1-(3-溴丙氧基)-2,4-二氯苯 | 6954-78-5

• 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: 1-(3-溴丙氧基)-2,4-二氯苯
• 英文名称: 1-(3-bromopropoxy)-2,4-dichlorobenzene
• 英文别名: 1-bromo-3-(2,4-dichlorophenoxy)propane；3-bromo-(2',4'-dichlorophenoxy)propane；3-(2,4-dichlorophenoxy)propyl bromide；(3-bromo-propyl)-(2,4-dichloro-phenyl)-ether；(3-Brom-propyl)-(2,4-dichlor-phenyl)-aether；1-(3-bromopropoxy)-2,4-dichloro-benzene
• CAS: 6954-78-5
• 化学式: C₉H₉BrCl₂O
• 分子量: 283.98
• InChiKey: ULFFEDBFOCOYOH-UHFFFAOYSA-N

物化性质

• 沸点：
  170-174 °C (12 mmHg)
• 闪点：
  180 °C
• 稳定性/保质期：
  避免与不相容的材料接触，特别是强氧化剂。

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R20/22,R36/37/38
• 海关编码：
  2909309090
• 储存条件：
  密封储存，应存放在阴凉干燥的库房中。

SDS

Name:	1-(3-Bromopropoxy)-2 4-dichlorobenzene Material Safety Data Sheet
Synonym:
CAS:	6954-78-5

Section 1 - Chemical Product MSDS Name:1-(3-Bromopropoxy)-2 4-dichlorobenzene Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
6954-78-5	1-(3-Bromopropoxy)-2,4-dichlorobenzene		unlisted

Hazard Symbols: XN
Risk Phrases: 20/22 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation and if swallowed. 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:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Harmful if inhaled. Causes respiratory tract irritation.
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:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable 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# 6954-78-5: 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: Liquid
Color: colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 170 - 174 deg C @12mmHg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: 180 deg C ( 356.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: >170 deg C
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C9H9BrCl2O
Molecular Weight: 283.98

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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.
Hazardous Decomposition Products:
Hydrogen chloride, carbon monoxide, carbon dioxide, hydrogen bromide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 6954-78-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-(3-Bromopropoxy)-2,4-dichlorobenzene - 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
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2810
Packing Group: III
IMO
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
Packing Group: III
RID/ADR
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/22 Harmful by inhalation and if swallowed.
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 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 6954-78-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 6954-78-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 6954-78-5 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：

  1-(3-溴丙氧基)-2,4-二氯苯 在 lithium aluminium tetrahydride 、 sodium azide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 3-(2,4-dichlorophenoxy)propan-1-amine
  参考文献：
  名称：

  Expeditious synthesis and biological evaluation of novel 2,N6-disubstituted 1,2-dihydro-1,3,5-triazine-4,6-diamines as potential antimalarials

  摘要：

  A small set of novel 2,N-6-disubstituted 1,2-dihydro-1,3,5-triazine-4,6-diamines was prepared possessing a flexible tether between the exocyclic nitrogen bonded to C-6 of the 1,2-dihydro-1,3,5-triazine-4,6-diamine heterocycle and the distal aryl ring. Three zones were varied in this series of compounds, namely the nature of the substituent(s) on C-2; the nature of the substituent(s) on the distal aryl ring; as well as the nature and length of the flexible tether between the rings. The compound showing the best antimalarial activity (cycloguanil-resistant FCR-3 Plasmodium falciparum IC50 = 0.99 mu M) was N-6-(3-(4-chlorophenoxy)propyl)-2-(furan-2-yl)-1,2-dihydro-1,3,5-triazine-4,6-diamine hydrochloride. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.054
• 作为产物：
  描述：

  1,3-二溴丙烷 、 2,4-二氯酚 在 sodium hydride 作用下， 以 异丁酰胺 为溶剂， 反应 5.0h， 以69.8%的产率得到1-(3-溴丙氧基)-2,4-二氯苯
  参考文献：
  名称：

  N取代的1,2,3,6-四氢吡啶对时间依赖性的可逆缓慢抑制单胺氧化酶A的作用

  摘要：

  发现一类新型的N-取代的四氢吡啶衍生物具有单胺氧化酶A抑制的多种动力学机制。合成了十一种结构相似的四氢吡啶衍生物，并将其评估为MAO-A和MAO-B的抑制剂。该系列中最有效的MAO-A抑制剂2,4-二氯苯氧基丙基类似物12显示出时间依赖性混合非竞争性抑制作用。通过透析逆转抑制，表明可逆酶抑制。有证据表明MAO-A与12具有缓慢结合抑制作用涉及通过用硼氢化钠还原来稳定共价可逆中间产物而获得的共价键。还原的酶复合物不可通过透析逆转。结果与缓慢可逆的基于机制的抑制作用相一致。选择性抑制MAO-A的两个四氢吡啶类似物的特征在于其动力学机理不同于12的动力学机理。作为MAO-A的可逆抑制剂，四氢吡啶类似物处于酪胺引起的高血压不良反应的低风险中。

