Contact us: +91 9550333722 040 - 40102781
Structured search
India
Choose your country
Different countries will display different contents
Try our best to find the right business for you.
My chemicalbook

Welcome back!

HomeProduct name listSodium cyanoborohydride

Sodium cyanoborohydride

Synonym(s):Sodium borocyanohydride;Sodium cyanoborohydride;Sodium cyanotrihydridoborate;Sodium cyanotrihydroborate

  • CAS NO.:25895-60-7
  • Empirical Formula: CH3BNNa
  • Molecular Weight: 62.84
  • MDL number: MFCD00003516
  • EINECS: 247-317-2
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-12-18 14:15:30
Sodium cyanoborohydride Structural

What is Sodium cyanoborohydride?

Description

Sodium cyanoborohydride (NaBH3CN) is a selective reducing agent used for a variety of chemical reductions, including aldehyde, ketones, acetals, epoxides, oximes, enamines, reductive aminations of aldehydes and ketones, and reductive alkylations of amines and hydrazines. The utility of sodium cyanoborohydride as a reducing agent is greatly enhanced by its stability under acid conditions, and its solubility in aprotic solvents. Sodium cyanoborohydride is a milder and more selective reducing agent than sodium borohydride.
Sodium cyanoborohydride is a weaker and more-selective reducing agent than sodium borohydride because of the electron-withdrawing effect of the cyano group. It has the further advantage that it is stable in acid to pH = 3 and can be employed to effect reductions in the presence of functional groups that are sensitive to the more-basic conditions of reduction with sodium borohydride.
Aldehydes and ketones are unaffected by sodium cyanoborohydride in neutral solution, but they are readily reduced to the corresponding alcohol at pH=3-4 by way of the protonated carbonyl group. By previous exchange of the hydrogens of the borohydride for deuterium or tritium, by reaction with D2O or tritiated water, an efficient and economical route is available for deuteride or tritiide reduction of aldehydes and ketones.

Chemical properties

Sodium cyanoborohydride is a white or slightly yellow solid powder, It is a versatile reducing agent stable in aqueous solution at pH 7.2. It is a weaker reducing agent as compared to NaBH4. It effectively reduces Schiff bases. NaCNBH4 participates in the reductive methylation for the efficient and selective conversion of the e-amino groups of lysyl residues in proteins to the mono- and dimethyl derivatives.

The Uses of Sodium cyanoborohydride

NaBH3CN can effectively be used in H2O and protic solvents (ex. MeOH or EtOH), unlike sodium triacetoxyborohydride (STAB) which is quickly degraded by H2O and protic solvents.

Physical properties

Sodium cyanotrihydridoborate, sodium cyanoborohydride, sodium cyanoboranate, NaBH3CN, is a white, amorphous powder, melting with decomposition at 240 – 242℃. Contact with the atmosphere must be avoided as it is extremely hygroscopic. It is very soluble in polar, especially protic, solvents such as water, alcohols, amines, and THF, but not in diethyl ether or hydrocarbons.

The Uses of Sodium cyanoborohydride

Sodium Cyanoborohydride is a commonly used as a reagent in the reductive amination of aldehydes and ketones and in the reductive alkylation of amines. It is also used in the synthesis of a novel phenolate-bridged dilanthanum(III) complex of interest as a model for metalloproteins as well as for its importance in basic and applied chemistry.

Preparation

Synthesis of Sodium cyanoborohydride(NaBH3CN): NaBH3CN was made by stirring equimolar BH3·THF (~1 M) with NaCN in THF in excellent yield.To a rapidly stirred slurry of sodium borohydride (80.2g, 2.09 mol) in THF (1000mL) in a 2-L flask is added a solution of hydrogen cyanide in THF (294g containing 58.8g of hydrogen cyanide) at 25°C. Evolution of hydrogen occurs slowly during the addition. Following the addition, the reaction mixture is stirred for 1 h at 25°C and then heated at reflux until hydrogen evolution has ceased. Filtration followed by vacuum removal of THF gives white solid sodium cyanoborohydride; yield 120g (91%).

Reactions

Sodium cyanoborohydride are frequently used for reductive aminations. Since the reaction rate for the reduction of iminium ions is much faster than for ketones or even aldehydes, the reductive amination can be carried out as a one-pot procedure by introducing the reducing agent into a mixture of the amine and carbonyl compound.
Contact with strong acids liberates the highly toxic gas HCN. A safer reducing agent with comparable reactivity is sodium triacetoxyborohydride. Reduction with Sodium Cyanoborohydride:
Tin-free Giese reaction of alkyl iodides with electron-deficient alkenes and the related radical carbonylation process proceeded efficiently in the presence of sodium cyanoborohydride and tetrabutylammonium cyanoborohydride. Transfer of iodine followed by hydride reduction of the resulting carbon-iodine bond is proposed as a possible mechanism.
Borch and co-workers showed that sodium cyanoborohydride and lithium cyanoborohydride are acid-stable reagents capable of rapidly reducing carbonyl compounds to alcohols at pH 3-4, presumably via a protonated carbonyl cation.
With care to maintain a pH of 6-7, a mixture of a ketone or aldehyde reactant, an amine, and sodium cyanohydride provides products of reductive amination selectively, without competitive reduction of the carbonyl substrate. Though the conditions of the Borch reduction are mild, sodium cyanoborohydride is highly toxic, as are its byproducts. The pH was maintained by addition of HCl and/or KOH as needed using bromocresol green as an indicator.
Reducing Agents Sodium cyanoborohydride

Preparation

To a solution of 10% AcOH in MeOH was added the SM (1 equiv) and dry acetone (5 equiv). The solution was stirred at RT 1 h, after which time it was cooled to 0 C and treated with NaCNBH3 (1.5 equiv).The reaction was stirred at RT for 5 h. The mixture was concentrated and the residue brought to pH = 10 using Na2CO3. The mixture was extracted with EtOAc and the org layer was washed with H2O, brine, dried (Na2SO4), and concentrated to dryness. The crude material was purified by silica gel column chromatography (2% MeOH/DCM) to provide the pdt as a yellow solid.

