2-甲氧基-5-甲基苯基异硫代氰酸酯 | 190774-56-2

• 物质功能分类: 化学试剂 - 有机试剂 - 硫氰酸盐/异硫氰酸酯
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-甲氧基-5-甲基苯基异硫代氰酸酯
• 中文别名: 2-甲氧基-5-甲基苯基异硫氰酸酯；异硫氰酸2-甲氧基-5-甲基苯酯
• 英文名称: 2-isothiocyanato-1-methoxy-4-methylbenzene
• 英文别名: 2-Methoxy-5-methylphenyl isothiocyanate
• CAS: 190774-56-2
• 化学式: C₉H₉NOS
• mdl: MFCD00041083
• 分子量: 179.243
• InChiKey: CYKFAZDMLSXWKZ-UHFFFAOYSA-N

物化性质

• 沸点：
  288 °C(lit.)
• 密度：
  1.146 g/mL at 25 °C(lit.)
• 闪点：
  >230 °F
• 稳定性/保质期：
  避免与氧化物、水分、酒精和胺接触。

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  53.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  6.1
• 危险品标志：
  C
• 安全说明：
  S26,S27,S36/37/39,S45
• 危险类别码：
  R34
• WGK Germany：
  3
• 海关编码：
  2930909090
• 危险品运输编号：
  2810
• 包装等级：
  II
• 危险类别：
  6.1
• 储存条件：
  保存方法：密封、阴凉、通风且干燥的地方。

SDS

Name:	2-Methoxy-5-methylphenylisothiocyanate Material Safety Data Sheet
Synonym:	None
CAS:	190774-56-2

Section 1 - Chemical Product MSDS Name:2-Methoxy-5-methylphenylisothiocyanate Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
190774-56-2	2-Methoxy-5-methylphenylisothiocyanate	97	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes and respiratory system.
Potential Health Effects
Eye:
Lachrymator (substance which increases the flow of tears).
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:
Chronic exposure may cause effects similar to those of acute exposure.

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Section 4 - FIRST AID MEASURES
Eyes: In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Get medical aid immediately.
Skin:
In case of contact, immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Get medical aid immediately. Wash clothing before reuse.
Ingestion:
If swallowed, do NOT induce vomiting. Get medical aid immediately.
If victim is fully conscious, give a cupful of water. Never give anything by mouth to an unconscious person.
Inhalation:
If inhaled, remove to fresh air. 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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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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. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Do not get in eyes, on skin, or on clothing. Do not breathe vapor.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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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 process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels.
Exposure Limits CAS# 190774-56-2: Personal Protective Equipment Eyes: Wear chemical splash goggles.
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: Liquid
Color: clear yellow
Odor: mustard-like
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 288 deg C @ 760 mm Hg
Freezing/Melting Point: Not available.
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: Insoluble.
Specific Gravity/Density: 1.14
Molecular Formula: C9H9NOS
Molecular Weight: 179.20

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong acids.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Will not occur.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 190774-56-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2-Methoxy-5-methylphenylisothiocyanate - 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 Irritating to eyes and respiratory system.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 39 Wear eye/face protection.
WGK (Water Danger/Protection)
CAS# 190774-56-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 190774-56-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 190774-56-2 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-甲氧基-5-甲基苯基异硫代氰酸酯 在 一水合肼 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 4-(2-甲氧基-5-甲基苯基)-3-氨基硫脲
  参考文献：
  名称：

  5位取代的Isatin thiosemicarbazones作为酪氨酸酶抑制剂：取代基作用的见解

  摘要：

  七个在二氢吲哚环的C-5上连接有不同取代基（R）的异丁硫半碳酰胺类似物（TSC-ISA- R（R  = -H，-CH 3，-OCH 3，-OCF 3，-F，-Cl和-NO 2），被合成并评价为蘑菇酪氨酸酶（TYR）的抑制剂。使用L -DOPA作为底物，通过研究其对TYR的双酚酶活性的抑制作用，通过光谱研究了TSC-ISA- R与取代基修饰的抑制行为和性能。TSC-ISA- R的IC 50值被确定在81–209μM范围内。动力学分析表明，TSC-ISA- R是可逆的混合型抑制剂。发现三种潜在的非共价相互作用而不是络合，包括TSC-ISA- R与游离TYR，TYR- L- DOPA复合物以及与底物L- DOPA的结合，均与抑制作用有关。取代基的修饰通过不同程度地改变所得TSC-ISA- R的特性，影响了这些相互作用。每个TSC-ISA- R的thiosemicarbazido部分都主要起抑制作

