3,4-二甲基苯基异硫氰酸酯 | 19241-17-9

• 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: 3,4-二甲基苯基异硫氰酸酯
• 中文别名: 3,4-二甲基异硫氰酸苯酯
• 英文名称: 3,4-xylyl isothiocyanate
• 英文别名: 3,4-dimethylphenyl isothiocyanate；4-isothiocyanato-1,2-dimethylbenzene；3,4-Xylylisothiocyanat
• CAS: 19241-17-9
• 化学式: C₉H₉NS
• mdl: MFCD00031536
• 分子量: 163.243
• InChiKey: JFSHJWKBNJMGOK-UHFFFAOYSA-N

物化性质

• 沸点：
  132°C/8mm
• 密度：
  1.08

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  44.4
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT, CORROSIVE
• 危险品标志：
  Xi,C
• 危险类别码：
  R20/21/22
• 危险品运输编号：
  2810
• 海关编码：
  2930909090
• 安全说明：
  S26,S36/37/39

SDS

Name:	3 4-Dimethylphenyl isothiocyanate 97% Material Safety Data Sheet
Synonym:
CAS:	19241-17-9

Section 1 - Chemical Product MSDS Name:3 4-Dimethylphenyl isothiocyanate 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
19241-17-9	3,4-Dimethylphenyl isothiocyanate	97%	unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Irritating to eyes, respiratory system and skin.Moisture sensitive.
Potential Health Effects
Eye:
Causes eye irritation. Lachrymator (substance which increases the flow of tears).
Skin:
Causes skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Harmful if inhaled. Causes 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 foam, dry chemical, or carbon dioxide.

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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.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Use only in a chemical fume hood.
Storage:
Store in a cool, dry place. Store in a tightly closed container.
Store under nitrogen.

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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# 19241-17-9: 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: Liquid
Color: pale yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 74 - 76 deg C
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:
Molecular Formula: C9H9NS
Molecular Weight: 163

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials, exposure to moist air or water.
Incompatibilities with Other Materials:
Acids, bases, oxidizing agents, reducing agents, amines.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 19241-17-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3,4-Dimethylphenyl isothiocyanate - 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 LIQUID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2810
Packing Group: III
IMO
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
Packing Group: III
RID/ADR
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
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.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 19241-17-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 19241-17-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 19241-17-9 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：

  3,4-二甲基苯基异硫氰酸酯 在 肼基甲酸叔丁酯 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 (Z)-N-(3,4-dimethylphenyl)-2-(2-oxoindolin-3-ylidene)hydrazinecarbothioamide
  参考文献：
  名称：

  Synthesis and Structure–Activity Evaluation of Isatin-β-thiosemicarbazones with Improved Selective Activity toward Multidrug-Resistant Cells Expressing P-Glycoprotein

  摘要：

  Cancer multidrug resistance (MDR) mediated by ATP-binding cassette (ABC) transporters presents a significant unresolved clinical challenge. One strategy to resolve MDR is to develop compounds that selectively kill cells overexpressing the efflux transporter P-glycoprotein (MDR1, P-gp, ABCB1). We have previously reported structure-activity studies based around the lead compound NSC73306 (1, 1-isatin-4-(4'-methoxyphenyl)-3-thiosemicarbazone, 4.3-fold selective). Here we sought to extend this work on MDR1-selective analogues by establishing whether 1 showed "robust" activity against a range of cell lines expressing P-gp. We further aimed to synthesize and test analogues with varied substitution at the N4-position, and substitution around the N4-phenyl ring of isatin-beta-thiosemicarbazones (IBTs), to identify compounds with increased MDR1-selectivity. Compound 1 demonstrated MDR1-selectivity against all P-gp-expressing cell lines examined. This selectivity was reversed by inhibitors of P-gp ATPase activity. Structural variation at the 4'-phenyl position of 1 yielded compounds of greater MDR1-selectivity. Two of these analogues, 1-isatin-4-(4'-nitrophenyl)-3-thiosemicarbazone (22, 8.3-fold selective) and 1-isatin-4-(4'-tert-butyl phenyl)-3-thiosemicarbazone (32, 14.8-fold selective), were selected for further testing and were found to retain the activity profile of 1. These compounds are the most active IBTs identified to date.

