Product Name

  • Name

    3-Azetidinecarboxylic acid

  • EINECS 674-976-7
  • CAS No. 36476-78-5
  • Article Data15
  • CAS DataBase
  • Density 1.275 g/cm3
  • Solubility Soluble in water.
  • Melting Point 286 °C (dec.)(lit.)
  • Formula C4H7NO2
  • Boiling Point 242 °C at 760 mmHg
  • Molecular Weight 101.105
  • Flash Point 100.1 °C
  • Transport Information
  • Appearance light yellow powder
  • Safety 24/25-22-36-26
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 36476-78-5 (3-Azetidinecarboxylic acid)
  • Hazard Symbols IrritantXi
  • Synonyms 3-Carboxyazetidine;Azetidine-3-carboxylic acid;
  • PSA 49.33000
  • LogP -0.38080

Synthetic route

N-benzyl azetidine-3-carboxylic acid
94985-27-0

N-benzyl azetidine-3-carboxylic acid

3-azetidinecarboxylic acid
36476-78-5

3-azetidinecarboxylic acid

Conditions
ConditionsYield
palladium In methanol90%
With hydrogen; palladium dihydroxide In methanol; water at 60℃; under 2068.59 Torr; for 16h;806.2 g
palladium In methanol
1-acetylazetidine-3-carboxylic acid
97628-91-6

1-acetylazetidine-3-carboxylic acid

3-azetidinecarboxylic acid
36476-78-5

3-azetidinecarboxylic acid

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In ethanol at 40℃; under 15001.5 Torr; for 24h;27.9%
1-nitrosoazetidine-3,3-dicarboxylic acid

1-nitrosoazetidine-3,3-dicarboxylic acid

3-azetidinecarboxylic acid
36476-78-5

3-azetidinecarboxylic acid

Conditions
ConditionsYield
With formic acid In water
N-benzyl-3,3-bis-(hydroxymethyl)-azetidine
26096-30-0

N-benzyl-3,3-bis-(hydroxymethyl)-azetidine

tartaric acid
87-69-4

tartaric acid

N-benzyl azetidine-3-carboxylic acid
94985-27-0

N-benzyl azetidine-3-carboxylic acid

3-azetidinecarboxylic acid
36476-78-5

3-azetidinecarboxylic acid

Conditions
ConditionsYield
With potassium hydroxide; phosphoric acid; ammonium formate; palladium on charcoal In methanol; water
...Expand
1-(t-butyloxycarbonyl)-azetidine-3-carboxylic acid
142253-55-2

1-(t-butyloxycarbonyl)-azetidine-3-carboxylic acid

3-azetidinecarboxylic acid
36476-78-5

3-azetidinecarboxylic acid

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In ethanol at 50℃; under 18751.9 Torr; for 30h;13.8 g
3-azetidinecarboxylic acid
36476-78-5

3-azetidinecarboxylic acid

benzyl chloroformate
501-53-1

benzyl chloroformate

1-benzyloxycarbonyl-3-azetidinecarboxylic acid
97628-92-7

1-benzyloxycarbonyl-3-azetidinecarboxylic acid

Conditions
ConditionsYield
Stage #1: 3-azetidinecarboxylic acid; benzyl chloroformate With sodium hydroxide In water at 0℃; for 16h;
Stage #2: With hydrogenchloride In water		100%
With potassium carbonate In water at 0 - 20℃;91%
Stage #1: 3-azetidinecarboxylic acid; benzyl chloroformate With potassium carbonate In 1,4-dioxane; water at 20℃; for 6h;
Stage #2: With piperazine In 1,4-dioxane; water for 0.5h;		83%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

3-azetidinecarboxylic acid
36476-78-5

3-azetidinecarboxylic acid

1-(t-butyloxycarbonyl)-azetidine-3-carboxylic acid
142253-55-2

1-(t-butyloxycarbonyl)-azetidine-3-carboxylic acid

Conditions
ConditionsYield
With triethylamine In methanol at 20℃; for 18h;100%
With triethylamine In methanol at 20℃; for 18h;100%
With sodium hydroxide In tetrahydrofuran; water at 20℃; for 24h; Product distribution / selectivity;95%
ethyl 6-chloro-5-cyano-2-(difluoromethyl)nicotinate
919354-88-4

ethyl 6-chloro-5-cyano-2-(difluoromethyl)nicotinate

3-azetidinecarboxylic acid
36476-78-5

3-azetidinecarboxylic acid

1-[3-cyano-6-(difluoromethyl)-5-(ethoxycarbonyl)pyridin-2-yl]azetidine-3-carboxylic acid
919354-92-0

