4-氯甲基联苯 | 1667-11-4

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 烃类卤化物
• 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: 4-氯甲基联苯
• 中文别名: 4-(氯甲基)联苯
• 英文名称: biphenyl-4-methylchloride
• 英文别名: 4-phenylbenzyl chloride；4-(chloromethyl)-1,1'-biphenyl；4-chloromethylbiphenyl；4-(Chloromethyl)biphenyl；1-(chloromethyl)-4-phenylbenzene
• CAS: 1667-11-4
• 化学式: C₁₃H₁₁Cl
• mdl: MFCD00000917
• 分子量: 202.683
• InChiKey: HLQZCRVEEQKNMS-UHFFFAOYSA-N

物化性质

• 熔点：
  70-73 °C (lit.)
• 沸点：
  321.03°C (rough estimate)
• 密度：
  1.1339 (estimate)
• 稳定性/保质期：
  <p><b></b></p>

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 危险等级：
  IRRITANT
• 安全说明：
  S26,S36
• 危险品运输编号：
  NONH for all modes of transport
• WGK Germany：
  3
• 海关编码：
  2903999090
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• RTECS号：
  DV2087000
• 危险类别：
  IRRITANT
• 包装等级：
  II
• 危险性防范说明：
  P260,P264,P270,P280,P301+P330+P331,P303+P361+P353,P304+P340,P305+P351+P338,P310,P363,P405,P501
• 危险性描述：
  H302,H314
• 储存条件：
  库房应保持低温、通风和干燥的环境。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 4-(Chloromethyl)biphenyl
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
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: 4-(Chloromethyl)biphenyl
CAS number: 1667-11-4

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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.
Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
Eye contact:
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
Appearance: Not specified
No data
Boiling point:
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C13H11Cl
Molecular weight: 202.7

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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, 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

用途

4-氯甲基联苯是一种重要的联苯衍生物，在医药、高分子液晶及染料等领域有着广泛的应用。它可用于合成非甾体抗炎药如联苯乙酸和芬布芬，以及消炎镇痛药如联苯乙酸乙酯。

应用

4-氯甲基联苯是一种重要的联苯衍生物，在医药、高分子液晶及染料等领域有着广泛的应用。例如，可以通过该物质制备4-联苯乙酸（C14H12O2, 分子量 212.24），这是一种白色片状晶体且具有非甾体抗炎药特性，是芬布芬的有效代谢产物，能缓解变型性关节炎、肩周炎、腱鞘炎、肌肉痛、外伤肿胀及疼痛等症状。其衍生物联苯乙酸乙酯也是一种消炎镇痛药物，在治疗风湿性关节炎、腰痛、肩周炎和手术后疼痛方面表现出色，尤其对癌症疼痛的疗效显著。

该制备方法如下：以4-氯甲基联苯为原料，在催化剂二氯化钯和配体三苯基膦的存在下，并在碱性和溶剂环境下，与一氧化碳反应发生羰基化反应。随后经过酸化处理并分离，即可得到4-联苯乙酸。该方法可在50-100℃的温度范围内及0.3-1.0MPa的压力条件下进行，收率较高且三废排放较少，适宜工业化生产。

类别

有毒物质

可燃性危险特性

可燃，在燃烧时会分解产生有毒氯化物气体

储运特性

需低温、通风且干燥的库房储存

灭火剂

水、二氧化碳、干粉或砂土

反应信息

• 作为反应物：
  描述：

  4-氯甲基联苯 在 potassium hydroxide 、 锌 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.5h， 生成 4-联苯乙酸
  参考文献：
  名称：

  Organozinc Reagents for Facile Synthetic Route to Diflunisal, Fenbufen and Felbinac

  摘要：

  DOI：

  10.5012/bkcs.2011.32.1.341
• 作为产物：
  描述：

  4-联苯乙酸 在 2,4,6-三甲基吡啶 、 N-氯代丁二酰亚胺 、 4,4'-二甲氧基-2,2'-联吡啶 、 iron(II) acetate 作用下， 以 乙腈 为溶剂， 以47 %的产率得到4-氯甲基联苯
  参考文献：
  名称：

