Grundinformationen
- Standard-SMILES
CC(C)[CH2][AlH][CH2]C(C)C- InChIKey
AZWXAPCAJCYGIA-UHFFFAOYSA-N- Summenformel
- C8H19Al
- Durchschnittliche Molmasse
- 142,22 g/mol
- Monoisotopische Masse
- 142,13021424
Überblick
Diisobutylaluminium hydride is an organoaluminum compound. It is a reducing agent used in organic synthesis. Aluminum is the most abundant metal in the earth's crust and is always found combined with other elements such as oxygen, silicon, and fluorine. (L739, L740, L774)
Namen und Bezeichner
- Bevorzugter Name
- Diisobutylaluminum hydride
- IUPAC
- bis(2-methylpropyl)alumane
- Lokaler Name
- Diisobutylaluminiumhydrid
- Englischer Name
- Diisobutylaluminium hydride
- Summenformel
- C8H19Al
- Molmasse
- 142.22
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
1191-15-7- PubChem CID
- 14487
- DTXSID
DTXSID4041866- UNII
- H2EJ47H11A
- EC Number
- 214-729-9
Eigenschaften
Berechnete Struktureigenschaften
- Polarare Oberfläche (TPSA)
- 0 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 0
- Frei drehbare Bindungen
- 4
- Schwere Atome
- 9
- Formalladung
- 0
- Komplexität
- 49,6
Experimentelle und physikochemische Eigenschaften
Chemical Classes
Metals -> Metals, Organic Compounds
Flammable agents - 4th degree
Density
0.798 g/mL
0.798 @25 °C
Melting Point
-80 °C (Freezing point)
-80 °C
Physical Description
CBI
Colorless liquid; [Hawley]
Stability/Shelf Life
Low melting solids or colorless, volatile liquids. /Alkylaluminum halides/
Less sensitive than trialkylaminums to oxidation upon exposure to air. /Alkylaluminum halides/
Other Experimental Properties
Pyrophoric; dilute solutions nonpyrophoric
Specific heat: 2.15 J/g at 57 °C
The fumes are white, possess a characteristic musty odor at low concentrations, and thus have suitable warning properties. /Aluminum alkyls/
Dialkylaluminum hydrides are trimeric, with bridging hydrides.
Physikochemische Eigenschaften
- Schmelzpunkt
- -70 °C · -70 °C
- Siedepunkt
- 65 °C · 65 °C
- Dichte
- 1.23 g/mL · 1.23 g/mL at 25 °C
- Dampfdruck
- 13.3 Pa · 13.3Pa at 90℃
- Flammpunkt
- 40 °F · 40 °F
- storage temp.
- 2 · 2-8°C
- Löslichkeit
- Miscible with organic solvents.
- Aggregatzustand
- Solution
- Wichte
- 0.86 · 0.860
- Farbe
- Clear
- Wasserlöslichkeit
- vigorous reaction
- BRN
- 4123663 · 4123663
- InChI
- 1S/2C4H9.Al.H/c2*1-4(2)3;;/h2*4H,1H2,2-3H3;;
- InChIKey
- AZWXAPCAJCYGIA-UHFFFAOYSA-N
- SMILES
- CC(C)C[AlH]CC(C)C
- LogP
- 4.22 · 4.22
- CAS Datenbank
- 1191 · 1191-15-7(CAS DataBase Reference)
- NIST chemische Informationen
- Diisobutylaluminum hydride(1191-15-7)
- EPA chemische Informationen
- Diisobutylaluminum hydride (1191-15-7)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Danger
H250 (97.7%): Catches fire spontaneously if exposed to air [Danger Pyrophoric liquids]
P210, P222, P223, P231, P231+P232, P233, P260, P264, P264+P265, P280, P301+P330+P331, P302+P335+P334, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P363, P370+P378, P402+P404, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 173 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Regulatory Information
Chemical: Aluminium, hydrobis(2-methylpropyl)-
Aluminum, hydrobis(2-methylpropyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Aluminum, hydrobis(2-methylpropyl)- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
Status: Active Update: 20-12-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/13341
Aluminium, hydrobis(2-methylpropyl)-: HSNO Approval: HSR001272 Approved with controls
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
Fire Potential
The undiluted material ignites in air unless diluted to below 25% concentration.
Ignites spontaneously in air.