  DOI：

  10.1021/jm2006047
• 作为产物：
  描述：

  triethylamine (3,4-dimethylphenyl)carbamodithioate 在 丙烯酸甲酯（MA） 作用下， 以 水 为溶剂， 反应 1.5h， 以84%的产率得到3,4-二甲基苯基异硫氰酸酯
  参考文献：
  名称：

  The thiocarbonyl ‘S’ is softer than thiolate ‘S’: A catalyst-free one-pot synthesis of isothiocyanates in water

  摘要：

  在水中介质中，用甲基丙烯酸处理预制的或原位生成的芳基/烷基二硫代氨基甲酸盐三乙基铵盐（ArNHCSS−.Et3NH+）仅得到芳基异硫氰酸酯（ArNCS），而原位生成的芳基二硫代氨基甲酸（ArNHCSS−.H+）仅生成硫代迈克尔加合物（ArNHCSSCH2CH2COOMe）。这种差异性反应活性可以通过两种替代机制来解释，这取决于反荷离子的性质和反应介质的pH值。不管反荷离子如何，与二硫代氨基甲酸盐中的硫醇/硫醇盐硫（−SH/S−）相比，硫羰基硫（=S）原子具有较大的轨道系数，更为柔软，前者通过1,4-加成与迈克尔受体加合。

  DOI：

  10.1039/b923336a

文献信息

• Substituted benzazoles and methods of their use as inhibitors of Raf kinase
  申请人：——

  公开号：US20040122237A1

  公开（公告）日：2004-06-24

  New substituted benz-azole compounds, compositions and methods of inhibition of Raf kinase activity in a human or animal subject are provided. The new compounds compositions may be used either alone or in combination with at least one additional agent for the treatment of a Raf kinase mediated disorder, such as cancer.

  提供了新的替代苯唑化合物、组合物和抑制人类或动物主体中Raf激酶活性的方法。这些新化合物组合物可以单独使用，也可以与至少一种额外药物结合，用于治疗由Raf激酶介导的疾病，如癌症。
• Synthesis and bioevaluation of N,4-diaryl-1,3-thiazole-2-amines as tubulin inhibitors with potent antiproliferative activity
  作者：Maolin Sun、Qile Xu、Jingwen Xu、Yue Wu、Yueting Wang、Daiying Zuo、Qi Guan、Kai Bao、Jian Wang、Yingliang Wu、Weige Zhang

  DOI：10.1371/journal.pone.0174006

  日期：——

  inhibitors and evaluated for their antiproliferative activity in three human cancer cell lines. Most of the target compounds displayed moderate antiproliferative activity, and N-(2,4-dimethoxyphenyl)-4-(4-methoxyphenyl)-1,3-thiazol-2-amine (10s) was determined to be the most potent compound. Tubulin polymerization and immunostaining experiments revealed that 10s potently inhibited tubulin polymerization

  设计并合成了一系列含有三个带有氨基接头的芳香环的N，4-二芳基-1,3-噻唑-2-胺，作为微管蛋白抑制剂，并评估了它们在三种人类癌细胞系中的抗增殖活性。大多数目标化合物均显示出适度的抗增殖活性，N-（2,4-二甲氧基苯基）-4-（4-甲氧基苯基）-1,3-噻唑-2-胺（10s）被确定为最有效的化合物。微管蛋白聚合和免疫染色实验表明，10s以类似于CA-4的方式有效抑制微管蛋白聚合并破坏微管蛋白微管动力学。此外，10s以浓度和时间依赖性方式有效地诱导了SGC-7901细胞周期阻滞在G2 / M期。分子对接结果表明10s可以结合微管蛋白的秋水仙碱结合位点。
• Desulfurization Strategy in the Construction of Azoles Possessing Additional Nitrogen, Oxygen or Sulfur using a Copper(I) Catalyst
  作者：Srimanta Guin、Saroj Kumar Rout、Anupal Gogoi、Shyamapada Nandi、Krishna Kanta Ghara、Bhisma K. Patel

