四甲基胍 | 80-70-6

• 物质功能分类: 化学试剂 - 有机试剂 - 胍盐
• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 四甲基胍
• 中文别名: N,N,N',N'-四甲基胍；1,1,3,3-四甲基胍；-四甲基胍；TMG
• 英文名称: N,N,N',N'-tetramethylguanidine
• 英文别名: 1,1,3,3-tetramethylguanidine；Tetramethylguanidine；TMG；N,N,N′,N′-tetramethylguanidine；1,1,3,3-tetramethylguanidin；N,N,N’,N’-tetramethylguanidine；1,1,3,3‐tetramethylguanidine
• CAS: 80-70-6
• 化学式: C₅H₁₃N₃
• mdl: MFCD00008323
• 分子量: 115.178
• InChiKey: KYVBNYUBXIEUFW-UHFFFAOYSA-N

物化性质

• 熔点：
  -30 °C
• 沸点：
  162-163 °C (lit.)
• 密度：
  0.916 g/mL at 20 °C (lit.)
• 闪点：
  140 °F
• 溶解度：
  可溶于乙腈（少许）、DMSO（少许）、甲醇（少许）
• 介电常数：
  23.100000000000001
• LogP：
  -0.49 at 20℃
• 物理描述：
  Liquid
• 稳定性/保质期：
  稳定，易燃，与强氧化剂、矿物酸和有机酸、二氧化碳不相容。空气敏感。

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  30.3
• 氢给体数：
  1
• 氢受体数：
  1

ADMET

毒理性

• 副作用

Dermatotoxin - 皮肤烧伤。

Dermatotoxin - Skin burns.

来源:Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

安全信息

• TSCA：
  Yes
• 危险等级：
  8
• 危险品标志：
  C
• 安全说明：
  S16,S26,S27,S36/37/39,S45
• 危险类别码：
  R20/22,R10,R34
• WGK Germany：
  1
• 海关编码：
  2942000000
• 危险品运输编号：
  UN 2920 8/PG 2
• 危险类别：
  8
• 包装等级：
  II
• 危险标志：
  GHS02,GHS05,GHS07
• 危险性描述：
  H226,H302,H314
• 危险性防范说明：
  P280,P305 + P351 + P338,P310
• 储存条件：
  2-8°C

SDS

Name:	1 1 3 3-Tetramethylguanidine 99% (gc) Material Safety Data Sheet
Synonym:	Non
CAS:	80-70-6

Section 1 - Chemical Product MSDS Name:1 1 3 3-Tetramethylguanidine 99% (gc) Material Safety Data Sheet
Synonym:Non

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
80-70-6	1,1,3,3-Tetramethylguanidine	99%	201-302-7

Hazard Symbols: C
Risk Phrases: 34

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Causes burns.Corrosive.
Potential Health Effects
Eye:
Causes eye burns.
Skin:
Causes skin burns.
Ingestion:
Causes gastrointestinal tract burns.
Inhalation:
Causes chemical burns to the respiratory tract. Inhalation may be fatal as a result of spasm, inflammation, edema of the larynx and bronchi, chemical pneumonitis and pulmonary edema.
Chronic:
Not available.

---

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 immediately. Immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Do not induce vomiting. If victim is conscious and alert, give 2-4 cupfuls of milk or water. Get medical aid immediately.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen.
Notes to Physician:
Treat as a caustic agent.

---

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. Will burn if involved in a fire.
Extinguishing Media:
In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam.

---

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.

---

Section 7 - HANDLING and STORAGE
Handling:
Use spark-proof tools and explosion proof equipment. Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Use only in a chemical fume hood.
Storage:
Keep away from sources of ignition. Store in a cool, dry place.
Store in a tightly closed container.

---

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 80-70-6: Personal Protective Equipment Eyes: Wear chemical goggles and a face shield if splashing is possible.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin.
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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: Not available.
Odor: Mild ammoniacal odor
pH: Not available.
Vapor Pressure: .26 hPa @ 25 deg C
Viscosity: mPas 20 deg C
Boiling Point: 160 - 162 deg C @ 760.00mm Hg
Freezing/Melting Point: <-30 deg C
Autoignition Temperature: 350 deg C ( 662.00 deg F)
Flash Point: 60 deg C ( 140.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: miscible with water
Specific Gravity/Density: .9180g/cm3
Molecular Formula: C5H13N3
Molecular Weight: 115.18

---

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.
Incompatibilities with Other Materials:
Strong oxidizing agents - strong acids - acid chlorides - acid anhydrides.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported.

