苯乙烯-Alpha-d1 | 1193-80-2

• 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: 苯乙烯-Alpha-d1
• 中文别名: 苯乙烯-α-d1；苯乙烯-D1
• 英文名称: α-deuteriostyrene
• 英文别名: α-Deuterio-styrol；α-d-styrene；styrene-α-d1；Styrol-α-d(1)；Styrol-α-d；α-<2H>-Styrol；α-Deutero-styrol；α-D-Styrol；1-Deuterioethenylbenzene
• CAS: 1193-80-2
• 化学式: C₈H₈
• 分子量: 105.144
• InChiKey: PPBRXRYQALVLMV-VMNATFBRSA-N

物化性质

• 熔点：
  -31 °C
• 沸点：
  50-51 °C25 mm Hg(lit.)
• 密度：
  0.918 g/mL at 25 °C
• 闪点：
  88 °F
• 溶解度：
  可溶于丙酮（少量）、DMSO（少量）
• 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)：
  2.9
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S23
• 危险类别码：
  R10
• WGK Germany：
  2
• 危险品运输编号：
  UN 2055 3/PG 3
• 储存条件：
  常温、避光、存于通风干燥处。

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
: Styrene-α-d1
Product name
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. : 1193-80-2
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
Eye irritation (Category 2), H319
Flammable liquids (Category 3), H226
Acute toxicity, Inhalation (Category 4), H332
Skin irritation (Category 2), H315
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
R10
Xn Harmful R20
Xi Irritant R36/38
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)
H226 Flammable liquid and vapour.
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H332 Harmful if inhaled.
Precautionary statement(s)
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
Chemical characterization : Isotopically labeled
Formula : C8DH7
Molecular Weight : 105,16 g/mol
CAS-No. : 1193-80-2
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
Styrene-a-d1
Flam. Liq. 3; Acute Tox. 4; -
Skin Irrit. 2; Eye Irrit. 2; H226,
H315, H319, H332
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
Styrene-a-d1
Xn, R10 - R20 - R36/38 -
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
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
Carbon oxides
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.
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).
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
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, Flame retardant antistatic protective 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
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.

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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: -31 °C
point
f) Initial boiling point and 145 - 146 °C - lit.
boiling range
g) Flash point 31,1 °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 no data available
l) Vapour density no data available
m) Relative density 0,918 g/mL at 25 °C0,918 g/cm3 at 25 °C
n) Water solubility no data available
o) Partition coefficient: n- no data available
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
Heat, flames and sparks.
Incompatible materials
no data available
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
Respiratory or skin sensitisation
no data available
Germ cell mutagenicity
Carcinogenicity
IARC: 2B - Group 2B: Possibly carcinogenic to humans (Styrene-a-d1)
Reproductive toxicity
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
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
Burn in a chemical incinerator equipped with an afterburner and scrubber but exert extra care in igniting
as this material is highly flammable. 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: 2055 IMDG: 2055 IATA: 2055
UN proper shipping name
ADR/RID: STYRENE MONOMER, STABILIZED
IMDG: STYRENE MONOMER, STABILIZED
IATA: Styrene monomer, stabilized
Transport hazard class(es)
ADR/RID: 3 IMDG: 3 IATA: 3
Packaging group
ADR/RID: III IMDG: III 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.
Acute Tox. Acute toxicity
Eye Irrit. Eye irritation
Flam. Liq. Flammable liquids
H226 Flammable liquid and vapour.
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H332 Harmful if inhaled.
Skin Irrit. Skin irritation
Full text of R-phrases referred to under sections 2 and 3
Xn Harmful
R10 Flammable.
R20 Harmful by inhalation.
R36/38 Irritating to eyes 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：

  苯乙烯-Alpha-d1 在 bis(η3-allyl-μ-chloropalladium(II)) 、 (R)-2-bis[3,5-bis(CF₃)phenyl]phosphino-1,1'-binaphthyl 、 三氯硅烷 作用下， 反应 1.0h， 以94%的产率得到trichloro-[(1S)-1-deuterio-1-phenylethyl]silane
  参考文献：
  名称：

  Asymmetric Hydrosilylation of Styrenes Catalyzed by Palladium−MOP Complexes:  Ligand Modification and Mechanistic Studies

