9-异硫氰酸酯吖啶 | 7620-46-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 9-异硫氰酸酯吖啶
• 英文名称: 9-isothiocyanatoacridine
• 英文别名: 9-Isothiocyanatoacridin；acridin-9-yl isothiocyanate；9-acridineisothiocyanate
• CAS: 7620-46-4
• 化学式: C₁₄H₈N₂S
• 分子量: 236.297
• InChiKey: NLSUMBWPPJUVST-UHFFFAOYSA-N

物化性质

• 熔点：
  131-132 °C
• 沸点：
  449.7±18.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.3
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S22,S45
• 危险类别码：
  R42

SDS

Name:	9-Isothiocyanatoacridine 99% (Titr.) Material Safety Data Sheet
Synonym:
CAS:	7620-46-4

Section 1 - Chemical Product MSDS Name:9-Isothiocyanatoacridine 99% (Titr.) Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
7620-46-4	9-isothiocyanatoacridine	99	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.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation. The toxicological properties of this material have not been fully investigated.
Skin:
May cause skin irritation. The toxicological properties of this material have not been fully investigated.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
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 immediately.
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:
If victim is conscious and alert, give 2-4 cupfuls of milk or water.
Never give anything by mouth to an unconscious person. Get medical aid immediately.
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.
Extinguishing Media:
Use agent most appropriate to extinguish fire. 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:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. 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. 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:
Use adequate ventilation to keep airborne concentrations low. Use process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels.
Exposure Limits CAS# 7620-46-4: 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:
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: Not available.
Color: yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 128 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: C14H8N2S
Molecular Weight: 236.30

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Irritating and toxic fumes and gases.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 7620-46-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
9-isothiocyanatoacridine - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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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 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# 7620-46-4: No information available.
Canada
CAS# 7620-46-4 is listed on Canada's NDSL List.
CAS# 7620-46-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 7620-46-4 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  9-异硫氰酸酯吖啶 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以70%的产率得到4-(9,10-dihydroacridin-9-ylidene)thiosemicarbazide
  参考文献：
  名称：

  丙烯腈硫代氨基脲的互变异构，区域异构和环化反应†

  摘要：

  考察了甲基和苯肼与丙烯醛-9-基异硫氰酸酯的区域选择性（因此得到在尿素型侧被a啶取代的硫代氨基脲）。甲肼的区域选择性很高，其中α-氮原子比β-氮原子具有更多的亲核性。苯肼的区域选择性很差，但随溶剂的变化而变化，只有在乙醇的情况下，α-氮原子的亲核优势才明显。值得注意的是，虽然两种苯基硫代氨基脲都以螺环形式存在于溶液中，但是甲基产物以开链和螺硫代氨基脲的平衡混合物的形式存在。对NH 2的反应还研究了甲基丙烯酸酯-9-基硫代氨基脲（1-异亚丙基-2-甲基硫代氨基脲）的封闭类似物。有趣的是，存在于起始原料本身中的是新颖的结构基序，其中三唑硫酮代表环状和开链形式之间平衡的主要种类。

  DOI：

  10.1002/jhet.5570430317
• 作为产物：
  描述：

  吖啶酮 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.5h， 生成 9-异硫氰酸酯吖啶
  参考文献：
  名称：

  Singer, Berndt; Maas, Gerhard, Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1984, vol. 39, # 10, p. 1399 - 1408

  摘要：

  DOI：

文献信息

• [EN] TARGETED DRUG DELIVERY THROUGH AFFINITY BASED LINKERS<br/>[FR] ADMINISTRATION CIBLÉE D'UN MÉDICAMENT FAISANT APPEL À DES COUPLEURS FONDÉS SUR L'AFFINITÉ
  申请人：INVICTUS ONCOLOGY PVT LTD

  公开号：WO2015148126A1

  公开（公告）日：2015-10-01

  The current invention discloses targeted drug delivery conjugates comprising a targeting moiety linked to a drug via a molecule having an affinity for the targeting moiety. Typically, the conjugate comprises a targeting ligand and a molecule of interest, e.g., a therapeutic agent. The targeting ligand and the molecule of interest are linked to each other via an affinity ligand. The affinity ligand is further covalently or non-covalently linked to a drug or therapeutic agent. The drug can be modified to make it more soluble and so that it cleaves from the linking molecule at the target site.

