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25895-60-7 Usage

Uses

Sodium Cyanoborohydride is a commonly used as a reagent in the reductive amination of aldehydes and ketones and in the reductive alkylation of amines. Reagent for selective reductions. Used in the synthesis of a novel phenolate-bridged dilanthanum(III) complex of interest as a model for metalloproteins as well as for its importance in basic and applied chemistry.

Purification Methods

It is avery hygroscopic solid, soluble in H2O (212% at 29o, 121% at 88o), tetrahydrofuran (37% at 28o, 42.2% at 62o), very soluble in MeOH, slightly soluble in EtOH but insoluble in Et2O, *C6H6 and hexane. It is stable to acid up to pH 3 but is hydrolysed in 12N HCl. The rate of hydrolysis at pH 3 is 10-8 times that of NaBH4. The fresh commercially available material is usually sufficiently pure. If very pure material is required, one of the following procedures can be used [Lane Synthesis 135 1975]: (a) The NaBH3CN is dissolved in tetrahydrofuran (20% w/v), filtered and the filtrate is treated with a fourfold volume of CH2Cl2. The solid is collected and dried in a vacuum [Wade et al. Inorg Chem. 9 2146 1970]. (b) NaBH3CN is dissolved in dry MeNO3, filtered, and the filtrate is poured into a 10-fold volume of CCl4 with vigorous stirring; the white precipitate is collected, washed several times with CCl4 and dried in a vacuum (yield 75%) [Berschied & Purcell Inorg Chem 9 624 1970]. (c) When the above procedures fail to give a clean product, then dissolve NaBH3CN (10g) in tetrahydrofuran (80mL) and add N MeOH/HCl until the pH is 9. Pour the solution with stirring into dioxane (250mL). The solution is filtered and heated to reflux. A further volume of dioxane (150mL) is added slowly with swirling. The solution is cooled slowly to room temperature, then chilled in ice and the crystalline dioxane complex is collected, dried in a vacuum for 4hours at 25o, then 4hours at 80o to yield the amorphous dioxane-free powder (6.7g) with purity >98% [Borch et al. J Am Chem Soc 93 2897 1971]. The purity can be checked by iodometric titration [Lyttle et al. Anal Chem 24 1843 1952].

Uses

Selective reducing agent for aldehydes, ketones, oximes, enamines; does not reduce amides, ethers, lactones, nitriles, nitro Compounds and epoxides. Also used for reductive amination of ketones and aldehydes, reductive alkylation of amines and hydrazines, reductive displacement of halides and tosylates, deoxygenation of aldehydes and ketones. See Lane, loc. cit.

Description

Sodium cyanoborohydride (NaBH3CN) is a selective reducing agent used for a variety of chemical reductions, including aldehyde, ketones,? acetals, epoxides, oximes, enamines, reductive aminations of aldehydes and ketones, and reductive alkylations of amines and hydrazines. The utility of sodium cyanoborohydride as a reducing agent is greatly enhanced by its stability under acid conditions, and its solubility in aprotic solvents. Sodium cyanoborohydride is a milder and more selective reducing agent than sodium borohydride. Sodium cyanoborohydride is a weaker and more-selective reducing agent than sodium borohydride because of the electron-withdrawing effect of the cyano group. It has the further advantage that it is stable in acid to pH = 3 and can be employed to effect reductions in the presence of functional groups that are sensitive to the more-basic conditions of reduction with sodium borohydride. Aldehydes and ketones are unaffected by sodium cyanoborohydride in neutral solution, but they are readily reduced to the corresponding alcohol at pH=3-4 by way of the protonated carbonyl group. By previous exchange of the hydrogens of the borohydride for deuterium or tritium, by reaction with D2O or tritiated water, an efficient and economical route is available for deuteride or tritiide reduction of aldehydes and ketones.

