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533-30-2 Usage

Chemical Properties

Yellow solid

Uses

Different sources of media describe the Uses of 533-30-2 differently. You can refer to the following data:
1. 6-Aminobenzothiazole is used as pharmaceutical intermediate.
2. 6-Aminobenzothiazole may be used in the synthesis of following:1-(6-amino-benzothiazolyl)-3-chloro-5-methoxytriazine6-[(4-N,N-dimethylaminophenyl)diazenyl]benzothiazole6-[(2-hydroxy-1-naphthyl)diazenyl]benzothiazole6-dimethylaminobenzothiazole

General Description

6-Aminobenzothiazole can be prepared from 6-nitrobenzothiazole via sonochemical reduction method.

Purification Methods

It crystallises from aqueous EtOH, pet ether or *C6H6/pet ether. The hydrochloride has m 305o(dec) from dilute HCl, and the picrate has m 185o(dec ) from Me2CO. [Boggust & Cocker J Chem Soc 360 1949, Beilstein 27 III/IV 4884.]

Check Digit Verification of cas no

The CAS Registry Mumber 533-30-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,3 and 3 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 533-30:
(5*5)+(4*3)+(3*3)+(2*3)+(1*0)=52
52 % 10 = 2
So 533-30-2 is a valid CAS Registry Number.
InChI:InChI=1/C7H6N2S/c8-5-1-2-6-7(3-5)10-4-9-6/h1-4H,8H2

533-30-2 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Detail
  • Alfa Aesar

  • (A12601)  6-Aminobenzothiazole, 98+%   

  • 533-30-2

  • 1g

  • 700.0CNY

  • Detail
  • Alfa Aesar

  • (A12601)  6-Aminobenzothiazole, 98+%   

  • 533-30-2

  • 5g

  • 2929.0CNY

  • Detail
  • Alfa Aesar

  • (A12601)  6-Aminobenzothiazole, 98+%   

  • 533-30-2

  • 25g

  • 12404.0CNY

  • Detail
  • Aldrich

  • (562440)  6-Aminobenzothiazole  97%

  • 533-30-2

  • 562440-1G

  • 773.37CNY

  • Detail
  • Aldrich

  • (562440)  6-Aminobenzothiazole  97%

  • 533-30-2

  • 562440-5G

  • 3,092.31CNY

  • Detail

533-30-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 6-Aminobenzothiazole

1.2 Other means of identification

Product number -
Other names 6-Benzothiazolamine

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:533-30-2 SDS

533-30-2Synthetic route

6-nitrobenzo[d]thiazole
2942-06-5

6-nitrobenzo[d]thiazole

1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

Conditions
ConditionsYield
With hydrogen In methanol; ethyl acetate at 80℃; for 0.333333h; Flow reactor; Green chemistry; chemospecific reaction;94%
With copper(II) phthalocyanine; hydrazine hydrate In ethylene glycol at 100℃; for 2h; chemoselective reaction;93%
With hydrogenchloride; iron In ethanol; water for 1h; Reflux;91.7%
carbon dioxide
124-38-9

carbon dioxide

2-amino-5-nitrobenzenethiol
23451-98-1

2-amino-5-nitrobenzenethiol

1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

Conditions
ConditionsYield
With 1-methyl-pyrrolidin-2-one; H2SiEt2; DBN at 150℃; under 37503.8 Torr; for 24h;35%
2-fluoro-6-nitro-benzothiazole
1131-75-5

2-fluoro-6-nitro-benzothiazole

1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

Conditions
ConditionsYield
With hydrogenchloride; tin In ethanol for 1h; Heating;6%
formic acid
64-18-6

formic acid

2,5-diaminothiophenol
507246-12-0

2,5-diaminothiophenol

1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

2-chloro-6-nitrobenzothiazole
2407-11-6

2-chloro-6-nitrobenzothiazole

1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

Conditions
ConditionsYield
With palladium Hydrogenation;
With sulfuric acid Electrolysis;
With hydrogenchloride; tin; acetic acid
6-nitro-benzthiazole

6-nitro-benzthiazole

1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

Conditions
ConditionsYield
With hydrogenchloride; tin
2-chloro-6-nitrobenzothiazole
2407-11-6

2-chloro-6-nitrobenzothiazole

sodium-salt of/the/ 2-hydroxy-5-sulfino-benzoic acid

sodium-salt of/the/ 2-hydroxy-5-sulfino-benzoic acid

1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 99 percent / anhydrous potassium fluoride / 18-crown-6-acetonitrile complex / acetonitrile / 4 h / Heating
2: 6 percent / tin, conc. hydrochloric acid / ethanol / 1 h / Heating
View Scheme
1,3-Benzothiazole
95-16-9

