乙炔钠 | 1066-26-8

• 物质功能分类: 有机原料 - 有机金属类化合物 - 有机钠
• 分子结构分类: 有机化合物 - 碳氢化合物衍生物
• 中文名称: 乙炔钠
• 中文别名: 乙炔基钠；乙炔化钠
• 英文名称: sodium acetylide
• 英文别名: sodium acetylene；sodium acetylenide
• CAS: 1066-26-8
• 化学式: C₂HNa
• 分子量: 48.0197
• InChiKey: SLBNQJAGYKQCKI-UHFFFAOYSA-N

物化性质

• 沸点：
  -22.2°C
• 密度：
  0,865 g/cm3
• 闪点：
  85 °F
• 稳定性/保质期：
  1. 常温常压下稳定，避免与氧化物、酸和水分接触。 2. 在潮湿空气中会缓慢分解，在1大气压下加热至约150℃时会彻底分解。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.17
• 重原子数：
  3
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• TSCA：
  Yes
• 危险等级：
  4.3
• 危险品标志：
  Xn,F
• 安全说明：
  S36/37,S43
• 危险类别码：
  R20/21,R10,R15,R38
• WGK Germany：
  3
• 海关编码：
  29310099
• 危险品运输编号：
  UN 3399 4.3/PG 1
• 危险类别：
  4.3
• 包装等级：
  II
• 储存条件：
  在干燥的惰性气体中保持容器密封，并存放在阴凉、干燥的地方。

SDS

Name:	Sodium acetylide 18 wt% slurry in xylene/light mineral oil 95% Material Safety Data Sheet
Synonym:	None
CAS:	1066-26-8

Section 1 - Chemical Product MSDS Name:Sodium acetylide 18 wt% slurry in xylene/light mineral oil 95% Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1066-26-8	Sodium acetylide	18	213-908-9

Hazard Symbols: XN
Risk Phrases: 10 14 20/21 38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Flammable. Reacts violently with water. Harmful by inhalation and in contact with skin. Irritating to skin.Air sensitive.Water-reactive.
Potential Health Effects
Eye:
Causes eye irritation. When substance becomes wet or comes in contact with moisture of the mucous membranes, it will cause irritation. May cause chemical conjunctivitis and corneal damage.
Skin:
Causes skin irritation. Contact with skin causes irritation and possible burns, especially if the skin is wet or moist. May cause irritation and dermatitis. May cause cyanosis of the extremities.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated. Ingestion of large amounts may cause CNS depression.
Inhalation:
May cause irritation of the respiratory tract with burning pain in the nose and throat, coughing, wheezing, shortness of breath and pulmonary edema. The toxicological properties of this substance have not been fully investigated. Inhalation may be fatal as a result of spasm, inflammation, edema of the larynx and bronchi, chemical pneumonitis and pulmonary edema. Aspiration may lead to pulmonary edema. Vapors may cause dizziness or suffocation. May cause burning sensation in the chest.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
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. If water-reactive products are embedded in the skin, no water should be applied. The embedded products should be covered with a light oil.
Ingestion:
Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
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. Vapors may form an explosive mixture with air.
Vapors can travel to a source of ignition and flash back. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Will burn if involved in a fire. Water Reactive. Material will react with water and may release a flammable and/or toxic gas. Use water spray to keep fire-exposed containers cool. Containers may explode in the heat of a fire. Flammable liquid and vapor. May ignite or explode on contact with steam or moist air.
Extinguishing Media:
Use water spray to cool fire-exposed containers. Use foam, dry chemical, or carbon dioxide. DO NOT USE WATER! Contact professional fire-fighters immediately.