1-[3-cyano-6-(difluoromethyl)-5-(ethoxycarbonyl)pyridin-2-yl]azetidine-3-carboxylic acid

Conditions
ConditionsYield
With triethylamine In ethanol; water at 120℃; for 0.166667h; Microwave irradiation;100%
3-azetidinecarboxylic acid
36476-78-5

3-azetidinecarboxylic acid

trifluoroacetic anhydride
407-25-0

trifluoroacetic anhydride

1-(trifluoroacetyl)azetidine-3-carboxylic acid
1001026-41-0

1-(trifluoroacetyl)azetidine-3-carboxylic acid

Conditions
ConditionsYield
at 0℃; for 3.33333h;100%
at 0℃; for 2.83333h;100%
methanol
67-56-1

methanol

3-azetidinecarboxylic acid
36476-78-5

3-azetidinecarboxylic acid

methyl 3-azetidinecarboxylate hydrochloride
100202-39-9

methyl 3-azetidinecarboxylate hydrochloride

Conditions
ConditionsYield
With thionyl chloride In acetonitrile at 0 - 20℃; for 2.33333h;100%
With thionyl chloride at 0 - 25℃; for 2.25h;100%
With thionyl chloride at 5 - 65℃;100%
methanol
67-56-1

methanol

3-azetidinecarboxylic acid
36476-78-5

3-azetidinecarboxylic acid

methyl azetidine-3-carboxylate
343238-58-4

methyl azetidine-3-carboxylate

Conditions
ConditionsYield
With thionyl chloride at 0 - 20℃; for 10h;100%
With chloro-trimethyl-silane Heating / reflux;
With chloro-trimethyl-silane Heating / reflux;
2-fluoro-4-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]-benzaldehyde

2-fluoro-4-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]-benzaldehyde

3-azetidinecarboxylic acid
36476-78-5

3-azetidinecarboxylic acid

1-{2-fluoro-4-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]-benzyl}-3-azetidine carboxylic acid

1-{2-fluoro-4-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]-benzyl}-3-azetidine carboxylic acid

Conditions
ConditionsYield
Stage #1: 2-fluoro-4-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]-benzaldehyde; 3-azetidinecarboxylic acid With acetic acid In tetrahydrofuran at 20℃; for 2h;
Stage #2: With methanol; sodium cyanoborohydride In tetrahydrofuran at 15 - 20℃; for 17h; Temperature; Concentration; Solvent;		92.6%
Stage #1: 2-fluoro-4-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]-benzaldehyde; 3-azetidinecarboxylic acid With acetic acid In methanol at 20℃; for 2h; Large scale;
Stage #2: With sodium cyanoborohydride In methanol at 20℃; for 17h; Large scale;		79%
Stage #1: 2-fluoro-4-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]-benzaldehyde; 3-azetidinecarboxylic acid With acetic acid In tetrahydrofuran; methanol at 20℃; for 2h;
Stage #2: With methanol; sodium cyanoborohydride In tetrahydrofuran at 20℃; for 16h;		2 g
4-[(1E)-1-([[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]imino)ethyl]-2-ethylbenzaldehyde
1230487-01-0

4-[(1E)-1-([[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]imino)ethyl]-2-ethylbenzaldehyde

3-azetidinecarboxylic acid
36476-78-5

3-azetidinecarboxylic acid

Siponimod
1230487-00-9

Siponimod

Conditions
ConditionsYield
Stage #1: 4-[(1E)-1-([[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]imino)ethyl]-2-ethylbenzaldehyde; 3-azetidinecarboxylic acid In methanol at 20 - 25℃; for 0.5h;
Stage #2: With methanol; sodium tris(acetoxy)borohydride		89%
Stage #1: 4-[(1E)-1-([[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]imino)ethyl]-2-ethylbenzaldehyde; 3-azetidinecarboxylic acid In methanol at 20 - 25℃; for 0.5h;
Stage #2: With sodium tris(acetoxy)borohydride In methanol Reagent/catalyst; Temperature;		89%
Stage #1: 4-[(1E)-1-([[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]imino)ethyl]-2-ethylbenzaldehyde; 3-azetidinecarboxylic acid With acetic acid In methanol at 20℃; for 0.333333h;
Stage #2: With sodium cyanoborohydride In methanol at 20℃;		20%
3-(3-(4-chloro-5-fluoropyrimidin-2-yl)-1-(2-fluorobenzyl)-1H-pyrazol-5-yl)isoxazole
1446358-48-0