  DOI：

  10.1016/j.bmc.2011.10.038

文献信息

• Discovery, design and synthesis of novel potent and selective sphingosine-1-phosphate 4 receptor (S1P4-R) agonists
  作者：Miguel Guerrero、Mariangela Urbano、Jian Zhao、Melissa Crisp、Peter Chase、Peter Hodder、Marie-Therese Schaeffer、Steven Brown、Hugh Rosen、Edward Roberts

  DOI：10.1016/j.bmcl.2011.10.096

  日期：2012.1

  potent and selective S1P4-R hit agonist. Design, synthesis and systematic structure–activity relationships study of the HTS-derived hit led to the development of novel potent S1P4-R agonists exquisitely selective over the remaining S1P1–3,5-Rs family members. Remarkably, the molecules herein reported provide novel pharmacological tools to decipher the biological function and assess the therapeutic utility

  S1P 4受体 (S1P 4 -R) 的高亲和力和选择性小分子激动剂可能在包括自身免疫性疾病、病毒感染和血小板减少症在内的多种疾病领域具有重要的治疗效用。分子库-小分子库库的高通量筛选 (HTS) 鉴定出 3-(2-(2,4-dichlorophenoxy)ethoxy)-6-methyl-2-nitropyridine 是一种中等效力和选择性的 S1P 4 -R击中激动剂。HTS 衍生命中的设计、合成和系统的结构-活性关系研究导致了新型强效 S1P 4 -R 激动剂的开发，该激动剂对剩余的 S1P 1-3,5 具有极好的选择性-Rs 家庭成员。值得注意的是，本文报道的分子提供了新的药理学工具来破译生物学功能并评估 S1P 4 -R的治疗效用。
• [EN] NOVEL ANTI-INFECTIVE COMPOUNDS AND METHODS USING SAME<br/>[FR] NOUVEAUX COMPOSÉS ANTI-INFECTIEUX ET LEURS MÉTHODES D'UTILISATION
  申请人：UNIV PENNSYLVANIA

  公开号：WO2016077541A1

  公开（公告）日：2016-05-19

  The present invention includes a method of treating or preventing a bacterial infection in a subject in need thereof. The method comprises administering to the subject a therapeutically effective amount of at least one compound of the invention. In certain embodiments, the bacterium is Gram-negative. In other embodiments, the bacterium is obligatory aerobic.

  本发明涉及一种治疗或预防需要的主体中的细菌感染的方法。该方法包括向该主体施用本发明至少一种化合物的治疗有效量。在某些实施方式中，细菌为革兰氏阴性菌。在其他实施方式中，细菌为厌氧菌。
• Design, synthesis, docking studies and biological evaluation of novel dihydro-1,3,5-triazines as human DHFR inhibitors
  作者：Xiaotian Zhou、Kuaile Lin、Xiang Ma、Wai-Keung Chui、Weicheng Zhou

  DOI：10.1016/j.ejmech.2016.11.010

  日期：2017.1

  A novel series of dihydro-1,3,5-triazine derivatives bearing a heteroatom spiro-ring were designed and synthesized on the basis of molecular flexible docking work, and their biological activities were evaluated. Compounds A2, A5, B1 and B3 showed potent human dihydrofolate reductase (hDHFR) inhibitory activity with IC50 values of 7.46 nM, 3.72 nM, 6.46 nM, 4.08 nM, versus reference drug methotrexate

