甲基红 | 493-52-7

• 物质功能分类: 生物化工 - 生化试剂 - 酸碱指示剂
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 中文名称: 甲基红
• 中文别名: 酸性红2；甲基；对二甲氨基偶氮苯邻羧酸；2-[[4-(二甲基氨基)苯基]偶氮基]苯甲酸；酸性红 2；对二甲氨基偶氮苯邻羟酸；甲红；甲烷红；烷红
• 英文名称: methyl red
• 英文别名: 2-(4-dimethylaminophenylazo)benzoic acid；acid red 2；2-[(4-(dimethylamino)phenyl)diazenyl]-benzoic acid；2-(N,N-dimethyl-4-aminophenyl)azobenzenecarboxylic acid；2-[[4-(dimethylamino)phenyl]diazenyl]benzoic acid
• CAS: 493-52-7
• 化学式: C₁₅H₁₅N₃O₂
• 分子量: 269.303
• InChiKey: CEQFOVLGLXCDCX-UHFFFAOYSA-N

物化性质

• 熔点：
  179-182 °C (lit.)
• 沸点：
  412.44°C (rough estimate)
• 密度：
  0.839 g/mL at 25 °C
• 蒸气密度：
  9.3 (vs air)
• 闪点：
  11 °C
• 溶解度：
  乙醇：可溶1mg/mL
• 最大波长(λmax)：
  410nm, 530nm, 427nm, 519nm
• 物理描述：
  Violet crystals; [Sax]
• 颜色/状态：
  GLISTENING, VIOLET CRYSTALS FROM TOLUENE
• 蒸汽压力：
  0.00000014 [mmHg]
• 解离常数：
  PKA1 2.5; PKA2 9.5; PKB 4.8
• 稳定性/保质期：
  1. 按照规定使用和存放，不会发生分解，请避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  65.3
• 氢给体数：
  1
• 氢受体数：
  5

ADMET

代谢

甲基红在微生物中代谢成了邻氨基苯甲酸和对二甲氨基偶氮苯。SCHELINE RR, 药物毒理学学报, 26, 332 (1968)。GINGELL R, 异生物学报, 3, 165 (1973)。

METHYL RED IN MICRO-ORGANISM /WAS METABOLIZED TO/ ANTHRANILIC ACID & N,N-DIMETHYL-P-PHENYLENEDIAMINE. SCHELINE RR, ACTA PHARMAC TOX, 26, 332 (1968). GINGELL R, XENOBIOTICA, 3, 165 (1973).

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌性证据

没有关于人类的数据。动物致癌性证据不足。总体评估：第3组：该物质对人类致癌性无法分类。

No data are available in humans. Inadequate evidence of carcinogenicity in animals. OVERALL EVALUATION: Group 3: The agent is not classifiable as to its carcinogenicity to humans.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 致癌物分类

国际癌症研究机构致癌物：甲基红

IARC Carcinogenic Agent:Methyl red

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构（IARC）致癌物分类：第3组：无法归类其对人类致癌性

IARC Carcinogenic Classes:Group 3: Not classifiable as to its carcinogenicity to humans

来源:International Agency for Research on Cancer (IARC)

毒理性

• 致癌物分类

国际癌症研究机构专著：第8卷（1975年）一些芳香偶氮化合物

IARC Monographs:Volume 8: (1975) Some Aromatic Azo Compounds

来源:International Agency for Research on Cancer (IARC)

毒理性

• 相互作用

硫酸吲哚酚会降低O-甲基红与人血清白蛋白的结合。月桂酸和肉豆蔻酸都能降低O-甲基红的结合，这表明脂肪酸可能参与降低在尿毒症中发生的药物结合。

INDOXYL SULFATE DECR BINDING OF O-METHYL RED TO HUMAN SERUM ALBUMIN. LAURIC ACID & MYRISTIC ACID BOTH DECR O-METHYL RED BINDING, SUGGESTING THAT FATTY ACIDS MAY BE INVOLVED IN DECR DRUG BINDING WHICH OCCURS IN UREMIA.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

甲基红与牛血清白蛋白结合...

METHYL RED IS BOUND TO BOVINE SERUM ALBUMIN...

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• TSCA：
  Yes
• 危险等级：
  3
• 危险品标志：
  Xn
• 安全说明：
  S36/37
• 危险类别码：
  R68,R20/21/22,R10
• WGK Germany：
  1,2
• 海关编码：
  29270000
• 危险品运输编号：
  UN 1170
• 危险性防范说明：
  P261,P301+P312,P302+P352,P304+P340,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  -20℃密封保存，放置于通风、干燥的环境。

SDS

Name:	Methyl Red reagent ACS Material Safety Data Sheet
Synonym:	C.I. Acid Red 2; 2-(4-Dimethylaminophenylazo)benzoic acid; C.I. 13020; p-(Dimethylamino)azobenzene-o-carboxylic acid; Methyl Red
CAS:	493-52-7

Section 1 - Chemical Product MSDS Name:Methyl Red reagent ACS Material Safety Data Sheet
Synonym:C.I. Acid Red 2; 2-(4-Dimethylaminophenylazo)benzoic acid; C.I. 13020; p-(Dimethylamino)azobenzene-o-carboxylic acid; Methyl Red

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
493-52-7	Methyl Red	98	207-776-1

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
Contact may cause transient eye irritation. This product contains an anionic dye. Similar dyes have not caused injury to the cornea or conjunctiva in documented exposure cases with human or rabbit eyes.
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:
Chronic exposure may cause liver damage.

