二甲基氯化铝 | 1184-58-3

• 物质功能分类: 有机原料 - 有机金属类化合物 - 有机铝
• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机过渡后金属化合物
• 中文名称: 二甲基氯化铝
• 英文名称: dimethylaluminum chloride
• 英文别名: dimethylaluminium chloride；AlMe₂Cl；Me₂AlCl；DMAC；chlorodimethylaluminum；dimethylaluminum monochloride；Dimethylalumanylium chloride；dimethylalumanylium;chloride
• CAS: 1184-58-3
• 化学式: C₂H₆AlCl
• 分子量: 92.5042
• InChiKey: JGHYBJVUQGTEEB-UHFFFAOYSA-M

物化性质

• 熔点：
  -21°C
• 沸点：
  126-127°C
• 密度：
  0.701 g/mL at 25 °C
• 闪点：
  −1 °F
• 物理描述：
  Liquid
• 稳定性/保质期：
  常温常压下稳定，但对光敏感，会吸收空气中的水分。因此应避免与不相容材料、水、潮湿空气接触。 与强氧化剂、水、酸、醇、氧、有机卤化物以及水分反应。

计算性质

• 辛醇/水分配系数(LogP)：
  1.48
• 重原子数：
  4
• 可旋转键数：
  0
• 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

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：
  No
• 危险等级：
  4.2
• 危险品标志：
  F,C
• 安全说明：
  S16,S26,S27,S45
• 危险类别码：
  R14/15
• WGK Germany：
  2
• 海关编码：
  2903199000
• 危险品运输编号：
  UN 3394 4.2/PG 1
• 危险类别：
  4.2
• 包装等级：
  I
• 危险标志：
  GHS02,GHS05,GHS07,GHS08,GHS09
• 危险性描述：
  H225,H250,H260,H304,H314,H336,H361f,H373,H411
• 危险性防范说明：
  P201,P231 + P232,P280,P305 + P351 + P338,P370 + P378,P422
• 储存条件：
  密封储存，存放在阴凉干燥的库房中。应远离火源、易燃易爆区域和腐蚀性物质以及水源。常用氮气进行保护。

SDS

Version 1.4
Regulation (EC) No 1907/2006

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1 - Product and Company Information

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Product Name DIMETHYLALUMINUM CHLORIDE, 1.0M
SOLUTION IN HEXANES

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2 - Hazards Identification

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SPECIAL INDICATION OF HAZARDS TO HUMANS AND THE ENVIRONMENT
Reacts violently with water, liberating extremely flammable gases.
Spontaneously flammable in air. Toxic by inhalation, in contact
with skin and if swallowed. Causes burns.

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3 - Composition/Information on Ingredients

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Product Name CAS # EC no Annex I
Index Number
DIMETHYLALUMINUM CHLORIDE, 1.0M None None None
SOLUTION IN HEXANES
Formula C2H6AlCl
Molecular Weight 92,5100 AMU

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4 - First Aid Measures

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AFTER INHALATION
If inhaled, remove to fresh air. If not breathing give
artificial respiration. If breathing is difficult, give oxygen.
AFTER EYE CONTACT
Assure adequate flushing of the eyes by separating the eyelids
with fingers.
AFTER INGESTION
If swallowed, wash out mouth with water provided person is
conscious. Call a physician immediately.

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5 - Fire Fighting Measures

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CONDITIONS OF FLAMMABILITY
Reacts with water to liberate flammable and/or explosive gas.
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Catches fire if exposed to air.
EXTINGUISHING MEDIA
Suitable: Dry chemical powder.
Unsuitable: Do not use water.
Explosion Hazards: Container explosion may occur under fire
conditions.
SPECIAL PROTECTIVE EQUIPMENT FOR FIREFIGHTERS
Wear self-contained breathing apparatus and protective clothing
to prevent contact with skin and eyes.
SPECIFIC METHOD(S) OF FIRE FIGHTING
Use water spray to cool fire-exposed containers.

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6 - Accidental Release Measures

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PERSONAL PRECAUTION PROCEDURES TO BE FOLLOWED IN CASE OF LEAK OR SPILL
Evacuate area. Shut off all sources of ignition.
PROCEDURE(S) OF PERSONAL PRECAUTION(S)
Wear self-contained breathing apparatus, rubber boots, and heavy
rubber gloves.
METHODS FOR CLEANING UP
Cover with dry-lime, sand, or soda ash. Place in covered
containers using non-sparking tools and transport outdoors.
Ventilate area and wash spill site after material pickup is
complete.

