Product Name

  • Name

    D-Pyrrolidine-2-carboxylic acid

  • EINECS 206-452-7
  • CAS No. 344-25-2
  • Article Data44
  • CAS DataBase
  • Density 1.186 g/cm3
  • Solubility Soluble in water
  • Melting Point 223 °C (dec.)(lit.)
  • Formula C5H9NO2
  • Boiling Point 252.2 °C at 760 mmHg
  • Molecular Weight 225.168
  • Flash Point 106.3 °C
  • Transport Information
  • Appearance White to off-white powder
  • Safety 22-24/25-36/37/39-26
  • Risk Codes 22-36/37/38
  • Molecular Structure Molecular Structure of 344-25-2 (D-Pyrrolidine-2-carboxylic acid)
  • Hazard Symbols HarmfulXn, IrritantXi
  • Synonyms D-Prolin;(R)-pyrrolidine-2-carboxylic acid;D-Proline;(2R)-pyrrolidine-2-carboxylic acid;H-D-Pro-OH;D-(+)-Proline; D-Pyrrolidine-2-carboxylic acid;D-(+)-proline;D-Pyrrolidine-2-carboxylic acid;D-Proline (Food Grade);
  • PSA 49.33000
  • LogP 0.15180

Synthetic route

Z-D-proline
6404-31-5

Z-D-proline

D-Prolin
344-25-2

D-Prolin

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol under 760 Torr; for 5h;96%
(S)-1-Pyrrolidin-2-yl-methanol
23356-96-9

(S)-1-Pyrrolidin-2-yl-methanol

D-Prolin
344-25-2

D-Prolin

Conditions
ConditionsYield
With potassium permanganate In water at 15 - 20℃; Concentration;95.65%
(R)-1-(benzyloxycarbonyl)-2,5-dihydro-1H-pyrrole-2-carboxylic acid

(R)-1-(benzyloxycarbonyl)-2,5-dihydro-1H-pyrrole-2-carboxylic acid

D-Prolin
344-25-2

D-Prolin

Conditions
ConditionsYield
With hydrogen; palladium(II) hydroxide In tetrahydrofuran; methanol at 20℃; for 3h;83%
With hydrogen; palladium(II) hydroxide In tetrahydrofuran; methanol at 20℃; for 3h;83%
3,4-dihydro-2H-pyrrole-2-carboxylic acid; hydrochloride

3,4-dihydro-2H-pyrrole-2-carboxylic acid; hydrochloride

D-Prolin
344-25-2

D-Prolin

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol77%
(R)-N-(3,5-dinitrobenzoyl)proline
143492-63-1

(R)-N-(3,5-dinitrobenzoyl)proline

D-Prolin
344-25-2

D-Prolin

Conditions
ConditionsYield
With hydrogenchloride
With hydrogenchloride
(2R,5R)-2-t-butyl-1-t-butyloxycarbonyl-5-(3-chloropropyl)-3-methyl-4-imidazolidinone
119838-25-4

(2R,5R)-2-t-butyl-1-t-butyloxycarbonyl-5-(3-chloropropyl)-3-methyl-4-imidazolidinone

D-Prolin
344-25-2

D-Prolin

Conditions
ConditionsYield
Yield given. Multistep reaction;
(2S,3S)-2,3-Dihydroxy-succinic acid; compound with (R)-pyrrolidine-2-carboxylic acid
126147-98-6

(2S,3S)-2,3-Dihydroxy-succinic acid; compound with (R)-pyrrolidine-2-carboxylic acid

D-Prolin
344-25-2

D-Prolin

Conditions
ConditionsYield
With ammonium hydroxide 1.) methanol, 0.5 h; Yield given. Multistep reaction;
(S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide
96293-17-3, 105024-93-9, 105112-33-2

(S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide

acrolein
107-02-8

acrolein

A

L-proline
147-85-3

L-proline

B

D-Prolin
344-25-2

D-Prolin

Conditions
ConditionsYield
With sodium tetrahydroborate; triethylamine; nickel(II) nitrate Yield given. Multistep reaction. Yields of byproduct given;
L-ornithine-dihydrochloride

