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Part I: Carbon
- I.1: Carbon-Carbon Bonds
- I.1.1 Alkanes
- Primary carbon
- Secondary carbon
- Tertiary carbon
- Quaternary carbon
- I.1.2 C-C double and Triple Bonds
- Alkene
- Alkyne
- Allene
- I.2: One Carbon-Hetero Bond
- I.2.1 Alkyl Halogenides
- Alkylchloride
- Alkylfluoride
- Alkylbromide
- Alkyliodide
- I.2.2 Alcohols and Ethers
- Alcohol
- Primary alcohol
- Secondary alcohol
- Tertiary alcohol
- Dialkylether
- Dialkylthioether
- Alkylarylether
- Diarylether
- Alkylarylthioether
- Diarylthioether
- Oxonium
- I.2.3 Amines
- Amine
- Primary aliphatic amine
- Secondary aliphatic amine
- Tertiary aliphatic amine
- Quaternary aliphatic ammonium
- Primary aromatic amine
- Secondary aromatic amine
- Tertiary aromatic amine
- Quaternary aromatic ammonium
- Secondary mixed amine
- Tertiary mixed amine
- Quaternary mixed ammonium
- Ammonium
- I.2.4 Others
- Alkylthiol
- Dialkylthioether
- Alkylarylthioether
- Disulfide
- 1,2-Aminoalcohol
- 1,2-Diol
- 1,1-Diol
- Hydroperoxide
- Peroxo
- Organolithium compounds
- Organomagnesium compounds
- Organometallic compounds
- I.3: Two Carbon-Hetero Bonds (Carbonyl and Derivatives)
- I.3.1 Double Bond to Hetero
- Aldehyde
- Ketone
- Thioaldehyde
- Thioketone
- Imine
- Immonium
- Oxime
- Oximether
- I.3.2. Two Single Bonds to Hetero
- Acetal
- Hemiacetal
- Aminal
- Hemiaminal
- Thioacetal
- Thiohemiacetal
- Halogen acetal like
- Acetal like
- Halogenmethylen ester and similar
- NOS methylen ester and similar
- Hetero methylen ester and similar
- Cyanhydrine
- I.3.3 Single Bond to Hetero, C=C Double Bond (Enols and Similar)
- Chloroalkene
- Fluoroalkene
- Bromoalkene
- Iodoalkene
- Enol
- Endiol
- Enolether
- Enolester
- Enamine
- Thioenol
- Thioenolether
- I.4: Three Carbon-Hetero Bonds (Carboxyl and Derivatives)
- Acylchloride
- Acylfluoride
- Acylbromide
- Acyliodide
- Acylhalide
- Carboxylic acid
- Carboxylic ester
- Lactone
- Carboxylic anhydride
- Carboxylic acid derivative
- Carbothioic acid
- Carbothioic S ester
- Carbothioic S lactone
- Carbothioic O ester
- Carbothioic O lactone
- Carbothioic halide
- Carbodithioic acid
- Carbodithioic ester
- Carbodithiolactone
- Amide
- Primary amide
- Secondary amide
- Tertiary amide
- Lactam
- Alkyl imide
- N hetero imide
- Imide acidic
- Thioamide
- Thiolactam
- Oximester
- Amidine
- Hydroxamic acid
- Hydroxamic acid ester
- Imidoacid
- Imidoacid cyclic
- Imidoester
- Imidolactone
- Imidothioacid
- Imidothioacid cyclic
- Imidothioester
- Imidothiolactone
- Amidine
- Imidolactam
- Imidoylhalide
- Imidoylhalide cyclic
- Amidrazone
- Alpha aminoacid
- Alpha hydroxyacid
- Peptide middle
- Peptide C term
- Peptide N term
- Carboxylic orthoester
- Ketene
- Ketenacetal
- Nitrile
- Isonitrile
- Vinylogous carbonyl or carboxyl derivative
- Vinylogous acid
- Vinylogous ester
- Vinylogous amide
- Vinylogous halide
- I.5: Four Carbon-Hetero Bonds (Carbonic Acid and Derivatives)
- Carbonic acid dieester
- Carbonic acid esterhalide
- Carbonic acid monoester
- Carbonic acid derivatives
- Thiocarbonic acid dieester
- Thiocarbonic acid esterhalide
- Thiocarbonic acid monoester
- Urea
- Thiourea
- Isourea
- Isothiourea
- Guanidine
- Carbaminic acid
- Urethan(Carbamate ester)
- Biuret
- Semicarbazide
- Carbazide
- Semicarbazone
- Carbazone
- Thiosemicarbazide
- Thiocarbazide
- Thiosemicarbazone
- Thiocarbazone