3-(3-(4-chloro-5-fluoropyrimidin-2-yl)-1-(2-fluorobenzyl)-1H-pyrazol-5-yl)isoxazole

3-azetidinecarboxylic acid
36476-78-5

3-azetidinecarboxylic acid

C21H16F2N6O3

C21H16F2N6O3

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 75℃; for 18h;88%
2-(6-(3-(difluoromethoxy)-5-fluorophenyl)-1-((3-(trifluoromethyl)phenyl)sulfonyl)indolin-2-yl)acetic acid

2-(6-(3-(difluoromethoxy)-5-fluorophenyl)-1-((3-(trifluoromethyl)phenyl)sulfonyl)indolin-2-yl)acetic acid

3-azetidinecarboxylic acid
36476-78-5

3-azetidinecarboxylic acid

1-(2-(6-(3-(difluoromethoxy)-5-fluorophenyl)-1-((3-(trifluoromethyl)phenyl)sulfonyl)indolin-2-yl)acetyl)azetidine-3-carboxylic acid

1-(2-(6-(3-(difluoromethoxy)-5-fluorophenyl)-1-((3-(trifluoromethyl)phenyl)sulfonyl)indolin-2-yl)acetyl)azetidine-3-carboxylic acid

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 30℃;88%
N-butyl-2-fluoro-N-(5-(4-formylphenyl)-1,3,4-thiadiazol-2-yl)benzamide
1220708-88-2

N-butyl-2-fluoro-N-(5-(4-formylphenyl)-1,3,4-thiadiazol-2-yl)benzamide

3-azetidinecarboxylic acid
36476-78-5

3-azetidinecarboxylic acid

1-(4-(5-(N-butyl-2-fluorobenzamido)-1,3,4-thiadiazol-2-yl)benzyl)azetidine-3-carboxylic acid
1220709-59-0

1-(4-(5-(N-butyl-2-fluorobenzamido)-1,3,4-thiadiazol-2-yl)benzyl)azetidine-3-carboxylic acid

Conditions
ConditionsYield
Stage #1: N-butyl-2-fluoro-N-(5-(4-formylphenyl)-1,3,4-thiadiazol-2-yl)benzamide; 3-azetidinecarboxylic acid With acetic acid In methanol at 20℃; for 1h;
Stage #2: With methanol; sodium cyanoborohydride at 20℃;
Stage #3: With acetic acid In methanol pH=3 - 4;		87%
Stage #1: N-butyl-2-fluoro-N-(5-(4-formylphenyl)-1,3,4-thiadiazol-2-yl)benzamide; 3-azetidinecarboxylic acid With acetic acid In methanol at 20℃; for 1h;
Stage #2: With sodium cyanoborohydride In methanol at 20℃;		87%
6-(2,3-dihydro-1H-inden-2-ylmethoxy)-1-methyl-3,4-dihydro-2-naphthalenecarbaldehyde

6-(2,3-dihydro-1H-inden-2-ylmethoxy)-1-methyl-3,4-dihydro-2-naphthalenecarbaldehyde

3-azetidinecarboxylic acid
36476-78-5

3-azetidinecarboxylic acid

1-{[6-(2,3-dihydro-1H-inden-2-ylmethoxy)-1-methyl-3,4-dihydro-2-naphthalenyl]methyl}-3-azetidinecarboxylic acid hydrochloride
847585-32-4

1-{[6-(2,3-dihydro-1H-inden-2-ylmethoxy)-1-methyl-3,4-dihydro-2-naphthalenyl]methyl}-3-azetidinecarboxylic acid hydrochloride