L-ornithine-dihydrochloride

D-Prolin
344-25-2

D-Prolin

Conditions
ConditionsYield
With hydrogenchloride; nitrosylchloride Erhitzen des Reaktionsprodukts mit wss. Ba(OH)2;
N-<3-nitro-benzoyl>-dl-proline

N-<3-nitro-benzoyl>-dl-proline

D-Prolin
344-25-2

D-Prolin

Conditions
ConditionsYield
With Cinchonin
acrolein
107-02-8

acrolein

nickel(II) complex of the Schiff's base derived from (S)-o-<(N-benzylprolyl)amino>benzophenone and glycine

nickel(II) complex of the Schiff's base derived from (S)-o-<(N-benzylprolyl)amino>benzophenone and glycine

D-Prolin
344-25-2

D-Prolin

Conditions
ConditionsYield
With hydrogenchloride; sodium cyanoborohydride; triethylamine 1.) MeOH, 60 deg C; 2.) EtOH, 80 deg C; 3.) MeOH, r.t., 24 h; Yield given. Multistep reaction;
acrolein
107-02-8

acrolein

Complex (1)

Complex (1)

A

(S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide
96293-17-3, 105024-93-9, 105112-33-2

(S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide

B

L-proline
147-85-3

L-proline

C

D-Prolin
344-25-2

D-Prolin

Conditions
ConditionsYield
With sodium tetrahydroborate; triethylamine 1.) MeOH, -10 deg C, 2.) water, 25 deg C; Yield given. Multistep reaction. Yields of byproduct given;
N-benzyloxycarbonyl-L-phenylalanyl-D-proline
746639-86-1

N-benzyloxycarbonyl-L-phenylalanyl-D-proline

A

N-Cbz-L-Phe
1161-13-3

N-Cbz-L-Phe

B

D-Prolin
344-25-2

D-Prolin

Conditions
ConditionsYield
With hydrogenchloride; carboxypeptisae-A In water at 37℃; pH=6.5; Enzyme kinetics; Kinetics; Further Variations:; Reagents;
(R)-2-Amino-5-oxo-pentanoic acid

(R)-2-Amino-5-oxo-pentanoic acid

D-Prolin
344-25-2

D-Prolin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq. HCl / Heating
2: 77 percent / H2 / Pd/C / methanol
View Scheme
(RS,R)-(-)-(N-p-toluenesulfinyl)-2-amino-5,5-dimethoxypentanonitrile

(RS,R)-(-)-(N-p-toluenesulfinyl)-2-amino-5,5-dimethoxypentanonitrile

D-Prolin
344-25-2

D-Prolin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aq. HCl / Heating
2: aq. HCl / Heating
3: 77 percent / H2 / Pd/C / methanol
View Scheme
methyl 2,3-dideoxy-5,6-O-isopropylidene-4-O-p-tolylsulfonyl-D-erythro-hexonate
136963-32-1

methyl 2,3-dideoxy-5,6-O-isopropylidene-4-O-p-tolylsulfonyl-D-erythro-hexonate

D-Prolin
344-25-2

D-Prolin

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 91 percent / NaN3 / dimethylformamide / 12 h / 100 °C
2: 82 percent / DIBAL / light petroleum; toluene; hexane / 1 h / -78 °C
3: 76 percent / H2 / 10percent Pd/C / methanol / 7 h / 760 Torr / Ambient temperature
4: 82 percent / NaHCO3 / aq. ethanol
5: 95 percent / 80percent aq. AcOH / 120 h / Ambient temperature
6: 79 percent / aq. NaIO4 / methanol / 2 h
7: 88 percent / aq. NaClO2, Na2HPO4 / various solvent(s) / 1 h
8: 96 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr
View Scheme
(2R)-(+)-phenylmethyl 2-formylpyrrolidine-1-carboxylate
50463-82-6, 71461-30-8, 105706-84-1, 143393-11-7

