3,5-二苄氧基苄溴 | 24131-32-6

• 物质功能分类: 化学试剂 - 有机试剂 - 醚类
• 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: 3,5-二苄氧基苄溴
• 中文别名: 3,5-二(苄氧基)苄溴；3,5-二苄氧基-α-溴甲苯；3,5-双(苄氧基)苄溴
• 英文名称: 3,5-bis(benzyloxy)benzyl bromide
• 英文别名: 3,5-dibenzyloxybenzyl bromide；1,3-bis-benzyloxy-5-bromomethylbenzene；1-(bromomethyl)-3,5-bis(phenylmethoxy)benzene
• CAS: 24131-32-6
• 化学式: C₂₁H₁₉BrO₂
• 分子量: 383.285
• InChiKey: WGMYJGAUAQXYFQ-UHFFFAOYSA-N

物化性质

• 熔点：
  86-88
• 沸点：
  504.3±45.0 °C(Predicted)
• 密度：
  1.329±0.06 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2909309090
• 储存条件：
  | 冰箱 |

SDS

Revision number: 1
3,5-Dibenzyloxybenzyl Bromide
SAFETY DATA SHEET

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Section 1. BASE INFORMATION
3,5-Dibenzyloxybenzyl Bromide
Product name:

1
Revision number:

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Section 2. HAZARDS IDENTIFICATION
Classification of the GHS
Not classified
PHYSICAL HAZARDS
HEALTH HAZARDS
Category 1C
Skin corrosion/irritation
Category 1
Serious eye damage/eye irritation
Not classified
ENVIRONMENTAL HAZARDS
GHS label elements
Pictograms or hazard symbols
Danger
Signal word
Causes severe skin burns and eye damage
Hazard statement
Precautionary statements
Do not breathe.
[Prevention]
Wash hands thoroughly after handling.
Wear protective gloves/eye protection/face protection.
IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for
[Response]
breathing.
IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses,
if present and easy to do. Continue rinsing.
IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse
skin with water/shower.
Wash contaminated clothing before reuse.
Immediately call a POISON CENTER or doctor/physician.
Store locked up.
[Storage]
Dispose of contents/container through a waste management company authorized by
[Disposal]
the local government

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance
Substance/mixture:
3,5-Dibenzyloxybenzyl Bromide
Component(s):
>98.0%(GC)(T)
Percent:
24131-32-6
CAS Number:
3,5-Bis(benzyloxy)benzyl Bromide , 3,5-Dibenzyloxy-α-bromotoluene
Synonyms:
C21H19BrO2
Chemical Formula:
3,5-Dibenzyloxybenzyl Bromide

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Section 4. FIRST AID MEASURES
Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Inhalation:
Immediately call a POISON CENTER or doctor/physician.
Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
Skin contact:
soap and water. Immediately call a POISON CENTER or doctor/physician.
Rinse cautiously with water for several minutes. Remove contact lenses, if present
Eye contact:
and easy to do. Continue rinsing.Immediately call a POISON CENTER or
doctor/physician.
Immediately call a POISON CENTER or doctor/physician. Rinse mouth. Do NOT
Ingestion:
induce vomiting.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Dry chemical, foam, water spray, carbon dioxide.
Suitable extinguishing
media:
Take care as it may decompose upon combustion or in high temperatures to
Specific hazards:
generate poisonous fume.
Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
Specific methods:
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
When extinguishing fire, be sure to wear personal protective equipment.
Special protective
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Use extra personal protective equipment (P3 filter respirator for toxic particles). Keep
Personal precautions,
protective equipment and people away from and upwind of spill/leak. Entry to non-involved personnel should
emergency procedures: be controlled around the leakage area by roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Handling
Handling is performed in a well ventilated place. Wear suitable protective equipment.
Technical measures:
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a closed system if possible. Use a local exhaust if dust or aerosol will be
generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Storage
Keep container tightly closed. Store in a refrigerator.
Storage conditions:
Store locked up.
Store away from incompatible materials such as oxidizing agents.
Law is followed.
Packaging material:

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Install a closed system or local exhaust. Also install safety shower and eye bath.
Engineering controls:
Personal protective equipment
Respiratory protection: Dust respirator, self-contained breathing apparatus(SCBA), supplied air respirator,
etc. Use respirators approved under appropriate government standards and follow
local and national regulations.
Impervious gloves.
Hand protection:
Safety goggles. A face-shield, if the situation requires.
Eye protection:
Skin and body protection: Impervious protective clothing. Protective boots, if the situation requires.
3,5-Dibenzyloxybenzyl Bromide

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Solid
Physical state (20°C):
crystal - powder
Form:
White - Very pale yellow
Color:
No data available
Odor:
pH: No data available
Melting point/freezing point:87 °C
No data available
Boiling Point/Range:
No data available
Flash Point:
Explosive limits
No data available
Lower:
No data available
Upper:
No data available
Density:
No data available
Solubility:

