒素A和B的生物合成进行类似的转化。
• Enantioselective Strategy to the Spirocyclic Core of Palau'amine and Related Bisguanidine Marine Alkaloids
  作者：Anja S. Dilley、Daniel Romo

  DOI：10.1021/ol015864j

  日期：2001.5.1

  enantioselective strategy to the spirocyclic core found in the oroidin-derived family of bisguanidine marine alkaloids has been devised, premised on a biosynthetic proposal. Herein, we describe the successful implementation of this strategy, which entails a Diels-Alder reaction and a chlorination/ring contraction sequence that delivers the fully functionalized spirocyclic core. In this initial report, an intermolecular

  [结构：见正文]在生物合成方案的基础上，已设计出一种对映体选择性策略，该策略是在源自鸟苷的双胍海洋生物碱家族中发现的螺环核心。在本文中，我们描述了该策略的成功实施，该策略涉及Diels-Alder反应和提供完全功能化螺环核心的氯化/环收缩序列。在该初始报告中，分子间氯化反应生成的环戊烷在C17处相对于帕劳胺而言是异构体，在C11时相对于乙酰丙胺而言是异构体。
• Specific Force Deficit in Skeletal Muscles of Old Rats Is Partially Explained by the Existence of Denervated Muscle Fibers
  作者：M. G. Urbanchek、E. B. Picken、L. K. Kalliainen、W. M. Kuzon

  DOI：10.1093/gerona/56.5.b191

  日期：2001.5.1

  We tested the hypothesis that denervated muscle fibers account for part of the specific force (sF(0)) deficit observed in muscles from old adult (OA) mammals, Whole muscle force (F-0) was quantified for extensor digitorum longus (EDL) muscles of OA and young adult (YA) rats. EDL muscle sF(0) was calculated by dividing F-0 by either total muscle fiber cross-sectional area (CSA) or by innervated fiber CSA. Innervated fiber CSA was estimated from EDL muscle cross sections labeled for neural cell adhesion molecules, whose presence is a marker for muscle fiber denervation. EDL muscles from OA rats contained significantly more denervated fibers than muscles from YA rats (5.6% vs 1.1% of total CSA), When compared with YA muscle, oil muscle demonstrated deficits of 34.1% for F-0, 28.3% for sF(0), and 24.9 % for sF(0) calculated by using innervated CSA as the denominator, Denervated muscle fibers accounted for 11.3% of the specific force difference between normal YA and OA skeletal muscle, Other mechanisms in addition to denervation account for the majority of the sF(0) deficit with aging.
• A unified synthetic strategy toward oroidin-derived alkaloids premised on a biosynthetic proposal
  作者：Paul J. Dransfield、Anja S. Dilley、Shaohui Wang、Daniel Romo

  DOI：10.1016/j.tet.2005.12.068

  日期：2006.5

  Details of the evolution of a synthetic strategy toward the spirocyclic chlorocyclopentane core of oroidin-derived alkaloids, including the axinellamines and potentially adaptable to palau'amine, are described. A proposed refinement of the Kinnel-Scheuer biosynthetic proposal for palau'amine is posited. Studies undertaken to improve the regioselectivity and efficiency of a key Diels-Alder reaction utilizing a novel protecting group strategy, microwave chemistry, and other strategies are described. Further insights regarding the suitability of different protecting groups during the epoxidation/chlorination/ring contraction sequence are disclosed. Several interesting by-products from this reaction sequence are reported. These studies have led to a unified synthetic strategy to the axinellamines and palau'amine. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis and biological activity of 9-mercaptodethiobiotin—a putative biotin precursor in Escherichia coli
  作者：Robert L. Baxter、Dominic J. Camp、Andrew Coutts、Nicholas Shaw

  DOI：10.1039/p19920000255

  日期：——

  A total synthesis of (+/-)-9-mercaptodethiobiotin 3 via the aldehyde 9 is described. Compound (+/-)-3 does not function as a biotin replacement factor for an E. coli mutant (SA291) lacking the entire biotin synthesis operon (bioABFCD-) but supports growth of an E. coli bioA mutant. Compound (+/-)-3 also supports growth of transformed cells of SA291 carrying a plasmid encoding the E. coli biotin synthase (bioB) gene indicating that the compound may be able to substitute for dethiobiotin 2 as a substrate for biotin synthase.