对位红 | 6410-10-2

• 物质功能分类: 分析化学 - 标准品 - 食品和饮料标准品
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 对位红
• 中文别名: 1-(4-硝基苯基偶氮)-2-萘酚)(对位红)；对硝基苯胺红；C.I.颜料红1；1-(4-硝基苯基偶氮)萘-2-醇；1-(4-硝基苯基偶氮)-2-萘酚；对位红/1-(4-硝基苯基偶氮)-2-萘酚
• 英文名称: para red
• 英文别名: 1-(4-nitrophenylazo)-2-naphthol；1-((4-nitrophenyl)diazenyl)naphthalen-2-ol；pigment red 1；1-[(4-nitrophenyl)diazenyl]naphthalen-2-ol
• CAS: 6410-10-2
• 化学式: C₁₆H₁₁N₃O₃
• mdl: MFCD00003908
• 分子量: 293.282
• InChiKey: WOTPFVNWMLFMFW-UHFFFAOYSA-N

物化性质

• 熔点：
  248-252 °C
• 沸点：
  435.13°C (rough estimate)
• 密度：
  1.2211 (rough estimate)
• 溶解度：
  DMSO（稍微加热）

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  90.8
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• TSCA：
  Yes
• 危险品标志：
  Xi
• 安全说明：
  S24/25,S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2927000090
• RTECS号：
  QL4510000
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温

SDS

Name:	Para red dye content ca. 95% Material Safety Data Sheet
Synonym:	1-(4-Nitrophenylazo)-2-naphthol; 1-((4-Nitrophenyl)azo)-2-naphthol; 1-(p-Nitrophenylazo)-2-naphthol; 2-Naphthalenol, 1-((4-nitrophenyl)azo)-; 2-Naphthol, 1-((4-nitrophenyl)azo)
CAS:	6410-10-2

Section 1 - Chemical Product MSDS Name:Para red dye content ca. 95% Material Safety Data Sheet
Synonym:1-(4-Nitrophenylazo)-2-naphthol; 1-((4-Nitrophenyl)azo)-2-naphthol; 1-(p-Nitrophenylazo)-2-naphthol; 2-Naphthalenol, 1-((4-nitrophenyl)azo)-; 2-Naphthol, 1-((4-nitrophenyl)azo)

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
6410-10-2	Para Red	ca. 95	229-093-8

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
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:
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. 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# 6410-10-2: 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: Powder
Color: red
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 248.00 - 252.00 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: C16H11N3O3
Molecular Weight: 293.27

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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, nitrogen.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 6410-10-2: QL4510000 LD50/LC50:
Not available.
Carcinogenicity:
Para 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
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.
WGK (Water Danger/Protection)
CAS# 6410-10-2: No information available.
Canada
CAS# 6410-10-2 is listed on Canada's NDSL List.
CAS# 6410-10-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 6410-10-2 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

对位红是一种显色颜料，呈现暗红色固体状态。在120℃以上温度下会变暗。其熔点为256℃。对位红难溶于水，微溶于热甲苯及热乙醇，并能溶解于10%的热氢氧化钠水溶液中。通常通过将对硝基苯胺重氮化后，在冰浴中与β-萘酚反应制备得到。

用途方面，对位红主要用于测定辣椒酱、辣酱油等复杂样品中的残留量。

反应信息

• 作为反应物：
  描述：

  对位红 在 sodium sulfide 、 sodium hydroxide 作用下， 以 水 为溶剂， 以92%的产率得到1-(4-aminophenylazo)naphthalen-2-ol
  参考文献：
  名称：

  质谱分析取代基对1-芳基氮杂萘-2-醇互变异构的影响

  摘要：

  获得了一系列1-芳基氮杂萘-2-醇的电子电离（EI）质谱图，以研究取代基对碎片的影响。比率，分子离子和碎片离子之间的相关性以及Hammett常数用于检查取代基对碎片的影响。I分子离子/（I 171amu + I 143amu + I 115amu）之比与Hammett常数之间的负校正表示吸电子基团使分子离子不稳定。异常的远距离氢转移显示了在裂解过程中的重要作用

  DOI：

  10.1002/jccs.201400305
• 作为产物：
  描述：

  4-硝基氯化重氮苯 在 乙醇 作用下， 生成 对位红
  参考文献：
  名称：

  Hantzsch; Schultze, Chemische Berichte, 1895, vol. 28, p. 674

  摘要：

  DOI：

文献信息

• One-pot synthesis of azo compounds in the absence of acidic or alkaline additives
  作者：Ting-Ting Liu、Jiao-Zhao Yan、Xin-Wang Cheng、Pan Duan、Yao-Fu Zeng

  DOI：10.1177/1747519820964182

  日期：2021.5

  A one-pot method for the synthesis of azo compounds by the reaction of β-naphthol with aryl amines using t-BuONO as the nitrosonium source in DCM at room temperature was developed. This method feat...

