二甲基乙酰胺-D9 | 16727-10-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 二甲基乙酰胺-D9
• 中文别名: 氘代N,N-二甲基乙酰胺-d
• 英文名称: nonadeutero-N,N-dimethylacetamide
• 英文别名: deutero N,N-dimethylacetamide；N,N-dimethylacetamide-d9；2,2,2-trideuterio-N,N-bis-trideuteriomethyl-acetamide；nonadeuterio-dimethylacetamide；Perdeutero-N,N-dimethyl-acetamid；Perdeutero-N,N-dimethylacetamid；2,2,2-trideuterio-N,N-bis(trideuteriomethyl)acetamide
• CAS: 16727-10-9
• 化学式: C₄H₉NO
• 分子量: 96.0501
• InChiKey: FXHOOIRPVKKKFG-GQALSZNTSA-N

物化性质

• 熔点：
  -20°C (lit.)
• 密度：
  1.033 g/mL at 25 °C
• 闪点：
  70°C
• 溶解度：
  可溶于氯仿（少许）、乙酸乙酯（少许）、甲醇（少许）
• 沸点：
  165-166°C (1013 hPa)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  6
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• WGK Germany：
  3

SDS

Name:	N N-Dimethylacetamide-d9 99+ atom% d Material Safety Data Sheet
Synonym:
CAS:	16727-10-9

Section 1 - Chemical Product MSDS Name:N N-Dimethylacetamide-d9 99+ atom% d Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
16727-10-9	N,N-Dimethylacetamide-d9, 99+ atom% d		unlisted

Hazard Symbols: T
Risk Phrases: 20/21 61

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation and in contact with skin. May cause harm to the unborn child.Hygroscopic (absorbs moisture from the air).
Potential Health Effects
The toxicological properties of this material have not been investigated. Use appropriate procedures to prevent opportunities for direct contact with the skin or eyes and to prevent inhalation.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids.
Skin:
Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up, then place into a suitable container for disposal.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry place. Keep container closed when not in use.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate general or local exhaust ventilation to keep airborne concentrations below the permissible exposure limits. Use process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels.
Exposure Limits CAS# 16727-10-9: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves and clothing to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin.
Respirators:
Wear a NIOSH/MSHA or European Standard EN 149 approved full-facepiece airline respirator in the positive pressure mode with emergency escape provisions.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 165 deg C @ 760.00mmHg
Freezing/Melting Point: 0 deg C
Autoignition Temperature: Not available.
Flash Point: 70 deg C ( 158.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: soluble
Specific Gravity/Density: 1.0400g/cm3
Molecular Formula:
Molecular Weight:

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Strong oxidants.
Incompatibilities with Other Materials:
Not available.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, irritating and toxic fumes and gases, carbon dioxide, hydrogen bromide, nitrogen.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 16727-10-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
N,N-Dimethylacetamide-d9, 99+ atom% d - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: T
Risk Phrases:
R 61 May cause harm to the unborn child.
R 20/21 Harmful by inhalation and in contact with
skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 28A After contact with skin, wash immediately with
plenty of water.
S 36 Wear suitable protective clothing.
WGK (Water Danger/Protection)
CAS# 16727-10-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 16727-10-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 16727-10-9 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  苯三羰基铬 、 二甲基乙酰胺-D9 在 catalyst: lithium tert-butoxide 作用下， 以 neat (no solvent) 为溶剂， 生成 4-乙基-2-羟基苯甲酸乙酯
  参考文献：
  名称：

  Kinetic CH-acidity of benzenetricarbonylchromium and its derivatives

  摘要：

  DOI：

  10.1007/bf01168064
• 作为产物：
  描述：

  甲醛-d2 、 乙酰胺-D3 在 甲酸-d2 作用下， 反应 24.0h， 以1.95 g的产率得到二甲基乙酰胺-D9
  参考文献：
  名称：

  Synthesis of the perdeuterated cellulose solventsN-methylmorpholineN-oxide (NMMO-d11) andN,N-dimethylacetamide (DMAc-d9)

  摘要：

  描述了完全氘化纤维素溶剂 NMMO-d11 (9) 和 N,N-二甲基乙酰胺-d9 (14) 的合成。NMMO-d11 通过五步法从未标记的二乙二醇酸 (1) 合成，经过二乙二醇-d8 (4) 及其双托烯基 (5)，后者与苄胺环化生成 N-苄基吗啉 (6)。去除苄保护基、甲基化和 N-氧化完成了合成。DMAc-d9 (14) 是通过氘化醋酸 (10) 和二甲胺–二氧化碳复合物 (17) 在酸性铝土矿催化下，通过无溶剂气固反应制得的。版权 © 2008 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.1467
• 作为试剂：
  描述：

