1-(7-溴-2,3-二氢-1,4-苯并二氧六环-6-基)乙酮 | 59820-90-5

• 物质功能分类: 生物 - 细胞培养 - 培养基
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 中文名称: 1-(7-溴-2,3-二氢-1,4-苯并二氧六环-6-基)乙酮
• 中文别名: 1-(7-溴-2,3-二氢-1,4-苯并二噁英-6-基)-1-乙酮
• 英文名称: 7-acetyl-6-bromo-1,4-benzodioxane
• 英文别名: 1-(7-bromo-2,3-dihydro-1,4-benzodioxan-6-yl)ethanone；1-(7-Bromo-2,3-Dihydro-1,4-Benzodioxin-6-Yl)Ethan-1-One；1-(6-bromo-2,3-dihydro-1,4-benzodioxin-7-yl)ethanone
• CAS: 59820-90-5
• 化学式: C₁₀H₉BrO₃
• 分子量: 257.084
• InChiKey: WBSQNDBQUDSQCV-UHFFFAOYSA-N

物化性质

• 熔点：
  85-87
• 沸点：
  366.9±42.0 °C(Predicted)
• 密度：
  1.548±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2914700090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335

SDS

Name:	1-(7-Bromo-2,3-dihydro-1,4-benzodioxin-6-yl)ethan-1-one, 97% Material Safety Data Sheet
Synonym:	2-Bromo-4,5-ethylenedioxyacetophenone
CAS:	59820-90-5

Section 1 - Chemical Product MSDS Name: 1-(7-Bromo-2,3-dihydro-1,4-benzodioxin-6-yl)ethan-1-one, 97% Material Safety Data Sheet
Synonym: 2-Bromo-4,5-ethylenedioxyacetophenone

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SECTION 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
59820-90-5	1-(7-Bromo-2,3-dihydro-1,4-benzodioxin	97%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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SECTION 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW 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:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
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:
Vacuum or sweep up material and place into a suitable disposal 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# 59820-90-5: 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: Solid
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 85 - 87 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C10H9BrO3
Molecular Weight: 257

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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:
Carbon monoxide, carbon dioxide, hydrogen bromide.
Hazardous Polymerization: Not available.

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SECTION 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 59820-90-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-(7-Bromo-2,3-dihydro-1,4-benzodioxin-6-yl)ethan-1-one - 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 No information available. IMO No information available. RID/ADR No information available.

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SECTION 15 - REGULATORY INFORMATION European/International Regulations European Labeling in Accordance with EC Directives
Hazard Symbols: XI
Risk Phrases:
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# 59820-90-5: No information available. Canada None of the chemicals in this product are listed on the DSL/NDSL list. CAS# 59820-90-5 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 59820-90-5 is not listed on the TSCA inventory. It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
MSDS Creation Date: 6/10/2003 Revision #0 Date: Original. The information above is believed to be accurate and represents the best information currently available to us. However, we make no warranty of merchantability or any other warranty, express or implied, with respect to such information, and we assume no liability resulting from its use. Users should make their own investigations to determine the suitability of the information for their particular purposes. In no way shall the company be liable for any claims, losses, or damages of any third party or for lost profits or any special, indirect, incidental, consequential or exemplary damages, howsoever arising, even if the company has been advised of the possibility of such damages.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  1-(7-溴-2,3-二氢-1,4-苯并二氧六环-6-基)乙酮 在 四(三苯基膦)钯 、 copper(l) cyanide 、 对甲苯磺酸 、 copper(l) chloride 、 sodium t-butanolate 、 1,3-bis(cyclohexyl)imidazolium tetrafluoroborate 作用下， 以 甲苯 为溶剂， 反应 20.5h， 生成
  参考文献：
  名称：

  在抗肿瘤前药开发中通过生物正交环化在细胞内生成抗癌菲啶

  摘要：

  与游离药物相比，抗肿瘤前药平台在 3D 结构中产生显着变化。显示完全无活性的前体通过生物正交环化在肿瘤模型中产生细胞毒性菲啶。在活的癌症球体内，环化动力学很快（<10 ms），以防止药物在肿瘤外形成。

