2,5-二氯苯乙胺 | 56133-86-9

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,5-二氯苯乙胺
• 中文别名: 3-溴-2-氯三氟甲苯
• 英文名称: 2-(2,5-dichlorophenyl)ethan-1-amine
• 英文别名: 2,5-Dichlorophenethylamine；2-(2,5-dichlorophenyl)ethanamine
• CAS: 56133-86-9
• 化学式: C₈H₉Cl₂N
• mdl: MFCD04114077
• 分子量: 190.072
• InChiKey: KSKAHYBZLQUACF-UHFFFAOYSA-N

物化性质

• 沸点：
  132-134 °C(Press: 10 Torr)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2921499090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2,5-Dichlorophenethylamine
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: 2,5-Dichlorophenethylamine
CAS number: 56133-86-9

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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: C8H9Cl2N
Molecular weight: 190.1

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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, hydrogen chloride.

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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

制备方法与用途

制备2,5-二氯苯乙胺的过程如下：在0℃下，向2-(2,5-二氯苯基)乙腈（34.5g，185mmol）的MeOH（1700mL）溶液中加入NiCl₂·6H₂O（4.45g，18.7mmol）。10分钟后，初始绿色悬浮液中的固体逐渐溶解。随后，在10分钟内通过注射器加入氯甲酸甲酯（38.4g，406mmol），然后在0℃下于30分钟内分8小份逐步加入NaBH₄（41.4g，1.09mol）。观察到气体的产生，并且反应混合物逐渐变黑。完成加料后，所得混合物在20℃下搅拌1小时。LCMS分析显示，产物的产率为48%，而2,5-二氯苯乙胺的总收率为32%。

2,5-二氯苯乙胺可用作医药合成中的中间体。

反应信息

• 作为反应物：
  描述：

  2,5-二氯苯乙胺 在 5,5'-双(二苯基磷)-四氟-二-1,3-苯二氧杂环 、 4-二甲氨基吡啶 、 [Ir(cod)₂]OTf 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 26.0h， 生成
  参考文献：
  名称：

  铱催化降冰片烯衍生物的不对称加氢烯基化

  摘要：

  过渡金属催化的烯烃不对称加氢烯基化提供了一种原子经济的方法，可以从容易获得的材料中构建分子复杂性。在此，我们报告了铱催化的非共轭烯烃与丙烯酰胺和丙烯酸酯的不对称加氢烯基化反应。降冰片烯衍生物的催化加氢烯基化反应形成了具有高化学选择性、区域选择性和立体选择性的烯丙基立体中心产物。DFT 计算表明迁移插入是不可逆的，并且是对映测定步骤。

  DOI：

  10.1021/acs.organomet.0c00811
• 作为产物：
  描述：

  2,5-二氯苯乙腈 、 氯甲酸甲酯 在 sodium tetrahydroborate 、 nickel(II) chloride hexahydrate 作用下， 以 甲醇 为溶剂， 反应 1.67h， 以32%的产率得到2,5-二氯苯乙胺
  参考文献：
  名称：

  一类新型的Zeste Homolog 2（EZH2）抑制剂增强剂含吡啶酮的3,4-二氢异喹啉-1（2 H）-ones的设计与合成

  摘要：

  设计了一种新的zeste同源物2（EZH2）抑制剂增强剂，该增强剂包括通过酰胺键与二甲基吡啶酮部分连接的取代苯环。通过计算分析，确定了改善该化合物结合性能的优先酰胺扭转。酰胺连接基的环化产生六元内酰胺类似物化合物18。相对于其无环类似物，这种转化显着提高了环化化合物的配体效率/效力。含内酰胺的EZH2抑制剂的其他优化工作着眼于亲脂效率（LipE）的改善，从而提供了化合物31。化合物31相对于化合物18，在生化和细胞读数方面均显示出改善的LipE和靶标效价。抑制剂31还显示出强大的体内抗肿瘤生长活性和EZH2靶基因的剂量依赖性去阻遏作用。

  DOI：

  10.1021/acs.jmedchem.6b00515

文献信息

• [EN] GUANIDINE COMPOUNDS AND USE THEREOF<br/>[FR] COMPOSÉS DE GUANIDINE ET LEUR UTILISATION
  申请人：HANALL BIOPHARMA CO LTD

  公开号：WO2015160220A1

  公开（公告）日：2015-10-22

  The present invention relates to guanidine compounds for inhibiting mitochondrial oxidative phosphorylation (OXPHOS) and use thereof. More specifically, the present invention relates to a pharmaceutical composition for preventing or treating a OXPHOS-related disease, particularly cancer by inhibiting mitochondrial oxidative phosphorylation and reprogramming cellular metabolism.

