乙炔二羰酰胺 | 543-21-5

• 物质功能分类: 化学试剂 - 有机试剂 - 酰胺
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 中文名称: 乙炔二羰酰胺
• 中文别名: 叶枯炔；乙炔二羧酰胺
• 英文名称: Cellocidin
• 英文别名: acetylenedicarboxamide；Acetylen-dicarbonsaeurediamid；acetylenedicarboxylic acid diamide；but-2-ynediamide
• CAS: 543-21-5
• 化学式: C₄H₄N₂O₂
• mdl: MFCD00017146
• 分子量: 112.088
• InChiKey: JBTGHKUTYAMZEZ-UHFFFAOYSA-N

物化性质

• 熔点：
  179 °C
• 沸点：
  209.98°C (rough estimate)
• 密度：
  1.4421 (rough estimate)
• 溶解度：
  DMF：10mg/mL； DMSO：20mg/mL； DMSO:PBS (pH 7.2) (1:7)：0.12 mg/mL
• 稳定性/保质期：

  在常温常压下保持稳定，应避免与不相容的材料接触。

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险品标志：
  T
• 安全说明：
  S28A,S36/37,S45
• 危险类别码：
  R25,R21
• 海关编码：
  2924199090
• 储存条件：
  密封保存，应储存在阴凉干燥的仓库中。

SDS

Name:	Acetylenedicarboxamide (pract) Material Safety Data Sheet
Synonym:	2-Butynediamide; Cellocidin
CAS:	543-21-5

Section 1 - Chemical Product MSDS Name:Acetylenedicarboxamide (pract) Material Safety Data Sheet
Synonym:2-Butynediamide; Cellocidin

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
543-21-5	Acetylenedicarboxamide, pract.	>98 %	unlisted

Hazard Symbols: T
Risk Phrases: 21 25

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful in contact with skin. Toxic if swallowed.Toxic.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation. Harmful if absorbed through the skin.
Ingestion:
May be fatal if swallowed. Harmful if swallowed. Causes gastrointestinal irritation with nausea, vomiting and diarrhea.
Inhalation:
Causes respiratory tract irritation.
Chronic:
No information found.

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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. Get medical aid immediately.
Skin:
Get medical aid immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Do not induce vomiting. If victim is conscious and alert, give 2-4 cupfuls of milk or water. Never give anything by mouth to an unconscious person. Get medical aid immediately. SPEED IS ESSENTIAL.
A DOCTOR MUST BE NOTIFIED AT ONCE.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
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:
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. Wash hands before eating. Remove contaminated clothing and wash before reuse. Use only in a well-ventilated area. Do not get on skin or in eyes. Do not ingest or inhale.
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 process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels.
Exposure Limits CAS# 543-21-5: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves and clothing to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: Not available.
Odor: none reported
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 179 deg C
Autoignition Temperature: Not available.
Flash Point: 216 deg C ( 420.80 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: 216 deg C
Solubility in water: slightly soluble
Specific Gravity/Density:
Molecular Formula: C4H4N2O2
Molecular Weight: 112.09

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Irritating and toxic fumes and gases.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 543-21-5: AO9900000 LD50/LC50:
CAS# 543-21-5: Oral, mouse: LD50 = 89200 ug/kg.
Carcinogenicity:
Acetylenedicarboxamide, pract. - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

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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 21 Harmful in contact with skin.
R 25 Toxic if swallowed.
Safety Phrases:
S 28A After contact with skin, wash immediately with
plenty of water.
S 36/37 Wear suitable protective clothing and
gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 543-21-5: No information available.
Canada
CAS# 543-21-5 is listed on Canada's NDSL List.
CAS# 543-21-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 543-21-5 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

类别：农药
毒性分级：高毒
急性毒性（口服）：小鼠 LD50 为 89.2 毫克/公斤
可燃性危险特性：燃烧时会产生有毒氮氧化物气体
储运特性：需存放在通风、低温和干燥的库房中，并与食品原料分开储存运输
灭火剂：干粉、泡沫或砂土

反应信息

• 作为反应物：
  描述：

  乙炔二羰酰胺 在 四磷十氧化物 作用下， 以22%的产率得到丁烷-1,4-二胺
  参考文献：
  名称：

  一种新的和潜在的益生元α-胞苷衍生物。

  摘要：

  由核糖氨基恶唑啉和二氰基乙炔的益生元反应合成了一种新的α-胞苷衍生物。通过 X 射线衍射证实了产物的四环结构，然后找到了适合大规模合成的替代 6 步合成途径。

  DOI：

  10.1039/c7cc00693d
• 作为产物：
  描述：

  dimethyl meso-2,3-difluorosuccinate 在 氨 作用下， 生成 乙炔二羰酰胺
  参考文献：
  名称：

  Kharasch; Jensen; Urry, Journal of Organic Chemistry, 1945, vol. 10, p. 392

  摘要：

  DOI：

文献信息

• Organic heterocyclothiazenes. Part 5. Cycloaddition reactions of tetrasulphur tetranitride with highly electron deficient alkynes
  作者：Peter J. Dunn、Charles W. Rees

  DOI：10.1039/p19870001579

  日期：——

  4-trifluorobutynonitrile (4) similarly give the trithiadiazepines (10) and (12), though more slowly and in slightly lower yields. Structures (8) and (10) correct literature assignments. The analogous reactions of ethyl 3-formylpropynoate (6), hex-3-yne-2,5-dione (7), and butynedial, like those of acetylenedicarboxylate esters, give complex mixtures from which trithiadiazepines, trithiatriazepines, and thiadiazoles

