4-(4-溴苯基)-2-噻唑乙腈 | 94833-31-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-(4-溴苯基)-2-噻唑乙腈
• 中文别名: [4-(4-溴苯基)-1,3-噻唑-2-基]乙腈
• 英文名称: 4-bromophenyl-2-thiazoleacetonitrile
• 英文别名: 4-(4-bromophenyl)thiazol-2-ylacetonitrile；2-(4-(4-bromophenyl)thiazol-2-yl)acetonitrile；2-[4-(4-bromophenyl)-1,3-thiazol-2-yl]acetonitrile；4-(4-Bromphenyl)-2-cyanomethylthiazol；4-(4-Bromophenyl)-2-thiazoleacetonitrile
• CAS: 94833-31-5
• 化学式: C₁₁H₇BrN₂S
• mdl: MFCD00551793
• 分子量: 279.16
• InChiKey: VBHJUUAUIGGAPS-UHFFFAOYSA-N

物化性质

• 熔点：
  125-129 °C (lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  64.9
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  T
• 危险类别码：
  R25,R41,R37/38
• 危险品运输编号：
  UN 2811 6.1/PG 3
• 海关编码：
  2934100090
• 安全说明：
  S26,S36/37/39,S45
• WGK Germany：
  3
• 危险标志：
  GHS05,GHS06
• 危险性描述：
  H301,H315,H318,H335
• 危险性防范说明：
  P261,P280,P301 + P310,P305 + P351 + P338

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
4-(4-Bromophenyl)-2-thiazoleacetonitrile
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H301: Toxic if swallowed
H315: Causes skin irritation
H318: Causes serious eye damage
H335: May cause respiratory irritation
Avoid breathing dust/fume/gas/mist/vapours/spray
P261:
P280: Wear protective gloves/protective clothing/eye protection/face protection
P301+P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing

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Section 3. Composition/information on ingredients.
4-(4-Bromophenyl)-2-thiazoleacetonitrile
Ingredient name:
CAS number: 94833-31-5

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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.

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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.

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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.

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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.

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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: C11H7BrN2S
Molecular weight: 279.2

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

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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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.

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Section 14. Transportation information
UN Number: UN2811 Class: 6.1 Packing group: III
Proper shipping name: TOXIC SOLIDS, ORGANIC, N.O.S. (4-(4-Bromophenyl)-2-thiazoleacetonitrile)

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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.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-(4-溴苯基)-2-噻唑乙腈 在 吡啶 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 5-amino-4-[4-(4-bromophenyl)-1,3-thiazol-2-yl]-1-(4-piperidin-1-ylphenyl)-2H-pyrrol-3-one
  参考文献：
  名称：

  摘要：

  Reactions of 2-(4-aryl-1,3-thiazol-2-yl)-3-oxo-4-chlorobutyronitriles with primary aromatic amines result in nucleophilic substitution of the chlorine atom by amino group, followed by intramolecular addition of the secondary amino group to the cyano group. The products are 5-amino-1-aryl-4-(4-aryl-1,3-thiazol-2-yl)2,3-dihydro-1H-pyrrol-3-ones which are structurally related to the known antiischemic drugs.

  DOI：

  10.1023/a:1013196008180
• 作为产物：
  描述：

  2,4'-二溴苯乙酮 、 2-氰基硫代乙酰胺 生成 4-(4-溴苯基)-2-噻唑乙腈
  参考文献：
  名称：

  新型 3-(1,3-thiazol-2-yl)-7,8-dihydroquinoline-2,5(1H,6H)-diones 的合成

  摘要：

  一种从各种 2-二甲氨基亚甲基环己烷-1,3-二酮合成新型 3-(1,3-噻唑-2-基)-7,8-二氢喹啉-2,5(1H,6H)-二酮的有效方法， (1,3-噻唑-2-基)乙腈和二甲基甲酰胺二甲基乙缩醛被开发。这些转化通过中间体 2-[2-(4-aryl-1,3-thiazol-2-yl)-2-cyanothenyl]-3-oxocyclohex-1-en-1-olates 进行。它们被分离为哌啶盐并用于与芳香胺的进一步杂环化反应，得到新的 1-aryl-3-(1,3-thiazol-2-yl)-7,8-dihydroquinoline-2,5(1H,6H) -迪奥内斯。这些化合物也是在受控微波辐射下通过制备三步“一锅”合成获得的。

  DOI：

  10.1007/s11172-008-0066-z

文献信息

• 7-Hydroxy-3-phenoxy-8-formylchromones, analogs of natural flavonoids
  作者：T. V. Shokol、O. A. Lozinskii、T. M. Tkachuk、V. P. Khilya

  DOI：10.1007/s10600-009-9345-7

  日期：2009.5

  7-Hydroxy-3-phenoxy-8-formylchromones were synthesized using the Duff reaction and were reacted with 2,4-dinitrophenylhydrazine to produce hydrazones and with an excess of hydrazine hydrate to produce the pyrazole recyclization products. Derivatives of α-pyrono[2,3-f]chromones were synthesized using the Knoevenagel condensation with 2-azahetarylacetonitriles and the Perkin reaction.

