1-乙基-1,4-二氢-5H-四唑-5-酮 | 69048-98-2

• 物质功能分类: 有机原料 - 酮类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-乙基-1,4-二氢-5H-四唑-5-酮
• 中文别名: 1-乙基-1H-四唑-5(4H)-酮
• 英文名称: 1-ethyl-1,4-dihydro-5H-tetrazol-5-one
• 英文别名: 1-ethyl-1,2-dihydro-5H-tetrazol-5-one；4-ethyl-1H-tetrazol-5-one
• CAS: 69048-98-2
• 化学式: C₃H₆N₄O
• mdl: MFCD00067004
• 分子量: 114.107
• InChiKey: YVVZUMUVGRLSRZ-UHFFFAOYSA-N

物化性质

• 熔点：
  80℃
• 沸点：
  121℃
• 密度：
  1.55
• 闪点：
  27℃
• 溶解度：
  可溶于氯仿（少许）、二氯甲烷（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  57.1
• 氢给体数：
  1
• 氢受体数：
  3

SDS

Name:	1-Ethyl-1 4-Dihydro-5H-Tetrazol-5-One 98+% Material Safety Data Sheet
Synonym:
CAS:	69048-98-2

Section 1 - Chemical Product MSDS Name:1-Ethyl-1 4-Dihydro-5H-Tetrazol-5-One 98+% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
69048-98-2	1-Ethyl-1,4-Dihydro-5H-Tetrazol-5-One	98	273-844-2

Hazard Symbols: XN
Risk Phrases: 22

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful if swallowed.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation. The toxicological properties of this material have not been fully investigated.
Skin:
May cause skin irritation. The toxicological properties of this material have not been fully investigated.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
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 immediately.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid immediately.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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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. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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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. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed.
Avoid ingestion and inhalation.
Storage:
Keep container closed when not in use. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 69048-98-2: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
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: Crystals
Color: white
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 78.30 - 79.80 deg C
Autoignition Temperature: 300 deg C ( 572.00 deg F)
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: 500 g/l (20 c)
Specific Gravity/Density:
Molecular Formula: C3H6N4O
Molecular Weight: 114.11

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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:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 69048-98-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-Ethyl-1,4-Dihydro-5H-Tetrazol-5-One - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
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: XN
Risk Phrases:
R 22 Harmful if swallowed.
Safety Phrases:
S 28A After contact with skin, wash immediately with
plenty of water.
S 28B After contact with skin, wash immediately with
plenty of water and soap.
S 37 Wear suitable gloves.
S 38 In case of insufficient ventilation, wear
suitable respiratory equipment.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 69048-98-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 69048-98-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 69048-98-2 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：

  1,2-二溴乙烷 、 1-乙基-1,4-二氢-5H-四唑-5-酮 在 sodium carbonate 作用下， 以 various solvent(s) 为溶剂， 以69.8%的产率得到1-(2-溴乙基)-4-乙基-1,4-二氢-5H-四唑-5-酮
  参考文献：
  名称：

  芬太尼的合成1,4-二取代-1,4-二氢-5H-四唑-5-酮衍生物：alfentanil（R 39209），一种有效的极短效麻醉药。

  摘要：

  描述了芬太尼，芬太尼和舒芬太尼的一系列N-1,4-二取代-1,4-二氢-5H-四唑-5-一个哌啶基衍生物的合成。1-取代的四唑啉酮2基本上是通过叠氮化铝与四氢呋喃中的异氰酸酯或酰氯的加成反应制备的。在中性或弱碱性条件下2的烷基化几乎只能得到1,4-二取代的四唑啉酮异构体3。哌啶衍生物4与3在二甲基甲酰胺中的N-烷基化反应得到9a-v。静脉内注射化合物后，在大鼠尾缩反射试验中评估了大鼠的吗啡活性。芬太尼类似物9a-c（R4 = H）在2.5或10 mg / kg的测定剂量下无活性（iv）。对于甲芬太尼类似物（R4 = COOCH3），当R1代表低级烷基（9d-f）或噻吩基乙基（9n）时，具有最大的麻醉活性。舒芬太尼类似物（R4 = CH2OCH3）显示出与卡芬太尼衍生物（R4 = COOCH3）相同的结构-活性关系（SAR）谱。最佳活动的结构要求与10-12系列中的早期观察结果非常一致。从该

  DOI：

  10.1021/jm00161a027
• 作为产物：
  描述：

  异氰酸乙酯 在 三氯化铝 、 sodium azide 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以65%的产率得到1-乙基-1,4-二氢-5H-四唑-5-酮
  参考文献：
  名称：

