2-氨基-3-溴-5-三氟甲基吡啶 | 79456-30-7

• 物质功能分类: 医药中间体 - 吡啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-氨基-3-溴-5-三氟甲基吡啶
• 中文别名: 2-氨基-3-溴-5-(三氟甲基)吡啶；3-溴-2-氨基-5-(三氟甲基)吡啶
• 英文名称: 3-bromo-5-(trifluoromethyl)pyridin-2-amine
• 英文别名: 2-amino-3-bromo-5-trifluoromethylpyridine
• CAS: 79456-30-7
• 化学式: C₆H₄BrF₃N₂
• mdl: MFCD07375382
• 分子量: 241.01
• InChiKey: KBNACDZKKVMULE-UHFFFAOYSA-N

物化性质

• 熔点：
  98-101℃
• 沸点：
  221.7±40.0 °C(Predicted)
• 密度：
  1.790±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  38.9
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933399090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302+H312+H332,H315,H319,H335
• 储存条件：
  室温条件下。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Amino-3-bromo-5-trifluoromethylpyridine
Synonyms: 3-Bromo-5-(trifluoromethyl)pyridin-2-amine

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H302: Harmful if swallowed
H312: Harmful in contact with skin
H332: Harmful if inhaled
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
Ingredient name: 2-Amino-3-bromo-5-trifluoromethylpyridine
CAS number: 79456-30-7

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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.
Storage: Store in closed vessels.

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C6H4BrF3N2
Molecular weight: 241.0

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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, hydrogen fluoride, hydrogen bromide.

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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-氨基-3-溴-5-三氟甲基吡啶 在 盐酸 、 四氧化锇 、 四(三苯基膦)钯 、 N-甲基吲哚酮 、 碳酸氢钠 、 sodium nitrite 、 三氯氧磷 作用下， 以 乙醇 、 水 、 丙酮 、 叔丁醇 、 苯 为溶剂， 生成 2-chloro-3-(4-methylsulfonyl)phenyl-5-trifluoromethyl-pyridine
  参考文献：
  名称：

  2-Heterosubstituted-3-(4-methylsulfonyl)phenyl-5-trifluoromethyl pyridines as selective and orally active cyclooxygenase-2 inhibitors

  摘要：

  A series of novel 2-alkoxy, 2-thioalkoxy and 2-amino-3-(4-methylsulfonyl)phenylpyridines has been synthesized and shown to be highly potent and selective cyclooxygenase-2 (COX-2) inhibitors. Structure-activity relationship studies have demonstrated that central pyridine ring substituents play an important role in the COX-2 potency, selectivity vs the COX-1 enzyme, and oral activity. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00264-4
• 作为产物：
  描述：

  2-氨基-5-三氟甲基吡啶 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以94.17%的产率得到2-氨基-3-溴-5-三氟甲基吡啶
  参考文献：
  名称：

  [EN] HETEROCYCLIC COMPOUNDS AND THEIR USE FOR TREATMENT OF HELMINTHIC INFECTIONS AND DISEASES
  [FR] COMPOSÉS HÉTÉROCYCLIQUES ET LEUR UTILISATION POUR LE TRAITEMENT D'INFECTIONS ET DE MALADIES HELMINTHIQUES

  摘要：

  本文提供了式（I）的杂环化合物及其药学上可接受的盐、互变异构体、同位素同分异构体或立体异构体，其中W、X、Y、R1、R2和RN如本文所定义，包括有效量的杂环化合物的组合物，以及治疗或预防动物和人类丝虫感染和疾病的方法。

  公开号：

  WO2020219871A1

文献信息

• [EN] AZEPANYL-DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME WITH ANTIPARASITIC ACTIVITY<br/>[FR] DÉRIVÉS D'AZÉPANYLE ET COMPOSITIONS PHARMACEUTIQUES À ACTIVITÉ ANTI-PARASITAIRE LES CONTENANT
  申请人：MERCK PATENT GMBH

  公开号：WO2016000827A1

  公开（公告）日：2016-01-07

  The present invention provides compounds of Formula (i). Furthermore, pharmaceutical compositions are provided comprising at least one compound of Formula (i), for the treatment of parasitic diseases including malaria, as well as neurodegenerative diseases.

