1,5-二氯-4,8-二羟基蒽醌 | 6837-97-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 1,5-二氯-4,8-二羟基蒽醌
• 中文别名: 1,5-二羟基-4,8-二氯-9,10-蒽基二酮
• 英文名称: 1,5-dichloro-4,8-dihydroxyanthraquinone
• 英文别名: 1,5-Dichlor-4,8-dihydroxy-anthrachinon；4,8-dichloro-1,5-dihydroxyanthrachinone；9,10-Anthracenedione, 1,5-dichloro-4,8-dihydroxy-；1,5-dichloro-4,8-dihydroxyanthracene-9,10-dione
• CAS: 6837-97-4
• 化学式: C₁₄H₆Cl₂O₄
• 分子量: 309.105
• InChiKey: MVTQMYUSTKVGRP-UHFFFAOYSA-N

物化性质

• 沸点：
  423.87°C (rough estimate)
• 密度：
  1.4147 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2914700090

SDS

Name:	1 5-Dichloro-4 8-Dihydroxyanthracene-9 10- Dione Material Safety Data Sheet
Synonym:	Dichloroanthrarufin; 4,8-Dichloro-1,5-Dihydroxyanthraquinone
CAS:	6837-97-4

Section 1 - Chemical Product MSDS Name:1 5-Dichloro-4 8-Dihydroxyanthracene-9 10- Dione Material Safety Data Sheet
Synonym:Dichloroanthrarufin; 4,8-Dichloro-1,5-Dihydroxyanthraquinone

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
6837-97-4	9,10-Anthracenedione,1,5-Dichloro-4,8-	ca 100	229-924-4

Hazard Symbols: XN
Risk Phrases: 40

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Limited evidence of a carcinogenic effect.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.
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:
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:
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:
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# 6837-97-4: 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:
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: Not available.
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 0 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C14H6Cl2O4
Molecular Weight: 309.09

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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:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, oxides of chlorine.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 6837-97-4: CB6498500 LD50/LC50:
Not available.
Carcinogenicity:
9,10-Anthracenedione,1,5-Dichloro-4,8-Dihydroxy- - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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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 40 Limited evidence of a carcinogenic effect.
Safety Phrases:
S 28A After contact with skin, wash immediately with
plenty of water.
S 36/37 Wear suitable protective clothing and
gloves.
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# 6837-97-4: No information available.
Canada
CAS# 6837-97-4 is listed on Canada's NDSL List.
CAS# 6837-97-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 6837-97-4 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：

  1,5-二氯-4,8-二羟基蒽醌 在 硫酸 作用下， 生成 2,2'-[[(9,10-二氢-4,8-二羟基-9,10-二氧代蒽)-1,5-二基]二亚氨基]二(5-甲基苯磺酸)
  参考文献：
  名称：

  THE STRUCTURE OF THE SO-CALLED TOLUIDINE BLUE

  摘要：

  DOI：

  10.1021/jo01205a009
• 作为产物：
  描述：

  蒽绛酚 在 磺酰氯 作用下， 以 硝基苯 为溶剂， 反应 22.0h， 以49.5%的产率得到1,5-二氯-4,8-二羟基蒽醌
  参考文献：
  名称：

  Near infrared fluorophore for the selective labelling of membranes in cells

  摘要：

  本发明涉及一种作为荧光染料的蒽醌衍生物，以及生产该蒽醌衍生物的方法和它们作为荧光染料用于活细胞或固定细胞膜染色的用途。

  公开号：

  EP1905801A1

文献信息

• Structural modification study of mitoxantrone (DHAQ). Chloro-substituted mono- and bis[(aminoalkyl)amino]anthraquinones
  作者：Robert Zee-Cheng、Abraham E. Mathew、Pei-Ling Xu、Raymond V. Northcutt、C. C. Cheng

  DOI：10.1021/jm00392a028

  日期：1987.9

  chloro-substituted [(aminoalkyl)amino]anthraquinones were synthesized and evaluated for their antineoplastic and cytotoxic activity. Treatment of 5,8-dichloroquinizarin with substituted amines in pyridine resulted in the replacement of one halogen atom by the amino group to yield mainly 1-chloro-5,8-dihydroxy-4-(substituted amino)anthraquinones. On the other hand, reaction between the dichloroquinizarin and

