二异丙基氨腈 | 3085-76-5

• 物质功能分类: 化学试剂 - 有机试剂 - 酰胺
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 二异丙基氨腈
• 英文名称: diisopropylcyanamide
• 英文别名: N,N-diisopropylcyanamide；di(propan-2-yl)cyanamide
• CAS: 3085-76-5
• 化学式: C₇H₁₄N₂
• mdl: MFCD00008865
• 分子量: 126.202
• InChiKey: DGCUISYKMONQDH-UHFFFAOYSA-N

物化性质

• 熔点：
  -27°C(lit.)
• 沸点：
  93-94 °C25 mm Hg(lit.)
• 密度：
  0.839 g/mL at 25 °C(lit.)
• 闪点：
  174 °F

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.857
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S26,S27,S36/37/39
• 危险类别码：
  R20/21/22,R36/37/38
• WGK Germany：
  3
• 储存条件：
  | 室温 |

SDS

Name:	Diisopropylcyanamide 97+% Material Safety Data Sheet
Synonym:	None known
CAS:	3085-76-5

Section 1 - Chemical Product MSDS Name:Diisopropylcyanamide 97+% Material Safety Data Sheet
Synonym:None known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
3085-76-5	Diisopropylcyanamide	97+	221-401-9

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.
Potential Health Effects
Eye:
May cause eye irritation. May cause chemical conjunctivitis and corneal damage.
Skin:
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.
Inhalation:
The toxicological properties of this substance have not been fully investigated. Aspiration may lead to pulmonary edema. Inhalation at high concentrations may cause CNS depression and asphixiation.
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.
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.
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. Use water spray to keep fire-exposed containers cool. Water may be ineffective.
Material is lighter than water and a fire may be spread by the use of water. Combustible liquid. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas.
Containers may explode when heated.
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:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Avoid runoff into storm sewers and ditches which lead to waterways. Clean up spills immediately, observing precautions in the Protective Equipment section. Remove all sources of ignition. Use a spark-proof tool. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation. 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. Do not pressurize, cut, weld, braze, solder, drill, grind, or expose empty containers to heat, sparks or open flames.
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.

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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# 3085-76-5: 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: off-white
Odor: amine-like
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 93 - 94 deg C @ 25.00mm Hg
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: 78 deg C ( 172.40 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: .8390g/cm3
Molecular Formula: C7H14N2
Molecular Weight: 126.20

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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, ignition sources, excess heat.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, 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# 3085-76-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Diisopropylcyanamide - 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 LIQUID, ORGANIC, N.O.S.*
Hazard Class: 6.1
UN Number: 2810
Packing Group: III
IMO
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
Packing Group: III
RID/ADR
Shipping Name: TOXIC LIQUID, ORGANIC, N.O.S.
Hazard Class: 6.1
UN Number: 2810
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# 3085-76-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 3085-76-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 3085-76-5 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：

  二异丙基氨腈 在 盐酸 作用下， 以89%的产率得到1,1-二异丙基脲
  参考文献：
  名称：

  Malik, Abdul; Afza, Nighat; Siddiqui, Salimuzzaman, Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1982, vol. 37, # 4, p. 512 - 518

  摘要：

  DOI：
• 作为产物：
  描述：

  aluminium trichloride-diisopropylcyanamide 生成 二异丙基氨腈
  参考文献：
  名称：

  Jochims, Johannes C.; Abu-El-Halawa, Rajab; Zsolnai, Laszlo, Chemische Berichte, 1984, vol. 117, # 3, p. 1161 - 1177

  摘要：

  DOI：
• 作为试剂：
  描述：

  对甲氧基苯氧乙酸 在 4-二甲氨基吡啶 、 二异丙基氨腈 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Polymeric salen-Ti(IV) or V(V) complex catalyzed asymmetric synthesis of O-acetylcyanohydrins from KCN, Ac2O and aldehydes

  摘要：

  Polymeric salen-Ti(IV) and V(V) complexes were employed in the enantioselective O-acetyl cyanation of aldehydes with potassium cyanide and acetic anhydride. The crosslinked polymeric salen-Ti(IV) catalyst exhibited good activities and enantioselectivities, up to 91 % ee with 99 % conversion was obtained at -20degreesC with 1 mol % of catalyst (based on bimetallic catalytic unit). Moreover, six consecutive recyclings with the easily recovered crosslinked polymeric catalyst showed no obvious decrease in either activity or enantioselectivity. Linear polymeric salen-V(V) catalyst showed good catalytic efficiency too, up to 94 % ee with 99 % conversion was obtained at -42degreesC with 5 mol % of catalyst. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.08.078

文献信息

• Ru/C: a simple heterogeneous catalyst for the amination of azoles under ligand free conditions
  作者：K. Harsha Vardhan Reddy、B. S. P. Anil Kumar、V. Prakash Reddy、R. Uday Kumar、Y. V. D. Nageswar

  DOI：10.1039/c4ra05447d

  日期：——

  A ligand free Ru/C-catalyzed amination of 2-halo azoles with a broad scope of aminating reagents has been developed. Utilizing this protocol a variety of 2-aminoazole derivatives were synthesized in moderate to good yields. The methodology is operationally simple and it provides potentially useful products by using an inexpensive recyclable catalytic system.

