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Vitride

HCID 89806
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Basic information

CAS
22722-98-1
Standard SMILES
COCC[O-].COCC[O-].[AlH2+].[Na+]
InChIKey
XJIQVZMZXHEYOY-UHFFFAOYSA-N
Molecular formula
C6H16AlO4.Na
Average molar mass
202.16 g/mol
Monoisotopic mass
202.0761667

Overview

Sodium bis(2-methoxyethoxy)aluminumhydride, also called Red-Al, is an organoaluminium compound. It is used as a reagent 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, L777)

Names & identifiers

Preferred name
Vitride
IUPAC
sodium;alumanylium;bis(2-methoxyethanolate)
English name
Sodium bis(2-methoxyethoxy)aluminiumhydride
Molecular formula
C6H16AlNaO4
Molecular weight
202.16

Names & synonyms

Aluminate(1-), dihydrobis(2-(methoxy-kappaO)ethanolato-kappaO)-, sodiumSMEAHRefChem:887319245-178-204JL3B71VP22722-98-1Sodium bis(2-methoxyethoxy)aluminum hydrideVitridesodium;alumanylium;2-methoxyethanolateAluminate(1-), dihydrobis(2-(methoxy-kappaO)ethanolato-kappaO)-, sodium (1:1)Sodium bis(2-methoxyethoxy)aluminium hydride 70% in tolueneRED-AL
Show more names
Red aluminumSODIUM BIS(2-METHOXYETHOXY)ALUMINIUM HYDRIDESBAHbis(2-Methoxyethoxy)aluMinuM(III) sodiuM hydrideSODIUM BIS(2-METHOXYETHOXY)ALUMINUM DIHYDRIDESynhydrid

Database identifiers

CAS
22722-98-1
PubChem CID
89806

Properties

Computed structural properties

Topological polar surface area
64.6 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
4
Rotatable bonds
4
Heavy atoms
12
Formal charge
0
Complexity
14.4

Experimental & physicochemical properties

Chemical ClassesMetals -> Organic Compounds, Metal Salts
Physical Description · 2 items

Liquid

Viscous liquid; [Merck Index]

Physicochemical properties

Boiling point
396 · 396-402°C
Density
1.036 g/mL · 1.036 g/mL at 25 °C
vapor pressure
21 mm · 21 mm Hg ( 20 °C)
Flash point
40 °F · 40 °F
storage temp.
Flammables area
solubility
Miscible with aromatic hydrocarbons, ether, tetrahydrofuran, dimethyl ether and dimethylformamide. Immiscible with aliphatic hydrocarbons.
form
Viscous Liquid
color
Clear to slightly hazy, colorless to light amber
Specific Gravity
1.036 · 1.036
explosive limit
7 % · 7%
Water Solubility
reacts

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 17.3% (37 of 214) of reports.

Danger

H228 (26.6%): Flammable solid [Danger Flammable solids]

P210, P223, P231+P232, P240, P241, P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P301+P330+P331, P302+P335+P334, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P321, P330, P362+P364, P363, P370+P378, P402+P404, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 214 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Not Classified

Hazard information

Regulatory Information · 3 items

Chemical: Aluminate(1-), dihydrobis(2-methoxyethanolato-O,O')-, sodium

Aluminate(1-), dihydrobis[2-(methoxy-.kappa.O)ethanolato-.kappa.O]-, sodium (1:1) is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Aluminate(1-), dihydrobis[2-(methoxy-.kappa.O)ethanolato-.kappa.O]-, sodium (1:1) 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)

REACH registered substance: Sodium dihydridobis(2-methoxyethanolato)aluminate(1-) (EC: 245-178-2)

Other Safety InformationIMAP assessments - Aluminate(1-), dihydrobis(2-methoxyethanolato-O,O')-, sodium: Environment tier I assessment
Hazards Summary · 1 item

70% Toluene solution: Pyrophoric; Reacts violently with water evolving flammable gases; Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; Harmful by inhalation; [Alfa Aesar MSDS] See Aluminum hydride.

Chemistry & industry

Pharmacology

Metabolism/Metabolites · 1 item

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)

Uses & manufacturing

Uses · 2 items

Used as a reducing agent; [Merck Index]

Sodium bis(2-methoxyethoxy)aluminumhydride is used as a reagent in organic synthesis. (L777)

U.S. Production2023: 500,000 - <1,000,000 lb
Industry UsesReducing agent
General Manufacturing Information · 2 items

All Other Basic Organic Chemical Manufacturing

Aluminate(1-), dihydrobis[2-(methoxy-.kappa.O)ethanolato-.kappa.O]-, sodium (1:1): ACTIVE

Applications · 4 items

UsesReducing agent.

UsesRed-Al sodium bis(2-methoxyethoxy)aluminum hydride can be used as: A tosyl deprotecting agent.A catalyst for crosslinking of polyvinylsilanes (PVS) by Si-Si dehydrocoupling reaction in the presence of group 4 metallocene complexes.A reducing reagent for the synthesis of optically active N-protected amino alcohols and peptide alcohols.

