3,6-二氯-1,2-苯二硫醇 | 87314-49-6

• 物质功能分类: 化学试剂 - 有机试剂 - 硫醇/硫酚
• 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: 3,6-二氯-1,2-苯二硫醇
• 英文名称: 3,6-dichlorobenzene-1,2-dithiol
• 英文别名: 3,6-dichloro-1,2-benzenedithiol
• CAS: 87314-49-6
• 化学式: C₆H₄Cl₂S₂
• mdl: MFCD00216665
• 分子量: 211.136
• InChiKey: AJCUDWCLDWDLNY-UHFFFAOYSA-N

物化性质

• 熔点：
  58-60°C (lit.)
• 沸点：
  314.9±37.0 °C(Predicted)
• 密度：
  1.523±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  如果按照规格正确使用和储存，则不会发生分解，也未有已知的危险反应。

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  2
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2930909090
• WGK Germany：
  3
• 储存条件：
  请将贮藏器密封保存，在阴凉、干燥处存放，并确保工作环境有良好的通风或排气设施。

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 3,6-Dichloro-1,2-benzenedithiol
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 87314-49-6
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
Skin irritation (Category 2), H315
Eye irritation (Category 2), H319
Specific target organ toxicity - single exposure (Category 3), H335
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Xi Irritant R36/37/38
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Warning
Hazard statement(s)
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Formula : C6H4Cl2S2
Molecular Weight : 211,13 g/mol
CAS-No. : 87314-49-6
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
3,6-Dichloro-1,2-benzenedithiol
CAS-No. 87314-49-6 Skin Irrit. 2; Eye Irrit. 2; STOT <= 100 %
SE 3; H315, H319, H335
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
3,6-Dichloro-1,2-benzenedithiol
CAS-No. 87314-49-6 Xi, R36/37/38 <= 100 %
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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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
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
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
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
no data available

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SECTION 5: Firefighting 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, Sulphur oxides, Hydrogen chloride gas
Advice for firefighters
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
Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
For personal protection see section 8.
Environmental precautions
Do not let product enter drains.
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
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Stench.
Specific end use(s)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated

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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
Safety glasses with side-shields conforming to EN166 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
impervious clothing, The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
Use respirators and components tested and approved under appropriate government standards
such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour Stench.
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 58 - 60 °C - lit.
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evapouration 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: 3,612
octanol/water
p) Auto-ignition 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
Stable under recommended storage conditions.
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
In the event of fire: see section 5

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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 sensitisation
The preceding data, or interpretation of data, was determined using Quantitative Structure Activity
Relationship (QSAR) modeling.
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
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
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
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
no data available

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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: - IMDG: - IATA: 3335
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Aviation regulated solid, n.o.s. (3,6-Dichloro-1,2-benzenedithiol)
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: 9
Packaging group
ADR/RID: - IMDG: - IATA: III
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15: Regulatory information
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
For this product a chemical safety assessment was not carried out

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SECTION 16: Other information
Full text of H-Statements referred to under sections 2 and 3.
Eye Irrit. Eye irritation
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Skin Irrit. Skin irritation
STOT SE Specific target organ toxicity - single exposure
Full text of R-phrases referred to under sections 2 and 3
Xi Irritant
R36/37/38 Irritating to eyes, respiratory system and skin.
Further information
Copyright 2013 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

反应信息

• 作为反应物：
  描述：

  3,6-二氯-1,2-苯二硫醇 在 molybdenium(VI) dioxodichloride 、 四乙基碘化铵 、 三乙胺 作用下， 以 甲醇 为溶剂， 以44%的产率得到1,4,7,10-Tetrachloro-5,6,11,12-tetrathia-dibenzo[a,e]cyclooctene
  参考文献：
  名称：

  一系列新的钼-（IV），-（V）和-（VI）二硫代钼酸盐化合物作为钼酶的活性位点模型：制备，晶体结构，光谱/电化学性质和氧原子转移的反应活性

  摘要：

  分离出一组新的含3,6-二氯-1,2-苯二硫代钼酸酯（bdtCl 2）的钼（IV），-（V）和-（VI）化合物，并通过晶体学和其他光谱技术表征为活性部位砷化酶之一的亚砷酸氧化酶的模型。通过使MoO 2 Cl 2与bdtCl 2，相关的二硫辛烯和硫代邻苯二甲酸酯反应，可以高收率地制备MoO 2化合物。甲醇在低温下。bdtCl 2 配体 特别稳定了MoO化合物 氧化作用+4和+5以及氧化数为+6的MoO 2化合物。化合物（Et 4 N）2 [Mo VI O 2（bdtCl 2）2 ]（1），（Et 4 N）2 [Mo IV O（bdtCl 2）2 ]（2）和（Et 4 N）[Mo V O（bdtCl 2）2 ]（3）已成功分离，而（Et 3 NH）2 [MoO 2（thiocatecholate）2 ]（ 6）逐渐分解为乙腈。在比较键距和键角的基础上，提出了一种类似于（1）的变形八面体结构，用

