2-氨基-4-三氟甲基嘧啶-5-羧酸乙酯 | 149771-09-5

• 物质功能分类: 医药中间体 - 杂环化合物 - 嘧啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 2-氨基-4-三氟甲基嘧啶-5-羧酸乙酯
• 中文别名: 2-氨基-4-(三氟甲基)嘧啶-5-甲酸乙酯
• 英文名称: ethyl 2-amino-4-(trifluoromethyl)pyrimidine-5-carboxylate
• 英文别名: 2-amino-4-trifluoromethyl-pyrimidine-5-carboxylic acid ethyl ester
• CAS: 149771-09-5
• 化学式: C₈H₈F₃N₃O₂
• mdl: MFCD00052070
• 分子量: 235.166
• InChiKey: OUACXMUEZBQRBJ-UHFFFAOYSA-N

物化性质

• 熔点：
  179 °C
• 沸点：
  366.7±52.0 °C(Predicted)
• 密度：
  1.416±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  78.1
• 氢给体数：
  1
• 氢受体数：
  8

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2933599090
• 危险类别：
  IRRITANT
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温

SDS

Name:	Ethyl 2-amino-4-(trifluoromethyl)pyrimidine-5-carboxylate 97% Material Safety Data Sheet
Synonym:
CAS:	149771-09-5

Section 1 - Chemical Product MSDS Name:Ethyl 2-amino-4-(trifluoromethyl)pyrimidine-5-carboxylate 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
149771-09-5	Ethyl 2-amino-4-(trifluoromethyl)pyrim	97%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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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.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
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:
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.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 149771-09-5: Personal Protective Equipment Eyes: Not available.
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: Solid
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 179 - 180 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C8H8F3N3O2
Molecular Weight: 235

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents, acid chlorides.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, fluorine, hydrogen fluoride gas.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 149771-09-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Ethyl 2-amino-4-(trifluoromethyl)pyrimidine-5-carboxylate - 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
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 149771-09-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 149771-09-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 149771-09-5 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：

  2-氨基-4-三氟甲基嘧啶-5-羧酸乙酯 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 11.0h， 生成 4-三氟甲基-2-氨基嘧啶
  参考文献：
  名称：

  Sansebastiano; Mosti; Menozzi, Il Farmaco, 1993, vol. 48, # 3, p. 335 - 355

  摘要：

  DOI：
• 作为产物：
  描述：

  2-羟基-4-三氟甲基嘧啶-5-羧酸乙酯 在 氨 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 生成 2-氨基-4-三氟甲基嘧啶-5-羧酸乙酯
  参考文献：
  名称：

  Structure–Activity Relationship Studies of Ethyl 2-[(3-Methyl-2,5-dioxo(3-pyrrolinyl))amino]-4-(trifluoromethyl)pyrimidine-5-carboxylate: An Inhibitor of AP-1 and NF-κB Mediated Gene Expression

  摘要：

  Several analogues of ethyl 2-[(3-methyl-2,5-dioxo(3-pyrrolinyl))amino]-4-(trifluoromethyl)pyrimidine-5-carboxylate (1) were synthesized and tested as inhibitors of AP-1 and NF-kappaB mediated transcriptional activation in Jurkat T cells. From our SAR work, ethyl 2-[(3-methyl-2,5-dioxo(3-pyrrolinyl))-N-methylamino]-4-(trifluoromethyl)-pyrimidine-5-carboxylate was identified as a novel and potent inhibitor. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00517-6

文献信息

• [EN] cGAS ANTAGONIST COMPOUNDS<br/>[FR] COMPOSÉS ANTAGONISTES DU CGAS
  申请人：IMMUNE SENSOR LLC

  公开号：WO2017176812A1

  公开（公告）日：2017-10-12

  Disclosed are novel compounds of Formula (I) that are cGAS antagonists, methods of preparation of the compounds, pharmaceutical compositions comprising the compounds, and their use in medical therapy.

  揭示了一种新型化合物的化学式（I），这些化合物是cGAS拮抗剂，涉及到这些化合物的制备方法、包含这些化合物的药物组合物，以及它们在医学治疗中的应用。
• IMIDAZOPYRIDINE AND IMIDAZOPYRIMIDINE DERIVATIVES
  申请人：Araldi Gian-Luca

  公开号：US20080058350A1

  公开（公告）日：2008-03-06

  The present invention relates to imidazopyridine and imidazopyrimidine derivatives that act as cannabinoid receptor ligands, e.g., CB2 ligands. The invention also relates to methods of preparing the compounds, compositions containing the compounds, and to methods of treatment using the compounds.

