1,1,4,4-四乙氧基-2-丁炔 | 3975-08-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1,1,4,4-四乙氧基-2-丁炔
• 英文名称: 1,1,4,4-tetraethoxy-2-butyne
• 英文别名: acetylene dialdehyde tetraethylacetal；1,1,4,4-tetraethoxybut-2-yne；1,1,4,4-tetraethoxy-but-2-yne；butynedial bis-(diethyl acetal)；butynedial-bis-diethylacetal；Acetylendialdehyd-bis-diaethylacetal
• CAS: 3975-08-4
• 化学式: C₁₂H₂₂O₄
• mdl: MFCD00067010
• 分子量: 230.304
• InChiKey: QJVVNQLFPMBGLC-UHFFFAOYSA-N

物化性质

• 熔点：
  17.5°C
• 沸点：
  292.3°C (rough estimate)
• 密度：
  0.9874 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2909199090

SDS

Name:	1 1 4 4-Tetraethoxy-2-Butyne 99% Material Safety Data Sheet
Synonym:	Acetylenedicarbaldehyde Tetraethyldiacetal
CAS:	3975-08-4

Section 1 - Chemical Product MSDS Name:1 1 4 4-Tetraethoxy-2-Butyne 99% Material Safety Data Sheet
Synonym:Acetylenedicarbaldehyde Tetraethyldiacetal

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
3975-08-4	1,1,4,4-Tetraethoxy-2-Butyne	99%	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea.
Inhalation:
Causes respiratory tract irritation. Can produce delayed pulmonary edema.
Chronic:
Effects may be delayed.

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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. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If breathing is difficult, give oxygen. Do NOT use mouth-to-mouth resuscitation. If breathing has ceased apply artificial respiration using oxygen and a suitable mechanical device such as a bag and a mask.
Notes to Physician:
Treat symptomatically and supportively.

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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. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate 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. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Provide ventilation.

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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. Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation.
Storage:
Keep container closed when not in use. Store in a tightly closed container. Keep refrigerated. (Store below 4C/39F.)

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 3975-08-4: 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 to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin.
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: Liquid
Color: clear colorless to pale yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 107 deg C @ 4.00mm Hg
Freezing/Melting Point: 17 - 18 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: .9525g/cm3
Molecular Formula: C12H22O4
Molecular Weight: 230.00

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 3975-08-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1,1,4,4-Tetraethoxy-2-Butyne - 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: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 3975-08-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 3975-08-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 3975-08-4 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：

  1,1,4,4-四乙氧基-2-丁炔 在 甲酸 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到4,4-乙氧基-2-丁基卡因-铝
  参考文献：
  名称：

  具有类白三烯活性的丁酸4,4'-[（4E，6Z，9Z-十五碳三烯-2-亚基）-双）的合成：新型乙炔缩醛和二硫缩醛作为白三烯-C 4的拮抗剂

  摘要：

  对称的乙缩醛5a与受保护的半胱氨酸的选择性交换反应易于提供与白三烯-E 4有关的半硫缩醛9a和11a 。乙炔双-（二乙缩醛）12的使用导致标题化合物17a的容易的合成。其相应的六氢类似物在分离的豚鼠肺实质上显示出明显的针对LT-C 4诱导的收缩的拮抗活性。

  DOI：

  10.1016/s0040-4039(00)99018-x
• 作为产物：
  描述：

  在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 以80%的产率得到1,1,4,4-四乙氧基-2-丁炔
  参考文献：
  名称：

  乙炔二甲醛单和二缩醛的大规模合成

  摘要：

  描述了从2，5-二甲氧基-2，5-呋喃开始的有价值的乙炔二羧醛二甲基和四甲基乙缩醛的容易，高产率，大规模且原子经济的合成。

  DOI：

  10.1016/j.tetlet.2004.01.022

文献信息

• Versatilite de reactivite de l`acetylene dicarbaldehyde et des aldehydes α-acetyleniques a l'egard des dienes conjugues cycliques et heterocycliques en milieu acide
  作者：A. Gorgues、A. Simon、A. Le Coq、A. Hercouet、F. Corre

  DOI：10.1016/s0040-4020(01)87436-6

  日期：1986.1

  of acetylenedicarbaldehyde and the corresponding mono acetal is described. A comparison of their reactivity with other α-acetylenic aldehydes R-CC-CHO to towards conjugated cydic or hetero- cydic dienes is presented. Under neutral conditions, the only expected Diels-Alder adducts are formed. Under acidic conditions (HCO2H, CF3,CO2H or eventually AcOH) they afford the only Diel-Alder adduct when the

