苯甲醛-α-d1 | 3592-47-0

• 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: 苯甲醛-α-d1
• 中文别名: 苯甲醛-d{1}；苯甲醛-D{1}；苯甲醛-d
• 英文名称: Benzaldehyde-d
• 英文别名: benzaldehyde-α-d₁；benzaldehyde-d1；Deuterio(phenyl)methanone
• CAS: 3592-47-0
• 化学式: C₇H₆O
• 分子量: 107.116
• InChiKey: HUMNYLRZRPPJDN-RAMDWTOOSA-N

物化性质

• 熔点：
  −26 °C(lit.)
• 沸点：
  178-179 °C(lit.)
• 密度：
  1.055 g/mL at 25 °C
• 闪点：
  145 °F(lit.)
• 溶解度：
  丙酮（少量溶解）
• 稳定性/保质期：
  避免强氧化剂、强还原剂及强碱。

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• WGK Germany：
  3
• 储存条件：
  密封保存于阴凉避光处

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
: Benzaldehyde-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. : 3592-47-0

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SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Acute toxicity, Oral (Category 4), H302
Acute toxicity, Dermal (Category 4), H312
Skin irritation (Category 2), H315
Respiratory sensitisation (Category 1), H334
Skin sensitisation (Category 1), H317
For the full text of the H-Statements mentioned in this Section, see Section 16.
Not a hazardous substance or mixture according to EC-directives 67/548/EEC or 1999/45/EC.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Danger
Hazard statement(s)
Harmful if swallowed.
Harmful in contact with skin.
Causes skin irritation.
May cause an allergic skin reaction.
May cause allergy or asthma symptoms or breathing difficulties if inhaled.
Precautionary statement(s)
Avoid breathing vapours.
Wear protective gloves/ protective clothing.
P342 + P311 If experiencing respiratory symptoms: Call a POISON CENTER or doctor/
physician.
Supplemental Hazard none
Statements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Chemical characterization : Isotopically labeled
Synonyms : Benz(aldehyde-d)
Formula : C7DH5O
Molecular Weight : 107,13 g/mol
CAS-No. : 3592-47-0
No components need to be disclosed according to the applicable regulations.
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
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. Evacuate personnel to safe areas. 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)
Apart 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, 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: -26 °C - lit.
point
f) Initial boiling point and 178 - 179 °C - lit.
boiling range
g) Flash point 64,00 °C - closed cup
h) Evapouration rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower Upper explosion limit: 8,50 %(V)
flammability or Lower explosion limit: 1,40 %(V)
explosive limits
k) Vapour pressure 5 hPa at 45,00 °C
l) Vapour density no data available
m) Relative density 1,055 g/mL at 25 °C1,055 g/cm3 at 25 °C
n) Water solubility no data available
o) Partition coefficient: n- log Pow: 1,500
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
Strong oxidizing agents, Strong reducing agents, Strong bases, Alkali metals, Aluminium, Iron, phenols,
Oxygen
Hazardous 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
LD50 Oral - rat - 1.300 mg/kg
Remarks: Behavioral:Somnolence (general depressed activity). Behavioral:Coma.
LD50 Dermal - rabbit - 1.250 mg/kg
Skin corrosion/irritation
Skin - rabbit
Result: Skin irritation - 24,00 h
Serious eye damage/eye irritation
Eyes - rabbit
Result: Mild eye irritation
Respiratory or skin sensitisation
Germ cell mutagenicity
Carcinogenicity
This product is or contains a component that is not classifiable as to its carcinogenicity based on its IARC,
ACGIH, NTP, or EPA classification.
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
Toxicity to fish LC50 - Lepomis macrochirus - 1,07 mg/l - 96,0 h
LOEC - Pimephales promelas (fathead minnow) - 0,45 mg/l - 7,0 d
NOEC - Pimephales promelas (fathead minnow) - 0,22 mg/l - 7,0 d
LC50 - Leuciscus idus (Golden orfe) - 62 mg/l - 48,0 h
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
Toxic to aquatic life.
no data available

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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: 1990 IMDG: 1990 IATA: 1990
UN proper shipping name
ADR/RID: BENZALDEHYDE
IMDG: BENZALDEHYDE
IATA: Benzaldehyde
Transport hazard class(es)
ADR/RID: 9 IMDG: 9 IATA: 9
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

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  苯甲醛-α-d1 在 盐酸 、 过氧化苯甲酸叔丁酯 、 eosin Y disodium salt 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 反应 26.0h， 生成 二苯甲酰基甲烷
  参考文献：
  名称：