Chemical Properties

White solid

Uses

Sodium cyanoborohydride are frequently used for reductive aminations. Since the reaction rate for the reduction of iminium ions is much faster than for ketones or even aldehydes, the reductive amination can be carried out as a one-pot procedure by introducing the reducing agent into a mixture of the amine and carbonyl compound. Contact with strong acids liberates the highly toxic gas HCN. A safer reducing agent with comparable reactivity is sodium triacetoxyborohydride. Reduction with Sodium Cyanoborohydride: Tin-free Giese reaction of alkyl iodides with electron-deficient alkenes and the related radical carbonylation process proceeded efficiently in the presence of sodium cyanoborohydride and tetrabutylammonium cyanoborohydride. Transfer of iodine followed by hydride reduction of the resulting carbon-iodine bond is proposed as a possible mechanism. Borch and co-workers showed that sodium cyanoborohydride and lithium cyanoborohydride are acid-stable reagents capable of rapidly reducing carbonyl compounds to alcohols at pH 3–4, presumably via a protonated carbonyl cation. With care to maintain a pH of 6–7, a mixture of a ketone or aldehyde reactant, an amine, and sodium cyanohydride provides products of reductive amination selectively, without competitive reduction of the carbonyl substrate. Though the conditions of the Borch reduction are mild, sodium cyanoborohydride is highly toxic, as are its byproducts. The pH was maintained by addition of HCl and/or KOH as needed using bromocresol green as an indicator.
InChI:InChI=1/CH3BN.Na/c2-1-3;/h2H3;/q-1;+1

25895-60-7 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (S0396)  Sodium Cyanoborohydride [Reducing Agent]  >95.0%(T) 25895-60-7 5g 390.00CNY Detail
TCI America (S0396)  Sodium Cyanoborohydride [Reducing Agent]  >95.0%(T) 25895-60-7 25g 1,190.00CNY Detail
TCI America (S0396)  Sodium Cyanoborohydride [Reducing Agent]  >95.0%(T) 25895-60-7 250g 6,990.00CNY Detail
Alfa Aesar (87839)  Sodium cyanoborohydride, 95%    25895-60-7 5g 216.0CNY Detail
Alfa Aesar (87839)  Sodium cyanoborohydride, 95%    25895-60-7 25g 976.0CNY Detail
Alfa Aesar (87839)  Sodium cyanoborohydride, 95%    25895-60-7 100g 3680.0CNY Detail
Sigma-Aldrich (42077)  Sodiumcyanoborohydride  PharmaGrade, Manufactured under appropriate controls for use as a raw material in pharma or biopharmaceutical production. 25895-60-7 42077-10G 1,386.45CNY Detail
Sigma-Aldrich (42077)  Sodiumcyanoborohydride  PharmaGrade, Manufactured under appropriate controls for use as a raw material in pharma or biopharmaceutical production. 25895-60-7 42077-100G 11,577.15CNY Detail
Sigma-Aldrich (42077)  Sodiumcyanoborohydride  PharmaGrade, Manufactured under appropriate controls for use as a raw material in pharma or biopharmaceutical production. 25895-60-7 42077-1KG 86,872.50CNY Detail
Aldrich (156159)  Sodiumcyanoborohydride  reagent grade, 95% 25895-60-7 156159-10G 628.29CNY Detail
Aldrich (156159)  Sodiumcyanoborohydride  reagent grade, 95% 25895-60-7 156159-25G 972.27CNY Detail
Aldrich (156159)  Sodiumcyanoborohydride  reagent grade, 95% 25895-60-7 156159-50G 1,937.52CNY Detail

25895-60-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name Sodium cyanoborohydride

1.2 Other means of identification

Product number -
Other names Sodium cyonobrohydriole

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:25895-60-7 SDS

25895-60-7Synthetic route

(1S,2R)-1-(3,4-dichlorophenyl)-2-formyl-cyclopropanecarboxylic acid (4-fluorobenzyl)methylamide
846060-69-3