Hazard

Flammable solid. Dust may form explosive mixture with air. Fire-water run-off in sewers may create fire or explosion hazard. This product is toxic. Severe corrosive hazard. Water used for fire extinguishing, which has been in contact with the product, may be corrosive.

Chemical Reactivity

Sodium cyanoborohydride is used as a selective reducing agent in the synthesis of pharmaceuticals. Its special reducing properties arise from its remarkable resistance to hydrolysis. It is stable even at pH 3 in water and methanol, its rate of hydrolysis being slower than that of NaBH4 by a factor of 108. Reactivity and stereoselectivity are considerably affected by the nature and acidity of the solvent. In polar aprotic solvents such as hexamethylphosphoric triamide (HMPT) or dimethyl sulfoxide (DMSO) it reduces aliphatic halides and toluenesulfonates to the corresponding hydrocarbons. Under these conditions other reducible functional groups such as epoxides, ketones, and aldehydes are unaffected.

Purification Methods

Sodium cyanoborohydride (10g) is dissolved in THF (80mL) and 1 M methanolic hydrochloric acid is added until pH reaches 9. The solution is then poured with stirring into dioxan (250mL). The precipitate is collected and stirred for 2 h in ethyl acetate (250mL). This solution is filtered, heated to reflux on a steam bath and then dioxan (150mL) is added slowly with swirling. This solution is slowly cooled to room temperature, chilled and filtered. The crystalline dioxan complex is dried in vacuo for 4 h at room temperature, then for 4 h at 80° C; yield 6.74g, purity >98% sodium cyanoborohydride by iodometric titration.

Properties of Sodium cyanoborohydride

Melting point: >242 °C (dec.) (lit.)
Boiling point: 307°C
Density  1.083 g/mL at 25 °C
Flash point: −1 °F
storage temp.  Store below +30°C.
solubility  Soluble in water (100 mg/ml, with heating), methanol, ethanol, and THF. It is insoluble in nonpolar solvents such as benzene or hexane
form  Powder
appearance White solid
color  White
Specific Gravity 1.2
Water Solubility  2120 g/L at 29 ºC (dec.)
Sensitive  Moisture Sensitive
Merck  14,8606
BRN  4152656
Stability: Stable. Hygroscopic. Reacts violently with water, giving off and igniting hydrogen. Do not use water on fires involving this chemical - instead use dry soda ash. Incompatible with strong acids, water, strong oxidizing agents.
CAS DataBase Reference 25895-60-7(CAS DataBase Reference)
EPA Substance Registry System Borate(1-), (cyano-.kappa.C)trihydro-, sodium, (T-4)- (25895-60-7)

Safety information for Sodium cyanoborohydride

Signal word Danger
Pictogram(s)
ghs
Flame
Flammables
GHS02
ghs
Corrosion
Corrosives
GHS05
ghs
Skull and Crossbones
Acute Toxicity
GHS06
ghs
Environment
GHS09
GHS Hazard Statements H228:Flammable solids
H260:Substances And Mixtures Which, In Contact With Water,Emit Flammable Gases
H314:Skin corrosion/irritation
H410:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P260:Do not breathe dust/fume/gas/mist/vapours/spray.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P231+P232:Handle under inert gas. Protect from moisture.
P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Sodium cyanoborohydride

Sodium cyanoborohydride manufacturer

ALTRAKEM PHARMA LIFE SCIENCES PRIVATE LIMITED

2Y
Phone:+91-9966658228
Whatsapp: +91- 9966658228
product: 25895-60-7 Sodium cyanoborohydride 99%
Inquiry

Sintilla Medcoms Pvt Ltd

1Y
Phone:+91-8886733867
Whatsapp: +91 8886733867
product: Sodium cyanoborohydride 98%
Inquiry

Rivashaa Agrotech Biopharma Pvt. Ltd.

1Y
Phone:+91-7926462688
product: 25895-60-7 Sodium cyanoborohydride 98%
Inquiry

ALS INDIA LIFE SCIENCES

1Y
Phone:+91-8977036379
Whatsapp: +91 8008166674
product: 25895-60-7 98%
Inquiry

SLN Pharmachem

1Y
Phone:+91-8655040421
Whatsapp: +91-8655040421
product: Sodium cyanoborohydride 98%
Inquiry

ARRAKIS INDUSTRIES LLP

1Y
Phone:+91-7499586750
Whatsapp: +91- 7499586750
product: SODIUM CYANO BOROHYDRIDE 99%
Inquiry

SS Reagents and Chemicals

1Y
Phone:+91-7981238883
Whatsapp: +91-7981238883
product: 25895-60-7 99%
Inquiry

Anand Agencies

Maharashtra
Phone:91-9075014125
Whatsapp: 91-9075014125
product: Sodium cyanoborohydride
Inquiry

ASM Organics

Andhra Pradesh
Phone:91-9866122393
Whatsapp: 91-9866122393
product: Sodium cyanoborohydride
Inquiry

Related products of tetrahydrofuran

You may like

Statement: All products displayed on this website are only used for non medical purposes such as industrial applications or scientific research, and cannot be used for clinical diagnosis or treatment of humans or animals. They are not medicinal or edible.