苯甲腈-d5 | 2102-15-0

• 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: 苯甲腈-d5
• 中文别名: 氰化苯-D5
• 英文名称: benzonitrile-d₅
• 英文别名: pentadeuterobenzonitrile；d₅-benzonitrile；Benzonitrile-d5；2,3,4,5,6-pentadeuteriobenzonitrile
• CAS: 2102-15-0
• 化学式: C₇H₅N
• 分子量: 108.084
• InChiKey: JFDZBHWFFUWGJE-RALIUCGRSA-N

物化性质

• 熔点：
  −13 °C(lit.)
• 沸点：
  191 °C(lit.)
• 密度：
  1.059 g/mL at 25 °C
• 闪点：
  161 °F
• 溶解度：
  可溶于氯仿、甲醇（微量）
• 稳定性/保质期：

  在常温常压下稳定。

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  8
• 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：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S27,S36/37/39,S45
• 危险类别码：
  R21/22,R41,R38
• WGK Germany：
  2
• 危险品运输编号：
  UN 2470 6.1/PG 3

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : Benzonitrile-d5
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. : 2102-15-0
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
Acute toxicity, Dermal (Category 4), H312
Acute toxicity, Oral (Category 4), H302
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
Xn Harmful R21/22
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)
H302 Harmful if swallowed.
H312 Harmful in contact with skin.
Precautionary statement(s)
P280 Wear protective gloves/ protective clothing.
Supplemental Hazard none
Statements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Chemical characterization : Isotopically labeled
Synonyms : Phenyl-d5 cyanide
Formula : C7D5N
Molecular Weight : 108,15 g/mol
CAS-No. : 2102-15-0
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
Benzonitrile-d5
CAS-No. 2102-15-0 Acute Tox. 4; H302, H312 <= 100 %
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
Benzonitrile-d5
CAS-No. 2102-15-0 Xn, R21/22 <= 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
Flush eyes with water as a precaution.
If swallowed
Do NOT induce vomiting. 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
no data available
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
Use water spray to cool unopened containers.

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid breathing vapours, mist or gas. Ensure adequate ventilation.
Remove all sources of ignition. Beware of vapours accumulating to form explosive concentrations.
Vapours can accumulate in low areas.
For personal protection see section 8.
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
Contain spillage, and then collect with an electrically protected vacuum cleaner or by wet-brushing and
place in container for disposal according to local regulations (see section 13). 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 inhalation of vapour or mist.
Keep away from sources of ignition - No smoking.Take measures to prevent the build up of electrostatic
charge.
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. Containers which are
opened must be carefully resealed and kept upright to prevent leakage.
Store under inert gas. hygroscopic
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
Face shield and safety glasses Use equipment for eye protection tested and approved under
appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
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.
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
Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator
with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup
to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air
respirator. Use respirators and components tested and approved under appropriate government
standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into
the environment must be avoided.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: liquid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: -13 °C - lit.
point
f) Initial boiling point and 191 °C - lit.
boiling range
g) Flash point 70 °C - closed cup
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 1 hPa at 20 °C
l) Vapour density 3,56 - (Air = 1.0)
m) Relative density 1,059 g/mL at 25 °C1,059 g/cm3 at 25 °C
n) Water solubility ca.10 g/l
o) Partition coefficient: n- log Pow: 1,56
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
Surface tension 38,79 mN/m at 25 °C
Relative vapour density 3,56 - (Air = 1.0)

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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
Heat, flames and sparks.
Incompatible materials
Bases, Strong oxidizing agents, Strong reducing agents, Acids, Chlorates, Nitrates, Plastics
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
Inhalation: no data available
Dermal: no data available
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitisation
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
no data available
Additional Information
RTECS: Not available
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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SECTION 12: Ecological information
Toxicity
no data available
Persistence and degradability
Biodegradability Biotic/Aerobic
Result: - Readily biodegradable.
Biotic/Aerobic - Exposure time 7 d
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
Harmful to aquatic life.

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SECTION 13: Disposal considerations
Waste treatment methods
Product
This combustible material may be burned in a chemical incinerator equipped with an afterburner and
scrubber. Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

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SECTION 14: Transport information
UN number
ADR/RID: 2224 IMDG: 2224 IATA: 2224
UN proper shipping name
ADR/RID: BENZONITRILE
IMDG: BENZONITRILE
IATA: Benzonitrile
Transport hazard class(es)
ADR/RID: 6.1 IMDG: 6.1 IATA: 6.1
Packaging group
ADR/RID: II IMDG: II IATA: II
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
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  苯甲腈-d5 生成
  参考文献：
  名称：

  Retro-Diels-Alder fragmentation of 2,5,6-triphenyl-3,4-didehydropyridine generated by flash vacuum pyrolysis at 900°C

  摘要：

  DOI：

  10.1016/0040-4039(92)80025-f
• 作为产物：
  描述：

  氘代甲苯 在 1,3-二溴-5,5-二甲基海因 、 过氧化苯甲酰 、 ammonium hydroxide 、 碘 作用下， 以 四氯化碳 为溶剂， 反应 15.0h， 生成 苯甲腈-d5
  参考文献：
  名称：

  Rh(III)-催化级联环化产生螺吡咯并异喹啉衍生物的 N-乙酰链

  摘要：

  开发了一种新的铑( III )催化多步级联螺环化方法，以恶二唑为导向基团合成新型螺吡咯并异喹啉衍生物的N-乙酰链。这种一锅法反应还分离出芳基恶二唑衍生物作为交叉偶联中间体。这种简单的方法可以有效地扩大异喹啉和芳基恶二唑骨架的范围。