  摘要：

  In the palladium-catalyzed asymmetric hydrosilylation of styrene (3a) with trichlorosilane, several chiral monophosphine ligands, (R)-2-diarylphosphino-1,1'-binaphthyls(2a-g), were examined for their enantioselectivity. The highest enantioselectivity was observed in the reaction with (R)-2-bis [3,5-bis(trifluoromethyl)phenyl] phosphino-l,1'-binaphthyl (2g), which gave (S)-1-phenylethanol (5a) of 98% ee after oxidation of the hydrosilylation product, 1-phenyl-1-(trichlorosilyl)ethane (4a). The palladium complex of 2g also efficiently catalyzed the asymmetric hydrosilylation of substituted styrenes on the phenyl ring or at the beta position to give the corresponding chiral benzylic alcohols of over 96% ee. Deuterium-labeling studies on the hydrosilylation of regiospecifically deuterated styrene revealed that P-hydrogen elimination from l-phenylethyl(silyl)palladium intermediate is very fast compared with reductive elimination giving hydrosilylation product when ligand 2g is used. The reaction of o-allylstyrene (9) with trichlorosilane catalyzed by (R)-2g/Pd gave (1S,2R)-1-methyl-2-(trichlorosilylmethyl)indan (10) (91% ee) and (S)-1-(2-(propenyl)phenyl)-1-trichlorosilylethanes (11a and 11b) (95% ee). On the basis of their opposite configurations at the benzylic position, a rationale for the high enantioselectivity of ligand 2g is proposed.

  DOI：

  10.1021/jo001614p
• 作为产物：
  描述：

  甲基苯甲醇-D1 在 碘 作用下， 生成 苯乙烯-Alpha-d1
  参考文献：
  名称：

  α-和β-氘代苯乙烯聚合物的热解

  摘要：

  近来加聚物的解聚已经从四个基本反应的角度进行了处理：引发、增长、转移和终止；类似于在聚合过程中进行的那些反应。根据其相对重要性，正是转移过程导致聚合物在单体产率、速率与转化率行为以及分子量与转化率行为方面的差异。假设转移过程是通过自由基从聚合物链中提取氢来进行的。通过在聚合物链中的选定点用氘代替氢，由于同位素效应，转移过程的量应该减少。两种氘代聚合物由α-和β-氘代苯乙烯制成，并研究了它们的解聚行为。在α-氘代苯乙烯聚合物的情况下，结果与转移过程速率的1/2降低以及传播速率的增加相一致。β-聚合物的结果意味着转移和传播速率的增加。获得的数据表明，在聚苯乙烯中，分子间转移过程是解聚过程中聚合物残留物分子量下降的主要原因。

  DOI：

  10.1002/pol.1955.120157913

文献信息

• Pyrolysis of Sulfoxide Bearing Electron-Withdrawing Substituents on β-Position in<i>S</i>-Ethyl Group of Ethyl Phenyl Sulfoxide
  作者：Toshiaki Yoshimura、Masaki Yoshizawa、Eiichi Tsukurimichi

  DOI：10.1246/bcsj.60.2491

  日期：1987.7

  In order to obtain information concerning the reaction mechanism of the pyrolysis of a sulfoxide bearing an electron-withdrawing substituent on the β-position in the S-ethyl group of ethyl phenyl sulfoxide, 2-(substituted phenyl)ethyl aryl sulfoxides(1) and 2-cyanoethyl (substituted phenyl) sulfoxides(2) were pyrolyzed. The rate-enhancing effect of the β-phenyl group of 1 was small. The activation

  为了获得有关在乙基苯基亚砜的 S-乙基基团的 β-位上带有吸电子取代基的亚砜热解反应机理的信息，2-（取代苯基）乙基芳基亚砜（1）和2-氰乙基（取代苯基）亚砜（2）被热解。1的β-苯基基团的速率增强效果很小。发现 1 的活化焓和熵分别为 110 kJ mol-1 和 -45 JK-1 mol-1。1 的哈米特图给出了取代基的正趋势，在 β-苯基 (ρ=0.76) 和 S-苯基 (ρ=0.32) 上，尽管后者的 ρ 值约为前者的一半. 另一方面，2 的哈米特图没有给出一条直线，但是一个凹曲线，其中从 p-OCH3 到 p-Cl 基团的一系列取代基呈现负趋势（ρ=-0.49），而 p-NO2 基团呈现正趋势。发现 2 的热解速率在 100 °C 时比 1 的热解速率快约 23 倍。这 ...
• On the Mechanism of the Copper-Catalyzed Cyclopropanation Reaction
  作者：Torben Rasmussen、Jakob F. Jensen、Niels Østergaard、David Tanner、Tom Ziegler、Per-Ola Norrby