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

(1,3-dioxolan-2-yl-methyl)triphenylphosphonium bromide
52509-14-5

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

sodium cyanoborohydride
25895-60-7

sodium cyanoborohydride

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

sodium tetrahydroborate

mercury(II) cyanide
592-04-1

mercury(II) cyanide

sodium cyanoborohydride
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%
sodium tetrahydroborate
16940-66-2

sodium tetrahydroborate

hydrogen cyanide
74-90-8

hydrogen cyanide

sodium cyanoborohydride
25895-60-7

sodium cyanoborohydride

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

sodium tetrahydroborate

hydrogen cyanide
74-90-8

hydrogen cyanide

A

sodium cyanide
773837-37-9

sodium cyanide

B

sodium cyanoborohydride
29012-60-0

sodium cyanoborohydride

C

sodium cyanobis(trihydroborate)
29012-61-1

sodium cyanobis(trihydroborate)

D

sodium cyanoborohydride
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
sodium cyanoborohydride
25895-60-7

sodium cyanoborohydride

N-(4-iodobenzyl)hydroxylamine
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%
phenylacetaldehyde
122-78-1

phenylacetaldehyde

sodium cyanoborohydride
25895-60-7

sodium cyanoborohydride

isopentyl-phenethyl-amine
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%
formic acid
64-18-6

formic acid

sodium cyanoborohydride
25895-60-7

sodium cyanoborohydride

N-benzyloxy-N-((2S,3S,4R)-2,3,4-tris-benzyloxy-5-triisopropylsilanyloxy-pentyl)-formamide
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%
sodium cyanoborohydride
25895-60-7

sodium cyanoborohydride

2'-O-[(2-formadoxyiminooxy)ethyl]-5'-O-tert-butyldiphenylsilyl-5-methyluridine
212061-26-2

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

5'-O-tert-butyldiphenylsilyl-2'-O-[N,N dimethylaminooxyethyl]-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%
formaldehyd
50-00-0

formaldehyd

1-Aminoapocamphor
38989-02-5

1-Aminoapocamphor

sodium cyanoborohydride
25895-60-7

sodium cyanoborohydride

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

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%
2,5-dimethylthiophene-3,4-dicarboxaldehyde
5368-72-9

2,5-dimethylthiophene-3,4-dicarboxaldehyde

sodium cyanoborohydride
25895-60-7

sodium cyanoborohydride

methylamine
74-89-5

methylamine

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

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

Conditions
ConditionsYield
With acetic acid In methanol at 20℃; for 18h; Inert atmosphere; Schlenk technique;86%
2,5-dimethylthiophene-3,4-dicarboxaldehyde
5368-72-9

2,5-dimethylthiophene-3,4-dicarboxaldehyde

sodium cyanoborohydride
25895-60-7

sodium cyanoborohydride

ethylamine
75-04-7

ethylamine

C10H15NS*CH3BN(1-)*H(1+)

C10H15NS*CH3BN(1-)*H(1+)

Conditions
ConditionsYield
With acetic acid In methanol at 20℃; for 18h; Inert atmosphere; Schlenk technique;88%
2,5-dimethylthiophene-3,4-dicarboxaldehyde
5368-72-9

2,5-dimethylthiophene-3,4-dicarboxaldehyde

isobutylamine
78-81-9

isobutylamine

sodium cyanoborohydride
25895-60-7

sodium cyanoborohydride

C12H19NS*CH3BN(1-)*H(1+)

C12H19NS*CH3BN(1-)*H(1+)

Conditions
ConditionsYield
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

2,2,2-trifluoro-1-(4‘-(methylsulfonyl)-[1,1'-biphenyl]-4-yl)ethanone

sodium cyanoborohydride
25895-60-7

sodium cyanoborohydride

ethyl (2S)-2-amino-4-fluoro-4-methylpentanoate sulfate salt

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

(S)-4-fluoro-4-methyl-2-(((S)-2,2,2-trifluoro-1-(4’-(methylsulfonyl)-[1,1'-biphenyl]-4-yl)ethyl)amino)pentanoic acid

Conditions
ConditionsYield
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

5-formyl-2,2-dimethyl-4H-[1,3]dioxino[4,5-c]pyridine-8-carboxylic acid methyl ester

sodium cyanoborohydride
25895-60-7

sodium cyanoborohydride

4-fluoroaniline
371-40-4

4-fluoroaniline

methyl 5-((4-fluorophenylamino)methyl)-2,2-dimethyl-4H-[1,3]dioxino[4,5-c]pyridine-8-carboxylate
1198621-26-9

methyl 5-((4-fluorophenylamino)methyl)-2,2-dimethyl-4H-[1,3]dioxino[4,5-c]pyridine-8-carboxylate

