萘-2-硫代甲酰胺 | 6967-89-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 萘-2-硫代甲酰胺
• 中文别名: 2-硫代萘甲酰胺
• 英文名称: naphthalene-2-carbothioamide
• 英文别名: naphthalene-2-thiocarboxamide
• CAS: 6967-89-1
• 化学式: C₁₁H₉NS
• 分子量: 187.265
• InChiKey: ZQGJZFKITDDUEH-UHFFFAOYSA-N

物化性质

• 熔点：
  150-152°C
• 沸点：
  360.3±25.0 °C(Predicted)
• 密度：
  1.247

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险等级：
  6.1
• 危险品标志：
  Xn
• 安全说明：
  S36/37
• 危险类别码：
  R20/21/22
• 海关编码：
  2930909090
• 包装等级：
  III
• 危险类别：
  6.1
• 危险品运输编号：
  UN2811

SDS

Name:	Naphthalene-2-carbothioamide 97% Material Safety Data Sheet
Synonym:
CAS:	6967-89-1

Section 1 - Chemical Product MSDS Name:Naphthalene-2-carbothioamide 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
6967-89-1	Naphthalene-2-carbothioamide	97%	unlisted

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.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Harmful if inhaled. May cause respiratory tract irritation.
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:

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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:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 6967-89-1: 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: off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 150 - 152 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: C11H9NS
Molecular Weight: 187.27

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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:
Nitrogen oxides, carbon monoxide, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 6967-89-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Naphthalene-2-carbothioamide - 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: TOXIC SOLID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing group: III

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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# 6967-89-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 6967-89-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 6967-89-1 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：

  萘-2-硫代甲酰胺 在 Oxone 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以93%的产率得到3,5-di(naphthalen-2-yl)-1,2,4-thiadiazole
  参考文献：
  名称：

  Oxone氧化二聚硫代酰胺合成1,2,4-噻二唑

  摘要：

  1,2,4-噻二唑通过硫代酰胺的氧化二聚反应以良好的产率高效合成，使用 Oxone 作为一种容易获得、价格低廉且对环境安全的氧化剂。苯基硒酰胺的类似反应以高产率得到相应的 1,2,4-苯基硒二唑。

  DOI：

  10.1002/ejoc.201402756
• 作为产物：
  描述：

  2-萘甲醛 在 sodium hydrogen sulfide 、 甲酸 、 magnesium(II) chloride hexahydrate 、 盐酸羟胺 、 sodium formate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 萘-2-硫代甲酰胺
  参考文献：
  名称：

  β-萘并入噻唑-5-羧酰胺/噻唑-5-酮：针对两种癫痫发作模型的设计，合成和抗惊厥筛选

  摘要：

  通过使4-甲基-2-（萘-2-基）噻唑-5-羰基氯化物与四甲基-2-（萘-2-基）噻唑-5-羰基氯反应，制得一束β-萘并入噻唑-5-羧酰胺/噻唑-5-酮（7a-7o和8a-8e）。适当的胺。通过元素分析，FT-IR，1H NMR和质谱数据解释了所有化合物的结构。使用MES和化学休克（scPTZ）癫痫发作测试评估了这些化合物的抗惊厥活性。还评估了神经毒性。这些化合物中的大多数对两种动物模型均表现出显着的活性。然而，化合物7e，7j，7n和8c表现出令人鼓舞的活性，可以被认为是进一步研究的线索。

  DOI：

  10.3844/ajptsp.2019.27.37

文献信息

• Aerobic Visible‐Light Induced Intermolecular S−N Bond Construction: Synthesis of 1,2,4‐Thiadiazoles from Thioamides under Photosensitizer‐Free Conditions
  作者：Liang Zhuo、Shihua Xie、Hui Wang、Hongjun Zhu

  DOI：10.1002/ejoc.202100440

  日期：2021.6.21

  A green approach for S−N construction with concomitant synthesis of1,2,4-thiadiazoles was developed by visible-light induced oxidative cyclization of thioamides under photosensitizer-free conditions.

  在无光敏剂的条件下，通过可见光诱导硫代酰胺的氧化环化，开发了一种伴随合成 1,2,4-噻二唑的 S-N 构建的绿色方法。
• Carbene-Catalyzed Enantioselective Addition of Thioamides to Bromoenals for Access to Thiazinone Heterocycles
  作者：Changyi Liu、Shuquan Wu、Jun Xu、Lingzhu Chen、Pengcheng Zheng、Yonggui Robin Chi

  DOI：10.1021/acs.orglett.9b03685

  日期：2019.12.6

  steps include enantioselective 1,4-addition of thioamide sulfur atoms to α,β-unsaturated acyl azolium intermediate. Subsequent intramolecular annulation eventually affords thiazinone heterocycles with high optical purities. The introduction of Lewis acid additives such as Cu(OTf)2 to this NHC catalytic reaction could provide small but consistent improvements to reaction enantioselectivities.

