1-(4-溴丁氧基)-4-氟苯 | 2033-80-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-(4-溴丁氧基)-4-氟苯
• 英文名称: 1-(4-bromobutoxy)-4-fluorobenzene
• 英文别名: 1-bromo-4-(p-fluorophenoxy)butane
• CAS: 2033-80-9
• 化学式: C₁₀H₁₂BrFO
• 分子量: 247.107
• InChiKey: SESKDKZVNDEQBM-UHFFFAOYSA-N

物化性质

• 沸点：
  195 °C (12 mmHg)
• 稳定性/保质期：
  避免与不相容的材料接触。

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn
• 危险类别码：
  R20/22,R36/37/38
• 海关编码：
  2909309090
• 安全说明：
  S26,S37/39
• 储存条件：
  密封储存，应存放在阴凉、干燥的库房中。

SDS

Name:	1-(4-Bromobutoxy)-4-fluorobenzene Material Safety Data Sheet
Synonym:
CAS:	2033-80-9

Section 1 - Chemical Product MSDS Name:1-(4-Bromobutoxy)-4-fluorobenzene Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
2033-80-9	1-(4-Bromobutoxy)-4-fluorobenzene	100	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. Lachrymator (substance which increases the flow of tears).
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:
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.
Ingestion:
Do not induce vomiting. 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. Avoid generating dusty conditions.

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Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Use only in a chemical fume hood.
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# 2033-80-9: 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: Crystals
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 195 deg C @12mmHg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: >240 deg C
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C10H12BrFO
Molecular Weight: 247.11

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
No information found.
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# 2033-80-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-(4-Bromobutoxy)-4-fluorobenzene - 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 SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
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 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 2033-80-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 2033-80-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 2033-80-9 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-(4-溴丁氧基)-4-氟苯 在 sodium sulfite 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 0.25h， 生成 C₁₀H₁₂FO₄S^(1-)*Na⁽¹⁺⁾
  参考文献：
  名称：

  Microwave-assisted synthesis of sodium sulfonates precursors of sulfonyl chlorides and fluorides

  摘要：

  We describe the use of a microwave reaction for the conversion of various bromides to sodium sulfonates that have been further elaborated to sulfonyl chlorides. This new approach leads to much improved yields and shorter reaction times. Representative sulfonyl chlorides serve as precursors for the respective sulfonyl fluorides that are potent inhibitors of the fatty acid amide hydrolase. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.09.167
• 作为产物：
  描述：

  1-(but-3-en-1-yloxy)-4-fluorobenzene 在 silver(I) bromide 、 三甲基溴硅烷 、 氧气 、 1,5-环辛二烯 作用下， 以 二氯甲烷 、 水 为溶剂， 以92%的产率得到1-(4-溴丁氧基)-4-氟苯
  参考文献：
  名称：

  铁（II）和铜（I）控制烯烃氢溴化反应的总区域选择性

  摘要：

  描述了一种可以完全控制烯烃氢溴化反应的区域选择性的新方法。在此，我们报告了一种使用 TMSBr 和氧作为常用试剂的自由基过程，其中在存在百万分之几的 Cu(I) 物种的情况下，反马尔可夫尼科夫产物的形成发生，而马尔可夫尼科夫产物的形成发生在存在 30 mol% 的溴化铁 (II)。密度泛函理论计算结合福井的激进磁化率支持获得的结果。

  DOI：

  10.1021/acs.orglett.1c02186

文献信息

• Diversity‐Oriented Synthesis of Aliphatic Fluorides via Reductive C(sp³)−C(sp³) Cross‐Coupling Fluoroalkylation
  作者：Jie Sheng、Hui‐Qi Ni、Shan‐Xiu Ni、Yan He、Ru Cui、Guang‐Xu Liao、Kang‐Jie Bian、Bing‐Bing Wu、Xi‐Sheng Wang

  DOI：10.1002/anie.202102481

  日期：2021.6.25

  catalyst and alkyl bromide whereas the generation of monofluoroalkyl radical is not involved in the rate-determining step. This strategy provides a general and efficient method for the synthesis of aliphatic fluorides.

