1,4-二异腈苯 | 935-16-0

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 芳香烃
• 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: 1,4-二异腈苯
• 中文别名: 对苯二甲氰
• 英文名称: 1,4-diisocyanobenzene
• 英文别名: 1,4-phenylenediisocyanide
• CAS: 935-16-0
• 化学式: C₈H₄N₂
• mdl: MFCD00012383
• 分子量: 128.133
• InChiKey: IXACFSRTSHAQIX-UHFFFAOYSA-N

物化性质

• 熔点：
  160 °C (dec.) (lit.)
• 稳定性/保质期：
  在常温常压下保持稳定

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 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：
  8.7
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26
• 危险类别码：
  R20/21/22
• 海关编码：
  2926909090
• WGK Germany：
  3
• 储存条件：
  常温、避光、通风干燥处，密封保存。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 1,4-Phenylene diisocyanide
CAS-No. : 935-16-0
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 toxicity, Inhalation (Category 4)
Acute toxicity, Dermal (Category 4)
Acute toxicity, Oral (Category 4)
Skin irritation (Category 2)
Eye irritation (Category 2)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Harmful by inhalation, in contact with skin and if swallowed. Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram
Signal word Warning
Hazard statement(s)
H302 Harmful if swallowed.
H312 Harmful in contact with skin.
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H332 Harmful if inhaled.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P280 Wear protective gloves/ protective clothing.
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
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
R-phrase(s)
R20/21/22 Harmful by inhalation, in contact with skin and if swallowed.
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : 1,4-Diisocyanobenzene
Formula : C8H4N2 C8H4N2
Molecular Weight : 128,13 g/mol
Component Concentration
1,4-Phenylene diisocyanide
CAS-No. 935-16-0 -

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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
Nausea, Headache, Vomiting, To the best of our knowledge, the chemical, physical, and toxicological
properties have not been thoroughly investigated.
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, nitrogen oxides (NOx)
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 vapors, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
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.Normal measures for preventive fire
protection.
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
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
Complete suit protecting against chemicals, 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).

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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 point/freezing Melting point/range: 160 °C - dec.
point
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- no data available
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, Strong acids
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
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation Harmful if inhaled. Causes respiratory tract irritation.
Ingestion Harmful if swallowed.
Skin Harmful if absorbed through skin. Causes skin irritation.
Eyes Causes serious eye irritation.
Signs and Symptoms of Exposure
Nausea, Headache, Vomiting, 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
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. Contact a licensed
professional waste disposal service to dispose of this material. 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. (1,4-Phenylene diisocyanide)
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: 9
Packaging group
ADR/RID: - IMDG: - IATA: -
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
no data available

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Section 16. OTHER INFORMATION
Further information
Copyright 2012 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：

  1,4-二异腈苯 在 selenium 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以85%的产率得到1,4-phenylene diisoselenocyanate
  参考文献：
  名称：

  糖衍生的异异壬酸酯，硒脲和亚硒唑的合成

  摘要：

  使用三光气作为脱水剂，三乙胺和黑色硒粉，通过一锅法从相应的甲酰胺开始，通过一锅法制备芳基，烷基和糖衍生的异异氰酸酯。还完成了通过O保护的糖衍生的异戊二烯酸酯与不同的胺的偶联，以及未保护的吡喃糖基胺与异戊烯酸酯的苯基的偶联的制备糖硒脲的制备。还报道了通过与苯甲酰基异异壬酸酯结合，由O-保护的2-氨基-2-脱氧-d-葡萄糖，与苯甲酰基溴的Se-烷基化以及酸催化的脱水来合成吡喃葡萄糖-2-基-硒代唑。未保护的N-（β-d-吡喃葡萄糖基）-N经过氧化氢水溶液处理后，将'-苯基硒脲转化为1,2-反式稠合的双环异脲。通过一锅式三步法，由硫代光气化，苯胺偶联和HgO介导的脱硫作用，由β-d-glycopyranosylamine制备相同的异脲。

  DOI：

  10.1016/j.tet.2009.01.038
• 作为产物：
  描述：

  1,1-dichloro-N-(4-isocyanophenyl)methanimine 在 lithium perchlorate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以94%的产率得到1,4-二异腈苯
  参考文献：
  名称：