1,3-Benzothiazole

1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: HNO3; H2SO4
2: iron-powder; aqueous acetic acid
View Scheme
Multi-step reaction with 2 steps
1: HNO3; concentrated H2SO4
2: palladium; aqueous methanol. HCl / Hydrogenation
View Scheme
Multi-step reaction with 2 steps
1: sulfuric acid; nitric acid / 0 - 20 °C
2: hydrogenchloride; iron / ethanol / 0.67 h / Sonication
View Scheme
Multi-step reaction with 2 steps
1: sulfuric acid; nitric acid / 12 h / 0 - 20 °C
2: iron; acetic acid / ethanol / 3 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: nitric acid
2: tin(ll) chloride
View Scheme
6-nitro-2(3H)-benzothiazolone
28620-12-4

6-nitro-2(3H)-benzothiazolone

1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: PCl5; POCl3
2: tin; aqueous HCl; acetic acid
View Scheme
2-amino-6-nitrobenzothiazole
6285-57-0

2-amino-6-nitrobenzothiazole

1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aqueous H2SO4 / Diazotization.anschliessend Erwaermen
2: PCl5; POCl3
3: tin; aqueous HCl; acetic acid
View Scheme
6-nitrobenzo[d]thiazole
2942-06-5

6-nitrobenzo[d]thiazole

A

1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

B

N-(benzo[d]thiazol-6-yl)hydroxylamine

N-(benzo[d]thiazol-6-yl)hydroxylamine

Conditions
ConditionsYield
With hydrazine hydrate In tetrahydrofuran for 4h; chemoselective reaction;
2,5-diaminothiophenol
507246-12-0

2,5-diaminothiophenol

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

Conditions
ConditionsYield
at 130℃; Molecular sieve;
1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

acetic anhydride
108-24-7

acetic anhydride

N-acetyl-6-aminobenzothiazole
58249-63-1

N-acetyl-6-aminobenzothiazole

Conditions
ConditionsYield
With pyridine at 20℃;100%
With silica-supported boric acid In neat (no solvent) at 50℃; for 1h;96%
1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

triphenylacetyl chloride
6068-70-8

triphenylacetyl chloride

N-benzothiazol-6-yl-2,2,2-triphenyl-acetamide

N-benzothiazol-6-yl-2,2,2-triphenyl-acetamide

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane for 48h;100%
1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

benzoyl chloride
98-88-4

benzoyl chloride

N-benzothiazol-6-yl-benzamide
135249-30-8

N-benzothiazol-6-yl-benzamide

Conditions
ConditionsYield
With pyridine at 20℃;100%
1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

propionic acid anhydride
123-62-6

propionic acid anhydride

C10H10N2OS
922920-21-6

C10H10N2OS

Conditions
ConditionsYield
With pyridine at 20℃;100%
1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

4-Nitrobenzenesulfonyl chloride
98-74-8

4-Nitrobenzenesulfonyl chloride

N-benzothiazol-6-yl-4-nitrobenzenesulfonamide
1290638-62-8

N-benzothiazol-6-yl-4-nitrobenzenesulfonamide

Conditions
ConditionsYield
With pyridine at 0℃; for 2h; Inert atmosphere;99%
With pyridine In dichloromethane at 20℃; for 3h;67%
With pyridine In dichloromethane at 20℃; for 3h;67%
tetrafluoroboric acid

tetrafluoroboric acid

1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

tert.-butylnitrite
540-80-7

tert.-butylnitrite

benzo[d]thiazole-6-diazonium tetrafluoroborate

benzo[d]thiazole-6-diazonium tetrafluoroborate

Conditions
ConditionsYield
In ethanol; water at 0 - 20℃; for 1h;99%
1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

carbon monoxide
201230-82-2

carbon monoxide

(2R,3S,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran-5-carbonyl azide

(2R,3S,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran-5-carbonyl azide

(2R,3S,4R)-N-(benzo[d]thiazol-6-ylcarbamoyl)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran-5-carboxamide

(2R,3S,4R)-N-(benzo[d]thiazol-6-ylcarbamoyl)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyran-5-carboxamide

Conditions
ConditionsYield
With 1,10-Phenanthroline; palladium diacetate In tetrahydrofuran at 20℃; under 7.50075 Torr; for 1.5h; Sealed tube; Schlenk technique;99%
1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

