4-(异丙氨基)-3-硝基苯甲腈 | 355022-17-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 4-(异丙氨基)-3-硝基苯甲腈
• 英文名称: 4-(isopropylamino)-3-nitrobenzonitrile
• 英文别名: 3-nitro-4-(propan-2-ylamino)benzonitrile
• CAS: 355022-17-2
• 化学式: C₁₀H₁₁N₃O₂
• mdl: MFCD01570606
• 分子量: 205.216
• InChiKey: UMTOOOMUGFVLDX-UHFFFAOYSA-N

物化性质

• 沸点：
  347.4±37.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  81.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 安全说明：
  S36/37
• 危险品标志：
  Xn
• 危险类别码：
  R20/21/22
• 海关编码：
  2926909090
• 危险性防范说明：
  P280
• 危险性描述：
  H302,H312,H332
• 储存条件：
  -20°C

SDS

Name:	4-(Isopropylamino)-3-nitrobenzonitrile 97% Material Safety Data Sheet
Synonym:
CAS:	355022-17-2

Section 1 - Chemical Product MSDS Name:4-(Isopropylamino)-3-nitrobenzonitrile 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
355022-17-2	4-(Isopropylamino)-3-nitrobenzonitrile	97%	unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. Harmful if absorbed through the skin.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Harmful if inhaled. May cause respiratory tract irritation.
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:

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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:
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:
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:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 355022-17-2: 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: Solid
Color: yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 113 - 115 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: C10H11N3O2
Molecular Weight: 205.22

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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.
Hazardous Decomposition Products:
Hydrogen cyanide, nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 355022-17-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-(Isopropylamino)-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
Shipping Name: NITRILES, SOLID, TOXIC, N.O.S.*
Hazard Class: 6.1
UN Number: 3276
Packing Group: III
IMO
Shipping Name: NITRILES, TOXIC, N.O.S.
Hazard Class: 6.1
UN Number: 3276
Packing Group: III
RID/ADR
Shipping Name: NITRILES, TOXIC, N.O.S.
Hazard Class: 6.1
UN Number: 3276
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
Safety Phrases:
S 36/37 Wear suitable protective clothing and
gloves.
WGK (Water Danger/Protection)
CAS# 355022-17-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 355022-17-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 355022-17-2 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-(异丙氨基)-3-硝基苯甲腈 在 palladium on activated charcoal 氢气 、 溶剂黄146 、 sodium nitrite 作用下， 以 乙酸乙酯 为溶剂， 反应 20.0h， 生成 1-异丙基-1H-苯并[d][1,2,3]噻唑-5-甲腈
  参考文献：
  名称：

  1-Alkyl-benzotriazole-5-carboxylic Acids Are Highly Selective Agonists of the Human Orphan G-Protein-Coupled Receptor GPR109b

  摘要：

  I-Substituted benzotriazole carboxylic acids have been identified as the first reported examples of selective small-molecule agonists of the human orphan G-protein-coupled receptor GPR109b (HM74), a low-affinity receptor for the HDL-raising drug niacin. No activity was observed at the highly homologous high-affinity macin receptor GPR109a (HM74A). The high degree of selectivity was attributed to a difference in the amino acid sequence adjacent to a key arginine-ligand interaction allowing somewhat larger ligands to be tolerated by GPR109b.

  DOI：

  10.1021/jm051099t
• 作为产物：
  描述：

  4-氟-3-硝基苯甲腈 、 异丙胺 以 乙醇 为溶剂， 反应 24.0h， 以82%的产率得到4-(异丙氨基)-3-硝基苯甲腈
  参考文献：
  名称：

  用于特异性识别 DNA 小沟中 G⋅C 碱基对的小序列敏感化合物。

  摘要：

  一系列新型小尺寸二脒与噻吩和修饰的 N-烷基苯并咪唑 σ 孔模块代表与单个 G·C 碱基对 (bp) DNA 序列的特异性结合。N-烷基或芳香环的变化对DNA小沟的微观结构敏感。合成了十三种新化合物来测试它们的结合亲和力和选择性。合成目标二脒所需的二氰基苯并咪唑是通过不同醛与不同3-氨基-4-（烷基-或苯基-氨基）苯甲腈的缩合/环化反应制备的。最终的二脒使用双三甲基甲硅烷基氨基锂(LiN[Si(CH 3 ) 3 ] 2 )或Pinner方法合成。通过生物传感器-SPR、荧光光谱、DNA热熔解、ESI-MS光谱、圆二色性和分子动力学等多种生物物理方法研究，与相似序列AAATTT和AAAGCTTT相比，新合成的化合物对AAAGTTT表现出很强的结合力和选择性。荧光光谱测定的结合亲和力结果与生物传感器-SPR获得的结果一致。这些小尺寸单 G·C bp 高度特异性结合物扩展了未来生物应用的化合物数据库。