  DOI：10.1002/adsc.201200408

  日期：2012.10.8

  A tandem and convergent approach to various N-, O-, or S-containing azoles has been developed by exploiting the thiophilic property of copper(I) iodide used in a catalytic quantity. The present protocol gives access to amino-substituted tetrazoles, triazoles, oxadiazoles and thiadiazoles via oxidative desulfurization of their respective precursors followed by inter- or intramolecular attack of suitable

  通过利用催化量使用的碘化亚铜（I）的亲硫特性，已经开发出一种串联和收敛的方法，用于处理各种含N，O或S的唑。本方案通过其各自前体的氧化脱硫，然后通过分子间或分子内攻击合适的亲核试剂，来获得氨基取代的四唑，三唑，恶二唑和噻二唑。对于氨基四唑和三唑，可通过适当调节pK a获得出色的区域选择性与不对称硫脲连接的母体胺的分子量 该方法代表了一种自动催化过程，其中碘化铜（I）被转化为硫化铜（II），硫化铜又转化为活性的氧化铜（II），有效地推进了催化循环。还使用扫描电子显微镜（SEM）和能量色散X射线光谱（EDS）分析研究了铜催化剂的命运，从而深入了解了该催化过程的机理。
• 2-Imino-imidazolidine derivatives
  申请人：Hoffman-La Roche Inc.

  公开号：US04244957A1

  公开（公告）日：1981-01-13

  2-Imino-imidazolidine derivatives of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as hereinafter set forth, and pharmaceutically acceptable acid addition salts thereof, are described. The 2-imino-imidazolidine derivatives are useful in the treatment of hypertension.

  描述了公式##STR1##中R.sup.1、R.sup.2、R.sup.3和R.sup.4如下所述的2-亚胺-咪唑烷衍生物，以及其药学上可接受的酸盐。这些2-亚胺-咪唑烷衍生物在治疗高血压方面是有用的。
• Anti-inflammatory Activity of Substituted 1,3,4-Oxadiazoles
  作者：Krishna Raman、Surendra S. Parmar、Steven K. Salzman

  DOI：10.1002/jps.2600781206

  日期：1989.12

  possessed antiproteolytic activity and the in vitro inhibition of trypsin-induced hydrolysis of bovine serum albumin ranged from 13 to 75% for substituted thiosemicarbazides and 39 to 70% for substituted oxadiazoles. There was no relationship between the anti-inflammatory activity of substituted thiosemicarbazides and substituted oxadiazoles and their antiproteolytic effectiveness. The low toxicity of

  通过将相应的1-（4-联苯氧基乙酰基）-4-取代的硫代氨基脲环合，合成了各种2-（4-联苯氧基甲基）-5-芳基氨基-1,3,4-恶二唑。这些化合物的元素分析和红外，质谱和核磁共振光谱数据均具有特征。所有取代的硫代氨基脲（100 mg / kg，ip）和环化的取代的恶二唑（100 mg / kg，ip）都具有抗炎活性，这是由于它们具有抵抗角叉菜胶引起的大鼠足水肿的能力，其范围为28分别达到68％和36％至76％。通常，取代的硫代氨基脲的环化会导致其相应的取代的恶二唑的抗炎活性增加，但含有2,4-二甲基和3的那些除外。在其分子结构中存在4-二甲基取代基。氢化可的松（10 mg / kg，ip）和羟苯丁酮（40 mg / kg，ip）被用作标准参比药物，它们分别提供45％和53％的保护。所有化合物（1 mM）均具有抗蛋白水解活性，胰蛋白酶诱导的牛血清白蛋白的体外抑制作用在取代的硫代氨基脲中占13

表征谱图