乙醛-D1 | 4122-13-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 乙醛-D1
• 中文别名: 氘代乙醛；乙醛-D1氘代内标
• 英文名称: 1-deuterio-acetaldehyde
• 英文别名: acetaldehyde-d1；acetaldehyde-1-d1；(1-2H1)Acetaldehyde；1-deuterioethanone
• CAS: 4122-13-8
• 化学式: C₂H₄O
• 分子量: 45.0452
• InChiKey: IKHGUXGNUITLKF-VMNATFBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  3
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

SDS

Version 1.2
Regulation (EC) No 1907/2006

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1 - Product and Company Information

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Product Name ACET(ALDEHYDE-D) 98+ ATOM % D

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2 - Hazards Identification

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SPECIAL INDICATION OF HAZARDS TO HUMANS AND THE ENVIRONMENT
May cause cancer. May cause heritable genetic damage. Extremely
flammable. Harmful by inhalation, in contact with skin and if
swallowed. Irritating to eyes, respiratory system and skin.

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3 - Composition/Information on Ingredients

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Product Name CAS # EC no Annex I
Index Number
ACET(ALDEHYDE-D) 98+ ATOM % D 4122-13-8 223-921-1 None
Formula C2H3DO
Molecular Weight 45,0600 AMU

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4 - First Aid Measures

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AFTER INHALATION
If inhaled, remove to fresh air. If not breathing give
artificial respiration. If breathing is difficult, give oxygen.
AFTER INGESTION
If swallowed, wash out mouth with water provided person is
conscious. Call a physician.

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5 - Fire Fighting Measures

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EXTINGUISHING MEDIA
Suitable: For small (incipient) fires, use media such as
"alcohol" foam, dry chemical, or carbon dioxide. For large
fires, apply water from as far as possible. Use very large
quantities (flooding) of water applied as a mist or spray; solid
streams of water may be ineffective. Cool all affected
containers with flooding quantities of water.
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SPECIAL RISKS
Specific Hazard(s): Extremely flammable. Vapor may travel
considerable distance to source of ignition and flash back.
Explosion Hazards: Vapor may travel considerable distance to
source of ignition and flash back.
SPECIAL PROTECTIVE EQUIPMENT FOR FIREFIGHTERS
Wear self-contained breathing apparatus and protective clothing
to prevent contact with skin and eyes.

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6 - Accidental Release Measures

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PERSONAL PRECAUTION PROCEDURES TO BE FOLLOWED IN CASE OF LEAK OR SPILL
Shut off all sources of ignition. Evacuate area.
METHODS FOR CLEANING UP
Cover with an activated carbon adsorbent, take up and place in
closed containers. Transport outdoors.

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7 - Handling and Storage

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HANDLING
Directions for Safe Handling: Do not breathe vapor. Avoid
contact with eyes, skin, and clothing. Avoid prolonged or
repeated exposure.
STORAGE
Conditions of Storage: Keep tightly closed. Keep away from heat
and open flame. Store under nitrogen.
Unsuitable: Forms explosive peroxides on prolonged storage
Store at -20°C
SPECIAL REQUIREMENTS: May develop pressure. Open carefully. Air
sensitive.

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8 - Exposure Controls / Personal Protection

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ENGINEERING CONTROLS
Use only in a chemical fume hood. Safety shower and eye bath.
GENERAL HYGIENE MEASURES
Wash contaminated clothing before reuse. Wash thoroughly after
handling.
PERSONAL PROTECTIVE EQUIPMENT
Special Protective Measures: Wear appropriate government approved
respirator, chemical-resistant gloves, safety goggles, other
protective clothing.

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9 - Physical and Chemical Properties

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pH N/A
BP/BP Range 20,000. - 21,000 °C.760,000 mmHg
MP/MP Range N/A
Flash Point - 27,000 °C. Method: closed cup
Flammability N/A
Autoignition Temp N/A
Oxidizing Properties N/A
Explosive Properties N/A
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Explosion Limits N/A
Vapor Pressure 707,256000000 mmHg 20,00 °C
SG/Density 0,8060 g/cm3
Partition Coefficient N/A
Viscosity N/A
Vapor Density N/A
Saturated Vapor Conc. N/A
Evaporation Rate N/A
Bulk Density N/A
Decomposition Temp. N/A
Solvent Content N/A
Water Content N/A
Surface Tension N/A
Conductivity N/A
Miscellaneous Data N/A
Solubility N/A

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10 - Stability and Reactivity

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STABILITY
Conditions of Instability: May decompose on exposure to air.
Materials to Avoid: Strong acids, Oxidizing agents, Reducing
agents, Strong bases.
HAZARDOUS DECOMPOSITION PRODUCTS
Hazardous Decomposition Products: Carbon monoxide, Carbon dioxide.

