Sodium triacetoxyborohydride supplier

Name
Sodium triacetoxyborohydride
EINECS 411-950-4
CAS No. 56553-60-7
Article Data22
CAS DataBase
Density 1.36[at 20℃]
Solubility reacts with water
Melting Point 116-120 °C (dec.)(lit.)
Formula C₆H₁₀BNaO₆
Boiling Point 111.1℃[at 101 325 Pa]
Molecular Weight 211.943
Flash Point
Transport Information UN 1409 4.3/PG 2
Appearance white crystalline powder
Safety 43-7/8-45-36/37/39-26
Risk Codes 15-34-14/15
Molecular Structure
Hazard Symbols F, Xi, C
Synonyms Sodium Triacetoxyborohydride (STAB);Sodium triacetoxyborohyride;Sodium triacetoborohydride;Sodium Triacetoxysborobydride;
PSA 78.90000
LogP -0.60710

Synthetic route

: 16940-66-2
sodium tetrahydroborate

: 56553-60-7
sodium tris(acetoxy)borohydride

Conditions

Conditions	Yield
With acetic acid In benzene byproducts: H2; under N2-atmosphere; slurry of NaBH4 in benzene cooled (10°C); CH3COOH added dropwise (temp. < 20°C); mixt. warmed (ambient temp.) and stirred for 8h;; filtration; white powder washed (ether) and held under vacuum over night; elem. anal.;;	92%

: 64-19-7
acetic acid

: 56553-60-7
sodium tris(acetoxy)borohydride

Conditions

Conditions	Yield
With sodium tetrahydroborate In benzene
With sodium tetrahydroborate at 15 - 20℃;
With sodium tetrahydroborate In 2-methylpropyl acetate at 0 - 5℃; for 1h;
With sodium tetrahydroborate In dichloromethane for 2h;
With sodium tetrahydroborate In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Schlenk technique;

: sodium triacetoxyborohydride

: 64-19-7
acetic acid

: 56553-60-7
sodium tris(acetoxy)borohydride

: 4887-24-5
triacetoxyborane

: 7646-69-7
sodium hydride

A: sodium triacetoxyborohydride

B: 56553-60-7
sodium tris(acetoxy)borohydride

Conditions

Conditions	Yield
In 1,4-dioxane addn. of soln. of tris(acetoxy)borane in dry dioxane to suspension of NaH in dry dioxane; refluxing of mixt. for 4 h; Na(HB(OCOCH3)3) and small amts. of Na(H2B(OCOCH3)2) obtained;
In 1,4-dioxane boiling the mixture 4 hours long;
In 1,4-dioxane on boiling, pptn. of NaBH(OCOCH3)3, small amounts of NaBH2(OCOCH3)2 in the filtrate;;

...Expand

: 16940-66-2
sodium tetrahydroborate

: 64-19-7
acetic acid

: 56553-60-7
sodium tris(acetoxy)borohydride

Conditions

Conditions	Yield
In N,N-dimethyl acetamide Kinetics; byproducts: H2; NaBH4 charged into an acetic acid/N,N-dimethylacetamide soln. at -10°C, warmed to 22°C, aged; the process studied in a calorimeterto evaluate thermal hazards;
refluxing Na with glacial acetic acid in ratio of 4:3.25 equivalents for 15 min. under N2;
refluxing Na with glacial acetic acid in ratio of 4:3.25 equivalents for 15 min. under N2;

: trifluoromethanesulfonate 2-cyano-1,1,4-trimethyl-3-phenyl-azetidinium

: 56553-60-7
sodium tris(acetoxy)borohydride

: C15H20N2O2

Conditions

Conditions	Yield
In tetrahydrofuran for 24h; Heating;	100%

: 5824-40-8
Triphenylmethylamin

: 56553-60-7
sodium tris(acetoxy)borohydride

: 7370-34-5
N-triphenylmethyl-N-ethylamine

Conditions

Conditions	Yield
In acetonitrile at 60℃; for 15h;	99.9%

: 39742-60-4
1-(2-phenylethyl)-4-piperidinone

: 2038-57-5
3-Phenylpropan-1-amine

: 56553-60-7
sodium tris(acetoxy)borohydride

: 1-(2-phenylethyl)-4-[N-(3-phenylpropyl)]-aminopiperidine

Conditions

Conditions	Yield
In dichloromethane; acetic acid at 25℃; for 20h;	99%

...Expand

: 12093-10-6
ferrocenecarboxaldehyde

: 506-59-2
N,N-dimethylammonium chloride

: 56553-60-7
sodium tris(acetoxy)borohydride

: 1271-86-9
N,N-dimethylaminomethylferrocene

Conditions

Conditions	Yield
With triethylamine In dichloromethane Fe complex reacted with HNMe2*HCl and B compd. in presence of Et3N in CH2Cl2;	99%

