2-溴-1-(5-溴-1-苯并呋喃-2-基)-1-乙酮 | 7039-76-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 2-溴-1-(5-溴-1-苯并呋喃-2-基)-1-乙酮
• 英文名称: 2-bromo-1-(5-bromo-1-benzofuran-2-yl)ethanone
• 英文别名: 2-bromo-1-(5-bromobenzofuran-2-yl)ethanone；2-Bromo-1-(5-bromo-1-benzofuran-2-yl)-1-ethanone
• CAS: 7039-76-1
• 化学式: C₁₀H₆Br₂O₂
• 分子量: 317.964
• InChiKey: CWMRSJWOSLJADM-UHFFFAOYSA-N

物化性质

• 熔点：
  140 °C
• 沸点：
  360.9±27.0 °C(Predicted)
• 密度：
  1.901±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2932999099

SDS

Name:	2-Bromo-1-(5-bromobenzo[b]furan-2-yl)ethanone Material Safety Data Sheet
Synonym:
CAS:	7039-76-1

Section 1 - Chemical Product MSDS Name:2-Bromo-1-(5-bromobenzo[b]furan-2-yl)ethanone Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
7039-76-1	2-Bromo-1-(5-bromobenzo[b]furan-2-yl)e	90+%	unlisted

Hazard Symbols: C
Risk Phrases: 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Causes burns.
Potential Health Effects
Eye:
Causes eye burns.
Skin:
Causes skin burns.
Ingestion:
Causes gastrointestinal tract burns.
Inhalation:
Causes chemical burns to the respiratory tract.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately.
Skin:
Get medical aid immediately. Immediately 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 immediately.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
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 foam, dry chemical, or carbon dioxide.

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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:
Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Corrosives area.

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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# 7039-76-1: 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: 135 - 136 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: C10H6Br2O2
Molecular Weight: 317.97

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents, reducing agents, amines.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide, hydrogen bromide, bromine.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 7039-76-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Bromo-1-(5-bromobenzo[b]furan-2-yl)ethanone - 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: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.*
Hazard Class: 8
UN Number: 3261
Packing Group: III
IMO
Shipping Name: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3261
Packing Group: III
RID/ADR
Shipping Name: CORROSIVE SOLID, ACIDIC, ORGANIC, N.O.S.
Hazard Class: 8
UN Number: 3261
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 34 Causes burns.
Safety Phrases:
S 22 Do not breathe dust.
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 7039-76-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 7039-76-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 7039-76-1 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：

  2-溴-1-(5-溴-1-苯并呋喃-2-基)-1-乙酮 在 novozyme 435 、 18-冠醚-6 作用下， 以 乙醇 为溶剂， 生成 (1R)-1-acetoxy-1-(5-bromobenzofuran-2-yl)ethane
  参考文献：
  名称：

  Optically active 1-(benzofuran-2-yl)ethanols and ethane-1,2-diols by enantiotopic selective bioreductions

  摘要：

  Enantiotopic selective reduction of 1-(benzofuran-2-yl)ethanones 1a-d, 1-(benzofuran-2-yl)-2-hydroxyethanones 4a-c and 2-acetoxy-1-(benzofuran-2-yl)ethanones 3a-c was performed by baker's yeast for preparation of optically active (benzofuran-2-yl)carbinols [(S)-5a-d, (S)-6a-c and (R)-6a-c, enantiomeric excess from 55 to 93% ee]. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00222-2
• 作为产物：
  描述：

  2-乙酰基-5-溴苯并[b]呋喃 在 溴 、 溶剂黄146 作用下， 以76%的产率得到2-溴-1-(5-溴-1-苯并呋喃-2-基)-1-乙酮
  参考文献：
  名称：

  基于喹唑啉酮、苯并呋喃和咪唑鎓部分的生物活性杂环杂化物：合成、表征、细胞毒性和抗菌评价

  摘要：

  已经设计和合成了结构上基于喹唑啉酮、苯并呋喃和咪唑药效团的细胞毒性剂和抗微生物剂。光谱 (IR, 1H-NMR) 和元素分析数据确定了这些新型 3-[1-(1-benzofuran-2-yl)-2-(4-oxoquinazolin-3(4H)-yl)ethyl]-的结构1-甲基-1H-咪唑-3-氯化鎓杂化衍生物。所有合成的化合物都进行了体外细胞毒性和抗菌活性的评估。使用 MTT 测定的细胞毒性评估表明，化合物 12c、12g 和 12i 显示出显着的细胞毒性，IC50 值分别为 1、1 和 0.57 μm。还评估了合成化合物作为抗菌剂的生物活性，针对三种革兰氏阴性菌（大肠杆菌、铜绿假单胞菌和伤寒沙门氏菌），三种革兰氏阳性菌（金黄色葡萄球菌、枯草芽孢杆菌和李斯特菌）和一种酵母样真菌（白色念珠菌）菌株。所有化合物 12a-12i 对革兰氏阳性菌的活性均略高于革兰氏阴性菌。在筛选的 9 种新化合

