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398489-26-4

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398489-26-4 Usage

Chemical Properties

White to light brown solid

Uses

1-Boc-3-azetidinone can be used for the preparation of antibacterial aminoglycoside analogs.

General Description

tert-Butyl 3-oxoazetidine-1-carboxylate is moisture sensitive and incompatible with oxidizing agents. This chemical can cause skin irritation and severe eye irritation.

Check Digit Verification of cas no

The CAS Registry Mumber 398489-26-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 3,9,8,4,8 and 9 respectively; the second part has 2 digits, 2 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 398489-26:
(8*3)+(7*9)+(6*8)+(5*4)+(4*8)+(3*9)+(2*2)+(1*6)=224
224 % 10 = 4
So 398489-26-4 is a valid CAS Registry Number.
InChI:InChI=1/C6H14N2.2ClH/c1-8-4-2-3-6(7)5-8;;/h6H,2-5,7H2,1H3;2*1H

398489-26-4 Well-known Company Product Price

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

  • (H50826)  1-Boc-3-azetidinone, 95%   

  • 398489-26-4

  • 250mg

  • 594.0CNY

  • Detail
  • Alfa Aesar

  • (H50826)  1-Boc-3-azetidinone, 95%   

  • 398489-26-4

  • 1g

  • 2136.0CNY

  • Detail
  • Aldrich

  • (696315)  1-Boc-3-azetidinone  97%

  • 398489-26-4

  • 696315-1G

  • 988.65CNY

  • Detail

398489-26-4SDS

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 tert-Butyl 3-oxoazetidine-1-carboxylate

1.2 Other means of identification

Product number -
Other names N-Boc-3-oxoazetidine

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:398489-26-4 SDS

398489-26-4Synthetic route

tert-butyl 3-hydroxyazetidine-1-carboxylate
141699-55-0

tert-butyl 3-hydroxyazetidine-1-carboxylate

tert-butyl 3-oxoazetidine-1-carboxylate
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

Conditions
ConditionsYield
With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide In acetonitrile at 0 - 20℃; for 18h; Inert atmosphere; Molecular sieve;99%
With 1-methyl-1H-imidazole; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate; 4,4'-Dimethoxy-2,2'-bipyridin; 9-azabicyclo[3.3.1]nonane N-oxyl; oxygen In acetonitrile at 20℃; for 0.5h; Time;98%
With pyridine-SO3 complex; triethylamine In dimethyl sulfoxide at 10 - 20℃; Inert atmosphere;95%
1,3-dibromoacetone ethylene glycol
20599-01-3

1,3-dibromoacetone ethylene glycol

tert-butyl carbamate
4248-19-5

tert-butyl carbamate

tert-butyl 3-oxoazetidine-1-carboxylate
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

Conditions
ConditionsYield
With sodium carbonate In 1,4-dioxane at 50℃; for 16h; Reagent/catalyst; Solvent; Temperature;92%
1-tert-butoxycarbonyl-3,3-dimethoxyazetidine

1-tert-butoxycarbonyl-3,3-dimethoxyazetidine

tert-butyl 3-oxoazetidine-1-carboxylate
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

Conditions
ConditionsYield
With citric acid In water; ethyl acetate at 20 - 40℃;85.4%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

3,3-dimethoxyazetidine

3,3-dimethoxyazetidine

tert-butyl 3-oxoazetidine-1-carboxylate
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 10 - 40℃;80.2%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

tert-butyl 3-oxoazetidine-1-carboxylate
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / tetrahydrofuran / 1 h / 20 °C
2: triethylamine / sulfur trioxide pyridine complex / chloroform; dimethyl sulfoxide / 4 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium hydrogencarbonate / 1,4-dioxane; water / 15 h / 20 °C
2: oxalyl dichloride; dimethyl sulfoxide; triethylamine / dichloromethane / 15 h / -78 - 20 °C
View Scheme
Multi-step reaction with 2 steps
1: triethylamine / ethanol / 16 h / 0 - 20 °C
2: pyridine-SO3 complex; triethylamine / dimethyl sulfoxide / 10 - 20 °C / Inert atmosphere
View Scheme
tert-butyl 3-hydroxyazetidine-1-carboxylate
141699-55-0

tert-butyl 3-hydroxyazetidine-1-carboxylate

A

tert-butyl 3-oxoazetidine-1-carboxylate
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