...Expand

: 3-methoxyazetidine hydrochloride

: 19099-93-5
benzyl 4-oxo-1-piperidinecarboxylate

: 56553-60-7
sodium tris(acetoxy)borohydride

: C17H24N2O3

Conditions

Conditions	Yield
Stage #1: 3-methoxyazetidine hydrochloride; benzyl 4-oxo-1-piperidinecarboxylate With acetic acid In tetrahydrofuran at 20℃; for 0.666667h; Stage #2: sodium tris(acetoxy)borohydride In tetrahydrofuran at 0 - 20℃;	99%

...Expand

: 2,5-Dichloro-4-nitrophenylacetaldehyde

: 56553-60-7
sodium tris(acetoxy)borohydride

: 2,5-Dichloro-4-(2-[4-(t-butoxycarbonyl)-1-piperazinyl]ethyl)-nitrobenzene

Conditions

Conditions	Yield
With acetic acid In 1-t-Butoxycarbonylpiperazine	98%

: tris[(2-(benzyloxy)-3-(3',5'-bis(trifluoromethyl)phenyl)-5-methyl)benzyl]amine

: 56553-60-7
sodium tris(acetoxy)borohydride

A: C48H33F18NO3

B: C48H30BF18NO3

Conditions

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In ethyl acetate at 20℃; under 5171.62 Torr; for 24h;	A 98% B n/a

...Expand

: 50-00-0
formaldehyd

: 921751-98-6
benzyl (R)-[5-oxo-1-(2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)pyrrolidin-3-yl]carbamate

: 56553-60-7
sodium tris(acetoxy)borohydride

: 921751-99-7
benzyl (R)-[1-(3-methyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)-5-oxopyrrolidin-3-yl]carbamate

Conditions

Conditions	Yield
Stage #1: formaldehyd; benzyl (R)-[5-oxo-1-(2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yl)pyrrolidin-3-yl]carbamate With acetic acid In methanol; water at 20℃; for 0.5h; pH=6; Michael Condensation; Stage #2: sodium tris(acetoxy)borohydride In methanol; water for 1h;	96%

...Expand

: (R)-benzyl 3-(1-aminoethyl)azetidine-1-carboxylate

: 56553-60-7
sodium tris(acetoxy)borohydride

: 613-45-6
2,4-Dimethoxybenzaldehyde

: (R)-benzyl 3-(1-((2,4-dimethoxybenzyl)amino)ethyl)azetidine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: (R)-benzyl 3-(1-aminoethyl)azetidine-1-carboxylate; 2,4-Dimethoxybenzaldehyde With acetic acid In 1,2-dichloro-ethane at 30℃; for 1h; Stage #2: sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 2h;	95.1%

...Expand

: 943025-57-8
(4R/S)-3-chloro-4-({4-amino-1-piperidinyl}methyl)-4-hydroxy-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one

: 56553-60-7
sodium tris(acetoxy)borohydride

: (4R/S)-3-chloro-4-hydroxy-4-[(4-{[(3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazin-6-yl)methyl]amino}-1-piperidinyl)methyl]-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one monoacetate salt

Conditions

Conditions	Yield
Stage #1: 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carbaldehyde; (4R/S)-4-[(4-amino-1-piperidinyl)methyl]-3-chloro-4-hydroxy-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one In methanol; chloroform at 20℃; for 2h; Stage #2: sodium tris(acetoxy)borohydride In methanol; chloroform for 2h;	95%

: 943025-57-8
(4R/S)-3-chloro-4-({4-amino-1-piperidinyl}methyl)-4-hydroxy-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one

: 56553-60-7
sodium tris(acetoxy)borohydride

: (4R/S)-3-chloro-4-hydroxy-4-({4-[([1,3]oxathiolo[5,4-c]pyridin-6-ylmethyl)amino]-1-piperidinyl}methyl)-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one monoacetate salt

Conditions

Conditions	Yield
Stage #1: (4R/S)-4-[(4-amino-1-piperidinyl)methyl]-3-chloro-4-hydroxy-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one; [1,3]oxathiolo[5,4-c]pyridine-6-carbaldehyde In methanol; chloroform at 20℃; for 2h; Stage #2: sodium tris(acetoxy)borohydride In methanol; chloroform for 2h;	95%

