(S)-2-氨基-4,4,4-三氟丁酸 | 15960-05-1

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (S)-2-氨基-4,4,4-三氟丁酸
• 中文别名: 2-氨基-4,4,4-三氟丁酸
• 英文名称: (S)-2-amino-4,4,4-trifluorobutanoic acid
• 英文别名: (2S)-2-amino-4,4,4-trifluorobutanoic acid
• CAS: 15960-05-1
• 化学式: C₄H₆F₃NO₂
• 分子量: 157.092
• InChiKey: AQPCXCOPDSEKQT-REOHCLBHSA-N

物化性质

• 熔点：
  260-265°C
• 密度：
  1.3293 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P362,P403+P233,P501
• 危险性描述：
  H315,H319,H335

SDS

Name:	2-Amino-4 4 4-trifluorobutyric acid Material Safety Data Sheet
Synonym:	3-Trifluoromethylalanin
CAS:	15960-05-1

Section 1 - Chemical Product MSDS Name:2-Amino-4 4 4-trifluorobutyric acid Material Safety Data Sheet
Synonym:3-Trifluoromethylalanin

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
15960-05-1	2-Amino-4,4,4-trifluorobutyric acid	100.0	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.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
Causes 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.
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.
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:
Antidote: None reported.

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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. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation. Use only in a chemical fume hood.
Storage:
Store in a tightly closed container. 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# 15960-05-1: 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: Solid
Color: Not available.
Odor: No apparent odor.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 256 deg C dec
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: C4H6F3NO2
Molecular Weight: 157.09

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stability unknown.
Conditions to Avoid:
Incompatible materials, dust generation.
Incompatibilities with Other Materials:
Strong acids, strong bases, strong oxidizing agents, strong reducing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, hydrogen fluoride gas.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 15960-05-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Amino-4,4,4-trifluorobutyric acid - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION
Other No information available.

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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: 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# 15960-05-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 15960-05-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 15960-05-1 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：

  (S)-2-氨基-4,4,4-三氟丁酸 、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 edetate disodium 、 sodium carbonate 作用下， 以 水 、 乙腈 为溶剂， 反应 4.0h， 生成 (2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-4,4,4-trifluorobutanoic acid
  参考文献：
  名称：

  通过手性亲核甘氨酸等效物的烷基化反应，方便地不对称合成（S）-2-氨基-4,4,4-三氟丁酸

  摘要：

  在此，我们公开了在> 10 g规模的目标产物上进行对映异构体，对映异构体为97.8％ee的（S）-2-氨基-4,4,4-三氟丁酸的纯N -Fmoc衍生物的不对称合成。该方法基于在环境温度下进行的新一代手性亲核等效物的烷基化（CF 3 -CH 2 -I），具有出色的立体化学结果。开发的方案不需要任何色谱分离，并且仅包括通过最终产物的重结晶进行的一个纯化步骤。

  DOI：

  10.1021/acs.oprd.8b00404
• 作为产物：
  描述：

  2-乙酰胺基-4,4,4-三氟乙酸 以97%的产率得到(S)-2-氨基-4,4,4-三氟丁酸
  参考文献：
  名称：

  含氟氨基酸及其衍生物。7.α和γ取代的甲氨蝶呤类似物1的合成及其抗肿瘤活性

  摘要：

  α-取代的丙二酸酯的三种类型的反应，二氟甲基化，与n，n，n-三氟烷基磺酸酯的烷基化以及与2-取代的丙烯酸酯的Michael加成反应，可方便地得到许多含氟的α氨基酸，​​例如β-氟代丙氨酸。 ，2-氨基-n，n，n-三氟链烷酸和氟化谷氨酸以及其他γ-杂原子取代的谷氨酸。在此，进行了使用猪肾酰基转移酶的有效酶促光学拆分，以获得2-氨基-n，n，n-三氟链烷酸的两种旋光异构体。另外，在α-二氟甲基-α-亚磺酰丙二酸二乙酯的碱催化反应中观察到了新的亚砜重排。最后，获得的α-和γ-取代的谷氨酸用于抗肿瘤药甲氨蝶呤的化学修饰，以显示出显着的构效关系。特别是，氟取代对观察到体内抗肿瘤活性。

  DOI：

  10.1016/s0040-4020(01)86044-0

文献信息

• MODULATORS OF SESTRIN-GATOR2 INTERACTION AND USES THEREOF
  申请人：Navitor Pharmaceuticals, Inc.

