Sodium triacetoxyborohydride

HCID 5049666CAS 56553-60-7
Substructure searchFind similar structures

Basic information

Standard SMILES
CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
InChIKey
HHYFEYBWNZJVFQ-UHFFFAOYSA-N
Molecular formula
C6H10BNaO6
Average molar mass
211.94 g/mol
Monoisotopic mass
212.0468125

Names & identifiers

Preferred name
Sodium triacetoxyborohydride
IUPAC
sodium triacetyloxyboranuide
English name
Sodium triacetoxyborohydride
Molecular formula
C6H10BNaO6
Molecular weight
211.94

Names & synonyms

4VU0JE4YSKDTXSID8074368Borate(1-), tris(acetato-kappaO)hydro-, sodium (1:1), (T-4)-RefChem:887964DTXCID5042089611-401-056553-60-7Borate(1-), tris(acetato-kappaO)hydro-, sodium, (T-4)-Sodium triacetoxyborohydrideSodium Triacetoxyborohydride (Technical Grade)C6H10BNaO6sodium trisacetoxyborohydride
Show more names
stabNaBH（OAc）3sodium tris(acetoxy)borohydrideSODIUM TRIACETOXYHYDROBORATESodium TriacetoxyborohyrideSodium triacetoborohydridesodium bis(acetyloxy)boranuidyl acetateSodium triacetoxySodium triacetoboroSodium triacetoboroh
sodium triacetoxy-borohydrideNa(OAc)3BHNaB(OAc)3HNaBH(AcO)3NaBH(OAc)3sodium tnacetoxyborohydndesodium;triacetoxyboranuideUNII-4VU0JE4YSK

Database identifiers

CAS
56553-60-7
PubChem CID
5049666
DTXSID
DTXSID8074368
UNII
4VU0JE4YSK
EC Number
435-580-8、611-401-0
Nikkaji
J1.884.353F、J2.805.651F

Properties

Computed structural properties

Topological polar surface area
78.9 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
7
Rotatable bonds
6
Heavy atoms
14

Experimental & physicochemical properties

Physical DescriptionWhite crystalline powder; [Alfa Aesar MSDS]

Physicochemical properties

Melting point
116 · 116-120 °C (dec.) (lit.)
Boiling point
111.1 ℃[at · 111.1℃[at 101 325 Pa]
Density
1.36 · 1.36[at 20℃]
vapor pressure
0 Pa · 0Pa at 25℃
storage temp.
Inert atmosphere,Room Temperature
solubility
Soluble in dimethyl sulfoxide, methanol, benzene, toluene, terahydrofuran, dioxane and methylene chloride.

Safety & regulation

GHS classification

GHS Classification · 5 items

Danger

H228 (38.3%): Flammable solid [Danger Flammable solids]；H260 (68.9%): In contact with water releases flammable gases which may ignite spontaneously [Danger Substances and mixtures which in contact with water, emit flammable gases]；H261 (31.1%): In contact with water releases flammable gas [Danger Substances and mixtures which in contact with water, emit flammable gases]；H314 (11.1%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]；H315 (83%): Causes skin irritation [Warning Skin corrosion/irritation]；H318 (65.1%): Causes serious eye damage [Danger Serious eye damage/eye irritation]；H335 (26%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]；H360 (50.2%): May damage fertility or the unborn child [Danger Reproductive toxicity]

P203, P210, P223, P231+P232, P240, P241, P260, P261, P264, P264+P265, P271, P280, P301+P330+P331, P302+P335+P334, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P318, P319, P321, P332+P317, P362+P364, P363, P370+P378, P402+P404, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 235 reports by companies from 20 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

Status: Active Update: 22-02-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/20512；Status: Active Update: 11-11-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/17743

Borate(1-), tris(acetato-.kappa.O)hydro-, sodium, (T-4)-: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryReacts with water evolving flammable gases; An irritant that may cause serious eye injury; [Alfa Aesar MSDS] See Lithium borohydride and Sodium borohydride. See Boric acid.
Hazard Classes and CategoriesFlam. Sol. 2 (38.3%)；Water-react. 1 (68.9%)；Water-react. 3 (31.1%)；Skin Corr. 1B (11.1%)；Skin Irrit. 2 (83%)；Eye Dam. 1 (65.1%)；STOT SE 3 (26%)；Repr. 1B (50.2%)

Regulatory information

Regulatory Information · 2 items

Status: Active Update: 22-02-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/20512；Status: Active Update: 11-11-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/17743

Borate(1-), tris(acetato-.kappa.O)hydro-, sodium, (T-4)-: Does not have an individual approval but may be used under an appropriate group standard

Safety data

F
10-21
wgk
3
tsca
TSCA listed
ridadr
UN 1409 4.3/PG 2
hs_code
29319090
risk_code
15-34-14/15-37/38-11

Chemistry & industry

Uses & manufacturing

UsesUsed as a selective reducing agent in organic synthesis; [Merck Index]
Applications · 2 items

DescriptionSodium triacetoxyborohydride, also known as sodium triacetoxyhydroborate, commonly abbreviated STAB, is a white hygroscopic solid that emits hydrogen gas when hydrolysed in water, which is flammable. STAB is a milder reducing agent than sodium borohydride or even sodium cyanoborohydride. Even sodium cyanoborohydride is a milder reducing agent than sodium borohydride, and is particularly suitable for the reductive amination of aldehydes and ketones. It can reduce aldehydes but not most ketones. It can also be used in the reductive alkylation of secondary amines in aldehyde-bisulfite adducts.

UsesSodium Triacetoxyborohydride(STAB) is a hydride reagent used in stereoselective reductive amination. It is able to replace toxic sodium cyanoborohydride under most conditions. It is selective in reducing aldehydes to alcohols in the presence of ketones. STAB is also stable in anhydrous acids, which enables reductive amination of aldehydes and ketones. It used in reductive amination of ketones and aldehydes and reductive amination/lactamization of carbonyl compounds with amines. The advantage of STAB compared to sodium cyanoborohydride is evident. STAB, being non-toxic, is easier to handle and forms no toxic by-products, making the treatment of process waste after the reaction simple and less costly.

Upstream & downstream products

Suppliers50 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖北瑞泰医药科技有限公司15335880183
北京阿克曼科技有限公司18001219251

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