3,4-二甲氧基硫代苯酚 | 19689-66-8

• 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: 3,4-二甲氧基硫代苯酚
• 英文名称: 3,5-dimethoxythiophenol
• 英文别名: 3,5-dimethoxybenzenethiol
• CAS: 19689-66-8
• 化学式: C₈H₁₀O₂S
• mdl: MFCD00085026
• 分子量: 170.232
• InChiKey: XGZPXJQXMHEIIJ-UHFFFAOYSA-N

物化性质

• 沸点：
  269.88°C (rough estimate)
• 密度：
  1.1900
• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  19.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2930909090
• 储存条件：
  存于阴凉干燥处。

SDS

Name:	3 4-Dimethoxythiophenol 99+% Material Safety Data Sheet
Synonym:	3,4-Dimethoxy-Phenylmercaptane; 4-Mercapto-Veratrol
CAS:	19689-66-8

Section 1 - Chemical Product MSDS Name:3 4-Dimethoxythiophenol 99+% Material Safety Data Sheet
Synonym:3,4-Dimethoxy-Phenylmercaptane; 4-Mercapto-Veratrol

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
19689-66-8	3,4-Dimethoxythiophenol	99+	unlisted

Hazard Symbols: T
Risk Phrases: 23/24/25

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Toxic by inhalation, in contact with skin and if swallowed.Stench.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Mercaptans may cause nausea and headache. Exposure to high concentrations of mercaptans can produce unconsciousness with cyanosis (bluish discoloration of skin due to deficient oxygenation of the blood), cold extremities and rapid pulse.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. Exposure to high concentrations of mercaptans can produce unconsciousness with cyanosis (bluish discoloration of skin due to deficient oxygenation of the blood), cold extremities and rapid pulse. Mercaptans may cause nausea and headache.
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.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or 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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Use water spray to keep fire-exposed containers cool. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Containers may explode when heated.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Cool containers with flooding quantities of water until well after fire is out. 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. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed.
Avoid ingestion and inhalation.
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 adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 19689-66-8: 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 protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: clear yellow
Odor: stench
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 162 deg C @ 25.00mmHg
Freezing/Melting Point: Not available.
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: 1.1900g/cm3
Molecular Formula: C8H10O2S
Molecular Weight: 170.23

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, excess heat.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of sulfur, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 19689-66-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3,4-Dimethoxythiophenol - 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: II
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: II
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing group: II

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: T
Risk Phrases:
R 23/24/25 Toxic by inhalation, in contact with skin
and if swallowed.
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
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# 19689-66-8: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 19689-66-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 19689-66-8 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：

  3,4-二甲氧基硫代苯酚 在 三溴化硼 、 四氯化锡 、 caesium carbonate 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 106.0h， 生成 (1R,10R,11S,16S)-5-hydroxy-3-methoxy-1,11,15,15-tetramethyl-6-(morpholin-4-ylmethyl)-8-thiatetracyclo[8.8.0.0(2,7).0(11,16)]octadeca-2,4,6-triene-8,8-dione
  参考文献：
  名称：

  SHIP1 MODULATORS AND METHODS RELATED THERETO

  摘要：

  结构化合物（I）：包括其立体异构体和药学上可接受的盐，其中X，R1，R2，R3，R4，R5，R6和R7如本文所定义。这些化合物具有作为SHIP1调节剂的活性，因此可以用于治疗任何需要SHIP1调节的各种疾病、疾病或情况。还公开了包含结构化合物（I）与药学上可接受的载体或稀释剂组合的组合物，以及通过向需要的动物施用这些化合物来进行SHIP1调节的方法。

  公开号：

  US20110136802A1
• 作为产物：
  描述：

  1-溴-3,5-二甲氧基苯 在 magnesium 、 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 以 四氢呋喃 、 1,2-二溴乙烷 为溶剂， 反应 5.0h， 以5.17 g的产率得到3,4-二甲氧基硫代苯酚
  参考文献：
  名称：

