十八烷基异氰酸酯 | 2877-26-1

• 物质功能分类: 有机原料
• 分子结构分类: 有机化合物 - 有机硫化合物 - 异硫氰酸盐
• 中文名称: 十八烷基异氰酸酯
• 中文别名: 十八烷基异硫氰酸酯
• 英文名称: 1-isothiocyanatooctadecane
• 英文别名: octadecyl isothiocyanate；Octadecylisothiocyanat；Octadecylsenfoel；1-isothiocyanato-octadecane；Octadecyl-isothiocyanat；Stearylisothiocyanat
• CAS: 2877-26-1
• 化学式: C₁₉H₃₇NS
• mdl: MFCD00041124
• 分子量: 311.575
• InChiKey: VJIRSSFEIRFISD-UHFFFAOYSA-N

物化性质

• 熔点：
  29-33 °C
• 沸点：
  140-142 °C(Press: 0.003 Torr)
• 密度：
  0.9772 (rough estimate)
• 稳定性/保质期：

  在常温常压下保持稳定，应避免与不相容材料、湿空气或水分直接接触。

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  21
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.947
• 拓扑面积：
  44.4
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xn
• 危险类别码：
  R20/21/22,R36/37/38
• 海关编码：
  2930909090
• 安全说明：
  S26,S36/37/39

SDS

Name:	Octadecyl Isothiocyanate (Pract) Material Safety Data Sheet
Synonym:	None
CAS:	2877-26-1

Section 1 - Chemical Product MSDS Name:Octadecyl Isothiocyanate (Pract) Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
2877-26-1	Octadecane, 1-Isothiocyanato-	ca 100	220-722-1

Hazard Symbols: XI
Risk Phrases: 36/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes and skin.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
Causes eye irritation.
Skin:
Causes skin irritation.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
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.
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:
Get medical aid. 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. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
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.
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:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed.
Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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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# 2877-26-1: 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 above room te
Color: white to off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 24.00 - 28.00 deg C
Autoignition Temperature: Not available.
Flash Point: > 110 deg C (> 230.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C19H37NS
Molecular Weight: 311.57

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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, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, oxides of sulfur, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 2877-26-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Octadecane, 1-Isothiocyanato- - 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 36/38 Irritating to eyes and 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 37 Wear suitable gloves.
S 37/39 Wear suitable gloves and eye/face
protection.
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# 2877-26-1: No information available.
Canada
CAS# 2877-26-1 is listed on Canada's NDSL List.
CAS# 2877-26-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 2877-26-1 is listed on the TSCA inventory.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

概述

现有技术中，十八烷基异氰酸酯（C18-OCN）通常通过十八胺与光气（COCl₂）反应制备。例如，以26.9克十八胺和12克光气进行反应，可制得十八烷基异氰酸酯。然而，这种方法存在一些缺点：光气作为剧毒气体，在实验室或工业生产中对设备密封性要求极高，并且投资成本较大；尾气中的光气从环保角度考虑会带来麻烦，因此需要额外设置生产和储存装置。此外，光气作为气体难以准确计量，尤其是在实验室进行少量精确定量时，过量使用容易引发副反应。

制备方法

一种新的化学合成十八烷基异氰酸酯的方法是通过十八胺与双(三氯甲基)碳酸酯为原料制得。具体步骤如下：首先，在0～5℃的温度下，将正己烷溶解的十八胺溶液以1.5ml/min的速度缓慢滴加到相同溶剂中溶解的双(三氯甲基)碳酸酯溶液中。反应完毕后，先在室温下搅拌0.5～5小时，然后升温至35～150℃并在该温度下反应0.5～10小时。反应完成后，通过蒸馏回收正己烷并分离出十八烷基异氰酸酯，收率可达78.2%，纯度为98.0%。

用途

十八烷基异硫氰酸酯主要用于印染助剂、毛纺织品柔软剂VS的合成原料以及防水织物表面处理。

反应信息

• 作为反应物：
  描述：

  十八烷基异氰酸酯 在 氨 、 水 作用下， 生成 octadecyl-thiourea
  参考文献：
  名称：

  Schmidt; Fehr, Justus Liebigs Annalen der Chemie, 1959, vol. 621, p. 1,7

  摘要：

  DOI：
• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以73%的产率得到十八烷基异氰酸酯
  参考文献：
  名称：

  The thiocarbonyl ‘S’ is softer than thiolate ‘S’: A catalyst-free one-pot synthesis of isothiocyanates in water

  摘要：

  在水中介质中，用甲基丙烯酸处理预制的或原位生成的芳基/烷基二硫代氨基甲酸盐三乙基铵盐（ArNHCSS−.Et3NH+）仅得到芳基异硫氰酸酯（ArNCS），而原位生成的芳基二硫代氨基甲酸（ArNHCSS−.H+）仅生成硫代迈克尔加合物（ArNHCSSCH2CH2COOMe）。这种差异性反应活性可以通过两种替代机制来解释，这取决于反荷离子的性质和反应介质的pH值。不管反荷离子如何，与二硫代氨基甲酸盐中的硫醇/硫醇盐硫（−SH/S−）相比，硫羰基硫（=S）原子具有较大的轨道系数，更为柔软，前者通过1,4-加成与迈克尔受体加合。