- Isocyanate
- Cyanate
- Isothiocyanate
- Thiocyanate
- Carbodiimide
- Orthocarbonic derivatives
- I.6 Aromatics
- Phenol
- 1,2-Diphenol
- Arylchloride
- Arylfluoride
- Arylbromide
- Aryliodide
- Arylthiol
- Iminoarene
- Oxoarene
- Thioarene
- Hetero N basic H
- Hetero N basic no H
- Hetero N nonbasic
- Hetero O
- Hetero S
- Heteroaromatic
Part II: N, S, P, Si, B
- II.1 Nitrogen
- Nitrite
- Thionitrite
- Nitrate
- Nitro
- Nitroso
- Azide
- Acylazide
- Diazo
- Diazonium
- Nitrosamine
- Nitrosamide
- N-Oxide
- Hydrazine
- Hydrazone
- Hydroxylamine
- II.2 Sulfur
- Sulfon
- Sulfoxide
- Sulfonium
- Sulfuric acid
- Sulfuric monoester
- Sulfuric diester
- Sulfuric monoamide
- Sulfuric diamide
- Sulfuric esteramide
- Sulfuric derivative
- Sulfonic acid
- Sulfonamide
- Sulfonic ester
- Sulfonic halide
- Sulfonic derivative
- Sulfinic acid
- Sulfinic amide
- Sulfinic ester
- Sulfinic halide
- Sulfinic derivative
- Sulfenic acid
- Sulfenic amide
- Sulfenic ester
- Sulfenic halide
- Sulfenic derivative
- II.3 Phosphorous
- Phosphine
- Phosphine oxide
- Phosphonium
- Phosphorylen
- Phosphonic acid
- Phosphonic monoester
- Phosphonic diester
- Phosphonic monoamide
- Phosphonic diamide
- Phosphonic esteramide
- Phosphonic acid derivative
- Phosphoric acid
- Phosphoric monoester
- Phosphoric diester
- Phosphoric triester
- Phosphoric monoamide
- Phosphoric diamide
- Phosphoric triamide
- Phosphoric monoestermonoamide
- Phosphoric diestermonoamide
- Phosphoric monoesterdiamide
- Phosphoric acid derivative
- Phosphinic acid
- Phosphinic ester
- Phosphinic amide
- Phosphinic acid derivative
- Phosphonous acid
- Phosphonous monoester
- Phosphonous diester
- Phosphonous monoamide
- Phosphonous diamide
- Phosphonous esteramide
- Phosphonous derivatives
- Phosphinous acid
- Phosphinous ester
- Phosphinous amide
- Phosphinous derivatives
- II.4 Silicon
- Quart silane
- Non-quart silane
- Silylmonohalide
- Het trialkylsilane
- Dihet dialkylsilane
- Trihet alkylsilane
- Silicic acid derivative
- II.5 Boron
- Trialkylborane
- Boric acid derivatives
- Boronic acid derivative
- Borohydride
- Quaternary boron
Part III: Some Special Patterns
- III.1 Chains
- III.2 Rings
- Aromatic
- Heterocyclic
- Epoxide
- NH aziridine
- Spiro
- Annelated rings
- Bridged rings
- III.3 Sugars and Nucleosides/Nucleotides, Steroids
- Sugar pattern 1
- Sugar pattern 2
- Sugar pattern combi
- Sugar pattern 2 reducing
- Sugar pattern 2 alpha
- Sugar pattern 2 beta
- III.4 Everything else...
- Conjugated double bond
- Conjugated tripple bond
- Cis double bond
- Trans double bond
- Mixed anhydrides
- Halogen on hetero
- Halogen multi subst
- Trifluoromethyl
- C ONS bond
- Charged
- Anion
- Kation
- Salt
- 1,3-Tautomerizable
- 1,5-Tautomerizable
- Rotatable bond
- Michael acceptor
- Dicarbodiazene
- CH-acidic
- CH-acidic strong
- Chiral center specified
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Sodium borohydride
Catalog No.
13432
Name
Alfa Aesar
CAS Number
16940-66-2
Website
M. F.
BNa
Telephone
M. W.
33.80077
Fax
Purity
98%
Email
Storage
Chembase ID: 102741
PRICE
Please log in
SYNONYMS
Title
硼氢化钠
IUPAC name
sodium boranuide
IUPAC Traditional name
sodium boranuide
Synonyms
Sodium tetrahydridoborate
DATABASE IDS
MDL Number
MFCD00003518
Merck Index
148592
EC Number
241-004-4
CAS Number
16940-66-2
PROPERTIES
Purity
98%
Apperance
Powder
Density
1.074
Melting Point
400°C dec.
