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156159

Sigma-Aldrich

Sodium cyanoborohydride

reagent grade, 95%

Synonym(s):

Sodium cyanotrihydridoborate

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About This Item

Linear Formula:
NaBH3CN
CAS Number:
Molecular Weight:
62.84
Beilstein:
4152656
EC Number:
MDL number:
UNSPSC Code:
12352306
PubChem Substance ID:
NACRES:
NA.22
form:
powder
Assay:
95%
Pricing and availability is not currently available.

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.[1]

Application

Reagent for selective reductions.[2]
Sodium cyanoborohydride is used as a reagent: 
  • To convert the amino-functional Si3N4 surface to a reactive surface with aldehyde groups.[3]
  • For coupling amino-modified oligonucleotide probes. [3]
  • In the synthesis of a novel phenolate-bridged dilanthanum(III) complex of interest as a model for metalloproteins.
  • In the reductive amination of aldehydes[4] and ketones,[5] and in the reductive alkylation of amines.[6]

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Signal Word

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 - closed cup

Flash Point(C)

70 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

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Tetrahedron Letters, 35, 2775-2775 (1994)
Synthetic Communications, 24, 701-701 (1994)
Aldrichimica Acta, 8, 3-10 (1975)
The Journal of Organic Chemistry, 55, 2552-2552 (1990)
Reductive deoxygenation of aryl aldehydes and ketones and benzylic, allylic, and tertiary alcohols by zinc iodide-sodium cyanoborohydride
CK L, et al.
The Journal of Organic Chemistry, 51, 3038-3043 (1986)

Articles

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Glycans play a key role in protein structure and disease; representation on cell surfaces is the glycome.

Glycans play a key role in protein structure and disease; representation on cell surfaces is the glycome.

Glycans play a key role in protein structure and disease; representation on cell surfaces is the glycome.

Protocols

A step-by-step protocol for released N-linked glycan analysis of the monoclonal antibody adalimumab, based on UHPLC-FLR-MS and procainamide labeling.

Questions

1–9 of 9 Questions  
  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer
    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  3. Wir haben eine geringe Menge in Wasser gelöst. Wie können wir den Rest der Lösung (ca 200µl) entsorgen?

    1 answer
    1. Please refer to section 13 of the Safety Data Sheet for disposal information. Consult with facility or municipal EHS authorities to ensure proper guidelines are followed. The SDS may be accessed by using the link provided in the upper left toolbar of the product detail page.

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  4. How should cleaning and handling be done in working environment where sodium cyanoborohydride is used, is there a critical interaction with other chemicals? What is the level of risk of leakage into the working environment?

    1 answer
    1. The following information can be found on the product Safety Data Sheet: Work under hood. Do not inhale substance/mixture. Keep workplace dry. Do not allow product to come into contact with water.

      Store tightly closed. Keep away from heat and sources of ignition. Keep locked up or in an area accessible only to qualified or authorized persons. Never allow product to get in contact with water during storage. Do not store near acids.
      Over time, pressure may increase causing containers to burst hygroscopic Handle and store under inert gas.

      The level of risk of leakage into the working environment has not been determined. Please consult with local or institutional environmental, health, and/or safety departments for site-specific handling. See the link below to review the product Safety Data Sheet for any additional information: https://www.sigmaaldrich.com/sds/aldrich/156159

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

    1 answer
    1. 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.

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

    1 answer
    1. 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.

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

    1 answer
    1. 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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  8. What is Product 156159, Sodium Cyanoborohydride, soluble in?

    1 answer
    1. 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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  9. What impurities are present in Product 156159, Sodium Cyanoborohydride?

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

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