(2R)-(+)-phenylmethyl 2-formylpyrrolidine-1-carboxylate

D-Prolin
344-25-2

D-Prolin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 88 percent / aq. NaClO2, Na2HPO4 / various solvent(s) / 1 h
2: 96 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr
View Scheme
(R)-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]pyrrolidine
200499-55-4

(R)-2-[(S)-2,2-dimethyl-1,3-dioxolan-4-yl]pyrrolidine

D-Prolin
344-25-2

D-Prolin

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 82 percent / NaHCO3 / aq. ethanol
2: 95 percent / 80percent aq. AcOH / 120 h / Ambient temperature
3: 79 percent / aq. NaIO4 / methanol / 2 h
4: 88 percent / aq. NaClO2, Na2HPO4 / various solvent(s) / 1 h
5: 96 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr
View Scheme
(R)-4-Azido-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butyraldehyde
200499-54-3

(R)-4-Azido-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butyraldehyde

D-Prolin
344-25-2

D-Prolin

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 76 percent / H2 / 10percent Pd/C / methanol / 7 h / 760 Torr / Ambient temperature
2: 82 percent / NaHCO3 / aq. ethanol
3: 95 percent / 80percent aq. AcOH / 120 h / Ambient temperature
4: 79 percent / aq. NaIO4 / methanol / 2 h
5: 88 percent / aq. NaClO2, Na2HPO4 / various solvent(s) / 1 h
6: 96 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr
View Scheme
(R)-1-benzyloxycarbonyl-2-[(S)-1,2-dihydroxyethyl]pyrrolidine
200499-58-7

(R)-1-benzyloxycarbonyl-2-[(S)-1,2-dihydroxyethyl]pyrrolidine

D-Prolin
344-25-2

D-Prolin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 79 percent / aq. NaIO4 / methanol / 2 h
2: 88 percent / aq. NaClO2, Na2HPO4 / various solvent(s) / 1 h
3: 96 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr
View Scheme
(R)-4-Azido-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butyric acid methyl ester
200499-52-1

(R)-4-Azido-4-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butyric acid methyl ester

D-Prolin
344-25-2

D-Prolin

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 82 percent / DIBAL / light petroleum; toluene; hexane / 1 h / -78 °C
2: 76 percent / H2 / 10percent Pd/C / methanol / 7 h / 760 Torr / Ambient temperature
3: 82 percent / NaHCO3 / aq. ethanol
4: 95 percent / 80percent aq. AcOH / 120 h / Ambient temperature
5: 79 percent / aq. NaIO4 / methanol / 2 h
6: 88 percent / aq. NaClO2, Na2HPO4 / various solvent(s) / 1 h
7: 96 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr
View Scheme
(2R,4'S)-N-Benzyloxycarbonyl-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)pyrrolidine
200499-57-6

(2R,4'S)-N-Benzyloxycarbonyl-2-(2',2'-dimethyl-1',3'-dioxolan-4'-yl)pyrrolidine

D-Prolin
344-25-2

D-Prolin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 95 percent / 80percent aq. AcOH / 120 h / Ambient temperature
2: 79 percent / aq. NaIO4 / methanol / 2 h
3: 88 percent / aq. NaClO2, Na2HPO4 / various solvent(s) / 1 h
4: 96 percent / H2 / 10percent Pd/C / methanol / 5 h / 760 Torr
View Scheme
1-(3,5-dinitro-benzoyl)-DL-proline
99989-76-1, 143492-62-0

1-(3,5-dinitro-benzoyl)-DL-proline

D-Prolin
344-25-2

D-Prolin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: brucine; acetone
2: aqueous HCl
View Scheme
Co2 (CO)8

Co2 (CO)8

N-[(methyl)carbonyl]-2-pyrroline
23105-58-0

N-[(methyl)carbonyl]-2-pyrroline

rac-octan-2-ol
4128-31-8

rac-octan-2-ol

D-Prolin
344-25-2

D-Prolin

Conditions
ConditionsYield
With pyridine; H2; CO In tetrahydrofuran; hydrogenchloride
N-[(methyl)carbonyl]-2-pyrroline
23105-58-0

