2,5-二氯-3-乙酰基噻吩 | 36157-40-1

• 物质功能分类: 医药中间体 - 杂环化合物 - 噻吩类化合物
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2,5-二氯-3-乙酰基噻吩
• 中文别名: 2,5-二氯-3-噻吩基甲基酮；3-乙酰-2,5-二氯噻吩；3-乙酰基-2,5-二氯噻吩
• 英文名称: 3-acetyl-2,5-dichlorothiophene
• 英文别名: 2,5-Dichloro-3-acetylthiophene；1-(2,5-dichlorothiophen-3-yl)ethan-1-one；1-(2,5-dichlorothiophen-3-yl)ethanone
• CAS: 36157-40-1
• 化学式: C₆H₄Cl₂OS
• mdl: MFCD00014522
• 分子量: 195.069
• InChiKey: GYFDNIRENHZKGR-UHFFFAOYSA-N

物化性质

• 熔点：
  37-40 °C (lit.)
• 沸点：
  120-122°C 4mm
• 密度：
  1.4514 (estimate)
• 闪点：
  >230 °F
• 稳定性/保质期：
  常规情况下不会分解，没有危险反应。<?xml:namespace prefix = o ns = "urn:schemas-microsoft-com:office:office" />

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S22,S26,S36,S36/37,S36/37/39
• 危险类别码：
  R20/21/22,R36/37/38
• WGK Germany：
  3
• 海关编码：
  29349990
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H312,H315,H319,H332,H335
• 储存条件：
  密封、阴凉、干燥、通风保存。

SDS

Name:	3-Acetyl-2 5-dichlorothiophene 98% Material Safety Data Sheet
Synonym:	None
CAS:	36157-40-1

Section 1 - Chemical Product MSDS Name:3-Acetyl-2 5-dichlorothiophene 98% Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
36157-40-1	3-Acetyl-2,5-dichlorothiophene	98.0	252-893-3

Hazard Symbols: XN
Risk Phrases: 20/21/22

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
The toxicological properties of this substance have not been fully investigated. May be harmful if swallowed.
Inhalation:
The toxicological properties of this substance have not been fully investigated. May be harmful if inhaled.
Chronic:
No information found.

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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 immediately.
Skin:
Get medical aid immediately. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Wash clothing before reuse.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. 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:
Antidote: None reported.

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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 to cool fire-exposed containers. Use extinguishing media most appropriate for the surrounding fire.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use only in a well-ventilated area. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation.
Storage:
Store in a cool place in the original container and protect from sunlight. Store in a cool, dry, well-ventilated area away from incompatible substances. Keep containers tightly closed.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate general or local explosion-proof ventilation to keep airborne levels to acceptable levels.
Exposure Limits CAS# 36157-40-1: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate 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: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 37 - 40 deg C
Autoignition Temperature: Not available.
Flash Point: > 110 deg C (> 230.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C6H4Cl2OS
Molecular Weight: 195.07

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stability unknown.
Conditions to Avoid:
Incompatible materials, dust generation.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, carbon monoxide, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 36157-40-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3-Acetyl-2,5-dichlorothiophene - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
Safety Phrases:
S 36/37 Wear suitable protective clothing and
gloves.
WGK (Water Danger/Protection)
CAS# 36157-40-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 36157-40-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 36157-40-1 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

制备方法与用途

合成方法：1-甲基-4-氯丁烯醛与强碱反应后，拔掉α位上的活泼氢，再与硫代乙酰氯对接，在60-80摄氏度下加热反应并关环，最终得到目标产物3-乙酰基-2,5-二氯噻吩。

反应信息

• 作为反应物：
  描述：

  2,5-二氯-3-乙酰基噻吩 在 正丁基锂 、 sodium tungstate (VI) dihydrate 、 pyridinium hydrobromide perbromide 、 硫酸 、 氨 、 双氧水 、 氯 、 potassium carbonate 、 三乙胺 、 硫脲 、 (+)-二异松蒎基氯硼烷 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 甲基叔丁基醚 、 水 、 二甲基亚砜 、 乙酸乙酯 、 甲苯 、 乙腈 为溶剂， 反应 86.92h， 生成 布林佐胺
  参考文献：
  名称：

  Enantioselective Synthesis of Brinzolamide (AL-4862), a New Topical Carbonic Anhydrase Inhibitor. The “DCAT Route” to Thiophenesulfonamides