  使用无配体的Ru/C催化剂对2-卤代唑类化合物进行胺化反应，可以使用广泛的胺化试剂。利用这一方法合成了多种2-氨基唑类衍生物，产率在中等到良好之间。该方法操作简单，并且通过使用廉价可回收的催化体系提供了潜在有用的产物。
• Formation of Acyl-Substituted Nitrile Ylides by Rh₂(OAc)₄-Catalyzed Decomposition of<i>α</i>-Diazocarbonyl Compounds in Nitriles
  作者：Kazuaki Fukushima、Toshikazu Ibata

  DOI：10.1246/bcsj.68.3469

  日期：1995.12

  The Rh2(OAc)4-catalyzed reactions of α-diazocarbonyl compounds in nitrile in the presence of dimethyl acetylenedicarboxylate (DMAD) gave oxazole and pyrrole derivatives. The formation of the oxazole derivatives is explained in terms of the 1,5-cyclization of an acyl-substituted nitrile ylide intermediate, and the formation of the pyrrole derivatives is explained by the 1,3-dipolar cycloaddition of

  在乙炔二羧酸二甲酯 (DMAD) 存在下，α-重氮羰基化合物在腈中的 Rh2(OAc)4 催化反应得到恶唑和吡咯衍生物。恶唑衍生物的形成通过酰基取代的腈叶立德中间体的 1,5-环化来解释，吡咯衍生物的形成通过相同中间体与 DMAD 的 1,3-偶极环加成来解释。酰基取代的腈叶立德与丙炔酸甲酯的环加成反应的区域化学表明，丙炔基型共振结构的贡献在酰基取代的腈叶立德反应中起重要作用。
• Synthesis of Cyanamides from Cyanogen Bromide under Mild Conditions through N-Cyanation of Allylic Tertiary Amines
  作者：Chenghui Sun、Honggang Liang、Lingxiang Bao、Yao Du、Yiying Zhang、Siping Pang

  DOI：10.1055/s-0036-1588533

  日期：2017.12

  Cyanamides were selectively formed through a one-step nucleophilic substitution reaction of allylic tertiary amines with cyanogen bromide. Because of the mild reaction conditions and good yields of the reaction, as well as the commercial availability of the starting materials, this new method represents a valuable tool for the synthesis of cyan­amides through an N-deallylation reaction and an N-cyanation

  通过烯丙基叔胺与溴化氰的一步亲核取代反应选择性地形成氰胺。由于反应条件温和，反应收率良好，以及起始原料的商业可用性，这种新方法代表了通过 N-脱烯丙基化反应和 N-氰化反应合成氰胺的一种有价值的工具。锅。
• Prototropy in the System -ClCH-N=N-; Cycloadditions of 1-Aza-2-azoniaallene Cations Derived from Aldehydes
  作者：Yiping Guo、Quanrui Wang、Johannes C. Jochims

  DOI：10.1055/s-1996-4189

  日期：1996.2

  1,3-Disubstituted 1-aza-2-azoniaallene salts 10 were obtained as reactive intermediates on oxidation of aldehyde hydrazones 7 with tert-butyl hypochlorite and treatment of the resulting (1-chloroalkyl)azo compounds 8 with a Lewis acid (SbCl5). The allenes 10 underwent cycloadditions to the multiple bonds of nitriles, acetylenes, and olefins affording the heterocyclic salts 12, which gave the free bases 12’ with aqueous NaOH. The critical point of this sequence lies in the prototropic rearrangement of 8 into the hydrazonyl chlorides 9, from which no heterocumulenes 10 could be obtained. However, further chlorination of 7c led to the (1,1-dichloropropyl)azo compound 13, which gave the chloro substituted allenium salt 14 on treatment with SbCl5. Cycloaddition of 14 to acetonitrile afforded the chloro substituted 1,2,4-triazolium salt 16. Conditions for slow rearrangements 8 → 9 were found for compounds 8 derived from primary or secondary alkanecarbaldehydes. However, for (1-chloroalkyl)azo compounds derived from benzaldehyde or pivaldehyde the prototropy 8 → 9 was too fast to permit preparation of heterocumulenes 10.

  1,3-二取代的1-氮-2-氮杂烯盐10作为活性中间体,通过醛肼7在叔丁基次氯酸酯氧化下制得,并对生成的(1-氯烷基)偶氮化合物8用路易斯酸(SbCl5)处理.烯盐10经与腈、炔烃、或烯烃的复分解反应得到含氮盐12,用NaOH水溶液处理即得到自由碱12'.本反应历程的关键点在于8向肼叉基氯化物9的质子迁移,而从9不能得到含异氰化合物10.而7c的进一步氯化导致(1,1-二氯丙基)偶氮化合物13生成,用SbCl5处理得到氯取代的烯盐14,与乙腈的复分解反应得到氯取代的1,2,4-三氮唑盐16.在由伯或仲脂肪醛衍生的(1-氯烷基)偶氮化合物8中,发现了缓慢的8-9重排反应,但对于由苯甲醛或新戊醛衍生的(1-氯烷基)偶氮化合物8而言,8-9重排过快,无法制得含异氰化合物10.
• 一种由烯丙基叔胺类化合物一步合成氰基叔 胺类化合物的方法
  申请人：北京理工大学

  公开号：CN106938990B

  公开（公告）日：2019-09-17

  本发明涉及一种由烯丙基叔胺类化合物一步合成氰基叔胺类化合物的方法，属于有机合成方法技术领域。所述方法具体合成过程为：在密闭反应环境中，向无水有机溶剂中加入溴化氰，在惰性气体保护下，再向溶液中逐滴加入烯丙基叔胺类化合物，得到烯丙基叔胺类化合物浓度为0.8～1mol/L的溶液，在室温下反应16～24小时之后，经过柱色谱分离纯化，得到相应的一种氰基叔胺类化合物。该方法摒弃了昂贵的脱烯丙基化催化剂的使用，合成步骤少，原料易得，价格低廉，反应条件温和，操作简单，易于工艺化和工业化。产率在50％‑80％之间。

表征谱图