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Section 10. STABILITY AND REACTIVITY
Stable under proper conditions.
Stability:
No special reactivity has been reported.
Reactivity:
Heat-sensitive
Conditions to avoid:
Incompartible materials: oxidizing agents
Hazardous Decomposition Carbon monoxide, Carbon dioxide, Hydrogen bromide
Products:

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Section 11. TOXICOLOGICAL INFORMATION
No data available
Acute Toxicity:
Skin corrosion/irritation: No data available
No data available
Serious eye
damage/irritation:
No data available
Germ cell mutagenicity:
Carcinogenicity:
No data available
IARC =
No data available
NTP =
No data available
Reproductive toxicity:

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
No data available
Fish:
No data available
Crustacea:
No data available
Algae:
Persistence / degradability: No data available
No data available
Bioaccumulative
potential(BCF):
Mobillity in soil
No data available
log Pow:
No data available
Soil adsorption (Koc):
No data available
Henry's Law
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
8: Corrosive.
Hazards Class:
1759
UN-No:
3,5-Dibenzyloxybenzyl Bromide

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Section 14. TRANSPORT INFORMATION
Corrosive solid, n.o.s.
Proper shipping name:
III
Packing group:

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26,
2002): Safe use and production, the storage of a dangerous chemical, transport, loading and unloading were
prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  3,5-二苄氧基苄溴 在 sodium methylate 、 三溴化磷 作用下， 以 二氯甲烷 、 环己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 白皮杉醇
  参考文献：
  名称：

  Dimerization of piceatannol by Momordica charantia peroxidase and α-glucosidase inhibitory activity of the biotransformation products

  摘要：

  Stilbenes, especially those oligomers, have great potential to be antihyperglycemic agents. In this study, eight stilbene dimers, including five new ones, were obtained by biotransformation of piceatannol using Momordica charantia peroxidase (MCP) for the first time. Their structures were established on the basis of spectroscopic evidences. These piceatannol dimers displayed potential a-glucosidase inhibitory activities, and trans double bond, tetrahydrofuran ring, and free adjacent phenolic dihydroxyls were found to be important for their activities. Enzymatic biotransformation of stilbenes by M. charantia peroxidase (MCP) was showed to be a prominent way to produce oligomeric stilbenes for antihyperglycemic development. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.07.032
• 作为产物：
  描述：

  3,5-二羟基苯甲酸 在 lithium aluminium tetrahydride 、 18-冠醚-6 、 四溴化碳 、 硫酸 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 4.5h， 生成 3,5-二苄氧基苄溴
  参考文献：
  名称：

  末端官能酰胺基团的疏松度对低聚（对苯撑亚乙烯基）π胶凝剂的光学，胶凝和形态学性质的影响

  摘要：

  本文中，我们描述了末端官能团在具有不同末端基团的酰胺官能化低聚对苯撑亚乙烯基（OPV）胶凝剂的自组装中的作用。氢键和π堆积相互作用之间的相互作用受末端官能团的庞大程度的控制，从而导致形成不同类型的聚集体，从而导致多种溶剂的凝胶化。具有小端基的胶凝剂的可变温度UV / Vis吸收和荧光光谱特征表明在CHCl 3中形成了一维H型聚集体。但是，在甲苯中快速冷却后，形成了1D H型聚集体，而缓慢冷却则导致了2D H型聚集体。具有庞大的树枝状末端基团的OPV酰胺在甲苯中形成氢键结合的无规聚集体，并在THF中观察到从囊泡到纤维聚集体的形态转变。有趣的是，庞大的端基的存在增强了干凝胶状态下的荧光并在极性溶剂中聚集。具有小的和庞大的端基的OPV酰胺的聚集特性之间的差异允许制备具有独特的形态和光学特征的自组装结构。

  DOI：

  10.1002/asia.201402235

文献信息

• Preparation and Chiroptical Studies of Dendritic Alkaloid Derivatives
  作者：Uwe Hahn、Astrid Kaufmann、Martin Nieger、Ondřej Julínek、Marie Urbanova、Fritz Vögtle

  DOI：10.1002/ejoc.200500819

  日期：2006.3

  A series of dendritic substituted alkaloids, deriving from quinine or atropine and Frechet-type dendrons up to generation three, have been prepared. Enantioseparation of the dendronized atropine ammonium salts was achieved by HPLC on chiral stationary phases. Investigation of the chiroptical properties of the series of dendrimers by circular dichroism spectroscopy revealed an influence of the chiral

  一系列树突取代的生物碱，从奎宁或阿托品和 Frechet 型树突衍生到第三代，已被制备出来。树枝状阿托品铵盐的对映分离是通过 HPLC 在手性固定相上实现的。通过圆二色光谱对一系列树枝状聚合物的手性光学特性的研究揭示了手性核对树枝状部分的影响，与棉花带的强度有关。发现手性取决于其手性元素和附着在手性核上的正式非手性树突分支的产生（“树突效应”）。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Assembled Dendritic Titanium Catalysts for Enantioselective Hetero-Diels–Alder Reaction of Aldehydes with Danishefsky's Diene
  作者：Baoming Ji、Yu Yuan、Kuiling Ding、Jiben Meng

