3-氟-4-甲基乙酰苯胺 | 7149-79-3

• 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: 3-氟-4-甲基乙酰苯胺
• 中文别名: 3-氯-4-甲基乙酰苯胺；N-乙酰基-3-氯-4-甲基苯胺
• 英文名称: N-(3-chloro-4-methylphenyl)acetamide
• 英文别名: 3-chloro-4-methylacetanilide；N-acetyl-3-chloro-p-toluidine；4-acetamido-2-chlorotoluene
• CAS: 7149-79-3
• 化学式: C₉H₁₀ClNO
• mdl: MFCD00032582
• 分子量: 183.637
• InChiKey: IGLVCWPPISIXPR-UHFFFAOYSA-N

物化性质

• 熔点：
  105-107°C
• 沸点：
  80°C (rough estimate)
• 密度：
  1.218
• 保留指数：
  1640
• 稳定性/保质期：
  遵照规格使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• TSCA：
  Yes
• 危险类别码：
  R25
• RTECS号：
  AN3325000
• 包装等级：
  III
• 危险品运输编号：
  UN 2811
• 储存条件：
  密封于阴凉干燥处。

SDS

Name:	N1-(3-chloro-4-methylphenyl)acetamide 97% Material Safety Data Sheet
Synonym:	3-Chloro-4-methylacetanilide3'-Chloro-p-acetotolouid
CAS:	7149-79-3

Section 1 - Chemical Product MSDS Name:N1-(3-chloro-4-methylphenyl)acetamide 97% Material Safety Data Sheet
Synonym:3-Chloro-4-methylacetanilide3'-Chloro-p-acetotolouid

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
7149-79-3	N1-(3-Chloro-4-methylphenyl)acetamide	97%	230-483-5

Hazard Symbols: XN
Risk Phrases: 22 36/37/38

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful if swallowed. 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:
Harmful if swallowed. May cause irritation of the digestive tract.
Inhalation:
Causes respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

---

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.

---

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.

---

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.

---

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.

---

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# 7149-79-3: 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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 105 - 107 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: C9H10ClNO
Molecular Weight: 184

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Acids, bases, oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, chlorine, nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 7149-79-3: AN3325000 LD50/LC50:
Not available.
Carcinogenicity:
N1-(3-Chloro-4-methylphenyl)acetamide - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

---

Section 12 - ECOLOGICAL INFORMATION

---

Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

---

Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 22 Harmful if swallowed.
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# 7149-79-3: No information available.
Canada
CAS# 7149-79-3 is listed on Canada's NDSL List.
CAS# 7149-79-3 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 7149-79-3 is listed on the TSCA inventory.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

类别：农药
毒性分级：剧毒
急性毒性（口服-野鸟）：LD50 为 1.3 毫克/公斤
可燃性危险特性：热分解时排出有毒氮氧化物和氯化物烟雾
储运特性：库房低温、通风干燥保存
灭火剂：水、二氧化碳、泡沫、干粉

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
  4-甲基乙酰苯胺	4-Methylacetanilide	103-89-9	C9H11NO	149.192
  3-氯-4-甲基苯胺	3-chloro-p-toluidine	95-74-9	C7H8ClN	141.6

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	2,5-Dichlor-4-acetamido-toluol	——	C9H9Cl2NO	218.083
  4-乙酰氨基-2-氯苯甲酸	4-Acetylamino-2-chlorobenzoic acid	38667-55-9	C9H8ClNO3	213.62
  N-乙酰基-2-溴-5-氯-4-甲基苯胺	N-(2-bromo-5-chloro-4-methylphenyl)acetamide	116010-06-1	C9H9BrClNO	262.534

反应信息

• 作为反应物：
  描述：

  3-氟-4-甲基乙酰苯胺 在 盐酸 、 叔丁基过氧化氢 、 N-氯代丁二酰亚胺 、 N-溴代丁二酰亚胺(NBS) 、 三氟化硼乙醚 、 三乙胺 、 potassium hydroxide 、 sodium hydroxide 、 zinc(II) iodide 、 过氧化苯甲酰 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 81.0h， 生成 普卡必利
  参考文献：
  名称：

  一种普卡必利的制备方法

  摘要：

  本发明提供了一种普卡必利的新制备方法，所述方法以3‑氯‑4‑甲基苯胺为起始原料，经氨基保护，亲核取代，羟基保护，芳烃氯代，自由基溴代，水解，分子内付克烷基化反应关环，氨基脱保护，氧化酰胺化合成普卡必利。本方案无危险工艺，未采用剧毒试剂，安全绿色环保，反应产生的副产物少，收率得以提高。

  公开号：

  CN109232544B
• 作为产物：
  描述：

  4-甲基乙酰苯胺 在 氢氟酸 、 五氟化锑 、 sodium chloride 作用下， 反应 2.0h， 以78%的产率得到3-氟-4-甲基乙酰苯胺
  参考文献：
  名称：