Conditions
ConditionsYield
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

9-fluorenylmethoxy carbonyl-4-piperidone

t-butoxycarbonylhydrazine
870-46-2

t-butoxycarbonylhydrazine

sodium cyanoborohydride
25895-60-7

sodium cyanoborohydride

C25H29N3O4

C25H29N3O4

Conditions
ConditionsYield
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

propylamine

2,5-dimethylthiophene-3,4-dicarboxaldehyde
5368-72-9

2,5-dimethylthiophene-3,4-dicarboxaldehyde

sodium cyanoborohydride
25895-60-7

sodium cyanoborohydride

C11H17NS*CH3BN(1-)*H(1+)

C11H17NS*CH3BN(1-)*H(1+)

Conditions
ConditionsYield
With acetic acid In methanol at 20℃; for 18h; Inert atmosphere; Schlenk technique;83%
2,5-dimethylthiophene-3,4-dicarboxaldehyde
5368-72-9

2,5-dimethylthiophene-3,4-dicarboxaldehyde

sodium cyanoborohydride
25895-60-7

sodium cyanoborohydride

isopropylamine
75-31-0

isopropylamine

C11H17NS*CH3BN(1-)*H(1+)

C11H17NS*CH3BN(1-)*H(1+)

Conditions
ConditionsYield
With acetic acid In methanol at 20℃; for 18h; Inert atmosphere; Schlenk technique;80%
2,5-dimethylthiophene-3,4-dicarboxaldehyde
5368-72-9

2,5-dimethylthiophene-3,4-dicarboxaldehyde

sodium cyanoborohydride
25895-60-7

sodium cyanoborohydride

tert-butylamine
75-64-9

tert-butylamine

C12H19NS*CH3BN(1-)*H(1+)

C12H19NS*CH3BN(1-)*H(1+)

Conditions
ConditionsYield
With acetic acid In methanol at 20℃; for 18h; Inert atmosphere; Schlenk technique;82%
C17H14FN3O2S

C17H14FN3O2S

sodium cyanoborohydride
25895-60-7

sodium cyanoborohydride

C18H19FN4OS

C18H19FN4OS

Conditions
ConditionsYield
With titanium(IV)isopropoxide In tetrahydrofuran at 20℃; for 12h;70%
N-benzyl-3-pyrrolidinone
775-16-6

N-benzyl-3-pyrrolidinone

t-butoxycarbonylhydrazine
870-46-2

t-butoxycarbonylhydrazine

sodium cyanoborohydride
25895-60-7

sodium cyanoborohydride

tert-butyl 2-(1-benzylpyrrolidin-3-yl)hydrazinecarboxylate
1292303-81-1

tert-butyl 2-(1-benzylpyrrolidin-3-yl)hydrazinecarboxylate

Conditions
ConditionsYield
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

sodium cyanoborohydride

methyl 1-(2-propenyl)-2-oxocyclopentanecarboxylate
74036-93-4, 111239-40-8

methyl 1-(2-propenyl)-2-oxocyclopentanecarboxylate

C10H17NO2

C10H17NO2

Conditions
ConditionsYield
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

benzyl 2-formyl-7-azaspiro[3.5]nonane-7-carboxylate

sodium cyanoborohydride
25895-60-7

sodium cyanoborohydride

methylamine
74-89-5

methylamine

benzyl 2-((methylamino)methyl)-7-azaspiro[3.5]nonane-7-carboxylate

benzyl 2-((methylamino)methyl)-7-azaspiro[3.5]nonane-7-carboxylate

Conditions
ConditionsYield
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

(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

sodium cyanoborohydride
25895-60-7

sodium cyanoborohydride

(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

(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
ConditionsYield
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