  DOI：

  10.1039/b503828f
• 作为产物：
  描述：

  1,2,3,4-四氯苯 在 sodium hydrosulfide monohydrate 、 铁粉 、 sulfur 、 zinc(II) oxide 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 、 甲醇 、 水 为溶剂， 反应 18.0h， 以13%的产率得到3,6-二氯-1,2-苯二硫醇
  参考文献：
  名称：

  通过苯环上的取代基对钴二硫代噻吩配合物进行精细的电子态调节

  摘要：

  摘要一系列3,6-和4,5-二卤素取代的1,2-苯二硫醇（H2bdt）配体（3,6-X12-4,5-X22-1,2-H2bdt）（X2 = H， X1 = F（1a），Cl（1b），Br（1c）； X1 = H，X2 = Cl（4））及其钴配合物[Cp * Co（3,6-X12-4,5-X22 -1,2-bdt）]（X2 = H，X1 = F（2a），Cl（2b），Br（2c）； X1 = H，X2 = Cl（5）），是通过改良的选择性硫醇化反应合成的。还合成了1，2-二苯基取代的钴二硫代钴络合物（2d）。通过单晶X射线衍射分析确定所有钴二硫代亚硒酸酯配合物的分子结构。化合物2a，5和12显示出具有分子间相互作用的独特堆积结构，这证实了它们是具有Cp *配体的半三明治型金属二硫代噻吩配合物的第一个实例。使用紫外可见光谱测量和循环伏安法研究了苯取代基的类型和位置对金属二硫杂环戊烯环的影响。结

  DOI：

  10.1016/j.poly.2016.05.062
• 作为试剂：
  描述：

  油酸甲酯 在 3,6-二氯-1,2-苯二硫醇 、 SiPr-Blechert catalyst 、 diethylzinc 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 16.0h， 以25%的产率得到dimethyl (Z)-octadec-9-ene-1,18-dioate
  参考文献：
  名称：

  立体定向烯烃复分解变得容易：从商业原料现场生成高选择性钌催化剂

  摘要：

  据报道原位制备高度立体保持性的钌基复分解催化剂。该方法完全避免了中间体和对空气敏感的催化剂的分离，因此可以快速访问和评估多种二硫代钌催化剂。建立了无需使用手套箱即可进行交叉复分解反应的程序，并且即使在小规模下也不需要Schlenk技术。因此，本报告中显示的化学方法可供所有执业有机化学人员使用，并提供了一种鉴定新的立体保持性催化剂的有力方法。

  DOI：

  10.1021/acs.orglett.8b02943

文献信息

• Synthesis and crystal structures of ion-pairs based on anionic iron-dithiolenes and alkylammonium as countercation
  作者：Oscar Castillo、Esther Delgado、Diego Hernández、Elisa Hernández、Avelino Martín、Maria Pérez、Félix Zamora

  DOI：10.1016/j.molstruc.2019.06.051

  日期：2019.11

  (X = Cl or H) or FeCl3·6H2O with HSC6H2X2SH and either ONMe3 or NaOH/Et4NBr give rise to a series of iron dithiolene ion-pairs of formula (RN)2[Fe2(SC6H2X2S)4] [X = Cl or H; R=(CH3)3H or (CH3CH2)4], or (CH3CH2)4N}2[Fe(SC6H2Cl2S)3]. The crystal structures of these iron dithiolates show very intricate crystal structure involving electrostatic interactions and a variety of complex H-bonds, Cl⋯Cl and aromatic

  摘要 [Fe2(CO)6(μ-SC6H2X2S)] (X = Cl 或 H) 或 FeCl3·6H2O 与 HSC6H2X2SH 和 ONMe3 或 NaOH/Et4NBr 之间的反应产生一系列式 (RN )2[Fe2(SC6H2X2S)4] [X = Cl 或 H; R=(CH3)3H 或 (CH3CH2)4]，或(CH3CH2)4N}2[Fe(SC6H2Cl2S)3]。这些二硫醇铁的晶体结构显示出非常复杂的晶体结构，涉及静电相互作用和各种复杂的氢键、Cl⋯Cl 和芳香相互作用。使用四乙基铵 (4-5) 代替三甲基铵 (1-3) 反离子意味着不那么强的超分子相互作用和化合物更容易发生多晶现象，如 5a 和 5b 的情况。
• Continuous Flow <i>Z</i> ‐Stereoselective Olefin Metathesis: Development and Applications in the Synthesis of Pheromones and Macrocyclic Odorant Molecules**
  作者：Jennifer Morvan、Tom McBride、Idriss Curbet、Sophie Colombel‐Rouen、Thierry Roisnel、Christophe Crévisy、Duncan L. Browne、Marc Mauduit