  单氟化烷基化合物在药物、农用化学品和材料中具有重要意义。在此，我们描述了使用低成本工业原料溴氟甲烷对未活化的卤代烷进行直接镍催化的单氟甲基化，展示了两种卤代烷的通用且有效的还原交叉偶联。1-溴-1-氟烷烃的结果也证明了单氟烷基化的可行性，这进一步确立了还原性 C(sp 3 )-C(sp 3) 交叉偶联氟烷基化。这些转化表现出高效、温和的条件和出色的官能团兼容性，尤其是对于一系列药物和生物活性化合物。机制研究支持激进途径。动力学研究表明，该反应一级依赖于催化剂和烷基溴，而单氟烷基自由基的产生不参与限速步骤。该策略为合成脂肪族氟化物提供了一种通用且有效的方法。
• The one-pot synthesis of butyl-1H-indol-3-alkylcarboxylic acid derivatives in ionic liquid as potent dual-acting agent for management of BPH
  作者：Li-Yan Zeng、Fubiao Yang、Kaixuan Chen、Yunong Zeng、Zhenzhou Jiang、Shuwen Liu、Baomin Xi

  DOI：10.1016/j.ejmech.2020.112616

  日期：2020.11

  H-indol-3-yl)butanoic acid 4aaa was designed against BPH and synthesized by two steps of N-alkylation. One-pot protocol towards 4aaa was newly developed. With IL [C6min]Br as solvent, the yield of 4aaa was increased to 75.1 % from 16.0 % and the reaction time was shortened in 1.5 hours from 48 hours. 25 Derivatives structurally based on arylpiperazine and indolyl butyric acid with alkyl linker were

  基于两种α的SAR 1 -AR拮抗剂和5α还原酶（5AR）抑制剂，双重作用的药剂4-（1-（4-（4-（2-甲氧基苯基）哌嗪-1-基）丁基针对BPH设计了）-1 H-吲哚-3-基）丁酸4aaa，并通过N-烷基化的两个步骤合成。新开发了针对4aaa的一锅协议。用IL [C 6分钟]溴作为溶剂，收率4AAA从16.0％提高到75.1％，反应时间是1.5小时缩短为48小时。制备了25种基于芳基哌嗪和吲哚基丁酸的具有烷基连接基的衍生物。进一步扩展了该协议，以获取另外14个衍生词，其中O-烷基化参与其中，并应用于生物有效分子DPQ和阿立哌唑的合成。预期地，化合物4AAA表现出α的双重抑制1 -AR和5α还原酶，和exihited针对人类细胞没有明显的细胞毒性。还确定了4aaa的药代动力学特性。
• Design of PAP-1, a Selective Small Molecule Kv1.3 Blocker, for the Suppression of Effector Memory T Cells in Autoimmune Diseases
  作者：Alexander Schmitz、Ananthakrishnan Sankaranarayanan、Philippe Azam、Kristina Schmidt-Lassen、Daniel Homerick、Wolfram Hänsel、Heike Wulff

  DOI：10.1124/mol.105.015669

  日期：2005.11

  The lymphocyte K+ channel Kv1.3 constitutes an attractive pharmacological target for the selective suppression of terminally differentiated effector memory T (TEM) cells in T cell-mediated autoimmune diseases, such as multiple sclerosis and type 1 diabetes. Unfortunately, none of the existing small-molecule Kv1.3 blockers is selective, and many of them, such as correolide, 4-phenyl-4-[3-(methoxyphenyl)-3-oxo-2-azapropyl]cyclohexanone, and our own compound Psora-4 inhibit the cardiac K+ channel Kv1.5. By further exploring the structure-activity relationship around Psora-4 through a combination of traditional medicinal chemistry and whole-cell patch-clamp, we identified a series of new phenoxyalkoxypsoralens that exhibit 2- to 50-fold selectivity for Kv1.3 over Kv1.5, depending on their exact substitution pattern. The most potent and “drug-like” compound of this series, 5-(4-phenoxybutoxy)psoralen (PAP-1), blocks Kv1.3 in a use-dependent manner, with a Hill coefficient of 2 and an EC50 of 2 nM, by preferentially binding to the C-type inactivated state of the channel. PAP-1 is 23-fold selective over Kv1.5, 33- to 125-fold selective over other Kv1-family channels, and 500- to 7500-fold selective over Kv2.1, Kv3.1, Kv3.2, Kv4.2, HERG, calcium-activated K+ channels, Na+,Ca2+, and Cl- channels. PAP-1 does not exhibit cytotoxic or phototoxic effects, is negative in the Ames test, and affects cytochrome P450-dependent enzymes only at micromolar concentrations. PAP-1 potently inhibits the proliferation of human TEM cells and suppresses delayed type hypersensitivity, a TEM cell-mediated reaction, in rats. PAP-1 and several of its derivatives therefore constitute excellent new tools to further explore Kv1.3 as a target for immunosuppression and could potentially be developed into orally available immunomodulators.