  DOI：10.1002/chem.200305286

  日期：2003.12.15

  titanium-catalyzed hetero-Diels-Alder reaction of Danishefsky's diene with aldehydes. These reactions afforded the corresponding 2-substituted 2,3-dihydro-4H-pyran-4-ones in quantitative yields and with excellent enantioselectivities (up to 97.2 % ee). The disposition of the dendritic wedges and the dendron size in the ligands were found to have significant impact on the enantioselectivity of the reaction. The recovered

  合成了一种新型的树枝状2-氨基-2'-羟基-1,1'-联萘（NOBIN）衍生的席夫碱配体，并将其应用于Danishefsky's二烯与醛的钛催化杂Diels-Alder反应。这些反应以定量产率提供了相应的2-取代的2，3-二氢-4H-吡喃-4-酮，并具有优异的对映选择性（高达97.2％ee）。发现在配体中树枝状楔的位置和树枝状分子的大小对反应的对映选择性具有显着影响。回收的树枝状催化剂可以重复使用，而无需进一步添加Ti源或羧酸添加剂至少三个循环，保持了相似的活性和对映选择性。这种组装的树枝状钛催化剂的高稳定性可能归因于催化剂分子中大尺寸树枝状单元的稳定作用。用该催化剂体系观察到的另一个重要现象是，通过将树枝状单元连接到手性配体上，实现了更高程度的不对称扩增，这代表了树枝状聚合物催化剂用于使用较低光学纯度的手性配体进行不对称反应的新优势。
• Novel Dendritic Ligands of Chiral 1,2-Diamine and Their Application in Asymmetric Hydrogenation of Simple Aryl Ketones<b />
  作者：Jingen Deng、Weiguo Liu、Xin Cui、Linfeng Cun、Jun Wu、Jin Zhu、Qinghua Fan

  DOI：10.1055/s-2005-869862

  日期：——

  Novel dendritic chiral vicinal diamine ligands have been synthesized and a series of dendritic Ru(BINAP)(diamine) catalysts were developed for asymmetric hydrogenation of a variety of simple aryl ketones in good catalyticactivity and high enantioselectivity, as well as facile catalyst recycling. An increase of enantio-selectivities was obtained by using the dendritic catalysts compared with Noyori

  合成了新型树枝状手性邻位二胺配体，并开发了一系列树枝状 Ru(BINAP)(二胺) 催化剂，用于多种简单芳基酮的不对称氢化，具有良好的催化活性和高对映选择性，以及催化剂的方便回收。在相同条件下，在几种底物的情况下，与 Noyori 催化剂相比，通过使用树枝状催化剂获得了对映选择性的增加。同时，观察到对催化活性和对映选择性以及再利用的显着结构影响。
• Alternative convergent and accelerated double-stage convergent approaches towards functionalized dendritic polyethers
  作者：B. Forier、W. Dehaen

  DOI：10.1016/s0040-4020(99)00566-9

  日期：1999.8

  Alternative convergent synthesis strategies for the preparation of dendritic macromolecules, using either mesylate activation or the Mitsunobu reaction, are described. The synthesis can be further accelerated by using a double stage convergent approach. Two t-butyldiphenylsilyl protected synthons3 and5 were prepared in excellent yields and used in a one-pot synthesis of higher generation polyether

  描述了使用甲磺酸酯活化或Mitsunobu反应制备树突状大分子的其他收敛合成策略。通过使用双阶段收敛方法可以进一步加速合成。以优异的产率制备了两个叔丁基二苯基甲硅烷基保护的合成子3和5，并将其用于一锅法合成更高一代的聚醚树突。另外，这些合成子被用于制备在外围具有官能团的树突。图选项
• Chemical synthesis and evaluation of 17α-alkylated derivatives of estradiol as inhibitors of steroid sulfatase
  作者：Diane Fournier、Donald Poirier

  DOI：10.1016/j.ejmech.2011.06.027

  日期：2011.9

  Steroid sulfatase (STS) controls the levels of 3-hydroxysteroids available from circulating steroid sulfates in several normal and malignant tissues. This and the known involvement of active estrogens and androgens in diseases such as breast and prostate cancers thus make STS an interesting therapeutic target. Here we describe the chemical synthesis and characterization of an extended series of 17α-derivatives

  类固醇硫酸酯酶（STS）控制着几种正常和恶性组织中循环的类固醇硫酸盐中3-羟基类固醇的水平。因此，已知的活性雌激素和雄激素参与了乳腺癌和前列腺癌等疾病，使STS成为有趣的治疗靶标。在这里，我们描述了使用不同策略的一系列扩展的雌二醇（E2）17α衍生物的化学合成和表征。with-巴比尔反应的一种变体与化学计量的metal金属和催化Kagan试剂的形成被用于在雌酮（E1）的17位引入低反应性苄基底物，而杂环底物则被金属化并与羰基或17-环氧乙烷反应E1。体外 对新化合物对STS的抑制能力的评估确定了新的抑制剂，并允许对该E2的17α衍生物家族进行更完整的结构-活性关系研究。