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 80-70-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1,1,3,3-Tetramethylguanidine - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

---

Section 14 - TRANSPORT INFORMATION

IATA
Shipping Name: CORROSIVE LIQUID, FLAMMABLE, N.O.S.*
Hazard Class: 8 (3)
UN Number: 2920
Packing Group: II
IMO
Shipping Name: CORROSIVE LIQUID, FLAMMABLE, N.O.S.
Hazard Class: 8 (3)
UN Number: 2920
Packing Group: II
RID/ADR
Shipping Name: CORROSIVE LIQUID, FLAMMABLE, N.O.S.
Hazard Class: 8
UN Number: 2920
Packing group: II

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 34 Causes burns.
Safety Phrases:
S 25 Avoid contact with eyes.
S 36/37/39 Wear suitable protective clothing, 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# 80-70-6: 2
Canada
CAS# 80-70-6 is listed on Canada's DSL List.
CAS# 80-70-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 80-70-6 is listed on the TSCA inventory.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

用途

1,1,3,3-四甲基胍在有机合成中用作一种强的、非亲核碱，并且是一种高效、选择性的醇苯甲酰化催化剂。

理化性质

四甲基胍为无色油状液体，沸点160-162℃，密度0.918，折射率1.4692。它属于有机强碱，可溶于甲苯、环己酮、乙醇等，并且也可溶于水，在碱性水溶液中易水解为四甲基脲。这种物质具有腐蚀性，通常用镀锌铁桶包装。

应用 1. 医药行业

四甲基胍可用于合成新型抗生素头孢类药品的助溶剂，并主要用于头孢拉定等药品的合成。

2. 化工行业

此外，它也可作为聚氨基甲酸乙酯泡沫的催化剂。同时用于锦纶、羊毛及其他蛋白质的均染，以改善羊毛的耐用性。

制备 方法一

1. 首先使NaCN与Cl₂反应生成CNCl。
2. 然后与二甲胺、二甲胺盐酸盐在极性或非极性溶剂中进行反应，生成四甲基胍盐酸盐。
3. 最后再于水溶液中与强碱作用，并用有机溶剂萃取提纯制得四甲基胍。另一种方法是直接使四甲基胍盐酸盐在乙醇—乙醇钠溶液中反应制得四甲基胍。

方法二

1. 二甲胺水溶液与固体氰化钠混合后通氯气，反应结束后用三氯乙烯萃取，有机层为二甲氨基氰，水层为二甲胺盐酸盐和氰化钠。
2. 二甲氨基氰与二甲胺盐酸盐在极性溶剂（如硝基苯、异佛尔酮或苯乙醚等）中反应得四甲基胍盐酸盐。
3. 四甲基胍盐酸盐于水溶液中与强碱作用，并用有机溶剂萃取，提纯制得四甲基胍。

化学性质

四甲基胍为无色透明液体，广泛应用于医药及化工原料合成。在医药领域主要用于头孢类抗生素的生产。

用途

主要用作聚氨基甲酸乙酯泡沫的催化剂，并用于锦纶、羊毛及其他蛋白质的均染。

反应信息

• 作为反应物：
  描述：

  四甲基胍 在 氢碘酸 作用下， 生成 1,1,3,3-四甲基胍碘化物
  参考文献：
  名称：

  基于双发射一维有机-无机混合金属氯化物的白光发光二极管

  摘要：

  白光发射有机-无机杂化金属卤化物（MH）在固态照明中显示出有前景的潜在应用。由于用于白光发射的一维 (1D) MH 仍然很少见，并且卤素调节在用于宽带发射 (BE) 的 1D 混合 MH 中的关键作用尚未得到很好的确立，在此，我们报告了一系列 1D 混合 MH TMGPbX 3（TMG = 1,1,3,3-四甲基胍，X = Cl -，Br -或 I -）系统探索卤素对一维有机-无机杂化 MH 晶体结构和光致发光 (PL) 特性的影响。在紫外激发下，TMGPbBr 3和 TMGPbI 3表现出源自自陷激子（STEs）的BE，而TMGPbCl 3表现出特殊的蓝白色双重发射，这是由无机框架中的STEs和有机组分中的自由激子（FEs）贡献的。三个 1D MH 的不同发射机制得到了很好的证明和比较。凭借高达 11.67% 的 PL 量子产率（PLQY），制造了基于 TMGPbCl 3的白光发光二极管

  DOI：

  10.1021/acs.inorgchem.2c02085
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氨 、 水 作用下， 生成 四甲基胍
  参考文献：
  名称：

  549.甲基化胍的基本强度

  摘要：

  DOI：

  10.1039/jr9510002492
• 作为试剂：
  描述：

  苯乙烯 、 4-氰基吡啶 、 4-苯基-2-丁醇 在 C₂₁H₂₇N₂⁽¹⁺⁾*BF₄^(1-) 、 吡啶 、 3,4,5,6-Tetrakis(3,6-dibromocarbazol-9-yl)benzene-1,2-dicarbonitrile 、 四甲基胍 作用下， 以 甲基叔丁基醚 、 乙腈 为溶剂， 以95 %的产率得到4-(3-methyl-1,5-diphenylpentyl)pyridine
  参考文献：
  名称：

