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Sodium cyanoborohydride

Sodium cyanoborohydride
Sodium cyanoborohydride
CAS No.
25895-60-7
Chemical Name:
Sodium cyanoborohydride
Synonyms
SODIUM CYANOBOROHYDRIDE;Sodium cyonobrohydriole;Sodium borocyanohydride;sodium cyanoboronhydide;Cyano sodiuM borohydride;SodiuM cyanohydridoborate;Sodiumcyanoborohydride,95%;SODIUM CYANOTRIHYDROBORATE;SODIUM CYANOTRIHYDRIDOBORATE;Sodium cyanotrihydroborate(1-)
CBNumber:
CB8712127
Molecular Formula:
CH3BNNa
Formula Weight:
62.84
MOL File:
25895-60-7.mol

Sodium cyanoborohydride Properties

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 under Argon
solubility 
H2O: may be clear to slightly hazy
form 
Powder
color 
White
Water Solubility 
2120 g/L at 29 ºC (dec.)
Sensitive 
Moisture Sensitive
Merck 
14,8606
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
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
Hazard Codes  T+,N,T,F
Risk Statements  26/27/28-32-34-50/53-16-15-11-51/53-36-23/24/25-19-14-40-36/37/38
Safety Statements  26-28-36/37/39-45-60-61-8-50A-43-28A-1-16-36/37
RIDADR  UN 3179 4.1/PG 2
WGK Germany  1
10-21
Hazard Note  Toxic/Highly Flammable
TSCA  Yes
HazardClass  6.1
PackingGroup  I
HS Code  28500020
Symbol(GHS):
Signal word: Danger
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H225 Highly Flammable liquid and vapour Flammable liquids Category 2 Danger P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H228 Flammable solid Flammable solids Category 1
Category 2
Danger
Warning
P210, P240,P241, P280, P370+P378
H261 In contact with water releases flammable gas Substances And Mixtures Which, In Contact With Water,Emit Flammable Gases Category 2
Category 3
Danger
Warning
P231+P232, P280, P370+P378,P402+P404, P501
H300 Fatal if swallowed Acute toxicity,oral Category 1, 2 Danger P264, P270, P301+P310, P321, P330,P405, P501
H310 Fatal in contact with skin Acute toxicity,dermal Category 1, 2 Danger P262, P264, P270, P280, P302+P350,P310, P322, P361, P363, P405, P501
H314 Causes severe skin burns and eye damage Skin corrosion/irritation Category 1A, B, C Danger P260,P264, P280, P301+P330+ P331,P303+P361+P353, P363, P304+P340,P310, P321, P305+ P351+P338, P405,P501
H318 Causes serious eye damage Serious eye damage/eye irritation Category 1 Danger P280, P305+P351+P338, P310
H330 Fatal if inhaled Acute toxicity,inhalation Category 1, 2 Danger P260, P271, P284, P304+P340, P310,P320, P403+P233, P405, P501
H335 May cause respiratory irritation Specific target organ toxicity, single exposure;Respiratory tract irritation Category 3 Warning
H351 Suspected of causing cancer Carcinogenicity Category 2 Warning P201, P202, P281, P308+P313, P405,P501
H400 Very toxic to aquatic life Hazardous to the aquatic environment, acute hazard Category 1 Warning P273, P391, P501
H410 Very toxic to aquatic life with long lasting effects Hazardous to the aquatic environment, long-term hazard Category 1 Warning P273, P391, P501
Precautionary statements:
P210 Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P223 Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P260 Do not breathe dust/fume/gas/mist/vapours/spray.
P264 Wash hands thoroughly after handling.
P264 Wash skin thouroughly after handling.
P273 Avoid release to the environment.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P284 Wear respiratory protection.
P320 Specific treatment is urgent (see … on this label).
P303+P361+P353 IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304+P340 IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P370+P378 In case of fire: Use … for extinction.
P405 Store locked up.
P403+P233 Store in a well-ventilated place. Keep container tightly closed.
P403+P235 Store in a well-ventilated place. Keep cool.

Sodium cyanoborohydride price More Price(24)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 156159 Sodium cyanoborohydride reagent grade, 95% 25895-60-7 10g $51.2 2018-11-13 Buy
Sigma-Aldrich 156159 Sodium cyanoborohydride reagent grade, 95% 25895-60-7 1kg $1600 2018-11-13 Buy
TCI Chemical S0396 Sodium Cyanoborohydride [Reducing Agent] >95.0%(T) 25895-60-7 5g $30 2017-12-01 Buy
TCI Chemical S0396 Sodium Cyanoborohydride [Reducing Agent] >95.0%(T) 25895-60-7 25g $91 2017-12-01 Buy
Alfa Aesar 087839 Sodium cyanoborohydride, 95% 25895-60-7 5g $23.3 2018-11-16 Buy

Sodium cyanoborohydride Chemical Properties,Uses,Production

Chemical Properties

White solid

Uses

  1. Sodium Cyanoborohydride is a commonly used as a reagent in the reductive amination of aldehydes and ketones and in the reductive alkylation of amines.
  2. Reagent for selective reductions.
  3. 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.

Uses

Selective reducing agent for aldehydes, ketones, oximes, enamines; does not reduce amides, ethers, lactones, nitriles, nitro Compounds and epoxides. Also used for reductive amination of ketones and aldehydes, reductive alkylation of amines and hydrazines, reductive displacement of halides and tosylates, deoxygenation of aldehydes and ketones. See Lane, loc. cit.

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

Purification Methods

It is avery hygroscopic solid, soluble in H2O (212% at 29o, 121% at 88o), tetrahydrofuran (37% at 28o, 42.2% at 62o), very soluble in MeOH, slightly soluble in EtOH but insoluble in Et2O, *C6H6 and hexane. It is stable to acid up to pH 3 but is hydrolysed in 12N HCl. The rate of hydrolysis at pH 3 is 10-8 times that of NaBH4. The fresh commercially available material is usually sufficiently pure. If very pure material is required, one of the following procedures can be used [Lane Synthesis 135 1975]: (a) The NaBH3CN is dissolved in tetrahydrofuran (20% w/v), filtered and the filtrate is treated with a fourfold volume of CH2Cl2. The solid is collected and dried in a vacuum [Wade et al. Inorg Chem. 9 2146 1970]. (b) NaBH3CN is dissolved in dry MeNO3, filtered, and the filtrate is poured into a 10-fold volume of CCl4 with vigorous stirring; the white precipitate is collected, washed several times with CCl4 and dried in a vacuum (yield 75%) [Berschied & Purcell Inorg Chem 9 624 1970]. (c) When the above procedures fail to give a clean product, then dissolve NaBH3CN (10g) in tetrahydrofuran (80mL) and add N MeOH/HCl until the pH is 9. Pour the solution with stirring into dioxane (250mL). The solution is filtered and heated to reflux. A further volume of dioxane (150mL) is added slowly with swirling. The solution is cooled slowly to room temperature, then chilled in ice and the crystalline dioxane complex is collected, dried in a vacuum for 4hours at 25o, then 4hours at 80o to yield the amorphous dioxane-free powder (6.7g) with purity >98% [Borch et al. J Am Chem Soc 93 2897 1971]. The purity can be checked by iodometric titration [Lyttle et al. Anal Chem 24 1843 1952].

Sodium cyanoborohydride Preparation Products And Raw materials

Raw materials

Preparation Products


Sodium cyanoborohydride Suppliers

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View Lastest Price from Sodium cyanoborohydride manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2018-08-16 Sodium cyanoborohydride
25895-60-7
US $1.00 / KG 1G 98% 100KG

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