N-[(methyl)carbonyl]-2-pyrroline

rac-octan-2-ol
4128-31-8

rac-octan-2-ol

D-Prolin
344-25-2

D-Prolin

Conditions
ConditionsYield
With pyridine; H2; CO; Co2(CO)8 In tetrahydrofuran; hydrogenchloride
rac-Pro-OH
609-36-9

rac-Pro-OH

A

L-proline
147-85-3

L-proline

B

D-Prolin
344-25-2

D-Prolin

Conditions
ConditionsYield
With C24H29CoN2O4 In dichloromethane; water at 10℃; for 24h; Resolution of racemate; optical yield given as %ee;
Stage #1: rac-Pro-OH With C24H29CoN2O4 In dichloromethane; water at 10℃; for 24h; Resolution of racemate;
Stage #2: With sodium dithionite In dichloromethane; water for 5h; Resolution of racemate; optical yield given as %ee;
With shaking calcined L-Pro chiral ordered mesoporous silica Resolution of racemate;
2-hydroxymethylpyrrolidinium trifluoroacetate

2-hydroxymethylpyrrolidinium trifluoroacetate

A

L-proline
147-85-3

L-proline

B

D-Prolin
344-25-2

D-Prolin

Conditions
ConditionsYield
With potassium permanganate; sulfuric acid In water at 0 - 20℃; optical yield given as %ee;
Glu-Gln-Arg-Pro-Arg
1281970-89-5

Glu-Gln-Arg-Pro-Arg

A

L-glutamic acid
56-86-0

L-glutamic acid

B

L-arginine
74-79-3

L-arginine

C

D-Prolin
344-25-2

D-Prolin

Conditions
ConditionsYield
With hydrogenchloride; water at 150℃; for 12h;
apratoxin S5
1334149-95-9

apratoxin S5

A

N-methylalanine
3913-67-5

N-methylalanine

B

N-methyl-L-isoleucine
4125-98-8

N-methyl-L-isoleucine

C

O-Methyltyrosine
6230-11-1

O-Methyltyrosine

D

D-Prolin
344-25-2

D-Prolin

Conditions
ConditionsYield
With hydrogenchloride; water at 110℃; for 24h;
methanol
67-56-1

methanol

D-Prolin
344-25-2

D-Prolin

D-proline methyl ester hydrochloride
2133-40-6

D-proline methyl ester hydrochloride

Conditions
ConditionsYield
With thionyl chloride at 0℃; for 2h;100%
With thionyl chloride Reflux;97%
In dimethyl sulfoxide at 10 - 80℃; for 2h;88%
pivaloyl chloride
3282-30-2

pivaloyl chloride

D-Prolin
344-25-2

D-Prolin

ButCO-D-Pro-OH
145612-92-6

ButCO-D-Pro-OH

Conditions
ConditionsYield
With sodium hydroxide100%
benzyl chloroformate
501-53-1

benzyl chloroformate

D-Prolin
344-25-2

D-Prolin

Z-D-proline
6404-31-5

Z-D-proline

Conditions
ConditionsYield
With sodium hydroxide In water; toluene at 20℃; for 1h; Inert atmosphere;100%
With sodium hydroxide In water at 0 - 20℃;93%
With sodium hydroxide In water Ambient temperature;
methanol
67-56-1

methanol

D-Prolin
344-25-2

D-Prolin

methyl (3R)-pyrrolidine-3-carboxylate hydrochloride
874964-22-4

methyl (3R)-pyrrolidine-3-carboxylate hydrochloride

Conditions
ConditionsYield
With thionyl chloride at 20℃; for 16.5h;100%
D-Prolin
344-25-2

D-Prolin

D-proline methyl ester hydrochloride
2133-40-6

D-proline methyl ester hydrochloride

Conditions
ConditionsYield
With thionyl chloride In methanol Reflux;100%
cadmium(II) nitrate tetrhydrate

cadmium(II) nitrate tetrhydrate

D-Prolin
344-25-2

D-Prolin

Cd[D-proline]2

Cd[D-proline]2

Conditions
ConditionsYield
With triethylamine In methanol at 20℃; for 1h;100%
D-Prolin
344-25-2

