UNIVERSITY INSTITUTE OF SCIENCES

DIVISION-CHEMISTRY
Masters Of Sciences (Chemistry)
Advance Organic Chemistry
22SHT701

DISCOVER . LEARN . EMPOWER

By: komal Sharma
 Reduction with Sodium Cyanoborohydride (NaBH3CN)

Sodium cyanoborohydride (NaBH₃CN) is a chemical compound that serves as a mild

reducing agent in organic chemistry. While there isn't a comprehensive historical account
specifically dedicated to sodium cyanoborohydride, its development and use are part of the
broader history of boron-based reducing agents in organic synthesis.

1. Discovery of Boron Hydrides:

• The history of boron hydrides dates back to the early 20th century. In the 1910s and
1920s, pioneering work by scientists like Alfred Stock and H. I. Schlesinger led to the
discovery and understanding of various boron hydrides, including sodium borohydride
(NaBH₄).
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 CONTD.

2. Development of Sodium Cyanoborohydride:

• The synthesis of sodium cyanoborohydride specifically involves the introduction of cyanide (CN ⁻) into

the borohydride structure. The compound was likely developed as an extension of the studies involving

boron hydrides and their applications in organic synthesis. The exact historical details of this specific

compound's development are not widely documented.

3. Application in Organic Synthesis:

• Sodium cyanoborohydride found its place as a milder and more selective reducing agent compared to

sodium borohydride in the reduction of various functional groups, including aldehydes and ketones. Its

mildness makes it particularly suitable for substrates sensitive to

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CONTD.

harsher reducing agents like lithium aluminum hydride (LiAlH₄).

4. Modern Applications and Research:

• Over the years, sodium cyanoborohydride has become a staple reagent in organic

synthesis, especially in the production of pharmaceuticals and fine chemicals.

Researchers continue to explore its applications, often in combination with other

reagents and catalysts, leading to more efficient and selective reduction methods.

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 Sodium cyan borohydride

Sodium cyan borohydride is a weak reducing agent which is used in reductive

aminations. Reductive aminations are the processes in which the carbonyl compounds
(it may be ketones or aldehydes) are converted to amines by a formation of an
intermediate imine. This reduction requires slightly acidic conditions. If the conditions
are very acidic than carbonyl group gets protonated and the rate of addition to the
carbon of carbonyl group become faster.

CN

B Na
H
H H

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 Preparation
Sodium cyano borohydride (NaBH3​CN) is typically prepared by the reaction of sodium
borohydride NaBH4​) with hydrogen cyanide (HCN). The reaction can be represented as
follows:

TH F
NaBH 4 + HCN NaBH 3CN + H2

In this reaction:

Sodium borohydride (NaBH4​) acts as the source of the borohydride ion (BH4−).

Hydrogen cyanide (HCN) provides the cyanide ion (CN−).

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 CONTD.

The borohydride ion and cyanide ion combine to form sodium cyanoborohydride
(NaBH3CN).

Hydrogen gas (H2​) is evolved as a byproduct and can be observed as bubbles.

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 GENERAL

Aldehyde
O

R H

O
NaCNBH3
No Reduction.
R R' Neutral ph

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Sodium cyanoborohydride reduced only under an acidic medium
Not reduced under neutral pH.
O
NaCNBH3
Primary Alcohols

R H Acidic ph (3-4) R OH

O OH
NaCNBH3

R R' Acidic ph (3-4) R R'

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 CHEMOSELECTIVE REDUCING Agent

O O O
NaCNBH3

MeOH, HCl
R H R OH
EXAMPLE

COOEt COOEt

NaCNBH3
O OH
N ph=4
N
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 Reductive amination
H N C N
O +

ph=(6-8) NaCNBH3

MeOH

CH N

EXAMPLE

O NHEt

(a) EtNH2, MeOH,

NaCNBH3

COOEt
ph=6 COOEt
(b)NaOH, H2O 11
 Deoxygenation via tosyl hydro sone
reduction
NH2NHTs DMF, NaCNBH3
R C NNHTs R CH3
R CHO

EXAMPLE

(a)H2NNHTs

(b)NaCNBH3, DMF

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1. It is a white solid.
2. It is very toxic.
3. Its other name of it is sodium cyanotrihydridoborate.
4. These solids can tolerate aqueous conditions.
5. Sodium cyanoborohydride is a weak reducing agent.
6. It is basically used for reductive aminations.
7. For the reduction of iminium ions, the rate of reaction is faster than the rate of
reduction of carbonyl compounds.

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APPLICATIONS

• Pharmaceutical Industry: It is used in the synthesis of pharmaceuticals and drug

intermediates. The reduction reactions it facilitates are key steps in the production
of many medications.

• Chemical Research: Sodium cyanoborohydride is widely used by researchers in

organic chemistry laboratories for the reduction of various functional groups. Its
selectivity and milder reaction conditions make it a popular choice.

• Material Science: It is used in the synthesis of materials like polymers and resins,
where specific chemical functionalities need to be reduced or modified. 14
• Flavor and Fragrance Industry: Sodium cyanoborohydride is utilized in the production of
flavors and fragrances, where precise control over the chemical structure is necessary to achieve
desired aromas and tastes

• Agrochemicals: In the synthesis of agrochemicals, such as pesticides and herbicides, sodium

cyanoborohydride can be employed to create specific chemical compounds needed for pest control.

• Peptide Chemistry: It is used in peptide chemistry for the reduction of peptide bonds without
affecting other sensitive functional groups in the molecule

• Analytical Chemistry: Sodium cyanoborohydride is used in analytical techniques like High-

Performance Liquid Chromatography (HPLC) for the derivatization of compounds, enabling their
detection and quantification.

• Biochemical Research: In biochemical research, it can be used for the reduction of certain
biomolecules, aiding in the study of biological processes
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Disadvantage
Sometimes strong acid can release hydrogen cynacid from NaBH3CN

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