4-羟基-3-硝基苯甲腈 | 3272-08-0

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 烃类硝化物
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 4-羟基-3-硝基苯甲腈
• 中文别名: 3-硝基-4-羟基苯甲腈；4-羟基-3-硝基苯甲肼；2-硝-4-氰基苯酚
• 英文名称: 4-hydroxy-3-nitrobenzonitrile
• 英文别名: 3-nitro-4-hydroxybenzonitrile；4-cyano-2-nitrophenol
• CAS: 3272-08-0
• 化学式: C₇H₄N₂O₃
• mdl: MFCD00070775
• 分子量: 164.12
• InChiKey: INBLGVOPOSGVTA-UHFFFAOYSA-N

物化性质

• 熔点：
  146-148 °C (lit.)
• 沸点：
  291.56°C (rough estimate)
• 密度：
  1.5018 (rough estimate)
• 稳定性/保质期：
  避免与不相容的材料或铁锈接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 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：
  89.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36/37/39,S37/39
• 危险类别码：
  R20/21/22,R36/37/38
• WGK Germany：
  3
• 海关编码：
  2926909090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302+H312+H332,H315,H319,H335
• 储存条件：
  密封存储于阴凉、干燥的仓库中。

SDS

Name:	4-Hydroxy-3-nitrobenzonitrile 97% Material Safety Data Sheet
Synonym:	4-Cyano-2-nitropheno
CAS:	3272-08-0

Section 1 - Chemical Product MSDS Name:4-Hydroxy-3-nitrobenzonitrile 97% Material Safety Data Sheet
Synonym:4-Cyano-2-nitropheno

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
3272-08-0	4-Hydroxy-3-nitrobenzonitrile	97%	221-899-8

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.
Skin:
Causes skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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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.
Ingestion:
Get medical aid. Wash mouth out with 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:
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.
Extinguishing Media:
In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant 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.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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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# 3272-08-0: Personal Protective Equipment Eyes: Not available.
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: Crystalline powder
Color: yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 146 - 148 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C7H4N2O3
Molecular Weight: 164.12

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents, acids, acetic anhydride, acid chlorides, carbon dioxide.
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# 3272-08-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Hydroxy-3-nitrobenzonitrile - 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
No information available.
IMO
No information available.
RID/ADR
No information available.

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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 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 37/39 Wear suitable gloves and eye/face
protection.
WGK (Water Danger/Protection)
CAS# 3272-08-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 3272-08-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 3272-08-0 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-羟基-3-硝基苯甲腈 在 盐酸 、 sodium hydride 、 sodium carbonate 、 potassium carbonate 、 三乙胺 、 tin(ll) chloride 作用下， 以 乙醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 Ethyl 4-[6-(4,5-dihydro-1,3-thiazol-2-yl)-3-oxo-1,4-benzoxazin-4-yl]butanoate
  参考文献：
  名称：

  新的1，4-苯并恶嗪衍生物钾通道开放剂的合成及其血管舒张活性。

  摘要：

  作为寻找新的钾通道开放剂的一部分，描述了衍生自克罗马卡林的苯并吡喃骨架的新的1,4-苯并恶嗪衍生物的合成和血管舒张活性。几种新的1,4-苯并恶嗪衍生物具有明显的血管舒张活性，其总体药理行为类似于CRK（1f，1i，2d，2e，2f和2i）。

  DOI：

  10.1016/s0968-0896(02)00091-3
• 作为产物：
  描述：

  双(4-氰苯基)醚 在 硝酸 作用下， 生成 4-羟基-3-硝基苯甲腈
  参考文献：
  名称：

  138.寻找化学am。部X.替补4：4'-脒基α ω -diphenoxyalkanes和二苯基醚类

  摘要：

  DOI：

  10.1039/jr9490000642

文献信息

• METHOD FOR PREPARING AFATINIB AND INTERMEDIATE THEREOF
  申请人：Xu Xuenong

  公开号：US20160083373A1

  公开（公告）日：2016-03-24

  Revealed in the present invention is a method for preparing Afatinib (I): using 2-nitrile-4-[4-(N,N-dimethylamino)-I-oxo-2-buten-I-yl]amino-5-[(S)-(tetrahydrofuran-3-yl)oxy]aniline (II) and 4-fluoro-3-chloroaniline (III) as starting materials, and respectively performing a condensation and cyclization reaction with N,N-dimethylformamide dimethyl acetal (IV) to prepare Afatinib (I), wherein the method significantly reduces the manufacturing steps of Afatinib and greatly lower the costs. In addition, also provided in the present invention is a method for preparing an intermediate of Afatinib, wherein the method has a stable process, uses readily available starting materials, has a low cost, and all the reactions are classic reactions, suitable for meeting amplification requirements in the industry.

