L(-)-Pipecolinic acid supplier

Name
L(-)-Pipecolinic acid
EINECS 221-462-1
CAS No. 3105-95-1
Article Data61
CAS DataBase
Density 1.125 g/cm³
Solubility Soluble in water
Melting Point 272 °C(lit.)
Formula C₆H₁₁NO₂
Boiling Point 265.766 °C at 760 mmHg
Molecular Weight 129.159
Flash Point 114.532 °C
Transport Information
Appearance white to light yellow crystal powder
Safety 26-36-24/25
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 2-Piperidinecarboxylicacid, (S)-;Pipecolic acid, (S)-(-)- (8CI);(-)-Pipecolic acid;(S)-(-)-2-Piperidinecarboxylic acid;(S)-(-)-Pipecolic acid;(S)-Pipecolinic acid;(S)-Piperidine-2-carboxylic acid;L-Piperidine-2-carboxylic acid;NSC 93089;
PSA 49.33000
LogP 0.54190

Synthetic route

: 923-27-3
D-lysine

: 3105-95-1
pipecolinic acid

Conditions

Conditions	Yield
With porcine kidney D-amino acid oxidase; Pseudomonas putida N-methyl-L-amino acid dehydrogenase; Tris buffer; flavin adenine dinucleotide; catalase In various solvent(s) at 30℃; for 24h; pH=5.1 - 7.6;	100%

: 123495-48-7
(S)-(-)-2-piperidinecarboxylic acid ethyl ester hydrochloride

: 3105-95-1
pipecolinic acid

Conditions

Conditions	Yield
With hydrogenchloride; water at 90℃; for 6h;	100%

: 28697-11-2
(S)-1-(carbobenzyloxy)-2-piperidinecarboxylic acid

: 3105-95-1
pipecolinic acid

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol under 2327.2 Torr; for 6h; Ambient temperature;	94%

: C16H26N2O3S

: 3105-95-1
pipecolinic acid

Conditions

Conditions	Yield
With lithium hydroxide In tetrahydrofuran at 0℃; for 3h; Reagent/catalyst;	93.2%

: 290333-69-6
(4S,9aS)-4-phenylhexahydropyrido[2,1-c][1,4]oxazin-1-one

: 3105-95-1
pipecolinic acid

Conditions

Conditions	Yield
With hydrogen; palladium dihydroxide In ethanol for 2h; Catalytic hydrogenation;	91%

: 35677-83-9, 41994-45-0, 43041-11-8, 90710-04-6
methyl (S)-pipecolinate

: 3105-95-1
pipecolinic acid

Conditions

Conditions	Yield
With sodium hydroxide at 120℃; for 3h;	91%

: 56-87-1
L-lysine

: 3105-95-1
pipecolinic acid

Conditions

Conditions	Yield
With bovine liver catalase; D-glucose; NADP In water at 30℃; for 17h; pH=7.5;	90%
platinum(IV) oxide; Pt/titania In water for 44h; Irradiation; pH 9.7;	33%
With lysine aminotransferase expressed by Escherichia coli JM109

: C6H10N2

: 3105-95-1
pipecolinic acid

Conditions

Conditions	Yield
With water; hydrogen bromide at 70℃; for 5h; Reagent/catalyst; Temperature;	90%

: 56099-73-1
(2S)-1-(4-methylphenylsulfonyl)piperidine-2-carboxylic acid

: 3105-95-1
pipecolinic acid

Conditions

Conditions	Yield
With sodium amalgam; sodium phosphate In methanol at 20℃; for 5h;	80%

: 500131-75-9
(4R)-4-Phenylhexahydropyrido<2,1-c><1,4>oxazin-1-one

: 3105-95-1
pipecolinic acid

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol; acetic acid for 1h;	70%

: 15912-30-8, 35677-82-8, 98626-57-4, 109731-18-2, 111478-73-0, 112797-03-2, 128684-94-6, 138804-98-5
(2S)-2-piperidinecarboxylic acid L-tartrate

: 3105-95-1
pipecolinic acid

Conditions

Conditions	Yield
With Amberlite IR-120 In water	59%

: 4043-87-2
pipecolic Acid

: 3105-95-1
pipecolinic acid

Conditions

Conditions	Yield
With porcine kidney D-amino acid oxidase; Pseudomonas putida N-methyl-L-amino acid dehydrogenase; Tris buffer; flavin adenine dinucleotide; catalase In various solvent(s) at 30℃; for 24h; pH=8.0;	50%
With D-tartaric acid

