3-(二甲氨基)-2-异氰基丙烯酸甲酯 | 113212-14-9

• 物质功能分类: 化学试剂 - 有机试剂 - 氰酸酯/异氰酸酯
• 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: 3-(二甲氨基)-2-异氰基丙烯酸甲酯
• 中文别名: 甲基3-(N,N-二甲氨基)-2-异氰丙烯酸盐；3-(二甲基氨基)-2-异氰基丙烯酸甲酯
• 英文名称: methyl 3-(dimethylamino)-2-isocyanoacrylate
• 英文别名: 2-Isocyano-3-dimethylaminoacrylic acid methyl ester；methyl 3-(dimethylamino)-2-isocyanoprop-2-enoate
• CAS: 113212-14-9
• 化学式: C₇H₁₀N₂O₂
• mdl: MFCD06660129
• 分子量: 154.169
• InChiKey: FREGRQYTSPAJDX-UHFFFAOYSA-N

物化性质

• 熔点：
  61-67 °C

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  33.9
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S36/37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  29269090
• 储存条件：
  冰箱（+4°C）

SDS

Name:	Methyl 3-(dimethylamino)-2-isocyanoacrylate 96% Material Safety Data Sheet
Synonym:	None Known
CAS:	113212-14-9

Section 1 - Chemical Product MSDS Name:Methyl 3-(dimethylamino)-2-isocyanoacrylate 96% Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
113212-14-9	Methyl 3-(dimethylamino)-2-isocyanoacr	96%	unlisted

Hazard Symbols: XN
Risk Phrases: 20/21/22 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation, in contact with skin and if swallowed.
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation. Harmful if absorbed through the skin. May be metabolized to cyanide which in turn acts by inhibiting cytochrome oxidase impairing cellular respiration.
Ingestion:
Harmful if swallowed. May cause irritation of the digestive tract.
Metabolism may release cyanide, which may result in headache, dizziness, weakness, collapse, unconsciousness and possible death.
Inhalation:
Harmful if inhaled. Causes respiratory tract irritation. May be metabolized to cyanide which in turns act by inhibiting cytochrome oxidase impairing cellular respiration.
Chronic:
Exposure to small amounts of cyanide compounds over long periods of time is reported to cause loss of appetite, headache, weakness, nausea, dizziness, and symptoms of irritation of the upper respiratory tract and eyes.

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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:
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. 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:
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 water spray, dry chemical, carbon dioxide, or chemical 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:
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. 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 cool, dry place. Store in a tightly closed container.

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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# 113212-14-9: 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:
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: Crystalline powder
Color: yellow
Odor: stench
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 61 - 67 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: Insoluble.
Specific Gravity/Density:
Molecular Formula: C7H10N2O2
Molecular Weight: 154.17

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 113212-14-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Methyl 3-(dimethylamino)-2-isocyanoacrylate - 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
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
IMO
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing Group: III
RID/ADR
Shipping Name: TOXIC SOLID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2811
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: XN
Risk Phrases:
R 20/21/22 Harmful by inhalation, in contact with
skin and if swallowed.
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 113212-14-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 113212-14-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 113212-14-9 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：

  2-氟苄胺 、 3-(二甲氨基)-2-异氰基丙烯酸甲酯 在 盐酸 、 乙酸乙酯 、 二氯甲烷 、 水 、 magnesium sulfate 、 silica gel 、 乙醚 作用下， 以 邻二甲苯 、 乙酸乙酯 为溶剂， 反应 3.0h， 以1-(o-fluorobenzyl)-imidazole-4-carboxylic acid methyl ester having a melting point of 87°-89° is obtained的产率得到1-(o-fluorobenzyl)-imidazole-4-carboxylic acid methyl ester
  参考文献：
  名称：

  1-Phenyl-lower alkyl-imidazole 4- or 5-carboxamide compounds which are

  摘要：

  以下是翻译的结果： 公式为##STR1##的1-苯基-低碳基咪唑-4-和/或5-羧酰胺具有抗惊厥特性，其中Ph代表被低碳基和/或卤素取代的苯基，alk代表低碳基亚甲基，R.sub.1和R.sub.2中的一个是可选地被低碳基或低酰基取代的碳酰胺基，而另一个是氢、低碳基或可选地被低碳基或低酰基取代的碳酰胺基，而R.sub.3代表氢或低碳基，可用作抗惊厥剂。它们的制造方法如下：在公式为##STR2##的化合物中，其中R.sub.1'代表一个基团R.sub.1或X，而R.sub.2'代表一个基团X，或者R.sub.1'代表一个基团X，而R.sub.2'代表一个基团R.sub.2，其中X代表一个可转化为可选地被低碳基或单取代的低酰基的碳酰胺基或二取代的碳酰胺基，基团X或基团X被转化为可选地被低碳基或单取代的低酰基的碳酰胺基或单取代的低酰基。

  公开号：

  US04851424A1

文献信息

• (−)-Bacillamide C: the convergent approach
  作者：Wei Wang、Shannon Joyner、Kareem Andrew Sameer Khoury、Alexander Dömling

  DOI：10.1039/b918214d

  日期：——

  The newly discovered natural product bacillamide C and several derivatives were convergently synthesized for the first time and in only three steps. The key transformation constitutes a thiazole Ugi multicomponent reaction. These compounds will serve to elucidate chemical biology and SAR of this potent anti-algae natural product and shows the synthetic pathway to related natural products.

