(二甲基氨亚甲基)丙二腈 | 16849-88-0

• 物质功能分类: 有机原料 - 氨基化合物 - 无环单胺、多胺及其衍生物和盐
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: (二甲基氨亚甲基)丙二腈
• 中文别名: 二甲胺亚甲基丙二腈
• 英文名称: 1-(dimethylamine)-2,2-dicyanoethylene
• 英文别名: 2-((dimethylamino)methylene)malononitrile；Dimethylamino-methylen-malodinitril；Dimethylamino-methylen-malonsaeuredinitril；(dimethylamino)methylene malononitrile；Dimethylaminomethylen-malononitril；Dimethylaminomethylen-malonitril；Malononitrile, ((dimethylamino)methylene)-；2-(dimethylaminomethylidene)propanedinitrile
• CAS: 16849-88-0
• 化学式: C₆H₇N₃
• mdl: MFCD00001853
• 分子量: 121.142
• InChiKey: LBUDLOYYNHQKQI-UHFFFAOYSA-N

物化性质

• 熔点：
  84-85 °C(lit.)
• 沸点：
  215.85°C (rough estimate)
• 密度：
  1.0556 (rough estimate)
• 溶解度：
  甲醇（微溶）、水（微溶）
• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xn,Xi
• 安全说明：
  S36
• 危险类别码：
  R20/21/22
• WGK Germany：
  3
• 海关编码：
  2926909090
• RTECS号：
  OO3746000
• 包装等级：
  III
• 危险类别：
  6.1
• 危险性防范说明：
  P261,P264,P270,P271,P280,P302+P352,P304+P340,P310,P330,P361,P403+P233,P405,P501
• 危险品运输编号：
  2811
• 危险性描述：
  H301,H311,H331
• 储存条件：
  存于阴凉干燥处。

SDS

Name:	(Dimethylaminomethylene)Malononitrile Material Safety Data Sheet
Synonym:	Alpha-Cyano-Beta-Dimethylaminoacrylonitrile; ((Dimethylamino)methylene)malonitrile
CAS:	16849-88-0

Section 1 - Chemical Product MSDS Name:(Dimethylaminomethylene)Malononitrile Material Safety Data Sheet
Synonym:Alpha-Cyano-Beta-Dimethylaminoacrylonitrile; ((Dimethylamino)methylene)malonitrile

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
16849-88-0	(Dimethylaminomethylene)Malononitrile	ca 100	240-873-7

Hazard Symbols: XN
Risk Phrases: 20/21

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Harmful by inhalation and in contact with skin.The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Metabolism may release cyanide, which may result in headache, dizziness, weakness, collapse, unconsciousness and possible death.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. May be metabolized to cyanide which in turns act by inhibiting cytochrome oxidase impairing cellular respiration.
Chronic:
May be metabolized to cyanide which in turn acts by inhibiting cytochrome oxidase impairing cellular respiration.

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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.
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:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid. 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:

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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. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
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# 16849-88-0: 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: Powder
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 84.00 - 85.00 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:
Molecular Formula: C6H7N3
Molecular Weight: 121.14

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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.
Incompatibilities with Other Materials:
Strong acids, strong bases, strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 16849-88-0: OO3746000 LD50/LC50:
Not available.
Carcinogenicity:
(Dimethylaminomethylene)Malononitrile - 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: 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 Harmful by inhalation and in contact with
skin.
Safety Phrases:
S 23 Do not inhale gas/fumes/vapour/spray.
S 28A After contact with skin, wash immediately with
plenty of water.
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# 16849-88-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 16849-88-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 16849-88-0 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：

  (二甲基氨亚甲基)丙二腈 在 platinum(IV) oxide 盐酸 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、482.63 kPa 条件下， 反应 9.0h， 以34%的产率得到2-aminomethyl-N¹,N¹-dimethylpropane-1,3-diamine trihydrochloride
  参考文献：
  名称：

  Hydrogenation of Imino‐bisnitriles—Synthesis of Novel Triamines

  摘要：

  DOI：

  10.1080/00397910601038970
• 作为产物：
  描述：

  (2E)-3-(二甲基氨基)-2-甲酰基丙烯腈 在 1,2-二氯乙烷 作用下， 以 0-acetylhydroxylamine hydrochloride 为溶剂， 生成 (二甲基氨亚甲基)丙二腈
  参考文献：
  名称：

  Process for producing dialkyl aminoacrylonitrile

  摘要：

  通过在存在脱氢催化剂的情况下，用氢受体处理二甲基氨基丙腈来生产二烷基氨基丙烯腈的工艺。因此生产的二烷基氨基丙烯腈被转化为氨基亚甲基丙二腈，这是硫胺素的已知中间体。

