四正丁基锗 | 1067-42-1

• 物质功能分类: 有机原料 - 有机金属类化合物 - 有机锗
• 分子结构分类: 有机化合物 - 有机金属化合物
• 中文名称: 四正丁基锗
• 中文别名: 四丁基锗
• 英文名称: tetrabutylgermanium
• 英文别名: Tetrabutyl-german；Tetra-n-butylgerman；Tetra-n-butyl-germanium；Tetrabutylgermane
• CAS: 1067-42-1
• 化学式: C₁₆H₃₆Ge
• 分子量: 301.052
• InChiKey: HDVLQIDIYKIVRE-UHFFFAOYSA-N

物化性质

• 熔点：
  -74.1°C
• 沸点：
  >100 °C(lit.)
• 密度：
  0.93 g/mL at 25 °C(lit.)
• 闪点：
  >230 °F
• 介电常数：
  2.3300000000000001
• 稳定性/保质期：

  在常温常压下稳定，避免与酸接触以防止氧化。

计算性质

• 辛醇/水分配系数(LogP)：
  5.37
• 重原子数：
  17
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• TSCA：
  Yes
• 危险品标志：
  Xn
• 安全说明：
  S36
• 危险类别码：
  R20/21/22
• WGK Germany：
  3
• 海关编码：
  2931900090
• 储存条件：
  请将容器密封保存，并存放在阴凉、干燥处。

SDS

Name:	Tetrabutyl germanium Material Safety Data Sheet
Synonym:
CAS:	1067-42-1

Section 1 - Chemical Product MSDS Name:Tetrabutyl germanium Material Safety Data Sheet
Synonym:

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
1067-42-1	Tetrabutyl germanium		213-929-3

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
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.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

---

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.
Notes to Physician:

---

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.

---

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Provide ventilation.

---

Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation. 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.

---

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# 1067-42-1: 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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Liquid
Color: colorless
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: > 100 deg C
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: > 110 deg C (> 230.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density: .9300g/cm3
Molecular Formula: CH3(CH2)3!4Ge
Molecular Weight: 301.06

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Irritating and toxic fumes and gases.
Hazardous Polymerization: Not available.

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 1067-42-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Tetrabutyl germanium - 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
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
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# 1067-42-1: No information available.
Canada
CAS# 1067-42-1 is listed on Canada's NDSL List.
CAS# 1067-42-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 1067-42-1 is listed on the TSCA inventory.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

简介

四丁基锗是一种有机锗化合物，化学式为 (C4H9)4Ge，呈无色液态。

制备

四丁基锗可以类似四丁基硅的方式由四氯化锗和正丁基锂反应制得：

[ \text{GeCl}_4 + 4 , \text{LiC}_4\text{H}_9 \rightarrow \text{Ge(C}_4\text{H}_9\text{)}_4 + 4 , \text{LiCl} ]

反应信息

• 作为反应物：
  描述：

  四正丁基锗 在 二叔丁基过氧化物 作用下， 以 苯 为溶剂， 生成
  参考文献：
  名称：

  Clark, K. Brady; Griller, David, Organometallics, 1991, vol. 10, # 3, p. 746 - 750

  摘要：

  DOI：
• 作为产物：
  描述：

  溴丁基-镁 在 溴化锗 作用下， 生成 四正丁基锗
  参考文献：
  名称：

  Redistributions in Halogenosilanes and Alkylhalogenosilanes; Alkyliodochlorosilanes and Dimethylisocyanatochlorosilane

  摘要：

  DOI：

  10.1021/ja01156a098

文献信息

• Tributylgermanium hydride as a replacement for tributyltin hydride in radical reactionsElectronic supplementary information (ESI) available: full experimental details and data. See http://www.rsc.org/suppdata/ob/b3/b310520b/
  作者：W. Russell Bowman、Sussie L. Krintel、Mark B. Schilling

  DOI：10.1039/b310520b

  日期：——

  Tributylgermanium hydride (Bu(3)GeH) can be used as an alternative to tributyltin hydride (Bu(3)SnH) as a radical generating reagent with a wide range of radical substrates. Tributylgermanium hydride has several practical advantages over tributyltin hydride, e.g. low toxicity, good stability and much easier work-up of reactions. The reagent can be easily prepared in good yield and stored indefinitely

