4-碘-3-甲基苯胺 | 4949-69-3

• 物质功能分类: 有机原料 - 氨基化合物 - 环烷胺、芳香单胺、芳香多胺及其衍生物和盐
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-碘-3-甲基苯胺
• 英文名称: 4-iodo-3-methylaniline
• 英文别名: 4-iodo-3-methyl-phenylamine；3-methyl-4-iodoaniline；2-iodo-5-aminotoluene；2-iodo 5-aminotoluene；4-iodo-3-methyl-aniline；4-Jod-3-methyl-anilin
• CAS: 4949-69-3
• 化学式: C₇H₈IN
• mdl: MFCD01569451
• 分子量: 233.052
• InChiKey: UISBOJCPTKUBIC-UHFFFAOYSA-N

物化性质

• 熔点：
  50-55 °C
• 沸点：
  273°C (rough estimate)
• 密度：
  1.7004 (estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 安全说明：
  S26,S37/39
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2921430090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Name:	4-Iodo-3-methylaniline 98% Material Safety Data Sheet
Synonym:
CAS:	4949-69-3

Section 1 - Chemical Product MSDS Name:4-Iodo-3-methylaniline 98% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
4949-69-3	4-Iodo-3-methylaniline	98%	unlisted

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.Light sensitive.
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.
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:
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. Avoid generating dusty conditions.

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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# 4949-69-3: 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: beige - brown - dark gray
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 49 - 51 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: Insoluble.
Specific Gravity/Density:
Molecular Formula: C7H8IN
Molecular Weight: 233.05

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Light.
Incompatibilities with Other Materials:
Not available.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide, hydrogen iodide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 4949-69-3 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Iodo-3-methylaniline - 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# 4949-69-3: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 4949-69-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 4949-69-3 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

制备方法与用途

4-碘-3-甲基苯胺可用作有机合成中间体和医药中间体，主要应用于实验室研发和化工生产过程。

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  2-碘-5-硝基甲苯	2-iodo-5-nitrotoluene	5326-38-5	C7H6INO2	263.035
  3-甲基苯胺	1-amino-3-methylbenzene	108-44-1	C7H9N	107.155

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	N-(4-iodo-3-methylphenyl)acetamide	97113-39-8	C9H10INO	275.089

反应信息

• 作为反应物：
  描述：

  4-碘-3-甲基苯胺 在 吡啶 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 N-(4-iodo-3-methylphenyl)-N,4-dimethylbenzenesulfonamide
  参考文献：
  名称：

  通过钯催化串联烷基化/直接芳基化反应制备环化吲哚的途径

  摘要：

  描述了降冰片烯介导的钯催化串联烷基化/CH 官能化序列，其中烷基-芳基键和杂芳基-芳基键在一锅中形成。以溴代烷基吲哚和芳基碘化物为原料，以良好的收率合成了多种高度取代的六元和七元环环化吲哚。

  DOI：

  10.1021/ja054472v
• 作为产物：
  描述：

  3-甲基苯胺 在 1,4-dibenzyl-1,4-diazoniabicyclo[2.2.2]octane dichloroiodate 作用下， 以 neat (no solvent) 为溶剂， 反应 0.25h， 以90%的产率得到4-碘-3-甲基苯胺
  参考文献：
  名称：

  Regioselective iodination of aryl amines using 1,4-dibenzyl-1,4-diazoniabicyclo [2.2.2] octane dichloroiodate in solution and under solvent-free conditions

  摘要：

  1,4-二苄基-1,4-二氮鎓二环[2.2.2]辛烷二氯碘酸盐是一种高效的区域选择性碘化试剂，适用于芳香胺的碘化反应。多种芳香胺与该试剂反应，均能区域选择性地生成碘化产物。该碘化反应可以在室温下于溶液中或无溶剂条件下进行。

  DOI：

  10.4314/bcse.v29i1.15

文献信息

• Acetamides and benzamides that are useful in treating sexual dysfunction
  申请人：——

  公开号：US20040029887A1

  公开（公告）日：2004-02-12

  The present invention relates to the use of compounds of formula (I) 1 for the treatment of sexual dysfunction and to compositions containing compounds of formula (I) for the treatment of sexual dysfunction.