  芬太尼的合成1,4-二取代-1,4-二氢-5H-四唑-5-酮衍生物：alfentanil（R 39209），一种有效的极短效麻醉药。

  摘要：

  描述了芬太尼，芬太尼和舒芬太尼的一系列N-1,4-二取代-1,4-二氢-5H-四唑-5-一个哌啶基衍生物的合成。1-取代的四唑啉酮2基本上是通过叠氮化铝与四氢呋喃中的异氰酸酯或酰氯的加成反应制备的。在中性或弱碱性条件下2的烷基化几乎只能得到1,4-二取代的四唑啉酮异构体3。哌啶衍生物4与3在二甲基甲酰胺中的N-烷基化反应得到9a-v。静脉内注射化合物后，在大鼠尾缩反射试验中评估了大鼠的吗啡活性。芬太尼类似物9a-c（R4 = H）在2.5或10 mg / kg的测定剂量下无活性（iv）。对于甲芬太尼类似物（R4 = COOCH3），当R1代表低级烷基（9d-f）或噻吩基乙基（9n）时，具有最大的麻醉活性。舒芬太尼类似物（R4 = CH2OCH3）显示出与卡芬太尼衍生物（R4 = COOCH3）相同的结构-活性关系（SAR）谱。最佳活动的结构要求与10-12系列中的早期观察结果非常一致。从该

  DOI：

  10.1021/jm00161a027

文献信息

• Anti-allergic five membered heterocyclic ring containing N-(bicyclic
  申请人：Janssen Pharmaceutica, N.V.

  公开号：US04634704A1

  公开（公告）日：1987-01-06

  Five membered heterocyclic ring containing N-(bicyclic heterocyclyl)-4-piperidinamines having histamine and serotonine antagonistic activity which compounds are useful agents in the treatment of allergic diseases.

  含有N-(双环杂环基)-4-哌啶胺基的五元杂环环，具有组胺和5-羟色胺拮抗活性的化合物，这些化合物是治疗过敏病的有用药剂。
• A one-pot synthesis of tetrazolones from acid chlorides: understanding functional group compatibility, and application to the late-stage functionalization of marketed drugs
  作者：Matthew A. J. Duncton、Rajinder Singh

  DOI：10.1039/c6ob01644h

  日期：——

  The method could be used for the late-stage functionalization of pharmaceuticals, to provide tetrazolone congeners of the marketed drugs aspirin, indomethacin, probenecid, telmisartan, bexarotene, niacin (vitamin B3), and the active metabolite of the recently-launched immuno-modulatory agent, BG-12 (Tecfidera®). The ability of a tetrazolone group to serve as a bioisostere of a carboxylic acid, and

  提出了使用叠氮基三甲基硅烷从一酰氯一锅且可扩展地合成四唑酮（四唑-5-酮）的方法。该反应可耐受许多官能团，并可以中等至极好的收率（14–94％）提供芳基，杂芳基，烯基或烷基取代的四唑酮产品。当反应规模较大时（20–36 g），未观察到收率降低。该方法可用于药物的后期功能化，以提供市售药物阿司匹林，消炎痛，丙磺舒，替米沙坦，倍沙罗汀，烟酸（维生素B3）以及最近推出的免疫调节剂的活性代谢产物的四唑酮同类物。剂，BG-12（Tecfidera ®）。还强调了四唑酮基团用作羧酸的生物等排体和改善药物药代动力学特征的能力。
• Tetrazolones as a Carboxylic Acid Bioisosteres
  申请人：RIGEL PHARMACEUTICALS, INC.

  公开号：US20160213648A1

  公开（公告）日：2016-07-28

  The present disclosure provides compounds that include a tetrazolone derivative of a carboxyl group of an active agent. This disclosure also relates to pharmaceutical compositions that include these compounds, methods of using these compounds in the treatment of various diseases and disorders, and processes for preparing these compounds.

  本公开提供了包括活性剂羧基的四唑酮衍生物的化合物。本公开还涉及包括这些化合物的药物组合物，使用这些化合物治疗各种疾病和疾病的方法，以及制备这些化合物的过程。
• SUBSTITUTED 4-AMINO-PIPERIDINES
  申请人：Gant Thomas G.

  公开号：US20100016365A1

  公开（公告）日：2010-01-21

  The present invention relates to new substituted 4-amino-piperidine opioid receptor modulators, pharmaceutical compositions thereof, and methods of use thereof.

  本发明涉及新的取代4-氨基哌啶类阿片受体调节剂，其药物组成物以及使用方法。
• N-phenyl-N-(4-piperidinyl)amides
  申请人：Janssen Pharmaceutica, N.V.

  公开号：US04167574A1

  公开（公告）日：1979-09-11

  Novel compounds of the series of N-phenyl-N-(4-piperidinyl)amides having a (4,5-dihydro-4-R-5-oxo-1H-tetrazol-1-yl)alkyl or (4,5-dihydro-4-R-5-thioxo-1H-tetrazol-1-yl)alkyl substituent group in the 1-position of the piperidine nucleus, said compounds being useful as analgesic agents.

  该系列新化合物为N-苯基-N-(4-哌啶基)酰胺，其在哌啶环的1位具有(4,5-二氢-4-R-5-氧代-1H-四唑-1-基)烷基或(4,5-二氢-4-R-5-硫代-1H-四唑-1-基)烷基取代基团，这些化合物可用作镇痛剂。