25895-60-7

Basic information

• Product Name: Sodium cyanoborohydride
• Synonyms: (cyano-C)trihydro-,sodium,(T-4)-Borate(1-);sodium,(beta-4)-borate(1-(cyano-c)trihydro-;SODIUM CYANOBOROHYDRIDE;SODIUM CYANOTRIHYDRIDOBORATE;SODIUM CYANOTRIHYDROBORATE;Sodium cyonobrohydriole;SODIUM CYANOBOROHYDRIDE, 5.0M SOLUTION I N AQUEOUS CA. 1M SODIUM HYDROXIDE;SODIUM CYANOBOROHYDRIDE, 1.0M SOLUTION I N TETRAHYDROFURAN
• CAS NO: 25895-60-7
• Molecular Formula: CH₃BN*Na
• Molecular Weight: 62.84
• EINECS: 247-317-2
• Product 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;borane
• Mol File: 25895-60-7.mol

Chemical Properties

• Melting Point: >242 °C (dec.)(lit.)
• Boiling Point: 307°C
• Flash Point: −1 °F
• Appearance: White/Powder
• Density: 1.083 g/mL at 25 °C
• Storage Temp.: Store under Argon
• Solubility: H2O: may be clear to slightly hazy
• Water Solubility: 2120 g/L at 29 ºC (dec.)
• Sensitive: Moisture Sensitive
• Stability: Stable. Hygroscopic. Reacts violently with water, giving off and igniting hydrogen. Do not use water on fires involving this che
• Merck: 14,8606
• BRN: 4152656
• CAS DataBase Reference: Sodium cyanoborohydride(CAS DataBase Reference)
• NIST Chemistry Reference: Sodium cyanoborohydride(25895-60-7)
• EPA Substance Registry System: Sodium cyanoborohydride(25895-60-7)

Safety Data

• Hazard Codes: T+,N,T,F
• 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
• F: 10-21
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: I
• Hazardous Substances Data: 25895-60-7(Hazardous Substances Data)

Usage

InChI:InChI=1/CH3BN.Na/c2-1-3;/h2H3;/q-1;+1

Synthetic route

(1S,2R)-1-(3,4-dichlorophenyl)-2-formyl-cyclopropanecarboxylic acid (4-fluorobenzyl)methylamide (846060-69-3) + (1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide (52509-14-5) → sodium cyanoborohydride (25895-60-7)

Conditions	Yield
With potassium hexamethylsilazane In tetrahydrofuran at 20℃; for 2h;	91%

sodium tetrahydroborate (16940-66-2) + mercury(II) cyanide (592-04-1) → sodium cyanoborohydride (25895-60-7)

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

sodium tetrahydroborate (16940-66-2) + hydrogen cyanide (74-90-8) → sodium cyanoborohydride (25895-60-7)

Conditions	Yield
50 to 150°C;
50 to 150°C;
In tetrahydrofuran

sodium tetrahydroborate (16940-66-2) + hydrogen cyanide (74-90-8) → sodium cyanide (773837-37-9) + sodium cyanoborohydride (29012-60-0) + sodium cyanobis(trihydroborate) (29012-61-1) + sodium cyanoborohydride (25895-60-7)

Conditions	Yield
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

sodium cyanoborohydride (25895-60-7) → N-(4-iodobenzyl)hydroxylamine (206537-23-7)

Conditions	Yield
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%

phenylacetaldehyde (122-78-1) + sodium cyanoborohydride (25895-60-7) → isopentyl-phenethyl-amine (110755-31-2)

Conditions	Yield
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%

formic acid (64-18-6) + sodium cyanoborohydride (25895-60-7) → N-benzyloxy-N-((2S,3S,4R)-2,3,4-tris-benzyloxy-5-triisopropylsilanyloxy-pentyl)-formamide (1606161-69-6)

Conditions	Yield
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%

sodium cyanoborohydride (25895-60-7) + 2'-O-[(2-formadoxyiminooxy)ethyl]-5'-O-tert-butyldiphenylsilyl-5-methyluridine (212061-26-2) → 5'-O-tert-butyldiphenylsilyl-2'-O-[N,N dimethylaminooxyethyl]-5-methyluridine (212061-27-3)