  氢化三丁基锗（Bu（3）GeH）可以用作氢化三丁基锡（Bu（3）SnH）的替代物，用作具有多种自由基底物的自由基发生剂。氢化三丁基锗比氢化三丁基锡具有多个实用优势，例如低毒性，良好的稳定性和更容易进行的反应后处理。该试剂可以容易地以高收率制备并且可以无限期地存储。合适的底物包括碘化物，溴化物，活化的氯化物，硒化苯基，叔硝基烷烃，硫代羰基咪唑啉化物和巴顿酯。烷基，乙烯基和芳基自由基可以在包括还原和环化过程在内的自由基反应中生成。可以使用常见的自由基引发剂，例如ACCN和三乙基硼烷。与Bu（3）SnH相比，Bu（3）GeH的碳中心自由基吸收氢的速度较慢，这有助于提高环化收率。苯硫醇的极性反转催化（PRC）可用于产生稳定的自由基中间体的反应，该中间体不会从Bu（3）GeH中提取氢。
• Novel alkylation of aromatic nitriles via photo-induced electron transfer of group 14 metal-carbon σ donors
  作者：Soichiro Kyushin、Yukihiro Masuda、Kazuhiro Matsushita、Yasuhiro Nakadaira、Mamoru Ohashi

  DOI：10.1016/s0040-4039(00)97074-6

  日期：——

  Photo-induced electron transfer reactions of tetraalkylsilanes, -germanes, and -stannanes with aromatic nitriles afforded alkylated products. The mechanism was investigated by use of a radical clock.

  四烷基硅烷，-锗烷和-锡烷与芳族腈的光诱导电子转移反应可得到烷基化产物。通过使用基本时钟来研究该机制。
• IR Spectra of <i>n</i>-Bu₄M (M = Si, Ge, Sn, Pb), <i>n</i>-BuAuPPh₃-<i>d</i>₁₅, and “<i>n</i>-Bu” on a Gold Surface
  作者：Jiří Kaleta、Lucie Bednárová、Martina Čížková、Jin Wen、Eva Kaletová、Josef Michl

  DOI：10.1021/acs.jpca.7b03404

  日期：2017.6.22

  and DFT-calculated IR spectra of n-Bu4M (M = Si, Ge, Sn, Pb), (CH3CH2CH213CD2)4Sn, and n-BuAuPPh3-d15 are reported and assigned. The asymmetric CH stretching vibration of the CH2 group adjacent to the metal atom appears as a distinct shoulder at ∼2934 cm–1, whereas for other CH2 groups it is located at ∼2922 cm–1. The characteristic peak at ∼2899 cm–1 is attributed to an overtone of a symmetric CH2 bend

  报告了n -Bu 4 M（M = Si，Ge，Sn，Pb），（CH 3 CH 2 CH 2 13 CD 2）4 Sn和n -BuAuPPh 3 - d 15的观察值和DFT计算的IR谱，并且已分配。与金属原子相邻的CH 2基团的不对称CH拉伸振动在〜2934 cm –1处表现为明显的肩峰，而对于其他CH 2基团，其位于〜2922 cm –1处。在〜2899 cm –1处的特征峰归因于对称CH 2的泛音在〜1445 cm –1处弯曲。在n -BuAuPPh 3 - d 15中，丁基的CH拉伸振动向较低的频率偏移约10 cm –1，并提供了两种可能的合理化方法。
• Donor-acceptor complexes of organometals and iodine. Alkyl ligands as probes for steric effects in charge transfer
  作者：S. Fukuzumi、J. K. Kochi

  DOI：10.1021/j100443a009

  日期：1980.3
• Reactivity of dianionic hexacoordinate germanium complexes toward organometallic reagents. A new route to organogermanes
  作者：G. Cerveau、C. Chuit、R. J. P. Corriu、C. Reye

  DOI：10.1021/om00051a049

  日期：1991.5

  Lithium and potassium tris(benzene-1,2-diolato)germanates (2a and 2b, respectively) and potassium tris(butane-2,3-diolato)germanate (3) are easily prepared from GeO2 in quantitative yields. They are very reactive toward organometallic reagents, the reactivity depending on the ligands on the germanium. Complexes 2 react with an excess of Grignard reagent to give the corresponding tetraorganogermanes R4Ge while the less reactive complex 3 leads to the functional triorganogermanes R3GeX. Tetraorganogermanes can also be prepared from complex 2b by reaction with organic bromides in the presence of Mg (Barbier reaction). The influence of Cp2TiCl2 and MgBr2 on the reactivity of Grignard reagents with these complexes was also investigated: in both cases formation of triorganogermanes was favored.

表征谱图