  本发明提供了化合物的结构式（i）。此外，提供了包含至少一种结构式（i）化合物的药物组合物，用于治疗包括疟疾在内的寄生虫病以及神经退行性疾病。
• Antikinetoplastid SAR study in 3-nitroimidazopyridine series: Identification of a novel non-genotoxic and potent anti-T. b. brucei hit-compound with improved pharmacokinetic properties
  作者：Cyril Fersing、Clotilde Boudot、Romain Paoli-Lombardo、Nicolas Primas、Emilie Pinault、Sébastien Hutter、Caroline Castera-Ducros、Youssef Kabri、Julien Pedron、Sandra Bourgeade-Delmas、Alix Sournia-Saquet、Jean-Luc Stigliani、Alexis Valentin、Amaya Azqueta、Damián Muruzabal、Alexandre Destere、Susan Wyllie、Alan H. Fairlamb、Sophie Corvaisier、Marc Since、Aurélie Malzert-Fréon、Carole Di Giorgio、Pascal Rathelot、Nadine Azas、Bertrand Courtioux、Patrice Vanelle、Pierre Verhaeghe

  DOI：10.1016/j.ejmech.2020.112668

  日期：2020.11

  synthesized compounds allowed improvement in antileishmanial activity, compared to previous hit molecules in the series. Nevertheless, compound 8, the best antitrypanosomal molecule in this series (EC50 = 17 nM, SI = 2650 & E° = −0.6 V), was not only more active than all reference drugs and previous hit molecules in the series but also displayed improved aqueous solubility and better in vitro pharmacokinetic

  为了研究抗运动型3-硝基咪唑并[1,2- a ]吡啶的药效团，通过合成26种原始衍生物并对其在利什曼原虫和布鲁氏锥虫中的体外评价进行了结构-活性关系研究。这项SAR研究表明，抗锥虫药效团比抗疟药药团的限制性更小，并突出显示了咪唑并吡啶环的2、6和8位为关键调节点。与该系列中以前的命中分子相比，没有一种合成的化合物能提高抗疟疾活性。不过，化合物8是该系列中最好的抗胰锥虫分子（EC 50 = 17 nM，SI = 2650＆E°= -0.6 V），不仅比所有参考药物和该系列中以前的命中分子更有活性，而且还表现出改善的水溶性和更好的体外药代动力学特性：良好的微粒体稳定性（T 1/2  > 40分钟），根据PAMPA分析的中等白蛋白结合率（77％）和穿过血脑屏障的中等渗透率。此外，微核和彗星试验均表明硝基芳香分子8在体外没有遗传毒性。证明了分子8的生物活化是由T.b.进行的。布氏1型硝基还原酶，以
• Transition metal-free direct C H trifluoromethyltion of (hetero)arenes with Togni’s reagent
  作者：Xiaoyu Chen、Licheng Ding、Linlin Li、Jingya Li、Dapeng Zou、Yangjie Wu、Yusheng Wu

  DOI：10.1016/j.tetlet.2019.151538

  日期：2020.2

  A new transition-metal-free direct C−H trifluoromethylation reaction of (hetero)arenes with Togni’s reagent was developed. This transformation proceeded smoothly under mild conditions and exhibited good tolerance of many synthetically relevant functional groups. It provided an alternative approach for the synthesis of trifluoromethylated (hetero)arenes.

  开发了一种新的无杂芳烃与Togni's试剂的无过渡金属直接C-H三氟甲基化反应。该转化在温和条件下平稳进行，并且表现出对许多合成相关官能团的良好耐受性。它为合成三氟甲基化（杂）芳烃提供了另一种方法。
• Asymmetric Hydrogenation of Azaindoles: Chemo‐ and Enantioselective Reduction of Fused Aromatic Ring Systems Consisting of Two Heteroarenes
  作者：Yusuke Makida、Masahiro Saita、Takahiro Kuramoto、Kentaro Ishizuka、Ryoichi Kuwano

  DOI：10.1002/anie.201606083

  日期：2016.9.19

  by using the chiral catalyst, which was prepared from [Ru(η3‐methallyl)2(cod)] and a trans‐chelating bis(phosphine) ligand (PhTRAP). The dearomative reaction exclusively occurred on the five‐membered ring, thus giving the corresponding azaindolines with up to 97:3 enantiomer ratio.

  高对映选择性通过使用手性催化剂，将其从的[Ru（η制备的氮杂吲哚的氢化实现3 -methallyl）2（COD）]和反式-chelating双（膦）配体（PhTRAP）。脱芳香反应只发生在五元环上，因此相应的氮杂吲哚啉对映体比率高达97：3。
• [EN] GAMMA SECRETASE MODULATERS<br/>[FR] MODULATEURS DE GAMMA-SECRÉTASE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2011092272A1