Conditions
ConditionsYield
Stage #1: 6-(2,3-dihydro-1H-inden-2-ylmethoxy)-1-methyl-3,4-dihydro-2-naphthalenecarbaldehyde; 3-azetidinecarboxylic acid With sodium hydroxide; trimethyl orthoformate In tetrahydrofuran; methanol at 0℃; for 4h;
Stage #2: With sodium tetrahydroborate In tetrahydrofuran; methanol at 0℃; for 0.5h;
Stage #3: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 0.5h;		87%
3-azetidinecarboxylic acid
36476-78-5

3-azetidinecarboxylic acid

2,2,2-Trichloroethyl chloroformate
17341-93-4

2,2,2-Trichloroethyl chloroformate

1-((2,2,2-trichloroethoxy)carbonyl)azetidine-3-carboxylic acid

1-((2,2,2-trichloroethoxy)carbonyl)azetidine-3-carboxylic acid

Conditions
ConditionsYield
Stage #1: 3-azetidinecarboxylic acid With sodium hydroxide In water at -10℃;
Stage #2: 2,2,2-Trichloroethyl chloroformate In water at -10 - 24℃; for 3h;		87%
3-azetidinecarboxylic acid
36476-78-5

3-azetidinecarboxylic acid

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

1-(4-methoxy-benzyl)-azetidine-3-carboxylic acid
1127402-49-6

1-(4-methoxy-benzyl)-azetidine-3-carboxylic acid

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 1034.32 Torr;85%
With palladium 10% on activated carbon; hydrogen In methanol at 25℃; under 760.051 Torr; for 1h;82%
3-azetidinecarboxylic acid
36476-78-5

3-azetidinecarboxylic acid

acetone
67-64-1

acetone

1-isopropyl-azetidine-3-carboxylic acid
959238-28-9

1-isopropyl-azetidine-3-carboxylic acid

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 1034.32 Torr;85%
4-(5-(4-(2-fluoroethoxy)phenyl)-1,2,4-oxadiazol-3-yl)benzaldehyde

4-(5-(4-(2-fluoroethoxy)phenyl)-1,2,4-oxadiazol-3-yl)benzaldehyde

3-azetidinecarboxylic acid
36476-78-5

3-azetidinecarboxylic acid

1-(4-(5-(4-(2-fluoroethoxy)phenyl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylic acid

1-(4-(5-(4-(2-fluoroethoxy)phenyl)-1,2,4-oxadiazol-3-yl)benzyl)azetidine-3-carboxylic acid

Conditions
ConditionsYield
Stage #1: 4-(5-(4-(2-fluoroethoxy)phenyl)-1,2,4-oxadiazol-3-yl)benzaldehyde; 3-azetidinecarboxylic acid With acetic acid In methanol for 0.5h;
Stage #2: With sodium cyanoborohydride In methanol		85%
ethyl 6-chloro-5-cyano-2-(trifluoromethyl)nicotinate
175277-73-3

ethyl 6-chloro-5-cyano-2-(trifluoromethyl)nicotinate

3-azetidinecarboxylic acid
36476-78-5

3-azetidinecarboxylic acid

1-[3-cyano-5-(ethoxycarbonyl)-6-(trifluoromethyl)pyridin-2-yl]azetidine-3-carboxylic acid
919354-83-9

1-[3-cyano-5-(ethoxycarbonyl)-6-(trifluoromethyl)pyridin-2-yl]azetidine-3-carboxylic acid

Conditions
ConditionsYield
With triethylamine In ethanol for 0.333333h; Microwave irradiation;84%
With triethylamine In ethanol for 0.333333h; Microwave irradiation;84%
4-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]-benzaldehyde
635701-88-1

4-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]-benzaldehyde

3-azetidinecarboxylic acid
36476-78-5

3-azetidinecarboxylic acid

1-{4-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]-benzyl}-3-azetidine carboxylic acid

1-{4-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]-benzyl}-3-azetidine carboxylic acid

Conditions
ConditionsYield
Stage #1: 4-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]-benzaldehyde; 3-azetidinecarboxylic acid With acetic acid In tetrahydrofuran; methanol at 20℃; for 2h;
Stage #2: With sodium cyanoborohydride In tetrahydrofuran; methanol at 20℃; for 16h;		82%
Stage #1: 4-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]-benzaldehyde; 3-azetidinecarboxylic acid With acetic acid In methanol at 20℃; for 0.333333h;
Stage #2: With sodium cyanoborohydride In methanol for 1h;		74%
Stage #1: 4-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]-benzaldehyde; 3-azetidinecarboxylic acid With acetic acid In methanol at 20℃; for 0.333333h;
Stage #2: With sodium cyanoborohydride In methanol for 1h;		74%
Stage #1: 4-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]-benzaldehyde; 3-azetidinecarboxylic acid With acetic acid In methanol at 20℃; for 0.333333h;
Stage #2: With sodium cyanoborohydride In methanol for 1h;		74%
N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-6-(1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide
1396776-39-8