Conditions	Yield
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%

formaldehyd (50-00-0) + 1-Aminoapocamphor (38989-02-5) + sodium cyanoborohydride (25895-60-7) → 1-Dimethylamino-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one

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

2,5-dimethylthiophene-3,4-dicarboxaldehyde (5368-72-9) + sodium cyanoborohydride (25895-60-7) + methylamine (74-89-5) → C9H13NS*CH3BN(1-)*H(1+)

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

2,5-dimethylthiophene-3,4-dicarboxaldehyde (5368-72-9) + sodium cyanoborohydride (25895-60-7) + ethylamine (75-04-7) → C10H15NS*CH3BN(1-)*H(1+)

Conditions	Yield
With acetic acid In methanol at 20℃; for 18h; Inert atmosphere; Schlenk technique;	88%

2,5-dimethylthiophene-3,4-dicarboxaldehyde (5368-72-9) + isobutylamine (78-81-9) + sodium cyanoborohydride (25895-60-7) → C12H19NS*CH3BN(1-)*H(1+)

Conditions	Yield
With acetic acid In methanol at 20℃; for 18h; Inert atmosphere; Schlenk technique;	85%

2,2,2-trifluoro-1-(4‘-(methylsulfonyl)-[1,1'-biphenyl]-4-yl)ethanone (893407-18-6) + sodium cyanoborohydride (25895-60-7) + ethyl (2S)-2-amino-4-fluoro-4-methylpentanoate sulfate salt → (S)-4-fluoro-4-methyl-2-(((S)-2,2,2-trifluoro-1-(4’-(methylsulfonyl)-[1,1'-biphenyl]-4-yl)ethyl)amino)pentanoic acid (875272-89-2)

Conditions	Yield
Stage #1: 2,2,2-trifluoro-1-(4‘-(methylsulfonyl)-[1,1'-biphenyl]-4-yl)ethanone; ethyl (2S)-2-amino-4-fluoro-4-methylpentanoate sulfate salt With potassium carbonate In methanol at 50℃; for 16h; Stage #2: sodium cyanoborohydride With methanol at 50℃; for 4h;	86.2%

5-formyl-2,2-dimethyl-4H-[1,3]dioxino[4,5-c]pyridine-8-carboxylic acid methyl ester (1198621-67-8) + sodium cyanoborohydride (25895-60-7) + 4-fluoroaniline (371-40-4) → methyl 5-((4-fluorophenylamino)methyl)-2,2-dimethyl-4H-[1,3]dioxino[4,5-c]pyridine-8-carboxylate (1198621-26-9)

Conditions	Yield
Stage #1: 5-formyl-2,2-dimethyl-4H-[1,3]dioxino[4,5-c]pyridine-8-carboxylic acid methyl ester; 4-fluoroaniline With acetic acid In methanol at 20℃; for 0.25h; Stage #2: sodium cyanoborohydride In methanol at 20℃; for 3h;	96%

9-fluorenylmethoxy carbonyl-4-piperidone + t-butoxycarbonylhydrazine (870-46-2) + sodium cyanoborohydride (25895-60-7) → C25H29N3O4

Conditions	Yield
Stage #1: 9-fluorenylmethoxy carbonyl-4-piperidone; t-butoxycarbonylhydrazine In methanol for 3h; Heating / reflux; Stage #2: sodium cyanoborohydride; titanium tetrachloride In methanol at 20℃; for 2h;	80%

propylamine (107-10-8) + 2,5-dimethylthiophene-3,4-dicarboxaldehyde (5368-72-9) + sodium cyanoborohydride (25895-60-7) → C11H17NS*CH3BN(1-)*H(1+)

Conditions	Yield
With acetic acid In methanol at 20℃; for 18h; Inert atmosphere; Schlenk technique;	83%

2,5-dimethylthiophene-3,4-dicarboxaldehyde (5368-72-9) + sodium cyanoborohydride (25895-60-7) + isopropylamine (75-31-0) → C11H17NS*CH3BN(1-)*H(1+)