1-Naphthalenesulfonyl chloride
85-46-1

1-Naphthalenesulfonyl chloride

N-(benzothiazol-6-yl)naphthalene-1-sulfonamide

N-(benzothiazol-6-yl)naphthalene-1-sulfonamide

Conditions
ConditionsYield
With pyridine at 0℃; for 2h; Inert atmosphere;98.5%
1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

5-methyl-indole-2,3-dione
608-05-9

5-methyl-indole-2,3-dione

3-(benzothiazol-6-ylimino)-1,3-dihydro-5-methyl-2H-indole-2-one
1391950-07-4

3-(benzothiazol-6-ylimino)-1,3-dihydro-5-methyl-2H-indole-2-one

Conditions
ConditionsYield
In water at 20℃; for 3h;98%
1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

indole-2,3-dione
91-56-5

indole-2,3-dione

3-(benzothiazol-6-ylimino)-1,3-dihydro-2H-indole-2-one
1391950-05-2

3-(benzothiazol-6-ylimino)-1,3-dihydro-2H-indole-2-one

Conditions
ConditionsYield
In water at 20℃; for 3h;98%
1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

4-Fluorobenzenesulfonyl chloride
349-88-2

4-Fluorobenzenesulfonyl chloride

N-benzothiazol-6-yl-4-fluorobenzenesulfonamide

N-benzothiazol-6-yl-4-fluorobenzenesulfonamide

Conditions
ConditionsYield
With pyridine at 0℃; for 2h; Inert atmosphere;97%
1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

2,5-diaminobenzenesulfonic acid
88-45-9

2,5-diaminobenzenesulfonic acid

Conditions
ConditionsYield
With [RuCl(P(C6H5)3)2(O(C6H4)NCH(C4H3N))]; bromamine B; sodium hydroxide In water; acetonitrile at 39.84℃; for 4.33333h;96%
1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

5-fluoro-1H-indole-2,3-dione
443-69-6

5-fluoro-1H-indole-2,3-dione

3-(benzothiazol-6-ylimino)-5-fluoro-1,3-dihydro-2H-indole-2-one
1391950-06-3

3-(benzothiazol-6-ylimino)-5-fluoro-1,3-dihydro-2H-indole-2-one

Conditions
ConditionsYield
In water at 20℃; for 3.5h;96%
1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

N-benzothiazol-6-ylbenzenesulfonamide

N-benzothiazol-6-ylbenzenesulfonamide

Conditions
ConditionsYield
With pyridine at 0℃; for 2h; Inert atmosphere;96%
1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

chloral hydrate
302-17-0

chloral hydrate

N-benzothiazol-6-yl-2-hydroxyimino-acetamide
222036-21-7

N-benzothiazol-6-yl-2-hydroxyimino-acetamide

Conditions
ConditionsYield
With hydrogenchloride; hydroxylamine hydrochloride; sodium sulfate In ethanol for 0.25h; Heating;94%
Stage #1: 1,3-benzothiazol-6-amine With hydrogenchloride; sodium sulfate In ethanol; water
Stage #2: chloral hydrate With hydroxylamine hydrochloride In ethanol; water for 0.25h; Heating / reflux;
94%
With hydrogenchloride; hydroxylamine hydrochloride; sodium sulfate In water
tetrahydrofuran-2,4-dione
4971-56-6

tetrahydrofuran-2,4-dione

1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

3,4,5-trimethoxy-benzaldehyde
86-81-7

3,4,5-trimethoxy-benzaldehyde

10-(3,4,5-trimethoxyphenyl)-6,7,9,10-tetrahydrofuro[3,4-b][1,3]thiazolo[5,4-f]quinolin-9-one

10-(3,4,5-trimethoxyphenyl)-6,7,9,10-tetrahydrofuro[3,4-b][1,3]thiazolo[5,4-f]quinolin-9-one

Conditions
ConditionsYield
In ethanol for 1h; Reflux;94%
1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

2-cyclopropyl pyrimidine 4-carbaldehyde

2-cyclopropyl pyrimidine 4-carbaldehyde

Dimethyl phosphite
868-85-9

Dimethyl phosphite

dimethyl (benzo[d]thiazol-6-ylamino)(2-cyclopropylpyrimidin-4-yl)methylphosphonate
1610793-36-6

dimethyl (benzo[d]thiazol-6-ylamino)(2-cyclopropylpyrimidin-4-yl)methylphosphonate

Conditions
ConditionsYield
With phosphomolybdic acid In dichloromethane at 20℃; for 0.333333h; Kabachnik-Fields Reaction; Inert atmosphere;94%
1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