B

1,1-dimethylethyl 5-oxo-3-oxazolidinecarboxylate
172096-95-6

1,1-dimethylethyl 5-oxo-3-oxazolidinecarboxylate

Conditions
ConditionsYield
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium hydrogencarbonate; potassium bromide In dichloromethane; water at -10 - -5℃; Temperature;
methylene-carbamic acid tert-butyl ester
801290-71-1

methylene-carbamic acid tert-butyl ester

tert-butyl 3-oxoazetidine-1-carboxylate
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: trichlorophosphate / diethyl ether / Inert atmosphere; Schlenk technique; Reflux
2: zinc; acetic acid / 7 h / 20 - 80 °C / Inert atmosphere; Schlenk technique
View Scheme
C8H11Cl2NO3

C8H11Cl2NO3

tert-butyl 3-oxoazetidine-1-carboxylate
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

Conditions
ConditionsYield
With acetic acid; zinc at 20 - 80℃; for 7h; Inert atmosphere; Schlenk technique;
tert-butyl 3-oxoazetidine-1-carboxylate
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

dimethyl amine
124-40-3

dimethyl amine

tert-butyl 3-(dimethylamino)azetidine-1-carboxylate
792970-55-9

tert-butyl 3-(dimethylamino)azetidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: tert-butyl 3-oxoazetidine-1-carboxylate; dimethyl amine With hydrogen; acetic acid; palladium 10% on activated carbon In tetrahydrofuran; methanol at 20℃; for 14h;
Stage #2: With sodium hydrogencarbonate In water; ethyl acetate
100%
tert-butyl 3-oxoazetidine-1-carboxylate
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

Methyltriphenylphosphonium bromide
1779-49-3

Methyltriphenylphosphonium bromide

3-methylene-azetidine-1-carboxylic acid tert-butyl ester
934664-41-2

3-methylene-azetidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: potassium tert-butylate; Methyltriphenylphosphonium bromide In diethyl ether at 20℃; for 1h;
Stage #2: tert-butyl 3-oxoazetidine-1-carboxylate In diethyl ether at 35℃; for 2h;
100%
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In diethyl ether at 20℃; for 1h;
Stage #2: tert-butyl 3-oxoazetidine-1-carboxylate In diethyl ether at 35℃; for 2h;
100%
Stage #1: Methyltriphenylphosphonium bromide With potassium tert-butylate In diethyl ether at 20℃; for 1h;
Stage #2: tert-butyl 3-oxoazetidine-1-carboxylate In diethyl ether at 35℃; for 2h;
100%
tert-butyl 3-oxoazetidine-1-carboxylate
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

(triphenylphosphoranylidene)acetaldehyde
2136-75-6

(triphenylphosphoranylidene)acetaldehyde

tert-butyl 3-(2-oxomethylene)azetidine-1-carboxylic acid
1223573-23-6

tert-butyl 3-(2-oxomethylene)azetidine-1-carboxylic acid

Conditions
ConditionsYield
In dichloromethane at 40℃; for 6h;100%
In dichloromethane at 40℃; for 6h;100%
In dichloromethane at 40℃;99%
tert-butyl 3-oxoazetidine-1-carboxylate
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

tert-butyl 3-hydroxy-3-vinylazetidine-1-carboxylate
398489-51-5

tert-butyl 3-hydroxy-3-vinylazetidine-1-carboxylate

Conditions
ConditionsYield
In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;100%
In tetrahydrofuran at -20℃; for 0.5h; Inert atmosphere;99%
In tetrahydrofuran at -30℃; for 2h; Inert atmosphere;
tert-butyl 3-oxoazetidine-1-carboxylate
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

