2-(甲硫基)乙酰胺 | 22551-24-2

• 物质功能分类: 有机原料 - 氨基化合物 - 酰胺类化合物
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-(甲硫基)乙酰胺
• 中文别名: 甲硫基乙酰胺；2-(甲基硫代)乙酰胺
• 英文名称: 2-(methylthio)acetamide
• 英文别名: α-(methylthio)acetamide；2-methylsulfanylacetamide
• CAS: 22551-24-2
• 化学式: C₃H₇NOS
• mdl: MFCD00041321
• 分子量: 105.161
• InChiKey: OBENGAMZEGRSIC-UHFFFAOYSA-N

物化性质

• 熔点：
  99-102℃
• 沸点：
  259℃
• 密度：
  1.132
• 闪点：
  110℃
• 溶解度：
  溶于甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2930909090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335
• 储存条件：
  存放于惰性气体中，并避免接触湿气（否则可能分解）。

SDS

2-(Methylthio)acetamide
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: 2-(Methylthio)acetamide

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
HEALTH HAZARDS
Skin corrosion/irritation Category 2
Category 2A
Serious eye damage/eye irritation
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols
Signal word Warning
Hazard statements Causes skin irritation
Causes serious eye irritation
Precautionary statements:
Wash hands thoroughly after handling.
[Prevention]
Wear protective gloves/eye protection/face protection.
IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses,
[Response]
if present and easy to do. Continue rinsing.
If eye irritation persists: Get medical advice/attention.
IF ON SKIN: Gently wash with plenty of soap and water.
If skin irritation occurs: Get medical advice/attention.
Take off contaminated clothing and wash before reuse.

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: 2-(Methylthio)acetamide
Percent: >98.0%(GC)
CAS Number: 22551-24-2
Chemical Formula: C3H7NOS

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
2-(Methylthio)acetamide

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Section 4. FIRST AID MEASURES
Skin contact: Remove/Take off immediately all contaminated clothing. Gently wash with plenty of
soap and water. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Specific hazards arising Take care as it may decompose upon combustion or in high temperatures to
from the chemical: generate poisonous fume.
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Technical measures: Handling is performed in a well ventilated place. Wear suitable protective equipment.
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Storage conditions: Keep container tightly closed. Store in a cool and dark place.
Store under inert gas.
Protect from moisture.
Store away from incompatible materials such as oxidizing agents.
Moisture-sensitive
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Install a closed system or local exhaust as possible so that workers should not be
Engineering controls:
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Protective gloves.
Hand protection:
Eye protection: Safety glasses. A face-shield, if the situation requires.
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Physical state (20°C): Solid
2-(Methylthio)acetamide

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Form: Crystal- Powder
Colour: White - Almost white
Odour: No data available
pH: No data available
Melting point/freezing point:104°C
Boiling point/range: No data available
Flash point: No data available
Flammability or explosive
limits:
Lower: No data available
Upper: No data available
Relative density: No data available
Solubility(ies):
[Water] No data available
[Other solvents]
Soluble: Methanol

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Section 10. STABILITY AND REACTIVITY
Stable under proper conditions.
Chemical stability:
Possibility of hazardous No special reactivity has been reported.
reactions:
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide, Nitrogen oxides (NOx), Sulfur oxides
products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
NTP = No data available
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
No data available
Crustacea:
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobility in soil
No data available
Log Pow:
Soil adsorption (Koc): No data available
No data available
Henry's Law
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.
2-(Methylthio)acetamide

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Section 14. TRANSPORT INFORMATION
Hazards Class: Does not correspond to the classification standard of the United Nations
UN-No: Not listed

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2-(甲硫基)乙酰胺 在 高氯酸 、 一氧化二氮 作用下， 生成 acetamide radical
  参考文献：
  名称：

  与氢原子的双分子均裂取代 (SH2) 反应。α-（甲硫基）乙酰胺脉冲辐射分解中的时间分辨电子自旋共振检测

  摘要：

  α-(甲硫基) 乙酰胺水溶液的脉冲辐解产生出乎意料的大量乙酰胺自由基，这些自由基由时间分辨电子自旋共振 (TRESR) 光谱法确定。TRESR 测量的自由基产率的 pH 依赖性、选择性清除反应的结果和反应热化学的密度泛函理论预测证明乙酰胺自由基片段被 H 原子的双分子均裂取代 S(H)2 是最多的可能的形成途径。

  DOI：

  10.1021/ja0458625
• 作为产物：
  描述：

  (methylthio)acetyl chloride 在 氨 作用下， 以 苯 为溶剂， 反应 0.08h， 生成 2-(甲硫基)乙酰胺
  参考文献：
  名称：

  Mori, Yuji; Fujiwara, Shigeru; Miyachi, Toshiko, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 5, p. 1505 - 1517

  摘要：

  DOI：

文献信息

• Enzymatic nitrile hydrolysis catalyzed by nitrilase ZmNIT2 from maize. An unprecedented β-hydroxy functionality enhanced amide formation
  作者：Chandrani Mukherjee、Dunming Zhu、Edward R. Biehl、Rajiv R. Parmar、Ling Hua

  DOI：10.1016/j.tet.2006.04.069

  日期：2006.6

  To explore the synthetic potential of nitrilase ZmNIT2 from maize, the substrate specificity of this nitrilase was studied with a diverse collection of nitriles. The nitrilase ZmNIT2 showed high activity for all the tested nitriles except benzonitrile, producing both acids and amides. For the hydrolysis of aliphatic, aromatic nitriles, phenylacetonitrile derivatives and dinitriles, carboxylic acids