  3-甲基-3-丁烯-1-基特戊酸酯 、 联硼酸频那醇酯 在 iron p-toluenesulfonate 、 二甲基乙酰胺-D9 、 lithium tert-butoxide 作用下， 以78%的产率得到C₁₆H₃₀⁽²⁾HBO₄
  参考文献：
  名称：

  脂族末端烯烃的无配体铁催化区域选择性控制的硼氢化

  摘要：

  区域选择性的控制已被认为是烯烃硼氢化反应的基本问题。尽管取得了相当大的进步，但是烯烃底物的特异性或配体的调节对于特定的区域选择性是必需的，这限制了通用性和实用性。在本文中，我们报告了脂族末端烯烃的无配体铁催化的区域发散氢硼化反应，该反应在高区域选择性下获得了马尔可夫尼可夫和反马尔可夫尼可夫的硼氢化产物。值得注意的是，溶剂和碱是影响区域选择性的关键因素，进一步的研究表明，醇硼铁盐配合物是决定异常马尔可夫尼科夫区域选择性的关键中间体。具有不同结构的末端烯烃（单取代和1,1-二取代，开环和环外）顺利进行了转型。该反应不需要添加辅助配体，并且该反应可以以克为单位进行，从而为合成伯，仲和叔烷基硼酸酯提供了一种有效且可持续的方法。

  DOI：

  10.1021/acscatal.0c02731

文献信息

• Visible-Light-Induced Radical Cascade Cross-Coupling via C(sp³)–H Activation and C–N/N–O Cleavage: Feasible Access to Methylenebisamide Derivatives
  作者：Jinglan Lei、Min Li、Qingqing Zhang、Shuyang Liu、Haifang Li、Lei Shi、Wen-Feng Jiang、Chunying Duan、Yunhe Jin

  DOI：10.1021/acs.orglett.3c00646

  日期：——

  Here we report facile and manipulable access to methylenebisamide derivatives via visible-light-driven radical cascade processes incorporating C(sp3)–H activation and C–N/N–O cleavage. Mechanistic studies reveal that a traditional Ir-catalyzed photoredox pathway and a novel copper-induced complex-photolysis pathway are both involved, contributing to activating the inert N-methoxyamides and rendering

  在这里，我们报告了通过包含 C(sp 3 )–H 激活和 C–N/N–O 裂解的可见光驱动的自由基级联过程，轻松且可操作地获取亚甲基双酰胺衍生物。机理研究表明，传统的 Ir 催化光氧化还原途径和新型铜诱导的复合光解途径均参与其中，有助于激活惰性N-甲氧基酰胺并提供有价值的双酰胺。这种方法具有许多优点，包括温和的反应条件、广泛的范围和官能团耐受性以及具有竞争力的步骤经济性。鉴于机械的丰富性和操作的简单性，我们相信这个一揽子交易为合成有价值的含氮分子铺平了一条有前途的道路。
• Synthesis of the perdeuterated cellulose solventsN-methylmorpholineN-oxide (NMMO-d11) andN,N-dimethylacetamide (DMAc-d9)
  作者：Christian Adelwöhrer、Yuko Yoneda、Fumiaki Nakatsubo、Thomas Rosenau

  DOI：10.1002/jlcr.1467

  日期：2008.1

  The synthesis of the perdeuterated cellulose solvents NMMO-d11 (9) and N,N-dimethylacetamide-d9 (14) is described. NMMO-d11 was obtained according to a five-step approach from non-labeled diglycolic acid (1) via diethylene glycole-d8 (4) and its bis-tosylate (5), which underwent cyclization with benzylamine to N-benzylmorpholine (6). The removal of the benzyl protecting group, methylation and N-oxidation completed the synthesis. DMAc-d9 (14) was obtained from deuterated acetic acid (10) and dimethylamine–carbon dioxide complex (17) with acidic alumina as the catalyst according to a solvent-free gas–solid reaction. Copyright © 2008 John Wiley & Sons, Ltd.

  描述了完全氘化纤维素溶剂 NMMO-d11 (9) 和 N,N-二甲基乙酰胺-d9 (14) 的合成。NMMO-d11 通过五步法从未标记的二乙二醇酸 (1) 合成，经过二乙二醇-d8 (4) 及其双托烯基 (5)，后者与苄胺环化生成 N-苄基吗啉 (6)。去除苄保护基、甲基化和 N-氧化完成了合成。DMAc-d9 (14) 是通过氘化醋酸 (10) 和二甲胺–二氧化碳复合物 (17) 在酸性铝土矿催化下，通过无溶剂气固反应制得的。版权 © 2008 John Wiley & Sons, Ltd.
• Kinetic CH-acidity of benzenetricarbonylchromium and its derivatives
  作者：M. V. Antonova、S. K. Moiseev、V. N. Kalinin、I. O. Shapiro

  DOI：10.1007/bf01168064

  日期：1989.11