ethyl (triphenylphosphoranylidene)acetate
1099-45-2

ethyl (triphenylphosphoranylidene)acetate

tert-butyl 3-(2-ethoxy-2-oxoethylidene)azetidine-1-carboxylate
1002355-96-5

tert-butyl 3-(2-ethoxy-2-oxoethylidene)azetidine-1-carboxylate

Conditions
ConditionsYield
In dichloromethane for 6h; Wittig Olefination; Inert atmosphere; Schlenk technique; Reflux;100%
In dichloromethane at 40℃; for 4h; Cooling with ice;100%
In dichloromethane at 40℃; for 4.25h; Cooling with ice;100%
tert-butyl 3-oxoazetidine-1-carboxylate
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

tert-butyl diethylphosphonoacetate
27784-76-5

tert-butyl diethylphosphonoacetate

tert-butyl 3-(2-(tert-butoxy)-2-oxoethylidene)azetidine-1-carboxylate

tert-butyl 3-(2-(tert-butoxy)-2-oxoethylidene)azetidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: tert-butyl diethylphosphonoacetate With potassium tert-butylate In tetrahydrofuran at 0 - 20℃;
Stage #2: tert-butyl 3-oxoazetidine-1-carboxylate In tetrahydrofuran at 0 - 20℃;
100%
tert-butyl 3-oxoazetidine-1-carboxylate
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

(carbobenzyloxymethylene)triphenylphosphorane
15097-38-8

(carbobenzyloxymethylene)triphenylphosphorane

tert-butyl 3-(2-benzyloxy-2-oxo-ethylidene)azetidine-1-carboxylic acid

tert-butyl 3-(2-benzyloxy-2-oxo-ethylidene)azetidine-1-carboxylic acid

Conditions
ConditionsYield
In toluene for 2h; Reflux;100%
tert-butyl 3-oxoazetidine-1-carboxylate
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

(S)-1-amino-2-(methoxymethyl)pyrrolidine
59983-39-0

(S)-1-amino-2-(methoxymethyl)pyrrolidine

C14H25N3O3

C14H25N3O3

Conditions
ConditionsYield
at 55℃; for 16h;100%
tert-butyl 3-oxoazetidine-1-carboxylate
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

5-bromo-2,3-dihydro-1H-isoindole hydrochloride
919346-89-7

5-bromo-2,3-dihydro-1H-isoindole hydrochloride

tert-butyl-3-(5-bromoisoindolin-2-yl)azetidine-1-carboxylate

tert-butyl-3-(5-bromoisoindolin-2-yl)azetidine-1-carboxylate

Conditions
ConditionsYield
With acetic acid In methanol at 50℃; for 16h;100%
tert-butyl 3-oxoazetidine-1-carboxylate
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

diethyl 1-cyanomethylphosphonate
2537-48-6

diethyl 1-cyanomethylphosphonate

3-(cyanomethylene)azetidine-1-carboxylic acid tert-butyl ester
1153949-11-1

3-(cyanomethylene)azetidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: diethyl 1-cyanomethylphosphonate With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃;
Stage #2: tert-butyl 3-oxoazetidine-1-carboxylate In tetrahydrofuran; mineral oil Product distribution / selectivity;
99%
Stage #1: diethyl 1-cyanomethylphosphonate With sodium hydride In tetrahydrofuran at 0 - 20℃;
Stage #2: tert-butyl 3-oxoazetidine-1-carboxylate In tetrahydrofuran at 0℃;
Stage #3: With water In tetrahydrofuran
98%
Stage #1: diethyl 1-cyanomethylphosphonate With potassium tert-butylate In tetrahydrofuran at 0 - 30℃;
Stage #2: tert-butyl 3-oxoazetidine-1-carboxylate In tetrahydrofuran at 0 - 30℃;
95%
tert-butyl 3-oxoazetidine-1-carboxylate
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