  DOI：

  10.1002/cbdv.201600411

文献信息

• Reaction with Hydrazonoyl Halides 64: Synthesis of Some New Triazolino[4,3-<i>a</i>]pyrimidines, 1,3,4-Thiadiazoles, and 5-Arylazothiazoles
  作者：Abdou O. Abdelhamid、Abdelgawad A. Fahmi、Basma S. Baaui

  DOI：10.1002/jhet.945

  日期：2012.9

  benzofuran moiety were prepared from the reaction of 2‐(2‐phenylhydrazono)‐1‐(5‐bromobenzofuran‐2‐yl)‐2‐chloroethanone with each of potassium thiocyanate, potassium selenocyanate, alkyl carbodithioate, and pyrmidine‐2‐thione derivatives. All the newly synthesized compounds were confirmed by elemental analysis, spectral data, and alternative route synthesis whenever possible.

  由2-（-）的反应制得2,3-二氢-1,3,4-噻二唑，2,3-二氢-1,3,4-硒代二唑和含苯并呋喃部分的三唑啉并[4,3- a ]嘧啶。 2-苯基肼基）-1-（5-溴苯并呋喃-2-基）-2-氯乙酮与硫氰酸钾，硒氰酸钾，碳二硫代烷基酯和嘧啶-2-硫酮衍生物中的每一种。所有新合成的化合物均通过元素分析，光谱数据和可能的替代路线合成得到确认。
• Synthesis and bioactivity of novel C2-glycosyl benzofuranylthiazoles derivatives as acetylcholinesterase inhibitors
  作者：Lei Wang、Yu-Ran Wu、Shu-Ting Ren、Long Yin、You-Xian Wang、Shu-Hao Liu、Wei-Wei Liu、Da-Hua Shi、Zhi-Ling Cao、Hui-Min Sun

  DOI：10.1177/1747519819856973

  日期：2019.7

  A new series of C2-glycosyl benzofuranylthiazole derivatives was synthesised by the further cyclization of glycosyl thiourea and 2-(bromoacetyl)-benzofuran via Hantzsch’s method. The corresponding 2-(bromoacetyl)-benzofuran derivatives were obtained by the reaction from various salicylaldehydes, and the glycosyl thiourea was prepared through a series of steps from D-Glucosamine. The acetylcholinesterase-inhibitory

  通过Hantzsch法进一步环化糖基硫脲和2-(溴乙酰基)-苯并呋喃，合成了一系列新的C2-糖基苯并呋喃基噻唑衍生物。由各种水杨醛反应得到相应的2-(溴乙酰基)-苯并呋喃衍生物，由D-氨基葡萄糖通过一系列步骤制备糖基硫脲。产品的乙酰胆碱酯酶抑制活性通过 Ellman 方法测试。随后评估了最具活性的化合物的 50% 抑制浓度值。N-(1,3,4,6-四-O-苄基-2-脱氧-β-D-吡喃葡萄糖基)-4-(5-甲氧基-苯并呋喃-2-基)-1,3-噻唑-2-胺具有最佳的乙酰胆碱酯酶抑制活性，50% 抑制浓度为 2.03 ± 0.26 μM。
• Synthesis and Evaluation of Antimicrobial Activity of Some Novel Heterocyclic Compounds from 5-Bromosalicylaldehyde
  作者：Anhar Abdel-Aziem、Basma S. Baaiu、Abdou O. Abdelhamid

  DOI：10.1002/jhet.2970

  日期：2017.11

  21–24 were synthesized from the reaction of chalcone 18 with different active methylene compounds. Reaction of 24 with ethylchloroacetate, chloroacetone, and chloroacetonitrile afforded thienopyridines 26a–c, respectively. The structures of the newly synthesized compounds were established based on their spectral data and elemental analyses. Also, selected newly synthesized compounds were screened for their