D-Prolin

Methacryloyl chloride
920-46-7

Methacryloyl chloride

(2R)-1-methacryloylpyrrolidin-2-carboxylic acid
106089-24-1

(2R)-1-methacryloylpyrrolidin-2-carboxylic acid

Conditions
ConditionsYield
With sodium hydroxide In acetone at 0℃; for 0.5h;99%
With sodium hydroxide In tetrahydrofuran; acetone at 5 - 20℃; for 3h; pH=11 - 12; Cooling with ice;83.8%
With sodium hydroxide In acetone at 20℃; for 4h; pH=10.3;81%
D-Prolin
344-25-2

D-Prolin

L-proline
147-85-3

L-proline

Conditions
ConditionsYield
With porcine kidney D-amino acid oxidase (EC 1.4.3.3.); sodium cyanoborohydride; flavin adenine dinucleotide In phosphate buffer at 37℃;99%
4-Fluoro-2-hydroxyacetophenone
1481-27-2

4-Fluoro-2-hydroxyacetophenone

D-Prolin
344-25-2

D-Prolin

(R)-1-(4-acetyl-3-hydroxyphenyl)pyrrolidine-2-carboxylic acid
1305325-82-9

(R)-1-(4-acetyl-3-hydroxyphenyl)pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With potassium carbonate In dimethyl sulfoxide at 95℃; for 2.5h;99%
n-dodecanoyl chloride
112-16-3

n-dodecanoyl chloride

D-Prolin
344-25-2

D-Prolin

N-lauroyl-D-proline
1248347-91-2

N-lauroyl-D-proline

Conditions
ConditionsYield
Stage #1: D-Prolin With pyridine; chloro-trimethyl-silane In dichloromethane for 1.16667h;
Stage #2: n-dodecanoyl chloride In dichloromethane at 0 - 20℃; for 1.83333h;
99%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

D-Prolin
344-25-2

D-Prolin

N-(tert-butoxycarbonyl)-D-proline
37784-17-1

N-(tert-butoxycarbonyl)-D-proline

Conditions
ConditionsYield
With triethylamine98%
With triethylamine In dichloromethane at 25 - 30℃;97%
Stage #1: D-Prolin With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃; for 0.5h;
Stage #2: di-tert-butyl dicarbonate In 1,4-dioxane; water at 0 - 20℃;
95%
butyraldehyde
123-72-8

butyraldehyde

D-Prolin
344-25-2

D-Prolin

(R)-1-butylpyrrolidine-2-carboxylic acid

(R)-1-butylpyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; under 3750.38 Torr; for 5h; Inert atmosphere;98%
D-Prolin
344-25-2

D-Prolin

N-nitroso-D-proline
42022-03-7

N-nitroso-D-proline

Conditions
ConditionsYield
With 3,3-dimethyl-2-nitroso-2,3-dihydrobenzo[d]isothiazole 1,1-dioxide In dichloromethane at 20℃; Sealed tube;98%
tetra-n-butylphosphonium hydroxide
14518-69-5

tetra-n-butylphosphonium hydroxide

D-Prolin
344-25-2

D-Prolin

tetrabutylphosphonium (S)-(+)-prolinate

tetrabutylphosphonium (S)-(+)-prolinate

Conditions
ConditionsYield
In water at 20℃; for 2h;97%
Λ-[Ir(2-phenylquinoline)2(MeCN)2](PF6)

Λ-[Ir(2-phenylquinoline)2(MeCN)2](PF6)

D-Prolin
344-25-2

D-Prolin

Λ-[Ir(2-phenylquinoline)2(D-proline)]

Λ-[Ir(2-phenylquinoline)2(D-proline)]

Conditions
ConditionsYield
With sodium methylate In methanol at 20℃; for 12h; Darkness;97%
With sodium methylate In methanol at 50℃; for 24h; Inert atmosphere; diastereoselective reaction;
1-Naphthalenesulfonyl chloride
85-46-1

1-Naphthalenesulfonyl chloride

D-Prolin
344-25-2

D-Prolin

(R)-1-(naphthalen-1-ylsulfonyl)pyrrolidine-2-carboxylic acid
126522-72-3

(R)-1-(naphthalen-1-ylsulfonyl)pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran at 50℃; for 5h;96.2%
chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