4-(chloromethyl)-1-(2,4-dichlorophenyl)-1H-pyrazole

sodium cyanoborohydride
25895-60-7

sodium cyanoborohydride

2-(1-(2,4-dichlorophenyl)-1H-pyrazole-4-yl)acetonitrile

2-(1-(2,4-dichlorophenyl)-1H-pyrazole-4-yl)acetonitrile

Conditions
ConditionsYield
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-)

C12H34B2N3(1+)*Br(1-)

sodium cyanoborohydride
25895-60-7

sodium cyanoborohydride

C12H34B2N3(1+)*CH3BN(1-)

C12H34B2N3(1+)*CH3BN(1-)

Conditions
ConditionsYield
In acetonitrile at 20℃; for 18h;88.9%
C5H18BN2(1+)*Cl(1-)

C5H18BN2(1+)*Cl(1-)

sodium cyanoborohydride
25895-60-7

sodium cyanoborohydride

C5H18BN2(1+)*CH3BN(1-)

C5H18BN2(1+)*CH3BN(1-)

Conditions
ConditionsYield
In acetonitrile at 20℃; for 24h;87.9%
(R)-3-N-Cyclopentylamino-8-fluoro-5-methoxy-3,4-dihydro-2H-1-benzopyran

(R)-3-N-Cyclopentylamino-8-fluoro-5-methoxy-3,4-dihydro-2H-1-benzopyran

sodium cyanoborohydride
25895-60-7

sodium cyanoborohydride

propionaldehyde
123-38-6

propionaldehyde

(R)-3-(N-Cyclopentyl-N-n-propylamino)-8-fluoro-5-methoxy-3,4-dihydro-2H-1-benzopyran
169758-89-8

(R)-3-(N-Cyclopentyl-N-n-propylamino)-8-fluoro-5-methoxy-3,4-dihydro-2H-1-benzopyran

Conditions
ConditionsYield
With ammonia; acetic acid In methanol; ethyl acetate65%
With ammonia; acetic acid In methanol; ethyl acetate65%
tert-butyl [3-(2-amino-5-chlorophenoxy)benzyl]carbamate

tert-butyl [3-(2-amino-5-chlorophenoxy)benzyl]carbamate

sodium cyanoborohydride
25895-60-7

sodium cyanoborohydride

4-Phenylbenzaldehyde
3218-36-8

4-Phenylbenzaldehyde

tert-butyl [3-[2-(4-biphenylmethylamino)phenoxy]benzyl] carbamate

tert-butyl [3-[2-(4-biphenylmethylamino)phenoxy]benzyl] carbamate

Conditions
ConditionsYield
With acetic acid In methanol87.4%
sodium cyanoborohydride
25895-60-7

sodium cyanoborohydride

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-aminophenoxy)ethyl]piperazine

1-[(4-cyano-5-methyl-4-phenyl)hexyl]-4-[2-(4-dimethylaminophenoxy)ethyl]piperazine

1-[(4-cyano-5-methyl-4-phenyl)hexyl]-4-[2-(4-dimethylaminophenoxy)ethyl]piperazine

Conditions
ConditionsYield
With formaldehyd; sodium hydrogencarbonate In acetic acid; acetonitrile81%
[(1-Ethoxycyclopropyl)oxy]trimethylsilane
27374-25-0

[(1-Ethoxycyclopropyl)oxy]trimethylsilane

1-(4-fluorophenyl)-6-(piperidin-4-yloxy)-3,4-dihydroquinolin-2(1H)-one hydrochloride
1239768-76-3

1-(4-fluorophenyl)-6-(piperidin-4-yloxy)-3,4-dihydroquinolin-2(1H)-one hydrochloride

sodium cyanoborohydride
25895-60-7

sodium cyanoborohydride

6-[(1-cyclopropylpiperidin-4-yl)oxy]-1-(4-fluorophenyl)-3,4-dihydroquinolin-2(1H)-one
1239768-52-5

6-[(1-cyclopropylpiperidin-4-yl)oxy]-1-(4-fluorophenyl)-3,4-dihydroquinolin-2(1H)-one

Conditions
ConditionsYield
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%

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