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11 - Toxicological Information

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SENSITIZATION
Sensitization: May cause allergic reaction.
SIGNS AND SYMPTOMS OF EXPOSURE
Pulmonary edema. Effects may be delayed. Dermatitis. Nausea,
headache, and vomiting. Exposure can cause: Symptoms of exposure
may include burning sensation, coughing, wheezing, laryngitis,
shortness of breath, headache, nausea, and vomiting.
ROUTE OF EXPOSURE
Eye Contact: Causes severe eye irritation.
Inhalation: Material is irritating to mucous membranes and upper
respiratory tract.
Multiple Routes: Harmful if swallowed, inhaled, or absorbed
through skin.
TARGET ORGAN INFORMATION
Central nervous system. Blood. Lungs. Kidneys. Liver.
CHRONIC EXPOSURE - CARCINOGEN
Result: Carcinogen.
CHRONIC EXPOSURE - REPRODUCTIVE HAZARD
Result: Overexposure may cause reproductive disorder(s) based on
tests with laboratory animals.

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12 - Ecological Information

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No data available.

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13 - Disposal Considerations
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SUBSTANCE DISPOSAL
Burn in a chemical incinerator equipped with an afterburner and
scrubber but exert extra care in igniting as this material is
highly flammable. Observe all federal, state, and local
environmental regulations.

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14 - Transport Information

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RID/ADR
UN#: 1089
Class: 3
PG: I
Proper Shipping Name: Acetaldehyde
IMDG
UN#: 1089
Class: 3
PG: I
Proper Shipping Name: Acetaldehyde
Marine Pollutant: No
Severe Marine Pollutant: No
IATA
UN#: 1089
Class: 3
PG: I
Proper Shipping Name: Acetaldehyde
Inhalation Packing Group I: No

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15 - Regulatory Information

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CLASSIFICATION AND LABELING ACCORDING TO EU DIRECTIVES
INDICATION OF DANGER: F+-T
Extremely Flammable. Toxic.
R-PHRASES: 45-46-12-20/21/22-36/37/38
May cause cancer. May cause heritable genetic damage. Extremely
flammable. Harmful by inhalation, in contact with skin and if
swallowed. Irritating to eyes, respiratory system and skin.
S-PHRASES: 53-16-26-36/37/39-45
Avoid exposure - obtain special instructions before use. Keep
away from sources of ignition - no smoking. In case of contact
with eyes, rinse immediately with plenty of water and seek
medical advice. Wear suitable protective clothing, gloves, and
eye/face protection. In case of accident or if you feel unwell,
seek medical advice immediately (show the label where possible).
COUNTRY SPECIFIC INFORMATION
Germany
WGK: 3
Self-Classification

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16 - Other Information

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WARRANTY
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
SIGMA www.molbase.com
appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Inc.,
shall not be held liable for any damage resulting from handling or
from contact with the above product. See reverse side of invoice
or packing slip for additional terms and conditions of sale.
Copyright 2010 Co. License granted to make
unlimitedpaper copies for internal use only.
DISCLAIMER
For R&D use only. Not for drug, household or other uses.
SIGMA www.molbase.com

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  乙醛-D1 在 氯 作用下， 24.85 ℃ 、101.3 kPa 条件下， 反应 0.36h， 生成 acetyl radical
  参考文献：
  名称：

  F、Cl和Br与甲醛和乙醛反应的实验和理论研究

  摘要：

  甲醛、甲醛-d2、13C-甲醛、乙醛、乙醛-1-d1、乙醛-2,2,2-d3和乙醛-d4与Cl和Br原子在298±2 K和1013±10 hPa 使用长路径 FTIR 检测。对于甲醛，观察到的唯一产物是 HCl、HBr 和 CO；对于乙醛，产物分布表明存在一个主要通道：CH3CHO+X→CH3CO+HX。298 K下的动力学同位素效应由相对速率法确定：kCl+HCHO/kCl+DCDO=1.302±0.014，kCl+H13CHO/kCl+DCDO=1.217±0.025，kBr+HCHO/kBr+DCDO=7.5± 0.4和kBr+H13CHO/kBr+DCDO=6.8±0.4，kCl+CH3CHO/kCl+CH3CDO=1.343±0.023，kCl+CH3CHO/kCl+CD3CDO=1.323±0.018，kCl+CD3CHO/kCl+CH3CDO=1.345±0.015， kCl