  合成了许多氯取代的[（氨基烷基）氨基]蒽醌，并评估了它们的抗肿瘤和细胞毒性活性。用吡啶中的取代胺处理5,8-二氯喹啉，导致一个卤素原子被氨基取代，主要产生1-氯-5,8-二羟基-4-（取代的氨基）蒽醌。另一方面，二氯喹嗪林和丁醇中的胺之间的反应主要产生1，4-二氯-5-羟基-8-（取代的氨基）蒽醌。通过常规方法，用各种胺置换适当的蒽醌衍生物的氯，硝基或甲苯磺酰基官能团，制得该系列的其他化合物。1,4-二氯-5-羟基-8-[[[2-[（（2-羟基乙基）氨基]乙基]氨基]蒽醌（6b）对P388白血病具有最高的抑制活性。它对B16黑色素瘤和体外L1210筛选的抑制作用也很重要。其他几种被氯和羟基取代的氨基蒽醌（5a，5b和6a）在体内和体外对P388和L1210也表现出明显的活性。结构活性关系检查表明，羟基可能有助于某些氯氨基蒽醌的生物活性结合，[2-[（（2-羟乙基）氨基]乙基]氨基侧链似乎是比其他取代基更好的取代基。氨基侧链。
• Near infrared fluorophore for the selective labelling of membranes in cells
  申请人：Universität Heidelberg

  公开号：EP1905801A1

  公开（公告）日：2008-04-02

  The present invention relates to anthraquinone derivatives which act as a fluorophore, to a process for producing said anthraquinone derivatives and their use as fluorophores for staining membranes in live or fixed cells.

  本发明涉及一种作为荧光染料的蒽醌衍生物，以及生产该蒽醌衍生物的方法和它们作为荧光染料用于活细胞或固定细胞膜染色的用途。
• [EN] ANTI-CANCER COMPOUNDS
  申请人：NATIONAL RESEARCH DEVELOPMENT CORPORATION

  公开号：WO1991005824A1

  公开（公告）日：1991-05-02

  (EN) Compounds of formula (I) in which R1, R2, R3 and R4 are each separately selected from hydrogen, X, NH-A-NHR and NH-A-N(O)R'R'' wherein X is hydroxy, halogeno, amino, C1-4 alkoxy or C2-8 alkanoyloxy, A is a C2-4 alkylene group with a chain length between NH and NHR or N(O)R'R'' of a least 2 carbon atoms and R, R' and R'' are each separately selected from C1-4 alkyl groups and C2-4 hydroxyalkyl and C2-4 dihydroxyalkyl groups in which the carbom atom attached to the nitrogen atom does not carry a hydroxy group and no carbon atom is substituted by two hydroxy groups, or R' and R'' together are a C2-6 alkylene group which with the nitrogen atom to which R' and R'' are attached forms a heterocyclic group having 3 to 7 atoms in the ring, but with the proviso that at least one of R1 to R4 is a group NH-A-N(O)R'R'', and physiologically acceptable salts thereof are of value in the treatment of cancer.(FR) Composés de formule (I) où R1, R2, R3 et R4 sont chacun sélectionnés séparément à partir de l'hydrogène, X, NH-A-NHR et NH-A-A(O)R'R'' où X est hydroxy, halogéno, amino, C1-4 alkoxy ou C2-8 alkanoyloxy, A est un groupe alkylène C2-4 à longueur de chaîne entre NH et NHR ou N(O)R'R'' d'au moins deux atomes de carbone et R, R' et R'' sont chacun sélectionnés séparément à partir de groupes alkyle C1-4 et de groupes hydroxyalkyle C2-4 et dihydroxyalkyle C2-4 où l'atome de carbone attaché à l'atome d'azote ne porte pas de groupe hydroxy et aucun atome de carbone n'est substitué par deux groupes hydroxy, ou R' et R'' ensemble sont un groupe alkylène C2-6 qui, avec l'atome d'azote auquel R' et R'' sont attachés, forme un groupe hétérocyclique ayant de 3 à 7 atomes dans l'anneau mais sous condition qu'au moins l'un de R1 à R4 soit un groupe NH-A-N(O)R'R'' et que ses sels physiologiquement acceptables soient valables dans le traitement du cancer.