: 625824-32-0
(3S,5S)-2,3,5,6-tetrahydro-3-(4-bromobutyl)-5-phenyl-N-(benzyloxycarbonyl)-4H-1,4-oxazine-2-one

A: 327-57-1
L-Norleucine

B: 3105-95-1
pipecolinic acid

Conditions

Conditions	Yield
With hydrogen; trifluoroacetic acid; palladium on activated charcoal In methanol under 2844.31 Torr; for 24h;	A 12% B 45%

: 227185-30-0
N-acetyl-DL-2-amino-6-bromohexanoic acid

A: 3105-95-1
pipecolinic acid

B: 849758-49-2
N-acetyl-D-2-amino-6-bromohexanoic acid

C: N-acetyl-L-2-amino-6-bromohexanoic acid

Conditions

Conditions	Yield
With sodium hydroxide; Aspergillus L-aminoacylase; cobalt(II) chloride In water at 38℃; for 24h; pH=7;	A 35% B n/a C n/a

...Expand

: 19889-77-1
(RS)-piperidine-2-carboxamide

: 3105-95-1
pipecolinic acid

Conditions

Conditions	Yield
With air; D-glucose; Pseudomonas fluorescens DSM 9924 cells; yeast extract at 30℃;	20%

: 117614-90-1
(2S,3'S,5'R,6'R)-6'-(3-Carboxy-propyl)-[2,3']bipiperidinyl-5'-carboxylic acid

A: 3105-95-1
pipecolinic acid

B: 107-95-9
3-amino propanoic acid

C: 56-12-2
4-amino-n-butyric acid

Conditions

Conditions	Yield
With chromium(VI) oxide In sulfuric acid at 100℃; for 6h;	A 9% B n/a C n/a

...Expand

: 31456-71-0
(2S)-1,2,3,6-tetrahydropyridine-2-carboxylic acid

: 3105-95-1
pipecolinic acid

Conditions

Conditions	Yield
With methanol; platinum Hydrogenation;

: 98-98-6
2-Picolinic acid

A: 3105-95-1
pipecolinic acid

B: 1723-00-8
(R)-(+)-pipecolic acid

Conditions

Conditions	Yield
With hydrogen

: 692-04-6
H-Lys(acetyl)-OH

: 3105-95-1
pipecolinic acid

Conditions

Conditions	Yield
platinum(IV) oxide; Pt/titania In water for 24h; Irradiation; pH 5.8;	17 % Chromat.

: 156-86-5
L-homoarginine

: 3105-95-1
pipecolinic acid

Conditions

Conditions	Yield
platinum(IV) oxide; Pt/titania In water for 24h; Irradiation; pH 5.7;	43 % Chromat.

: 1190-49-4, 121080-96-4
N-6-(aminocarbonyl)-L-lysine

: 3105-95-1
pipecolinic acid

Conditions

Conditions	Yield
platinum(IV) oxide; Pt/titania In water for 17h; Irradiation; pH 7.3;	38 % Chromat.

: 2418-95-3
(S)-2-amino-6-(tert-butoxycarbonylamino)hexanoic acid

: 3105-95-1
pipecolinic acid

Conditions

Conditions	Yield
platinum(IV) oxide; Pt/titania In water for 41h; Irradiation; pH 4.6;	11 % Chromat.

: 1190-48-3
Nε-formyl-(2S)-lysine

: 3105-95-1
pipecolinic acid

Conditions

Conditions	Yield
platinum(IV) oxide; Pt/titania In water for 47h; Irradiation; pH 6.6;	8 % Chromat.

: 657-27-2, 10098-89-2
L-Lysine hydrochloride

: 3105-95-1
pipecolinic acid

Conditions

Conditions	Yield
With sodium nitroprusside; sodium hydroxide In water at 60℃; for 4h; pH=9.5; Yield given;
at 37℃; for 20h; pH=7; Enzymatic reaction;	n/a

: 104987-11-3
Tacrolimus

: 3105-95-1
pipecolinic acid

Conditions

Conditions	Yield
With hydrogenchloride Heating;