  烷基和芳基异氰酸酯的电化学生成

  摘要：

  已经建立了一种有效且广泛适用的无试剂合成烷基和芳基异氰酸酯的方法。在恒定的阴极电势下，烷基和芳基碳亚氨基二氯的电化学还原反应以几乎定量的产率得到相应的异氰化物。起始原料的可用性，反应条件的温和性以及产物的容易分离是该方法的值得注意的有利特征。

  DOI：

  10.1016/s0040-4020(99)00509-8
• 作为试剂：
  描述：

  4-硝基苯硫醇 在 1,4-二异腈苯 、 silver 作用下， 以 乙醇 为溶剂， 生成 trans-4,4'-dimercaptoazobenzene
  参考文献：
  名称：

  通过用基于异氰化物的化合物修饰其表面，使银纳米晶体作为氧化还原催化剂而恢复活力

  摘要：

  银是用于氧化反应如乙烯环氧化的极好的催化剂，但它对还原反应的活性有限。在这里，我们报告了一种策略，可通过用异氰酸酯基化合物修饰其表面来活化Ag纳米晶体作为氧化还原催化剂，用于生产芳香族偶氮化合物。我们还利用原位指纹光谱通过表面增强拉曼光谱探测催化表面上所有化学物质的振动模式来获得对反应机理的分子认识。我们确定异氰酸酯与Ag纳米晶体的结合使Ag可以从硝基芳香族化合物的硝基中提取氧原子，然后使用这些原子将异氰酸酯氧化为异氰酸酯。同时，两个相邻的脱氧硝基芳族分子之间的偶联导致形成芳族偶氮化合物。

  DOI：

  10.1039/d0sc04385k

文献信息

• Tuning the Lifetime of Transient Phases of Mechanochromic Gold Isocyanide Complexes through Functionalization of the Terminal Moieties of Flexible Side Chains
  作者：Tomohiro Seki、Kentaro Kashiyama、Shiki Yagai、Hajime Ito

  DOI：10.1246/cl.170482

  日期：2017.9.5

  of the transient phases of luminescent mechanochromic gold isocyanide complexes could be tuned through the modification of the termini of flexible side chains. Upon grinding, these complexes initially showed an emission color change from blue to yellow. The yellow emission spontaneously changed to blue or green, but with different lifetimes of the yellow-emitting transient phases depending on the substituents

  发光机械变色金异氰化物配合物的瞬态寿命可以通过柔性侧链末端的修饰来调整。研磨后，这些复合物最初显示出从蓝色到黄色的发光颜色变化。黄色发射自发地变为蓝色或绿色，但根据取代基的不同，黄色发射瞬态相的寿命不同。还描述了机械引起的结构变化的细节。
• Diiron Oxadithiolate Type Models for the Active Site of Iron-Only Hydrogenases and Biomimetic Hydrogen Evolution Catalyzed by Fe₂(<i>μ</i>-SCH₂OCH₂S-<i>μ</i>)(CO)₆
  作者：Li-Cheng Song、Zhi-Yong Yang、Hong-Zhu Bian、Yang Liu、Hu-Ting Wang、Xu-Feng Liu、Qing-Mei Hu

  DOI：10.1021/om0507373

  日期：2005.12.1

  The biomimetic chemistry of single and double oxadithiolatodiiron-containing model compounds for the active site of Fe-only hydrogenases (FeHases) has been systematically studied. The simplest such model, Fe2(μ-SCH2OCH2S-μ)(CO)6 (1), was prepared by reaction of (μ-S2)Fe2(CO)6 with 2 equiv of Et3BHLi followed by direct treatment with excess (ClCH2)2O or by successive treatment with 2 equiv of CF3CO2H

  已经系统地研究了单一和双重含氧二硫代latodiiron的模型化合物的仿生化学，用于仅铁的氢酶（FeHases）的活性位点。最简单的模型Fe 2（μ- SCH 2 OCH 2 S- μ）（CO）6（1）是通过（μ- S 2）Fe 2（CO）6与2当量的Et 3 BHLi反应制得的然后直接用过量（ClCH 2）2 O处理或连续用2当量CF 3 CO 2 H和过量（ClCH2）2 O在Et 3 N的存在下进行。1与1当量的Me 3 NO在室温下在MeCN中进一步反应，然后处理中间体Fe 2（μ- SCH 2 OCH 2 S- μ）（CO）5 L（L = MeCN或Me 3 N）和1当量的Et 4 NCN，PPh 3或Cp（CO）2 FeSPh给出了单个模型Fe 2（μ- SCH 2 OCH 2 S- μ）（CO）5大号一（2，L a＝（CN）（Et 4 N）；3，PPh 3 ; 如图4所示，Cp（CO）2
• Mild C−F Activation in Perfluorinated Arenes through Photosensitized Insertion of Isonitriles at 350 nm
  作者：Frauke Weidlich、Naoto Esumi、Dongyang Chen、Christian Mück‐Lichtenfeld、Eli Zysman‐Colman、Armido Studer