  DOI：10.1002/1521-3765(20020104)8:1<177::aid-chem177>3.0.co;2-h

  日期：2002.1.4

  addition of the very reactive metallacarbene intermediate in an early transition state to the substrate alkene is concerted but strongly asynchronous, with substantial cationic character on one alkene carbon in the neighborhood of the transition state. Evidence from isotope effects and Hammett studies supports the nature of the transition state. Formation of a metallacyclobutane intermediate by a [2+2] addition

  通过实验和计算方法研究了重氮对映选择性铜催化的环丙烷化反应中的选择性决定步骤。处于早期过渡态的反应性很强的金属茂碳烯中间体向底物烯烃的添加是一致的，但强烈不同步，在过渡态附近的一个烯烃碳上具有实质性的阳离子特性。同位素效应和Hammett研究的证据支持过渡态的性质。在动力学上不利于通过添加[2 + 2]形成金属环丁烷中间体。已经鉴定出影响对映体和非对映体选择性的配体-底物相互作用，并且建议在添加过程中烯烃底物的优选取向。
• Isotopic probes for ruthenium-catalyzed olefin metathesis
  作者：Justin A. M. Lummiss、Adrian G. G. Botti、Deryn E. Fogg

  DOI：10.1039/c4cy01118j

  日期：——

  ¹³C-labelled Grubbs catalysts, RuCl₂(L)(PCy₃)(¹³CHR) (R = H, Ph), pinpoint the fate of the methylidene (benzylidene) moiety during metathesis and deactivation.

  ¹³C标记的Grubbs催化剂，RuCl₂(L)(PCy₃)(¹³CHR) (R = H, Ph)，揭示了甲基亚甲基（苄亚甲基）基团在醇醚反应和失活过程中的命运。
• Catalytic α-Selective Deuteration of Styrene Derivatives
  作者：Thomas R. Puleo、Alivia J. Strong、Jeffrey S. Bandar

  DOI：10.1021/jacs.8b12874

  日期：2019.1.30

  We report an operationally simple protocol for the catalytic α-deuteration of styrenes. This process proceeds via the base-catalyzed reversible addition of methanol to styrenes in DMSO -d6 solvent. The concentration of methanol is shown to be critical for high yields and selectivities over multiple competing side reactions. The synthetic utility of α-deuterated styrenes for accessing deuterium-labeled

  我们报告了一个操作简单的苯乙烯催化 α-氘化协议。该过程通过碱催化将甲醇可逆加成到 DMSO -d6 溶剂中的苯乙烯中进行。甲醇的浓度显示出对于多个竞争副反应的高产率和选择性至关重要。证明了 α-氘代苯乙烯在获取氘标记的手性苄基立体中心方面的合成效用。
• Mechanism of Catalytic Oxidation of Styrenes with Hydrogen Peroxide in the Presence of Cationic Palladium(II) Complexes
  作者：Katherine L. Walker、Laura M. Dornan、Richard N. Zare、Robert M. Waymouth、Mark J. Muldoon

  DOI：10.1021/jacs.7b05413

  日期：2017.9.13

  Kinetic studies, isotope labeling, and in situ high-resolution mass spectrometry are used to elucidate the mechanism for the catalytic oxidation of styrenes using aqueous hydrogen peroxide (H2O2) and the cationic palladium(II) compound, [(PBO)Pd(NCMe)2][OTf]2 (PBO = 2-(pyridin-2-yl)benzoxazole). Previous studies have shown that this reaction yields acetophenones with high selectivity. We find that

  动力学研究、同位素标记和原位高分辨率质谱用于阐明使用过氧化氢 (H2O2) 水溶液和阳离子钯 (II) 化合物 [(PBO)Pd(NCMe) 催化氧化苯乙烯的机制2][OTf]2 (PBO = 2-(吡啶-2-基)苯并恶唑)。先前的研究表明，该反应可以高选择性地产生苯乙酮。我们发现 H2O2 与 Pd(II) 结合，然后与苯乙烯结合以生成 Pd-烷基过氧化物，该过氧化物至少通过两个竞争过程释放苯乙酮，其中一个过程涉及钯烯醇化物中间体，此前在烯烃氧化反应中未观察到该中间体。我们建议苯乙酮是由钯烯醇中间体通过 H2O2 质子化形成的。我们用叔丁基过氧化氢代替过氧化氢，发现，