  淋巴细胞K+通道Kv1.3是选择性抑制T细胞介导的自身免疫性疾病（如多发性硬化症和1型糖尿病）中终末分化效应记忆T（TEM）细胞的有吸引力的药理学靶点。不幸的是，目前存在的所有小分子Kv1.3阻断剂均不具备选择性，其中许多如柯里奥利德、4-苯基-4-[3-(甲氧苯基)-3-酮-2-氮杂丙基]环己酮以及我们自己的化合物Psora-4均可抑制心脏K+通道Kv1.5。通过结合传统药物化学和全细胞膜片钳技术进一步探索Psora-4的构效关系，我们鉴定了一系列新的苯氧烷氧基补骨脂素，它们对Kv1.3的选择性比Kv1.5高2至50倍，具体取决于其取代模式。这一系列化合物中，最具有强效和“类药物”性质的化合物为5-(4-苯氧基丁氧基)补骨脂素（PAP-1），它以使用依赖性方式阻断Kv1.3，Hill系数为2，EC50为2 nM，通过优先结合通道的C型失活态。PAP-1对Kv1.5的选择性为23倍，对其他Kv1家族通道的选择性为33至125倍，对Kv2.1、Kv3.1、Kv3.2、Kv4.2、HERG、钙激活K+通道、Na+、Ca2+及Cl-通道的选择性为500至7000倍。PAP-1无细胞毒性或光毒性，Ames试验呈阴性，对细胞色素P450依赖性酶的影响仅在微摩尔浓度下显现。PAP-1能强效抑制人TEM细胞的增殖并抑制大鼠中的迟发型超敏反应（一种TEM细胞介导的反应）。因此，PAP-1及其若干衍生物构成了探索Kv1.3作为免疫抑制靶点的新工具，并有可能开发成口服可用的免疫调节剂。
• Copper-Catalyzed Trifluoromethylthiolation of Primary and Secondary Alkylboronic Acids
  作者：Xinxin Shao、Tianfei Liu、Long Lu、Qilong Shen

  DOI：10.1021/ol502132j

  日期：2014.9.19

  A Cu-catalyzed trifluoromethylthiolation of primary and secondary alkylboronic acids with an electrophilic trifluoromethylthiolating reagent is described. Tolerance for a variety of functional groups was observed.

  描述了用亲电子的三氟甲基硫醇化试剂的Cu催化的伯烷基硼酸和仲烷基硼酸的三氟甲基硫醇化。观察到对各种官能团的耐受性。
• Nickel-Catalyzed Multicomponent Coupling Reaction of Alkyl Halides, Isocyanides and H2O: An Expedient Way to Access Alkyl Amides
  作者：Yunkui Liu、Bingwei Zhou、Qiao Li、Hongwei Jin

  DOI：10.1055/s-0040-1707229

  日期：2020.11

  multicomponent coupling reaction of alkyl halides, isocyanides, and H2O to access alkyl amides. Bench-stable NiCl2(dppp) is competent to initiate this transformation under mild reaction conditions, thus allowing easy operation and adding practical value. Substrate scope studies revealed a broad functional group tolerance and generality of primary and secondary alkyl halides in this protocol. A plausible

  摘要 我们在本文中描述了烷基卤，异氰酸酯和H 2 O的Ni催化的多组分偶联反应，以得到烷基酰胺。稳定的NiCl 2（dppp）能够在温和的反应条件下引发这种转变，从而使操作简便并增加实用价值。底物范围的研究表明，该方案对伯烷基卤和仲烷基卤具有广泛的官能团耐受性和通用性。基于初步实验和先前文献，提出了通过SET过程的合理的催化循环。