: 759-22-8
N,N-diisopropylacetamide

: 5-methylsulfonylisoindoline hydrochloride

: 56553-60-7
sodium tris(acetoxy)borohydride

: tert-butyl (2R,3S,5R)-5-(5-methylsulfonylisoindolin-2-yl)-2-(2,5-difluorophenyl)tetrahydro-2H-pyran-3-ylcarbamate

Conditions

Conditions	Yield
With acetic acid	95%

...Expand

: 56553-60-7
sodium tris(acetoxy)borohydride

: 124-30-1
1-aminooctadecane

: 30427-51-1
diethyl-octadecyl-amine

Conditions

Conditions	Yield
In acetonitrile at 60℃; for 15h;	94.6%

: 1329422-57-2
N-methyliminodiacetyl (1-(4-fluorophenyl)-2-oxoethyl)boronate

: 56553-60-7
sodium tris(acetoxy)borohydride

: C13H15BFNO5

Conditions

Conditions	Yield
Stage #1: N-methyliminodiacetyl (1-(4-fluorophenyl)-2-oxoethyl)boronate With acetic acid In 1,2-dichloro-ethane for 0.166667h; Cooling with ice; Stage #2: sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane for 5h; Cooling with ice;	94%

: 12093-10-6
ferrocenecarboxaldehyde

: 56553-60-7
sodium tris(acetoxy)borohydride

: 103-67-3
benzyl-methyl-amine

: N-benzyl-N-(ferrocenylmethyl)methylamine*0.1H2CO3

Conditions

Conditions	Yield
With sodium hydroxide In dichloromethane PhNHMe added to stirred soln. of Fe complex in CH2Cl2; B compd. added portionwise; stirred for 4 h; poured onto ice; adjusted to pH 12 (NaOH); extd. with Et2O; dried (Na2SO4); solvent evapd.; chromd. (SiO2, CHCl3-MeOH); elem. anal.;	92%

...Expand

: 918342-45-7
1-phenyl-3-ferrocenyl-1H-pyrazole-4-carbaldehyde

: 56553-60-7
sodium tris(acetoxy)borohydride

: 918342-51-5
(C5H5)Fe(C5H4C3H(CH2OH)N2C6H5)

Conditions

Conditions	Yield
With diisopropylamine In 1,2-dichloro-ethane soln. Fe complex and amine in 1,2-dichloroethane was stirred at room temp. for 1 h, NaBH(OAc)3 was added and refluxed for 30 min; react. mixt. was treated with aq. NaHCO3, extd. with CH2Cl2, washed withbrine and dried over Na2SO4, solvent was removed, residue was chromd. o n silica (CHCl3-MeOH 9:1); elem. anal.;	92%

: 50-00-0
formaldehyd

: (S)-2-(tert-butoxy)-2-(6-(((cyclohexylmethyl)amino)methyl)-4-(4,4-dimethylpiperidin-1-yl)-5-(4-(4-fluorophenethoxy)phenyl)-2-methylpyridin-3-yl)acetic acid

: 56553-60-7
sodium tris(acetoxy)borohydride

: (S)-2-(tert-butoxy)-2-(6-(((cyclohexylmethyl)(methyl)amino)methyl)-4-(4,4-dimethylpiperidin-1-yl)-5-(4-(4-fluorophenethoxy)phenyl)-2-methylpyridin-3-yl)acetic acid

Conditions

Conditions	Yield
Stage #1: formaldehyd; (S)-2-(tert-butoxy)-2-(6-(((cyclohexylmethyl)amino)methyl)-4-(4,4-dimethylpiperidin-1-yl)-5-(4-(4-fluorophenethoxy)phenyl)-2-methylpyridin-3-yl)acetic acid In methanol; water at 20℃; for 2h; Stage #2: sodium tris(acetoxy)borohydride In methanol; water for 3h;	92%

...Expand

: 12093-10-6
ferrocenecarboxaldehyde

: 18598-74-8
methyl L-isoleucinate hydrochloride

: 56553-60-7
sodium tris(acetoxy)borohydride

: N-(ferrocenylmethyl)-L-isoleucine methyl ester

Conditions

Conditions	Yield
With sodium hydroxide; triethylamine In tetrahydrofuran isoleucine methyl ester and Et3N added to stirred soln. of Fe complex inTHF; B compd. added portionwise; stirred for 4 h; poured onto ice; adju sted to pH 12 (NaOH); extd. with Et2O; dried (Na2SO4); solvent evapd.; chromd. (SiO2, CHCl3-MeOH); elem. anal.;	91.8%