  与先前的复杂S 4 N 4-炔反应相反，丁腈和S 4 N 4的处理可得到1,3,5,2,4-三噻二氮杂-6,7-二碳腈（8）和1， 2,5-噻二唑-3,4-二甲腈（9）非常干净，收率很高。六氟丁-2-炔和4,4,4-三氟丁腈（4）类似地产生三噻二氮杂（10）和（12），尽管速度较慢且收率略低。结构（8）和（10）纠正文献分配。3-甲酰基丙酸乙酯（6），己-3-炔-2,5-二酮（6）的类似反应7），丁炔和乙炔二羧酸酯一样，得到复杂的混合物，从中可以不同地分离出三噻二氮杂，三噻三氮杂和噻二唑。建议对这些结果进行机械合理化。由S 4 N 4和1,1,4,4-四乙氧基丁炔（20）以高收率制备1,2,5-噻二唑-3,4-二甲醛（18b），然后进行水解。该二醛和其他3,4-二氧代-1,2,5-噻二唑首次用于制备1,2,5-噻二唑并[3,4- d ]哒嗪及其衍生物（22）。改进的3-甲酰基丙酸乙酯（6）和十六烷基-3-炔-2
• Pesticides
  申请人：Rhone-Poulenc, Inc.

  公开号：US06346522B1

  公开（公告）日：2002-02-12

  Compounds of formula (I) or pesticidally acceptable salts thereof, compositions containing them and methods of use.

  式(I)的化合物或其农药可接受的盐，含有它们的组合物以及使用方法。
• Compound and method of producing organic semiconductor device
  申请人：Canon Kabushiki Kaisha

  公开号：US07928221B2

  公开（公告）日：2011-04-19

  A method of producing an organic semiconductor device is provided in which a layer composed of an organic semiconductor having excellent crystallinity and orientation in a low-temperature region can be formed, and the device can be produced in the air. The method includes forming a layer composed of an organic semiconductor precursor on a base body and irradiating the organic semiconductor precursor with light, wherein the organic semiconductor precursor is a porphyrin compound or an azaporphyrin compound having in its molecule at least one of the structure represented by the following general formula (1) or (2):

  提供了一种生产有机半导体器件的方法，其中可以在低温区域形成具有优异结晶性和取向性的有机半导体层，并且可以在空气中生产该器件。该方法包括在基体上形成由有机半导体前体组成的层，并用光辐照有机半导体前体，其中有机半导体前体是具有下述一般式（1）或（2）所代表结构中至少一种的卟啉化合物或氮杂卟啉化合物：
• Electron spin resonance investigation of sulphur-33 and nitrogen-15 substituted dithiazol-2-yl and dithiazolidin-2-yl free radicals
  作者：Shirley A. Fairhurst、Roger S. Pilkington、Leslie H. Sutcliffe

  DOI：10.1039/f19837900925

  日期：——

  Thermal cyclo-addition reactions of tetrasulphur dinitride with certain alkynes generate a new series of stable free radicals possessing the 1,3,2-dithiazolyl ring. The radicals have simple e.s.r. spectra and are potentially useful spin probes or labels. The sharpness of the spectral lines has enabled us to observe natural abundance lines from nitrogen-15, sulphur-33 and carbon-13. The presence of

  四氮化二氮与某些炔烃的热环加成反应生成一系列具有1,3,2-二噻唑基环的稳定自由基。这些自由基具有简单的esr光谱，可能是有用的自旋探针或标记。光谱线的清晰度使我们能够观察到来自氮15，硫33和碳13的自然丰度线。通过氮15和硫33的同位素双重标记已证明杂环中存在两个等效的硫原子。用相关的1,3,2-二噻唑烷基进行了后两种同位素和氘的同位素三重标记实验。
• NIR chromophores from small acetylenic building blocks: a Diels–Alder approach to octaalkynylphthalocyanines
  作者：Rüdiger Faust、Frieder Mitzel

  DOI：10.1039/b006114j

  日期：——

  Two new routes to cross-conjugated 3,4-dimethylenehexa-1,5-diynes, both starting from dialkynyl 1,2-diones, have been devised. Whereas triisopropylsilyl-protected diketones could be diolefinated in a bis-Wittig reaction with methylenetriphenylphosphorane, their aryl-terminated congeners had to be subjected to the conditions of the Peterson olefination (trimethylsilylmethylmagnesium chloride and subsequent dehydration of the resulting diol with thionyl chloride). The reactivity of the diethynylbutadienes towards standard dienophiles was found to be low and alternative thermal reactions compete with [4 + 2] cycloadditions. However, dicyanoacetylene was shown to be an effective cycloaddition partner leading, after aromatisation, to the corresponding dicyanodiethynylbenzenes. These were cyclotetramerised with magnesium butanolate in butanol to furnish octaalkynylphthalocyanines, thereby completing a concise, three-step synthesis of these NIR chromophores of relevance to photodynamic forms of therapy.

  研究人员设计了两条新的路线，从 1,2 二炔基二酮出发，制备交叉共轭的 3,4-二亚甲基六-1,5-二炔。三异丙基硅烷保护的二酮类化合物可以在与亚甲基三苯基膦的双维蒂希反应中进行二烯化反应，而其芳基封端的同系物则必须在彼得森烯化反应的条件下进行（三甲基硅甲基氯化镁，然后用亚硫酰氯对生成的二元醇进行脱水）。研究发现，二炔丁二烯与标准亲二烯的反应活性较低，替代热反应与[4Â +Â 2]环加成反应存在竞争。不过，二氰基乙炔被证明是一种有效的环加成伙伴，经过芳香化后可生成相应的二氰基二炔基苯。这些化合物在丁醇中与丁酸镁发生环四聚反应，生成八烷基炔基酞菁，从而完成了与光动力疗法相关的近红外发色团的简明三步合成。

表征谱图