  新发现的天然产物巴卡拉酰胺 C 及其几种衍生物首次在三个步骤内被聚合合成。关键的转化过程是噻唑乌基多组分反应。这些化合物将有助于阐明这种强效抗藻天然产物的化学生物学和 SAR，并展示了相关天然产物的合成途径。
• Stereoselective Total Synthesis of Tubulysin V
  作者：Rui Wang、Ping Tian、Guoqiang Lin

  DOI：10.1002/cjoc.201200984

  日期：2013.1

  The total synthesis of tubulysin V was accomplished in 1.0% overall yield with linear 13 steps. Our synthetic strategy featured the following two reactions. One is zinc‐mediated aza‐Barbier reaction of (R)‐N‐tert‐butanesulfinyl imine 8 with β‐ester group functionalized allylic bromide 9 to afford the chiral homo‐allylic amine (7); the other is to employ the methodology of aqueous indium‐mediated aza‐Barbier

  微管溶素V的总合成以1.0％的总收率线性完成了13个步骤。我们的综合策略具有以下两个反应。一个是（锌-介导的氮杂Barbier反应- [R ）- ñ -叔-butanesulfinyl亚胺8与β -酯基团官能烯丙基溴9，得到手性高烯丙基胺（7）; 另一种方法是采用我们小组先前开发的以水为媒介的铟介导的氮杂-Barbier反应的方法，从而高效地获得手性均烯丙基胺13。
• Screening Multicomponent Reactions for X-Linked Inhibitor of Apoptosis-Baculoviral Inhibitor of Apoptosis Protein Repeats Domain Binder
  作者：Ilaria Monfardini、Jui-Wen Huang、Barbara Beck、Jason F. Cellitti、Maurizio Pellecchia、Alexander Dömling

  DOI：10.1021/jm101341m

  日期：2011.2.10

  We report a second example of a general reaction screening approach to discover low molecular weight inhibitors of protein protein interactions. On the basis of the known pharmacophore model of SMAC mimetics, we predicted several inhibitors based on four different multicomponent reactions. The predicted inhibitors were subsequently synthesized, tested, and found to bind to the antiapoptotic protein X-linked inhibitor of apoptosis protein (XIAP) and showed cellular activity. Also the compounds are currently not highly potent. They could form a starting point for future medicinal chemistry optimization.
• A Novel One-Pot Multicomponent Enzymatic Synthesis of 2,4-Disubstituted Thiazoles
  作者：Huiping Zhang

  DOI：10.1007/s10562-014-1229-1

  日期：2014.5

  A novel one-pot multicomponent synthetic method of some new 2,4-disubstituted thiazoles catalyzed by enzyme was developed. Lipase from porcine pancreas (PPL) displayed good catalytic activity to promote this reaction starting from amines, aldehyde, thioacetic acid and methyl 3-(dimethyl amino)-2-isocyanoacrylate under mild conditions (35 A degrees C) with good yields (up to 93 %). The experimental results revealed PPL showed broad catalytic activity to substrates. The blank and control experiments revealed that PPL played important catalytic role during the process. All the new compounds were confirmed by IR, H-1 NMR, C-13 NMR, MS and elemental analysis. This PPL-catalyzed one-pot multicomponent synthetic method provided a new strategy to synthesize 2,4-disubstituted thiazoles and expanded the application of enzymes in organic synthesis.
• 1-Phenyl-lower alkyl-imidazole 4- or 5-carboxamide compounds which are
  申请人：Ciba-Geigy Corporation

  公开号：US04851424A1

  公开（公告）日：1989-07-25

  1-Phenyl-lower alkylimidazole-4- and/or 5-carboxamides of the formula ##STR1## in which Ph represents phenyl substituted by lower alkyl and/or by halogen, alk represents lower alkylidene, one of the radicals R.sub.1 and R.sub.2 is carbamoyl optionally substituted by lower alkyl or by lower alkanoyl and the other is hydrogen, lower alkyl, or carbamoyl optionally substituted by lower alkyl or by lower alkanoyl, and R.sub.3 represents hydrogen or lower alkyl, have anticonvulsive properties and can be used as anticonvulsives. They are manufactured as follows: in a compound of the formula ##STR2## in which R.sub.1 ' represents a radical R.sub.1 or X and R.sub.2 ' represents a radical X, or R.sub.1 ' represents a radical X and R.sub.2 ' represents a radical R.sub.2, where X represents a group that can be converted into carbamoyl that optionally is mono- or di-substituted by lower alkyl or monosubstituted by lower alkanoyl, the radical X or the radicals X is/are converted into carbamoyl that optionally is mono- or di-substituted by lower alkyl or monosubstituted by lower alkanoyl.

  以下是翻译的结果： 公式为##STR1##的1-苯基-低碳基咪唑-4-和/或5-羧酰胺具有抗惊厥特性，其中Ph代表被低碳基和/或卤素取代的苯基，alk代表低碳基亚甲基，R.sub.1和R.sub.2中的一个是可选地被低碳基或低酰基取代的碳酰胺基，而另一个是氢、低碳基或可选地被低碳基或低酰基取代的碳酰胺基，而R.sub.3代表氢或低碳基，可用作抗惊厥剂。它们的制造方法如下：在公式为##STR2##的化合物中，其中R.sub.1'代表一个基团R.sub.1或X，而R.sub.2'代表一个基团X，或者R.sub.1'代表一个基团X，而R.sub.2'代表一个基团R.sub.2，其中X代表一个可转化为可选地被低碳基或单取代的低酰基的碳酰胺基或二取代的碳酰胺基，基团X或基团X被转化为可选地被低碳基或单取代的低酰基的碳酰胺基或单取代的低酰基。