Sodium cyanoborohydride
NaBH3CN · NaCNBH3 · SODIUM CYANOTRIHYDROBORATE · SODIUM CYANOTRIHYDRIDOBORATE · Sodium cyanoboronhydride · Sodium cyanborohydride · Cyanoborohydride Sodium · Cyano sodiuM borohydride
Identifiers & Physical Properties
| CAS No. | 25895-60-7 |
|---|---|
| Molecular formula | CH3BNNa |
| Average molar mass | 62.84 g/mol |
| Monoisotopic mass | 63.0256235 g/mol |
| SMILES | [BH3-]C#N.[Na+] |
| InChIKey | CVDUGUOQTVTBJH-UHFFFAOYSA-N |
| PubChem CID | 5003444 |
| EC No. | 247-317-2 |
| DTXSID | DTXSID40894864 |
Chemical & Physical Properties
| Topological polar surface area | 23.8 |
|---|---|
| Hydrogen bond donors | 0 |
| Hydrogen bond acceptors | 2 |
| Rotatable bonds | 0 |
| Heavy atoms | 4 |
| Formal charge | 0 |
| Complexity | 34 |
| Physical Description | White hygroscopic solid[Merck Index] White powder[Alfa Aesar MSDS] |
| Melting point | >242 °C (dec.) (lit.) |
| Boiling point | 307°C |
| Density | 1.083 g/mL at 25 °C |
| Flash point | −1 °F |
| Storage conditions | 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 hexane2120 g/L at 29 ºC (dec.) |
| Physical state | Powder |
| Color | White |
| Specific gravity | 1.2 |
| Biological source | synthetic |
| Sensitivity | 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. |
| InChI | 1S/CH3BN.Na/c2-1-3/h2H3/q-1+1 |
| InChIKey | CVDUGUOQTVTBJH-UHFFFAOYSA-N |
| SMILES | [Na+].[BH3-]C#N |
| CAS DataBase Reference | 25895-60-7(CAS DataBase Reference) |
| FDA UNII | C4I8C58P9T |
| EPA Substance Registry System | Borate(1-), (cyano-.kappa.C)trihydro-, sodium, (T-4)- (25895-60-7) |
| UNSPSC Code | 12352306 |
| NACRES | NA.22 |
| GHS pictogram | GHS02,GHS05,GHS06,GHS09 |
| Signal word | Danger |
| GHS hazard statements | H228-H260-H300+H310+H330-H314-H410 |
| GHS precautionary statements | P210-P231+P232-P260-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338 |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges |
| Hazard symbols | T+,N,T,F |
| Risk statements (R) | 26/27/28-32-34-50/53-16-15-11-51/53-36-23/24/25-19-14-40-36/37/38 |
| Safety statements (S) | 26-28-36/37/39-45-60-61-8-50A-43-28A-1-16-36/37 |
| UN transport number | UN 3179 4.1/PG 2 |
| Water hazard class (WGK) | 1 |
| F | 10-21 |
| Hazard Note | Toxic/Highly Flammable |
| TSCA inventory status | TSCA listed |
| Hazard class | 6.1Acute Tox. 2 DermalAcute Tox. 2 InhalationAcute Tox. 2 OralAquatic Acute 1Aquatic Chronic 1Eye Dam. 1Flam. Sol. 1Skin Corr. 1BWater-react 1 |
| Packing group | I |
| Customs code | 28500020 |
| Storage class | 4.3 - Hazardous materials which set free flammable gases upon contact with water |
| Excepted quantities | Not Permitted as Excepted Quantity |
Safety & Regulations
| GHS classification | DangerH228 (97.1%): Flammable solid [Danger Flammable solids]H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]H310 (100%): Fatal in contact with skin [Danger Acute toxicity, dermal]H314 (100%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]H318 (25%): Causes serious eye damage [Danger Serious eye damage/eye irritation]H330 (100%): Fatal if inhaled [Danger Acute toxicity, inhalation]H400 (75.8%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]H410 (77%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]P210, P240, P241, P260, P262, P264, P264+P265, P270, P271, P273, P280, P284, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P320, P321, P330, P361+P364, P363, P370+P378, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 244 reports by companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatory information | Chemical: Borate(1-), (cyano-C)trihydro-, sodium, (T-4)-Sodium cyanoborohydride: HSNO Approval: HSR004685 Approved with controls |
| Other safety information | IMAP assessments - Borate(1-), (cyano-C)trihydro-, sodium, (T-4)-: Human health tier I assessmentIMAP assessments - Borate(1-), (cyano-C)trihydro-, sodium, (T-4)-: Environment tier I assessment |
| Hazards summary | Reacts with water evolving extremely flammable gasesCauses burnsHighly toxic by ingestion, inhalation, and skin absorption[Alfa Aesar MSDS] |
| Hazard Classes and Categories | Flam. Sol. 1 (97.1%)Acute Tox. 1 (100%)Skin Corr. 1B (100%)Eye Dam. 1 (25%)Aquatic Acute 1 (75.8%)Aquatic Chronic 1 (77%) |
| Adverse effects | Dermatotoxin - Skin burns. |
| F | 10-21 |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges |
| Water hazard class (WGK) | 1 |
| TSCA inventory status | TSCA listed |
| UN transport number | UN 3179 4.1/PG 2 |
| Customs code | 28500020 |
| Risk statements (R) | 26/27/28-32-34-50/53-16-15-11-51/53-36-23/24/25-19-14-40-36/37/38 |
| Signal word | Danger |
| GHS pictogram | GHS02,GHS05,GHS06,GHS09 |
| Hazard symbols | T+,N,T,F |
| hazard_note | Toxic/Highly Flammable |
| Safety statements (S) | 26-28-36/37/39-45-60-61-8-50A-43-28A-1-16-36/37 |
| Hazard class | 6.1Acute Tox. 2 DermalAcute Tox. 2 InhalationAcute Tox. 2 OralAquatic Acute 1Aquatic Chronic 1Eye Dam. 1Flam. Sol. 1Skin Corr. 1BWater-react 1 |
| Storage class | 4.3 - Hazardous materials which set free flammable gases upon contact with water |
| Packing group | I |
| GHS hazard statements | H228-H260-H300+H310+H330-H314-H410 |
| Excepted quantities | Not Permitted as Excepted Quantity |
| GHS precautionary statements | P210-P231+P232-P260-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338 |
Applications & Uses
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.
Uses
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
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%).