  公开号：

  US03965141A1

文献信息

• Silver(I) Ion-Mediated Desulfurization-Condensation of Thiocarbonyl Compounds with Several Nucleophiles
  作者：Isao Shibuya、Yoichi Taguchi、Tohru Tsuchiya、Akihiro Oishi、Eisaku Katoh

  DOI：10.1246/bcsj.67.3048

  日期：1994.11

  desulfurization-condensation reaction was investigated in the presence of silver(I) salt for several kinds of thiocarbonyl compounds with nucleophiles. Such thiocarbonyl compounds as 4,4′-bis(dimethylamino)thiobenzophenone, ethylene trithiocarbonate, and N-(thiobenzoyl)morpholine react with malononitrile or other active methylene compounds in the presence of silver trifluoroacetate to afford the corresponding

  在银(I)盐存在下研究了几种硫代羰基化合物与亲核试剂的脱硫缩合反应。4,4'-双(二甲氨基)噻二苯甲酮、亚乙基三硫代碳酸酯和N-(硫代苯甲酰基)吗啉等硫代羰基化合物在三氟乙酸银存在下与丙二腈或其他活性亚甲基化合物反应，生成相应的烯烃化合物和硫化银。硫代羰基化合物与一些其他亲核试剂（如苯胺衍生物和乙二醇）的这种反应也得到了亚胺和 1,3-二氧戊环衍生物。
• 一种米力农的合成方法
  申请人：鲁南制药集团股份有限公司

  公开号：CN113493411A

  公开（公告）日：2021-10-12

  本发明公开了一种米力农的合成方法，属于药物合成技术领域。该方法以1‑(4‑吡啶基)‑2‑丙酮为原料与α‑(N,N‑二甲胺亚甲基)丙二腈反应，得类白色固体米力农。该合成米力农的方法，操作简便，收率高，适合工业化放大生产。所得米力农成品，外观及纯度均达到标准。
• 一种制备米力农的新工艺
  申请人：鲁南制药集团股份有限公司

  公开号：CN113493412A

  公开（公告）日：2021-10-12

  本发明公开了一种米力农的制备方法，属于药物合成技术领域。该方法以1‑(4‑吡啶基)‑2‑丙酮为原料与α‑(取代亚甲基)丙二氰在碱性条件下加热反应，得到米力农。该制备米力农的方法，操作简便，安全性高，收率高，适合工业化放大生产。所得米力农成品，外观及纯度均达到标准。
• Synthesis of new pyrazolo[1,5-<i>a</i>]pyrimidines and pyrazolo[3,4-<i>b</i>]pyridines
  作者：Saleh M. Al-Mousawi、Mohammad A. Mohammad、Mohamad H. Elnagdi

  DOI：10.1002/jhet.5570380430

  日期：2001.7

  While 3(5)-aminopyrazole reacts with enaminonitrile to yield pyrazolo[1,5-a]pyrimidines, 3-amino-5-pyrazolone reacts with the same reagents to yields pyrazolo[3,4-b]pyridines.

  3（5）-氨基吡唑与烯腈反应生成吡唑并[1,5- a ]嘧啶，而3-氨基-5-吡唑酮与相同的试剂反应生成吡唑并[3,4- b ]吡啶。
• Regioselectivity in the Reaction of 2‐Aminobenzothiazoles and 2‐Aminobenzimidazoles with Enaminonitriles and Enaminones: Synthesis of Functionally Substituted Pyrimido[2,1‐<i>b</i>][1,3]benzothiazole and Pyrimido[1,2‐<i>a</i>]benzimidazole Derivatives
  作者：Abdulaziz Alnajjar、Mervat Mohammed Abdelkhalik、Hossam Mohammed Riad、Samia Mohammed Sayed、Kamal Usef Sadek

  DOI：10.1002/jhet.3337

  日期：2018.12

  A variety of new polyfunctionally substituted benzo[d]pyrimido[2,1‐b][1,3]thiazole and benzo[4,5]imidazo[1,2‐a]pyrimidine derivatives have been synthesized. The general synthetic procedure used for this purpose involves the condensation of 2‐aminobenzothiazole and 2‐aminobenzimidazole with a variety of enaminonitriles, enaminones, and acrylaldehyde. The regioselectivity for initial attack of either

  各种新的多官能取代的苯并[ d ]嘧啶基[2,1– b ] [1,3]噻唑和苯并[4,5]咪唑[1,2- a ]已经合成了]嘧啶衍生物。用于该目的的一般合成方法涉及2-氨基苯并噻唑和2-氨基苯并咪唑与各种烯氨基腈，烯胺和丙烯醛的缩合。研究并合理化了对环内环氮或环外氨基的初始进攻的区域选择性。可以得出结论，环氮是酸性介质中反应性最强的分子，也可以分离出环状中间体，这证明了环化后的结论。然而，在碱性或中性介质中，发现环外氨基是反应性最高的中心。尽可能通过元素分析，光谱数据和替代合成路线阐明了新合成化合物的所有结构。

表征谱图