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7 - Handling and Storage

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HANDLING
Directions for Safe Handling: Do not get in eyes, on skin, on
clothing. Do not breathe vapor.
STORAGE
Conditions of Storage: Keep tightly closed. Keep away from heat,
sparks, and open flame. Store in a cool dry place.
Incompatible Materials: Do not allow contact with water
SPECIAL REQUIREMENTS: Air sensitive.

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8 - Exposure Controls / Personal Protection

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ENGINEERING CONTROLS
Safety shower and eye bath. Use only in a chemical fume hood.
GENERAL HYGIENE MEASURES
Wash thoroughly after handling.
PERSONAL PROTECTIVE EQUIPMENT
Respiratory Protection: Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US)
or CEN (EU). Where risk assessment shows air-purifying respirators
are appropriate use a dust mask type N95 (US) or type P1 (EN 143)
respirator.
Hand Protection: Wear heavy rubber gloves.
Eye Protection: Chemical safety goggles.
Special Protective Measures: Impervious protective clothing.
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Faceshield (8-inch minimum).

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9 - Physical and Chemical Properties

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pH N/A
BP/BP Range N/A
MP/MP Range N/A
Flash Point - 18,000 °C. Method: closed cup
Flammability N/A
Autoignition Temp N/A
Oxidizing Properties N/A
Explosive Properties N/A
Explosion Limits N/A
Vapor Pressure N/A
SG/Density 0,7010 g/cm3
Partition Coefficient N/A
Viscosity N/A
Vapor Density N/A
Saturated Vapor Conc. N/A
Evaporation Rate N/A
Bulk Density N/A
Decomposition Temp. N/A
Solvent Content N/A
Water Content N/A
Surface Tension N/A
Conductivity N/A
Miscellaneous Data N/A
Solubility N/A

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10 - Stability and Reactivity

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STABILITY
Conditions to Avoid: Moisture.
Materials to Avoid: Oxygen, Oxidizing agents, Alcohols, Acids
Reacts violently with water.
HAZARDOUS DECOMPOSITION PRODUCTS
Hazardous Decomposition Products: Hydrogen chloride gas, Aluminum
oxide Carbon monoxide, Carbon dioxide.

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11 - Toxicological Information

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SIGNS AND SYMPTOMS OF EXPOSURE
Symptoms of exposure may include burning sensation, coughing,
wheezing, laryngitis, shortness of breath, headache, nausea, and
vomiting. Inhalation may result in spasm, inflammation and edema
of the larynxand bronchi, chemical pneumonitis, and pulmonary
edema. Material is extremely destructive to tissue of the mucous
membranes and upper respiratory tract, eyes, and skin.
Neurotoxic effects. Warning: contains n-hexane (CAS#110-54-3) a
suspected neurotoxin.
ROUTE OF EXPOSURE
Multiple Routes: Harmful if swallowed, inhaled, or absorbed
through skin. Causes burns.

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12 - Ecological Information

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No data available.

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13 - Disposal Considerations

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SUBSTANCE DISPOSAL
Place the material which has been previously covered or mixed with
dry sand, lime, or soda ash in a large metal pan outdoors. Slowly
add portions of dry butanol until reaction ceases. Cautiously add
water from a distance until material has been flooded completely.
Observe all federal, state, and local environmental regulations.

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14 - Transport Information

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RID/ADR
UN#: 3394
Class: 4.2
PG: I
Subrisk: 4.3
Proper Shipping Name: Organometallic substance,
liquid, pyrophoric, water-reactive
IMDG
UN#: 3394
Class: 4.2
PG: I
Subrisk: 4.3
Proper Shipping Name: Organometallic substance,
liquid, pyrophoric, water-reactive
Marine Pollutant: No
Severe Marine Pollutant: No
Technical Name: Required
IATA
UN#: 3394
Class: 4.2
PG: I
Subrisk: 4.3
Proper Shipping Name: Organometallic substance,
liquid, pyrophoric, water-reactive
Inhalation Packing Group I: No
Technical Name: Required