  通过无过渡金属的光氧化还原催化烯类与醛的区域和立体选择性C（sp2）–H酰化

  摘要：

  通过无过渡金属的光氧化还原催化，证明了酰胺与醛的直接，有效的C（sp 2）-H酰化反应。转化过程顺利进行，在温和条件下不诉诸昂贵且可能有毒的铱或钌多吡啶基光催化剂，以立体选择性和区域选择性方式提供了多种合成关键的，几何定义的β-酰化酰胺。

  DOI：

  10.1039/d0gc01947j
• 作为产物：
  描述：

  benzyl alcohol-d1 在 (NH₄)₄[CuMo₆O₁₈(OH)₆]·5H₂O 、 氧气 、 sodium chloride 作用下， 以 水 、 乙腈 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 生成 苯甲醛-α-d1
  参考文献：
  名称：

  无机配体负载的铜催化高效高效地进行酒精的好氧氧化

  摘要：

  醇氧化为醛或酮对于制药和精细化学工业以及生物质转化而言是高度相关的转化，并且通常使用化学计量的高度危险的氧化剂进行。先前使用过渡金属络合物催化剂对醇进行好氧氧化需要复杂的有机配体和/或硝酰基自由基作为助催化剂。在这里，我们报告了一种高效且环保的方法，可使用无机配体负载的铜催化剂1（NH 4）4 [CuMo 6 O 18（OH）6 ]和O 2（1 atm ）来促进醇的需氧氧化）作为唯一的氧化剂。催化剂1它是由廉价且普遍使用的（NH 4）6 Mo 7 O 24 ·4H 2 O和CuSO 4直接合成的，CuSO 4由纯的无机骨架组成，该骨架由中心的Cu II核构建而成，并由六个Mo VI O 6无机支架支撑。铜催化剂1在醇的催化氧化中对多种底物表现出优异的选择性和活性，并且可以避免使用有毒的氧化剂，硝酰基自由基以及潜在的对空气/湿气敏感的复杂的有机配体，而这些配体是不可商购的。由于其坚固的无机骨

  DOI：

  10.1039/c9gc01248f
• 作为试剂：
  描述：

  叔丁基过氧化氢 在 苯甲醛-α-d1 、 4,4'-二溴-2,2'-联吡啶 、 copper(l) chloride 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 氘代叔丁醇
  参考文献：
  名称：

  铜通过分子内自由基级联酰基氰化反应合成含CN的苯并二氢吡喃-4-酮

  摘要：

  已经开发了铜催化的分子内自由基级联酰基氰化以合成含氰基的chroman-4-ones。使用绿色氰基源，在温和的条件下，可以中等到良好的产率制备一系列CN取代的chroman-4-one衍生物。对照实验表明该反应涉及分子内酰基自由基加成/氰化过程。此外，该协议具有步长和原子经济性，将氰基引入到chroman-4-one中引起了极大的兴趣和重要性。

  DOI：

  10.1016/j.tetlet.2021.153061

文献信息

• Regiochemistry of mercury(II) oxide oxidation of unsymmetrical N,N-disubstituted hydroxylamines
  作者：Sk.Asrof Ali、S.M. Azhar Hashmi、Mohammad N. Siddiqui、Mohammed I.M. Wazeer

  DOI：10.1016/0040-4020(96)00904-0

  日期：1996.11

  Mercury(II) oxide oxidation of N,N-disubstituted hydroxylamines with the α and α′ carbon atoms containing one and two hydrogen atoms, respectively, gave aldonitrones in a highly regioselective manner. Removal of the α proton is involved in the rate determining step as shown by primary kinetic isotope effect.

  N，N-二取代的羟胺分别被具有一个和两个氢原子的α和α'碳原子氧化的汞（II）氧化，以高度区域选择性的方式生成醛亚硝酮。如初生动力学同位素效应所示，速率确定步骤涉及α质子的去除。
• On the mechanism and synthetic applications of the thermal and alkaline degradation of c-18 castor oil
  作者：S. Ranganathan、Raaj Kumar、V. Maniktala

  DOI：10.1016/s0040-4020(01)99322-6

  日期：1984.1

  c-8 via unique sequence involving a primary reaction which is associated with three different types of redox systems as well as with uncoupled oxidation, the overall change amounting to a milieu of hydride transfer, π -migration, retro-Michael, retro-aldol, Meerwein-Pondorff-Verley as well as Cannizzaro type of reactions. These findings which constitute the core of the present work, are of significance