  在分子对接作用的基础上，设计合成了一系列带有杂原子螺环的二氢-1,3,5-三嗪衍生物，并对其生物学活性进行了评价。化合物A2，A5，B1和B3显示有效的人二氢叶酸还原酶（hDHFR）抑制活性，相对于参考药物甲氨蝶呤（MTX），IC 50值为7.46 nM，3.72 nM，6.46 nM，4.08 nM。从分子对接的结果可以得出结论，由柔性残基Phe31变形产生的构象空间有利于螺环的结合，而将杂原子插入螺环中可能会增加结合亲和力。有24种化合物具有对多种肿瘤细胞系（HCT116，A549，HL-60，HepG2和MDA-MB-231）具有广谱抗增殖活性的化合物50个值，范围从0.79至0.001μM。在人肺泡基底上皮细胞系A549异种移植模型中确定化合物A2的体内抗肿瘤活性。这项研究提供了具有高抑制活性的靶向hDHFR的新型抗癌药，并具有新型分子支架与hDHFR的结合模式。这为进一步开发新型hDHFR抑制剂提供了有力的支持。
• Synthesis and Characterization of 11C-Labeled Fluoroclorgyline: A Monoamine Oxidase A Specific Inhibitor for Positron Emission Tomography.
  作者：Yoshiro OHMOMO、Masahiko HIRATA、Katsuhiko MURAKAMI、Yasuhiro MAGATA、Chiaki TANAKA、Akira YOKOYAMA

  DOI：10.1248/cpb.41.1994

  日期：——

  A new radioligand for monoamine oxidase type A (MAO-A), [11C]fluoroclorgyline, was synthesized from its desmethyl precursor by N-methylation reaction using [11C]methyl iodide with a radiochemical yield of 75-85%. The radiochemical purity of the product was more than 99% and the specific radioactivity was 7.4-18.5 GBq/μmol. The in vivo tissue distribution studies of [11C]fluoroclorgyline in mice demonstrated its high initial uptake and prolonged retention in the brain, comparable to those of [11C]clorgyline. A selective interaction with MAO-A in the accumulation of [11C]fluoroclorgyline was confirmed by a competition experiment performed with the MAO-A specific inhibitor, clorgyline, and MAO-B specific inhibitor, l-deprenyl. These very desirable characteristics of [11] fluoroclorgyline suggested that its 18F labeled counterpart, [18F]fluoroclorgyline, would have great potential as a longer-lived alternative to 11C labeled clorgyline for in vivo studies of MAO-A in the human brain with positron emission tomography (PET).

  利用[11C]甲基碘通过 N-甲基化反应合成了一种新的单胺氧化酶 A 型（MAO-A）放射性配体--[11C]氟氯吉林，其放射化学收率为 75-85%。产品的放射化学纯度超过 99%，比放射性为 7.4-18.5 GBq/μmol。[11C]氟氯吉林在小鼠体内的组织分布研究表明，它在大脑中的初始摄取量高，保留时间长，与[11C]氯吉林相当。在[11C]氟氯吉林的蓄积过程中与 MAO-A 的选择性相互作用是通过与 MAO-A 特异性抑制剂氯吉林和 MAO-B 特异性抑制剂 l-deprenyl 的竞争实验来证实的。[11]氟氯吉林的这些非常理想的特性表明，其 18F 标记的对应物[18F]氟氯吉林作为 11C 标记的氯吉林的长效替代物，在利用正电子发射断层扫描（PET）对人脑中的 MAO-A 进行体内研究方面具有巨大的潜力。
• Positron emitter labeled enzyme inhibitors
  申请人：The United States of America as represented by the United States

  公开号：US04913891A1

  公开（公告）日：1990-04-03

  This invention involves a new strategy for imaging and mapping enzyme activity in the living human and animal body using positron emitter-labeled suicide enzyme inactivators or inhibitors which become covalently bound to the enzyme as a result of enzymatic catalysis. Two such suicide inactivators for monoamine oxidase have been labeled with carbon-11 and used to map the enzyme subtypes in the living human and animal body using PET. By using positron emission tomography to image the distribution of radioactivity produced by the body penetrating radiation emitted by carbon-11, a map of functionally active monoamine oxidase activity is obtained. Clorgyline and L-deprenyl are suicide enzyme inhibitors and irreversibly inhibit monoamine oxidase. When these inhibitors are labeled with carbon-11 they provide selective probes for monoamine oxidase localization and reactivity in vivo using positron emission tomography.

  这项发明涉及一种新的策略，用正电子发射体标记的自杀酶失活剂或抑制剂来成像和映射活体人体和动物体内的酶活性，这些物质会由于酶催化而与酶共价结合。已经用碳-11标记了两种单胺氧化酶的自杀失活剂，并用于使用正电子发射体显像技术在活体人体和动物体内映射酶亚型。通过利用正电子发射断层扫描成像由碳-11放射出的体内穿透辐射产生的放射性分布图，可以获得功能活性的单胺氧化酶活性图。Clorgyline和L-依普利纽是自杀酶抑制剂，可以不可逆地抑制单胺氧化酶。当这些抑制剂用碳-11标记时，它们提供了用于在体内使用正电子发射断层扫描成像定位和反应性的选择性探针。