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15 - Regulatory Information

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CLASSIFICATION AND LABELING ACCORDING TO EU DIRECTIVES
INDICATION OF DANGER: F-C
Highly Flammable. Corrosive.
R-PHRASES: 14/15-17-23/24/25-34
Reacts violently with water, liberating extremely flammable
gases. Spontaneously flammable in air. Toxic by inhalation, in
contact with skin and if swallowed. Causes burns.
S-PHRASES: 16-26-36/37/39-45
Keep away from sources of ignition - no smoking. In case of
contact with eyes, rinse immediately with plenty of water and
seek medical advice. Wear suitable protective clothing, gloves,
and eye/face protection. In case of accident or if you feel
unwell, seek medical advice immediately (show the label where
possible).
Caution: Substance not yet fully tested (EU).

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16 - Other Information
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WARRANTY
The above information is believed to be correct but does not
purport to be all inclusive and shall be used only as a guide. The
information in this document is based on the present state of our
knowledge and is applicable to the product with regard to
appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Inc.,
shall not be held liable for any damage resulting from handling or
from contact with the above product. See reverse side of invoice
or packing slip for additional terms and conditions of sale.
Copyright 2010 Co. License granted to make
unlimitedpaper copies for internal use only.
DISCLAIMER
For R&D use only. Not for drug, household or other uses.
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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  二甲基氯化铝 在 mercury dichloride 作用下， 以 苯 为溶剂， 生成 氯化甲基汞
  参考文献：
  名称：

  Eckstein, Z.; Dahlig, W.; Hetnarski, B., Przemysl Chemiczny, 1960, vol. 39, p. 225 - 228

  摘要：

  DOI：
• 作为产物：
  描述：

  甲基二氯化铝 生成 二甲基氯化铝
  参考文献：
  名称：

  Preparation of Methylaluminum Chlorides

  摘要：

  DOI：

  10.1021/ja01276a504
• 作为试剂：
  描述：

  (S)-3-(boc-氨基)-1-氯-2-丁酮 在 三乙基硅烷 、 copper(l) iodide 、 四(三苯基膦)钯 、 正丁基锂 、 二(三甲基铝)-1,4-二氮杂二环[2.2.2]辛烷加合物 、 ketoreductase 、 三氟化硼乙醚 、 二甲基氯化铝 、 三乙胺 、 C₂₁H₂₈N₇O₁₇P₃^(2-)*2Na⁽¹⁺⁾ 、 三氟乙酸 、 platinum(II) chloride 、 sodium hydroxide 、 magnesium chloride 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 aq. phosphate buffer 、 二氯甲烷 、 水 、 异丙醇 、 甲苯 为溶剂， 反应 88.08h， 生成
  参考文献：
  名称：

  临床候选药物 PF-06648671 的发现：一种用于治疗阿尔茨海默病的有效 γ-分泌酶调节剂

  摘要：

  在此，我们描述了用于治疗阿尔茨海默病的γ-分泌酶调节剂（GSM）临床候选物PF-06648671（ 22 ）的设计和合成。该设计的一个关键组成部分涉及 2,5-顺式四氢呋喃 (THF) 连接体，以赋予构象刚性并将化合物锁定为假定的生物活性构象。这项工作是使用药效团模型来指导的，因为在这项工作时还没有膜结合 γ-分泌酶蛋白复合物的晶体学信息。 PF-06648671 实现了全细胞体外效力 (Aβ42 IC 50 = 9.8 nM) 和吸收、分布、代谢和排泄 (ADME) 参数的出色对齐。这在临床前物种中产生了良好的体内药代动力学 (PK) 曲线，并且 PF-06648671 实现了适合每天一次给药的人体 PK 曲线。此外，PF-06648671被发现在啮齿类动物中具有良好的大脑可用性，这转化为人类中良好的中枢暴露和脑脊液（CSF）中β淀粉样蛋白（Aβ）42的显着减少。

  DOI：

  10.1021/acs.jmedchem.4c00580

文献信息

• Novel 11-hydroxy-9-keto-5,6-cis-13,14-cis-prostadienoic acid derivatives
  申请人：American Cyanamid Company

  公开号：US04123456A1

  公开（公告）日：1978-10-31

  This disclosure describes certain 11-hydroxy and 11-deoxy-9-keto(or hydroxy)-prostanoic acid derivatives useful as bronchodilators, hypotensive agents, anti-ulcer agents, or as intermediates.