D-Prolin
344-25-2

D-Prolin

(R)-1-ethoxycarbonylprolin
175725-27-6

(R)-1-ethoxycarbonylprolin

Conditions
ConditionsYield
With sodium carbonate In tetrahydrofuran; water at 0 - 20℃; for 3.75h;96%
With potassium carbonate In water 1) 0 deg C, 1 h, 2) r.t., 2 h; Yield given;
Stage #1: chloroformic acid ethyl ester; D-Prolin With sodium hydroxide; water at 0 - 20℃; pH=9 - 10;
Stage #2: With hydrogenchloride; water at 0℃; pH=1;
isatoic anhydride
118-48-9

isatoic anhydride

D-Prolin
344-25-2

D-Prolin

(11aS)-2,3,5,10,11,11a-hexahydro-1H-pyrrolo<2,1-c><1,4>benzodiazepin-5,11-dione
154802-75-2

(11aS)-2,3,5,10,11,11a-hexahydro-1H-pyrrolo<2,1-c><1,4>benzodiazepin-5,11-dione

Conditions
ConditionsYield
In dimethyl sulfoxide at 180℃; Condensation;96%
In dimethyl sulfoxide at 150℃; for 2h; Inert atmosphere;82%
In dimethyl sulfoxide at 100℃; for 5h;81%
formaldehyd
50-00-0

formaldehyd

D-Prolin
344-25-2

D-Prolin

Conditions
ConditionsYield
Stage #1: formaldehyd; D-Prolin
Stage #2: With hydrogen
96%
With hydrogen; palladium 10% on activated carbon In methanol under 775.743 Torr; for 18h;96%
With hydrogen; palladium 10% on activated carbon In methanol under 775.743 Torr; for 18h;96%
dronabinol
1972-08-3

dronabinol

D-Prolin
344-25-2

D-Prolin

C21H30O2*C5H9NO2

C21H30O2*C5H9NO2

Conditions
ConditionsYield
In n-heptane at 20℃; for 48h; Inert atmosphere;96%
dimethylsulfite
616-42-2

dimethylsulfite

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

D-Prolin
344-25-2

D-Prolin

(D)-proline, methyl ester, tosylate salt
104848-85-3

(D)-proline, methyl ester, tosylate salt

Conditions
ConditionsYield
In diethyl ether at 90℃; for 7h;95%
2-(2-bromobenzyloxy)aniline
3434-04-6

2-(2-bromobenzyloxy)aniline

D-Prolin
344-25-2

D-Prolin

4-methoxyphenyl-acetic chloride
4693-91-8

4-methoxyphenyl-acetic chloride

(R)-1-[(4-methoxyphenyl)acetyl]pyrrolidine-2-carboxylic acid

(R)-1-[(4-methoxyphenyl)acetyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide In water; acetone95%
2-(3-fluoro-6-nitrophenyl)benzothiazole
1085704-41-1

2-(3-fluoro-6-nitrophenyl)benzothiazole

D-Prolin
344-25-2

D-Prolin

(2R)-1-[3-(1,3-benzothiazol-2-yl)-4-nitrophenyl]pyrrolidine-2-carboxylic acid

(2R)-1-[3-(1,3-benzothiazol-2-yl)-4-nitrophenyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate In tetrahydrofuran; water for 16h; Reflux;95%
chloroacetyl chloride
79-04-9

chloroacetyl chloride

D-Prolin
344-25-2

D-Prolin

1-(2-chloroacetyl)proline
23500-11-0

1-(2-chloroacetyl)proline

Conditions
ConditionsYield
With dmap at 20℃; for 5.16667h; Reagent/catalyst;94.8%
tetrabutylammonium hydroxide triacontahydrate

tetrabutylammonium hydroxide triacontahydrate

D-Prolin
344-25-2

D-Prolin

tetrabutylammonium (R)-prolinate
1198400-65-5

tetrabutylammonium (R)-prolinate

Conditions
ConditionsYield
In water at 100℃; for 65h;94%
tetra-n-butylphosphonium hydroxide
14518-69-5