  通过适马重排从芳基亚砜和苯胺构建联芳基。

  摘要：

  已开发出用于联芳基构建的联苯胺重排的史无前例的SN变体。通过连续用三氟甲磺酸酐和三氟甲磺酸进行处理，使芳基亚砜与苯胺进行脱氢偶联，得到相应的2-氨基-2'-硫烷基-和/或4-氨基-4'-硫烷基联苯。机理研究表明，形成CC键的σ重排是由分子性的SN拴系物种分子内进行的。

  DOI：

  10.1002/chem.201903570

文献信息

• Gold‐Catalyzed Reactions of 2‐Alkynyl‐1‐indolyl‐1,2‐diols with Thiols: Stereoselective Synthesis of ( <i>Z</i> )‐α‐Indol‐3‐yl α‐(2‐Thioalkenyl) Ketones
  作者：Fernando Martínez‐Lara、Anisley Suárez、Noelia Velasco、Samuel Suárez‐Pantiga、Roberto Sanz

  DOI：10.1002/adsc.202100930

  日期：2022.1.4

  α-indol-3-yl α-((Z)-2-thioalkenyl) ketones. The sequence is triggered by the regioselective thiolation of indolyl diols followed by an attack of the sulfur instead of the indole over the activated alkyne. The final compounds are obtained in remarkably high yields and arise from simple starting materials such as indolyl acyloins, ethynyl magnesium bromide and thiols.

  炔丙二醇，2-炔基-1-(indol-3-yl)-1,2-二醇，与硫醇反应，发生复杂但选择性的金催化转化，生成 α-indol-3-yl α-(( Z )-2-硫代烯基)酮。该序列由吲哚二醇的区域选择性硫醇化引发，然后是硫而不是吲哚对活化炔的攻击。最终化合物以非常高的收率获得，并且由简单的起始材料如吲哚基丙烯酰、乙炔基溴化镁和硫醇产生。
• Steric-Free Bioorthogonal Labeling of Acetylation Substrates Based on a Fluorine–Thiol Displacement Reaction
  作者：Zhigang Lyu、Yue Zhao、Zakey Yusuf Buuh、Nicole Gorman、Aaron R. Goldman、Md Shafiqul Islam、Hsin-Yao Tang、Rongsheng E. Wang

  DOI：10.1021/jacs.0c05605

  日期：2021.1.27

  We have developed a novel bioorthogonal reaction that can selectively displace fluorine substitutions alpha to amide bonds. This fluorine-thiol displacement reaction (FTDR) allows for fluorinated cofactors or precursors to be utilized as chemical reporters, hijacking acetyltransferase-mediated acetylation both in vitro and in live cells, which cannot be achieved with azide- or alkyne-based chemical

  我们开发了一种新型生物正交反应，可以选择性地将氟取代 α 键到酰胺键。这种氟-硫醇置换反应 （FTDR） 允许将氟化辅因子或前体用作化学报告基因，在体外和活细胞中劫持乙酰转移酶介导的乙酰化，这是基于叠氮化物或炔烃的化学报告基因无法实现的。使用 FTDR 可以将氟乙酰胺标记物进一步转换为生物素或荧光团标签，从而能够对乙酰基底物进行一般检测和成像。这种策略可能会导致底物蛋白的无空间标记平台，扩展我们的化学工具箱，以系统的方式对翻译后修饰进行功能注释。
• Design, Synthesis, and X-ray Crystal Structure of Classical and Nonclassical 2-Amino-4-oxo-5-substituted-6-ethylthieno[2,3-<i>d</i>]pyrimidines as Dual Thymidylate Synthase and Dihydrofolate Reductase Inhibitors and as Potential Antitumor Agents
  作者：Aleem Gangjee、Wei Li、Roy L. Kisliuk、Vivian Cody、Jim Pace、Jennifer Piraino、Jennifer Makin

  DOI：10.1021/jm900490a

  日期：2009.8.13

  N-4-[(2-Amino-6-ethyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-5-yl)thio]benzoyl}-l-glutamic acid 2 and 13 nonclassical analogues 2a−2m were synthesized as potential dual thymidylate synthase (TS) and dihydrofolate reductase (DHFR) inhibitors and as antitumor agents. The key intermediate in the synthesis was 2-amino-6-ethyl-5-iodothieno[2,3-d]pyrimidin-4(3H)-one, 7, to which various arylthiols were