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Section 4 - FIRST AID MEASURES
Eyes: In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Get medical aid.
Skin:
In case of contact, flush skin with plenty of water. Remove contaminated clothing and shoes. Get medical aid if irritation develops and persists. Wash clothing before reuse.
Ingestion:
If swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
If inhaled, remove to fresh air. 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. Combustion generates toxic fumes. This material in sufficient quantity and reduced particle size is capable of creating a dust explosion.
Extinguishing Media:
For small fires, use water spray, dry chemical, carbon dioxide or chemical 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, then place into a suitable container for disposal. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation.
Storage:
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# 493-52-7: 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 minimize contact with skin.
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: Solid
Color: dark red to purple
Odor: none reported
pH: Not available.
Vapor Pressure: Negliglble.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 179-182 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: Insoluble in water.
Specific Gravity/Density: Not available.
Molecular Formula: C15H15N3O2
Molecular Weight: 269.30

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures. Materials containing similar functional groups can decompose at elevated temperatures.
Conditions to Avoid:
Dust generation, excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 493-52-7: DG8960000 LD50/LC50:
Not available.
Carcinogenicity:
Methyl Red - 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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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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.
WGK (Water Danger/Protection)
CAS# 493-52-7: 2
Canada
CAS# 493-52-7 is listed on Canada's DSL List.
CAS# 493-52-7 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 493-52-7 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

化学性质
甲基红呈现为有光泽的紫色结晶或红棕色粉末，熔点在180-182℃。它易溶于乙醇和冰醋酸，几乎不溶于水。

用途
甲基红是一种常用的酸碱指示剂，常配制成0.1%的乙醇溶液，其pH变色范围为4.4（红色）至6.2（黄色），广泛用于原生动物活体染色及临床血清蛋白生化检验。此外，它还可以滴定氨、弱有机碱和生物碱，但不适合用于除草酸和苦味酸以外的有机酸；可与溴甲酚绿和亚甲基蓝组成混合指示剂以缩短变色域并提高变色敏锐性。另外，甲基红也可用作沉淀滴定的吸附指示剂，例如在硝酸钍滴定氟离子时使用，还可用于检定游离氯、亚氯酸盐等氧化剂。

生产方法
由邻氨基苯甲酸进行重氮化后，再与N,N-二甲基苯胺反应即可制得甲基红。

反应信息

• 作为反应物：
  描述：

  甲基红 在 一水合肼 作用下， 以 乙醇 为溶剂， 以92%的产率得到N,N-二甲基-对苯二胺
  参考文献：
  名称：

  水合肼未催化的偶氮芳烃还原裂变为氨基芳烃

  摘要：

  摘要 各种偶氮芳烃与水合肼在回流乙醇中发生还原裂变，得到易于分离的氨基芳烃，无需使用任何专门的催化剂。该反应快速且具有成本效益，收率非常好（85-95%）。‒OH、-OCH3、-COOH、-Cl 和-Br 等取代基不受影响。该方法提供了一种制备氨基芳烃的优雅途径。

  DOI：

  10.1081/scc-200051672
• 作为产物：
  描述：

  邻氨基苯甲酸 在 盐酸 、 sodium nitrite 作用下， 生成 甲基红
  参考文献：
  名称：

  Rupp; Loose, Chemische Berichte, 1908, vol. 41, p. 3906

  摘要：

  DOI：
• 作为试剂：
  描述：

  3-bromo-6-chloro-2-hydroxybenzaldehyde 在 titanium(IV) isopropylate 、 盐酸 、 sodium hydroxide 、 盐酸羟胺 、 三甲基铝 、 sodium cyanoborohydride 、 potassium carbonate 、 甲基红 、 calcium chloride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.42h， 生成 (3S,4R,5R)-2-[(3-bromo-6-chloro-2-methoxyphenyl)methyl]-4-[(1S)-1-hydroxyethyl]-5-(hydroxymethyl)-N-[(1S,2S,3S,5R)-2,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]-1,2-oxazolidine-3-carboxamide
  参考文献：
  名称：

  Compounds and Methods for Inhibiting the Interaction of BCL Proteins with Binding Partners

  摘要：

  该发明涉及含有结合到Bcl蛋白并抑制Bcl功能的异氧杂环丙氨酸化合物。这些化合物可用于治疗和调节与过度增殖相关的疾病，如癌症。

  公开号：

  US20080114167A1

文献信息

• Fullerene-Catalyzed Reduction of Azo Derivatives in Water under UV Irradiation
  作者：Yong Guo、Wengang Li、Jingjing Yan、Basem Moosa、Ma'an Amad、Charles J. Werth、Niveen M. Khashab