: 53123-88-9
(22E,24E,26E,27E,29R,30S,31R,32R,34S,36S,38S,39S,40S,41R,50R)-40,50-dihydroxy-39-[(1R)-2-[(1S,3R,4R)-4-hydroxy-3-methoxy-cyclohexyl]-1-methyl-ethyl]-38,41-dimethoxy-29,30,31,32,42,43-hexamethyl-60,61-dioxa-51-azatricyclohexatriaconta-22,24,26(42),27(43)-tetraene-44,45,46,47,48-pentone

: 3105-95-1
pipecolinic acid

Conditions

Conditions	Yield
With hydrogenchloride In methanol for 32h;

: 32559-18-5
methyl piperidine-2-carboxylate hydrochloride

A: 3105-95-1
pipecolinic acid

B: 1723-00-8
(R)-(+)-pipecolic acid

Conditions

Conditions	Yield
With Aspergillus niger lipase Product distribution; enantioselectivity, different pH, enzyme assay, other pipecolate esters;

: 56879-47-1, 112241-70-0, 119593-44-1, 122088-79-3
(2R,3R)-3-hydroxypiperidine-1-carboxylic acis

: 3105-95-1
pipecolinic acid

Conditions

Conditions	Yield
With phosphorus; hydrogen iodide at 140℃; for 5h;

: n-octyl 2-piperidinecarboxylate hydrochloride

A: (R)-Octyl-2-pipecolate hydrochloride

B: 3105-95-1
pipecolinic acid

Conditions

Conditions	Yield
Aspergillus niger lipase for 3h;

: 50-00-0
formaldehyd

: 3105-95-1
pipecolinic acid

: 41447-18-1
(-)-(2S)-1-methylpiperidine-2-carboxylic acid

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In methanol under 836.056 Torr; for 24h;	100%
With hydrogen; palladium on activated charcoal In methanol; water for 42h;

: 1217-89-6
1-benzylisatin

: 13672-24-7
ethyl (2E)-(1-benzyl-2-oxo-1,2-dihydro-3H-indol-3-ylidene)acetate

: 3105-95-1
pipecolinic acid

: C39H37N3O4

Conditions

Conditions	Yield
In ethanol at 20℃; for 2h; diastereoselective reaction;	99%

...Expand

: 24424-99-5
di-tert-butyl dicarbonate

: 3105-95-1
pipecolinic acid

: 26250-84-0
(S)-(-)-1-(tert-butoxycarbonyl)-2-piperidinecarboxylic acid

Conditions

Conditions	Yield
With TEA In methanol a) 50 deg C, 5 min, b) RT, 1 h;	98%
	95%
With sodium hydrogencarbonate In tetrahydrofuran; water at 25℃; Inert atmosphere;	95.8%

: 67-56-1
methanol

: 3105-95-1
pipecolinic acid

: 18650-39-0
(S)-methyl pipecolinate hydrochloride

Conditions

Conditions	Yield
With thionyl chloride at 20℃; for 48h;	97.5%
With thionyl chloride at 0 - 20℃; for 10.58h;	95%
With thionyl chloride at 0 - 20℃;	92%

: 79-22-1
methyl chloroformate

: 3105-95-1
pipecolinic acid

: 216301-92-7
(S)-(-)-[(N-methoxycarbonyl)piperidine]-2-carboxylic acid

Conditions

Conditions	Yield
With sodium hydroxide In water at 20℃; pH=8 - 9; Acylation;	97%
With sodium hydroxide In water	66%
With sodium hydroxide In water	66%

: 123-72-8
butyraldehyde

: 3105-95-1
pipecolinic acid

: (2S)-1-butylpiperidine-2-carboxylic acid

Conditions

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In ethanol at 20℃; Solvent; Reagent/catalyst;	96.8%
Stage #1: butyraldehyde; pipecolinic acid With trifluoroacetic acid In methanol at 20℃; for 1h; Stage #2: With sodium cyanoborohydride In methanol at 30 - 40℃; for 6h; Reagent/catalyst; Concentration;	65%

: 3105-95-1
pipecolinic acid

: 741633-48-7
(S)-Piperidine-2-carbonyl chloride

Conditions

Conditions	Yield
With thionyl chloride In ethanol	95%
Multi-step reaction with 2 steps 1: NaOH / H2O / 0 °C 2: SOCl2 / CH2Cl2 / 24 h / Ambient temperature View Scheme
Stage #1: pipecolinic acid With thionyl chloride In methanol at -20℃; Reflux; Stage #2: With triethylamine In ethyl acetate at 20℃;
With thionyl chloride In dichloromethane at 20℃;

