二氯丙二腈 | 13063-43-9

• 物质功能分类: 化学试剂 - 有机试剂 - 氰化物/腈
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 二氯丙二腈
• 中文别名: 2,2-二氯丙二腈
• 英文名称: dichloromalononitrile
• 英文别名: dichloromalonitrile；2,2-dichloropropanedinitrile
• CAS: 13063-43-9
• 化学式: C₃Cl₂N₂
• mdl: MFCD00001841
• 分子量: 134.952
• InChiKey: NCWGPYPDPWOJKC-UHFFFAOYSA-N

物化性质

• 沸点：
  97 °C(lit.)
• 密度：
  1.312 g/mL at 25 °C(lit.)
• 闪点：
  >230 °F
• 稳定性/保质期：
  在常温常压下稳定，应避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  6.1
• 危险品标志：
  T
• 安全说明：
  S26,S27,S37/39
• 危险类别码：
  R23/24/25
• WGK Germany：
  3
• 海关编码：
  2926909090
• 危险品运输编号：
  UN 2810 6.1/PG 2
• RTECS号：
  OO3740000
• 包装等级：
  III
• 危险类别：
  6.1
• 储存条件：
  常温下应存放在密闭容器中，并置于阴凉、通风和干燥处。

SDS

Name:	Dichloromalononitrile 97% Material Safety Data Sheet
Synonym:	Malononitrile, dichloro
CAS:	13063-43-9

Section 1 - Chemical Product MSDS Name:Dichloromalononitrile 97% Material Safety Data Sheet
Synonym:Malononitrile, dichloro

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
13063-43-9	Dichloromalononitrile	97	235-955-4

Hazard Symbols: T
Risk Phrases: 23/24/25

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Toxic by inhalation, in contact with skin and if swallowed.Lachrymator (substance which increases the flow of tears).Toxic.
Potential Health Effects
Eye:
Causes severe eye irritation. Lachrymator (substance which increases the flow of tears). May cause chemical conjunctivitis and corneal damage.
Skin:
Causes severe skin irritation.
Ingestion:
Harmful if swallowed. May cause gastrointestinal irritation with nausea, vomiting and diarrhea.
Inhalation:
May cause respiratory tract irritation. May cause burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, and vomiting.
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. Do NOT allow victim to rub eyes or keep eyes closed.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid immediately. 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 victim ingested or inhaled the substance; induce artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device.
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. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas.
Extinguishing Media:
In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant 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.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Do not get in eyes, on skin, or on clothing. Do not ingest or inhale. Use only in a chemical fume hood. Do not breathe vapor.
Storage:
Store in a cool, dry, well-ventilated area away from incompatible substances. Keep containers tightly closed.

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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# 13063-43-9: 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 and clothing to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Wear a NIOSH/MSHA or European Standard EN 149 approved full-facepiece airline respirator in the positive pressure mode with emergency escape provisions.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Clear liquid
Color: clear yellow
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 97 deg C @ 760.00mmHg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not applicable.
Flash Point: > 112 deg C (> 233.60 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water: Not available.
Specific Gravity/Density: 1.3120g/cm3
Molecular Formula: C3Cl2N2
Molecular Weight: 134.95

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

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 13063-43-9: OO3740000 LD50/LC50:
CAS# 13063-43-9: Draize test, rabbit, skin: 200 uL/24H Severe; Oral, rabbit: LD50 = >126 mg/kg; Oral, rat: LD50 = 130 mg/kg.
LD50: Oral, rat = 130 Carcinogenicity:
Dichloromalononitrile - 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 LIQUID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2810
Packing Group: II
IMO
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
Packing Group: II
RID/ADR
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
Packing group: II

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: T
Risk Phrases:
R 23/24/25 Toxic by inhalation, in contact with skin
and if swallowed.
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 13063-43-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 13063-43-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 13063-43-9 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：