  开发了一种以 t-BuONO 作为亚硝鎓源在室温下在 DCM 中通过 β-萘酚与芳胺反应合成偶氮化合物的一锅法。这种方法壮...
• Two-Phase Electrochemical Generation of Aryldiazonium Salts: Application in Electrogenerated Copper-Catalyzed Sandmeyer Reactions
  作者：Hamed Goljani、Zahra Tavakkoli、Ali Sadatnabi、Davood Nematollahi

  DOI：10.1021/acs.orglett.0c02013

  日期：2020.8.7

  compounds including azo, azosulfone, and arylazides were prepared in good yields with good purity. Cathodically generated aryldiazoniums and anodically produced copper(Ι) ions were used to perform Sandmeyer reactions. To improve the method, an H-type self-driving cell equipped with a Zn rod as an anode was introduced and used for two-phase aryldiazonium production.

  首次报道了在两相系统（乙酸乙酯/水）中由硝基芳烃电化学生成芳基重氮盐。以良好的收率和良好的纯度制备了包括偶氮，偶氮砜和芳基叠氮化物在内的一些化合物。阴极产生的芳基重氮和阳极产生的铜（I）离子用于进行Sandmeyer反应。为了改进该方法，引入了以Zn棒为阳极的H型自驱动电池，并将其用于两相芳基重氮的生产。
• Fluorescent azo disperse dyes from 3-(1,3-benzothiazol-2-yl)naphthalen-2-ol and comparison with 2-naphthol analogs
  作者：Manjaree A. Satam、Rajesh K. Raut、N. Sekar

  DOI：10.1016/j.dyepig.2012.07.019

  日期：2013.1

  Five novel fluorescent azo disperse dyes were synthesized using different diazotized aromatic amines followed by coupling with 3-(1,3-benzothiazol-2-yl)naphthalen-2-ol. These dyes were characterized by FT-IR, 1H NMR and mass spectroscopy. These azo disperse dyes were applied on polyester and their fastness properties were evaluated. A parallel series of dyes using 2-naphthol in place of benzothiazolyl

  使用不同的重氮化芳族胺，然后与3-（1,3-苯并噻唑-2-基）萘-2-醇偶联，合成了五种新颖的荧光偶氮分散染料。这些染料通过FT-IR，1 H NMR和质谱进行表征。将这些偶氮分散染料涂在聚酯上并评估其坚牢度。用2-萘酚代替苯并噻唑基制备了一系列平行的染料，以研究苯并噻唑基部分对牢度性能的影响。该研究表明，含有苯并噻唑基残基的染料具有比基于2-萘酚的偶氮分散染料更好的坚牢度性能。还研究了pH对光物理性质的影响。
• 利用固体颗粒一锅法合成偶氮化合物的方法
  申请人：天津大学

  公开号：CN108912723A

  公开（公告）日：2018-11-30

  本发明涉及一种利用固体颗粒一锅法合成偶氮化合物的方法，向反应容器内加入固体颗粒，再加入无机酸、芳香伯胺、亚硝酸钠、水和偶合组分，并机械搅拌，监测反应完成后过滤并漂洗，滤饼即为产品。或者向反应容器内加入固体颗粒，再加入无机酸、芳香伯胺、亚硝酸钠和水，并机械搅拌，芳香伯胺完全转化后再加入偶合组分，继续机械搅拌监测反应完成后过滤并漂洗，滤饼即为产品。固体颗粒优选为聚四氟乙烯颗粒、山楂籽或不锈钢沙。该方法通过向反应体系中加入固体颗粒促进反应，无需预热溶解或加碱溶解重氮组分或偶合组分。大多数反应在1小时之内完成，反应时间短，产品纯度高；反应滤液及过量的无机酸可多次循环利用。
• Synthesis of a nitrite functionalized star-like poly ionic compound as a highly efficient nitrosonium source and catalyst for the diazotization of anilines and subsequent facile synthesis of azo dyes under solvent-free conditions
  作者：Hassan Valizadeh、Ashkan Shomali、Jalal Ghorbani、Saeideh Noorshargh

  DOI：10.1016/j.dyepig.2015.02.007

  日期：2015.6

  star-like poly ionic (NFSPI) compound was synthesized and used as a highly efficient nitrosonium source and catalyst for the conversion of aniline derivatives to diazonium salts. Azo dyes were prepared via in situ azo-coupling reaction of these diazoniums with active aromatic compounds under solvent-free conditions in very short reaction time in excellent yields. NFSPI plays dual role as a three-dimensional

  合成了亚硝酸盐官能化的星形聚离子（NFSPI）化合物，并将其用作高效的硝态氮源和催化剂，用于将苯胺衍生物转化为重氮盐。偶氮染料是通过在没有溶剂的条件下，这些重氮鎓与活性芳香族化合物在非常短的反应时间内以极高的收率进行原位偶氮偶合反应而制备的。NFSPI由于具有多离子特性，因此可作为三维硝态氮源和催化剂发挥双重作用。分离出的产物经FT-IR光谱，1 H-NMR，13确证。C-NMR光谱和CHNSO分析。通过FT-IR光谱，SEM图像，EDX和CHNSO分析确认了非均相试剂和催化剂的结构。通过该程序合成各种产物的产率和反应时间与文献报道的值进行了比较。