methylmagnesium chloride
676-58-4

methylmagnesium chloride

tert-butyl 3-hydroxy-3-methylazetidine-1-carboxylate
1104083-23-9

tert-butyl 3-hydroxy-3-methylazetidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: tert-butyl 3-oxoazetidine-1-carboxylate; methylmagnesium chloride In tetrahydrofuran at 0℃; for 1h;
Stage #2: With water; ammonium chloride In tetrahydrofuran
99%
Stage #1: tert-butyl 3-oxoazetidine-1-carboxylate; methylmagnesium chloride In tetrahydrofuran at 0 - 20℃; for 6h;
Stage #2: With water; ammonium chloride In tetrahydrofuran at 0℃; for 0.166667h;
tert-butyl 3-oxoazetidine-1-carboxylate
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

tert-butyl 3-hydroxyazetidine-1-carboxylate
141699-55-0

tert-butyl 3-hydroxyazetidine-1-carboxylate

Conditions
ConditionsYield
With sodium tetrahydroborate; ethanol for 2h;99%
With sodium tetrahydroborate In tetrahydrofuran at 20℃; for 6h;84%
With methanol; sodium tetrahydroborate at 0 - 20℃; for 1h;
tert-butyl 3-oxoazetidine-1-carboxylate
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

3-methylene-azetidine-1-carboxylic acid tert-butyl ester
934664-41-2

3-methylene-azetidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With potassium tert-butylate; methyl-triphenylphosphonium iodide In diethyl ether at 35℃; for 2h;99%
tert-butyl 3-oxoazetidine-1-carboxylate
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

1-triphenylphosphoranylidene-2-propanone
1439-36-7

1-triphenylphosphoranylidene-2-propanone

tert-butyl 3-acetonylideneazetidine-1-carboxylate

tert-butyl 3-acetonylideneazetidine-1-carboxylate

Conditions
ConditionsYield
In toluene at 70℃; for 2h;99%
tert-butyl 3-oxoazetidine-1-carboxylate
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

nitromethane
75-52-5

nitromethane

3-hydroxy-3-(nitromethyl)azetidin-1-carboxylic acid tert-butyl ester
1008526-70-2

3-hydroxy-3-(nitromethyl)azetidin-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With triethylamine In ethanol at 20℃; for 16h; Inert atmosphere;98%
With triethylamine In ethanol at 20℃; for 16h;98%
triethylamine In ethanol for 18h;97%
tert-butyl 3-oxoazetidine-1-carboxylate
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

4-methoxybenzenesulfonyl hydrazide
1950-68-1

4-methoxybenzenesulfonyl hydrazide

tert-butyl 3-(2-((4-methoxyphenyl)sulfonyl)hydrazineylidene)azetidine-1-carboxylate
1510865-67-4

tert-butyl 3-(2-((4-methoxyphenyl)sulfonyl)hydrazineylidene)azetidine-1-carboxylate

Conditions
ConditionsYield
In toluene for 2h; Reflux;98%
In dimethylsulfoxide-d6 at 60℃; Schlenk technique;73%
tert-butyl 3-oxoazetidine-1-carboxylate
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

methyl iodide
74-88-4

methyl iodide

tert-butyl 3-methoxyazetidine-1-carboxylate
429669-07-8

tert-butyl 3-methoxyazetidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: tert-butyl 3-oxoazetidine-1-carboxylate With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere;
Stage #2: methyl iodide In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;
98%
azetidine
503-29-7

azetidine

tert-butyl 3-oxoazetidine-1-carboxylate
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