...Expand

: 1367074-76-7
(3S,4S)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-(2-oxoethoxy)pyrrolidine-1-carboxylate

: 56553-60-7
sodium tris(acetoxy)borohydride

: 89-99-6
2-fluorobenzylamine

: 1367074-77-8
(3S,4S)-tert-butyl 3-((6-(bis(tert-butoxycarbonyl)amino)-4-methylpyridin-2-yl)methyl)-4-(2-(2-fluorobenzylamino)ethoxy)pyrrolidine-1-carboxylate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 3h;	91%

...Expand

: 56553-60-7
sodium tris(acetoxy)borohydride

: 162536-42-7
(1S,2R)-(3-amino-1-benzyl-2-hydroxy-propyl)-carbamic acid tert butyl ester

: 288295-69-2
tert-Butyl N-(1S,2R)-1-benzyl-3-[(4-cyano-2,2-dimethylbutyl)amino]-2-hydroxypropylcarbamate

Conditions

Conditions	Yield
In tetrahydrofuran; 1,2-dichloro-ethane; N,N-dimethyl-formamide	90%

: 918342-45-7
1-phenyl-3-ferrocenyl-1H-pyrazole-4-carbaldehyde

: 56553-60-7
sodium tris(acetoxy)borohydride

: 616-34-2
methoxycarbonylmethylamine

: 1259930-83-0
methyl 2-[(1-phenyl-3-ferrocenyl-1-pyrazol-4-yl)methyl-amino]acetate

Conditions

Conditions	Yield
In 1,2-dichloro-ethane soln. Fe complex and amine in 1,2-dichloroethane was stirred at room temp. for 1 h, NaBH(OAc)3 was added and refluxed for 30 min; react. mixt. was treated with aq. NaHCO3, extd. with CH2Cl2, washed withbrine and dried over Na2SO4, solvent was removed, residue was chromd. o n silica (CHCl3-MeOH 9:1); elem. anal.;	90%

...Expand

: 1259930-40-9
3-ferrocenyl-1-(2-naphthyl)pyrazole-4-carbaldehyde

: 56553-60-7
sodium tris(acetoxy)borohydride

: 1259930-45-4
(C5H5)Fe(C5H4C3H(CH2OH)N2C10H7)

Conditions

Conditions	Yield
With diisopropylamine In 1,2-dichloro-ethane soln. Fe complex and amine in 1,2-dichloroethane was stirred at room temp. for 1 h, NaBH(OAc)3 was added and refluxed for 30 min; react. mixt. was treated with aq. NaHCO3, extd. with CH2Cl2, washed withbrine and dried over Na2SO4, solvent was removed, residue was chromd. o n silica (CHCl3-MeOH 9:1); elem. anal.;	90%

: 696-41-3
m-iodobenzaldehyde

: 56553-60-7
sodium tris(acetoxy)borohydride

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 141189-59-5
(3-iodo-benzyl)-dimethyl-amine

Conditions

Conditions	Yield
Stage #1: m-iodobenzaldehyde; N,N-dimethyl-formamide With acetic acid In dichloromethane at 0℃; Stage #2: sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 0.5h;	90%

...Expand

: 527681-61-4
3,4-dihydro-2H-pyrano[2,3-c]pyridine-6-carbaldehyde

: 56553-60-7
sodium tris(acetoxy)borohydride

: (4R/S)-3-chloro-4-({4-[(3,4-dihydro-2H-pyrano[2,3-c]pyridin-6-ylmethyl)amino]-1-piperidinyl}methyl)-4-hydroxy-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one monoacetate salt

Conditions

Conditions	Yield
Stage #1: (4R/S)-4-[(4-amino-1-piperidinyl)methyl]-3-chloro-4-hydroxy-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one; 3,4-dihydro-2H-pyrano[2,3-c]pyridine-6-carbaldehyde In methanol; chloroform at 20℃; for 2h; Stage #2: sodium tris(acetoxy)borohydride In methanol; chloroform for 2h;	88%