  描述了乙炔二甲醛和相应的单缩醛的制备。它们与其它α-炔醛RCC-CHO的反应性的比较来向共轭cydic或异cydic二烯被呈现。在中性条件下，仅形成预期的Diels-Alder加合物。在酸性条件下（HCO 2 H，CF 3，CO 2 H或最终为AcOH），当环丁二烯不表现出任何芳族特征时，它们会提供唯一的Diel-Alder加合物，而在相反的情况下，Michael加成物或多或少重要数量; 从呋喃开始，还可以观察到第三个途径来处理双亲电子取代化合物的形成。的机制进行了讨论和特别地，共用偶极的中间为竞争形成建议帐户和。
• 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
• Metal–organic frameworks exhibiting strong anion–π interactions
  作者：Il'ya A. Gural'skiy、Pavlo V. Solntsev、Harald Krautscheid、Konstantin V. Domasevitch

  DOI：10.1039/b612660j

  日期：——

  a pronounced ability for anion-pi interactions we have developed unsubstituted pyridazino[4,5-d]pyridazine, which was readily accessible by a novel one-pot synthesis involving inverse electron demand Diels-Alder cycloaddition (Scheme 1). Unusual anion binding properties of the ligand may be clearly related to its electron-deficiency (LUMO energy -1.591 vs. -0.288 eV for the parent pyridazine), influenced

  配位聚合物为吸附，客体和阴离子的识别与传感提供了巨大的潜力。它们的结构通常为诸如pi-pi堆积和XH ... pi氢键之类的特定相互作用提供结合位点。后者反映了pi云与正极化原子相互作用的能力。与上述键合方案相似的阴离子种类与缺电子杂环之间的静电相互作用也是可能的，并且最近在固态和溶液中都证明存在阴离子-π相互作用。这种作用对于生物分子/溶液界面也很重要，因为它发生在蛋白质结构中。实际上，这种相互作用对于配位聚合物的主客体化学特别重要，特别是用于疏水性晶体腔的功能化和几何刚性阴离子受体的设计。但是，典型的缺电子杂环如1,3,5-三嗪和1,2,4,5-四嗪是非常弱的供体，它们几乎不适合桥接金属离子和生成配位骨架。作为一种结合了对过渡金属离子的高效给体性质和显着的阴离子与pi相互作用能力的系统，我们开发了未取代的哒嗪并[4,5-d]哒嗪，可通过涉及逆电子需求的新型一锅合成轻松获得Diels-A
• Norbornadiene-Fused Heterocycles: Synthesis of 5,8-Dihydro-5,8-methanophthalazines and Regioselective Ring Cleavage and Skeletal Rearrangement of 6,7-Epoxy-5,6,7,8-tetrahydro-5,8-methanophthalazine 2-Oxides in Trifluoroacetic Acid
  作者：Tomoshige Kobayashi、Hideki Sugawara、Behrooz Nikaeen

  DOI：10.1246/bcsj.71.497

  日期：1998.2

  5,8-Dihydro-5,8-methanophthalazine, prepared by the reaction of bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarbaldehyde with hydrazine, reacted with MCPBA to give an N-oxide. Further oxidation with MCPBA afforded the corresponding exo-6,7-epoxy derivative. Treatments of the epoxide and its diphenyl-substituted derivative with trifluoroacetic acid gave 6,9-bis(trifluoroacetoxy) derivatives by a regioselective

  5,8-Dihydro-5,8-methanophthalazine，由双环[2.2.1]庚-2,5-二烯-2,3-二甲醛与肼反应制备，与MCPBA反应生成N-氧化物。用 MCPBA 进一步氧化得到相应的 exo-6,7-环氧衍生物。用三氟乙酸处理环氧化物及其二苯基取代的衍生物，通过环氧乙烷的区域选择性开环，伴随着 Wagner-Meerwein 重排得到 6,9-双（三氟乙酰氧基）衍生物。双（三氟乙酰氧基）衍生物被转化为相应的二醇以阐明它们的区域和立体化学。
• Soluble and polymer-supported 2- and 3-benzylated furans for the preparation of α,β-ethylenic carbonyl compounds
  作者：Sébastien Albert、Adrien Soret、Luis Blanco、Sandrine Deloisy

  DOI：10.1016/j.tet.2007.01.030

  日期：2007.3

  Soluble and polymer-supported 2- and 3-benzylated furans were subjected to a sequence involving a Diels–Alder reaction with α,β-acetylenic carbonyl compounds, a Michael addition, and a subsequent retro-Diels–Alder reaction to yield olefinic compounds. On solid support, this traceless strategy is advantageous since pure compounds were released in the thermal cycloreversion step. The fur-2-ylated resin

  可溶性和聚合物负载的2-和3-苄基呋喃要经历一个与α，β-炔属羰基化合物进行Diels-Alder反应，迈克尔加成反应以及随后的Diels-Alder逆反应以生成烯烃化合物的顺序。在固体载体上，这种无痕化策略是有利的，因为在热循环还原步骤中会释放出纯净的化合物。呋喃-2-基化的树脂允许高度非对映选择性的合成。