  醇、芳基烯烃和氰基吡啶的自由基脱氧三组分反应

  摘要：

  我们在此报道了在光氧化还原条件下涉及醇、芳基烯烃和氰基吡啶的脱氧自由基多组分反应。该方法是光氧化还原中性的，适合后期改性，并且与作为烷基自由基源的多种醇相容，包括伯醇、仲醇和叔醇。该反应包括自由基中继机制，包括烷基自由基对芳基烯烃进行吉斯加成，然后进行苄基自由基的脱氰基吡啶化。

  DOI：

  10.1021/acs.orglett.4c02150

文献信息

• Condensed-Phase, Halogen-Bonded CF₃I and C₂F₅I Adducts for Perfluoroalkylation Reactions
  作者：Filippo Sladojevich、Eric McNeill、Jonas Börgel、Shao-Liang Zheng、Tobias Ritter

  DOI：10.1002/anie.201410954

  日期：2015.3.16

  family of practical, liquid trifluoromethylation and pentafluoroethylation reagents is described. We show how halogen bonding can be used to obtain easily handled liquid reagents from gaseous CF3I and CF3CF2I. The synthetic utility of the new reagents is exemplified by a novel direct arene trifluoromethylation reaction as well as adaptations of other perfluoroalkylation reactions.

  描述了一系列实用的液体三氟甲基化和五氟乙基化试剂。我们展示了如何使用卤素键从气态CF 3 I和CF 3 CF 2 I获得易于处理的液体试剂。新试剂的合成效用以新颖的直接芳烃三氟甲基化反应以及对其他全氟烷基化反应的适应性为例。
• Copper-Catalyzed Synthesis of Pentasubstituted Pyridines from<i>N</i>-Sulfonyl Ketenimines, 1,1,3,3-Tetramethylguanidine, and Acetylene Dicarboxylates
  作者：Issa Yavari、Azam Sheikhi、Manijeh Nematpour、Zohreh Taheri

  DOI：10.1002/hlca.201400255

  日期：2015.4

  Regioselective synthesis of pentasubstituted pyridines has been developed in moderate‐to‐good yields by the reaction of sulfonyl azides, alkynes, and a dialkyl acetylenedicarboxylatetetramethylguanidine adduct catalyzed by CuI in MeCN at room temperature.

  CuI在室温下在MeCN中催化的磺酰叠氮化物，炔烃和乙二烯基二羧酸二alkyl基四甲基胍加合物的反应已开发出中等至良好收率的五取代吡啶区域选择性合成方法。
• Introducing the reversible chemistry of CO₂ with diols mediated by organic superbases into polycarbonate synthesis
  作者：Yang Chai、Qin Chen、Caijuan Huang、Qiang Zheng、Michael North、Haibo Xie

  DOI：10.1039/d0gc01197e

  日期：——

  The reversible reaction of CO₂ with alcohols mediated by organic superbases was firstly developed to be a toolbox for capturing CO₂ into polymerizable carbonate monomers applicable for thiol–ene click and ADMET polymerization to produce new libraries of polycarbonates.

  CO2与醇类通过有机超碱介导的可逆反应首次被开发成为一个工具箱，用于将CO2捕获到可聚合的碳酸酯单体中，适用于硫醇-烯烃点击和ADMET聚合，以生产新的聚碳酸酯库。
• Copper-Catalyzed Tandem Synthesis of Tetrasubstituted Pyrimidines from Alkynes, Sulfonyl Azides, Trichloroacetonitrile, and Tetramethylguanidine
  作者：Issa Yavari、Manijeh Nematpour

  DOI：10.1055/s-0032-1317951

  日期：——

  The synthesis of a novel class of pyrimidine derivatives via a copper-catalyzed tandem reaction of trichloroacetonitrile, 1,1,3,3-tetramethylguanidine, sulfonyl azides, and terminal alkynes is described.

  描述了通过三氯乙腈、1,1,3,3-四甲基胍、磺酰叠氮化物和末端炔烃的铜催化串联反应合成一类新型嘧啶衍生物。
• Copper-Catalyzed One-Pot Synthesis of Functionalized 1,4-Dihydroazete Derivatives from Sulfonyl Azides, Terminal Alkynes, and Tetramethylguanidine
  作者：Issa Yavari、Manijeh Nematpour

  DOI：10.1055/s-0032-1317075

  日期：——

  Ketenimine intermediates generated by the addition of copper acetylides to sulfonyl azides are trapped by tetramethyl­guanidine to afford 1,4-dihydro- N , N -dimethyl-3-aryl(alkyl)-4-­aryl(alkyl)sulfoniminoazet-2-amine derivatives in moderate to good yields.

  通过将铜炔化物与磺酰叠氮化物加成而产生的酮亚胺中间体被四甲基胍捕获，以在中等至良好的产量。

表征谱图