  本发明涉及用于抑制线粒体氧化磷酸化（OXPHOS）的胍啉化合物及其使用。更具体地，本发明涉及一种用于预防或治疗与OXPHOS相关的疾病，特别是通过抑制线粒体氧化磷酸化和重编程细胞代谢的药物组合物。
• MONOAMIDE DERIVATIVES AS OREXIN RECEPTOR ANTAGONISTS
  申请人：Knust Henner

  公开号：US20090036422A1

  公开（公告）日：2009-02-05

  The present invention relates to compounds of formula wherein Ar, R 1 , R 2 , R 3 , R 4 , R 5 , n, o, and p are as defined herein or to pharmaceutically suitable acid addition salts, optically pure enantiomers, racemates or diastereomeric mixtures thereof. The compounds of formula I can be used for the treatment of sleep disorders, such as sleep apnea, narcolepsy, insomnia, parasomnia, jet lag syndrome, circadian rhythms disorder or sleep disorders associated with neurological diseases.

  本发明涉及以下式的化合物 其中 Ar，R 1 ，R 2 ，R 3 ，R 4 ，R 5 ，n，o和p如本文所定义 或其药用合适的酸盐、光学纯对映体、拉氏体或二对映异构体混合物。式I的化合物可用于治疗睡眠障碍，如睡眠呼吸暂停症、嗜睡症、失眠、睡眠障碍、时差综合征、昼夜节律紊乱或与神经系统疾病相关的睡眠障碍。
• Development of novel benzimidazole-derived neddylation inhibitors for suppressing tumor growth in vitro and in vivo
  作者：Xin Chen、Xi Yang、Fei Mao、Jinlian Wei、Yixiang Xu、Baoli Li、Jin Zhu、Shuaishuai Ni、Lijun Jia、Jian Li

  DOI：10.1016/j.ejmech.2020.112964

  日期：2021.1

  Ubiquitin-like protein neddylation is overactivated in various human cancers and correlates with disease progression, and targeting this pathway represents a valuable therapeutic strategy. Our previous work disclosed an antihypertensive agent, candesartan cilexetic (CDC), serves as a novel neddylation inhibitor for suppressing tumor growth by targeting Nedd8-activating enzyme (NAE). In this study,

  在多种人类癌症中，类似泛素的蛋白质糊化作用过度活化，并且与疾病进展相关，靶向这种途径代表了一种有价值的治疗策略。我们先前的工作公开了一种降压药坎地沙坦酯（CDC），它是一种新型的通过抑制Nedd8激活酶（NAE）抑制肿瘤生长的联糖化抑制剂。在这项研究中，基于铅化合物CDC设计并合成了42种苯并咪唑衍生物，以改善对神经酰胺化的抑制作用和抗癌效果。与CDC相比，最佳苯并咪唑衍生的35在酶法测定中显示出更好的烯丙基化抑制作用（IC 50 = 5.51μM对16.43μM），以及有希望的靶标抑制活性和杀死癌细胞的选择性。细胞机制研究与体内人肺癌细胞A549的肿瘤生长抑制相结合的结果，以及对接模型表明，35有潜力被开发为有前途的联结抑制剂用于抗癌治疗。
• [EN] 6-SUBSTITUTED PHENOXYCHROMAN CARBOXYLIC ACID DERIVATIVES<br/>[FR] DÉRIVÉS DE L'ACIDE CARBOXYLIQUE PHÉNOXYCHROMANE SUBSTITUÉS EN 6
  申请人：ARRAY BIOPHARMA INC

  公开号：WO2009158426A1

  公开（公告）日：2009-12-30

  Compounds of Formula (I): in which A1, A2, W, L, G, R7a, R7b, R8, R9 and R10 have the meanings given in the specification, are DP2 receptor modulators useful in the treatment of immunologic diseases.

  式（I）的化合物：其中A1、A2、W、L、G、R7a、R7b、R8、R9和R10具有规范中给定的含义，是DP2受体调节剂，可用于治疗免疫性疾病。
• 6-SUBSTITUTED PHENOXYCHROMAN CARBOXYLIC ACID DERIVATIVES
  申请人：Burgess Laurence E.

  公开号：US20110105463A1

  公开（公告）日：2011-05-05

  Compounds of Formula (I): in which A 1 , A 2 , W, L, G, R 7a , R 7b , R 8 , R 9 and R 10 have the meanings given in the specification, are DP2 receptor modulators useful in the treatment of immunologic diseases.

  式(I)的化合物：其中A1、A2、W、L、G、R7a、R7b、R8、R9和R10的含义如规范中所述，是DP2受体调节剂，对治疗免疫疾病有用。