  DOI：

  10.1002/chem.201904396

文献信息

• 一类含氧五元杂环化合物、合成方法、药物组 合物及用途
  申请人：江南大学

  公开号：CN111848599B

  公开（公告）日：2022-04-12

  本发明公开了一类含氧五元杂环化合物、合成方法、药物组合物及用途，属于医药及其制备和应用的技术领域。本发明含氧五元杂环具有抑制蛋白酪氨酸磷酸酶SHP2的生物活性，可以作为工具化合物研究蛋白酪氨酸磷酸酶SHP2在细胞信号转导过程中的生物学功能关联性，为预防和治疗癌症、代谢与免疫疾病提供新的手段。
• Synthesis and Potent Antimicrobial Activity of Some Novel N-(Alkyl)-2-Phenyl-1H-Benzimidazole-5-Carboxamidines
  作者：Hakan Göker、Mehmet Alp、Sulhiye Yıldız

  DOI：10.3390/10111377

  日期：——

  A series of 22 novel 1,2-disubstituted-1H-benzimidazole-N-alkylated-5- carboxamidine derivatives were synthesized and evaluated for in vitro antibacterial activity against S. aureus and methicillin resistant S. aureus (MRSA), E. coli, E. faecalis and for antifungal activity against C. albicans. Compound 59 [1-(2,4-dichlorobenzyl)-N- (2-diethylaminoethyl)-1H-benzimidazole-5-carboxamidine], with a 3

  合成了一系列 22 种新型 1,2-二取代-1H-苯并咪唑-N-烷基化-5-甲脒衍生物，并评估其对金黄色葡萄球菌和耐甲氧西林金黄色葡萄球菌 (MRSA)、大肠杆菌、 E. faecalis 和针对白色念珠菌的抗真菌活性。化合物 59 [1-(2,4-二氯苄基)-N-(2-二乙氨基乙基)-1H-苯并咪唑-5-甲脒]，在 C-2 位具有 3,4-二氯苯基，显示出最大的活性（ MIC = 3.12 microg/mL 对抗某些细菌和真菌白色念珠菌）。
• 3-Nitro-4-amino benzoic acids and 6-amino nicotinic acids are highly selective agonists of GPR109b
  作者：Philip J. Skinner、Martin C. Cherrier、Peter J. Webb、Carleton R. Sage、Huong T. Dang、Cameron C. Pride、Ruoping Chen、Susan Y. Tamura、Jeremy G. Richman、Daniel T. Connolly、Graeme Semple

  DOI：10.1016/j.bmcl.2007.09.058

  日期：2007.12

  A series of 3-nitro-4-substituted-aminobenzoic acids were prepared and found to act as potent and highly selective agonists of the orphan human GPCR GPR109b, a low affinity receptor for niacin. No activity was observed at the closely homologous high affinity niacin receptor, GPR109a. A second series, comprising 6-amino-substituted nicotinic acids was, also prepared and several analogues showed comparable activity to the nitroaryl series. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis of some new 2-substituted-phenyl-1H-benzimidazole-5-carbonitriles and their potent activity against candida species
  作者：Hakan Göker、Canan Kuş、David W. Boykin、Sulhiye Yildiz、Nurten Altanlar

  DOI：10.1016/s0968-0896(02)00103-7

  日期：2002.8

  New 2-substituted-phenyl-1H-benzimidazole-5-carboxylic acids (35, 38), ethyl-5-carboxylate (36), -5-carboxamides (37, 39),-5-carboxaldeliyde (42), -5-chloro (40), -5-trifluoromethyl (41), and -5-carbonitriles (44-53, 55-67), -6-carbonitrilc (54) were prepared and evaluated in vitro against Candida species. The cyano substituted compounds 53, 57, 58 and 61 exhibited the greatest activity with MIC values of 3.12 mug/mL, values similar to that of fluconazole. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis and Antimicrobial Activity of Some New 2-Phenyl-N-substituted Carboxamido-1H-benzimidazole Derivatives
  作者：Hakan Göker、Meral Tunçbilek、Sibel Süzen、Canan Kus、Nurten Altanlar

  DOI：10.1002/1521-4184(200105)334:5<148::aid-ardp148>3.0.co;2-s

  日期：2001.5

  Some 1H-benzimidazole-carboxamide derivatives were prepared and their antimicrobial activities against Staphyloccus aureus, Escherichia coli and Candida albicans evaluated. Compounds 18, 22, and 25 exhibited the best activity against Candida albicans.