CAS 16940-66-2|SODIUM BOROHYDRIDE|sodium boranuide|potassium borohydride|Sodium Tetrahydroborate|Sodium boranuide|sodium boranuide|Sodium tetrahydridoborate|Sodium borohydride|四氢硼酸钠|硼氢化钠|Ve...

General Information

Structure

Molecular Formula

BNa

Molecular Mass

33.80077

Exact Mass

33.99907468

Charge

InChI

InChI=1S/BH4.Na/h1H4;/q-1;+1

InChIKey

YOQDYZUWIQVZSF-UHFFFAOYSA-N

Canonic Smiles

[BH3-].[Na+]

Isomeric Smiles

[BH3-].[Na+]

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

-1.804

LogD (pH = 7.4)

-1.804

Log P

-1.804

Molar Refractivity

3.2

Polarizability

3.2773068

Polar Surface Area

0.0

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

Synonyms

SODIUM BOROHYDRIDESodium TetrahydroborateSodium tetrahydridoborateSodium borohydride四氢硼酸钠硼氢化钠VenPure® AF硼氢化钠溶液Sodium borohydrideCobalt-doped sodium borohydride钴掺杂的硼氢化钠氧化铝负载硼氢化钠Sodium borohydride solutionVenPure® SF硼氢化钠VenPure®Sodium borohydride on aluminum oxideSodium borohydride, stable aq. soln., 4.4M in 14M NaOH硼氢化钠, 稳定水溶液, 4.4M的氢氧化钠溶液(14M)

IUPAC name

sodium boranuide

IUPAC Traditional name

potassium borohydride sodium boranuide

IUPAC Systematic name

Sodium boranuide

Names and Identifiers

Registration numbers

CAS Number

EC Number

Wikipedia Title

PubChem CID

Chemspider ID

MeSH Name

Gmelin ID

CHEBI ID

PubChem SID

24879549162089989248529012486868224882317248546252485278524886164248861652486873624854882248717242486868324886166

MDL Number

MFCD00003518

Merck Index

148592

Registration numbers

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

MP Biomedicals

02102894

Hygroscopic
Purity: 98-99%
Crystalline
Excellent reducing agent.

Wikipedia

Sodium_borohydride

Sigma Aldrich

452165

Features and Benefits
Formulated for color and odor removal
Packaging
100 g in poly bottle
2 kg in steel drum
Legal Information
Rohm & Haas product
VenPure is a registered trademark of Rohm and Haas Chemicals LLC

686018

Analysis Note
Hydrogen content, XRD plots and metal purity data are available upon request.
General description
Atomic number of base material: 11
Packaging
10 g in poly bottle
Protocols & Applications
Metal Borohydrides as Hydrogen Storage Materials
Boron-based Hydrogen Storage

632287

Packaging
100, 500 g in poly bottle
2 kg in steel drum
Legal Information
Rohm & Haas product
VenPure is a registered trademark of Rohm and Haas Chemicals LLC

556351

Packaging
25 mL in glass bottle

247677

Features and Benefits
A convenient solid source of hydrogen gas. Each pellet readily liberates ~500mL of hydrogen gas upon contact with water. Useful for producing an anaerobic reducing atmosphere in biological experiments. Cobalt-doped
Packaging
50 g in poly bottle

215511

Packaging
100 mL in Sure/Seal™

200972

Packaging
100 mL in Sure/Seal™

452882

Packaging
2 kg in steel drum
5, 25, 100, 500 g in poly bottle
Legal Information
Rohm & Haas product
VenPure is a registered trademark of Rohm and Haas Chemicals LLC
Application
Nanocrystalline superlattices in gold colloid solution have been prepared by ligand-induction using AuCl3 reduced with sodium borohydride.1 Nucleophilic addition of hydride ion from sodium borohydride is an inexpensive alternative method for the Baylis-Hillman reaction to form [E]-α-methylcinnamic acids.2

452904

Packaging
1 L in poly bottle
25 mL in poly bottle
Legal Information
Rohm & Haas product

452890

Packaging
2 kg in steel drum
25, 100, 500 g in poly bottle
Legal Information
Rohm & Haas product
VenPure is a registered trademark of Rohm and Haas Chemicals LLC

452874

Packaging
100 g in poly bottle
25 g in amber poly
2 kg in steel drum
500 g in amber poly
Legal Information
Product of Rohm & Haas
VenPure is a registered trademark of Rohm and Haas Chemicals LLC
Application
Nanocrystalline superlattices in gold colloid solution have been prepared by ligand-induction using AuCl3 reduced with sodium borohydride.1 Nucleophilic addition of hydride ion from sodium borohydride is an inexpensive alternative method for the Baylis-Hillman reaction to form [E]-α-methylcinnamic acids.2

213462

Packaging
25, 100 g in poly bottle
Application
Nanocrystalline superlattices in gold colloid solution have been prepared by ligand-induction using AuCl3 reduced with sodium borohydride.1 Nucleophilic addition of hydride ion from sodium borohydride is an inexpensive alternative method for the Baylis-Hillman reaction to form [E]-α-methylcinnamic acids.2
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

243620

Application
Supported reagent which is often more selective and easier to use than free NaBH4.
Packaging
10, 50 g in glass bottle

480886

452173

Features and Benefits
Formulated for color and odor removal
Packaging
100, 500 g in poly bottle
Legal Information
Product of Rohm & Haas
VenPure is a registered trademark of Rohm and Haas Chemicals LLC

71320

Other Notes
Reduction of carboxylic acid derivatives 1,2

Molecule Details

References

PubChem Literature

From Data Sources

• The reduction of aldehydes and ketones to alcohols occurs in alcoholic or aqueous media. For highly selective reduction of aldehydes in the presence of ketones, see: Synth. Commun., 18, 1927 (1988). For enantioselective reduction, see L-tert-Leucine, L13707. Borohydride reductions can be carried out in organic solvents, e.g. toluene, under phase-transfer conditions, amenable to scale-up: Org. Process Res. Dev., 1, 287 (1997).