  DOI：

  10.1039/b923336a

文献信息

• A Novel One-pot Synthesis of Isothiocyanates and Cyanamides from Dithiocarbamate Salts Using Environmentally Benign Reagent Tetrapropylammonium Tribromide
  作者：Neivotsonuo Bernadette Kuotsu、Latonglila Jamir、Tovishe Phucho、Upasana Bora Sinha

  DOI：10.17344/acsi.2017.3342

  日期：2017.12.15

  A highly efficient and simple protocol for the synthesis of isothiocyanates and cyanamides from their respective amines in the presence of a mild, efficient, and non-toxic reagent tetrapropylammonium tribromide is described. High environmental acceptability of the reagents, cost effectiveness and high yields are the important attributes of this methodology.

  描述了在温和，有效且无毒的三溴化四铵铵存在下，由它们各自的胺合成异硫氰酸酯和氰胺的高效简单方法。试剂的高环境可接受性，成本效益和高产率是该方法的重要属性。
• Substituted Spiro Compounds and Their Use for Producing Pain-Relief Medicaments
  申请人：Frank Robert

  公开号：US20080269271A1

  公开（公告）日：2008-10-30

  The present invention relates to substituted spiro compounds, to processes for preparing them, to medicaments comprising these compounds and to the use of these compounds for producing medicaments.

  本发明涉及替代螺环化合物，涉及制备这些化合物的方法，涉及含有这些化合物的药物以及利用这些化合物生产药物的用途。
• Reactions of relevance to the chemistry of aminoglycoside antibiotics. Part 14. A useful radical-deamination reaction
  作者：Derek H. R. Barton、Gerhard Bringmann、Genevi�ve Lamotte、William B. Motherwell、Robyn S. Hay Motherwell、Alexander E. A. Porter

  DOI：10.1039/p19800002657

  日期：——

  Primary, secondary, and tertiary aliphatic or alicyclic isocyanides are smoothly reduced under radical conditions using tri-n-butylstannane to the corresponding hydrocarbons. The relative ease of reduction is tertiary > secondary > primary. Aromatic isocyanides are not reduced under these conditions. The reduction of isothiocyanates (or isoselenocyanates) by tri-n-butylstannane also affords hydrocarbons

  使用三正丁基锡烷在自由基条件下将伯，仲和叔脂族或脂环族异氰酸酯平稳还原为相应的烃。减少的相对难度是三级>二级>一级。在这些条件下不还原芳族异氰化物。通过三正丁基锡烷还原异硫氰酸酯（或异戊烯异氰酸酯）也可提供烃，但此处异氰酸酯已被证明是中间体。在1，2-关系中具有异氰酸酯和黄原酸酯官能团的化合物的还原产生平滑的自由基断裂，从而提供烯烃。描述了从葡糖胺开始的2-脱氧-D-葡萄糖的有效合成。
• Chiral phosphinothiourea-catalyzed asymmetric Morita–Baylis–Hillman reactions of acrylates with aromatic aldehydes
  作者：Kui Yuan、Hong-Liang Song、Yinjun Hu、Xin-Yan Wu

  DOI：10.1016/j.tet.2009.07.066

  日期：2009.9

  chiral bifunctional phosphinothioureas were synthesized and applied to the enantioselective Morita–Baylis–Hillman reaction of aromatic aldehydes with acrylates. In the presence of 8 mol % of organocatalyst 2e, the Baylis–Hillman adducts were obtained in good enantioselectivities and up to 96% yield under mild reaction conditions.

  合成了一系列手性双官能硫代硫脲，并将其用于芳香醛与丙烯酸酯的对映选择性森田-贝利斯-希尔曼反应。在8 mol％的有机催化剂2e的存在下，在温和的反应条件下以良好的对映选择性和高达96％的产率获得了Baylis-Hillman加合物。
• Chimie des sucres sans groupements protecteurs : synthese de carbamates, d'urees et de thiourees en position 1 du lactose
  作者：Daniel Plusquellec、Fabienne Roulleau、Eric Brown

  DOI：10.1016/s0040-4039(01)90071-1

  日期：1984.1

  The anomeric hydroxyl of lactose was carbamoylated selectively by treating the free sugar with alkylisocyanates, thus without preliminary protection of the other hydroxyls of the lactose molecule. Moreover, the readily available 1-aminolactose and 1-octyl-aminolactose reacted with isocyanates and isothiocyanates to afford selectively -lactosyl -alkylureas and -lactosyl -alkylthioureas, respectively

  通过用烷基异氰酸酯处理游离糖来选择性地将乳糖的异头羟基氨基甲酸酯化，因此没有初步保护乳糖分子的其他羟基。另外，容易获得的1-aminolactose和1-辛基aminolactose与异氰酸酯和异硫氰酸酯反应，以选择性得到乳糖苷神经-alkylureas和乳糖苷神经分别-alkylthioureas。