玫瑰红酸二水合物 | 118-76-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 玫瑰红酸二水合物
• 中文别名: 玫琮酸；玫琮酸二水合物；5,6-二羥-5-環己烯四酮；玫棕酸
• 英文名称: rhodizonic acid
• 英文别名: Rhodizonsaeure；5,6-dihydroxycyclohex-5-ene-1,2,3,4-tetrone
• CAS: 118-76-3
• 化学式: C₆H₂O₆
• mdl: MFCD00001651
• 分子量: 170.078
• InChiKey: WCJLIWFWHPOTAC-UHFFFAOYSA-N

物化性质

• 熔点：
  248 °C (dec.)(lit.)
• 沸点：
  259.67°C (rough estimate)
• 密度：
  1.7636 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2914400090

SDS

Name:	Rhodizonic Acid Dihydrate Material Safety Data Sheet
Synonym:	None.
CAS:	118-76-3

Section 1 - Chemical Product MSDS Name: Rhodizonic Acid Dihydrate Material Safety Data Sheet
Synonym: None.

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SECTION 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
118-76-3	Rhodizonic Acid Dihydrate	ca 100	204-276-5

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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SECTION 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW 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 irritation of the digestive tract. 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.
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.
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:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. 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. Use with adequate ventilation. Minimize dust generation and accumulation. 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. Exposure Limits CAS# 118-76-3: 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: Powder
Color: brown
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Decomposes
Freezing/Melting Point: 255.00 - 257.00 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: > 257 deg C
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C6H2O6.2H2O
Molecular Weight: 206.11

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

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SECTION 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 118-76-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Rhodizonic Acid Dihydrate - 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: Not available.
Risk Phrases:
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# 118-76-3: No information available. Canada None of the chemicals in this product are listed on the DSL/NDSL list. CAS# 118-76-3 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 118-76-3 is not listed on the TSCA inventory. It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
MSDS Creation Date: 2/05/1999 Revision #2 Date: 3/18/2003 The information above is believed to be accurate and represents the best information currently available to us. However, we make no warranty of merchantability or any other warranty, express or implied, with respect to such information, and we assume no liability resulting from its use. Users should make their own investigations to determine the suitability of the information for their particular purposes. In no way shall the company be liable for any claims, losses, or damages of any third party or for lost profits or any special, indirect, incidental, consequential or exemplary damages, howsoever arising, even if the company has been advised of the possibility of such damages.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  玫瑰红酸二水合物 在 barium hydroxide octahydrate 作用下， 以 水 为溶剂， 反应 1.5h， 以96%的产率得到barium rhodizonate
  参考文献：
  名称：

  μ-Rhodizonato-1κO,1:2κO',2κO''-tetra(triphenylphosphine)disilver(I)：具有[C6O6]2-配体模板的分子复合物

  摘要：

  呈现了第一种玫瑰红酸银和第四种过渡金属玫瑰红酸配合物。标题化合物显示了迄今为止未观察到的玫瑰红配体的配位模式，该模式因平面性而异样地扭曲。结构讨论伴随着对迄今为止在结构上表征的玫瑰红盐和配合物的全面文献综述。

  DOI：

  10.1002/zaac.201500589
• 作为产物：
  描述：

  玫瑰红酸二水合物 140.0 ℃ 、0.13 Pa 条件下， 生成 玫瑰红酸二水合物
  参考文献：
  名称：

  13 C-NMR。环状碳氧化合物的光谱，结构和反应性† ‡

  摘要：

  通过13 C-NMR研究了在不同溶剂中环状聚酮的结构，它们的水合物和还原产物。光谱学。在二甲亚砜溶液中，Rhodizonic acid （1），croconic acid （2）和方酸（3）显示信号平均。在无水四氢呋喃1和2中可以观察到非动态物种。十二羟基环己烷（5）和十羟基环戊烷（'leuconic酸'）（6）的自发反应并研究了环缩产物的形成顺序。可以清楚地识别出关键的中间体，这些中间体支持了先前提出的机制，该机制涉及苯甲酸类型的重排，然后进行脱羧和随后的氧化还原反应。