  当前的发明揭示了包括通过具有与靶向基团亲和力的分子连接到药物的靶向药物传递共轭物。通常，该共轭物包括一个靶向配体和一个感兴趣的分子，例如，一个治疗剂。靶向配体和感兴趣的分子通过一个亲和配体相互连接。该亲和配体进一步以共价或非共价方式连接到药物或治疗剂。药物可以被修改以使其更溶解，并使其在靶点处从连接分子中解离。
• Reaction of Thiocarbonyl Fluoride Generated from Difluorocarbene with Amines
  作者：Jiao Yu、Jin-Hong Lin、Ji-Chang Xiao

  DOI：10.1002/anie.201710186

  日期：2017.12.22

  The reaction of thiocarbonyl fluoride, generated from difluorocarbene, with various amines under mild conditions is described. Secondary amines, primary amines, and o‐phenylenediamines are converted to thiocarbamoyl fluorides, isothiocyanates, and difluoromethylthiolated heterocycles, respectively. Thiocarbamoyl fluorides were further transformed into trifluoromethylated amines by using a one‐pot process

  描述了在温和条件下由二氟卡宾生成的硫代羰基氟化物与各种胺的反应。仲胺，伯胺和邻苯二胺分别转化为硫代氨基甲酰氟，异硫氰酸酯和二氟甲基硫代杂环。硫氨甲酰氟通过一锅法进一步转化为三氟甲基化胺。硫代羰基氟化物在原位生成，并在温和条件下在一锅中迅速完全转化；因此，不需要特殊的安全预防措施。
• Methylation of Acridin-9-ylthioureas. Structure, Fluorescence and Biological Properties of Products
  作者：Juraj Bernát、Eva Balentová、Pavol Kristian、Ján Imrich、Erik Sedlák、Ivan Danihel、Stanislav Böhm、Naďa Prónayová、Kalevi Pihlaja、Karel D. Klika

  DOI：10.1135/cccc20040833

  日期：——

  The structure, fluorescence, biological properties and S(N)-methylation reactions of ten 1,1-alkyl/aryl-disubstituted 3-(acridin-9-yl)thioureas 4 have been studied. Various reaction conditions allowed to obtain corresponding S-methyl 5 and S,N-dimethyl derivatives 6 in good yields. Structure and stereochemistry of the synthesized products are demonstrated by ab initio quantum chemical calculations and NMR techniques including PDQF-COSY, selective INEPT and NOE-difference experiments. Remarkable upfield ¹³C shifts of resonance signals of carbons C-4a, C-10a adjacent to acridine N-10 are characteristic of hydroiodides in contrast to free bases. Z configuration in isothioureas 7 with secondary amino rest in relation to E configuration of isothioureas with primary amino rest is discussed. Of the obtained products, some isothiourea salts 6 exhibit more than 2 orders of magnitude higher intensity of fluorescence, using 9-isothiocyanatoacridine as a standard. The obtained isothiourea hydroiodides 5 and dimethylisothiourea iodides 6 show remarkable biological activity against Mycobacterium tuberculosis.