  本发明涉及使用式(I)的化合物治疗性功能障碍，以及含有式(I)化合物的组合物用于治疗性功能障碍。
• Synthesis and Biological Evaluation of 4-Anilino-quinazolines and -quinolines as Inhibitors of Breast Cancer Resistance Protein (ABCG2)
  作者：Michael K. Krapf、Michael Wiese

  DOI：10.1021/acs.jmedchem.6b00330

  日期：2016.6.9

  of cancer often fails due to overexpression of the ATP-binding cassette (ABC) transport proteins, like ABCG2, triggering active efflux of various structurally unrelated drugs. This so-called multidrug resistance (MDR) may be reversed by selective, potent, and nontoxic inhibitors of ABCG2. As only a few potent inhibitors are known, new compounds based on a 4-substituted-2-phenylquinazoline scaffold

  癌症的化学疗法治疗通常会因ATP结合盒（ABC）转运蛋白（如ABCG2）的过表达而失败，从而触发各种结构上不相关的药物的主动流出。这种所谓的多药耐药性（MDR）可以通过ABCG2的选择性，有效和无毒抑制剂来逆转。因为仅已知几种有效的抑制剂，所以研究了基于4-取代的-2-苯基喹唑啉骨架的新化合物。用羟基，氰基，硝基，乙酰胺基和氟取代可导致对ABCG2的高度抑制活性。在MTT功效测定中证实了逆转最具活性的化合物的MDR的能力。此外，发现可忽略的低固有细胞毒性导致高治疗率。对于喹唑啉化合物，对ABCB1和ABCC1的抑制活性的研究产生了对ABCG2的高选择性。基于喹啉的类似物显示较低的抑制活性和选择性。该研究产生了各种有希望的化合物，其中一些具有比标准抑制剂Ko143更好的性能。
• [EN] URACIL OR THYMINE DERIVATIVE FOR TREATING HEPATITIS C<br/>[FR] DÉRIVÉ D'URACILE OU DE THYMINE POUR LE TRAITEMENT DE L'HÉPATITE C
  申请人：ABBOTT LAB

  公开号：WO2009039127A1

  公开（公告）日：2009-03-26

  Present application relates to the compounds of formula I useful to treat hepatitis C (HCV) infections. In the structure of the disclosed compounds is the uracil or thymine derivative linked via a phenylene into either fused 2-ring cyclic system (R6) or alternatively via additional two-atom linker (L) to a 5-6 membered monocycle (R6). Application further discloses polymorphs and pseudopolymorphs of two specific compounds: N-(6(3-t-butyl-5-(2>4-dioxo-3,4-dihydropyrimidin-1 (2H)- y!)2-methoxy-phenyl)naphthalen-2-yl)methanesulfonamide and (E)-N-(4(3-t- butyl-5-(2,4-dioxo-3)4-dihydropyrimidin-1 (2H)-yl)2-methoxy-styryl- phenyl)methanesulfonamide.

  本申请涉及一种用于治疗丙型肝炎（HCV）感染的化合物，其化学式为I。所述化合物的结构中，尿嘧啶或胸腺嘧啶衍生物通过苯基与融合的2环环系统（R6）或者通过额外的两原子连接物（L）与5-6环单环（R6）相连。该申请还揭示了两种特定化合物的多晶形和伪多晶形：N-(6(3-叔丁基-5-(2>4-二氧化-3,4-二氢嘧啶-1(2H)-基)2-甲氧基苯基)萘-2-基)甲磺酰胺和(E)-N-(4(3-叔丁基-5-(2,4-二氧化-3,4-二氢嘧啶-1(2H)-基)2-甲氧基-苯乙烯基苯基)甲磺酰胺。
• Regioselective iodination of aryl amines using 1,4-dibenzyl-1,4-diazoniabicyclo [2.2.2] octane dichloroiodate in solution and under solvent-free conditions
  作者：M. Alikarami、S. Nazarzadeh、M. Soleiman-Beigi

  DOI：10.4314/bcse.v29i1.15

  日期：——

  1,4-Dibenzyl-1,4-diazoniabicyclo[2.2.2]octane dichloroiodate is an efficient and regioselective reagent for iodination of aryl amines. A wide variety of aryl amines in reaction with this reagent afforded regioselectively iodinated products. The iodination reaction can be carried out in solution or under solvent-free condition at room temperature.

  1,4-二苄基-1,4-二氮鎓二环[2.2.2]辛烷二氯碘酸盐是一种高效的区域选择性碘化试剂，适用于芳香胺的碘化反应。多种芳香胺与该试剂反应，均能区域选择性地生成碘化产物。该碘化反应可以在室温下于溶液中或无溶剂条件下进行。
• <i>Ortho</i>CH Acylation of Aryl Iodides by Palladium/Norbornene Catalysis
  作者：Zhe Dong、Jianchun Wang、Zhi Ren、Guangbin Dong

  DOI：10.1002/anie.201506397

  日期：2015.10.19

  Reported herein is a palladium/norbornene‐catalyzed ortho‐arene acylation of aryl iodides by a Catellani‐type CH functionalization. This transformation is enabled by isopropyl carbonate anhydrides, which serve as both an acyl cation equivalent and a hydride source.

  本文报道的是钯/降冰片烯的催化邻由Catellani-C型的芳基碘化物的-arene酰化 ħ官能化。碳酸异丙酯酐可实现这种转化，它们既可作为酰基阳离子当量又可作为氢化物源。