  摘要：

  A large scale synthesis of the topical carbonic anhydrase inhibitors AL-4623A (13a . HCl) and AL-4862 (13b) from 3-acetyl-2,5-dichlorothiophene ("DCAT", 1) is described, Reaction of 1 with NaSBn gave thioether 2, which was converted via sulfenyl chloride 3 and sulfenamide 5 to sulfonamide 6, Bromination of 6 gave bromo ketone 7, which upon reduction with (+)-B-chlorodiisopinocampheylborane and cyclization of the resulting bromohydrin produced S thieno[3,2-e]-1,2-thiazine 8a (96% ee) after chromatography, Treatment of 8a in THF with n-BuLi at -70 degrees C resulted in Li-Cl exchange, Reaction of the thienyllithium with SO2 and hydroxylamine O-sulfonic acid afforded bis-sulfonamide 11a, Protection of 11a as the acetinidate 12a, followed by tosylation and amination, gave R amine 13a, The synthesis of 13b proceeded via primary sulfonamide 16, which was brominated, reduced, and cyclized to give S thieno[3,2-e]-1,2-thiazine 18 (>98% ee). By virtue of the ionizable NH, 18 was separable from reduction byproducts by base extraction. Alkylation of 18 with 3-bromopropyl methyl ether afforded 8b, which was converted as above, via 11b, to AL-4862 (13b), These procedures provided multihundred gram lots of 13a and 13b.

  DOI：

  10.1021/op9802125
• 作为产物：
  描述：

  2,5-二氯噻吩 、 乙酰氯 在 aluminum (III) chloride 作用下， 以 二硫化碳 为溶剂， 以76.7%的产率得到2,5-二氯-3-乙酰基噻吩
  参考文献：
  名称：

  含有噻吩部分的新型查耳酮化合物的结构表征：(E)-3-(5-Bromothiophen-2-YL)-1-(2,5-Dichlorothiophen-3-YL)-2-Propen-1-One

  摘要：

  合成了新型查耳酮衍生物 (E)-3-(5-bromothiophen-2-yl)-1-(2,5-dichlorothiophen-3-yl)-2-propen-1-one 的晶体结构并对其进行了结构表征通过光谱 IR、NMR 和 HRMS 技术。其晶体和分子结构由单晶 X 射线衍射研究确定。该化合物在单斜晶系和空间群 P21/n (N 19) 中结晶。晶体堆积受 C-H...O 非常规氢键型分子间相互作用控制，形成由沿 [010] 方向运行的 21 个螺旋轴相关的扩展锯齿形链，图形集 C(8)。这些氢键有助于稳定晶体结构，其堆积效率为 71.4%。

  DOI：

  10.1134/s0022476618060276
• 作为试剂：
  描述：

  碳酸二甲酯 、 1-(2,4,5-三氯苯基)-1-乙酮 在 2,5-二氯-3-乙酰基噻吩 、 sodium hydride 作用下， 反应 2.0h， 以84%的产率得到methyl 3-oxo-3-(2,4,5-trichlorophenyl)propanoate
  参考文献：
  名称：

  通过异硫氰酸酯稠合硫杂杂环。第一部分. 一些新的 1-苯并噻喃-4-one 衍生物的简便合成

  摘要：

  摘要 通过去质子化 3-氧代-3(2',4',5'-三氯苯基)丙酸甲酯 5 的一锅反应制备了一组精选的新型 4H-苯并噻喃-4-one 衍生物 6a-h。合适的异硫氰酸芳基或烷基酯。合成 5 所需的 2,4,5-三氯苯乙酮 4 是通过 1,2,4-三氯苯的 Friedel-Craft 乙酰化成功制备的，产率为 82%。新化合物 5 和 6a–h 的结构基于微量分析和光谱（NMR、MS(EI) 和 HRMS）数据。

  DOI：

  10.1515/znb-2016-0271

文献信息

• Sulfonamides useful as carbonic anhydrase inhibitors
  申请人：Alcon Laboratories, Inc.

  公开号：US05378703A1

  公开（公告）日：1995-01-03

  Sulfonamides and pharmaceutical compositions containing the compounds useful in controlling intraocular pressure are disclosed. Methods for controlling intraocular pressure through administration of the compositions are also disclosed.