• Monograph: J. Seyden-Penne, Reductions by the Alumino- and Borohydrides In Organic Synthesis, 2nd ed., Wiley, N.Y. (1997).

• Acid chlorides are readily reduced to alcohols; controlled reduction at -78^o to give the aldehyde has been reported; see, e.g.: Synth. Commun., 12, 839 (1982). See also Bis(triphenylphosphine)copper(I) borohydride, A13730. For an indirect method of reduction, see Triethyl phosphite, L00339.

• Reductive alkylation of amines can be effected with NaBH₄/formaldehyde; see e.g.: Synthesis, 743 (1980); or TFA: Synthesis, 709 (1987). See also Sodium cyanoborohydride, 87839. Reductive alkylation of aromatic amines with a variety of aldehydes and ketones has been reported, using NaBH₄/H₂SO₄: Synthesis, 121 (1993).

• The combination of borohydride and iodine (in situ borane) reduces acids to alcohols: J. Org. Chem., 56, 5964 (1991); amino acids to amino alcohols: J. Org. Chem., 58, 3568 (1993); and effects reduction of esters, amides and nitriles, as well as hydroboration of alkenes: Tetrahedron, 45, 4623 (1992). See also Boron trifluoride diethyl etherate, A15275, and Sodium triacetoxyborohydride, B22060.

• Hydroboration of olefins has also been reported under similar conditions: Synlett, 997 (2000).

• A vast number of modified borohydride reagents have been reported, with the objective either of increasing the reducing power or improving selectivity. Many examples involve combinations with metal salts:

• LiCl: reduction of amino acids via Me esters: Tetrahedron Lett., 39, 917 (1998). CaCl₂: selective 1,2-reduction enones: Chem. Lett., 1847 (1991). CeCl₃: increased selectivity for 1,2-reduction of enones: J. Chem. Soc., Chem. Commun., 601 (1978); reduction of ketones in the presence of aldehydes: J. Am. Chem. Soc., 101, 5848 (1979). CuCl: dehalogenation of aryl iodides and bromides: J. Org. Chem., 54, 5308 (1989); reduction of nitro compounds: Chem. Ind. (London), 75 (1984). CuSO₄: reduction of esters, alkenes, nitriles and nitro compounds; amides and acids inert: Synlett, 419 (1990) [but see also Synlett, 79 (1993): Cu(OAc)₂ preferred for reduction of nitro-groups]; reduction of azides: Synth. Commun., 24, 549 (1994). NiCl₂: generation in situ of nickel boride, as an alternative to Raney nickel for desulfurizations: Synth. Commun., 16, 779 (1986); J. Chem. Soc., Chem. Commun., 819 (1990); J. Org. Chem., 57, 1986 (1992); 58, 2407 (1993); phenols and enols have also been deoxygenated: J. Chem. Soc., Perkin 1, 1897 (1992), and aryl nitrile reduced to benzylamines: Synth. Commun, 32, 1265 (2002). For conversion to Zn(BH₄)₂, see Zinc chloride, A16281. InCl₃: radical reducing system - alternative to Bu₃SnH: J. Am. Chem. Soc., 124, 906 (2002)_.

• For a brief feature on uses of the reagent in synthesis, see: Synlett, 182 (2005).

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC name

sodium boranuide

IUPAC Traditional name

potassium borohydride sodium boranuide

IUPAC Systematic name

Sodium boranuide

Molecule Details

MP Biomedicals

02102894

Hygroscopic
Purity: 98-99%
Crystalline
Excellent reducing agent.

Wikipedia

Sodium_borohydride

Sigma Aldrich

452165

686018

632287

Packaging
100, 500 g in poly bottle
2 kg in steel drum
Legal Information
Rohm & Haas product
VenPure is a registered trademark of Rohm and Haas Chemicals LLC

556351

Packaging
25 mL in glass bottle

247677

215511

Packaging
100 mL in Sure/Seal™

200972

Packaging
100 mL in Sure/Seal™

452882

452904

Packaging
1 L in poly bottle
25 mL in poly bottle
Legal Information
Rohm & Haas product

452890

Packaging
2 kg in steel drum
25, 100, 500 g in poly bottle
Legal Information
Rohm & Haas product
VenPure is a registered trademark of Rohm and Haas Chemicals LLC

452874

213462

243620

Application
Supported reagent which is often more selective and easier to use than free NaBH4.
Packaging
10, 50 g in glass bottle

480886

452173

71320

Other Notes
Reduction of carboxylic acid derivatives 1,2

References

PubChem Literature

From Data Sources

• Monograph: J. Seyden-Penne, Reductions by the Alumino- and Borohydrides In Organic Synthesis, 2nd ed., Wiley, N.Y. (1997).