1,1’,3,3,3’,3’-六甲基吲哚双碳菁碘 | 36536-22-8

• 物质功能分类: 生物化工 - 生化试剂 - 荧光成像
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 1,1’,3,3,3’,3’-六甲基吲哚双碳菁碘
• 中文别名: 1,1',3,3,3',3'-六甲基吲哚双碳菁碘；1,3,3,1',3',3'-六甲基吲哚双碳菁碘化物
• 英文名称: 1,1',3,3,3',3'-hexamethylindodicarbocyanine iodide
• 英文别名: HIDCI；(2E)-1,3,3-trimethyl-2-[(2E)-5-(1,3,3-trimethylindol-1-ium-2-yl)penta-2,4-dienylidene]indole;iodide
• CAS: 36536-22-8
• 化学式: C₂₇H₃₁N₂*I
• 分子量: 510.461
• InChiKey: UANMYOBKUNUUTR-UHFFFAOYSA-M

物化性质

• 熔点：
  264 °C (dec.)(lit.)
• 密度：
  1.2991 (estimate)
• 溶解度：
  Soluble in methanol, dimethyl sulfoxide; partially soluble in water
• 最大波长(λmax)：
  638 nm
• 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)：
  3.12
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  6.2
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn,Xi
• 安全说明：
  S24/25,S26,S36
• 危险类别码：
  R36/37/38,R20/21/22

SDS

Name:	1 1 3 3 3 3 -Hexamethylindodicarbocyanine iodide laser grade 99% Material Safety Data Sheet
Synonym:	HIDC iodide
CAS:	36536-22-8

Section 1 - Chemical Product MSDS Name:1 1 3 3 3 3 -Hexamethylindodicarbocyanine iodide laser grade 99% Material Safety Data Sheet
Synonym:HIDC iodide

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
36536-22-8	3h-indolium,2-5-(1,3-dihydro-1,3,3-tri		253-091-6

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea.
Inhalation:
Causes respiratory tract irritation. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately 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. Do NOT use mouth-to-mouth resuscitation.
Notes to Physician:
Treat symptomatically and supportively.

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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:
Vacuum or sweep up material and place into a suitable disposal container. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation. Use with adequate ventilation.
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# 36536-22-8: 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: Crystals
Color: blue-green
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 264 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water: Not available.
Specific Gravity/Density: Not available.
Molecular Formula: C27H31IN2
Molecular Weight: 510.45

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, hydrogen iodide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 36536-22-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
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: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 36536-22-8: No information available.
Canada
CAS# 36536-22-8 is listed on Canada's NDSL List.
CAS# 36536-22-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 36536-22-8 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途：适宜用作激光染料。

反应信息

• 作为反应物：
  描述：

  1,1’,3,3,3’,3’-六甲基吲哚双碳菁碘 以44%的产率得到
  参考文献：
  名称：

  BRIKS, YU. L.;ROMANOV, N. N.;TUROV, A. V., ZH. ORGAN. XIMII, 26,(1990) N2, S. 2591-2600

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,3-三甲基-3H-吲哚 在 sodium acetate 、 乙酸酐 作用下， 以 neat (no solvent) 为溶剂， 反应 0.66h， 生成 1,1’,3,3,3’,3’-六甲基吲哚双碳菁碘
  参考文献：
  名称：

  微波辅助和环境友好的方法合成近红外荧光五甲胺花青染料

  摘要：

  开发了一种省时，环保的微波方法，并将其用于合成五甲胺花青染料及其相应前体的系统库。本文概述的合成从几天到几分钟极大地减少了五甲胺碳菁染料合成的反应途径，并且与常规加热方法（18-64％）相比，产率提高（89-98％）。通过微波辅助有机合成方法合成了十二个五次甲基花青染料实例，该化合物在快速的反应时间内提供了优异的收率，并使用简便的分离方法获得了该实例。此外，制备了三种具有新的亚甲基二氧基杂环结构的花青，与未取代的对应物相比，它们具有约40 nm的红移。

  DOI：

  10.1016/j.dyepig.2014.07.035

文献信息

• NEAR-IR GLUCOSE SENSORS
  申请人：Profusa, Inc.

  公开号：US20180179233A1

  公开（公告）日：2018-06-28

  Glucose-sensing luminescent dyes, polymers, and sensors are provided. Additionally, systems including the sensors and methods of using these sensors and systems are provided.