  DOI：10.1002/adsc.201901126

  日期：2020.1.23

  blocks, via C−H fluorination or via selective activation of perfluorinated compounds to give the partially fluorinated congeners. Especially the direct activation of C−F bonds, one of the strongest σ‐bonds, still remains challenging and new strategies for C−F activation are desirable. Herein a method for the photochemical activation of aromatic C−F bonds is presented. It is shown that isonitriles selectively

  氟化化合物已在农业化学工业，药物化学和材料科学领域中变得重要。因此，过去已经开发了各种制备方法。氟化化合物可通过与氟化结构单元共轭，CH氟化或通过全氟化合物的选择性活化而获得部分氟化同源物。尤其是C-F键（最强的σ键）之一的直接激活仍然具有挑战性，因此需要新的C-F激活策略。在此提出了一种光化学活化芳族CF键的方法。结果表明，异腈选择性地插入芳族CF键中，而脂族CF键不受影响。机理研究表明，该反应是通过在350 nm处由光激发的苯乙酮将异腈间接激发至三重态而进行的。由于所使用的光线相对温和，因此该方法显示出较高的官能团耐受性，并且苯甲酰亚胺基氟化物类的各种化合物可从芳基异腈和市售的全氟化芳烃中获得。
• Room-Temperature Metal-Free Multicomponent Polymerizations of Elemental Selenium toward Stable Alicyclic Poly(oxaselenolane)s with High Refractive Index
  作者：Xiuying Wu、Junxia He、Rongrong Hu、Ben Zhong Tang

  DOI：10.1021/jacs.1c06732

  日期：2021.9.29

  selenium-involving covalent bonds. In this work, room-temperature metal-free multicomponent polymerizations (MCPs) of elemental selenium, diisocyanides, and dipropargyl alcohols were developed, and polymers with a selenium-containing aliphatic heterocycle, 1,3-oxaselenolane, were synthesized through these MCPs directly from elemental selenium. The alicyclic poly(oxaselenolane)s enjoyed high yields (up to

  含硒聚合物是一组引人入胜的功能聚合物，具有独特的结构、性能和应用，最近得到了发展，但例子有限。开发具有结构和功能多样性的含硒聚合物面临的挑战包括缺乏经济安全的单体、缺乏高效便捷的合成方法以及含硒共价键的稳定性差。在这项工作中，开发了元素硒、二异氰化物和二炔丙醇的室温无金属多组分聚合 (MCP)，并通过这些 MCP 直接从元素硒。脂环族聚 (oxaselenolane) 的收率很高（高达 93%），高分子量（高达 15 600 g/mol）、高热稳定性和化学稳定性、良好的溶解性和可加工性。随着聚（氧杂硒醇烷）的结构设计及其高达 33.7 wt% 的高硒含量，其旋涂薄膜的折射率在 633 nm 处可达到 1.8026，在 1700 nm 处保持为 1.7770。预计这些高效、便捷、温和、经济的元素硒多组分聚合反应可以促进硒相关聚合物化学的发展，加速探索多样化的含硒功能高分子材料。他们的旋涂薄膜的折射率在
• 一种草铵膦的合成方法
  申请人：浙江工业大学

  公开号：CN109776605B

  公开（公告）日：2021-08-03

  一种草铵膦的合成方法，包括以下步骤：步骤(1)、以3‑甲基正丁氧基膦酰基丙醛、醋酸、异腈、氨水为原料，在溶剂中充分反应；步骤(2)、将步骤(1)的反应液蒸馏脱除溶剂；步骤(3)、向步骤(2)的产品中加入盐酸水溶液水解得到草铵膦。本发明提供了一种绿色环保、成本低的草铵膦的合成方法，并且得到的草铵膦的收率较高；本发明避免了以往合成路线中剧毒物质氰化钠的使用，该反应条件温和，收率较高，具有很好的工业化前景。

表征谱图