  对十个1,1-烷基/芳基-二取代-3-(吖啶-9-基)硫脲的结构、荧光、生物活性和S(N)-甲基化反应进行了研究。各种反应条件使得可以很好地获得相应的S-甲基衍生物5和S,N-二甲基衍生物6。合成产物的结构和立体化学通过ab initio量子化学计算和NMR技术进行展示，包括PDQF-COSY、选择性INEPT和NOE差异实验。与自由碱相比，吖啶N-10相邻的碳C-4a、C-10a的共振信号显著上移是碘化物的特征。讨论了次级氨基取代的异硫脲7与初级氨基取代的异硫脲的Z构型与E构型的关系。在获得的产物中，一些异硫脲盐6的荧光强度比使用9-异硫氰酸吖啶作为标准时高2个数量级。获得的异硫脲碘化物5和二甲基异硫脲碘化物6对Mycobacterium tuberculosis显示出显著的生物活性。

• Regiospecific synthesis, structure and electron ionization mass spectra of 1,3-thiazolidin-4-ones containing the acridine skeleton
  作者：Imrich Géci、Ján Imrich、Pavol Kristian、Henri Kivelä、Pauliina Valtamo、Kalevi Pihlaja

  DOI：10.1002/jhet.5570420524

  日期：2005.7

  no-1,3-thiazolidin-4-ones (8b-i) and 2-alkyl(aryl)imino-3-(acridin-9′-yl)-1,3-thiazolidin-4-ones (11a-i) was performed by the reaction of 3-(acridin-9-yl)-1-alkyl(aryl)thioureas 5a-i with methyl bromoacetate and bromoacetyl bromide, respectively, via the corresponding isothiourea hydrobromides with excellent regioselectivity. The structure, NMR spectra and mass spectrometric behavior of the resulting

  区域异构的3-烷基（芳基）-2-（ac啶-9'-基）亚氨基-1,3-噻唑烷丁-4-酮（8b-i）和2-烷基（芳基）亚氨基-3-（ac啶）的合成通过使3-（ac啶酮-9-基）-1-烷基（芳基）硫脲5a-i与溴乙酸甲酯反应来进行-9'-基）-1,3-噻唑烷-4-酮（11a-i）分别通过相应的异硫脲氢溴酸盐和溴乙酰溴，具有良好的区域选择性。讨论了所得化合物的结构，NMR光谱和质谱行为。
• Spontaneous cyclization of (acridin-9-ylmethyl)thioureas to spiro [dihydroacridine-9′(10′H),5-imidazolidine]-2-thiones, a novel type of acridine spirocycles
  作者：Mária Vilková、Marianna Prokaiová、Ján Imrich

  DOI：10.1016/j.tet.2013.12.001

  日期：2014.1

  Novel acridine spirocompounds, spiro[dihydroacridine-9′(10′H),5-imidazolidine]-2-thiones have been prepared by the spontaneous cyclization of 1-substituted 3-(acridin-9-ylmethyl)thioureas, which were obtained from 1-(acridin-9-yl)methanamine, N-(acridin-9-ylmethyl)propan-1-amine, and N-(acridin-9-ylmethyl)benzylamine and alkyl/aryl isothiocyanates, as continuation of our previous studies on new acridine

  新颖吖spirocompounds，螺[二氢吖-9'（10' ħ），5-咪唑烷] -2-硫酮制备了由取代的1 3-（吖啶-9-基甲基）硫脲，从其中获得的自发环化1-（acridin-9-基）甲胺，N-（acridin-9-基甲基）丙-1-胺和N-（acridin-9-ylmethyl）苄胺和烷基/芳基异硫氰酸酯，作为我们先前对新a啶螺环的研究的延续。随后将由此获得的咪唑烷-2-硫酮用异腈腈转化成咪唑烷-2-一类似物，其中一些类似物部分地重新打开为相应的（ac啶9-9-基甲基）脲。对于具有两个a啶环的3-（acridin-9-基甲基）-1-（acridin-9-基）硫脲，发现了通过CH碳负离子而不是N-1氮的不寻常的螺环化。螺环1、3和4位置的结构修饰以及1 H，13 C和15N NMR光谱和X射线晶体学已被用来合理化各种9-取代的cr啶的易于发生螺环化的普遍倾向。