  提供了葡萄糖感应荧光染料、聚合物和传感器。此外，还提供了包括传感器的系统以及使用这些传感器和系统的方法。
• Supramolecular control of photophysical properties of cyanine dyes
  作者：Tata Venkata S. Rao、Jeffrey B. Huff、Christopher Bieniarz

  DOI：10.1016/s0040-4020(98)00597-3

  日期：1998.9

  intramolecular complexation of cyanine dyes and cyclodextrins with the objective of modifying the photophysical behaviour of the dyes. We demonstrate that dye inclusion complex formation with cyclodextrins serves to inhibit dimer formation as well as enhance photostability of cyanines. We also show that the modification of the physicochemical properties of cyanine dyes by cyclodextrin complexation is a

  我们提出了花青染料和环糊精分子内络合研究的结果，目的是改变染料的光物理行为。我们证明与环糊精的染料包合物形成可以抑制二聚体的形成以及增强花菁的光稳定性。我们还表明，通过环糊精络合对花青染料的理化性质的修饰是高度选择性的，结构依赖性的现象。
• [EN] NEAR-INFRARED FLUORESCENT CONTRAST BIOIMAGING AGENTS AND METHODS OF USE THEREOF<br/>[FR] AGENTS DE CONTRASTE POUR LA BIOIMAGERIE DANS LE PROCHE INFRAROUGE ET LEURS MÉTHODES D'UTILISATION
  申请人：BETH ISRAEL HOSPITAL

  公开号：WO2015066290A1

  公开（公告）日：2015-05-07

  The instant invention provides near-infrared fluorescent biological contrast agents and methods of using them.

  这项发明提供了近红外荧光生物对比剂及其使用方法。
• Hydrocyanines: A Class of Fluorescent Sensors That Can Image Reactive Oxygen Species in Cell Culture, Tissue, and In Vivo
  作者：Kousik Kundu、Sarah F. Knight、Nick Willett、Sungmun Lee、W. Robert Taylor、Niren Murthy

  DOI：10.1002/anie.200804851

  日期：2009.1.2

  Accurate and tunable: The title compounds can detect reactive oxygen species (ROS) in cell culture, tissue explants, and for the first time in vivo. The hydrocyanines are synthesized by reduction of the cyanine dyes with NaBH4. They can accurately detect nanomolar levels of ROS, have excellent stability against autoxidation, and have tunable emission wavelengths in the range 560–830 nm.

  准确且可调：标题化合物可以检测细胞培养物、组织外植体中的活性氧 (ROS)，这是首次在体内检测。氢花青是通过用 NaBH 4还原花青染料来合成的。它们可以准确检测纳摩尔水平的 ROS，对自氧化具有出色的稳定性，并且具有 560-830 nm 范围内的可调发射波长。
• 着色組成物、着色硬化膜及び表示素子
  申请人：ＪＳＲ株式会社

  公开号：JP2015129263A

  公开（公告）日：2015-07-16

  【課題】着色剤としてシアニン染料を含む、保存安定性の良好な着色組成物を提供すること。【解決手段】（Ａ）着色剤、（Ｂ）バインダー樹脂及び（Ｃ）重合性化合物を含む着色組成物であって、（Ａ）着色剤が、下記式（１）で表される構造を有する化合物及び下記式（２）で表される構造を有する化合物を含み、下記式（２）で表される構造を有する化合物の含有量が、下記式（１）で表される構造を有する化合物及び下記式（２）で表される構造を有する化合物の合計含有量に対して０．００１質量％以上である、着色組成物。 〔式（１）、（２）において、 環Ｚ1、環Ｚ2、環Ｚ3及び環Ｚ4は、相互に独立に、置換若しくは非置換の複素環を示し、Ｒ1〜Ｒ6は、相互に独立に、水素原子、ハロゲン原子、又は置換若しくは非置換の炭化水素基を示す。但し、Ｒ1、Ｒ2、Ｒ4及びＲ5が複数存在する場合、同一でも異なっていても良い。ｐは、１又は２を示し、ｑは、ｐが１であるときには２以上の整数を示し、ｐが２であるときには３以上の整数を示す。〕【選択図】なし

  任务：提供一种含有靛染料作为染料的保存稳定性良好的染色组合物。 解决方案：一种染色组合物，包括（A）染料，（B）粘合剂树脂和（C）聚合性化合物，其中（A）染料包括具有下式（1）所示结构的化合物和具有下式（2）所示结构的化合物，其中具有下式（2）所示结构的化合物的含量为具有下式（1）和下式（2）所示结构的化合物的总含量的0.001％以上的染色组合物。 [在式（1）和（2）中，环Z1，环Z2，环Z3和环Z4分别独立地表示取代或未取代的复杂环，R1〜R6分别独立地表示氢原子，卤素原子或取代或未取代的烃基。但是，如果R1，R2，R4和R5存在多个，则可以相同或不同。p表示1或2，q表示p为1时大于等于2的整数，p为2时大于等于3的整数。]

表征谱图