Sodium cyanoborohydride

HCID 5003444CAS 25895-60-7
Substructure searchFind similar structures

Basic information

Standard SMILES
[BH3-]C#N.[Na+]
InChIKey
CVDUGUOQTVTBJH-UHFFFAOYSA-N
Molecular formula
CH3BNNa
Average molar mass
62.84 g/mol
Monoisotopic mass
63.0256235

Names & identifiers

Preferred name
Sodium cyanoborohydride
IUPAC
sodium cyanoboranuide
English name
Sodium cyanoborohydride
Molecular formula
CH3BNNa
Molecular weight
62.84

Names & synonyms

Sodium cyanotrihydroborateDTXSID40894864C4I8C58P9TBorate(1-), (cyano-kappaC)trihydro-, sodium, (T-4)-Borate(1-), (cyano-kappaC)trihydro-, sodium (1:1), (T-4)-sodium cyanohydridoborateNaBH(3)CNsodium cyanoborohydride, borate (1-) ionRefChem:887464DTXCID001838713247-317-225895-60-7
Show more names
NaBH3CNNaCNBH3SODIUM CYANOTRIHYDRIDOBORATESodium cyanoboronhydrideSodium cyanborohydrideCyanoborohydride SodiumCyano sodiuM borohydridesodium (cyano-kappaC)(trihydrido)borate(1-)Sodium cyanoborohydride, 1M solution in THF, AcroSeal
Borate(1-), (cyano-C)trihydro-, sodium, (T-4)-Sodium borocyanohydrideSodium cyanoborohydrideCH3BNNasodiumcyanoborohydrideSodium (cyanido-kappaC)trihydridoborate(1-)CVDUGUOQTVTBJH-UHFFFAOYSA-NSodium (T-4)-(Cyano-C)trihydroborate(1-); Sodium borocyanohydride; Sodium Cyanotrihydroborate; Sodium Cyanotrihydroborate(1-);

Database identifiers

CAS
25895-60-7
PubChem CID
5003444
DTXSID
DTXSID40894864
UNII
C4I8C58P9T
EC Number
247-317-2

Properties

Computed structural properties

Topological polar surface area
23.8 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
0
Heavy atoms
4

Experimental & physicochemical properties

Physical DescriptionWhite hygroscopic solid; [Merck Index] White powder; [Alfa Aesar MSDS]

Physicochemical properties

Melting point
242 °C · >242 °C (dec.) (lit.)
Boiling point
307 °C · 307°C
Density
1.083 g/mL · 1.083 g/mL at 25 °C
Flash point
1 °F · −1 °F
storage temp.
30 °C · 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

Safety & regulation

GHS classification

GHS Classification · 5 items

Danger

H228 (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.

Hazard information

Regulatory Information · 2 items

Chemical: Borate(1-), (cyano-C)trihydro-, sodium, (T-4)-

Sodium cyanoborohydride: HSNO Approval: HSR004685 Approved with controls

Other Safety InformationIMAP assessments - Borate(1-), (cyano-C)trihydro-, sodium, (T-4)-: Human health tier I assessment；IMAP assessments - Borate(1-), (cyano-C)trihydro-, sodium, (T-4)-: Environment tier I assessment
Hazards SummaryReacts with water evolving extremely flammable gases; Causes burns; Highly toxic by ingestion, inhalation, and skin absorption; [Alfa Aesar MSDS]
Hazard Classes and CategoriesFlam. Sol. 1 (97.1%)；Acute Tox. 1 (100%)；Acute Tox. 1 (100%)；Skin Corr. 1B (100%)；Eye Dam. 1 (25%)；Acute Tox. 1 (100%)；Aquatic Acute 1 (75.8%)；Aquatic Chronic 1 (77%)

Toxicology

Adverse EffectsDermatotoxin - Skin burns.

Regulatory information

Regulatory Information · 2 items

Chemical: Borate(1-), (cyano-C)trihydro-, sodium, (T-4)-

Sodium cyanoborohydride: HSNO Approval: HSR004685 Approved with controls

Safety data

F
10-21
PPE
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
wgk
1
tsca
TSCA listed
ridadr
UN 3179 4.1/PG 2
hs_code
28500020

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 1 item

Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499)

Uses & manufacturing

UsesUsed as a reducing agent (aldehydes, ketones, oximes, and enamines); Also used for reductive amination, reductive alkylation, reductive displacement, and deoxygenation; [Merck Index]
Applications · 2 items

DescriptionSodium 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.

UsesSodium 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 methods · 1 item

PreparationSynthesis 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%).

Upstream & downstream products

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
杭州品高化工有限公司0571-87658025 · [email protected]
上海泰矶林实业有限公司02150630626 17717886015 · [email protected]

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