CAS No.72776-05-7,(S)-BENZYL 2-AZETIDINONE-4-CARBOXYLATE Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	72776-05-7
Name:	(S)-BENZYL 2-AZETIDINONE-4-CARBOXYLATE
Article Data:	17

Formula:	C11H11 N O3
Molecular Weight:	205.213
Synonyms:	2-Azetidinecarboxylicacid, 4-oxo-, phenylmethyl ester, (S)-; Benzyl (S)-4-oxo-2-azetidinecarboxylate
Density:	1.268 g/cm³
Melting Point:	137-140 °C(lit.)
Boiling Point:	404.7 °C at 760 mmHg
Flash Point:	198.5 °C
Solubility:	Soluble in water
Appearance:	white to light yellow crystalline powder
Safety:	24/25
PSA:	55.40000
LogP:	0.94710

Synthetic route

: 2791-79-9
dibenzyl L-aspartate

: 72776-05-7
(S)-benzyl 4-oxoazetidine-2-carboxylate

Conditions

Conditions	Yield
Stage #1: dibenzyl L-aspartate With chloro-trimethyl-silane; triethylamine In diethyl ether at 0℃; for 1h; Stage #2: With tert-butylmagnesium chloride In diethyl ether at -5 - 0℃; for 2h;	47%
Stage #1: dibenzyl L-aspartate With chloro-trimethyl-silane In diethyl ether at -78 - 25℃; Stage #2: With tert-butylmagnesium bromide In diethyl ether at -78 - 25℃;	40%
With chloro-trimethyl-silane; tert-butylmagnesium chloride

: 72776-06-8
(L)-N-(trimethylsilyl)dibenzyl aspartate

: 72776-05-7
(S)-benzyl 4-oxoazetidine-2-carboxylate

Conditions

Conditions	Yield
With tert-butylmagnesium chloride In diethyl ether at 0℃; Yield given;
With tert-butylmagnesium chloride 1.) 0 deg C, 2.) room temperature, overnight; Yield given;
With tert-butylmagnesium chloride In diethyl ether at 0℃;
With tert-butylmagnesium chloride In diethyl ether at -5 - 20℃; for 12.5h;	5.1 g

: 4079-59-8
D-aspartic acid dibenzyl ester

: 72776-05-7
(S)-benzyl 4-oxoazetidine-2-carboxylate

Conditions

Conditions	Yield
With chloro-trimethyl-silane; tert-butylmagnesium bromide; triethylamine Yield given. Multistep reaction;

: 2791-79-9
dibenzyl L-aspartate

methoxy poly(ethylene glycol) sodium salt: methoxy poly(ethylene glycol) sodium salt

: 72776-05-7
(S)-benzyl 4-oxoazetidine-2-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: TEA; 4-dimethylaminopyridine / diethyl ether / 3 h / 0 °C 2: 5.1 g / tBuMgCl / diethyl ether / 12.5 h / -5 - 20 °C View Scheme

: C16H21NO5

: 72776-05-7
(S)-benzyl 4-oxoazetidine-2-carboxylate

Conditions

Conditions	Yield
With cytochrome P411 expressed in Escherichia coli In aq. phosphate buffer at 20℃; for 24h; pH=8; Catalytic behavior; Enzymatic reaction; enantioselective reaction;	n/a

: 72776-05-7
(S)-benzyl 4-oxoazetidine-2-carboxylate

: 72776-07-9
(S)-4-(hydroxymethyl)-2-azetidinone

Conditions

Conditions	Yield
With sodium tetrahydroborate In methanol at 0 - 20℃; Inert atmosphere;	100%
With sodium tetrahydroborate In methanol	71%
With sodium tetrahydroborate In methanol
With lithium borohydride

: 72776-05-7
(S)-benzyl 4-oxoazetidine-2-carboxylate

α-benzyl-L-aspartic acid poly(β-peptide); Monomer(s): α-benzyl-L-aspartic acid β-lactam: α-benzyl-L-aspartic acid poly(β-peptide); Monomer(s): α-benzyl-L-aspartic acid β-lactam

Conditions

Conditions	Yield
With magnesium bis(hexamethyldisilazide) In dichloromethane for 0.2h; Product distribution; Further Variations:; Reagents; Solvents; concentrations;	100%
With magnesium bis(hexamethyldisilazide) In dichloromethane for 0.2h;	100%

