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25895-60-7

Basic Information
CAS No.: 25895-60-7
Name: Sodium cyanoborohydride
Article Data: 7
Cas Database
Molecular Structure:
Molecular Structure of 25895-60-7 (Sodium cyanoborohydride)
Formula: NaBH3CN
Molecular Weight: 62.8423
Synonyms: Sodium cyanoborohydride solution;Sodium cyanobrohydide;sodium; boron(+3) cation; hydrogen(-1) anion; cyanide;Borate(1-), (cyano-kappaC)trihydro-, sodium, (T-4)-;Sodium cyanotrihydroborate;
EINECS: 247-317-2
Density: 1.083 g/mL at 25 °C
Melting Point: >242°C (dec.)(lit.)
Boiling Point: 307°C
Flash Point: ?1°F
Solubility: reacts in water
Appearance: white crystalline powder
Hazard Symbols: FlammableF; VeryT+; DangerousN
Risk Codes: 26/27/28-32-34-50/53-16-15-11-51/53-36-23/24/25-19-14
Safety: 26-28-36/37/39-45-60-61-8-50A-43-28A-1-16
Transport Information: UN 3179 4.1/PG 2
PSA: 23.79000
LogP: -1.16712
Synthetic route
846060-69-3

(1S,2R)-1-(3,4-dichlorophenyl)-2-formyl-cyclopropanecarboxylic acid (4-fluorobenzyl)methylamide

52509-14-5

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide

25895-60-7

sodium cyanoborohydride

Conditions
ConditionsYield
With potassium hexamethylsilazane In tetrahydrofuran at 20℃; for 2h;91%
16940-66-2

sodium tetrahydroborate

592-04-1

mercury(II) cyanide

25895-60-7

sodium cyanoborohydride

Conditions
ConditionsYield
In tetrahydrofuran byproducts: Hg, H2; molar ratio Hg:B=1:2, refluxing (3 h); sepn. of Hg;78%
16940-66-2

sodium tetrahydroborate

74-90-8

hydrogen cyanide

25895-60-7

sodium cyanoborohydride

Conditions
ConditionsYield
50 to 150°C;
50 to 150°C;
In tetrahydrofuran
16940-66-2

sodium tetrahydroborate

74-90-8

hydrogen cyanide

A

773837-37-9

sodium cyanide

B

29012-60-0

sodium cyanoborohydride

C

29012-61-1

sodium cyanobis(trihydroborate)

D

25895-60-7

sodium cyanoborohydride

Conditions
ConditionsYield
In tetrahydrofuran Kinetics; byproducts: H2; react. in THF at 20°C; not isolated; detected by NMR and IR;A n/a
B 0%
C n/a
D n/a
25895-60-7

sodium cyanoborohydride

206537-23-7

N-(4-iodobenzyl)hydroxylamine

Conditions
ConditionsYield
Stage #1: p-(iodophenyl)carboxaldehyde With potassium hydroxide; hydroxylamine hydrochloride In tetrahydrofuran; methanol; water at 20℃; for 2h; pH=9;
Stage #2: sodium cyanoborohydride With hydrogenchloride; methyl orange In tetrahydrofuran; methanol; water for 16h; pH=2 - 3;
91%
122-78-1

phenylacetaldehyde

25895-60-7

sodium cyanoborohydride

110755-31-2

isopentyl-phenethyl-amine

Conditions
ConditionsYield
Stage #1: phenylacetaldehyde; sodium cyanoborohydride In methanol at 64℃; for 3h; Borch Reduction;
Stage #2: With sodium cyanoborohydride In methanol; ethanol at 20 - 64℃; for 5h; Borch Reduction;
100%
64-18-6

formic acid

25895-60-7

sodium cyanoborohydride

1606161-69-6

N-benzyloxy-N-((2S,3S,4R)-2,3,4-tris-benzyloxy-5-triisopropylsilanyloxy-pentyl)-formamide