  含氮（杂）芳烃与超强酸的互补位点选择性卤化。

  摘要：

  与经典的芳香族取代反应互补的芳烃的位点选择性官能化仍然是有机合成中的长期追求。通过利用氧化过程中的ion离子的产生和HF / SbF 5中含氮功能的质子化，芳香胺的经典惰性Csp 2 -H键发生氯化和碘化。此外，分子的超强酸促进（聚）质子化作用起到保护作用，有利于天然生物碱和活性药物成分的后期选择性卤化

  DOI：

  10.1002/chem.202000902

文献信息

• Synthetic Applications of Pd(II)-Catalyzed C−H Carboxylation and Mechanistic Insights: Expedient Routes to Anthranilic Acids, Oxazolinones, and Quinazolinones
  作者：Ramesh Giri、Jonathan K. Lam、Jin-Quan Yu

  DOI：10.1021/ja9077705

  日期：2010.1.20

  carbon monoxide is discussed. Identification of two key intermediates, a mixed anhydride and benzoxazinone formed by reductive elimination from organometallic Ar(CO)Pd(II)-OTs species, provides mechanistic evidence for a dual-reaction pathway.

  已经开发了一种 Pd(II) 催化的反应方案，用于将苯胺中的邻位 CH 键羧化以形成 N-酰基邻氨基苯甲酸。该反应过程为从简单的苯胺快速组装具有生物学和药学意义的分子（例如苯并恶嗪酮和喹唑啉酮）提供了一种新颖且有效的策略，而无需安装和去除外部导向基团。反应条件也适用于 N-苯基吡咯烷酮的羧化。含有对甲苯磺酸盐作为阴离子配体的单体钯环已通过 X 射线晶体学表征，并讨论了对甲苯磺酸在一氧化碳存在下活化 CH 键中的关键作用。鉴定两个关键中间体，
• [EN] FLAVIN DERIVATIVES<br/>[FR] DÉRIVÉS DE LA FLAVINE
  申请人：BIORELIX PHARMACEUTICALS INC

  公开号：WO2010019208A1

  公开（公告）日：2010-02-18

  The present invention relates novel flavin derivatives and other flavin derivatives, their use and compositions for use as riboswitch ligands and/or anti-infectives. The invention also provides method of making novel flavin derivatives.

  本发明涉及新型黄素衍生物和其他黄素衍生物，它们的用途以及用作核糖开关配体和/或抗感染剂的组合物。该发明还提供了制备新型黄素衍生物的方法。
• Synthesis of Acetamides from Aryl Amines and Acetonitrile by Diazotization under Metal-Free Conditions
  作者：Yao-Fu Zeng、Yi-Na Li、Na-Na Zhang、Huan Kang、Pan Duan、Fang Xiao、Yu Guo、Xianghao Wen

  DOI：10.1055/s-0039-1690237

  日期：2019.12

  An efficient and metal-free coupling reaction has been developed that affords acetamides from the corresponding aryl amines and acetonitrile. This method tolerates a wide range of functional groups and is selective toward aryl amines. Preliminary mechanistic studies were conducted.

  已开发出一种有效且无金属的偶联反应，可从相应的芳胺和乙腈中生成乙酰胺。该方法可耐受范围广泛的官能团，并且对芳基胺具有选择性。进行了初步的机理研究。
• One-step reductive amidation of nitro arenes: application in the synthesis of Acetaminophen™
  作者：Apurba Bhattacharya、Vikram C. Purohit、Victor Suarez、Ritesh Tichkule、Gaurang Parmer、Frank Rinaldi

  DOI：10.1016/j.tetlet.2005.09.196

  日期：2006.3

  A novel thioacetate mediated one-step reductive acetamidation of aryl nitro compounds was developed and applied to an efficient synthesis of acetaminophen. The reaction also proceeds well without a solvent in the presence of a catalytic amount of surfactant.

  开发了一种新型的硫代乙酸酯介导的芳基硝基化合物一步还原乙酰胺化方法，并将其用于对乙酰氨基酚的有效合成。在催化量的表面活性剂的存在下，该反应在没有溶剂的情况下也能进行得很好。
• Complementary Site-Selective Sulfonylation of Aromatic Amines by Superacid Activation
  作者：Paul Bourbon、Emeline Appert、Agnès Martin-Mingot、Bastien Michelet、Sébastien Thibaudeau

  DOI：10.1021/acs.orglett.1c00994

  日期：2021.6.4

  superacidic conditions, aniline and indole derivatives are sulfonylated at low temperature with easy-to-access arenesulfonic acids or arenesulfonyl hydrazides. By modification of the functional-group directing effect through protonation, this method allows nonclassical site functionalization by overcoming the innate regioselectivity of electrophilic aromatic substitution. This superacid-mediated sulfonylation

  在超酸性条件下，苯胺和吲哚衍生物在低温下用易于获得的芳烃磺酸或芳烃磺酰肼进行磺酰化。通过质子化修饰官能团导向效应，该方法通过克服亲电芳香取代的先天区域选择性，允许非经典位点官能化。这种超强酸介导的芳烃磺酰化是对现有方法的补充，可以通过质子化保护应用于天然生物碱和活性药物成分的后期位点选择性功能化。