: 56553-60-7
sodium tris(acetoxy)borohydride

: 64-04-0
phenethylamine

A: 877-95-2
methyl-N-(benzyl-methyl)-formamide

B: 5300-21-0
N,N-diethylphenethylamine

Conditions

Conditions	Yield
In acetonitrile at 60℃; for 15h;	A 6.5% B 86.2%

...Expand

: 913983-80-9
1-bromo-2-methylallylamine

: Fe(CO)3(CH3CHCHCHCHCO(CH2)3CHO)

: 56553-60-7
sodium tris(acetoxy)borohydride

: E-Fe(CO)3(CH3CHCHCHCHC5H9N(CH2C(CH3)CHBr))

Conditions

Conditions	Yield
In tetrahydrofuran treatment of iron compd. with amine deriv. and boron compd. in THF; NMR;	86%

...Expand

: 110-89-4
piperidine

: 867066-17-9
N-(2-naphthylsulfonyl)-N'-(2-acetamido)piperazine

: 56553-60-7
sodium tris(acetoxy)borohydride

: N-(2-naphthylsulfonyl)-N'-(2-thioacetamido)piperazine

Conditions

Conditions	Yield
With sodium hydrogencarbonate In methanol; dichloromethane	85%

...Expand

: 56553-60-7
sodium tris(acetoxy)borohydride

: 7440-44-0
pyrographite

: 210891-12-6
N-(4,5-Dimethyl-3-isoxazolyl)-2'-formyl-4'-(2-oxazolyl)[1,1'-biphenyl]-2-sulfonamide

: 415697-66-4
N-(4,5-Dimethyl-3-isoxazolyl)-2'-[(methylamino)methyl]-4'-(2-oxazolyl)[1,1'-biphenyl]-2-sulfonamide, monohydrochloride

Conditions

Conditions	Yield
With hydrogenchloride; methylamine In methanol; ethanol; acetic acid	85%

...Expand

Sodium triacetoxyborohydride Chemical Properties

Molecular Structure of Sodium triacetoxyborohydride (CAS NO.56553-60-7):

IUPAC Name: sodium triacetyloxyboranuide
Empirical Formula: C₆H₁₀BNaO₆
Molecular Weight: 211.9408
CAS Registry Number: 56553-60-7
H bond acceptors: 6
H bond donors: 0
Freely Rotating Bonds: 6
Polar Surface Area: 78.9 Å²
Melting point: 116-120 °C (dec.)(lit.)
Storage Temp: Flammables + water-Freezer (-20°C)e area
Water Solubility: Reacts
Sensitive: Moisture Sensitive
Chemical Stability: Stable under normal temperatures and pressures. Moisture sensitive.
Conditions to Avoid: High temperatures, incompatible materials, dust generation, exposure to moist air or water.
Incompatibilities with Other Materials Strong oxidizing agents, acids, alcohols.
InChI
InChI=1/C6H10BO6.Na/c1-4(8)11-7(12-5(2)9)13-6(3)10;/h7H,1-3H3;/q-1;+1
Smiles
[Na+].CC(=O)O[BH-](OC(C)=O)OC(C)=O
Product Categories: Boron compounds; 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; organic intermediates

Sodium triacetoxyborohydride Safety Profile

Hazard Codes: F, Irritant Xi, Corrosive C
Risk Statements: 15-34-14/15
R15:Contact with water liberates extremely flammable gases
R34:Causes burns
R14/15:Reacts violently with water, liberating extremely flammable gases
Safety Statements: 43-7/8-45-36/37/39-26
S43:In case of fire, use ... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add - Never use water)
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
S7/8:Keep container tightly closed and dry
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection
RIDADR: UN 1409 4.3/PG 2
WGK Germany: 3
Hazard Note: Irritant/Flammable
HazardClass: 4.3
PackingGroup: III

Sodium triacetoxyborohydride Specification

Sodium triacetoxyborohydride , with CAS number of 56553-60-7, can be called Sodium Triacetoxyborohydride (STAB) ; Sodium triacetoxy borohydride ; Sodium triacetoxyborohydride(STAB)Triacetoxyborohydride sodium salt ; Sodium triacetoxyborohyride ; Sodium triacetoborohydride ; Sodium Triacetoxysborobydride ; SATBSodium Triacetoxyborohydride ; Sodium triacetoxyborohydride 99% ; Sodium triacetoxyborohydride(STAB) . It is a white powder.

Product Name

Sodium triacetoxyborohydride

Synthetic route

Sodium triacetoxyborohydride Chemical Properties

Sodium triacetoxyborohydride Safety Profile

Sodium triacetoxyborohydride Specification

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