  这份披露描述了某些11-羟基和11-去氧-9-酮（或羟基）-前列腺酸衍生物，可用作支气管扩张剂、降压剂、抗溃疡剂或中间体。
• The Exceptional Chelating Ability of Dimethylaluminum Chloride and Methylaluminum Dichloride. The Merged Stereochemical Impact of α- and β-Stereocenters in Chelate-Controlled Carbonyl Addition Reactions with Enolsilane and Hydride Nucleophiles
  作者：David A. Evans、Brett D. Allison、Michael G. Yang、Craig E. Masse

  DOI：10.1021/ja011337j

  日期：2001.11.1

  beta-disubstituted aldehydes concludes that the syn aldehyde diastereomer possesses the arrangement of stereocenters wherein the alpha- and beta-substituents impart a reinforcing facial bias upon the aldehyde carbonyl. Aldol reactions of syn aldehydes were thus observed to proceed with uniformly excellent diastereofacial selectivity. Aldol reactions of the corresponding anti aldehydes containing opposing

  介绍了在有利于螯合控制的条件下进行的非手性未取代烯醇硅烷和手性 β-羟基醛的路易斯酸促进 (Mukaiyama) 羟醛反应的立体选择性的系统研究。β-烷氧基和β-甲硅烷氧基醛的烯醇硅烷醛醇反应可以实现良好的立体控制，仅带有一个α-或β-立体中心。对α,β-二取代醛的螯合中间体的检查得出结论，syn 醛非对映异构体具有立体中心的排列，其中α-和β-取代基赋予醛羰基增强的面偏向性。因此观察到合成醛的羟醛反应以均匀优异的非对映面选择性进行。
• Formation of Quaternary Stereogenic Centers by Copper-Catalyzed Asymmetric Conjugate Addition Reactions of Alkenylaluminums to Trisubstituted Enones
  作者：Daniel Müller、Alexandre Alexakis

  DOI：10.1002/chem.201302856

  日期：2013.11.4

  undergo asymmetric copper‐catalyzed conjugate addition (ACA) to β‐substituted enones allowing the formation of stereogenic all‐carbon quaternary centers. Phosphinamine–copper complexes proved to be particularly active and selective compared with phosphoramidite ligands. After extensive optimization, high enantioselectivities (up to 96 % ee) were obtained for the addition of alkenylalanes to β‐substituted

  烯基铝经过不对称的铜催化共轭加成（ACA）至β取代的烯酮，从而形成立体立体的全碳四元中心。与亚磷酰胺配体相比，膦胺-铜络合物被证明具有特别的活性和选择性。经过广泛的优化后，将烯基丙氨酸添加到β-取代的烯酮中获得了很高的对映选择性（高达ee的96％  ）。为了产生芳基和烷基取代的烯基亲核试剂，探索了两种生成必需的烯基铝的策略。此外，首次将烷基取代的次膦胺（SimplePhos）配体鉴定为Cu催化的ACA的高效配体。
• Synthesis of 2-Substituted Propenes by Bidentate Phosphine-Assisted Methylenation of Acyl Fluorides and Acyl Chlorides with AlMe₃
  作者：Xiu Wang、Zhenhua Wang、Yuya Asanuma、Yasushi Nishihara

  DOI：10.1021/acs.orglett.9b01059

  日期：2019.5.17

  methylenation of acyl fluorides and acyl chlorides with substituted with aryl, alkenyl, and alkyl groups trimethylaluminum afforded an array of 2-substituted propene derivatives. The addition of a catalytic amount of DPPM increased an efficiency of the reactions. Trimethylaluminum as the methylenation reagent not only eliminates the presynthesis of methylene transfer reagent, but provides an efficient method for

  芳基，烯基和烷基三甲基铝取代的酰氟和酰氯的双膦膦化亚甲基化提供了一系列2取代的丙烯衍生物。催化量的DPPM的添加提高了反应效率。三甲基铝作为亚甲基化试剂，不仅消除了亚甲基转移试剂的预合成，而且为合成一系列2-取代的丙烯提供了一种有效的方法。
• Application of molybdenum bis(imido) complexes in ethylene dimerisation catalysis
  作者：William R. H. Wright、Andrei S. Batsanov、Antonis M. Messinis、Judith A. K. Howard、Robert P. Tooze、Martin J. Hanton、Philip W. Dyer