  二氯丙二腈 在 fluorine 作用下， 生成 2,2-Dichlor-perfluor-(1,3-propandiamin)
  参考文献：
  名称：

  The Action of Elementary Fluorine upon Organic Compounds. XXVIII. The Direct Fluorination of Perhalonitriles

  摘要：

  DOI：

  10.1021/ja01063a034
• 作为产物：
  描述：

  dimethylsulfonium dicyanomethylide 在 二氯化二硫 作用下， 生成 二氯丙二腈
  参考文献：
  名称：

  Friedrich,K.; Rieser,J., Justus Liebigs Annalen der Chemie, 1976, p. 648 - 655

  摘要：

  DOI：

文献信息

• Construction of carbocycles initiated by Cu-catalyzed radical reaction of Cl2C(CN)2
  作者：Keisuke Masuda、Masashi Tanigawa、Masanori Nagatomo、Daisuke Urabe、Masayuki Inoue

  DOI：10.1016/j.tet.2017.03.063

  日期：2017.6

  A Cu-catalyzed radical reaction of Cl2C(CN)2 was utilized for stereoselective conversion of unsaturated molecules into functionalized carbocycles. Chloromalononitrile radicals, generated by treating Cl2C(CN)2 with catalytic amounts of CuCl and dppf in refluxing dioxane, intermolecularly reacted with the unsaturated bonds of acyclic or 10-membered compounds. The resultant carboradicals then intramolecularly

  利用Cu催化的Cl 2 C（CN）2自由基反应将不饱和分子立体选择性转化为功能化的碳环。通过在回流的二恶烷中用催化量的CuCl和dppf处理Cl 2 C（CN）2生成的氯丙二腈自由基，与无环或10元化合物的不饱和键发生分子间反应。然后将所得的碳硼化合物分子内加至另一个不饱和键以产生1，2-二取代的环戊烷或反式-十氢化萘衍生物。这些自由基级联反应的化学和立体选择性进行了详细讨论。
• Attachment of carbonyl functionalities onto olefins via copper-promoted radical reaction of dichloromethylcyanides
  作者：Shin Kamijo、Shinya Yokosaka、Masayuki Inoue

  DOI：10.1016/j.tet.2012.01.089

  日期：2012.7

  Chemo- and regioselective protocols for attachment of various carbonyl functionalities onto unactivated olefins have been developed. Atom transfer radical reactions of Cl3CCN, Cl2C(R)CN, and Cl2C(CN)2 were all promoted efficiently by a catalytic amount of CuCl and 1,1′-bis(diphenylphosphino)ferrocene to introduce chloromethylcyanide and chloride units to the C–C double bonds. Conversion of the chloromethylcyanide

  已经开发出用于将各种羰基官能团连接到未活化的烯烃上的化学和区域选择性方案。通过催化量的CuCl和1,1'-双（二苯基膦基）二茂铁引入氯甲基氰化物和三氯甲烷，可以有效地促进Cl 3 CCN，Cl 2 C（R）CN和Cl 2 C（CN）2的原子转移自由基反应。氯化物单元与CC双键。氯甲基氰化物向羰基官能团（例如，醛，酮和酯）的转化，以及随后通过消除HCl进行的双键重建，导致选择性地形成了羰基共轭的E-烯烃。
• Reactivity of Lewis acids towards nitriles; crystal structure and electron deformation density of C₂N₂·SbF₅and photoelectron spectrum of AsF₅
  作者：Inis C. Tornieporth-Oetting、Thomas M. Klapötke、T. Stanley Cameron、Jussi Valkonen、Paul Rademacher、Klaus Kowski

  DOI：10.1039/dt9920000537

  日期：——

  nitriles and dinitriles HCN, C2N2, CCl2(CN)2 and CH2(CN)2 towards AsF5 and SbF5 has been investigated. The new compounds HCN·AsF51, HCN·SbF52, C2N2·AsF53, C2N2·SbF54, CH2(CN)2·AsF55, CH2(CN)2·(2AsF5)6 and CCl2(CN)2·AsF57 have been characterized by chemical analysis, IR, Raman, 1H, 19F and 14N NMR spectroscopy. The crystal structure of the first example of a cyanogen adduct C2N2·SbF54 has been determined