tetra-n-butylphosphonium hydroxide

D-Prolin
344-25-2

D-Prolin

tetrabutylphosphonium (R)-(-)-prolinate

tetrabutylphosphonium (R)-(-)-prolinate

Conditions
ConditionsYield
In water at 100℃; for 24h;94%
Cbz-Gly-ONSuc
2899-60-7

Cbz-Gly-ONSuc

L-glutamic dimethyl ester hydrochloride
23150-65-4

L-glutamic dimethyl ester hydrochloride

D-Prolin
344-25-2

D-Prolin

dimethyl N-(benzyloxycarbonyl)glycyl-D-prolyl-L-glutamate

dimethyl N-(benzyloxycarbonyl)glycyl-D-prolyl-L-glutamate

Conditions
ConditionsYield
Stage #1: Cbz-Gly-ONSuc; D-Prolin With N-ethyl-N,N-diisopropylamine In ethyl acetate for 12h; Inert atmosphere; Green chemistry;
Stage #2: With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate In ethyl acetate for 0.5h; Inert atmosphere; Green chemistry;
Stage #3: L-glutamic dimethyl ester hydrochloride In ethyl acetate for 1h; Inert atmosphere; Green chemistry; chemoselective reaction;
94%
perfluoro-1-butanesulfonyl fluoride
2386-60-9

perfluoro-1-butanesulfonyl fluoride

D-Prolin
344-25-2

D-Prolin

(R)-1-(butylsulfonyl)pyrrolidine-2-carboxylic acid
910481-82-2

(R)-1-(butylsulfonyl)pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With potassium carbonate In tetrahydrofuran at 50℃; for 5h;93.1%

Proline Chemical Properties

Molecular Structure of D-Proline (CAS NO.344-25-2):

IUPAC Name: (2R)-pyrrolidin-1-ium-2-carboxylate 
Empirical Formula: C5H9NO2
Molecular Weight: 115.1305
H bond acceptors: 3
H bond donors: 2
Freely Rotating Bonds: 1
Polar Surface Area: 29.54 Å2
Index of Refraction: 1.487
Molar Refractivity: 27.9 cm3
Molar Volume: 96.9 cm3
Surface Tension: 43.4 dyne/cm
Density: 1.186 g/cm3
Flash Point: 106.3 °C
Enthalpy of Vaporization: 53.9 kJ/mol
Boiling Point: 252.2 °C at 760 mmHg
Vapour Pressure: 0.00615 mmHg at 25°C
EINECS: 206-452-7
Melting point:223 °C (dec.)(lit.)
Alpha: 84.75 o (C=4, H2O)
Refractive index: 85 ° (C=4, H2O)
Storage temp: Store at RT
Water Solubility: soluble >1000 g/L (20 oC)
Melting point: 223 °C (dec.)(lit.)
Product Categories: Amino Acids series; Miscellaneous Biochemicals; Proline [Pro, P]; Amino Acids and Derivatives; alpha-Amino Acids; Amino Acids;Biochemistry; Amino Acids and Derivatives

Proline Uses

 D-Proline (CAS NO.344-25-2) is used as synthesizing the drugs.

Proline Safety Profile

Hazard Codes of D-Proline (CAS NO.344-25-2): IrritantXi,HarmfulXn
Risk Statements: 22-36/37/38 
R22: Harmful if swallowed. 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 22-24/25-36/37/39-26 
S22: Do not breathe dust. 
S24/25: Avoid contact with skin and eyes. 
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 3
F: 3-10
Hazard Note: Irritant

Proline Specification

 D-Proline , with CAS number of 344-25-2, can be called (2R)-2-Pyrrolidinecarboxylic acid ; (R)-(+)-Proline ; (+)-(R)-Proline ; (R)-Proline ; (R)-Pyrrolidine-2-carboxylic acid ; D-(+)-Proline; D-Pyrrolidine-2-carboxylic acid ; (R)-pyrrolidine-2-carboxylic acid . It is a white to off-white powder.

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