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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. Remove all sources of ignition. Use a spark-proof tool. Provide ventilation. Do not expose spill to water. Place under an inert atmosphere. A vapor suppressing foam may be used to reduce vapors.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation. Do not allow water to get into the container because of violent reaction. Ground and bond containers when transferring material. Use spark-proof tools and explosion proof equipment. Avoid contact with eyes, skin, and clothing. Empty containers retain product residue, (liquid and/or vapor), and can be dangerous. Keep container tightly closed. Keep away from heat, sparks and flame. Avoid ingestion and inhalation. Handle under an inert atmosphere. Store protected from air. Do not allow contact with water. Do not pressurize, cut, weld, braze, solder, drill, grind, or expose empty containers to heat, sparks or open flames. Keep from contact with moist air and steam.
Storage:
Keep away from heat, sparks, and flame. Keep away from sources of ignition. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Keep away from water. Flammables-area. Do not expose to air. Store under an inert atmosphere.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use explosion-proof ventilation equipment. 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# 1066-26-8: CAS# 1330-20-7: United Kingdom, WEL - TWA: 50 ppm TWA; 220 mg/m3 TWA United Kingdom, WEL - STEL: 100 ppm STEL; 441 mg/m3 STEL United States OSHA: 100 ppm TWA; 435 mg/m3 TWA Belgium - TWA: 50 ppm VLE; 221 mg/m3 VLE Belgium - STEL: 150 ppm VLE; 442 mg/m3 VLE France - VME: 100 ppm VME; 435 mg/m3 VME France - VLE: 150 ppm VLE; 650 mg/m3 VLE Germany: 100 ppm TWA; 440 mg/m3 TWA Germany: Skin absorber Japan: 50 ppm OEL; 217 mg/m3 OEL Malaysia: 199 ppm TWA; 434 mg/m3 TWA Netherlands: 50 ppm MAC; 210 mg/m3 MAC Russia: 50 mg/m3 TWA Spain: 50 ppm VLA-ED; 221 mg/m3 VLA-ED Spain: 100 ppm VLA-EC; 442 mg/m3 VLA-EC CAS# 8012-95-1: United States OSHA: 5 mg/m3 TWA Belgium - TWA: 5 mg/m3 VLE Belgium - STEL: 10 mg/m3 VLE Japan: 3 mg/m3 OEL Malaysia: 5 mg/m3 TWA Netherlands: 5 mg/m3 MAC Russia: 5 mg/m3 TWA (mist) Spain: 5 mg/m3 VLA-ED Spain: 10 mg/m3 VLA-EC 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 prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: pale-yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: 29 deg C ( 84.20 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: reacts
Specific Gravity/Density:
Molecular Formula: HC~2CNa
Molecular Weight: 48.02

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Combines vigorously or explosively with water.
Conditions to Avoid:
Incompatible materials, ignition sources, moisture, exposure to air, excess heat, exposure to moist air or water.
Incompatibilities with Other Materials:
Air, strong acids, strong bases, strong oxidizing agents, water.
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# 1066-26-8 unlisted.
CAS# 1330-20-7: ZE2100000 CAS# 8012-95-1: GZ8725550 PY8030000 XH7480000 LD50/LC50:
Not available.
CAS# 1330-20-7: Draize test, rabbit, eye: 87 mg Mild; Draize test, rabbit, eye: 5 mg/24H Severe; Draize test, rabbit, skin: 100% Moderate; Draize test, rabbit, skin: 500 mg/24H Moderate; Inhalation, rat: LC50 = 5000 ppm/4H; Oral, mouse: LD50 = 2119 mg/kg; Oral, rat: LD50 = 4300 mg/kg; Skin, rabbit: LD50 = >1700 mg/kg.
CAS# 8012-95-1: Draize test, rabbit, eye: 500 mg Moderate; Draize test, rabbit, eye: 100 mg/1H Mild; Draize test, rabbit, skin: 100 mg/24H Mild; Inhalation, rat: LC50 = 2062 ppm/4H; Oral, mouse: LD50 = 22 gm/kg; Oral, rat: LD50 = >24 gm/kg.
Carcinogenicity:
Sodium acetylide - Not listed by ACGIH, IARC, or NTP.
Xylene - Not listed by ACGIH, IARC, or NTP.
Oil mist, mineral - 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
Shipping Name: ORGANOMETALLIC COMPOUND SOLUTION, WATER-REACTIVE,
FLAMMABLE, N.O.S.*
Hazard Class: 4.3 (3)
UN Number: 3207
Packing Group: II
IMO
Shipping Name: ORGANOMETALLIC COMPOUND SOLUTION, WATER-REACTIVE,
FLAMMABLE, N.O.S.
Hazard Class: 4.3 (3)
UN Number: 3207
Packing Group: II
RID/ADR
Shipping Name: ORGANOMETALLIC COMPOUND SOLUTION, WATER-REACTIVE,
FLAMMABLE, N.O.S.
Hazard Class: 4.3 (3)
UN Number: 3207
Packing group: II
USA RQ: CAS# 1330-20-7: 100 lb final RQ; 45.4 kg final RQ