4-methyl-3-oxopentanonitrile
29509-06-6

4-methyl-3-oxopentanonitrile

1-(benzo[d]thiazol-6-yl)-3-isopropyl-1H-pyrazol-5-amine
1020173-74-3

1-(benzo[d]thiazol-6-yl)-3-isopropyl-1H-pyrazol-5-amine

Conditions
ConditionsYield
Stage #1: 1,3-benzothiazol-6-amine With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 1.25h;
Stage #2: With hydrogenchloride; tin(ll) chloride In water at 20℃; for 2h;
Stage #3: 4-methyl-3-oxopentanonitrile In ethanol; water at 75℃; for 18h;
93%
Stage #1: 1,3-benzothiazol-6-amine With hydrogenchloride; tin(II) chloride dihdyrate; sodium nitrite In water at 0 - 20℃; for 3.25h;
Stage #2: 4-methyl-3-oxopentanonitrile In ethanol at 75℃; for 18h;
1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

6-(tert-butoxycarbonylamino)benzo[d]thiazole
1192841-91-0

6-(tert-butoxycarbonylamino)benzo[d]thiazole

Conditions
ConditionsYield
With zinc perchlorate In tert-butyl alcohol at 80℃; for 3h;93%
1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

benzaldehyde
100-52-7

benzaldehyde

6-(N-benzylamino)benzothiazole
1370531-82-0

6-(N-benzylamino)benzothiazole

Conditions
ConditionsYield
With cobalt(II) phthalocyanine; diphenylsilane In ethanol at 70℃; for 12h; chemoselective reaction;92%
With copper(I) iodide; phenylsilane In ethanol at 80℃; for 4h;86%
1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

diphenyl hydrogen phosphite
4712-55-4

diphenyl hydrogen phosphite

2-cyclopropyl pyrimidine 4-carbaldehyde

2-cyclopropyl pyrimidine 4-carbaldehyde

diphenyl (benzo[d]thiazol-6-ylamino)(2-cyclopropylpyrimidin-4-yl)methylphosphonate
1610793-28-6

diphenyl (benzo[d]thiazol-6-ylamino)(2-cyclopropylpyrimidin-4-yl)methylphosphonate

Conditions
ConditionsYield
With phosphomolybdic acid In dichloromethane at 20℃; for 0.333333h; Kabachnik-Fields Reaction; Inert atmosphere;92%
With hydrogen trititanate In neat (no solvent) at 20℃; for 0.25h; Kabachnik-Fields Reaction; Green chemistry;90%
1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

N-(benzo[d]thiazol-6-yl)methanesulfonamide
1000312-89-9

N-(benzo[d]thiazol-6-yl)methanesulfonamide

Conditions
ConditionsYield
With pyridine at 25℃; for 0.583333h;91%
With triethylamine In dichloromethane at 20℃; for 3h;42.1%
1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

5-methoxy-1-benzofuran-2-carbaldehyde
23145-19-9

5-methoxy-1-benzofuran-2-carbaldehyde

diphenyl hydrogen phosphite
4712-55-4

diphenyl hydrogen phosphite

diphenyl(benzo[d]thiazol-6-ylamino)(5-methoxybenzofuran-2-yl)methylphosphonate

diphenyl(benzo[d]thiazol-6-ylamino)(5-methoxybenzofuran-2-yl)methylphosphonate

Conditions
ConditionsYield
With hydrogen trititanate In neat (no solvent) at 20℃; for 0.25h; Kabachnik-Fields Reaction; Green chemistry;90%
1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

C18H20ClN2O3PS

C18H20ClN2O3PS

Conditions
ConditionsYield
With nanoporous AlSBA-15 aluminosilicate catalyst In neat (no solvent) at 50℃; for 0.666667h; Kabachnik-Fields Reaction;90%
1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

2-{2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)-1-ethenyl]phenoxy}acetic acid
763903-09-9

2-{2-methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)-1-ethenyl]phenoxy}acetic acid

C27H26N2O6S
1412872-15-1

C27H26N2O6S

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 24h;89%
1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

1,3,5-trichloro-2,4,6-triazine
108-77-0

1,3,5-trichloro-2,4,6-triazine

benzylamine
100-46-9

benzylamine

trifluoroacetic acid
76-05-1

trifluoroacetic acid

4-(benzothiazol-6-ylamino)-6-(benzylamino)-[1,3,5]triazin-2-ol ditrifluoroacetate

