1-溴甲基萘 | 3163-27-7

• 物质功能分类: 化学试剂 - 有机试剂 - 多环化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 1-溴甲基萘
• 英文名称: 2-(bromomethyl)naphthalene
• 英文别名: 1-bromomethylnaphthalene；1-(Bromomethyl)naphthalene
• CAS: 3163-27-7
• 化学式: C₁₁H₉Br
• 分子量: 221.096
• InChiKey: RZJGKPNCYQZFGR-UHFFFAOYSA-N

物化性质

• 熔点：
  52-55°C
• 沸点：
  213°C/100mmHg
• 密度：
  1.44
• 最大波长(λmax)：
  292nm(Cyclohexane)(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 危险等级：
  8
• 安全说明：
  S26,S36
• 海关编码：
  2903999090
• 危险品标志：
  Xi
• 危险类别码：
  R20/21/22
• 包装等级：
  II
• 危险类别：
  8
• 危险性防范说明：
  P234,P260,P264,P272,P280,P301+P330+P331,P303+P361+P353,P304+P340+P310,P305+P351+P338+P310,P333+P313,P362+P364,P390,P405,P406,P501
• 危险品运输编号：
  3261
• 危险性描述：
  H290,H314,H317
• 储存条件：
  存储于0-5°C环境中

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 1-(Bromomethyl)naphthalene
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H314: Causes severe skin burns and eye damage
H318: Causes serious eye damage
P260: Do not breathe dust/fume/gas/mist/vapours/spray
P303+P361+P353: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with
water/shower
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P301+P330+P331: IF SWALLOWED: Rinse mouth. Do NOT induce vomiting
P405: Store locked up

---

Section 3. Composition/information on ingredients.
Ingredient name: 1-(Bromomethyl)naphthalene
CAS number: 3163-27-7

---

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.

---

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.

---

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.

---

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, refrigerated.

---

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.

---

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: C11H9Br
Molecular weight: 221.1

---

Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, hydrogen bromide.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

Section 14. Transportation information
UN Number: UN3261 Class: 8 Packing group: II
Proper shipping name: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S. (1-(Bromomethyl)naphthalene)

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

1-溴甲基萘是一种化学物质，可通过将1-甲基萘经N-溴代琥珀酰亚胺（NBS）光溴化反应制备得到。其化学性质为白色固体粉末。

反应信息

• 作为反应物：
  描述：

  1-溴甲基萘 在 2-硝基丙烷 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 7.0h， 生成 1-萘甲醛
  参考文献：
  名称：

  Synthesis and Biological Activity of New 3-Hydroxy-3-methylglutaryl Coenzyme A (HMG-CoA) Synthase Inhibitors: 2-Oxetanones with a Side Chain Mimicking the Folded Structure of 1233A.

  摘要：

  为模拟1233A（1）的折叠侧链构象，该化合物是一种3-羟基-3-甲基戊二酰辅酶A（HMG-CoA）合酶抑制剂，合成了侧链含有芳环的1233A类似物。其中2-恶坦酮部分保持不变。在1233A及其合成类似物中，反式-3-羟甲基-4-[2-(7-甲氧羰基-1-萘基)乙基]-2-恶坦酮（23）显示了最高的HMG-CoA合酶体外抑制活性。讨论了侧链上的构效关系。

  DOI：

  10.1248/cpb.42.512
• 作为产物：
  描述：

  1-萘甲醇 在 1-氯-N,N,2-三甲基丙烯胺 、 lithium bromide 作用下， 以 氘代乙腈 为溶剂， 生成 1-溴甲基萘
  参考文献：
  名称：

  一种用卤素取代羟基的温和方法：2.统一的程序和立体化学研究

  摘要：

  N，N-二甲基-和N，N-二异丙基-1-卤代-2-甲基-1-丙烯胺是容易获得的用于醇和羟基酸的轻度脱氧卤代的试剂。在这项研究中，我们表明可以通过改变试剂上烷基的大小来调节试剂的反应性：用异丙基取代甲基可以显着提高反应性。然后，我们使用容易获得的α描述了所有脱氧卤化反应的统一程序-氯亚胺作为试剂，带有（溴化，碘化）或不带有（氯化）碱性溴化物或碘化物。最后，我们表明仲醇的脱氧卤化反应具有高度的立体定向性，通常发生构型反转。

  DOI：

  10.1016/j.tet.2020.131441
• 作为试剂：
  描述：

  4,5-二氯咪唑 、 氢氧化钾 、 2-溴甲基萘 在 溴化钾 、 1-溴甲基萘 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 4,5-dichloro-1,3-bis(naphthalen-2-ylmethyl)-1H-imidazolium bromide
  参考文献：
  名称：

  AZOLIUM AND PURINIUM SALT ANTICANCER AND ANTIMICROBIAL AGENTS

  摘要：

  单电荷和多电荷咪唑阳离子（ICs）已被确定为一类具有强效抗肿瘤、抗菌和抗微生物特性的化学成分。所公开的咪唑阳离子在对癌细胞的作用上表现出与当前临床标准药物顺铂相当或更强的效力。然而，这些咪唑阳离子在不像顺铂这样的重金属抗肿瘤药物所知的毒性副作用下，就能实现这种功效。

  公开号：

  US20140142307A1

文献信息

• Copper promoted synthesis of substituted quinolines from benzylic azides and alkynes
  作者：Ching-Zong Luo、Parthasarathy Gandeepan、Yun-Ching Wu、Wei-Chen Chen、Chien-Hong Cheng