  DOI：10.1002/asia.201200701

  日期：2012.12

  catalyst for the reduction of azo groups in basic aqueous solution under UV irradiation in the presence of NaBH4. Use of NaBH4 by itself is not sufficient to reduce the azo dyes without the assistance of a metal catalyst such as Pd and Ag. Experimental and theoretical results suggest that C60 catalyzes this reaction by using its vacant orbital to accept the electron in the bonding orbital of azo dyes, which

  发现无金属的富勒烯（C 60）是在NaBH 4存在下在UV辐射下碱性水溶液中偶氮基团还原的有效催化剂。在没有金属催化剂例如Pd和Ag的辅助下，仅使用NaBH 4不足以还原偶氮染料。实验和理论结果表明，C 60通过利用其空轨道接受偶氮染料键合轨道中的电子来催化该反应，从而激活NN键。紫外线辐射提高了C 60与偶氮染料中电子给体部分相互作用的能力。
• Reductive cleavage of azo compounds catalyzed by commercial zinc dust using ammonium formate or formic acid
  作者：Shankare Gowda、K Abiraj、D.Channe Gowda

  DOI：10.1016/s0040-4039(01)02370-x

  日期：2002.2

  Azo compounds, both symmetric and unsymmetric, are cleaved to amine(s) by using commercial zinc dust and ammonium formate or formic acid in methanol, tetrahydrofuran or dioxane at room temperature. The reductive cleavage occurs without hydrogenolysis or hydrogenation of reducible moieties, such as -OH, -CH3, -OCH3, -COOH, -COCH3, halogen, etc. The cleavage is very fast, clean, cost effective and high-yielding

  在室温下，使用甲醇，四氢呋喃或二恶烷中的商品锌粉和甲酸铵或甲酸，可将对称和不对称的偶氮化合物裂解为一种或多种胺。还原裂解不发生可水解部分例如-OH，-CH 3，-OCH 3，-COOH，-COCH 3，卤素等的氢解或氢化而进行。该裂解非常快速，清洁，成本有效并且高产率。与早期方法相比，例如在石棉上使用环己烯/ 5％Pd的方法，环己烯/ 10％PdC或肼/ 10％PdC或阮内镍的方法。
• Reductive Cleavage of Azo Compounds by Zinc and Ammonium Chloride
  作者：M. B. Sridhara、G. R. Srinivasa、D. Channe Gowda

  DOI：10.1081/scc-120030694

  日期：2004.12.31

  Abstract Azo compounds are reduced to corresponding anilines with zinc dust in the presence of ammonium chloride in methanol at room temperature.

  摘要 在氯化铵的存在下，在甲醇中室温下，偶氮化合物被锌粉还原为相应的苯胺。
• A matrix metalloproteinase activation probe for painting human tumours
  作者：Bethany Mills、Dominic Norberg、Kevin Dhaliwal、Ahsan R Akram、Mark Bradley、Alicia Megia-Fernandez

  DOI：10.1039/d0cc03886e

  日期：——

  A probe that allows specific ‘painting’ of human tumours is described. Probe activation was mediated by specific matrix metalloproteinases, resulting not only in disruption of a FRET pair, but in the generation of a fragment that “fluorescently paints” human tumours. This probe demonstrated rapid and effective human tumour labelling with the potential to allow margin detection during surgical resection

  描述了一种允许对人类肿瘤进行特定“涂装”的探针。探针激活是由特定的基质金属蛋白酶介导的，不仅导致FRET对的破坏，而且导致“荧光描绘”人类肿瘤的片段的产生。该探针显示了快速有效的人类肿瘤标记，并有望在手术切除过程中进行切缘检测。
• [EN] FRET MOLECULAR PROBES WITH CLEAVABLE LINKERS FOR DETECTING BACTERIA AND/OR FUNGI IN VITRO AND IN VIVO<br/>[FR] SONDES MOLÉCULAIRES FRET AVEC LIEURS CLIVABLES PERMETTANT DE DÉTECTER DES BACTÉRIES ET/OU DES CHAMPIGNONS, IN VITRO ET IN VIVO
  申请人：UNIV EDINBURGH

  公开号：WO2016075481A1

  公开（公告）日：2016-05-19

  An optical probe is provided comprising a probe element connected to a quencher by a cleavable linker; the probe element comprising a binding moiety, and a fluorophore being substantially fluorescently quenched by the quencher when the probe element is connected to the quencher by the cleavable linker; wherein the probe element is separated from the quencher when the cleavable linker is cleaved. Methods of using the probe are also provided.

  提供了一种光学探针，包括通过可切割连接物连接到猝灭剂的探针元件；所述探针元件包括结合基团和荧光物质，当通过可切割连接物将探针元件连接到猝灭剂时，荧光物质被猝灭剂大幅熄灭荧光；当可切割连接物被切割时，探针元件与猝灭剂分离。还提供了使用该探针的方法。

表征谱图