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156159

Sigma-Aldrich

Sodium cyanoborohydride

reagent grade, 95%

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Synonym(s):
Sodium cyanotrihydridoborate
Linear Formula:
NaBH3CN
CAS Number:
Molecular Weight:
62.84
Beilstein:
4152656
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

grade

reagent grade

Quality Level

Assay

95%

form

powder

reaction suitability

reagent type: reductant

mp

>242 °C (dec.) (lit.)

SMILES string

[Na+].[BH3-]C#N

InChI

1S/CH3BN.Na/c2-1-3;/h2H3;/q-1;+1

InChI key

CVDUGUOQTVTBJH-UHFFFAOYSA-N

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General description

Sodium cyanoborohydride, also known as sodium cyanotrihydridoborate, is a mild reducing agent that is stable in acidic conditions. It is widely used in the selective reduction of aryl aldehydes and ketones.

Application

Reagent for selective reductions.
Sodium cyanoborohydride is used as a reagent: 
  • To convert the amino-functional Si3N4 surface to a reactive surface with aldehyde groups.
  • For coupling amino-modified oligonucleotide probes.
  • In the synthesis of a novel phenolate-bridged dilanthanum(III) complex of interest as a model for metalloproteins.
  • In the reductive amination of aldehydes and ketones, and in the reductive alkylation of amines.

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Danger

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Flam. Sol. 1 - Skin Corr. 1B - Water-react 1

Supplementary Hazards

Storage Class Code

4.3 - Hazardous materials, which set free flammable gases upon contact with water

WGK

WGK 3

Flash Point(F)

158.0 °F

Flash Point(C)

70 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. Does Product 156159, Sodium Cyanoborohydride, typically have an odor?

    Sodium cyanoborohydride may have an unusual odor due to production steps. It is our belief that this odor is the result of trace amounts of volatile organosulfur compounds which are present as a result of a new manufacturing process.  While this odor may be unpleasant, we are confident the impurity is present at such a low level that it will not affect the performance of this reagent for most applications. If the odor persists in the waste streams following use of this reagent, it can be removed by treating these mixtures with aqueous bleach. In regards to the hazards of the volatile organosulfur compounds, these compounds have a very strong odor which would cause you to remove yourself from the compound's presence much sooner than you would begin to suffer affects from toxicity of these compounds; however, this is research grade material and you should be handling it properly (according to MSDS). The sodium cyanoborohydride itself is a bigger safety concern than the small amounts of organosulfur impurities present in this product.

  4. What impurities are present in Product 156159, Sodium Cyanoborohydride?

    One of the by-products of the synthesis reaction is Dimethyl Sulfide.  It is also possible that there could be some Borate salts present. 

  5. Why is it recommended to store and handle Product 156159, Sodium Cyanoborohydride, under an inert atmosphere?

    Sodium Cyanoborohydride is a very hygroscopic material and contact with water or moist air should be avoided.  Allowing the material to come into contact with water or moist air may decompose the material and could lead to a violent reaction or explosion due to the release of Hydrogen gas. 

  6. What is Product 156159, Sodium Cyanoborohydride, soluble in?

    According to the chemicals encyclopedia published by the Royal Society of Chemistry, 13th Edition, Sodium Cyanoborohydride is soluble in water (212g / 100g solvent), Tetrhydrofuran (37.2g / 100g solvent), and Diglyme (17.6g / 100g solvent).  It is also very soluble in Methanol, slightly soluble in Ethanol and Isopropylamine, and insoluble in Ethyl Ether, Benzene, and Hexane. 

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  8. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

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Tetrahedron Letters, 35, 2775-2775 (1994)
Immobilization of oligonucleotide probes on Si3N4 surface and its application to genetic field effect transistor
Toshiya S, et al.
Materials Science and Engineering, C, 24, 827-832 (2004)
Synthetic Communications, 24, 701-701 (1994)
Aldrichimica Acta, 8, 3-10 (1975)
The Journal of Organic Chemistry, 55, 2552-2552 (1990)

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