N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-6-(1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

3-azetidinecarboxylic acid
36476-78-5

3-azetidinecarboxylic acid

6-(1-(azetidine-3-carbonyl)-1,2,3,6-tetrahydropyridin-4-yl)-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxamide
1396772-06-7

6-(1-(azetidine-3-carbonyl)-1,2,3,6-tetrahydropyridin-4-yl)-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Conditions
ConditionsYield
Stage #1: N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-6-(1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide; 3-azetidinecarboxylic acid With triethylamine In dimethyl sulfoxide at 20℃; for 0.25h;
Stage #2: With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In dimethyl sulfoxide		81.9%

3-Azetidinecarboxylic acid Chemical Properties

IUPAC Name: azetidine-3-carboxylic acid 
Empirical Formula: C4H7NO2
Molecular Weight: 101.1039g/mol
Structure of 3-Azetidinecarboxylic acid (CAS NO.36476-78-5):

Index of Refraction: 1.499
Molar Refractivity: 23.29 cm3
Molar Volume: 79.2 cm3
Polarizability: 9.23×10-24cm3
Surface Tension: 48.2 dyne/cm
Density: 1.275 g/cm3
Flash Point: 100.1 °C
Enthalpy of Vaporization: 52.75 kJ/mol 
Melting Point: 286 °C (dec.)(lit.)
Boiling Point: 242 °C at 760 mmHg
Vapour Pressure: 0.0116 mmHg at 25°C 
Product Categories: Pharmaceutical Raw Materials;Unusual amino acids;Heterocycles series;Miscellaneous;Carboxylic Acids;Amino Acids 13C, 2H, 15N;Azetidines;Simple 4-Membered Ring Compounds;Peptide;Amino Acids & Derivatives;Carboxylic Acids;Ring Systems;Alicyclic Amino Acids;Peptide Synthesis;Unnatural Amino Acid Derivatives;B-Amino 
Canonical SMILES: C1C(CN1)C(=O)O
InChI: InChI=1S/C4H7NO2/c6-4(7)3-1-5-2-3/h3,5H,1-2H2,(H,6,7)
InChIKey: GFZWHAAOIVMHOI-UHFFFAOYSA-N

3-Azetidinecarboxylic acid Uses

A useful intermediate in the synthesis of polypeptides.

3-Azetidinecarboxylic acid Toxicity Data With Reference

1.    

orl-rat LD50:>5 g/kg

     FMCHA2    Farm Chemicals Handbook .(Meister Publishing,Willoughy, OH.: )1991,C65.
2.    

skn-rbt LD50:>1 g/kg

     FMCHA2    Farm Chemicals Handbook .(Meister Publishing,Willoughy, OH.: )1991,C65.

3-Azetidinecarboxylic acid Safety Profile

Low toxicity by ingestion and skin contact. When heated to decomposition it emits toxic vapors of NOx.
Hazard Codes:  Xi
The Risk Statements information of  3-AZETIDINECARBOXYLIC ACID:
36/37/38:  Irritating to eyes, respiratory system and skin 
The Safety Statements information of  3-AZETIDINECARBOXYLIC ACID :
22:  Do not breathe dust 
26:  In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 
36:  Wear suitable protective clothing 
24/25:  Avoid contact with skin and eyes 
WGK Germany:3
Hazard Note:Irritant

3-Azetidinecarboxylic acid Specification

  3-Azetidinecarboxylic acid , its cas register number is 36476-78-5. It also can be called 3-Carboxyazetidine ; 5-22-01-00023 (Beilstein Handbook Reference) ; Azetidine-3-carboxylic acid ; CHA-811 ; Caswell No. 063C ; EPA Pesticide Chemical Code 128830 . 3-Azetidinecarboxylic acid (CAS NO.36476-78-5) is a light yellow powder.

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