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 10 Flammable.
R 14 Reacts violently with water.
R 20/21 Harmful by inhalation and in contact with
skin.
R 38 Irritating to skin.
Safety Phrases:
S 8 Keep container dry.
S 9 Keep container in a well-ventilated place.
S 16 Keep away from sources of ignition - No
smoking.
S 28A After contact with skin, wash immediately with
plenty of water.
S 33 Take precautionary measures against static
discharges.
S 36/37 Wear suitable protective clothing and
gloves.
S 37 Wear suitable 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# 1066-26-8: No information available.
CAS# 1330-20-7: 2
CAS# 8012-95-1: 0
Canada
CAS# 1066-26-8 is listed on Canada's DSL List.
CAS# 1330-20-7 is listed on Canada's DSL List.
CAS# 8012-95-1 is listed on Canada's DSL List.
CAS# 1066-26-8 is not listed on Canada's Ingredient Disclosure List.
CAS# 1330-20-7 is not listed on Canada's Ingredient Disclosure List.
CAS# 8012-95-1 is listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1066-26-8 is listed on the TSCA inventory.
CAS# 1330-20-7 is listed on the TSCA inventory.
CAS# 8012-95-1 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

化学性质

乙炔钠是一种强碱性物质，化学式为C₂HNa，其结构可表示为Na⁺-C≡C⁻。该化合物在无水条件下制备，并且极易吸收水分。遇水会释放出易燃气体。乙炔钠由一个钠离子和一个炔基团构成，其中的炔基团是由两个碳原子通过三键相连而成的。钠离子与炔基团之间的连接是通过共价键实现的，这有助于保持化合物的稳定性。

用途

乙炔钠主要用于与羰基化合物反应生成炔醇，并用于合成乙炔同系物及其他含有乙炔基的化合物。例如，1-丁炔可以通过乙炔钠与溴乙烷进行亲核取代反应来制备。

生产方法

乙炔钠是在液氨中与金属钠反应而得到的产品，同时还会释放出氢气。

反应信息

• 作为反应物：
  描述：

  乙炔钠 在 selenium 作用下， 以 四氢呋喃 、 xylene 、 甲醇 为溶剂， 以69%的产率得到2-methylene-1,3-diselenole
  参考文献：
  名称：

  四硒富瓦烯 (TSF) 的实用两步合成

  摘要：

  描述了从市售乙炔钠在二甲苯轻矿物油和硒粉中制备四硒富瓦烯 (TSF)。

  DOI：

  10.1055/s-2005-872117
• 作为产物：
  描述：

  乙炔 在 sodium 、 xylene 作用下， 生成 乙炔钠
  参考文献：
  名称：

  Sodium Acetylide. I. Preparation of Sodium Acetylide by Reaction of Acetylene with Sodium in Organic Media

  摘要：

  DOI：

  10.1021/jo01357a016
• 作为试剂：
  描述：

  丙酮 、 乙炔 在 氨 、 乙炔钠 作用下， 生成 2-甲基-3-丁炔-2-醇 、 2,5-二甲基-3-己炔-2,5-二醇
  参考文献：
  名称：

  Froning; Hennion, Journal of the American Chemical Society, 1940, vol. 62, p. 654

  摘要：

  DOI：

文献信息

• BOX Structures with Additional Coordination Sites: Potential Ligands for Bifunctional Catalysis
  作者：Stefan M. Seifermann、Thierry Muller、Stefan Bräse

  DOI：10.1002/ejoc.201300279

  日期：2013.6

  The synthesis of four new bis(oxazoline) (BOX) derivatives bearing two additional coordination sites at the 4,4′-positions is presented. As these BOX scaffolds contain an unsubstituted methylene bridge, they should be capable of forming neutral metal complexes. Thus, these molecules are very interesting ligands for bifunctional catalysis. In addition, one BOX scaffold bearing two azide moieties was