  为了探索玉米中腈水解酶ZmNIT2的合成潜力，研究了该腈水解酶的底物特异性，并收集了多种腈。腈水解酶ZmNIT2对除苄腈以外的所有测试腈均显示高活性，同时生成酸和酰胺。对于脂族，芳族腈，苯乙腈衍生物和二腈的水解，羧酸是主要产物。出乎意料的是，发现酰胺是腈水解酶ZmNIT2催化的β-羟基腈水解的主要产物。酶-底物复杂中间体中羟基和氮之间的氢键不利于氨的损失和酰基-酶中间体的形成，后者进一步水解为酸，
• Development and a Practical Synthesis of Nepafenac Intermediate via Modified Gassman Reaction
  作者：Marcin Cybulski、Adam Formela、Mariola Mucha、Karolina Klos、Jacek Roszczynski、Jerzy Winiarski

  DOI：10.2174/157017812802139582

  日期：2012.7.1

  Modification of nepafenac intermediate synthesis (5A) via Gassman specific ortho-substitution is reported. According to the process, 2-aminobenzophenone (1A) and 2-(methylthio)acetamide (2) were reacted in the convenient temperature conditions, in the presence of N-chlorophthalimide (3) or 1,3-dichloro-5,5-dimethylhydantoin (4), to activate the formation of azasulfonium salt and rearrangement thereof

  据报道，通过Gassman特异性邻位取代修饰了尼泊芬尼中间体合成（5A）。根据该方法，在便利的温度条件下，在N-氯邻苯二甲酰亚胺（3）或1,3-二氯-5,5-存在下，使2-氨基二苯甲酮（1A）和2-（甲硫基）乙酰胺（2）反应。二甲基乙内酰脲（4），以激活氮杂ulf盐的形成并将其重排为纯的2-氨基-3-苯甲酰基-α-（甲硫基）苯基乙酰胺（5A）。该方法似乎适合于大规模进行的反应。
• Method of producing an inhibitory effect on blood platelet aggregation
  申请人：A. H. Robins Company, Inc.

  公开号：US04313949A1

  公开（公告）日：1982-02-02

  Novel 2-amino-3-benzoyl-phenylacetamides are provided having the formula: ##STR1## wherein R represents hydrogen or lower alkyl, R.sup.1 and R.sup.2 represent hydrogen, lower alkyl, cycloalkyl, phenyl and phenyl substituted by lower alkyl, lower alkoxy, halogen, nitro and trifluoromethyl, and R.sup.1 and R.sup.2 when taken together with the adjacent nitrogen may form a heterocyclic residue; X represents hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl; Y represents hydrogen, lower alkyl, lower alkoxy, halogen, trifluoromethyl, lower alkylthio, lower alkyloxythio or lower alkyldioxythio; Am is primary amino (--NH.sub.2), methylamino or dimethylamino, and n is 1 to 3 inclusive. The compounds exhibit anti-inflammatory, antipyretic, anti-blood platelet aggregation and analgetic pharmacological activities.

  提供了具有以下结构式的新型2-氨基-3-苯甲酰基-苯乙酰胺：其中R代表氢或较低的烷基，R.sup.1和R.sup.2代表氢，较低的烷基，环烷基，苯基和被较低烷基，较低烷氧基，卤素，硝基和三氟甲基取代的苯基，当R.sup.1和R.sup.2与相邻的氮一起形成杂环残基时；X代表氢，较低的烷基，较低的烷氧基，卤素或三氟甲基；Y代表氢，较低的烷基，较低的烷氧基，卤素，三氟甲基，较低的烷基硫，较低的烷氧基硫或较低的烷基二氧基硫；Am是初级氨基（--NH.sub.2），甲基氨基或二甲基氨基，n为1至3（含）。这些化合物具有抗炎、退热、抗血小板聚集和镇痛药理活性。
• 一种奈帕芬胺的制备方法
  申请人：广州仁恒医药科技股份有限公司

  公开号：CN106928103A

  公开（公告）日：2017-07-07

  本发明公开一种奈帕芬胺的制备方法，包括如下步骤：步骤一：合成2‑(甲硫基)乙酰胺；步骤二：合成α‑甲硫基‑(2‑氨基‑3‑苯甲酰基)苯乙酰胺；步骤三：合成奈帕芬胺。与现有技术相比，本发明的奈帕芬胺的制备方法，原材料容易购买，副反应过度氯化杂质容易纯化、升高反应温度能耗较小、终产品不需ODS反相快速层析。
• N-Chlorophthalimide as a mild and efficient chlorination reagent in the Gassman ortho alkylation of aromatic amines. Synthesis of 3-(methylthio)oxindoles
  作者：Marcin Cybulski、Adam Formela、Izabela Fokt

  DOI：10.1016/j.tetlet.2014.08.044

  日期：2014.10

  Gassman 3-(methylthio)oxindole synthesis is reported. In our method, substituted anilines and 2-(methylthio)acetamide were reacted under mild reaction conditions, in the presence of N-chlorophthalimide as a chlorinating agent to give α-amidosulfides, which, in the next step of the process, were cyclized to give 3-(methylthio)oxindoles. The method was successfully applied for the synthesis of the key intermediate

  据报道，对Gassman 3-（甲硫基）恶唑合成有实际的改进。在我们的方法中，将取代的苯胺与2-（甲硫基）乙酰胺在温和的反应条件下，在作为氯化剂的N-氯邻苯二甲酰亚胺存在下反应，生成α-酰胺基硫化物，然后将其环化为得到3-（甲硫基）氧吲哚。该方法已成功地用于关键中间体2-（2-氨基-3-苯甲酰基苯基）-2-（甲硫基）乙酰胺的合成，在制备常用的眼科药物奈帕芬酸的过程中。