  DOI：

  10.1016/j.saa.2021.119669
• 作为产物：
  描述：

  2-isocyano-1-methoxy-4-methylbenzene 在 劳森试剂 、 三乙胺 作用下， 以 水 为溶剂， 以82 %的产率得到2-甲氧基-5-甲基苯基异硫代氰酸酯
  参考文献：
  名称：

  水性微波辅助异硫氰酸酯的新合成，通过使用 Lawesson 试剂的胺催化硫代异氰酸酯

  摘要：

  这里描述了一种用于有机合成的绿色和可持续化学方法，它涉及反应物在水存在下的微波暴露。使用 Lawesson 试剂和催化量的胺碱，特别是微波辐射条件下的三乙胺，从相应的异氰酸酯开发了一种通用、实用且高效的方案，用于制备各种功能化异硫氰酸酯。与使用有毒或挥发性亲电子液体（硫光气、其衍生物或 CS 2). 此外，为了比较，这些化合物也通过常规加热程序合成。通过比较总反应时间和产率百分比，对常规合成和微波辅助合成进行了比较。结果表明，微波辅助合成可在非常短的反应时间内实现更高的产率。 在三乙胺存在下，在常规和微波加热条件下，使用 Lawesson 试剂从异氰化物到异硫氰酸酯。

  DOI：

  10.1080/17415993.2022.2164196

文献信息

• Synthesis of Isothiocyanates and Unsymmetrical Thioureas with the Bench-Stable Solid Reagent (Me₄N)SCF₃
  作者：Thomas Scattolin、Alexander Klein、Franziska Schoenebeck

  DOI：10.1021/acs.orglett.7b00689

  日期：2017.4.7

  selective, and rapid transformation of primary amines and diamines to isothiocyanates and cyclic thioureas is disclosed. As opposed to established approaches that employ toxic or volatile electrophilic liquids and require reaction control (i.e., slow addition, cooling), this protocol utilizes the bench-stable, solid reagent (Me4N)SCF3 at room temperature. The method is characterized by operational simplicity

  公开了伯胺和二胺高效，选择性和快速转化为异硫氰酸酯和环状硫脲的方法。与采用有毒或挥发性亲电子液体并需要反应控制（即，缓慢添加，冷却）的既定方法相反，该协议在室温下利用了台式稳定的固体试剂（Me 4 N）SCF 3。该方法的特点是操作简单，速度快，效率高，官能团耐受性高和后期适用性强。副产物为固体，允许通过过滤分离目标化合物。
• Synthesis and Octopaminergic-agonist Activity of 3-(Substituted Phenyl)imidazolidine-2-thiones and Related Compounds
  作者：Akinori HIRASHIMA、Kenji SHINKAI、Eiichi KUWANO、Eiji TANIGUCHI、Morifusa ETO

  DOI：10.1271/bbb.62.1179

  日期：1998.1

  3-(Substituted phenyl)imidazolidine-2-thiones (SPITs) and related compounds were synthesized by cyclizing monoethanolamine hydrogen sulfate with arylisothiocyanates in the presence of sodium hydroxide. The activity for stimulating adenylate cyclase prepared from thoracic nerve cords of the American cockroach, Periplaneta americana L., was examined with these compounds. A SPIT with a 2,6-diethylphenyl