Conditions
ConditionsYield
Stage #1: formic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: sodium cyanoborohydride In tetrahydrofuran at 0 - 20℃;
94%
25895-60-7

sodium cyanoborohydride

212061-26-2

2'-O-[(2-formadoxyiminooxy)ethyl]-5'-O-tert-butyldiphenylsilyl-5-methyluridine

212061-27-3

5'-O-tert-butyldiphenylsilyl-2'-O-[N,N dimethylaminooxyethyl]-5-methyluridine

Conditions
ConditionsYield
Stage #1: 2'-O-[(2-formadoxyiminooxy)ethyl]-5'-O-tert-butyldiphenylsilyl-5-methyluridine With pyridinium p-toluenesulfonate; sodium cyanoborohydride In methanol at 10 - 20℃; for 2.16667h;
Stage #2: With formaldehyd In methanol; water at 20℃; for 0.166667h;
Stage #3: sodium cyanoborohydride In methanol; water at 10 - 20℃; for 2.16667h;
80%
50-00-0

formaldehyd

38989-02-5

1-Aminoapocamphor

25895-60-7

sodium cyanoborohydride

1-Dimethylamino-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one

Conditions
ConditionsYield
Stage #1: formaldehyd; 1-Aminoapocamphor; sodium cyanoborohydride In acetonitrile at 0 - 20℃;
Stage #2: With acetic acid In acetonitrile for 6h;
86%
5368-72-9

2,5-dimethylthiophene-3,4-dicarboxaldehyde

25895-60-7

sodium cyanoborohydride

74-89-5

methylamine

C9H13NS*CH3BN(1-)*H(1+)

Conditions
ConditionsYield
With acetic acid In methanol at 20℃; for 18h; Inert atmosphere; Schlenk technique;86%
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Specification

The Sodium Cyanoborohydride, with the CAS registry number 25895-60-7 and EINECS registry number 247-317-2, is also called Sodium cyanotrihydroborate. It is a kind of white solid which is moisture sensitive, and belongs to the following prodcut categories: Selectivity reducing agent; B (Classes of Boron Compounds); Classes of Metal Compounds; Na (Sodium) Compounds (excluding simple sodium salts); Reduction; Synthetic Organic Chemistry; Tetrahydroborates; Typical Metal Compounds; Borohydrides; Synthetic Reagents. And the molecular formula of the chemical is NaBH3CN. What's more, it should be stored under Argon.

The physical properties of Sodium Cyanoborohydride are as followings: (1)#H bond acceptors: 1; (2)#H bond donors: 0; (3)#Freely Rotating Bonds: 0; (4)Polar Surface Area: 23.79 Å2.

Preparation and uses of Sodium Cyanoborohydride: It can be prepared either by treating sodium cyanide with borane, or by reacting sodium borohydride with mercury(II) cyanide. It is widely used in organic synthesis for the reduction of imines. And it is usually used as a mild reducing agent which converts imines to amines. And because of its selectivity, this chemical is ideal for reductive aminations at mildly basic solutions (pH 7-10).

You should be cautious while dealing with this chemical. It is a kind of highly flammable chemical which is also very toxic. If contacting with water, it will liberate extremely flammable gases, and explosive when mixed with oxidizing substances. And if contact with acids, it will liberate very toxic gas. And it may also cause burns. It is very toxic by inhalation, in contact with skin and if swallowed. It is very toxic to aquatic organisms, and may cause long-term adverse effects in the aquatic environment. Therefore, you had better take the following instructions: Keep locked up; Keep container dry; Wear suitable protective clothing, gloves and eye/face protection, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice; Avoid release to the environment. This material and/or its container must be disposed of as hazardous waste; Refer to special instructions safety data sheet; Do not mix with...(to be specified by the manufacturer); After contact with skin, wash immediately with plenty of... (to be specified by the manufacturer).

You can still convert the following datas into molecular structure:
(1)SMILES: [Na+].N#C[BH3-]
(2)InChI: InChI=1/CH3BN.Na/c2-1-3;/h2H3;/q-1;+1
(3)InChIKey: CVDUGUOQTVTBJH-UHFFFAOYAX

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