N,N-(二硫-4,1-亚苯基)双乙酰胺 | 16766-09-9

• 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: N,N-(二硫-4,1-亚苯基)双乙酰胺
• 中文别名: N,N'-(二硫-4,1-亚苯基)双乙酰胺；N,N"-(二硫-4,1-亚苯基)双乙酰胺
• 英文名称: (4-acetamidophenyl)disulfide
• 英文别名: N,N'-(disulfanediylbis(4,1-phenylene))diacetamide；Acetamide, N,N'-(dithiodi-4,1-phenylene)bis-；N-[4-[(4-acetamidophenyl)disulfanyl]phenyl]acetamide
• CAS: 16766-09-9
• 化学式: C₁₆H₁₆N₂O₂S₂
• 分子量: 332.447
• InChiKey: XDZOVXPAGVIXBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2930909090

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 4-ACETAMIDOPHENYL DISULFIDE
CAS-No. : 16766-09-9
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Acute aquatic toxicity (Category 1)
Chronic aquatic toxicity (Category 1)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H410 Very toxic to aquatic life with long lasting effects.
Precautionary statement(s)
P273 Avoid release to the environment.
P501 Dispose of contents/ container to an approved waste disposal plant.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R50/53 Very toxic to aquatic organisms, may cause long-term adverse effects in
the aquatic environment.
S-phrase(s)
S60 This material and its container must be disposed of as hazardous waste.
S61 Avoid release to the environment. Refer to special instructions/ Safety
data sheets.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C16H16N2O2S2
Molecular Weight : 332,45 g/mol
Component Concentration
4-ACETAMIDOPHENYL DISULFIDE
CAS-No. 16766-09-9 -

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Section 4. FIRST AID MEASURES
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been thoroughly
investigated.
Indication of immediate medical attention and special treatment needed
no data available

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Section 5. FIRE-FIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx), Sulphur oxides
Precautions for fire-fighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the
environment must be avoided.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at
the end of workday.
Personal protective equipment
Eye/face protection
Use equipment for eye protection tested and approved under appropriate government standards
such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the
standard EN 374 derived from it.
Body Protection
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting/freezing point no data available
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- log Pow: 4,695
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
Potential health effects
Inhalation May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been thoroughly
investigated.
Additional Information
RTECS: Not available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
Very toxic to aquatic life with long lasting effects.

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
UN-Number
ADR/RID: 3077 IMDG: 3077 IATA: 3077
UN proper shipping name
ADR/RID: ENVIRONMENTALLY HAZARDOUS SUBSTANCE, SOLID, N.O.S. (4-ACETAMIDOPHENYL
DISULFIDE)
IMDG: ENVIRONMENTALLY HAZARDOUS SUBSTANCE, SOLID, N.O.S. (4-ACETAMIDOPHENYL
DISULFIDE)
IATA: Environmentally hazardous substance, solid, n.o.s. (4-ACETAMIDOPHENYL DISULFIDE)
Transport hazard class(es)
ADR/RID: 9 IMDG: 9 IATA: 9
Packaging group
ADR/RID: III IMDG: III IATA: III
Environmental hazards
ADR/RID: yes IMDG Marine pollutant: yes IATA: yes
Special precautions for users
Further information
EHS-Mark required (ADR 2.2.9.1.10, IMDG code 2.10.3) for single packagings and combination packagings
containing inner packagings with Dangerous Goods > 5L for liquids or > 5kg for solids.

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  N,N-(二硫-4,1-亚苯基)双乙酰胺 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 4.0h， 以77%的产率得到4-乙酰氨基苯硫酚
  参考文献：
  名称：

  13 C NMR光谱和从头算的对位取代硫酚和二硫化物的电子性质：与哈米特参数和原子电荷的关系

  摘要：

  大量的对位取代苯硫醇和相应的 二硫化物 被合成和表征 1 H NMR， 13 C NMR和红外光谱。全部十六个的几何硫醇 和十四 二硫化物在B3LYP / 6-31G（d）水平上对化合物进行了优化，而电子结构和13 C各向同性位移是通过从头算Hartree-Fock方法，不依赖于规规的原子轨道（GIAO）算法和6- 31 + G（d，p）基集。计算出的13 C NMR各向同性位移与实验数据表现出令人钦佩的一致性（δrmsd〜4.6 ppm）。对位取代碳的化学位移与Hammett常数（σp和σp +）呈线性关系。使用这种方法，树突的σp +常数配体对于2（n）和2（o）分别估计为0.25和0.24 。此外，硫原子上的NBO电荷在σp +参数下表现出潜在的响应。硫代酚基硫上的原子电荷随取代基的吸电子能力而变化，但是，电荷随吸电子能力的增加而增加。

  DOI：

  10.1039/b300048f
• 作为产物：
  描述：

  4-乙酰氨基苯硫酚 在 sodium hydrogensulfite 、 高碘酸 作用下， 以 水 为溶剂， 反应 1.58h， 以75%的产率得到N,N-(二硫-4,1-亚苯基)双乙酰胺
  参考文献：
  名称：

  An Improved Method for the Synthesis of Disulfides by Periodic acid and Sodium Hydrogen Sulfite in Water

  摘要：

  研究出了一种改进的方法，利用高碘酸和亚硫酸氢钠在水相中合成二硫化物。

  DOI：

  10.2174/157017810791514733

文献信息

• Natural gallic acid catalyzed aerobic oxidative coupling with the assistance of MnCO₃ for synthesis of disulfanes in water
  作者：Lijuan Song、Wenhao Li、Wenxue Duan、Jichao An、Shanyu Tang、Longjia Li、Guanyu Yang