  公开号：US20170114080A1

  公开（公告）日：2017-04-27

  The present invention provides compounds, compositions thereof, and methods of using the same.

  本发明提供了化合物、其组合物以及使用相同的方法。
• [EN] MODULATORS OF SESTRIN-GATOR2 INTERACTION AND USES THEREOF<br/>[FR] MODULATEURS DE L'INTERACTION SESTRINE-GATOR2 ET UTILISATIONS DE CES DERNIERS
  申请人：NAVITOR PHARM INC

  公开号：WO2018200625A1

  公开（公告）日：2018-11-01

  The present invention provides compounds, compositions thereof, and methods of using the same.

  本发明提供了化合物、其组合物以及使用相同的方法。
• Fluorine containing amino acids and their derivatives. 7. Synthesis and antitumor activity of α- and γ-substituted methotrexate analogs
  作者：Tadahiko Tsushima、Kenji Kawada、Shoichi Ishihara、Naomi Uchida、Osamu Shiratori、Junko Higaki、Masaharu Hirata

  DOI：10.1016/s0040-4020(01)86044-0

  日期：1988.1

  afforded a number of fluorine containing α amino acids such as β-fluorinated-alanines, 2-amino-n,n,n-trifluoroalkanoic acids, and fluorinated glutamic acids as well as other γ-heteroatom substituted glutamic acids. Here, an efficient enzymatic optical resolution using hog kidney acylase was conducted to obtain both optical isomers of 2-amino-n,n,n-trifluoroalkanoic acids. In addition, a novel sulfoxide

  α-取代的丙二酸酯的三种类型的反应，二氟甲基化，与n，n，n-三氟烷基磺酸酯的烷基化以及与2-取代的丙烯酸酯的Michael加成反应，可方便地得到许多含氟的α氨基酸，​​例如β-氟代丙氨酸。 ，2-氨基-n，n，n-三氟链烷酸和氟化谷氨酸以及其他γ-杂原子取代的谷氨酸。在此，进行了使用猪肾酰基转移酶的有效酶促光学拆分，以获得2-氨基-n，n，n-三氟链烷酸的两种旋光异构体。另外，在α-二氟甲基-α-亚磺酰丙二酸二乙酯的碱催化反应中观察到了新的亚砜重排。最后，获得的α-和γ-取代的谷氨酸用于抗肿瘤药甲氨蝶呤的化学修饰，以显示出显着的构效关系。特别是，氟取代对观察到体内抗肿瘤活性。
• Chemical aminoacylation of tRNAs with fluorinated amino acids for in vitro protein mutagenesis
  作者：Shijie Ye、Allison Ann Berger、Dominique Petzold、Oliver Reimann、Benjamin Matt、Beate Koksch

  DOI：10.3762/bjoc.6.40

  日期：——

  This article describes the chemical aminoacylation of the yeast phenylalanine suppressor tRNA with a series of amino acids bearing fluorinated side chains via the hybrid dinucleotide pdCpA and ligation to the corresponding truncated tRNA species. Aminoacyl-tRNAs can be used to synthesize biologically relevant proteins which contain fluorinated amino acids at specific sites by means of a cell-free translation system. Such engineered proteins are expected to contribute to our understanding of discrete fluorines’ interaction with canonical amino acids in a native protein environment and to enable the design of fluorinated proteins with arbitrary desired properties.

  本文描述了使用含有氟代侧链的一系列氨基酸通过杂交二核苷酸pdCpA化学氨酰化酵母苯丙氨酸抑制子tRNA，并与相应的截短tRNA物种连接。氨酰-tRNA可以用于通过无细胞翻译系统在特定位点合成含有氟代氨基酸的生物学相关蛋白质。这种工程蛋白质有望为我们了解离散氟元素在天然蛋白质环境中与基本氨基酸的相互作用以及设计具有任意所需特性的氟化蛋白质做出贡献。
• HCV NS3 PROTEASE INHIBITORS
  申请人：HOLLOWAY M. Katharine

  公开号：US20090124661A1

  公开（公告）日：2009-05-14

  The present invention relates to macrocyclic compounds of formula (I) that are useful as inhibitors of the hepatitis C virus (HCV) NS3 protease, their synthesis, and their use for treating or preventing HCV infections.

  本发明涉及公式（I）的大环化合物，其可用作丙型肝炎病毒（HCV）NS3蛋白酶的抑制剂，其合成以及用于治疗或预防HCV感染的用途。