  使用Duff反应合成了7-羟基-3-苯氧基-8-甲醛色酮，并将其与2,4-二硝基苯肼反应生成脒，与过量的水合肼反应生成吡唑环化产物。通过与2-氮杂环丙叉乙腈的Knoevenagel缩合反应和Perkin反应合成了α-吡咯啉[2,3-f]色酮的衍生物。
• Synthesis of 7-Hydroxy-8-Methyl-4'-Methoxy-6-Formylisoflavone and Linear Hetarenochromones Based on It
  作者：T. V. Shokol、N. V. Gorbulenko、M. S. Frasinyuk、V. P. Khilya

  DOI：10.1007/s10600-020-03052-9

  日期：2020.5

  7-Hydroxy-8-methyl-4'-methoxy-6-formylisoflavone was synthesized from the 6-aminomethyl derivative of 7-hydroxychromone under modified Duff reaction conditions and underwent heterocyclization to form linear furo- and pyranochromones.

  7-羟基-8-甲基-4'-甲氧基-6-甲醛异黄酮是在改良的达夫反应条件下，从7-羟基色酮的6-氨甲基衍生物合成的，并经过杂环化形成线性呋喃和吡喃色酮。
• Synthesis of 5-Amino-4-(4-aryl-2-thiazolyl)-2,3-Dihydro-2-Pyrrolones
  作者：E. V. Resnyanskaya、A. V. Tverdokhlebov、A. A. Tolmachev、Yu. M. Volovenko

  DOI：10.1007/s11178-005-0153-7

  日期：2005.2

  A method was developed for preparation of 5-amino-4-(4-aryl-2-thiazolyl)-2,3-dihydro-2-pyrrolones by alkylation of 4-aryl-2-thiazolylacetonitriles by N-substituted chloroacetamides in the presence of K2CO3. In 1-(1-naphthyl)-substituted pyrrolones atropoisomerism was observed.

  在 K2CO3 的存在下，通过 N-取代的氯乙酰胺对 4-芳基-2-噻唑基乙腈进行烷基化，开发了一种制备 5-氨基-4-(4-芳基-2-噻唑基)-2,3-二氢-2-吡咯酮的方法。在 1-(1-萘基)取代的吡咯酮中观察到了异丙基异构现象。
• [EN] DERIVATIVES OF CHROMEN-2-ONE AS INHIBITORS OF VEGF PRODUCTION IN MAMMALIAN CELLS<br/>[FR] DERIVES DE CHROMEN-2-ONE UTILISES COMME INHIBITEURS DE LA PRODUCTION DES VEGF DANS LES CELLULES MAMMALIENNES
  申请人：NOVUSPHARMA SPA

  公开号：WO2003105842A1

  公开（公告）日：2003-12-24

  The compounds of formula (I) wherein A and R1-R5 are as defined in the description, are inhibitors of Vascular Endothelial Growth Factor and are useful as angiogenesis inhibitors and antiproliferative agents.

  式（I）中A和R1-R5如描述中定义的化合物，是血管内皮生长因子的抑制剂，可用作抑制血管生成和抗增殖剂。
• Synthesis and evaluation of new 2,6-diamino-5-hetarylpyrimidines as inhibitors of dihydrofolate reductase
  作者：Olga V. Khilya、Demyd S. Milokhov、Lyudmyla A. Kononets、Oleksandr L. Kobzar、Andriy I. Vovk、Yulian M. Volovenko

  DOI：10.1007/s00706-017-2032-7

  日期：2018.4

  2-hetaryl-2-(tetrahydro-2-furanyliden)acetonitriles with amidines have been developed. Some of 2,6-diamino-5-(1,3-benzothiazol-2-yl)pyrimidines were found to exhibit modest inhibitory activity against human dihydrofolate reductase. Molecular docking was performed to evaluate the binding mode of compounds of this series in the enzyme’s active site. Graphical abstract

  摘要已经开发了通过2-杂芳基-2-（四氢-2-呋喃基）乙腈与am的环转化反应制备6-氨基-5-杂芳基嘧啶衍生物的合成方法。发现一些2,6-二氨基-5-（1,3-苯并噻唑-2-基）嘧啶对人二氢叶酸还原酶显示适度的抑制活性。进行分子对接以评估该系列化合物在酶的活性位点的结合模式。 图形概要