  N -4-[(2-Amino-6-ethyl-4-oxo-3,4-dihydrothieno[2,3 - d ]pyrimidin-5-yl)thio]benzoyl} -l-谷氨酸2和 13 非经典类似物2a - 2m被合成为潜在的双胸苷酸合酶 (TS) 和二氢叶酸还原酶 (DHFR) 抑制剂和抗肿瘤剂。合成中的关键中间体是 2-amino-6-ethyl-5-iodothieno[2,3- d ]pyrimidin-4(3 H )-one, 7，在其 5 位连接了各种芳基硫醇。耦合8与升谷氨酸二乙酯和皂化，得到2。X射线晶体结构2和1（的6-甲基类似物2），DHFR，及NADPH显示出对第一次，噻吩并[2,3- d处于“叶酸”模式]嘧啶环结合。化合物2是一种出色的人 TS (IC 50 = 54 nM) 和人 DHFR (IC 50 = 19 nM)双重抑制剂，并提供了针对培养中肿瘤细胞的纳摩尔
• New Inhibitors of Indoleamine 2,3-Dioxygenase 1: Molecular Modeling Studies, Synthesis, and Biological Evaluation
  作者：Antonio Coluccia、Sara Passacantilli、Valeria Famiglini、Manuela Sabatino、Alexandros Patsilinakos、Rino Ragno、Carmela Mazzoccoli、Lorenza Sisinni、Alato Okuno、Osamu Takikawa、Romano Silvestri、Giuseppe La Regina

  DOI：10.1021/acs.jmedchem.6b00718

  日期：2016.11.10

  Indoleamine 2,3-dioxygenase 1 (IDO1) is an attractive target for anticancer therapy. Herein, we report a virtual screening study which led to the identification of compound 5 as a new IDO1 inhibitor. In order to improve the biological activity of the identified hit, arylthioindoles 6–30 were synthesized and tested. Among these, derivative 21 exhibited an IC50 value of 7 μM, being the most active compound

  吲哚胺 2,3-双加氧酶 1 (IDO1) 是抗癌治疗的一个有吸引力的目标。在此，我们报告了一项虚拟筛选研究，该研究导致将化合物5鉴定为新的 IDO1 抑制剂。为了提高所识别命中的生物活性，arylthioindoles 6 - 30合成并测试。其中，衍生物21的IC 50值为7 μM，是该系列中活性最强的化合物。此外，化合物5和21诱导表达 IDO1 的癌细胞系 HTC116 和 HT29 的剂量依赖性生长抑制。为了使获得的结果合理化并提出新的化学修饰，进行了三维定量构效关系研究。
• SUBSTITUTED 3-HETEROARYLOXY-1H-PYRAZOLES AND SALTS THEREOF AND THEIR USE AS HERBICIDAL ACTIVE SUBSTANCES
  申请人：BAYER CROPSCIENCE AKTIENGESELLSCHAFT

  公开号：US20200181117A1

  公开（公告）日：2020-06-11

  A substituted 3-heteroaryloxy-1H-pyrazole of the general formula (I) or salt thereof Substituted 3-heteroaryloxy-1H-pyrazoles of the general formula (I) are described, as is their use as herbicides, in particular for controlling broad-leaved weeds and/or weed grasses in crops of useful plants and/or as plant growth regulators for influencing the growth of crops of useful plants described. The present invention also relates to herbicidal and/or plant growth-regulating compositions comprising one or more compounds of the general formula (I).

  通用式（I）的取代3-杂环氧基-1H-吡唑或其盐已被描述。 通用式（I）的取代3-杂环氧基-1H-吡唑被描述， 以及它们作为除草剂的用途，特别是用于控制作物中的阔叶杂草和/或杂草草，以及作为植物生长调节剂，影响作物生长的用途。 本发明还涉及包含一个或多个通用式（I）化合物的除草剂和/或植物生长调节剂组合物。