  DOI：

  10.1002/hlca.19770600325
• 作为试剂：
  描述：

  苯甲酰甲酸甲酯 在 玫瑰红酸二水合物 1-苯甲基-1,4-二氢烟酰胺 作用下， 以 水 、 乙腈 为溶剂， 反应 120.0h， 生成 DL-扁桃酸甲酯
  参考文献：
  名称：

  在存在Rhodizonic acid的情况下，通过还原的烟酰胺腺嘌呤二核苷酸模型还原苯甲酰基甲酸甲酯

  摘要：

  在室温下用1-苄基-1,4-二氢烟碱酰胺（BNAH; NADH模型）还原Rhodizonic acid（RA），得到四羟基对醌（THQ）和六羟基苯（HHB）。二电子还原和四电子还原。在存在RA的情况下，用BNAH进行的苯甲酰甲酸酯的还原反应进行得很顺利，但没有RA则无法完全还原。

  DOI：

  10.1016/s0040-4039(00)84055-1

文献信息

• Luminescent compounds
  申请人：——

  公开号：US20030235846A1

  公开（公告）日：2003-12-25

  Luminescent compounds, reactive intermediates used to synthesize luminescent compounds, and methods of synthesizing and using luminescent compounds. These compounds may be based on squaric, croconic, and rhodizonic acid, and their analogs, among others, and relate generally to the structure: 1 where Z is a four, five, or six-member aromatic ring, and A, B, C, D, E, and F are substituents of Z, in any order, that may include O, S, Se, Te, C(R a )(R b ), N-R c , N(R d )(R e ), W 1 , and W 2 . Generally, each compound includes at least one of W 1 or W 2 , where W 1 and W 2 have the structures: 2 respectively. The compounds may include a reactive group and/or a carrier. The luminescent compounds may be useful in both free and conjugated forms as probes, labels, and/or indicators.

  发光化合物，用于合成发光化合物的反应中间体，以及合成和使用发光化合物的方法。这些化合物可能基于方酰、克罗酰和罗地酮酸及其类似物等，通常与结构相关：其中Z是一个四、五或六元芳香环，而A、B、C、D、E和F是Z的取代基，可以包括O、S、Se、Te、C(Ra)(Rb)、N-Rc、N(Rd)(Re)、W1和W2，顺序任意。通常，每种化合物至少包括W1或W2中的一种，其中W1和W2的结构分别为：。这些化合物可能包括一个反应基团和/或一个载体。这些发光化合物可能在自由和共轭形式下作为探针、标记物和/或指示剂而有用。
• Insertion von Rhodizonsäure in die Gallium-Gallium- bzw. Indium-Indium-Bindungen von Digallan(4)- bzw. Diindan(4)-Verbindungen
  作者：Werner Uhl、Malte Prött

  DOI：10.1002/1521-3749(200211)628:11<2259::aid-zaac2259>3.0.co;2-c

  日期：2002.11

  l] digallan(4) (1) und der entsprechenden Diindiumverbindung (2) unter Oxidation der Gallium- bzw. Indiumatome von +II nach +III. Ein Protonentransfer zu den elementorganischen Gruppen findet nicht statt, vielmehr insertiert sich die Saure vollstandig in die Element-Element-Bindungen. Die Dialkylgallium- bzw. Dialkylindiumreste der Produkte (3 (Ga) und 4 (In)) werden durch jeweils zwei Sauerstoffatome

  Rhodizonsaure (C6O6H2, 5, 6-Dihydroxy-5-cyclohexen-1, 2, 3, 4-tetraon) reagiert mit Tetrakis[bis(trimethylsilyl)-methyl] digallan(4) (1) und der entsprechenden Diindiumverbindung (2) unter氧化 der 镓 - bzw。Indiumatome von +II nach +III。Ein Protonentransfer zu den elementorganischen Gruppen findet nicht statt, vielmehr insertiert sich die Saure vollstandig in die Element-Element-Bindungen。模具二烷基镓-bzw。Dialkylindiumreste
• Smectic liquid crystals based on hexaazatriphenylene: potential organic n-type semiconductor
  作者：Baoxiang Gao、Licui Zhang、Qianqian Bai、Ying Li、Junwei Yang、Lixiang Wang