Certain polymerization catalysts, such as aluminum alkyls, react & burn violently on contact with water. /Aluminum alkyls/
Aluminum alkyls are organic aluminum compounds that are highly reactive and dangerous because of spontaneous burning in air. /Aluminum alkyls/
Prophoric material in flammable solvent. Vapors are heavier than air & may travel to a source of ignition & flash back. /Aluminum alkyls/
Hazards Summary
Spontaneously ignites in air; [Hawley] Stored 25% w/w in hexane; Pyrophoric; Reacts violently with water, evolving extremely flammable gases; A corrosive substance that can cause injury to the skin, eyes, and respiratory tract; Inhalation may cause chemical pneumonitis and pulmonary edema; May have CNS effects; [MSDSonline] Organoaluminum compounds are corrosive; Harmful if absorbed through the skin or inhaled; The butyl alkyls and below are pyrophoric; Aluminum alkyls are eye irritants; [HSDB] Organic aluminum compounds can cause irritation or burns, depending upon concentration; [Ullmann] TLV withdrawn for aluminum alkyls because of inadequate toxicological data; [ACGIH] See Aluminum. See ORGANOMETALS.
DOT Emergency Guidelines
/GUIDE 138: SUBSTANCES - WATER-REACTIVE (EMITTING FLAMMABLE GASES)/ Fire or Explosion: Produce flammable gases on contact with water. May ignite on contact with water or moist air. Some react vigorously or explosively on contact with water. May be ignited by heat, sparks or flames. May re-ignite after fire is extinguished. Some are transported in highly flammable liquids. Runoff may create fire or explosion hazard. /Aluminum alkyl hydrides/
/GUIDE 138: SUBSTANCES - WATER-REACTIVE (EMITTING FLAMMABLE GASES)/ Health: Inhalation or contact with vapors, substance, or decomposition products may cause severe injury or death. May produce corrosive solutions on contact with water. Fire will produce irritating, corrosive and/or toxic gases. Runoff from fire control may cause pollution. /Aluminum alkyl hydrides/
/GUIDE 138: SUBSTANCES - WATER-REACTIVE (EMITTING FLAMMABLE GASES)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meter (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate the area before entry. /Aluminum alkyl hydrides/
/GUIDE 138: SUBSTANCES - WATER-REACTIVE (EMITTING FLAMMABLE GASES)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing will only provide limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Aluminum alkyl hydrides/
For more DOT Emergency Guidelines (Complete) data for DIISOBUTYLALUMINUM HYDRIDE (8 total), please visit the HSDB record page.
NFPA Hazard Classification
3 - Materials that, under emergency conditions, can cause serious or permanent injury.
4 - Materials that rapidly or completely vaporize at atmospheric pressure and normal ambient temperature or that are readily dispersed in air and burn readily.
3 - Materials that in themselves are capable of detonation or explosive decomposition or explosive reaction but that require a strong initiating source or must be heated under confinement before initiation.
NIOSH Recommendations
Recommended Exposure Limit: 10-Hr Time-Weighted Avg: 10 mg/cu m (total). /Aluminum/
Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 5 mg/cu m (resp). /Aluminum/
Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 2 mg/cu m. /Aluminum (soluble salts and alkyls, as Al)/
Recommended Exposure Limit: 10 Hr Time-Weighted Avg: 5 mg/cu m. /Aluminum (pyro powders and welding fumes, as Al)/
Hazard Classes and Categories
Pyr. Liq. 1 (97.7%)
Flammable agents - 4th degree, Reactive agents - 3rd degree
State Drinking Water Guidelines
(AZ) ARIZONA 73 ug/l /Aluminum/
(CA) CALIFORNIA 200 ug/l /Aluminum/
(ME) MAINE 1430 ug/l /Aluminum/
Shipment Methods and Regulations
The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.
No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./
Sicherheit und Schutzausrüstung
Exposure Control and Personal Protection
TIH (Toxic Inhalation Hazard) - Term used to describe gases and volatile liquids that are toxic when inhaled. Some are TIH materials themselves, e.g., chlorine, and some release TIH gases when spilled in water, e.g., chlorosilanes. [ERG 2016].
Fire Fighting Procedures
Do not use water, foam or halogenated extinguishing agents.
Stop flow of liquid before extinguishing fire. Use dry chemical or carbon dioxide. DO NOT use water as straight stream directly on spilled material. Water fog can be used to control fire. DO NOT use halogenated extinguishing agents on spilled material. Violent reaction may result. Use water spray to keep fire-exposed containers cool. Fight fire from protected location or maximum possible distance. /Aluminum Alkyls/
Storage Conditions
Extremely reactive with air, moisture and compounds containing active hydrogen and therefore must be kept under a blanket of inert gas. /Aluminum alkyls/
In general, materials ... toxic as stored or which can decompose into toxic components ... Should be stored in cool ... ventilated place, out of ... sun, away from ... fire hazard ... be periodically inspected and monitored. Incompatible materials should be isolated ...