  DOI：

  10.1002/anie.202110041
• 作为产物：
  描述：

  乙酰氯 、 6-溴-1,4-苯并恶烷 在 aluminum (III) chloride 作用下， 以 四氯化碳 为溶剂， 以69%的产率得到1-(7-溴-2,3-二氢-1,4-苯并二氧六环-6-基)乙酮
  参考文献：
  名称：

  o-Acylbenzonitriles: Synthesis and Heterocyclization under Acid Hydrolysis of the Cyano Group

  摘要：

  2-Cyanobenzophenones were synthesized by reaction of 2-bromobenzophenones with copper(I) cyanide in DMF, and their transformations involving acid hydrolysis of the cyano group were studied. Reactions of o-benzoylbenzonitriles with trifluoroacetic acid in the presence or in the absence of sulfuric acid afforded 3-hydroxyphthalimidines in high yields. Under analogous conditions, benzonitriles having no acyl group in the ortho position were converted to the corresponding benzamides. 2-Cyanobenzophenones reacted with sulfuric acid in the absence of trifluoroacetic acid to give only substituted anthraquinones.

  DOI：

  10.1134/s1070428018030065

文献信息

• 一种N,N-二甲基-1-萘胺类化合物的制备方 法
  申请人：湖南大学

  公开号：CN110092724B

  公开（公告）日：2021-08-31

  本发明提供了一种由末端炔烃、邻溴苯乙酮、N,N‑二甲基酰胺类化合物制备N,N‑二甲基‑1‑萘胺类化合物的方法。该方法使用廉价易得的原料和铜催化剂，官能团兼容性强，所得目标产物易分离，反应操作简便，安全可靠，产物产率都很高，该方法解决了其他合成方法中所存在的低产率、底物需要预官能团化及适用性不广、操作复杂、配体、贵重金属、毒害作用的有机溶剂的使用等问题，在荧光探针、染料和生物活性药物上具有潜在的应用前景。
• Cu‐catalyzed synthesis of 1‐naphthols with terminal alkynes and 2‐bromoaryl ketones
  作者：Peng Ma、Yuhang Wang、Jianhui Wang

  DOI：10.1002/aoc.6792

  日期：2022.9

  A Cu-catalyzed straightforward synthesis of 1-naphthols via an 6-endo-dig cyclization of terminal alkynes with 2-bromoaryl ketones in water is reported. The Cu(I) catalytic system tolerates various electron-withdrawing and electron-donating functional groups on both substrates and exhibits unique 6-endo-dig selectivity to give 1-naphthols in moderate to good yields.

  报道了通过末端炔烃与 2-溴芳基酮在水中的 6-endo-dig 环化，Cu 催化直接合成 1-萘酚。Cu(I) 催化体系在两种底物上都能耐受各种吸电子和给电子官能团，并表现出独特的 6-endo-dig 选择性，以中等至良好的产率提供 1-萘酚。
• Process Development of the Synthetic Route to Sulamserod Hydrochloride
  作者：Bruce A. Kowalczyk、Robinson、John O. Gardner

  DOI：10.1021/op0002040

  日期：2001.3.1

  Sulamserod hydrochloride is a potent 5-HT4 receptor antagonist and was a clinical candidate for the treatment of gastrointestinal disorders. Process development of the fairly long synthetic route (12 linear, 14 overall steps) was undertaken. Process improvements were highlighted by aromatic chlorination choices in making dichlorobenzodioxan 2 and acetylaminochloroketone 7, a transfer hydrogenation reducing a nitro group and simultaneous aromatic dechlorination without ketone reduction to give aminoketone 5, and use of the potential mutagenic iodosulfonamide 14 to make quaternary salt 11. The chemistry was scaled up into pilot plant reactor vessels to produce multikilogram amounts of Sulamserod hydrochloride suitable for drug development.
• DAUKSHAS V. K.; UDRENAJTE EH. B., LIETTSR AUKSTUJU. MOKUKLU MOKSLO DARVAI. CHEMIJA IR CHEM. TESNNOL., NAUCH+
  作者：DAUKSHAS V. K.、 UDRENAJTE EH. B.

  DOI：——

  日期：——
• Synthesis of 6-methylphenanthridines and evaluation against human papillomavirus-related endocervical adenocarcinoma (KB 3.1) cells
  作者：Hichem Maslah、Charles Skarbek、Raphaël Labruère

  DOI：10.1016/j.phytol.2023.02.012

  日期：2023.4