  磺胺类药物和含有有益于控制眼压的化合物的药物组合物被揭示。还公开了通过给药组合物来控制眼压的方法。
• PROTEIN CROSSLINKING INHIBITOR AND USE OF THE SAME
  申请人：Mikoshiba Katsuhiko

  公开号：US20120277423A1

  公开（公告）日：2012-11-01

  The present invention relates to: a ketone compound having transglutaminase-inhibiting activity, which is represented by the following Formula 1, 2, or 3: wherein R 1 is a substituted or unsubstituted aryl or heterocyclyl group, R 2 , R 3 , and R 4 are hydrogen atoms, n is 2, X is halogen, R 5 and R 6 independently represent a hydrogen atom or a substituted or unsubstituted C1-C10 alkyl, aryl, or aralkyl group, wherein R 5 and R 6 are not hydrogen atoms at the same time, or R 5 and R 6 may be taken together to form a saturated or unsaturated and substituted or unsubstituted heterocyclyl group containing a nitrogen atom (N); an inhibitor of protein crosslinking comprising the compound; and a composition for preventing or treating a protein-crosslinking causative disease, which comprises the compound or the protein crosslinking inhibitor.

  本发明涉及：一种具有转谷氨酰胺酶抑制活性的酮化合物，由下式1、2或3表示： 其中R1是取代或未取代的芳基或杂环基团，R2、R3和R4是氢原子，n是2，X是卤素，R5和R6独立地表示氢原子或取代或未取代的C1-C10烷基、芳基或芳烷基团，其中R5和R6不同时为氢原子，或者R5和R6可以共同形成含氮原子（N）的饱和或未饱和的、取代或未取代的杂环基团；包含该化合物的蛋白质交联抑制剂；以及包含该化合物或蛋白质交联抑制剂的用于预防或治疗由蛋白质交联引起的疾病的组合物。
• Design and synthesis of novel thiopheno-4-thiazolidinylindoles as potent antioxidant and antimicrobial agents
  作者：Jaiprakash Biradar、Parveen Rajesab、B. Sasidhar

  DOI：10.2478/s11696-013-0452-3

  日期：2014.1.1

  obtaining biologically active compounds. 3,5-disubstituted indol-2-carboxyhydrazides (Ia-If) were allowed to react with 3-acetyl-2,5-dichlorothiophene (II) to yield the corresponding 3,5-disubstituted indol-2-carbohydrazides (IIIa-IIIf). The pre-formed indolecarbohydrazides (IIIa-IIIf) were allowed to react with 2-mercaptoacetic acid or 2-mercaptopropanoic acid to produce thiopheno-4-thiazolidinylindoles

  为了获得具有生物活性的化合物，提出了一种新颖且方便的噻吩-4-噻唑啉基吲哚类似物的合成方法（IVa-IVi）。使3,5-二取代的吲哚-2-羧酰肼（Ia-If）与3-乙酰基-2,5-二氯噻吩（II）反应，生成相应的3,5-二取代的吲哚-2-碳酰肼（IIIa-IIIf））。使预先形成的吲哚碳酰肼（IIIa-IIIf）与2-巯基乙酸或2-巯基丙酸反应，生成噻吩-4-噻唑啉基吲哚（IVa-IVi）。该反应方案提供了简单，环保，无害，易于制备和高收率的特点。评价了合成化合物的抗氧化剂（清除自由基，总抗氧化剂能力和还原铁的抗氧化剂能力）和抗菌活性。产物的结构和纯度由它们的IR，1 H NMR，13 C NMR以及质谱和分析数据证实。所测试的大多数化合物都表现出非常重要的清除，抗氧化剂和抗菌活性。在吲哚的第五位上含有电子供体基团（CH 3）的化合物表现出优异的三价铁还原活性。本研究表明化合物IIIa-I
• Process for the preparation of (R)-(+)-4-(Ethylamino)-3,4-dihydro-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide-1,1-dioxide.
  申请人：Sathe Dhananjay Govind

  公开号：US20100009977A1

  公开（公告）日：2010-01-14

  Disclosed herein is an improved process for the preparation of (R)-(+)-4-(Ethylamino)-3,4-dihydro-2-(3-methoxypropyl)-2H-thieno[3,2-e]-1,2-thiazine-6-sulfonamide-1,1-dioxide (Brinzolamide) and novel intermediates thereof.

  本文披露了一种改进的工艺，用于制备(R)-(+)-4-(乙基氨基)-3,4-二氢-2-(3-甲氧基丙基)-2H-噻吩[3,2-e]-1,2-噻嗪-6-磺酰胺-1,1-二氧化物（布林唑胺）及其新颖的中间体。
• Preparation of carbonic anhydrase inhibitors
  申请人：Alcon Laboratories, Inc.

  公开号：US05344929A1

  公开（公告）日：1994-09-06

  A process for synthesizing carbonic anhydrase inhibitors is disclosed.

  揭示了一种合成碳酸酐酶抑制剂的过程。

表征谱图