  DOI：10.1002/anie.202106410

  日期：2021.9

  The first continuous flow Z-selective olefin metathesis process is reported. Key to realizing this process was the adequate choice of stereoselective catalysts combined with the design of an appropriate continuous reactor setup. The designed continuous process permits various self-, cross- and macro-ring-closing-metathesis reactions, delivering products in high selectivity and short residence times

  报道了第一个连续流动 Z-选择性烯烃复分解过程。Key to realizing this process was the adequate choice of stereoselective catalysts combined with the design of an appropriate continuous reactor setup. 设计的连续工艺允许各种自、交叉和大环闭环复分解反应，以高选择性和短停留时间提供产品。该技术通过直接应用于一系列信息素和大环气味分子的制备来举例说明，并在一个伸缩的 Z 选择性交叉复分解/迪克曼环化序列中达到高潮，以获取 ( Z )-Civetone，并结合一系列连续搅拌罐反应堆。
• [EN] CATALYSTS FOR EFFICIENT Z-SELECTIVE METATHESIS<br/>[FR] CATALYSEURS POUR UNE MÉTATHÈSE Z-SÉLECTIVE EFFICACE
  申请人：TRUSTEES BOSTON COLLEGE

  公开号：WO2014201300A1

  公开（公告）日：2014-12-18

  The present application provides, among other things, compounds and methods for metathesis reactions. In some embodiments, provided compounds promote highly efficient and highly Z-selective metathesis. In some embodiments, provided compounds and methods are particularly useful for producing allyl alcohols. In some embodiments, provided compounds have the structure of formula I. In some embodiments, provided compounds comprise ruthenium, and a ligand bonded to ruthenium through a sulfur atom.

  本申请提供了化合物和用于交换反应的方法，其中提供的化合物在某些实施例中促进高效且高Z-选择性的交换反应。在某些实施例中，提供的化合物和方法特别适用于生产烯丙醇。在某些实施例中，提供的化合物具有式I的结构。在某些实施例中，提供的化合物包括钌，并且通过硫原子与钌结合的配体。
• [EN] OLEFIN METATHESIS CATALYSTS<br/>[FR] CATALYSEURS DE MÉTATHÈSE D'OLÉFINES
  申请人：MATERIA INC

  公开号：WO2017100585A1

  公开（公告）日：2017-06-15

  This invention relates generally to metathesis catalysts and the use of such catalysts in the metathesis of olefins and olefin compounds, more particularly, in the use of such catalysts in Z and E selective olefin metathesis reactions. The invention has utility in the fields of organometallics and organic synthesis.

  这项发明通常涉及重整催化剂以及在烯烃和烯烃化合物的重整中使用此类催化剂，更具体地，在Z和E选择性烯烃重整反应中使用此类催化剂。该发明在有机金属化合物和有机合成领域具有实用性。
• Immobilized Cobalt Bis(benzenedithiolate) Complexes: Exceptionally Active Heterogeneous Electrocatalysts for Dihydrogen Production from Mildly Acidic Aqueous Solutions
  作者：Shawn C. Eady、Molly M. MacInnes、Nicolai Lehnert

  DOI：10.1021/acs.inorgchem.7b01589

  日期：2017.10.2

  V versus platinum. Controlled-potential electrolysis studies performed in 0.5 M H2SO4 at −0.5 V versus SHE show impressive initial rate constants of over 500 s–1 under bulk electrolysis conditions; however, steady catalyst deactivation over an 8 h period is observed, with turnover numbers reaching 9.1 × 106. Electrolysis studies reveal that halide substitution is a central factor in improving the turnover

  制备了一系列具有不同苯二硫代酸酯（一般缩写：bdt 2–）环取代（S 2 C 6 X 4 2–）的钴双（苯二硫代）钴配合物，并将其吸附在由（a）氧化石墨烯（RGO）组成的廉价电极上电沉积在掺氟氧化锡（FTO）和（b）高度有序的热解石墨（HOPG）上。催化剂吸附的电极通过X射线光电子能谱表征。随着卤化物取代的增加，TBA [Co（S 2 C 6 H 4）2从2.7×10 –11 mol cm –2]显着提高了整个配体系列的催化剂负载量（1）到TBA [Co（S 2 C 6 Cl 4）2 ]（3）]增加到6.22×10 –10 mol cm -2，并增加苯二硫代盐配体的环大小[最高达3.10×10 –9 mol cm –2用于TBA [Co（S 2 C 10 H 6）2 ]（6）]。对固定在HOPG上的配合物进行电催化分析会引起还原电流响应，表明存在三氟乙酸的弱酸性水溶液（pH 2-4）时产生二氢，相对于SHE，过电势约为0