tert-butyl [1,3'-biazetidine]-1'-carboxylate

tert-butyl [1,3'-biazetidine]-1'-carboxylate

Conditions
ConditionsYield
Stage #1: azetidine; tert-butyl 3-oxoazetidine-1-carboxylate With acetic acid In 1,2-dichloro-ethane at 20℃;
Stage #2: With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane for 4h;
98%
tert-butyl 3-oxoazetidine-1-carboxylate
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

tert-butyl 3-ethyl-3-hydroxyazetidine-1-carboxylate
398489-28-6

tert-butyl 3-ethyl-3-hydroxyazetidine-1-carboxylate

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 20℃; for 5h; Inert atmosphere;98%
tert-butyl 3-oxoazetidine-1-carboxylate
398489-26-4

tert-butyl 3-oxoazetidine-1-carboxylate

4-Octyne
1942-45-6

4-Octyne

tert-butyl 3-oxo-4,5-dipropyl-3,6-dihydropyridine-1(2H)-carboxylate
1372173-47-1

tert-butyl 3-oxo-4,5-dipropyl-3,6-dihydropyridine-1(2H)-carboxylate

Conditions
ConditionsYield
With bis(1,5-cyclooctadiene)nickel (0); triphenylphosphine In toluene at 60℃; for 6h; Inert atmosphere; regioselective reaction;97%
With bis(1,5-cyclooctadiene)nickel (0); triphenylphosphine In toluene at 60℃; for 6h; Glovebox; Inert atmosphere;97%
With bis(triphenylphosphine)nickel(II) chloride; zinc In acetonitrile at 60℃; for 16h; Catalytic behavior; Reagent/catalyst; Solvent; Schlenk technique; Inert atmosphere;95%

398489-26-4Relevant articles and documents

Method for preparing aldehyde or ketone by oxidizing reaction alcohol oxide

-

Paragraph 0025-0036, (2021/11/03)

The invention relates to a method for preparing aldehyde or ketone by oxidizing reaction alcohol oxide. The invention belongs to the field of medicine and chemical engineering, and particularly relates to a nitric acid and organic nitrogen oxide composition as a catalyst. The invention is prepared by the oxidation reaction of alcohol, wherein the oxidant is oxygen, and the nitric acid and organic nitrogen oxide composition are used as a catalytic system. The reaction is homogeneous reaction, and the catalytic system is simplified. The method is simple and convenient to operate, high in yield and low in cost. The invention is a very economical and simple method for preparing aldehyde or ketone from alcohol, and is suitable for industrial production.

3-nitrile methylene azetidine-1-tert-butyl carbonate preparation method

-

Page/Page column 15; 17-19, (2020/02/06)

The invention discloses a 3-nitrile methylene azetidine-1-tert-butyl carbonate preparation method, which specifically comprises: 1, synthesizing 1-tert-butyl-3-glycolate; 2, synthesizing N-Boc-3-hydroxy azetidine through the 1-tert-butyl-3-glycolate obtained in the step 1; 3, synthesizing N-Boc-3-azetidinone through the N-Boc-3-hydroxy azetidinone obtained in the step 2; and 4, synthesizing 3-nitrile methylene azetidine-1-tert-butyl carbonate through the N-Boc-3-azetidinone obtained in the step 3. According to the preparation method disclosed by the invention, the existing conventional five-step synthesis process of 3-nitrile methylene azetidine-1-tert-butyl carbonate is reduced into three steps, so that the synthesis time is greatly saved, the emission of three-waste is reduced, and the process cost is reduced.

Preparation method of medicine intermediate 1 -tert-butoxycarbonyl -3 -azetidinone (by machine translation)

-

Paragraph 0081-0086, (2020/07/15)

The invention relates to the technical field of organic chemistry, and concretely relates 1 - tert-butyloxycarbonyl -3 -azetidinone and a preparation method thereof. Wherein R1 Is C1 - C6 Alkyl groups and R2 And R3 Is H or C1 - C6 The alkyl group and the acid are organic acids or inorganic acids. The method is high in relative yield and high in industrial amplification production applicability. (by machine translation)

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