  通过在氢氧化钠存在下将单乙醇胺硫酸氢盐与芳基异硫氰酸酯环化，可以合成3-（取代的苯基）咪唑烷-2-硫酮（SPIT）和相关化合物。用这些化合物检查了刺激从美国蟑螂美洲大i的胸神经线制备的腺苷酸环化酶的活性。具有2,6-二乙基苯基基团的SPIT（48）是唯一的完全激动剂，其他SPIT衍生物是部分激动剂。更大的酶活化似乎是由短链烷基而不是SPITs芳香环的2,6-位上的卤素取代引起的。在2,6-二取代的SPIT中，从甲基到乙基的链长增加导致酶激活增加。同时，在2中，从乙基到异丙基的链长进一步增加 6-二取代的SPIT导致酶活化降低。能量最小的章鱼胺和48的叠加显示出结构和构象相似，这说明48的Vmax值更高。在有效SPIT的咪唑烷环的C4或C5烷基化后，酶的活化作用明显降低。因此，在SPIT的苯环和N-末端的2-位和6-位的一定程度的蓬松度和疏水性对于活化腺苷酸环化酶是有利的。
• Substituted Spiro Compounds and Their Use for Producing Pain-Relief Medicaments
  申请人：Frank Robert

  公开号：US20080269271A1

  公开（公告）日：2008-10-30

  The present invention relates to substituted spiro compounds, to processes for preparing them, to medicaments comprising these compounds and to the use of these compounds for producing medicaments.

  本发明涉及替代螺环化合物，涉及制备这些化合物的方法，涉及含有这些化合物的药物以及利用这些化合物生产药物的用途。
• Facile Access to AgOCF₃and Its New Applications as a Reservoir for OCF₂for the Direct Synthesis of N−CF₃, Aryl or Alkyl Carbamoyl Fluorides
  作者：Abdurrahman Turksoy、Thomas Scattolin、Samir Bouayad‐Gervais、Franziska Schoenebeck

  DOI：10.1002/chem.202000116

  日期：2020.2.17

  showcase its performance in trifluoromethoxylations or as reservoir for O=CF2. This enabled the direct, practical and safe synthesis of valuable N‐alkyl/aryl and N−CF3 carbamoyl fluorides from secondary amines and isothiocyanides, respectively. Our mechanistic data indicate that AgOCF3 does not liberate O=CF2 until it is activated by a nucleophilic co‐reagent, reinforcing the stability of the salt under

  创新氟化策略的发展在很大程度上还取决于现有氟化试剂的可用性，安全性和实用性。我们在本文中显示了在室温下制备有价值的AgOCF 3的直接和定量策略，并展示了其在三氟甲氧基化中或作为O = CF 2的储库的性能。这样就可以分别从仲胺和异硫氰化物直接，实用和安全地合成有价值的N-烷基/芳基和N-CF 3氨基甲酰氟。我们的机理数据表明，AgOCF 3不会释放O = CF 2 直至其被亲核助剂激活，从而在我们的新制备策略下增强了盐的稳定性。
• Straightforward access to N-trifluoromethyl amides, carbamates, thiocarbamates and ureas
  作者：Thomas Scattolin、Samir Bouayad-Gervais、Franziska Schoenebeck

  DOI：10.1038/s41586-019-1518-3

  日期：2019.9.5

  (metabolic) stability—fluorination approaches have been widely adopted5–7. Similarly, site-specific modification with isosteres and peptidomimetics8, or in particular by N-methylation9, has been used to improve the stability, physical properties, bioactivities and cellular permeabilities of compounds. However, the N-trifluoromethyl carbonyl motif—which combines both N-methylation and fluorination approaches—has

  酰胺和相关的羰基衍生物在整个物理和生命科学领域 1、2 中具有重要意义。作为关键的生物结构单元，酰胺的稳定性和构象影响肽和蛋白质的结构及其生物学功能。此外，酰胺键的形成是最常用的化学转化之一 3,4。鉴于它们无处不在，一种能够在不影响稳定性的情况下改变酰胺的​​基本性质的技术可能在制药、农业化学和材料科学中具有相当大的潜力。为了影响有机分子的物理性质——例如溶解度、亲油性、构象、pK a 和（代谢）稳定性——氟化方法已被广泛采用 5-7。相似地，使用等排体和肽模拟物 8 或特别是通过 N-甲基化 9 进行位点特异性修饰已被用于改善化合物的稳定性、物理性质、生物活性和细胞渗透性。然而，由于缺乏有效的合成方法，尚未探索结合 N-甲基化和氟化方法的 N-三氟甲基羰基基序。在这里，我们报告了一种直接获取酰胺和相关羰基化合物的 N-三氟甲基类似物的方法。该策略依赖于操作简单的台式氨基甲酰氟结构单元的制备，可以很容易地多样化为相应的