Conditions	Yield
With acetic acid In methanol at 20℃; for 18h; Inert atmosphere; Schlenk technique;	80%

2,5-dimethylthiophene-3,4-dicarboxaldehyde (5368-72-9) + sodium cyanoborohydride (25895-60-7) + tert-butylamine (75-64-9) → C12H19NS*CH3BN(1-)*H(1+)

Conditions	Yield
With acetic acid In methanol at 20℃; for 18h; Inert atmosphere; Schlenk technique;	82%

C17H14FN3O2S + sodium cyanoborohydride (25895-60-7) → C18H19FN4OS

Conditions	Yield
With titanium(IV)isopropoxide In tetrahydrofuran at 20℃; for 12h;	70%

N-benzyl-3-pyrrolidinone (775-16-6) + t-butoxycarbonylhydrazine (870-46-2) + sodium cyanoborohydride (25895-60-7) → tert-butyl 2-(1-benzylpyrrolidin-3-yl)hydrazinecarboxylate (1292303-81-1)

Conditions	Yield
Stage #1: N-benzyl-3-pyrrolidinone; t-butoxycarbonylhydrazine With acetic acid In methanol at 20℃; for 1h; Stage #2: sodium cyanoborohydride In methanol at 20℃; for 12h;	57%

sodium cyanoborohydride (25895-60-7) + methyl 1-(2-propenyl)-2-oxocyclopentanecarboxylate (74036-93-4, 111239-40-8) → C10H17NO2

Conditions	Yield
With ammonium acetate In methanol at 50℃; for 4h; Inert atmosphere;	50%

benzyl 2-formyl-7-azaspiro[3.5]nonane-7-carboxylate (1227610-18-5) + sodium cyanoborohydride (25895-60-7) + methylamine (74-89-5) → benzyl 2-((methylamino)methyl)-7-azaspiro[3.5]nonane-7-carboxylate

Conditions	Yield
Stage #1: benzyl 2-formyl-7-azaspiro[3.5]nonane-7-carboxylate; methylamine With titanium(IV) isopropylate In tetrahydrofuran; 1,2-dichloro-ethane at 20℃; Stage #2: sodium cyanoborohydride In tetrahydrofuran; 1,2-dichloro-ethane at 20℃; for 1h;	63.7%

(2aS,4R,8aS)-8-allyloxycarbonyl-4-[(R)-6-benzyloxyheptyl]-7-methyl-1,2,2a,5,6,7,8,8a-octahydro-5,6,8b-triazaacenaphtylen-8b-ylium (865777-39-5) + sodium cyanoborohydride (25895-60-7) → (2aS,4R,7R,8aS)-4-[(6R)-6-benzyloxyheptyl]-7-methyl-1,2,2a,3,4,5,6,7,8,8a-decahydro-5,6,8b-triazaacenaphtylen-8b-ylium cyanide

Conditions	Yield
Stage #1: (2aS,4R,8aS)-8-allyloxycarbonyl-4-[(R)-6-benzyloxyheptyl]-7-methyl-1,2,2a,5,6,7,8,8a-octahydro-5,6,8b-triazaacenaphtylen-8b-ylium With pyrrolidine; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; methanol at 20℃; for 1h; Stage #2: sodium cyanoborohydride With acetic acid In methanol at 20℃; for 1h;	85%

4-(chloromethyl)-1-(2,4-dichlorophenyl)-1H-pyrazole + sodium cyanoborohydride (25895-60-7) → 2-(1-(2,4-dichlorophenyl)-1H-pyrazole-4-yl)acetonitrile

Conditions	Yield
Stage #1: sodium cyanoborohydride In dimethyl sulfoxide at 80℃; for 0.5h; Stage #2: 4-(chloromethyl)-1-(2,4-dichlorophenyl)-1H-pyrazole In dimethyl sulfoxide; N,N-dimethyl-formamide	94.9%

C12H34B2N3(1+)*Br(1-) + sodium cyanoborohydride (25895-60-7) → C12H34B2N3(1+)*CH3BN(1-)