  由π蓖麻油片段的C-18骨架，热至C-11 + C-7 2 S +π 2 S +Ò 2s过程，并通过独特的顺序将热碱转化为c-10 + c-8，该过程涉及与三种不同类型的氧化还原系统以及未偶联的氧化有关的主要反应，总体变化相当于氢化物转移的环境π -迁移，迈克·怀特（Michael），怀特·阿尔多（Retro-aldol），Meerwein-Pondorff-Verley以及Cannizzaro型反应。这些发现构成了本研究的核心，不仅对于了解蓖麻油的两个最重要的反应具有重要意义，而且在利用这些知识来引导和优化所需产品方面也具有重要意义。此外，它们为机械有机化学增加了一个独特的方面。蓖麻油C-18→C-11 + C-7变化的协调性质的令人信服的证据是，将12-羟基十八烷基9-壬酸甲酯干净地转化为新型有用的烯丙基酯，十一碳烯酸9,10-讨人喜欢。对不同的α-取代的γδ-不饱和醇进行的模型研究表明，π2个S
• Kinetics of C(2α)-Proton Abstraction from 2-Benzylthiazolium Salts Leading to Enamines Relevant to Catalysis by Thiamin-Dependent Enzymes
  作者：Gabriel L. Barletta、Yu Zou、W. Phillip Huskey、Frank Jordan

  DOI：10.1021/ja9633528

  日期：1997.3.1

  kinetics of proton transfer from the C(2α) position of 2-(1-methoxybenzyl)thiazolium salts was studied for the p-H and p-N(CH3)3+ derivatives as models for the protonation of the enamine/C(2α)-carbanion, a key intermediate in many thiamin diphosphate-dependent enzymatic reactions. The reactions were studied by rapid mixing of the salts with sodium hydroxide in a stopped-flow instrument while monitoring the

  研究了从 2-(1-甲氧基苄基)噻唑鎓盐的 C(2α) 位置的质子转移动力学，研究 pH 值和 pN(CH3)3+ 衍生物作为烯胺/C(2α)-碳负离子质子化的模型，许多硫胺二磷酸依赖性酶促反应的关键中间体。通过在停流仪器中将盐与氢氧化钠快速混合，同时在光谱的可见光区域监测烯胺形成和分解的进程来研究反应。结果表明，在实验条件下，噻唑鎓环开环得到产物，其特征 1H-NMR 谱与开环中生成的酰胺键的顺式和反式立体化学一致。对三甲基铵取代的化合物 (1) 的进程曲线分析得出以下速率常数 (25 °C)：21 M-1 s-1 用于 C(2α) 的去质子化，300-540 s-1 用于再质子化和 3.4 M-1 s-1 用于噻唑鎓开环。对于未取代的共...
• Phenazinium Salt-Catalyzed Aerobic Oxidative Amidation of Aromatic Aldehydes
  作者：Dasheng Leow

  DOI：10.1021/ol5029354

  日期：2014.11.7

  Amides are prevalent in organic synthesis. Developing an efficient synthesis that avoids expensive oxidants and heating is highly desirable. Here the oxidative amidation of aromatic aldehydes is reported using an inexpensive metal-free visible light photocatalyst, phenazine ethosulfate, at low catalytic loading (1–2 mol %). The reaction proceeds at ambient temperature and uses air as the sole oxidant

  酰胺在有机合成中很普遍。非常需要开发一种避免昂贵的氧化剂和加热的有效合成方法。在此报道了使用廉价的无金属可见光光催化剂吩嗪乙硫酸盐在低催化负荷（1-2摩尔％）下芳族醛的氧化酰胺化反应。反应在环境温度下进行，并使用空气作为唯一的氧化剂。操作简便的程序为形成酰胺键提供了一种经济，绿色和温和的替代方法。
• Heterogeneous carbon nitride photocatalyst for C–C bond oxidative cleavage of vicinal diols in aerobic micellar medium
  作者：Tengfei Niu、Shengjun Chen、Mei Hong、Tianhao Zhang、Jiayang Chen、Xinyu Dong、Bangqing Ni

  DOI：10.1039/d0gc01727b

  日期：——

  A green and efficient visible-light promoted aerobic oxidative C–C bond cleavage of vicinal diols in micellar medium has been developed. This protocol used graphitic carbon nitride with nitrogen vacancies (CN620) as a metal-free recyclable photocatalyst and CTAB as surfactant in water. Control experiments and the ESR results indicated that superoxide radicals and valence band holes played an important

  已经开发了绿色高效的可见光促进胶束介质中邻二醇的好氧氧化C–C键裂解。该协议使用具有氮空位的石墨氮化碳（CN620）作为无金属可循环使用的光催化剂，而CTAB作为水中的表面活性剂。对照实验和ESR结果表明，超氧自由基和价带孔在反应中起重要作用。进一步的同位素实验提出了反应的β-分裂/ HAT途径和氧化/水解/脱水途径，这与以前的报道不同。半导体/胶束催化剂体系可以循环使用至少10次，而不会显着降低活性。此外，