  化合物的化学式为（I），其中R1、R2、R3和R4分别独立地选择自氢、X、NH-A-NHR和NH-A-N（O）R'R''，其中X是羟基、卤素、氨基、C1-4烷氧基或C2-8烷酰氧基，A是C2-4烷基链，在NH和NHR或N（O）R'R''之间具有至少2个碳原子，R、R'和R''分别独立地选择自C1-4烷基和C2-4羟基烷基和C2-4二羟基烷基，其中连接氮原子的碳原子不带有羟基，且没有碳原子被两个羟基取代，或者R'和R''在一起是C2-6烷基链，与R'和R''附着的氮原子一起形成一个具有3到7个原子的杂环基团，但至少R1到R4中的一个是NH-A-N（O）R'R''的群，其生理上可接受的盐对于癌症的治疗具有价值。
• Verfahren zur Herstellung von Arylaminohydroxyanthrachinonen
  申请人：BAYER AG

  公开号：EP1074586A1

  公开（公告）日：2001-02-07

  Das neue Verfahren zur Herstellung von Arylaminohydroxyanthrachinon der Formel worin die Substituenten die in der Beschreibung angegebene Bedeutung haben, durch Umsetzung von entsprechendem Chlorhydroxyanthrachinon der Formel worin die Substituenten die in der Beschreibung angegebene Bedeutung haben, mit einem Amin der Formel (III)         H2N-Ar     (III), worin Ardie in der Beschreibung angegebene Bedeutung hat, ist dadurch gekennzeichnet, daß pro Chloratom in den Verbindungen der Formel (II) ein Mol Amin der Formel (III) zuzüglich eines Überschusses von 10 bis 100 % bezogen auf ein Mol Amin eingesetzt wird und die Umsetzung in Gegenwart einer Base, ausgewählt aus der Reihe der Carbonate der Alkali- und Erdalkalimetalle, der Acetate der Alkalimetalle, der Phosphate der Alkalimetalle oder beliebiger Mischungen davon, in einem inerten Lösungsmittel durchgeführt wird.

  制备式芳基氨基羟基蒽醌的新工艺 式中的相应氯羟基蒽醌反应制备芳基氨基羟基蒽醌的新工艺，其中取代基的含义如描述中所给定。 其中各取代基的含义见说明、 与式 (III) 的胺反应 H2N-Ar (III)、 其中 Arh 具有说明中给出的含义、 其特征在于：在式（II）化合物中，每个氯原子使用一摩尔式（III）胺和相对于一摩尔胺 10%至 100%的过量，反应在惰性溶剂中，在选自碱金属和碱土金属的碳酸盐、碱金属的醋酸盐、碱金属的磷酸盐或它们的混合物的碱存在下进行。
• Deuterated compounds and uses thereof
  申请人：Biostatus Limited

  公开号：US10385009B2

  公开（公告）日：2019-08-20

  An anthraquinone compound of formula I (such as the compounds of formulae II to X) and processes for making the same are provided. Pharmaceutical compositions for use in the treatment of cancer, optionally in combination with an agent capable of reducing the level of oxygenation of a tumor, are also provided. Additionally, an option for combination with chemotherapeutic and radiotherapeutic modalities to enhance overall tumor cell kill is provided. Methods for the detection of cellular hypoxia, both in vivo and in vitro, are additionally provided.

  提供了式 I 的蒽醌化合物（如式 II 至 X 的化合物）及其制造工艺。还提供了用于治疗癌症的药物组合物，可选择与能够降低肿瘤氧合水平的制剂结合使用。此外，还提供了一种与化疗和放射治疗方式相结合的方案，以增强对肿瘤细胞的整体杀伤力。此外，还提供了体内和体外检测细胞缺氧的方法。

表征谱图