Conditions	Yield
In acetonitrile at 20℃; for 18h;	88.9%

C5H18BN2(1+)*Cl(1-) + sodium cyanoborohydride (25895-60-7) → C5H18BN2(1+)*CH3BN(1-)

Conditions	Yield
In acetonitrile at 20℃; for 24h;	87.9%

(R)-3-N-Cyclopentylamino-8-fluoro-5-methoxy-3,4-dihydro-2H-1-benzopyran + sodium cyanoborohydride (25895-60-7) + propionaldehyde (123-38-6) → (R)-3-(N-Cyclopentyl-N-n-propylamino)-8-fluoro-5-methoxy-3,4-dihydro-2H-1-benzopyran (169758-89-8)

Conditions	Yield
With ammonia; acetic acid In methanol; ethyl acetate	65%
With ammonia; acetic acid In methanol; ethyl acetate	65%

tert-butyl [3-(2-amino-5-chlorophenoxy)benzyl]carbamate + sodium cyanoborohydride (25895-60-7) + 4-Phenylbenzaldehyde (3218-36-8) → tert-butyl [3-[2-(4-biphenylmethylamino)phenoxy]benzyl] carbamate

Conditions	Yield
With acetic acid In methanol	87.4%

sodium cyanoborohydride (25895-60-7) + 1-[(4-cyano-5-methyl-4-phenyl)hexyl]-4-[2-(4-aminophenoxy)ethyl]piperazine (255847-14-4) → 1-[(4-cyano-5-methyl-4-phenyl)hexyl]-4-[2-(4-dimethylaminophenoxy)ethyl]piperazine

Conditions	Yield
With formaldehyd; sodium hydrogencarbonate In acetic acid; acetonitrile	81%

[(1-Ethoxycyclopropyl)oxy]trimethylsilane (27374-25-0) + 1-(4-fluorophenyl)-6-(piperidin-4-yloxy)-3,4-dihydroquinolin-2(1H)-one hydrochloride (1239768-76-3) + sodium cyanoborohydride (25895-60-7) → 6-[(1-cyclopropylpiperidin-4-yl)oxy]-1-(4-fluorophenyl)-3,4-dihydroquinolin-2(1H)-one (1239768-52-5)

Conditions	Yield
Stage #1: [(1-Ethoxycyclopropyl)oxy]trimethylsilane; 1-(4-fluorophenyl)-6-(piperidin-4-yloxy)-3,4-dihydroquinolin-2(1H)-one hydrochloride With acetic acid; triethylamine In methanol at 20℃; for 1h; Molecular sieve 3Å; Stage #2: sodium cyanoborohydride In methanol at 20 - 95℃;	37%

Upstream product

• 16940-66-2 sodium tetrahydroborate 
• 74-90-8 hydrogen cyanide 
• 592-04-1 mercury(II) cyanide 
• 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 

Downstream Products

• 82176-64-5 (Z)-4-Dimethylamino-3-phenyl-but-3-enenitrile 
• 82176-65-6 (Z)-3-(4-Chloro-phenyl)-4-dimethylamino-but-3-enenitrile 
• 82176-66-7 (Z)-4-Dimethylamino-3-(4-methoxy-phenyl)-but-3-enenitrile 
• 70700-36-6 N,N-Dimethyl-β-methylen-4-nitro-phenylethane amine 
• 82176-67-8 3-cyano-2-(p-nitrophenyl)-1-N,N-dimethylamino-1-propene 
• 96530-52-8 C₄₀H₄₄N₂O₉ 
• 90593-18-3 2-O-benzyl-4,6-O-benzylidene-α-D-altropyranosyl 2-O-benzyl-4,6-O-benzylidene-α-D-altropyranoside 
• 325796-79-0 1-Benzyl-3-(5-methoxypyridin-2-ylmethyl)-2,3-dihydro-1H-indol 
• 688321-38-2 N,N-diethyl 3,6-dideoxy-3,6-imino-N'-benzyl-4,5-O-isopropylidene-7-O-trityl-L-glycero-D-manno-heptonamide 

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