  DOI：10.1039/c5ra23065a

  日期：——

  novel copper promoted synthesis of substituted quinolines from various benzylic azides and internal alkynes has been demonstrated. The reaction features a broad substrate scope, high product yields and excellent regioselectivity. In contrast to the known two-step process of acid promoted [4 + 2] cycloaddition reaction and oxidation, the present methodology allows the synthesis of quinolines in a single

  已经证明了一种新颖的铜促进的由各种苄基叠氮化物和内部炔烃合成取代喹啉的方法。该反应具有广泛的底物范围，高产物收率和优异的区域选择性。与酸促进[4 + 2]环加成反应和氧化的已知两步方法相比，本方法可在中性反应条件下一步合成喹啉，并可用于合成具有生物活性的6-氯-2,3-二甲基-4-苯基喹啉（抗寄生虫剂）和3,4-二苯基喹啉-2（1 H）-one（p38αMAP激酶抑制剂）。可能的反应机理涉及将叠氮化苄重排至N-芳基丙氨酸（Schmidt反应），然后与内部炔烃进行分子间[4 + 2]环加成反应。
• Synthesis and spectroscopic properties of 1,4-diarylbutenynes
  作者：Alois H. A. Tinnemans、Wim H. Laarhoven

  DOI：10.1039/p29760001104

  日期：——

  Several new diarylbutenynes have been synthesized and analyses of the n.m.r. and u.v. spectra are described. For planar trans-isomers a conformational preference was found for 1-(α-naphthyl)- but not for 1-(β-naphthyl)-4-arylbutenynes. This difference is also found between compounds with C-1 attached to the α- or β-position of a larger aryl group.

  已经合成了几种新的二芳基丁烯炔，并描述了nmr和uv光谱的分析。对于平面反式异构体，发现构型偏爱于1-（α-萘基）-，而不是1-（β-萘基）-4-芳基丁烯。在C-1连接到较大芳基的α-或β-位置的化合物之间也发现了这种差异。
• Mercapto-acylamino acid antihypertensives
  申请人：Schering Corporation

  公开号：US05061710A1

  公开（公告）日：1991-10-29

  Novel mercapto-acylamino acids useful in the treatment of hypertension and combinations of mercapto-acylamino acids and atrial natriuretic factors or angiotensin converting enzyme inhibitors useful for treating hypertension are disclosed.

  新型巯基-酰胺基酸在治疗高血压方面很有用，公开了巯基-酰胺基酸和心房利钠因子或抑制血管紧张素转化酶的组合物，用于治疗高血压。
• A Unified Catalytic Asymmetric (4+1) and (5+1) Annulation Strategy to Access Chiral Spirooxindole‐Fused Oxacycles
  作者：Min Gao、Yanshu Luo、Qianlan Xu、Yukun Zhao、Xiangnan Gong、Yuanzhi Xia、Lin Hu

  DOI：10.1002/anie.202105282

  日期：2021.9

  A unified catalytic asymmetric (N+1) (N=4, 5) annulation reaction of oxindoles with bifunctional peroxides has been achieved in the presence of a chiral phase-transfer catalyst (PTC). This general strategy utilizes peroxides as unique bielectrophilic four- or five-atom synthons to participate in the C−C and the subsequent umpolung C−O bond-forming reactions with one-carbon unit nucleophiles, thus providing

  在手性相转移催化剂 (PTC) 的存在下，已经实现了羟吲哚与双官能过氧化物的统一催化不对称 ( N +1) ( N =4, 5) 环化反应。这种通用策略利用过氧化物作为独特的双亲电四原子或五原子合成子参与 C−C 和随后与单碳单元亲核试剂的 umpolung C−O 键形成反应，从而提供了一种独特的方法来获得有价值的手性螺吲哚-四氢呋喃和-四氢吡喃在温和条件下具有良好的产率和高对映选择性。进行 DFT 计算以合理化高对映选择性的起源。还证明了所得产物的克级合成和合成效用。
• NNN-pincer-copper complex immobilized on magnetic nanoparticles as a powerful hybrid catalyst for aerobic oxidative coupling and cycloaddition reactions in water
  作者：Nasrin Zohreh、Mahboobeh Jahani

  DOI：10.1016/j.molcata.2016.11.007

  日期：2017.1

  such as SEM, TEM, FT-IR, TGA, ICP, XRD, and elemental analysis. The finely engineered supported catalyst is employed in the aerobic oxidative coupling of terminal alkynes and click reaction using only 0.38 and 0.04 mol% catalyst, respectively. All reactions perform under solvent-free condition or green solvent H 2 O. Also, the catalyst is readily recovered and reused for up to 8 and 6 subsequent runs

  摘要 描述了一种简单可靠的方法，用于制备第一个对表面组成具有高度控制的非均相 NNN-钳形铜杂化催化剂。该策略依赖于 2-氨基吡啶与三聚氯氰功能化磁性纳米粒子的共价键合，然后与 CuI 络合。这些声明通过不同的表征方法得到证实，例如 SEM、TEM、FT-IR、TGA、ICP、XRD 和元素分析。精细设计的负载型催化剂用于末端炔烃的有氧氧化偶联和点击反应，分别仅使用 0.38 和 0.04 mol% 的催化剂。所有反应均在无溶剂条件或绿色溶剂 H 2 O 下进行。此外，

表征谱图