4-(benzothiazol-6-ylamino)-6-(benzylamino)-[1,3,5]triazin-2-ol ditrifluoroacetate

Conditions
ConditionsYield
Multistep reaction;88%
1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

trimethyl orthoformate
149-73-5

trimethyl orthoformate

5-((benzo[d]thiazol-6-ylamino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione
1195996-68-9

5-((benzo[d]thiazol-6-ylamino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Conditions
ConditionsYield
at 90℃; for 0.0333333h; Microwave irradiation;88%
1,3-benzothiazol-6-amine
533-30-2

1,3-benzothiazol-6-amine

Benzyl isothiocyanate
622-78-6

Benzyl isothiocyanate

C15H13N3S2
1255211-40-5

C15H13N3S2

Conditions
ConditionsYield
In methanol for 5h; Reflux;88%

533-30-2Relevant articles and documents

Paper strip-based fluorometric determination of cyanide with an internal reference

Lee, Dong-Nam,Seo, Hyejin,Shin, Ik-Soo,Hong, Jong-In

, p. 1320 - 1325 (2016)

The rapid, selective, and sensitive determination of cyanide anion (CN-) using a simple paper strip is highly attractive because cyanide is acutely lethal to living organisms via all routes of administration, including alcohol consumption and inhaling cigarette smoke. Here, a synthetic probe (1) was designed for the selective determination of cyanide. The probe displays rapid and large blue spectral change (Δλabs =148 nm, Δλem = 165 nm) with respect to target recognition. Probe 1 exhibits a strong push-pull electronic effect and comprises a dimethylaminoaryl group as a donor and malononitrile as an acceptor; the π-conjugation system can be destroyed by the Michael-type addition of cyanide at the electrophilic β-positions of the nitrile groups, resulting in the marked emergence of a peak at λem = 515 nm. The developed probe was successfully applied to a paper test strip because of its noticeable optical changes upon reaction with cyanide. The fabricated dumbbell-shaped paper strip with an internal reference allowed the cyanide detection, which is indispensable for quantitative analysis in point-of-care testing. The paper strip test showed selective response to cyanide, with a linear correlation in the range of 0-25 mM in a simple and cost-effective manner.

Design, synthesis and biological evaluation of benz-fused five-membered heterocyclic compounds as tubulin polymerization inhibitors with anticancer activities

Komuraiah, Buduma,Ren, Yichang,Xue, Mingming,Cheng, Binbin,Liu, Jin,Liu, Yao,Chen, Jianjun

, p. 1109 - 1116 (2021/03/16)

A series of benz-fused five-membered heterocyclic compounds were designed and synthesized as novel tubulin inhibitors targeting the colchicine binding site. Among them, compound 4d displayed the highest antiproliferative activity against four cancer cell lines with an IC50 value of 4.9?μM in B16-F10 cells. Compound 4d effectively inhibited tubulin polymerization in vitro (IC50 of 13.1?μM). Further, 4d induced cell cycle arrest in G2/M phase. Finally, 4d inhibited the migration of cancer cells in a dose-dependent manner. In summary, these results suggest that compound 4d represents a new class of tubulin inhibitors deserving further investigation.

Cyclic (Alkyl)(amino)carbene Ligand-Promoted Nitro Deoxygenative Hydroboration with Chromium Catalysis: Scope, Mechanism, and Applications

Zhao, Lixing,Hu, Chenyang,Cong, Xuefeng,Deng, Gongda,Liu, Liu Leo,Luo, Meiming,Zeng, Xiaoming

supporting information, p. 1618 - 1629 (2021/01/25)

Transition metal catalysis that utilizes N-heterocyclic carbenes as noninnocent ligands in promoting transformations has not been well studied. We report here a cyclic (alkyl)(amino)carbene (CAAC) ligand-promoted nitro deoxygenative hydroboration with cost-effective chromium catalysis. Using 1 mol % of CAAC-Cr precatalyst, the addition of HBpin to nitro scaffolds leads to deoxygenation, allowing for the retention of various reducible functionalities and the compatibility of sensitive groups toward hydroboration, thereby providing a mild, chemoselective, and facile strategy to form anilines, as well as heteroaryl and aliphatic amine derivatives, with broad scope and particularly high turnover numbers (up to 1.8 × 106). Mechanistic studies, based on theoretical calculations, indicate that the CAAC ligand plays an important role in promoting polarity reversal of hydride of HBpin; it serves as an H-shuttle to facilitate deoxygenative hydroboration. The preparation of several commercially available pharmaceuticals by means of this strategy highlights its potential application in medicinal chemistry.

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