  公开（公告）日：2011-08-04

  The invention relates to compounds of formula ( I ) wherein R1/R1' are independently from each other hydrogen, halogen, lower alkoxy or cyano; R2 is lower alkyl, halogen, lower alkoxy, lower alkyl substituted by halogen, lower alkoxy substituted by halogen, lower alkyl substituted by OR, =0, -C(O)O-lower alkyl, -C(O)NH-lower alkyl, cyano, CH2-O-lower alkyl, cycloalkyl, NRR'or is -O-(CH2)o-phenyl optionally substituted by halogen, or is -(CH2)o-phenyl optionally substituted by one, two or three substituents, selected from halogen, -(CH2)o-cyano, lower alkyl, lower alkyl substituted by halogen, lower alkyl substituted by hydroxy, C(O)H, -CH2-NH2-, -CH2-NH-C(O)O-lower alkyl, -CH2-NH-C(O)-lower alkyl, -CH2-NH-lower alkyl, -CH2-NH-S(O)2-lower alkyl, lower alkoxy or by lower alkoxy substituted by halogen, or is -(CH2)o-cycloalkyl, or is -(CH2)o-heterocycloalkyl which is optionally substituted by halogen, CF3, lower alkyl, -CH2CN, -C(O)-lower alkyl, -C(O)O-lower alkyl or S(O)2-lower alkyl, or is heteroaryl selected from the group consisting of furanyl, pyrazinyl, pyridinyl, benzooxazolyl or benzoimidazolyl which are optionally substituted by lower alkyl, or is 4-methyl-3,4-dihydro-2H-benzo[l,4]oxazine R and R' are independently from each other hydrogen or lower alkyl, and o is 0 or 1; R3 may occur once or twice and is lower alkyl; A is Formula a), b), c), d), e), f), h), i), j) and Formula k); R2' is hydrogen, lower alkyl, lower alkyl substituted by halogen, C(O)-lower alkyl, S(O)2-lower alkyl or phenyl optionally substituted by halogen; hetaryl is a 5 or 6 membered N, S or O-containing heteroaryl group; n is O, 1, 2 or 3; if n is 2 or 3, R2 may be the same or not; or to pharmaceutically active acid addition salts thereof. The present compounds of formula ( I ) are modulators for amyloid beta and thus, they may be useful for the treatment or prevention of a disease associated with the deposition of β-amyloid in the brain, in particular Alzheimer's disease, and other diseases such as cerebral amyloid angiopathy, hereditary cerebral hemorrhage with amyloidosis, Dutch-type (HCHWA-D), multi- infarct dementia, dementia pugilistica and Down syndrome.

  该发明涉及以下式（I）的化合物，其中R1/R1'分别独立地为氢、卤素、较低的烷氧基或氰基；R2为较低的烷基、卤素、较低的烷氧基、卤素取代的较低烷基、卤素取代的较低烷氧基、取代的较低烷基OR、=0、-C(O)O-较低烷基、-C(O)NH-较低烷基、氰基、CH2-O-较低烷基、环烷基、NRR'或为-O-( )o-苯基，可选择地取代为卤素，或为-( )o-苯基，可选择地取代为一个、两个或三个取代基，选自卤素、-( )o-氰基、较低烷基、卤素取代的较低烷基、羟基取代的较低烷基、C(O)H、- -NH2-、- -NH-C(O)O-较低烷基、- -NH-C(O)-较低烷基、- -NH-较低烷基、- -NH-S(O)2-较低烷基、较低烷氧基或取代的较低烷氧基，或为-( )o-环烷基，或为-( )o-杂环烷基，可选择地取代为卤素、CF3、较低烷基、- CN、-C(O)-较低烷基、-C(O)O-较低烷基或S(O)2-较低烷基，或为杂芳基，选自呋喃基、吡嗪基、吡啶基、苯并噁唑基或苯并咪唑基，可选择地取代为较低烷基，或为4-甲基-3,4-二氢-2H-苯并[l,4]噁啉，R和R'分别独立地为氢或较低烷基，o为0或1；R3可能出现一次或两次，为较低烷基；A为式a)、b)、c)、d)、e)、f)、h)、i)、j)和式k)；R2'为氢、较低烷基、卤素取代的较低烷基、C(O)-较低烷基、S(O)2-较低烷基或可选择地取代为卤素的苯基；hetaryl为5或6成员的含氮、硫或氧的杂芳基；n为O、1、2或3；如果n为2或3，R2可能相同也可能不同；或其药用活性酸盐。该式（I）的化合物是淀粉样蛋白β的调节剂，因此，它们可能对与大脑中β-淀粉样蛋白沉积相关的疾病的治疗或预防有用，特别是阿尔茨海默病，以及其他疾病，如脑淀粉样血管病、遗传性淀粉样脑出血症，荷兰型（HCHWA-D），多梗死性痴呆、拳击性痴呆和唐氏综合征。