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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UNII
04JL3B71VP
EC Number
245-178-2
Hydrolytic Sensitivity
8 · 8: reacts rapidly with moisture, water, protic solvents
Sensitive
Air & Moisture Sensitive
Merck
14 · 14,8564
InChI
1S/2C3H7O2.Al.Na.2H/c2*1-5-3-2-4;;;;/h2*2-3H2,1H3;;;;/q2*-1;2*+1;;
InChIKey
OKUDBXZACZBZJE-UHFFFAOYSA-N
SMILES
[Na+].[H][Al-]([H])(OCCOC)OCCOC
LogP
-2.64 at · -2.64 at 25℃ and pH7
CAS DataBase Reference
22722 · 22722-98-1(CAS DataBase Reference)
FDA UNII
4 JL3B71VP · 04JL3B71VP
EPA Substance Registry System
Aluminate(1-), dihydrobis[2-(methoxy-.kappa.O)ethanolato-.kappa.O]-, sodium (22722-98-1)
UNSPSC Code
12352000 · 12352000
NACRES
22 · NA.22
Symbol(GHS)
2 · GHS02,GHS05,GHS07,GHS08
Signal word
Danger
Hazard statements
225 · H225-H260-H304-H314-H336-H361d-H373-H412
Precautionary statements
210 · P210-P231+P232-P280-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338
target organs
Central nervous system
Hazard Codes
F,C
Risk Statements
11 · 11-14/15-34-48/20-63-65-67
Safety Statements
26 · 26-36/37/39-43-45-62-46-16-9
RIDADR
3399 · UN 3399 4.3/PG 1
WGK Germany
2 · 2
F
1 · 1-10
TSCA
TSCA listed
HazardClass
4.3 · 4.3
PackingGroup
I
HS Code
29319090 · 29319090
Storage Class
4.3 · 4.3 - Hazardous materials which set free flammable gases upon contact with water
Hazard Classifications
3 Asp · Aquatic Chronic 3Asp. Tox. 1Eye Dam. 1Flam. Liq. 2Repr. 2Skin Corr. 1BSTOT RE 2 InhalationSTOT SE 3Water-react 1
REACH Registrations
Active
Excepted Quantities
Not Permitted as Excepted Quantity
Hazard Classes and Categories
Flam. Sol. 1 (26.6%)

Safety & protection

Minimum Risk LevelIntermediate Oral: 1.0 mg/kg/day (L134) Chronic Oral: 1.0 mg/kg/day (L134)

Toxicology

Health Effects · 1 item

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)

Adverse EffectsDermatotoxin - Skin burns.
Exposure RoutesOral (L739) ; inhalation (L739)
Toxicity Summary · 1 item

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 · 1 item

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)

Carcinogen Classification · 1 item

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).

Safety data

F
1-10
wgk
2
tsca
TSCA listed
ridadr
UN 3399 4.3/PG 1
hs_code
29319090
risk_code
11-14/15-34-48/20-63-65-67
Signal word
Danger
Symbol(GHS)
GHS02,GHS05,GHS07,GHS08
hazard_code
F,C
safety_code
26-36/37/39-43-45-62-46-16-9
hazard_class
4.3
Storage Class
4.3 - Hazardous materials which set free flammable gases upon contact with water
packing_group
I
target organs
Central nervous system
Hazard statements
H225-H260-H304-H314-H336-H361d-H373-H412
Excepted Quantities
Not Permitted as Excepted Quantity
REACH Registrations
Active
Hazard Classifications
Aquatic Chronic 3Asp. Tox. 1Eye Dam. 1Flam. Liq. 2Repr. 2Skin Corr. 1BSTOT RE 2 InhalationSTOT SE 3Water-react 1
Precautionary statements
P210-P231+P232-P280-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338

UsesSodium bis(2-methoxyethoxy)aluminum hydride acts as a reducing agent in organic synthesis. It is used to prepare azoxyarenes, azoarenes and hydroazoarenes from nitroarenes. It plays an important role for the conversion of aldehydes, ketones, carboxylic acids, esters, acyl halides and anhydrides to primary alcohols. It is also employed in hydroaluminate alkenes and alkynes. It is utilized in the reduction of lactones and epoxides into diols. Further, it serves as a methylation reagent for aryl-activated compounds. In addition to this, it is involved in the reduction of amides, nitriles and amines to the corresponding amines.

General DescriptionRed-Al sodium bis(2-methoxyethoxy)aluminum hydride [NaAlH2(OCH2CH2OCH3)2] is used as a versatile reducing agent in organic synthesis. It is used to reduce:Aldehydes, ketones, esters, and anhydrides to primary alcohols.Ketoximes and aldoximes to primary amines.Cyclic compounds such as lactones and epoxides to diols.It is also used as a catalyst in the ring-opening polymerization reactions.

Preparation methods · 1 item

PreparationOne method of preparation is the controlled alcoholysis of NaAlH4 with 2- methoxyethanol:NaAlH4+2 CH3OCH2CH2OH→NaAlH2(OCH2CH2OCH3)2 +H2On an industrial scale, however, it is produced by direct synthesis from sodium, aluminum, and 2-methoxyethanol at 140 – 155 C in an atmosphere of hydrogen at at least 7 MPa:Na+Al+2 CH3OCH2CH2OH→NaAlH2(OCH2CH2OCH3)2The quantity of hydrogen required is generated in situ by the reaction of sodium and aluminum with the alcohol. SDMA(Sodium bis(2-methoxyethoxy)aluminiumhydride) is marketed as a 70 % solution in toluene (r = 1.036 g/cm3 ) under the name Vitride (Hexcel).

Upstream & downstream products

Downstream products

Morpholine-3,4-dicarboxylic acid 4-tert-butyl esterAllura red acMethyl 7-[(3RS)-3-hydroxy-5-oxocyclopent-1-enyl]heptanoateAnthracene, 9-ethyl-9,10-dihydro-9,10-dimethyl-