: 3105-95-1
pipecolinic acid

: 41373-39-1
(S)-pipecolinol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 14h; Reflux; Inert atmosphere;	95%
With lithium aluminium tetrahydride In tetrahydrofuran for 8h; Reflux;	90%
Stage #1: pipecolinic acid With dimethylsulfide borane complex; boron trifluoride diethyl etherate In tetrahydrofuran at 0℃; Reflux; Stage #2: With hydrogenchloride; methanol In water at 0℃; Reflux;	80%

: 64-17-5
ethanol

: 3105-95-1
pipecolinic acid

: 22328-78-5
(S)-piperidine-2-carboxylic acid ethyl ester

Conditions

Conditions	Yield
Stage #1: pipecolinic acid With thionyl chloride at 20 - 23℃; for 16h; Inert atmosphere; Stage #2: ethanol for 6h; Inert atmosphere;	95%
With thionyl chloride for 4h; Reflux;	90%
With thionyl chloride at 70℃; for 12h;

: 50-00-0
formaldehyd

: C36H36O20S4(4-)*4Na(1+)

: 3105-95-1
pipecolinic acid

: C64H80N4O28S4(4-)*4Na(1+)

Conditions

Conditions	Yield
In water at 20℃; for 336h; Inert atmosphere;	95%

...Expand

: (η6-p-cymene)Ru(acetylacetonate)chloride

: 3105-95-1
pipecolinic acid

: [R(Ru)S(C), S(Ru)S(C)]-[(η6-p-cymene)Ru[(L)-2-piperidinecarboxylato]chloride] hydrate

Conditions

Conditions	Yield
In methanol mixed, stirred for 2 h, filtered, evaptd.(vac.), redissolved, pptd.(diethylether), filtered off, washed(diethylether), dried(vac.); elem. anal.;	94%

: 59938-06-6
(E)-4-Ethoxy-1,1,1-trifluoro-3-buten-2-one

: 3105-95-1
pipecolinic acid

: (S)-1-(E)-(4,4,4-trifluoro-3-oxo-1-butenyl)piperidine-2-carboxylic acid

Conditions

Conditions	Yield
Stage #1: (E)-4-Ethoxy-1,1,1-trifluoro-3-buten-2-one; pipecolinic acid With sodium hydrogencarbonate In water Stage #2: Acidic conditions;	91%

: 6066-82-6
1-hydroxy-pyrrolidine-2,5-dione

: 3105-95-1
pipecolinic acid

: (S)-Piperidine-2-carboxylic acid 2,5-dioxo-pyrrolidin-1-yl ester

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In dichloromethane	90%

: 501-53-1
benzyl chloroformate

: 3105-95-1
pipecolinic acid

: 28697-11-2
(S)-1-(carbobenzyloxy)-2-piperidinecarboxylic acid

Conditions

Conditions	Yield
With sodium carbonate In 1,3-dioxane; water	89%
With sodium carbonate In 1,4-dioxane; water	89%
With sodium hydroxide for 6h; Ambient temperature;
With sodium hydroxide In tetrahydrofuran; water at 20℃; for 4h;
With sodium hydroxide In water at 0℃; for 4h;