GHS Pictograms
GHS Pictograms
GHS Pictograms
GHS Hazard statements
H301-H311-H331-H314-H318-H261
European Hazard Symbols
Toxic (T)
European Hazard Symbols
Flammable (F)
GHS Precautionary statements
P280-P303+P361+P353-P305+P351+P338-P310-P370+P378I-P402+P404
Risk Statements
15-23/24/25-34
RTECS
ED3325000
Safety Statements
7/8-26-36/37/39-43-45
Storage Warning
Moisture Sensitive
TSCA Listed
是
Hazard Class
4.3
UN Number
UN1426
Packing Group
I
DETAILS
REFERENCES
The reduction of aldehydes and ketones to alcohols occurs in alcoholic or aqueous media. For highly selective reduction of aldehydes in the presence of ketones, see:
Synth. Commun
.,
18
, 1927 (1988). For enantioselective reduction, see
L-tert-Leucine, L13707
. Borohydride reductions can be carried out in organic solvents, e.g. toluene, under phase-transfer conditions, amenable to scale-up:
Org. Process Res. Dev.
,
1
, 287 (1997).
Hydroboration of olefins has also been reported under similar conditions:
Synlett
, 997 (2000).
Acid chlorides are readily reduced to alcohols; controlled reduction at -78
o
to give the aldehyde has been reported; see, e.g.:
Synth. Commun
.,
12
, 839 (1982). See also
Bis(triphenylphosphine)copper(I) borohydride, A13730
. For an indirect method of reduction, see
Triethyl phosphite, L00339
.
A vast number of modified borohydride reagents have been reported, with the objective either of increasing the reducing power or improving selectivity. Many examples involve combinations with metal salts:
Reductive alkylation of amines can be effected with NaBH
4
/formaldehyde; see e.g.:
Synthesis
, 743 (1980); or TFA:
Synthesis
, 709 (1987). See also
Sodium cyanoborohydride, 87839
. Reductive alkylation of aromatic amines with a variety of aldehydes and ketones has been reported, using NaBH
4
/H
2
SO
4
:
Synthesis
, 121 (1993).
For a brief feature on uses of the reagent in synthesis, see:
Synlett
, 182 (2005).
Monograph: J. Seyden-Penne,
Reductions by the Alumino- and Borohydrides In Organic Synthesis
, 2nd ed., Wiley, N.Y. (1997).
LiCl: reduction of amino acids via Me esters:
Tetrahedron Lett.
,
39
, 917 (1998). CaCl
2
: selective 1,2-reduction enones:
Chem. Lett.
, 1847 (1991). CeCl
3
: increased selectivity for 1,2-reduction of enones:
J. Chem. Soc., Chem. Commun.
, 601 (1978); reduction of ketones in the presence of aldehydes:
J. Am. Chem. Soc.
,
101
, 5848 (1979). CuCl: dehalogenation of aryl iodides and bromides:
J. Org. Chem.
,
54
, 5308 (1989); reduction of nitro compounds:
Chem. Ind. (London)
, 75 (1984). CuSO
4
: reduction of esters, alkenes, nitriles and nitro compounds; amides and acids inert:
Synlett
, 419 (1990) [but see also
Synlett
, 79 (1993): Cu(OAc)
2
preferred for reduction of nitro-groups]; reduction of azides:
Synth. Commun.
,
24
, 549 (1994). NiCl
2
: generation
in situ
of nickel boride, as an alternative to Raney nickel for desulfurizations:
Synth. Commun.
,
16
, 779 (1986);
J. Chem. Soc., Chem. Commun.
, 819 (1990);
J. Org. Chem.
,
57
, 1986 (1992);
58
, 2407 (1993); phenols and enols have also been deoxygenated:
J. Chem. Soc., Perkin 1
, 1897 (1992), and aryl nitrile reduced to benzylamines:
Synth. Commun
,
32
, 1265 (2002). For conversion to Zn(BH
4
)
2
, see
Zinc chloride, A16281
. InCl
3
: radical reducing system - alternative to Bu
3
SnH:
J. Am. Chem. Soc.
,
124
, 906 (2002)
.
The combination of borohydride and iodine (
in situ
borane) reduces acids to alcohols:
J. Org. Chem.
,
56
, 5964 (1991); amino acids to amino alcohols:
J. Org. Chem.
,
58
, 3568 (1993); and effects reduction of esters, amides and nitriles, as well as hydroboration of alkenes:
Tetrahedron
,
45
, 4623 (1992). See also
Boron trifluoride diethyl etherate, A15275
, and
Sodium triacetoxyborohydride, B22060
.