All possibility of contact with water must be avoided. Solution containing not more than 20% of these compounds in non-reactive solvents, however, can be handled without risk of spontaneous ignition. /Aluminum alkyls/
Must be stored in an inert atmosphere; sensitive to oxidation and hydrolysis in air. /Trialkylaluminums/
Separate from air, water, halocarbons, alcohols. Store in a cool, dry, well-ventilated location. Outside or detached storage is preferred. Inside storage should be in a standard flammable liquid storage warehouse, room, or cabinet. /Aluminum alkyls/
Disposal Methods
Aluminum compounds are treated under anhydrous conditions to prevent violent reactions, recover solvent, and form Al compounds suitable for landfill by reaction with anhydrous hydrolysis agent, eg calcium hydroxide. /Aluminum compounds/
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Preventive Measures
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Work clothing that becomes wet or significantly contaminated should be removed and replaced. /Aluminum (soluble salts and alkyls, as Al)/
Workers whose clothing may have become contaminated should change into uncontaminated clothing before leaving the work premises. /Aluminum (soluble salts and alkyls, as Al)/
The worker should immediately wash the skin when it becomes contaminated. /Aluminum (soluble salts and alkyls, as Al)/
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
Threshold Limit Values (TLV)
8 hr Time Weighted Avg (TWA): 1 mg/cu m (respirable fraction). /Aluminum metal and insoluble compounds/
Excursion Limit Recommendation: Excursions in worker exposure levels may exceed 3 times the TLV-TWA for no more than a total of 30 minutes during a work day, and under no circumstances should they exceed 5 times the TLV-TWA, provided that the TLV-TWA is not exceeded. /Aluminum and compounds, as Al; metal dust, pyro powders, soluble salts & alkyls (not otherwise specified)/
A4; Not classifiable as a human carcinogen. /Aluminum metal and insoluble compounds/
Protective Action Criteria (PAC)
29 [mg/m3]
320 [mg/m3]
1900 [mg/m3]
Personal Protective Equipment (PPE)
Wear appropriate personal protective clothing to prevent skin contact. /Aluminum (soluble salts and alkyls, as Al/
Wear appropriate eye protection to prevent eye contact. /Aluminum (soluble salts and alkyls, as Al)/
Protective clothing and a high standard of training in the necessary precautionary measures are essential for the handling of the materials. /Aluminum alkyls/
Toxikologische Informationen
Health Effects
Aluminum targets the nervous system and causes decreased nervous system performance and is associated with altered function of the blood-brain barrier. The accumulation of aluminum in the body may cause bone or brain diseases. High levels of aluminum have been linked to Alzheimer's disease. A small percentage of people are allergic to aluminium and experience contact dermatitis, digestive disorders, vomiting or other symptoms upon contact or ingestion of products containing aluminium. (L739, L740)
Toxicity Summary
The main target organs of aluminum are the central nervous system and bone. Aluminum binds with dietary phosphorus and impairs gastrointestinal absorption of phosphorus. The decreased phosphate body burden results in osteomalacia (softening of the bones due to defective bone mineralization) and rickets. Aluminum's neurotoxicity is believed to involve several mechanisms. Changes in cytoskeletal protein functions as a results of altered phosphorylation, proteolysis, transport, and synthesis are believed to be one cause. Aluminum may induce neurobehavioral effects by affecting permeability of the blood-brain barrier, cholinergic activity, signal transduction pathways, lipid peroxidation, and impair neuronal glutamate nitric oxide-cyclic GMP pathway, as well as interfere with metabolism of essential trace elements because of similar coordination chemistries and consequent competitive interactions. It has been suggested that aluminum's interaction with estrogen receptors increases the expression of estrogen-related genes and thereby contributes to the progression of breast cancer (A235), but studies have not been able to establish a clear link between aluminum and increased risk of breast cancer (A15468). Certain aluminum salts induce immune responses by activating inflammasomes. (L739, A235, A236)
Signs and Symptoms
Inhalating aluminum dust causes coughing and abnormal chest X-rays. A small percentage of people are allergic to aluminium and experience contact dermatitis, digestive disorders, vomiting or other symptoms upon contact or ingestion of products containing aluminium. (L739, L740)
Human Toxicity Excerpts
/SIGNS AND SYMPTOMS/ Corrosive. Causes severe eye and skin burns. Irritating to skin, eyes, and respiratory system. May be harmful if absorbed through skin or inhaled. "Metal fume fever" may result from inhalation of fumes /from organoaluminum compounds/. /SRP: While possible, metal fume fever is not highly probable./ /Organoaluminum compounds/
/OTHER TOXICITY INFORMATION/ Vapors of the pyrophoric alkyls (butyls and below) are nontoxic because they are completely consumed, but inhalation of the metallic oxide smoke (Al2O3) at 15 mg/cu m or greater can result in symptoms such as "metal fume fever." /Aluminum alkyls/
Carcinogen Classification
Not listed by IARC. IARC classified aluminum production as carcinogenic to humans (Group 1), but did not implicate aluminum itself as a human carcinogen. (L135) A link between use of aluminum-containing antiperspirants and increased risk of breast cancer has been proposed (A235), but studies have not been able to establish a clear link (A15468).