: 1228538-77-9
6,8-dichloro-3-nitro-2-phenyl-2H-chromene

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

: 3105-95-1
pipecolinic acid

: C28H23Cl2N3O4

Conditions

Conditions	Yield
In ethanol for 2h; Reflux; stereoselective reaction;	89%

...Expand

: 58632-95-4
2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

: 3105-95-1
pipecolinic acid

: 26250-84-0
(S)-(-)-1-(tert-butoxycarbonyl)-2-piperidinecarboxylic acid

Conditions

Conditions	Yield
With triethylamine In water; acetone	88%

: 87-62-7
2,6-dimethylaniline

: 3105-95-1
pipecolinic acid

: 27262-40-4
(S)-2',6'-pipecoloxylidide

Conditions

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 20℃; for 12h;	88%
Stage #1: pipecolinic acid With hydrogenchloride; thionyl chloride In N,N-dimethyl-formamide; toluene at 55℃; for 3h; Stage #2: 2,6-dimethylaniline With hydrogenchloride In N,N-dimethyl-formamide; toluene at 55℃; for 3h;	88%
Stage #1: pipecolinic acid With hydrogenchloride In 1,4-dioxane; toluene for 1h; Stage #2: 2,6-dimethylaniline With trichlorophosphate In 1,4-dioxane; toluene at 20℃; Stage #3: With sodium hydroxide In 1,4-dioxane; water; toluene pH=6 - 11;	60%
Stage #1: 2,6-dimethylaniline; pipecolinic acid With methanesulfonyl chloride In tetrahydrofuran at 50℃; Stage #2: With sodium hydroxide In tetrahydrofuran; water pH=4 - 9;	42%
Stage #1: pipecolinic acid With hydrogenchloride; thionyl chloride In chloroform; water; N,N-dimethyl-formamide; toluene at 40℃; for 3h; pH=2; Sonication; Inert atmosphere; Stage #2: 2,6-dimethylaniline In chloroform; N,N-dimethyl-formamide; toluene at 45℃; for 1.2h; pH-value; Temperature; Wavelength; Sonication;

: 57543-84-7
2-phenyl-3-nitro-2H-chromene

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

: 3105-95-1
pipecolinic acid

: C28H25N3O4

Conditions

Conditions	Yield
In ethanol for 2h; Reflux; stereoselective reaction;	88%

...Expand

: 57543-85-8
6-chloro-3-nitro-2-phenyl-2H-chromene

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

: 3105-95-1
pipecolinic acid

: C28H24ClN3O4

Conditions

Conditions	Yield
In ethanol for 2h; Reflux; stereoselective reaction;	88%

...Expand

: 23901-60-2
4-benzylidene-3-methyl-1-phenylpyrazolone

: 100-52-7
benzaldehyde

: 3105-95-1
pipecolinic acid

: (1S,2R,3R,8aS)-3'-methyl-1',2,3-triphenyl-2,3,6,7,8,8a-hexahydro-5H-spiro[indolizine-1,4'-pyrazol]-5'(1'H)-one

Conditions

Conditions	Yield
In chloroform at 75℃; for 1h; Sealed tube; Inert atmosphere; Molecular sieve;	88%

...Expand

: 1282512-46-2
9-bromo-2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo-[f ]imidazo[1,2-d][1,4]oxazepine

: 3105-95-1
pipecolinic acid

: 1-[2-(2-isopropyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulen-8-yl]-piperidine-2-(S)-carboxylic acid

Conditions

Conditions	Yield
With potassium phosphate; copper(l) iodide; methyl pyridine-2-carboxylate In dimethyl sulfoxide at 80℃; for 24h;	87%

L(-)-Pipecolinic acid Specification

The L-Pipecolinic acid, with the CAS registry number 3105-95-1, is also known as 2-Piperidinecarboxylic acid, (S)-. It belongs to the product categories of Amino Acids and Derivatives; Chiral; Chiral Reagent; Chiral Compound; Chiral Reagents; Heterocycles; Amino Acids & Derivatives; Intermediates. Its EINECS registry number is 221-462-1. This chemical's molecular formula is C₆H₁₁NO₂ and molecular weight is 129.16. What's more, both its IUPAC name and systematic name are the same which is called (2S)-Piperidine-2-carboxylic acid. It should be stored in a cool, dry and well-ventilated place.

Physical properties about L-Pipecolinic acid are: (1)ACD/LogP: 0.243; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2.26; (4)ACD/LogD (pH 7.4): -2.26; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 49.33 Å²; (13)Index of Refraction: 1.479; (14)Molar Refractivity: 32.514 cm³; (15)Molar Volume: 114.736 cm³; (16)Polarizability: 12.89×10^-24cm³; (17)Surface Tension: 40.30 dyne/cm; (18)Density: 1.126 g/cm³; (19)Flash Point: 114.532 °C; (20)Enthalpy of Vaporization: 55.448 kJ/mol; (21)Boiling Point: 265.766 °C at 760 mmHg; (22)Vapour Pressure: 0.0030 mmHg at 25 °C.

When you are dealing with this chemical, you should be very careful. This chemical is inflammation to the skin, eyes and respiratory system or other mucous membranes. Therefore, you should wear suitable protective clothing and avoid contacting with skin and eyes. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(O)[C@H]1NCCCC1
(2) InChI: InChI=1S/C6H11NO2/c8-6(9)5-3-1-2-4-7-5/h5,7H,1-4H2,(H,8,9)/t5-/m0/s1
(3) InChIKey: HXEACLLIILLPRG-YFKPBYRVSA-N

Product Name

L(-)-Pipecolinic acid

Synthetic route

L(-)-Pipecolinic acid Specification

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