  研究了腈和二腈HCN，C 2 N 2，CCl 2（CN）2和CH 2（CN）2对AsF 5和SbF 5的反应性。新化合物HCN·AsF 5 1，HCN·SbF 5 2，C 2 N 2 ·AsF 5 3，C 2 N 2 ·SbF 5 4，CH 2（CN）2 ·AsF 5 5，CH 2（CN）2 ·（2AsF 5）6和CCl 2（CN）2 ·AsF 5 7已通过化学分析，IR，拉曼，1 H，19 F和14 N NMR光谱进行了表征。已经确定了氰化物加合物C 2 N 2 ·SbF 5 4的第一实例的晶体结构。化合物4在正交晶空间群C 222 1中结晶，晶格参数为a = 6.579（1），b = 16.245（1）和c= 6.389（1）Å。检查了分子的变形密度。基于硬-软酸碱原理，讨论了HCN和C 2 N 2对强路易斯酸AsF 5的反应性。通过光电子能谱获得了迄今未知的AsF 5电离势（15.57
• Sequential ATRA/Reductive Cyclopropanation Reactions with a Ruthenium Catalyst in the Presence of Manganese
  作者：Mariano A. Fernández-Zúmel、Charlotte Buron、Kay Severin

  DOI：10.1002/ejoc.201100175

  日期：2011.4

  addition (ATRA) reactions of ethyl trichloroacetate, dichloromalononitrile, or diethyl 2,2-dichloromalonate with olefins followed by dechlorination have provided functionalized cyclopropanes in one step. The RuIII complex [Cp*RuCl2(PPh3)] was used as a catalyst precursor and commercial Mn powder as reducing agent. Reactions with the less activated substrate ethyl dichloroacetate gave ATRA products with

  三氯乙酸乙酯、二氯丙二腈或 2,2-二氯丙二酸二乙酯与烯烃的原子转移自由基加成 (ATRA) 反应，然后脱氯，在一个步骤中提供了官能化的环丙烷。RuIII配合物[Cp*RuCl2(PPh3)]用作催化剂前体和商业Mn粉末作为还原剂。与活性较低的底物二氯乙酸乙酯反应得到具有高转换数的 ATRA 产物，但未观察到环丙烷化。
• Ruthenium-Catalyzed Synthesis of 1,5-Dichlorides by Sequential Intermolecular Kharasch Reactions
  作者：Katrin Thommes、Mariano A. Fernández-Zúmel、Charlotte Buron、Aurélien Godinat、Rosario Scopelliti、Kay Severin

  DOI：10.1002/ejoc.201001213

  日期：2011.1

  Sequential intermolecular atom transfer radical addition reactions of activated dichlorides Cl2CRR′ (R = CN, CO2Et, R′ = H, CN, CO2Et) with two olefins catalyzed by [Cp*RuCl2(PPh3)] in the presence Mg allow the synthesis of linear 1,5-dichlorides. Different olefins can be employed in the first and in the second addition reaction. The reaction products are interesting synthetic precursors as demonstrated

  活化的二氯化物 Cl2CRR'（R = CN、CO2Et、R' = H、CN、CO2Et）与两种烯烃在 Mg 存在下由 [Cp*RuCl2(PPh3)] 催化的顺序分子间原子转移自由基加成反应允许合成线性1,5-二氯化物。在第一和第二加成反应中可以使用不同的烯烃。反应产物是有趣的合成前体，如通过镁诱导脱氯合成两种环戊烷所证明的。trans-3,4-diphenylcyclopentanecarbonitrile 的结构由单晶 X 射线衍射确定。

表征谱图