Regulatorische Informationen
State Drinking Water Guidelines
(AZ) ARIZONA 73 ug/l /Aluminum/
(CA) CALIFORNIA 200 ug/l /Aluminum/
(ME) MAINE 1430 ug/l /Aluminum/
Sicherheitsdaten
- F
- 1-4.3-10
- wgk
- 2
- tsca
- TSCA listed
- ridadr
- UN 3399 4.3/PG 1
- hs_code
- 29319090
- RTECS-Nr.
- BD0710000
- risk_code
- 14/15-17-35-40-67-65-63-48/20-11-34-19-62-51/53-23/24/25-20/21/22-15-14-50/53-37-22
- hazard_code
- F,T,C,N
- safety_code
- 26-43-45-62-46-36/37/39-29-16-61-27-9
- hazard_class
- 4.3
- packing_group
- I
- Speicherklasse
- 4.2 - Pyrophoric and self-heating hazardous materials
- Giftige Stoffe Daten
- 1191-15-7(Hazardous Substances Data)
- Hazard Classifications
- Aquatic Acute 1Aquatic Chronic 1Asp. Tox. 1Eye Dam. 1Pyr. Liq. 1Skin Corr. 1BSTOT SE 3Water-react 1
Chemie und Industrie
Pharmakologische Informationen
Metabolism/Metabolites
Aluminum is poorly absorbed following either oral or inhalation exposure and is essentially not absorbed dermally. The bioavailability of aluminum is strongly influenced by the aluminum compound and the presence of dietary constituents which can complex with aluminum and enhance or inhibit its absorption. Aluminum binds to various ligands in the blood and distributes to every organ, with highest concentrations found in bone and lung tissues. In living organisms, aluminum is believed to exist in four different forms: as free ions, as low-molecular-weight complexes, as physically bound macromolecular complexes, and as covalently bound macromolecular complexes. Absorbed aluminum is excreted principally in the urine and, to a lesser extent, in the bile, while unabsorbed aluminum is excreted in the faeces. (L739)
Verwendung und Herstellung
Uses
Used as a reducing agent (pharmaceuticals, aldehydes, amides, and olefins), a polymerization catalyst for polyethylene, and an intermediate in silicones, certain polymers, and organic acid synthesis; [HSDB] Organic aluminum compounds are some of the most important, highest volume, highest value organometallic compounds in production. [Ullmann]
... Reduction of the aldehyde or ketone carbonyl function to an alcohol.
Reducing agent in pharmaceuticals
REDUCING AGENT, EG, FOR ALDEHYDES, AMIDES & OLEFINS
POLYMERIZATION CATALYST FOR POLYETHYLENE
...Intermediates in silicones, certain polymers and organic acid synthesis.
U.S. Production
2023: 1,000,000 - <2,500,000 lb
(1979) PROBABLY GREATER THAN 4.54X10+6 GRAMS
Methods of Manufacturing
Reaction of isobutylene and hydrogen with aluminum.
CONTROLLED THERMAL DECOMPOSITION OF TRIISOBUTYLALUMINUM TO DIISOBUTYLALUMINUM HYDRIDE & ISOBUTENE; DIRECT REACTION OF ALUMINUM, HYDROGEN, & TRIISOBUTYLALUMINUM
General Manufacturing Information
Not Known or Reasonably Ascertainable
Aluminum, hydrobis(2-methylpropyl)-: ACTIVE
Anwendungen
BeschreibungDiisobutylaluminium hydride (DIBALH, DIBAL, DIBAL-H or DIBAH) is a reducing agent with the formula (i-Bu2AlH)2, where i-Bu represents isobutyl (-CH2CH(CH3)2). It can be used for various homogeneous reductions such as alkynes to alkenes, esters or nitriles to aldehydes. It is available commercially as the neat reagent and as a solution in several different solvents (hexane, dichloromethane, tetrahydrofuran, etc.). The neat reagent is a liquid and is supplied in metal cylinders. It is pyrophoric and highly reactive and therefore must be handled with great care. The molar solutions in organic solvents are more stable and easier to handle provided that the normal precautions are taken for working with air-sensitive compounds. They must all be handled in an atmosphere free from oxygen and water. Commonly used solvents for diisobutylaluminium hydride are dichloromethane, diglyme, dioxane and tetrahydrofuran. Even when the substrate is not completely soluble in these solvents successful reductions can be accomplished.
VerwendenDiisobutylaluminum hydride is commonly used as a reducing agent in organic synthesis.Diisobutylaluminum hydride can be used in the following protocols:As a promotor of Tishchenko reaction of aldehydes.Conversion of benzylidene acetals of 1,2-and 1,3-glycols to the corresponding monobenzyl ethers of the glycols.To generate a novel chiral reducing agent based on (S)-proline for the asymmetric reduction of prochiral ketones.
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