  DOI：

  10.1039/b004546m
• 作为产物：
  描述：

  O-d-ethenol 在 重水 作用下， 生成 乙醛-D1
  参考文献：
  名称：

  热力学不稳定物种的化学研究。乙醛烯醇互变异构体乙烯醇的直接聚合

  摘要：

  乙烯醇是通过乙烯酮甲基乙烯基乙缩醛 I 的水解生成的。 一般来说，我们观察到在室温下将 0.9 mol 当量的 I 添加到 1% (v/v) D[sub 2]O 的丙酮-d 溶液中[sub 6]，使得整个溶液在 DCl 中的浓度为 10[sup [minus]4]M，产生 90% OD 乙烯醇，其在环境温度下仅非常缓慢地互变异构化为乙醛 (k[sub t] [大约] 10[sup [minus]6] M/s，见下文）。剩余的 10% 的 I 被转化为醋酸乙烯酯（水解过程中的副产物），以及来自互变异构化的少量乙醛。乙烯醇的光谱数据与先前报告的数据相同。我们的观察表明，产生持久性乙烯醇溶液的关键是通过在快速水解步骤中使用接近化学计量量的水将系统推向无水状态。通过利用稳定的电子供体-受体相互作用，OD乙烯醇和马来酸酐的自由基共聚被证明是成功的。在马来酸酐和乙烯醇中，聚合被确定为一级。由于在该条件

  DOI：

  10.1021/ja00088a051
• 作为试剂：
  描述：

  丙炔醛 在 吡啶 、 氘氧化钠 、 乙醛-D1 、 五氯化磷 作用下， 生成 1-D-3,3-dichloro-1-propyne
  参考文献：
  名称：

  Chlorovinylidenecarbene: generation from 3,3-dichloropropyne by interaction with potassium hydroxide under phase-transfer catalysis conditions and reactions with alkenes

  摘要：

  Chlorination of propargyl aldehyde with PCI5 in CH2Cl2 at -20-degrees-C the presence of catalytic amounts of pyridine afforded dichloromethylacetylene. Reaction of the latter with powdered KOH under phase-transfer catalysis conditions gave chlorovinylidenecarbene due to gamma-elimination of HCl. In the presence of alkenes the carbene undergoes addition at the double bond giving chlorovinylidenecyclopropanes in 20-45 % yields.

  DOI：

  10.1007/bf00702002

文献信息

• Oxidation of N-Nitrosoalkylamines by Human Cytochrome P450 2A6
  作者：Goutam Chowdhury、M. Wade Calcutt、F. Peter Guengerich

  DOI：10.1074/jbc.m109.088039

  日期：2010.3

  Cytochrome P450 (P450) 2A6 activates nitrosamines, including N,N-dimethylnitrosamine (DMN) and N,N-diethylnitrosamine (DEN), to alkyl diazohydroxides (which are DNA-alkylating agents) and also aldehydes (HCHO from DMN and CH(3)CHO from DEN). The N-dealkylation of DMN had a high intrinsic kinetic deuterium isotope effect ((D)k(app) approximately 10), which was highly expressed in a variety of competitive

  细胞色素 P450 (P450) 2A6 将亚硝胺，包括 N,N-二甲基亚硝胺 (DMN) 和 N,N-二乙基亚硝胺 (DEN) 激活为烷基重氮氧化物（它们是 DNA 烷基化剂）和醛（来自 DMN 和 CH(3 )CHO 来自 DEN)。DMN 的 N-脱烷基化具有很高的固有动力学氘同位素效应（(D)k(app) 约 10），这在各种竞争性和非竞争性实验中得到了高度表达。DEN 的 (D)k(app) 约为 3，在非竞争性实验中未表达。DMN 和 DEN 也分别被氧化为 HCO(2)H 和 CH(3)CO(2)H。在这两种情况下都没有观察到滞后，考虑到测量 DMN 和 DEN 氧化成醛和醛氧化成羧酸的 k(cat) 和 K(m) 参数，这是出乎意料的。光谱分析没有表明醛对 P450 2A6 有很强的亲和力，但脉冲追踪实验表明，在 DMN 和 DEN 氧化成羧酸的过程中，与添加的（未标记的）醛只有有限的交换。在
• Stereochemistry and mechanism of the reverse ene reaction of cis-2-alkyl-1-alkenylcyclobutanes. Stereoelectronic control in a system showing marginal energetic benefit of concert
  作者：Stephen J. Getty、Jerome A. Berson

  DOI：10.1021/ja00012a033

  日期：1991.6

  racemic cyclobutanes (1RS,2RS,1'SR)-1-(1-methoxyethyl)-2-vinylcyclobutane (16b) and (1SR,2SR,1'SR)-1-(1-methoxyethyl)-2-vinylcyclobutane (17b) each undergo a sigmatropic hydrogen shift (reverse ene reaction) amounting to about 18% of the total pyrolysis product, in addition to four other unimolecular processes