  DOI：10.1039/c0nj00586j

  日期：——

  We report the synthesis of dibenzohexaazatriphenylene derivative DBHAT. The addition of electron-withdrawing groups on the dibenzohexaazatriphenylene core leads to a high electron-accepting capability. DBHAT exhibits reversible four-step reduction waves at half-wave potentials (E1/2) of −0.42, −0.94, −1.35 and −1.80 V vs. Ag/AgCl. Furthermore, DBHAT is able to form a smectic liquid crystalline assembly over a wide temperature range. With strong dipole–dipole interactions, the smectic liquid crystals show extremely highly stabilized mesophases.

  我们报道了二苯并六氮杂三苯ylene衍生物 DBHAT 的合成。在二苯并六氮杂三苯ylene 核心上添加电子吸引基团，导致其具有高电子受体能力。DBHAT 在相对于 Ag/AgCl 的半波电位（E1/2）为 -0.42、-0.94、-1.35 和 -1.80 V 处表现出可逆的四步还原波。此外，DBHAT 能够在较宽温度范围内形成 smectic 液晶组装。由于强偶极-偶极相互作用，smectic 液晶显示出极高稳定性的介相。
• Synthesis and Optical Properties of Unsymmetrically Substituted Triarylamine Hexaazatrinaphthalenes
  作者：Christopher B. Larsen、Jonathan E. Barnsley、Holly van der Salm、Michael G. Fraser、Nigel T. Lucas、Keith C. Gordon

  DOI：10.1002/ejoc.201700251

  日期：2017.5.3

  We report herein the synthesis and optical properties of unsymmetrically substituted hexaazatrinaphthalene (HATN) systems, and the influence of donor additivity on the electronic properties of the material. The hexaazatrinaphthalenes have been studied by means of electrochemical, electronic absorption and emission, FT Raman and resonance Raman methodologies coupled with DFT calculations. The optical

  我们在此报告了不对称取代的六氮杂三萘 (HATN) 系统的合成和光学特性，以及供体可加性对材料电子特性的影响。已通过电化学、电子吸收和发射、FT 拉曼和共振拉曼方法以及 DFT 计算对六氮杂萘进行了研究。光谱主要由低能电荷转移态主导，随着供体数量的增加，激发能的红移约为 0.1 eV，e 增加约 125%。发射光谱表现出显着的溶剂化变色，Lippert-Mataga 分析产生的 Δµ 值介于 34 和 60 D 之间。
• Reversible solid-state interconversion of rhodizonic acid H₂C₆O₆into H₆C₆O₈and the solid-state structure of the rhodizonate dianion C₆O₆²⁻(aromatic or non-aromatic?)
  作者：Dario Braga、Gianna Cojazzi、Lucia Maini、Fabrizia Grepioni

  DOI：10.1039/b107317f

  日期：——

  Anhydrous rhodizonic acid H2C6O6 is obtained by (fully reversible) thermal dehydration of solid 2,3,5,5,6,6-hexahydroxycyclohex-2-ene-1,4-dione, H6C6O8, commonly known as rhodizonic acid dihydrate. Treatment of H6C6O8 with RbOH yields crystals of Rb2C6O6; the oxocarbon dianion C6O62− is shown to possess a flat, benzene-type structure, with C–C bonds shorter than expected for a (non-aromatic) ketonic-type

  无水Rhodizonic酸H 2 C 6 O 6通过固体的（完全可逆）热脱水获得2,3,5,5,6,6-六羟基环己-2-烯-1,4-二酮，H 6 C 6 O 8，通常称为二水杜鹃花酸。用RbOH处理H 6 C 6 O 8产生Rb 2 C 6 O 6晶体; 这碳氧化合物二价阴离子C 6 O 6 2− 显示为具有平面，苯型结构，CC键比（非芳香族）酮型结构的预期短。

表征谱图