  DOI：10.1039/c2dt12061e

  日期：——

  In combination with EtAlCl2 (Mo : Al = 1 : 15) the imido complexes [MoCl2(NR)(NR′)(dme)] (R = R′ = 2,6-Pri2–C6H3 (1); R = 2,6-Pri2–C6H3, R′ = But (3); R = R′ = But (4); dme = 1,2-dimethoxyethane) and [Mo(NHBut)2(NR)2] (R = 2,6-Pri2–C6H3 (5); R = But (6)) each show moderate TON, activity, and selectivity for the catalytic dimerisation of ethylene, which is influenced by the nature of the imido substituents. In contrast, the productivity of [MoCl2(NPh)2(dme)] (2) is low and polymerisation is favoured over dimerisation. Catalysis initiated by complexes 1–4 in combination with MeAlCl2 (Mo : Al = 1 : 15) exhibits a significantly lower productivity. Reaction of complex 5 with EtAlCl2 (2 equiv.) gives rise to a mixture of products, while addition of MeAlCl2 affords [MoMe2(N–2,6-Pri2–C6H3)2]. Treatment of 6 with RAlCl2 (2 equiv.) (R = Me, Et) yields [Mo(μ-N–But}AlCl2)2] (7) in both cases. Imido derivatives 1 and 3 react with Me3Al and MeAlCl2 to form the bimetallic complexes [MoMe2(NR}AlMe2μ-Cl})(NR′)] (R = R′ = 2,6-Pri2–C6H3 (8); R = 2,6-Pri2–C6H3, R′ = But (10)) and [MoMe2(NR}AlCl2μ-Cl})(NR′)] (R = R′ = 2,6-Pri2–C6H3 (9); R = 2,6-Pri2–C6H3, R′ = But (11)), respectively. Exposure of complex 8 to five equivalents of thf or PMe3 affords the adducts [MoMe2(N–2,6-Pri2–C6H3)2(L)] (L = thf (12); L = PMe3 (13)), while reaction with NEt3 (5 equiv.) yields [MoMe2(N–2,6-Pri2–C6H3)2]. The molecular structures of complexes 5, 9 and 11 have been determined.

  结合EtAlCl2（Mo : Al = 1 : 15），酰胺配合物[MoCl2(NR)(NR′)(dme)]（R = R′ = 2,6-Pri2–C6H3（1）；R = 2,6-Pri2–C6H3，R′ = But（3）；R = R′ = But（4）；dme = 1,2-二甲氧基乙烷）和[Mo(NHBut)2(NR)2]（R = 2,6-Pri2–C6H3（5）；R = But（6））各自显示出中等的重氮乙烯催化二聚反应的TON、活性和选择性，这受到酰胺取代基性质的影响。相比之下，[MoCl2(NPh)2(dme)]（2）的产率较低，更倾向于聚合而非二聚。结合MeAlCl2（Mo : Al = 1 : 15）的1–4配合物引发的催化反应显示出明显较低的产率。5配合物与EtAlCl2（2 equiv.）反应生成产物混合物，而加入MeAlCl2则得到[MoMe2(N–2,6-Pri2–C6H3)2]。6配合物与RAlCl2（2 equiv.）（R = Me, Et）反应在两种情况下均生成[Mo(μ-N–But}AlCl2)2]（7）。酰胺衍生物1和3与Me3Al和MeAlCl2反应形成双金属配合物[MoMe2(NR}AlMe2μ-Cl})(NR′)]（R = R′ = 2,6-Pri2–C6H3（8）；R = 2,6-Pri2–C6H3，R′ = But（10））和[MoMe2(NR}AlCl2μ-Cl})(NR′)]（R = R′ = 2,6-Pri2–C6H3（9）；R = 2,6-Pri2–C6H3，R′ = But（11））。将8配合物暴露于五个当量的thf或PMe3，得到加合物[MoMe2(N–2,6-Pri2–C6H3)2(L)]（L = thf（12）；L = PMe3（13）），而与NEt3（5 equiv.）反应则得到[MoMe2(N–2,6-Pri2–C6H3)2]。5、9和11配合物的分子结构已被确定。