  在 243.8-267.5 °C 温度范围内，外消旋环丁烷 (1RS,2RS,1'SR)-1-(1-甲氧基乙基)-2-乙烯基环丁烷 (16b) 和 (1SR,2SR,1'SR)-1- (1-甲氧基乙基)-2-乙烯基环丁烷 (17b) 除了四个其他单分子过程外，每个都经历了一个 σ 氢位移（逆烯反应），约占总热解产物的 18%
• Preparation of human drug metabolites using fungal peroxygenases
  作者：Marzena Poraj-Kobielska、Matthias Kinne、René Ullrich、Katrin Scheibner、Gernot Kayser、Kenneth E. Hammel、Martin Hofrichter

  DOI：10.1016/j.bcp.2011.06.020

  日期：2011.10

  organic chemists. Here we report that aromatic peroxygenases (APOs; EC 1.11.2.1) secreted by the agaric fungi Agrocybe aegerita and Coprinellus radians catalyzed the H(2)O(2)-dependent selective monooxygenation of diverse drugs, including acetanilide, dextrorphan, ibuprofen, naproxen, phenacetin, sildenafil and tolbutamide. Reactions included the hydroxylation of aromatic rings and aliphatic side chains

  通过选择性单加氧合成羟基化和O-或N-去烷基化的人类药物代谢产物（HDM）对于合成有机化学家而言仍然是一项艰巨的任务。在这里我们报告说，由琼脂真菌Agrocybe aegerita和Coprinellus radians分泌的芳香过氧化物酶（APOs; EC 1.11.2.1）催化H（2）O（2）依赖的选择性单氧合作用的多种药物，包括对乙酰苯胺，右旋糖酐，布洛芬，萘普生，非那西丁，西地那非和甲苯磺丁酰胺。反应包括芳环和脂族侧链的羟基化，以及O-和N-脱烷基，根据所使用的特定APO表现出不同的区域选择性。充其量，可以以大于80％的产率和高达99％的异构体纯度获得所需的HDM。甲苯磺丁酰胺的氧化，乙苯胺和卡马西平在H（2）（1）（8）O（2）的存在下导致（1）（8）O几乎完全掺入相应的产物中，因此确定这些反应是过氧化反应。非那西丁-d（1）的脱乙基显示观察到的分子内氘同位素效应[（k（H）/ k（D））（obs）]为3
• Kinetics and mechanism of the oxidation of aliphatic aldehydes by tetrabutylammonium tribromide
  作者：Manju Baghmar、Pradeep K. Sharma

  DOI：10.1002/kin.1033

  日期：2001.6

  The oxidation of six aliphatic aldehydes by tetrabutylammonium tribromide (TBATB) in aqueous acetic acid resulted in the formation of corresponding carboxylic acids. The reaction is first order with respect to TBATB and the aldehydes. The oxidation of deuteriated acetaldehyde (MeCDO) showed the presence of substantial kinetic isotope effect (kH/kD = 5.92 at 298 K). Addition of tetrabutylammonium chloride

  三溴化四丁基铵 (TBATB) 在乙酸水溶液中氧化六种脂肪醛，形成相应的羧酸。就 TBATB 和醛而言，该反应是一级反应。氘化乙醛 (MeCDO) 的氧化表明存在显着的动力学同位素效应 (kH/kD = 5.92 at 298 K)。添加四丁基氯化铵对反应速率没有影响。已提出三溴化物离子作为活性氧化物质。速率常数与 Taft 的 σ* 值密切相关，反应常数为负。已经提出了在速率确定步骤中涉及氢化物离子从醛水合物转移到氧化剂的机制。© 2001 John Wiley & Sons, Inc. Int J Chem Kinet 33: 390–395, 2001
• Metal Ions Do Not Play a Direct Role in the Formation of Carbon-Carbon Triple Bonds during Reduction of Trihaloalkyls by Cr^IIor V^II
  作者：Ophir Levy、Avi Bino

  DOI：10.1002/chem.201202918

  日期：2012.12.7

  aqueous solutions yield alkynes and other products. Stepwise halogen abstractions from the trihaloalkyls form alkyl carbyne triradicals in solution. These radicals undergo coupling reactions, producing triply bonded alkyne molecules (see scheme). This process is not metal‐assisted and does not occur in the coordination sphere of the metal ions.

  卡宾基：水溶液中三卤代烷基化合物与Cr 2+或V 2+的反应生成炔烃和其他产物。从三卤代烷基逐步提取卤素在溶液中形成烷基卡宾三基。这些自由基进行偶联反应，生成三键结合的炔烃分子（请参见方案）。此过程不是金属辅助的，不会在金属离子的配位范围内发生。