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25895-60-7

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Identification

Name
Sodium cyanoborohydride
CAS
25895-60-7
Synonyms
SODIUM CYANOBOROHYDRIDE
SODIUM CYANOTRIHYDRIDOBORATE
SODIUM CYANOTRIHYDROBORATE
(cyano-C)trihydro-,sodium,(T-4)-Borate(1-)
sodium,(beta-4)-borate(1-(cyano-c)trihydro-
Sodium cyonobrohydriole
SODIUM CYANOBOROHYDRIDE, 5.0M SOLUTION I N AQUEOUS CA. 1M SODIUM HYDROXIDE
SODIUM CYANOBOROHYDRIDE, 1.0M SOLUTION I N TETRAHYDROFURAN
Sodiumcyanoborohydride,95%
Borate(1-), (cyano-.kappa.C)trihydro-, sodium, (T-4)-
sodium cyanoborohydride solution
Sodium Cyanoborohydride [Reducing Agent]
Sodium cyanotrihydridoborate, typically 95%
Borate(1-), (cyano-kC)trihydro-, sodium, (T-4)-
Sodium borocyanohydride
Sodium cyanotrihydroborate(1-)
EINECS(EC#)
247-317-2
Molecular Formula
CH3BNNa
MDL Number
MFCD00003516
Molecular Weight
62.84
MOL File
25895-60-7.mol

Chemical Properties

Appearance
White solid
mp 
>242 °C (dec.)(lit.)

bp 
307°C
density 
1.083 g/mL at 25 °C

Fp 
−1 °F

storage temp. 
Store under Argon
solubility 
H2O: may be clear to slightly hazy

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.
Water Solubility 
2120 g/L at 29 ºC (dec.)
Sensitive 
Moisture Sensitive
Merck 
14,8606
CAS DataBase Reference
25895-60-7(CAS DataBase Reference)
Storage Precautions
Store under nitrogen;Moisture sensitive
EPA Substance Registry System
25895-60-7(EPA Substance)

Safety Data

Hazard Codes 
T+,N,T,F
Risk Statements 
R26/27/28:Very Toxic by inhalation, in contact with skin and if swallowed .
R32:Contact with acids liberates very toxic gas.
R34:Causes burns.
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R16:Explosive when mixed with oxidizing substances.
R15:Contact with water liberates extremely flammable gases.
R11:Highly Flammable.
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R36:Irritating to the eyes.
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R19:May form explosive peroxides.
R14:Reacts violently with water.
Safety Statements 
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S8:Keep container dry .
S43:In case of fire, use ... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add-Never use water) .
S1:Keep locked up .
S16:Keep away from sources of ignition-No smoking .
RIDADR 
UN 3179 4.1/PG 2

WGK Germany 
1


10-21
Hazard Note 
Toxic/Highly Flammable
HazardClass 
6.1
PackingGroup 
I
HS Code 
28500020

Raw materials And Preparation Products

Material Safety Data Sheet(MSDS)

Questions And Answer(Q&A)

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.

Questions and Answers (Q&A)

Reducing Agents
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:
  1. 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.
  2. 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.
  3. 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

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