  DOI：

  10.1039/d2ob00137c

文献信息

• Nickel-Catalyzed Markovnikov Transfer Hydrocyanation in the Absence of Lewis Acid
  作者：Nils L. Frye、Anup Bhunia、Armido Studer

  DOI：10.1021/acs.orglett.0c01454

  日期：2020.6.5

  Hydrocyanation in the absence of toxic HCN gas is highly desirable. Addressing that challenge, transition-metal-catalyzed transfer hydrocyanation using safe HCN precursors has been developed, but these reagents generally require a Lewis acid for activation, and the control of regioselectivity often remains problematic. In this Letter, a Ni-catalyzed highly Markovnikov-selective transfer hydrocyanation

  在没有有毒的HCN气体的情况下进行氢氰化是非常需要的。为了应对这一挑战，已经开发出使用安全的HCN前体的过渡金属催化的转移氢氰化反应，但是这些试剂通常需要路易斯酸进行活化，并且对区域选择性的控制通常仍然存在问题。在这封信中，报道了在没有任何路易斯酸的情况下进行的镍催化的高度马尔可夫尼科夫选择性转移氢氰化反应。易制得的原芳族1-异丙基环己-2,5-二烯-1-腈作为HCN源，该反应显示出较宽的底物范围和较高的官能团耐受性。将末端苯乙烯衍生物，二烯和内部炔烃以良好的选择性转化为优异的选择性。机理研究为区域选择性的起源提供了见识。
• Palladium-Catalyzed Late-Stage Direct Arene Cyanation
  作者：Da Zhao、Peng Xu、Tobias Ritter

  DOI：10.1016/j.chempr.2018.09.027

  日期：2019.1

  Methods for direct benzonitrile synthesis are sparse, despite the versatility of cyano groups in organic synthesis and the importance of benzonitriles for the dye, agrochemical, and pharmaceutical industries. We report the first general late-stage aryl C–H cyanation with broad substrate scope and functional-group tolerance. The reaction is enabled by a dual-ligand combination of quinoxaline and an

  尽管氰基在有机合成中具有多功能性，并且苯甲腈在染料，农业化学和制药行业中的重要性，但直接合成苯甲腈的方法仍然很少。我们报告了第一个一般的晚期芳基C–H氰化反应，具有较宽的底物范围和官能团耐受性。喹喔啉和氨基酸衍生的配体的双配体结合使反应得以实现。该方法适用于几种市售的小分子药物，常用药效团和有机染料的直接氰化。
• Rhodium-catalyzed Synthesis of 1-(Acylamino)isoquinolines through Direct Annulative Coupling of 3-Aryl-1,2,4-oxadiazoles with Alkynes
  作者：Yuji Nishii、Anne-Katrin Bachon、Sanghun Moon、Carsten Bolm、Masahiro Miura

  DOI：10.1246/cl.170536

  日期：2017.9.5

  A Rh(III)-catalyzed direct annulative coupling of 3-aryl-1,2,4-oxadiazoles with alkynes through coordination-assisted C–H activation is developed, providing a facile route to 1-(acylamino)isoquinolines. The oxadiazole ring acts as a directing group as well as an internal oxidant.

  通过配位辅助的 C-H 活化，Rh(III) 催化的 3-芳基-1,2,4-恶二唑与炔烃的直接环合偶联，为制备 1-（酰基氨基）异喹啉提供了一条简便的途径。恶二唑环作为导向基团和内部氧化剂。
• Oxadiazolone-Enabled Synthesis of Primary Azaaromatic Amines
  作者：Xiaolong Yu、Kehao Chen、Fan Yang、Shanke Zha、Jin Zhu

  DOI：10.1021/acs.orglett.6b02814

  日期：2016.10.21

  Despite their tremendous synthetic and pharmaceutical utility, primary azaaromatic amines remain elusive for access based on a generally applicable C–H functionalization strategy. An oxadiazolone-enabled approach is reported for convenient entry into N-unsubstituted 1-aminoisoquinolines through Co(III)-catalyzed redox-neutral, step-, atom-, and purification-economic C–H functionalization with alkynes

  尽管它们具有巨大的合成和制药用途，但基于普遍适用的C–H官能化策略，氮杂芳族伯胺仍然难以获得。恶二唑酮使能的方法据报道可方便地通过炔烃通过Co（III）催化的氧化还原中性，阶跃，原子和纯化经济的CHH功能化进入N-未取代的1-氨基异喹啉。甲15 Ñ标记实验揭示了两个恶二唑酮N原子作为引导位点的有效性。可以将已安装的伯胺用作合成有用的手柄，用于附接发散的附件。
• Cobalt(III)-Catalyzed Oxadiazole-Directed C–H Activation for the Synthesis of 1-Aminoisoquinolines
  作者：Fan Yang、Jiaojiao Yu、Yun Liu、Jin Zhu

  DOI：10.1021/acs.orglett.7b01119

  日期：2017.6.2

  heterocycles have been identified as effective directing groups (DGs) in C–H functionalization but can be retained as undesired bulky substituents in the final products. Herein, we report a Co(III)-catalyzed 1-aminoisoquinoline synthesis strategy based on oxadiazole-directed aromatic C–H coupling with alkynes and a subsequent redox-neutral C–N cyclization reaction. This labile N–O bond-based protocol

  在C–H功能化中，芳香杂环已被确认为有效的导向基团（DG），但在最终产品中可保留为不希望的大取代基。在本文中，我们报告了基于乙二唑的芳烃C–H与炔烃偶联的Co（III）催化的1-氨基异喹啉合成策略，以及随后的氧化还原中性C–N环化反应。这种基于N–O键的不稳定方案允许耐受各种官能团。