: 72776-05-7
(S)-benzyl 4-oxoazetidine-2-carboxylate

: 16404-94-7
(S)-4-oxo-azetidine-2-carboxylic acid

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In tetrahydrofuran for 14h;	98%
With hydrogen; palladium 10% on activated carbon In methanol at 25℃; under 760.051 Torr; for 0.5h;	93%
With hydrogen; palladium on activated charcoal In isopropyl alcohol at 20℃; under 1140.08 Torr; for 0.333333h;	85%
With hydrogen; palladium on activated charcoal In tetrahydrofuran at 25℃; for 0.75h;	11.8 g

: 72776-05-7
(S)-benzyl 4-oxoazetidine-2-carboxylate

: 18162-48-6
tert-butyldimethylsilyl chloride

: 82938-49-6
(S)-benzyl-1-(tert-butyldimethylsilyl)-4-oxoazetidine-2-carboxylate

Conditions

Conditions	Yield
With triethylamine	98%
With triethylamine	97%
With triethylamine In N,N-dimethyl-formamide	93%

: 72776-05-7
(S)-benzyl 4-oxoazetidine-2-carboxylate

: 372515-10-1
(S)-4-Oxo-azetidine-2-carboxylic acid 2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethyl ester

α-3,6,9,12-tetraoxatridecyl-L-aspartic acid, α-benzyl-L-aspartic acid diblock copoly(β-peptide); Monomer(s): α-3,6,9,12-tetraoxatridecyl-L-aspartic acid β-lactam; α-benzyl-L-aspartic acid β-lactam: α-3,6,9,12-tetraoxatridecyl-L-aspartic acid, α-benzyl-L-aspartic acid diblock copoly(β-peptide); Monomer(s): α-3,6,9,12-tetraoxatridecyl-L-aspartic acid β-lactam; α-benzyl-L-aspartic acid β-lactam

Conditions

Conditions	Yield
With tris(bistrimethylsilylamine)scandium(III) In dichloromethane at 20℃;	95%

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Chemistry

IUPAC Name: Benzyl (2S)-4-oxoazetidine-2-carboxylate
Synonyms of (S)-Benzyl 2-azetidinone-4-carboxylate (CAS NO.72776-05-7): Benzyl (2S)-4-oxoazetidine-2-carboxylate ; Benzyl (S)-4-oxo-2-azetidinecarboxylate
CAS NO: 72776-05-7
Molecular Formula: C₁₁H₁₁NO₃
Molecular Weight: 205.21
Molecular Structure:
H bond acceptors: 4
H bond donors: 1
Freely Rotating Bonds: 4
Polar Surface Area: 46.61 Å²
Index of Refraction: 1.565
Molar Refractivity: 52.75 cm³
Molar Volume: 161.8 cm³
Surface Tension: 50.4 dyne/cm
Density: 1.268 g/cm³
Flash Point: 198.5 °C
Enthalpy of Vaporization: 65.62 kJ/mol
Boiling Point: 404.7 °C at 760 mmHg
Vapour Pressure: 9.28E-07 mmHg at 25°C
Melting Point: 1137-140 °C(lit.)
Alpha : -42.5 º (C=3, CHCL3)
Storage temp: 0-6°C
Appearance: (S)-Benzyl 2-azetidinone-4-carboxylate (CAS NO.72776-05-7) is white to light yellow crystal powder.
SMILES: O=C(OCc1ccccc1)[C@H]2NC(=O)C2
InChI: InChI=1/C11H11NO3/c13-10-6-9(12-10)11(14)15-7-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,12,13)/t9-/m0/s1
InChIKey: WGLLBHSIXLWVFU-VIFPVBQEBT
Std. InChI: InChI=1S/C11H11NO3/c13-10-6-9(12-10)11(14)15-7-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,12,13)/t9-/m0/s1
Std. InChIKey: WGLLBHSIXLWVFU-VIFPVBQESA-N
Product Categories: chiral;Chiral Building Blocks;Lactams;Organic Building Blocks

Safety Profile

Safety Statements: 24/25
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3

Specification

General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam.
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage: Store (S)-Benzyl 2-azetidinone-4-carboxylate (CAS NO.72776-05-7) in a cool, dry place. Store in a tightly closed container. Keep refrigerated. (Store below 4°C/39°F.) Store protected from light.