  本发明揭示了一种制备阿法替尼（I）的方法：使用2-腈基-4-[4-(N,N-二甲基氨基)-1-氧代-2-丁烯-1-基]氨基-5-[(S)-(四氢呋喃-3-基)氧基]苯胺（II）和4-氟-3-氯苯胺（III）作为起始原料，分别与N,N-二甲基甲酰胺二甲基缩醛（IV）进行缩合和环化反应制备阿法替尼（I），该方法显著减少了阿法替尼的制造步骤，大大降低了成本。此外，本发明还提供了一种制备阿法替尼中间体的方法，该方法具有稳定的工艺过程，使用易得的起始原料，成本低廉，并且所有反应均为经典反应，适合满足行业中的扩产需求。
• Chemoselective Schmidt Reaction Mediated by Triflic Acid: Selective Synthesis of Nitriles from Aldehydes
  作者：Balaji V. Rokade、Kandikere Ramaiah Prabhu

  DOI：10.1021/jo3008258

  日期：2012.6.15

  An excellent utility of Schmidt reaction of aldehydes to access corresponding nitriles in an instantaneous reaction is demonstrated. The reaction of aldehydes with NaN3 and TfOH furnishes the corresponding nitriles in near quantitative yields and tolerates a variety of electron-withdrawing and electron-donating substituents on the substrates. Formanilides, a common side product in Schmidt reaction

  已证明醛的Schmidt反应在瞬时反应中能很好地利用相应的腈。醛与NaN 3和TfOH的反应以接近定量的产率提供了相应的腈，并且可以承受底物上的各种吸电子和供电子取代基。在施密特反应中常见的副产物甲虫胺未在该反应中观察到。除了这些优点之外，该反应的显着特征是它显示出显着的化学选择性，因为在反应条件下对酸和酮的官能度具有很好的耐受性。该反应易于扩展，高收率并且几乎是瞬时的。
• FUROISOQUINOLINE DERIVATIVE AND USE THEREOF
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1541576A1

  公开（公告）日：2005-06-15

  The present invention provides a compound represented by the formula    wherein A represents (1) a bond, (2) a group represented by the formula -CRa=CRb- (Ra and Rb each represent a hydrogen atom or C1-6 alkyl) and the like; R1 represents (1) cyano or (2) an optionally esterified or amidated carboxyl group; R2 represents (1) a hydrogen atom, (2) an optionally substituted hydroxy group, (3) an optionally substituted amino group and the like; R3 and R4 each represent a hydrogen atom and the like; R5 represents a hydrogen atom and the like; R6 represents an optionally substituted hydroxy group and the like; R7and R8 each represent an optionally substituted hydrocarbon group and the like; R9 and R10 each represent (1) a hydrogen atom and the like; Y represents an optionally substituted methylene group; and n represents 0 or 1, or a salt thereof, which has an excellent phosphodiesterase IV inhibiting action.

  本发明提供了一种化合物，其表示为式中的化合物，其中A代表（1）键，（2）由式 -CRa=CRb-（Ra和Rb分别代表氢原子或C1-6烷基等）表示的基团等；R1代表（1）氰基或（2）可选择酯化或酰胺化的羧基；R2代表（1）氢原子，（2）可选择取代的羟基，（3）可选择取代的氨基等；R3和R4各自代表氢原子等；R5代表氢原子等；R6代表可选择取代的羟基等；R7和R8各自代表可选择取代的碳氢基团等；R9和R10各自代表（1）氢原子等；Y代表可选择取代的亚甲基基团；n代表0或1，或其盐，具有优异的磷酸二酯酶IV抑制作用。
• Alpha2C adrenoreceptor agonists
  申请人：McCormick D. Kevin

  公开号：US20070093477A1

  公开（公告）日：2007-04-26

  In its many embodiments, the present invention relates to a novel class of phenylmorpholine and phenylthiomorpholine compounds useful as α2C adrenergic receptor agonists, pharmaceutical compositions containing the compounds, and methods of treatment, prevention, inhibition, or amelioration of one or more diseases associated with the α2C adrenergic receptor agonists using such compounds or pharmaceutical compositions.

  在其多种实施形式中，本发明涉及一类新型的苯基吗啡啶和苯基硫代吗啡啶化合物，这些化合物可用作α2C肾上腺素受体激动剂，包含这些化合物的药物组合物，以及使用这些化合物或药物组合物治疗、预防、抑制或改善与α2C肾上腺素受体激动剂相关的一种或多种疾病的方法。
• Palladium-catalyzed C–O bond formation: direct synthesis of phenols and aryl/alkyl ethers from activated aryl halides
  作者：Guoshu Chen、Albert S.C. Chan、Fuk Yee Kwong

  DOI：10.1016/j.tetlet.2006.11.036

  日期：2007.1

  palladium-catalyzed carbon–oxygen bond formation is reported. The palladium-tri-tert-butylphosphine complex was found to be effective in converting haloarenes to corresponding substituted phenols. This methodology offers a direct transformation of aryl halides to phenols, as well as the straightforward application to generate a wide variety of diaryl or alkyl/aryl ethers.

  据报道，形成了一种简单有效的钯催化的碳氧键。钯-三-叔丁基膦配合物被发现是有效的卤代芳烃转化成相应的取代的酚。这种方法可以将芳基卤化物直接转化为苯酚，并且可以直接用于生成各种二芳基或烷基/芳基醚。

表征谱图