  本发明涉及作为大麻素受体配体（例如CB2配体）的咪唑吡啶和咪唑吡啶衍生物。该发明还涉及制备这些化合物的方法、含有这些化合物的组合物，以及使用这些化合物进行治疗的方法。
• [EN] PYRIMIDINE DERIVATIVES AS CANNABINOID RECEPTOR MODULATORS<br/>[FR] DERIVES DE PYRIMIDINE UTILISES COMME MODULATEURS DES RECEPTEURS CANNABINOIDES
  申请人：GLAXO GROUP LTD

  公开号：WO2005080350A1

  公开（公告）日：2005-09-01

  The present invention relates to novel pyrimidine derivatives such as compounds of the formula (I) and the use of such compounds or pharmaceutical compositions thereof in the treatment of diseases, particularly pain, which are mediated by the activity of the cannabinoid 2 receptor.

  本发明涉及新型嘧啶衍生物，如式(I)化合物及其在治疗疾病中的应用，特别是通过大麻素2受体活性介导的疼痛。
• The reactions of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole as a way to novel azaheterocycles
  作者：Marina V Goryaeva、Yanina V Burgart、Marina A Ezhikova、Mikhail I Kodess、Viktor I Saloutin

  DOI：10.3762/bjoc.11.44

  日期：——

  The interaction of 2-ethoxymethylidene-3-oxo esters and their analogues with 5-aminotetrazole is an efficient synthetic approach to novel azaheterocycles. 2-Ethoxymethylidene-3-oxo esters bearing alkyl substituents react with 5-aminotetrazole to form ethyl 2-azido-4-alkylpyrimidine-5-carboxylates which are capable of subsequent nucleophilic substitution. The use of diethyl 2-ethoxymethylidenemalonate in this reaction resulted in ethyl 7-hydroxytetrazolo[1,5-a]pyrimidine-6-carboxylate, while ethyl 2-ethoxymethylidenecyanoacetate yielded 5-[2,6-diamino-3,5-bis(ethoxycarbonyl)pyridinium-1-yl]tetrazol-1-ide through an alternative pathway. Ethyl 2-benzoyl-3-ethoxyprop-2-enoate reacted with 5-aminotetrazole by two reaction routes to form ethyl 2-benzoyl-3-(1H-tetrazol-5-ylamino)prop-2-enoate and ethyl 7-(1-ethoxy-1,3-dioxo-3-phenylpropan-2-yl)-5-phenyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate.

  2-乙氧甲基亚甲基-3-酮基酯及其类似物与5-氨基四唑的相互作用是一种有效的合成新型氮杂环化合物的方法。带有烷基取代基的2-乙氧甲基亚甲基-3-酮基酯与5-氨基四唑反应，形成乙酰基2-氮杂嘧啶-5-羧酸酯，这些化合物能够进行进一步的亲核取代反应。在此反应中使用二乙酰乙二酯，可以得到乙酰基7-羟基四唑并环[1,5-a]嘧啶-6-羧酸乙酯，而使用乙酸乙酯基2-乙氧甲基亚甲基丙烯酸酯，则通过另一种途径生成5-[2,6-二氨基-3,5-双(乙氧羰基)吡啶-1-基]四唑-1-化物。乙酰基2-苯甲酰基-3-乙氧基丙烯酸酯通过两种反应途径与5-氨基四唑反应，形成乙酰基2-苯甲酰基-3-(1H-四唑-5-基)丙烯酸酯和乙酯基7-(1-乙氧基-1,3-二氧杂环戊烷-3-苯基丙基)-5-苯基-4,7-二氢四唑并环[1,5-a]嘧啶-6-羧酸乙酯。
• Traceless linker: Oxidative activation and displacement of a sulfur-based linker
  作者：Leah M. Gayo、Mark J. Suto

  DOI：10.1016/s0040-4039(96)02256-3

  日期：1997.1

  construction of small heterocycles using solid-phase chemistry is usually done through the use of a polar group to attach the compounds to the resin. These polar functionalities invariably become part of the structure and eventually limit the structure-activity relationships derived from these compounds. We have identified a method for overcoming some of these limitations. A sulfur-based linker has been

  使用固相化学方法构建小的杂环通常是通过使用极性基团将化合物连接到树脂上来完成的。这些极性官能团始终成为结构的一部分，并最终限制了衍生自这些化合物的构效关系。我们已经找到一种克服这些局限性的方法。已经鉴定出基于硫的连接基，其不仅可以用作小杂环的连接点，而且还可以用作将进一步的多样性引入分子的手段。接头保持惰性，直到被氧化“激活”为止。然后可以使用有限量的亲核试剂从树脂上裂解该分子并将另外的多样性引入该分子中。