  DOI：10.1039/c9gc00091g

  日期：——

  value in synthetic chemistry and bioscience. To pursue a sustainable approach for such a synthesis, an aerobic oxidative coupling method for the efficient preparation of organic disulfanes, using a low-toxic natural gallic acid as an organocatalyst, inexpensive MnCO3 as a cocatalyst, O2 as the terminal oxidant and water as the solvent, has been successfully developed. Such metal–organic cooperative catalytic

  硫键的形成在合成化学和生物科学中具有重要的意义和价值。为了寻求一种可持续的合成方法，一种需氧氧化偶联方法可有效地制备有机二硫，使用低毒的天然没食子酸作为有机催化剂，廉价的MnCO 3作为助催化剂，O 2作为末端氧化剂和水作为溶剂，已经成功开发。这种金属-有机协同催化方案可以以高达99％的收率获得各种对称和不对称的二硫烷。具有实际便利性和低催化剂负载量的革兰氏合成进一步说明了我们方法的实用性。
• Iodine-promoted stereoselective amidosulfenylation of electron-deficient alkynes
  作者：Fuhong Xiao、Dahan Wang、Shanshan Yuan、Huawen Huang、Guo-Jun Deng

  DOI：10.1039/c8ra04374d

  日期：——

  Iodine-promoted three-component synthesis of substituted β-amino sulfides has been developed starting from a propargyl ester, aliphatic secondary amine, and disulfide. This protocol provides a step-economic and highly regioselective entry to trisubstituted olefins with good substrate scope and functional group tolerance.

  从炔丙酯、脂肪族仲胺和二硫化物开始，开发了碘促进的取代β-氨基硫化物的三组分合成方法。该方案提供了一种经济且高度区域选择性的三取代烯烃进入方法，具有良好的底物范围和官能团耐受性。
• Synergistic Catalysis-Enabled Thia-Aza-Prins Cyclization with DMSO and Disulfides: Entry to Sulfenylated 1,3-Oxazinanes and Oxazolidines
  作者：Yang Ni、Honghua Zuo、Huaibin Yu、Yuzhou Wu、Fangrui Zhong

  DOI：10.1021/acs.orglett.8b02551

  日期：2018.9.21

  cyclization of alkenylamines with disulfides is reported, rendering the first synthesis of sulfenylated 1,3-oxazinanes and oxazolidines in good to high yields. Importantly, DMSO serves simultaneously as a reaction medium and a surrogate for formaldehyde. Mechanistic studies provide evidence that actions of CuBr2 and in situ formed sulfinic acids as a Lewis acid and Brønsted acid catalyst, respectively, synergistically

  据报道，新型的协同催化的二硫键烯基胺的硫杂氮杂-普林斯环化反应使亚磺酰化的1，3-恶二嗪酮和恶唑烷的首次合成具有很高的收率。重要的是，DMSO同时用作反应介质和甲醛的替代物。机理研究提供了证据，证明CuBr 2和原位形成亚磺酸的路易斯酸和布朗斯台德酸催化剂分别协同催化了这些环化过程。
• Stereoretentive C(<i>sp</i>³)–S Cross-Coupling
  作者：Feng Zhu、Eric Miller、Shuo-qing Zhang、Duk Yi、Sloane O’Neill、Xin Hong、Maciej A. Walczak

  DOI：10.1021/jacs.8b11211

  日期：2018.12.26

  We report a stereoretentive cross-coupling reaction of configurationally stable nucleophiles with disulfide and N-sulfenylsuccinimide donors promoted by Cu(I). We demonstrate the utility of this method in the synthesis of thioglycosides derived from simple alkyl and aryl thiols, thioglycosides, and in the glycodiversification of cysteine residues in peptides. These reactions operate well with carbohydrate

  我们报告了由 Cu(I) 促进的构型稳定的亲核试剂与二硫化物和 N-亚磺酰基琥珀酰亚胺供体的立体保持交叉偶联反应。我们证明了该方法在合成衍生自简单烷基和芳基硫醇、硫糖苷的硫糖苷以及肽中半胱氨酸残基的糖多样化中的实用性。在标准化条件下，这些反应在含有常见保护基团的碳水化合物底物和具有游离羟基和仲酰胺官能团的试剂上运行良好。竞争实验与计算 DFT 研究相结合确定了假定的异头中间体是一种有机铜物种，由于其寿命短，其构型稳定且抗差向异构化。随后从 Cu(III) 中间体的还原消除是快速和立体保持的。总之，糖基交叉偶联非常适合在脂肪族碳硫键的高度受控安装下的后期糖多样化和生物共轭。
• Visible-light promoted synthesis of 3-arylthioindoles from indoles and diaryl disulfides
  作者：Lin-miao Ye、Jie Chen、Peng Mao、Xue-jing Zhang、Ming Yan

  DOI：10.1016/j.tetlet.2017.05.090

  日期：2017.7

  3-Arylthioindoles could be synthesized in good yields via the photoirradiation of indoles and disulfides. The reaction is efficiently promoted by the catalytic amount of sodium iodide. A reaction mechanism involving the electrophilic substitution of indoles with arylsulfenyl iodine intermediates is suggested.

  可以通过吲哚和二硫化物的光辐射以高收率合成3-芳硫基吲哚。催化量的碘化钠可有效地促进反应。提出了涉及用芳基亚硫基碘中间体亲电取代吲哚的反应机理。