  介绍了在 4,4'-位置带有两个额外配位位点的四种新双（恶唑啉）（BOX）衍生物的合成。由于这些 BOX 支架含有未取代的亚甲基桥，它们应该能够形成中性金属配合物。因此，这些分子是非常有趣的双功能催化配体。此外，一个带有两个叠氮化物部分的 BOX 支架成功地用于无铜 1,3-偶极环加成反应。所得产物再次具有高配体潜力。
• Total Synthesis of Etnangien
  作者：Pengfei Li、Jun Li、Fatih Arikan、Wiebke Ahlbrecht、Michael Dieckmann、Dirk Menche

  DOI：10.1021/ja9056163

  日期：2009.8.26

  The first total synthesis of the potent RNA-polymerase inhibitor etnangien is described, which establishes unequivocally the relative and absolute configuration of this sensitive macrolide antibiotic. Key features of the expedient and modular synthesis include stereoselective substrate-controlled boron- and tin-mediated aldol couplings to set the characteristic sequences of methyl and hydroxyl bearing

  描述了强效 RNA 聚合酶抑制剂 etnangien 的首次全合成，它明确确定了这种敏感的大环内酯类抗生素的相对和绝对构型。方便和模块化合成的关键特征包括立体选择性底物控制的硼和锡介导的羟醛偶联，以设置具有高度立体选择性和产率的甲基和羟基立体中心的特征序列，构象受限底物的有效 ​​Heck 大环化，以及不稳定侧链的后期引入。收敛方法应该适合设计的类似物。
• Synthesis of functionalized bisphosphonates via click chemistry
  作者：Hanna Skarpos、Sergey N. Osipov、Daria V. Vorob'eva、Irina L. Odinets、Enno Lork、Gerd-Volker Röschenthaler

  DOI：10.1039/b705510b

  日期：——

  An efficient general synthetic approach giving the possibility for facile, rapid and cheap access to a wide range of novel nitrogen-bisphosphonates (N-BPs) as potent drug candidates, based on the reaction of mono- and bis-propargyl-substituted bisphosphonates with a variety of azides under Cu(I) catalysis (“click” methodology), has been developed. The method allows the incorporation of two functionalities into the N-BP molecule simultaneously, as well as to ligate in situ two N-BPs to one another via the one-pot reaction of organic dibromides with propargyl-substituted bisphosphonates, generating both the diazide and Cu(I) moieties.

  一种高效的综合合成方法已经被开发出来，使得可以轻松、快速且廉价地获得大量新型的氮二膦酸盐（N-BPs）作为强效药物候选物。这种方法基于单取代和双取代的炔丙基二膦酸盐与多种叠氮化物在铜(I)催化下的反应（即“点击化学”方法）。该方法能够同时将两种功能性基团引入N-BP分子，并且可以通过一步反应将有机二溴化物与炔丙基取代的二膦酸盐连接起来，同时在原位生成二叠氮基团和铜(I)单元，从而实现两个N-BP分子之间的交联。
• 一种醋酸乌利司他及其中间体的制备方法
  申请人：成都化润药业有限公司

  公开号：CN104530169B

  公开（公告）日：2017-09-12

  本发明公开一种醋酸乌利司他及其中间体的制备方法，属于药物合成领域，醋酸乌利司他的制备方法包括以3,3‑(亚乙二氧基)‑19‑去甲孕甾‑5(10),9(11)‑二烯‑3,17‑二酮为原料，通过与乙炔钠或乙炔钾反应得到化合物III，再经过氧化物高选择性环氧化得到化合物IV，接着与4‑(N,N‑二甲基氨基)苯基溴化镁格氏试剂反应，得到化合物V，再与苯基次磺酸氯反应得到化合物VI，再分别与甲醇钠、亚磷酸三甲酯反应得到化合物VII，经水解并脱去保护基得到化合物VIII，最后乙酰化反应得到醋酸乌利司他，反应式如下：该方法合成路线短、反应条件温和、产品收率和纯度高、成本低廉且质量稳定可控，适合工业化生产。
• 一种醋酸乌利司他及其中间体的合成和生产新方法
  申请人：河南天晟泰丰医药科技有限公司

  公开号：CN111040017A

  公开（公告）日：2020-04-21

  本发明提供了醋酸乌利司他(Ulipristalacetate，化合物I)的合成和生产新方法，涉及醋酸乌利司他的生产方法具有合成路线短、反应条件温和、产品收率和纯度高、成本低廉和质量稳定可控等优点，适合工业化合成和生产醋酸乌利司他及其中间体。