  可见光下铁盐催化脂肪族羧酸的脱羧卤化

  摘要：

  在本文中，我们报告了可见光下铁盐催化脂肪族羧酸直接脱羧氯化、碘化和溴化的通用方案。该方法底物范围广泛，具有良好的官能团兼容性，包括复杂的天然产物。苯甲基和烯丙基C(sp 3 )–H键可以在氧化卤化条件下保留。该方法还显示出后期功能化的应用潜力。

  DOI：

  10.1039/d3cc06149c
• 作为试剂：
  描述：

  4-乙炔苯酚 、 potassium carbonate 、 氯化铵 、 乙酸乙酯 在 4-氯甲基联苯 、 碘化钠 、 苄基氯甲基醚 水 、 正己烷 、 丙二醇甲醚醋酸酯 作用下， 以 二甲基亚砜 、 ice water 、 水 为溶剂， 反应 8.0h， 以to obtain 100.1 g of a PGMEA solution (33.8 mass %) of Resin (P-4)的产率得到丙二醇甲醚醋酸酯
  参考文献：
  名称：

  ACTINIC RAY-SENSITIVE OR RADIATION-SENSITIVE RESIN COMPOSITION, RESIST FILM USING THE COMPOSITION AND PATTERN FORMING METHOD

  摘要：

  一种感光树脂组合物，其包括（P）一种具有以下式（1）所表示的重复单元的树脂，使用该组合物的光阻膜以及一种图案形成方法。

  公开号：

  US20120301817A1

文献信息

• Method of treating tumors
  申请人：Svendsen John Sigurd

  公开号：US09115169B2

  公开（公告）日：2015-08-25

  The invention provides a method of treating tumors by adminstering to a human or animal patient an effective amount of a molecule of 2 to 4 amino acids or equivalent subunits in length, which incorporates a bulky and lipophilic group comprising at least 13 non-hydrogen atoms and containing no more than 2 polar functional groups, in which the bulky and lipophilic group incorporates one or more closed rings of 5 or more non-hydrogen atoms, and in which the molecule further has at least two more cationic than anionic moieties.

  这项发明提供了一种治疗肿瘤的方法，通过向人类或动物患者施用含有2至4个氨基酸或等效亚单位的分子的有效量，该分子包含至少13个非氢原子的庞大和亲脂基团，并且不含有超过2个极性功能团，在这种庞大和亲脂基团中包含了一个或多个由5个或更多个非氢原子组成的闭环，并且该分子还具有至少两个阳离子基团多于阴离子基团。
• Discovery of Highly Potent 2-Sulfonyl-Pyrimidinyl Derivatives for Apoptosis Inhibition and Ischemia Treatment
  作者：Li Li、Xian Jiang、Shaoqiang Huang、Zhengxin Ying、Zhaolan Zhang、Chenjie Pan、Sisi Li、Xiaodong Wang、Zhiyuan Zhang

  DOI：10.1021/acsmedchemlett.6b00489

  日期：2017.4.13

  series of 2-sulfonyl-pyrimidinyl derivatives was developed as apoptosis inhibitors. These represent the first class of apoptosis inhibitors that function through stabilizing mitochondrial respiratory complex II. Starting from a phenotypic screen hit with micromolar activity, we optimized the cellular apoptosis inhibition activity of 2-sulfonyl-pyrimidinyl derivatives to picomolar level (compound 42

  开发了一系列2-磺酰基-嘧啶基衍生物作为凋亡抑制剂。这些代表通过稳定线粒体呼吸复合物II起作用的第一类凋亡抑制剂。从具有微摩尔活性的表型筛选开始，我们将2-磺酰基-嘧啶基衍生物的细胞凋亡抑制活性优化至皮摩尔水平（化合物42，也称为TC9-305）。这些新的细胞凋亡抑制剂对缺血动物模型的神经保护作用进一步证明了其治疗潜力。
• Palladium-Catalyzed/Norbornene-Mediated CH Activation/<i>N</i>-Tosylhydrazone Insertion Reaction: A Route to Highly Functionalized Vinylarenes
  作者：Ping-Xin Zhou、Lan Zheng、Jun-Wei Ma、Yu-Ying Ye、Xue-Yuan Liu、Peng-Fei Xu、Yong-Min Liang