  开发了卡宾催化的α-溴烯醛和硫代酰胺之间的反应。关键步骤包括将硫酰胺硫原子对映体选择性地1,4-加成到α，β-不饱和酰基偶氮中间体上。随后的分子内环化最终提供具有高光学纯度的噻嗪酮杂环。向该NHC催化反应中引入路易斯酸添加剂（例如Cu（OTf）2）可以为反应对映选择性提供较小但始终如一的改进。
• Synthesis and Antitumor Activity of New Thiazole Nortopsentin Analogs
  作者：Virginia Spanò、Alessandro Attanzio、Stella Cascioferro、Anna Carbone、Alessandra Montalbano、Paola Barraja、Luisa Tesoriere、Girolamo Cirrincione、Patrizia Diana、Barbara Parrino

  DOI：10.3390/md14120226

  日期：——

  New thiazole nortopsentin analogs in which one of the two indole units was replaced by a naphthyl and/or 7-azaindolyl portion, were conveniently synthesized. Among these, three derivatives showed good antiproliferative activity, in particular against MCF7 cell line, with GI50 values in the micromolar range. Their cytotoxic effect on MCF7 cells was further investigated in order to elucidate their mode

  方便地合成了新的噻唑降冰片素类似物，其中两个吲哚单元之一被萘基和/或7-氮杂吲哚基部分取代。其中，三种衍生物显示出良好的抗增殖活性，尤其是针对MCF7细胞系，其GI50值在微摩尔范围内。为了阐明它们的作用方式，进一步研究了它们对MCF7细胞的细胞毒性作用。结果表明，这三种化合物可作为促凋亡剂，诱导活细胞向早期凋亡的明显转移，而不会发挥坏死作用。它们还引起细胞周期扰动，G0 / G1和S期细胞百分比显着下降，同时G2 / M期细胞百分比增加，并出现subG1细胞群。
• A efficient protocol for the synthesis of thioamides in [DBUH][OAc] at room temperature
  作者：Xian-Ting Cao、Li Qiao、Hui Zheng、Hui-Yong Yang、Peng-Fei Zhang

  DOI：10.1039/c7ra11259a

  日期：——

  A novel, simple and eco-friendly method to synthesize thioamides from aryl nitriles and sodium sulfide (Na2S·9H2O) catalyzed by 1,8-diazabicyclo[5,4,0]undec-7-enium acetate ([DBUH][OAc]) ionic liquid (IL) at room temperature was developed in this paper. In this reaction, readily available inorganic salt (Na2S·9H2O) serves as the sulfur source, and various functional groups of aryl nitriles were well

  从芳基腈和硫化钠一种新颖的，简单的和环境友好的方法来合成硫代酰胺（钠2 S·9H 2 O）由1,8-二氮杂双环[5,4,0]十一碳-7-烯乙酸酯（[DBUH催化本文开发了室温下的[[OAc]）离子液体（IL）。在该反应中，容易获得的无机盐（Na 2 S·9H 2 O）用作硫源，并且芳基腈的各种官能团在室温下具有良好的耐受性。此外，产品易于从IL中分离出来，可以重复使用至少5次，而不会显着降低其活性，并可以用于绿色，简洁的乙硫酰胺合成中。
• Discovery of 2-Aminothiazole-4-carboxamides, a Novel Class of Muscarinic M3 Selective Antagonists, through Solution-Phase Parallel Synthesis
  作者：Yufu Sagara、Morihiro Mitsuya、Minaho Uchiyama、Yoshio Ogino、Toshifumi Kimura、Norikazu Ohtake、Toshiaki Mase

  DOI：10.1248/cpb.53.437

  日期：——

  Synthesis and structure–activity relationship of a new class of muscarinic M3 selective antagonists were described. In the course of searching for a muscarinic M3 antagonist with a structure distinct from those of the 2-(4,4-difluorocyclopentyl)-2-phenylacetamide derivatives, we identified a thiazole-4-carboxamide derivative (1) as a lead compound in our in-house chemical collection. Since this compound (1) showed relatively low binding affinity (Ki=140 nM) for M3 receptors in the human binding assays, we tried to improve its potency and selectivity for M3 over M1 and M2 receptors by derivatization of 1 through a combinatorial approach. A solution-phase parallel synthesis effectively contributed to the optimization of each segment of 1. Thus, we have identified a cyclooctenylmethyl derivative (3e) and a cyclononenylmethyl derivative (3f) as representative M3 selective antagonists in this class.

  描述了一类新的选择性抗美洲豹M3受体拮抗剂的合成和结构-活性关系。在寻找一种结构与2-(4,4-二氟环戊基)-2-苯乙酰胺衍生物不同的抗美洲豹M3受体拮抗剂的过程中，我们在内部化学库中识别出了一种噻唑-4-氨基甲酸酯衍生物（1）作为领先化合物。由于该化合物（1）在人体结合实验中对M3受体的结合亲和力较低（Ki=140 nM），我们尝试通过组合化学方法对1进行衍生化，以提高其对M3受体的效能和对M1及M2受体的选择性。溶液相平行合成有效地促进了1的每个片段的优化。因此，我们识别出环辛烯基甲基衍生物（3e）和环壬烯基甲基衍生物（3f）作为该类抗美洲豹M3受体选择性拮抗剂的代表。