  通过5-溴水杨醛与不同试剂的反应合成了一系列香豆素，噻二唑，噻唑和吡啶。因此，5-溴水杨醛1与化合物反应图2a-d得到iminocoumarins图3a-d ，将其用10％的盐酸，得到香豆素水解图4a-d ，分别。另一方面，1与苄肼碳二硫代酸酯5的反应得到衍生物6，后者与卤代酰卤7a-f反应，分别得到1,3,4-噻二唑11a-f。此外，噻唑15和16通过1与硫代碳酰肼13和酰肼基卤化物的反应获得。但是，将2-乙酰基-5-溴苯并呋喃17与苯甲醛缩合，得到查尔酮18，查尔酮18与溴化吡啶鎓19a–c反应，分别得到吡啶20a–c。此外，吡啶酮21-24由查尔酮18与不同的活性亚甲基化合物反应合成。反应24与ethylchloroacetate，氯丙酮，和氯噻吩并吡啶提供26A-C， 分别。根据新合成的化合物的光谱数据和元素分析，确定了它们的结构。而且，通过盘扩散法筛选了选定的新合成的化合物对各种微生物的抗微生物活性。
• Chemo-enzymatic preparation of hydroxymethyl ketones
  作者：Csaba Paizs、Monica Toşa、Cornelia Majdik、Viktória Bódai、Lajos Novák、Florin-Dan Irimie、László Poppe

  DOI：10.1039/b206851f

  日期：——

  A series of hydroxymethyl ketones 4a–g were obtained from the corresponding halogenomethyl ketones 2a–gvia their transformation into acetoxymethyl ketones 3a–g by 18-crown-6 catalysed substitution with NaOAc followed by Novozyme 435™ catalysed ethanolysis. This convenient chemo-enzymatic route provides a mild, heavy-metal-free alternative to the direct α-hydroxylations of methyl ketones 1a–g.

  一系列的 羟甲基 酮类 4a–g是从相应的卤代甲基获得的酮类 2a–g通过转化为乙酰氧基甲基酮类 图3a-克由18冠6 NaOAc催化的取代反应，随后由Novozyme 435™催化 乙醇分解。这种方便的化学酶促途径为甲基酮1a–g的直接α-羟基化提供了温和，不含重金属的替代方法。
• Preparation of leukotriene B4 inhibitory active 2- and 3-(2-aminothiazol-4-yl)benzo[b]furan derivatives and their growth inhibitory activity on human pancreatic cancer cells
  作者：Mari Kuramoto、Yoko Sakata、Kumi Terai、Ikuo Kawasaki、Jun-ichi Kunitomo、Takahiro Ohishi、Takehiko Yokomizo、Seiichi Takeda、Shuichi Tanaka、Yoshitaka Ohishi

  DOI：10.1039/b803313g

  日期：——

  A series of 2-(2-aminothiazol-4-yl)benzo[b]furan and 3-(2-aminothiazol-4-yl)benzo[b]furan derivatives were prepared, and their leukotriene B4 inhibitory activity and growth inhibitory activity in cancer cell lines were evaluated. Several compounds showed strong inhibition of calcium mobilization in CHO cells overexpressing human BLT1 and BLT2 receptors and growth inhibition to human pancreatic cancer cells MIA PaCa-2. 3-(4-Chlorophenyl)-2-[5-formyl-2-[(dimethylamino)methyleneamino]thiazol-4-yl]-5-methoxybenzo[b]furan 8b showed the most potent and selective inhibition for the human BLT2receptor, and its IC50 value was smaller than that of the selected positive control compound, ZK-158252. 3-(4-Chlorophenyl)-2-[2-[(dimethylamino)methyleneamino]-5-(2-hydroxyethyliminomethyl)thiazol-4-yl]-5-methoxybenzo[b]furan 9a displayed growth inhibitory activity towards MIA PaCa-2.

  一系列2-(2-氨基噻唑-4-基)苯并[b]呋喃和3-(2-氨基噻唑-4-基)苯并[b]呋喃衍生物被合成，并评估了它们对白三烯B4的抑制活性及对癌细胞系的生长抑制活性。几个化合物在过表达人类BLT1和BLT2受体的CHO细胞中显示出对钙动员的强抑制作用，并对人类胰腺癌细胞MIA PaCa-2表现出生长抑制。3-(4-氯苯基)-2-[5-甲酰基-2-[(二甲氨基)亚甲基氨基]噻唑-4-基]-5-甲氧基苯并[b]呋喃8b对人类BLT2受体显示出最强且选择性的抑制，其IC50值小于选定的阳性对照化合物ZK-158252。3-(4-氯苯基)-2-[2-[(二甲氨基)亚甲基氨基]-5-(2-羟基乙基亚氨基甲基)噻唑-4-基]-5-甲氧基苯并[b]呋喃9a对MIA PaCa-2显示出生长抑制活性。