  DOI：10.1002/chem.201402097

  日期：2014.5.26

  A straightforward method for the synthesis of highly functionalized vinylarenes through palladium‐catalyzed, norbornene‐mediated CH activation/carbene migratory insertion is described. Extension to a one‐pot procedure is also developed. Furthermore, this method can also be used to generate polysubstituted bicyclic molecules. The reaction proceeds under mild conditions to give the products in satisfactory

  描述了一种通过钯催化，降冰片烯介导的CH活化/卡宾迁移插入合成高度官能化乙烯基芳烃的简单方法。还开发了扩展到一锅法的程序。此外，该方法也可以用于产生多取代的双环分子。反应在温和的条件下进行，使用容易获得的起始原料，以令人满意的产率得到产物。这是Catellani–Lautens反应，其中包含不同类型的偶联伙伴。此外，该反应是第一个证明将Pd催化的重氮化合物插入与Pd催化的CH活化相结合的反应。
• A versatile difluorovinylation method: Cross-coupling reactions of the 2,2-difluorovinylzinc–TMEDA complex with alkenyl, alkynyl, allyl, and benzyl halides
  作者：Tomohiro Ichitsuka、Tsuyoshi Takanohashi、Takeshi Fujita、Junji Ichikawa

  DOI：10.1016/j.jfluchem.2014.12.003

  日期：2015.2

  2-difluorovinylzinc–TMEDA complex was prepared via a deprotonation–transmetallation sequence starting from commercially available 1,1-difluoroethylene. The complex thus formed was successfully applied to transition metal-catalyzed cross-coupling reactions with a wide range of organic halides, which led to the syntheses of 2,2-difluorovinyl compounds. On treatment with the difluorovinylzinc–TMEDA complex in the presence

  通过去质子化-金属间转移序列，从可商购的1,1-二氟乙烯开始制备热稳定的2,2-二氟乙烯基锌-TMEDA复合物。如此形成的配合物已成功地用于过渡金属催化的与多种有机卤化物的交叉偶联反应，从而导致了2,2-二氟乙烯基化合物的合成。在适当的钯或铜催化剂存在下用二氟乙烯基锌-TMEDA复合物处理时，烯基，炔基，烯丙基和苄基卤化物会有效地进行二氟乙烯基化，从而得到1,1-二氟-1,3-二烯，1,1-二氟-1，3-烯炔，1，1-二氟-1，4-二烯和（3，3-二氟烯丙基）芳烃。
• FUROISOQUINOLINE DERIVATIVE AND USE THEREOF
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1541576A1

  公开（公告）日：2005-06-15

  The present invention provides a compound represented by the formula    wherein A represents (1) a bond, (2) a group represented by the formula -CRa=CRb- (Ra and Rb each represent a hydrogen atom or C1-6 alkyl) and the like; R1 represents (1) cyano or (2) an optionally esterified or amidated carboxyl group; R2 represents (1) a hydrogen atom, (2) an optionally substituted hydroxy group, (3) an optionally substituted amino group and the like; R3 and R4 each represent a hydrogen atom and the like; R5 represents a hydrogen atom and the like; R6 represents an optionally substituted hydroxy group and the like; R7and R8 each represent an optionally substituted hydrocarbon group and the like; R9 and R10 each represent (1) a hydrogen atom and the like; Y represents an optionally substituted methylene group; and n represents 0 or 1, or a salt thereof, which has an excellent phosphodiesterase IV inhibiting action.

  本发明提供了一种化合物，其表示为式中的化合物，其中A代表（1）键，（2）由式 -CRa=CRb-（Ra和Rb分别代表氢原子或C1-6烷基等）表示的基团等；R1代表（1）氰基或（2）可选择酯化或酰胺化的羧基；R2代表（1）氢原子，（2）可选择取代的羟基，（3）可选择取代的氨基等；R3和R4各自代表氢原子等；R5代表氢原子等；R6代表可选择取代的羟基等；R7和R8各自代表可选择取代的碳氢基团等；R9和R10各自代表（1）氢原子等；Y代表可选择取代的亚甲基基团；n代表0或1，或其盐，具有优异的磷酸二酯酶IV抑制作用。

表征谱图