N-Benzyloxycarbonyl-D-proline

Product Name: N-Benzyloxycarbonyl-D-proline
CAS No.: 6404-31-5
Chemical Name: N-Benzyloxycarbonyl-D-proline
Synonyms: D-Z-PRO;Z-D-Pro;Cbz-D-Pro;Z-D-PRO-OH;Z-D-Pro-0H;PROLINA-Z-D;Z-D-PROLINE;CBZ-D-PRO-OH;N-Cbz-D-ProL;CBZ-D-PROLINE
CBNumber: CB6295385
Molecular Formula: C13H15NO4
Formula Weight: 249.26
MOL File: 6404-31-5.mol

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N-Benzyloxycarbonyl-D-proline Property

Melting point:: 76-78 °C(lit.)
alpha: 40 º (c=2, EtOH)
Boiling point:: 432.3±45.0 °C(Predicted)
Density: 1.309±0.06 g/cm3(Predicted)
refractive index: 40 ° (C=2, EtOH)
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
solubility: Chloroform (Slightly), DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
form: Crystalline Powder or Powder
pka: 3.99±0.20(Predicted)
color: White
optical activity: [α]25/D +40.2°, c = 2 in ethanol
BRN: 485188
InChI: InChI=1S/C13H15NO4/c15-12(16)11-7-4-8-14(11)13(17)18-9-10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9H2,(H,15,16)/t11-/m1/s1
InChIKey: JXGVXCZADZNAMJ-LLVKDONJSA-N
SMILES: N1(C(OCC2=CC=CC=C2)=O)CCC[C@@H]1C(O)=O
CAS DataBase Reference: 6404-31-5(CAS DataBase Reference)

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Safety

Hazard Codes: Xi
Safety Statements: 24/25
WGK Germany: 3
HS Code: 29339900

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P321Specific treatment (see … on this label).

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 860735
Product name: (+)-Z-D-proline
Purity: 98%
Packaging: 500MG
Price: $63.9
Updated: 2023/01/07

TCI Chemical

Product number: C1730
Product name: N-Carbobenzoxy-D-proline
Purity: >98.0%(HPLC)(T)
Packaging: 5g
Price: $42
Updated: 2025/07/31

TCI Chemical

Product number: C1730
Product name: N-Carbobenzoxy-D-proline
Purity: >98.0%(HPLC)(T)
Packaging: 25g
Price: $121
Updated: 2025/07/31

Usbiological

Product number: 264206
Product name: N-Benzyloxycarbonyl-D-proline
Packaging: 25g
Price: $388
Updated: 2021/12/16

TRC

Product number: B287815
Product name: N-(Benzyloxycarbonyl)-D-proline
Packaging: 10g
Price: $165
Updated: 2021/12/16

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N-Benzyloxycarbonyl-D-proline Chemical Properties,Usage,Production

Chemical Properties

White crystalline powder or powder

Uses

N-(Benzyloxycarbonyl)-D-proline is an an N-Cbz-protected form of D-proline (P755990). It is used to prepare trichostatin A and trapoxin B analogs as histone deacetylase inhibitors. It is also used to prepare potent and selective nonpeptide inhibitors of caspases 3 and 7.

Synthesis

501-53-1

344-25-2

6404-31-5

Step-1: Preparation of (R)-1-(benzyloxycarbonyl)pyrrolidine-2-carboxylic acid (12a). To a stirred solution of D-proline (1.2 g, 10.42 mmol) in 2 N NaOH aqueous solution (20.85 mL, 41.7 mmol), benzyl chloroformate (1.488 mL, 10.42 mmol) was slowly added dropwise at 0°C. The reaction mixture was gradually warmed to room temperature and stirred overnight. Upon completion of the reaction, the reaction mixture was washed with methyl tert-butyl ether (MTBE, 2 × 25 mL) and then acidified with concentrated hydrochloric acid to pH ≈ 2. The aqueous phase was extracted with ethyl acetate (2 × 200 mL), and the organic phases were combined and washed sequentially with water (50 mL) and saturated saline (25 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford (R)-1-(benzyloxycarbonyl)pyrrolidine-2-carboxylic acid (12a) (2.41 g, 9.67 mmol) as a white solid in 93% yield. The product was characterized by 1H NMR (300 MHz, DMSO-d6) and mass spectrometry (MS): 1H NMR δ 12.66 (s, 1H), 7.42-7.25 (m, 5H), 5.14-4.97 (m, 2H), 4.20 (ddd, J = 22.7, 8.8, 3.5 Hz, 1H), 3.50-3.25 (m, 2H), 2.32-2.08 (m, 1H), 1.97-1.75 (m, 3H); MS (ES+) m/z 250.2 ([M+H]+), 272.2 ([M+Na]+), (ES-) m/z 248.2 ([M-H]-), 284.2 ([M+Cl]-), 497.4 ([2M-H]-).

References

[1] Patent: WO2015/62486, 2015, A1. Location in patent: Paragraph 00191
[2] Patent: WO2017/59178, 2017, A1. Location in patent: Page/Page column 73
[3] Journal of Pharmaceutical Sciences, 1991, vol. 80, # 9, p. 837 - 842
[4] Angewandte Chemie - International Edition, 2006, vol. 45, # 28, p. 4593 - 4597
[5] European Journal of Medicinal Chemistry, 2009, vol. 44, # 7, p. 2807 - 2814

N-Benzyloxycarbonyl-D-proline Preparation Products And Raw materials

Raw materials

Preparation Products

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N-Benzyloxycarbonyl-D-proline Suppliers

Americas 1 Belgium 1 China 300 Europe 3 France 1 Germany 8 India 28 Japan 7 Slovakia 1 Switzerland 7 The Netherlands 1 Ukraine 1 United Kingdom 12 United States 55 Global 426

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View Lastest Price from N-Benzyloxycarbonyl-D-proline manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD

Product: N-Benzyloxycarbonyl-D-proline 6404-31-5
Price: US $0.00/Kg/Drum
Min. Order: 1KG
Purity: 98%min
Supply Ability: 500kgs
Release date: 2021-08-27

Zhuozhou Wenxi import and Export Co., Ltd

Product: Z-D-Proline 6404-31-5
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-07-10

Zhuozhou Wenxi import and Export Co., Ltd

Product: Z-D-Proline 6404-31-5
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-07-08

6404-31-5, N-Benzyloxycarbonyl-D-prolineRelated Search:

Z-D-PYR-OH Ethyl 2-(Chlorosulfonyl)acetate L-PROLINE-(4-3H(N)) PYRAZOPHOS Hyaluronic acid Trimethoprim L-Proline Folic acid N-Carbobenzyloxyglycine Pyrrolidine D-Proline cis-4-Hydroxy-L-proline Z-GAMMA-ABU-OH Z-D-Pro-ONp Z-D-Pyr-Osu Z-D-PRO-NH2 Z-D-PHE-ONP Z-D-PRO-OTBU

Cbz-D-Pro

PROLINA-Z-D

1,2-PYRROLIDINEDICARBOXYLIC ACID, 1-(PHENYLMETHYL)ESTER, (2R)-

1,2-PYRROLIDINEDICARBOXYLIC ACID, 1-(PHENYLMETHYL) ESTER, (R)-

1-[(BENZYLOXY)CARBONYL]PYRROLIDINE-2-CARBOXYLIC ACID

(R)-Z-pyrrolidine-2-carboxylic acid

Z-D-proline≥ 98% (HPLC)

BENZYLOXYCARBONYL-D-PROLINE

D-Z-PRO

(+)-CARBOBENZYLOXY-D-PROLINE

(+)-Carbobenzyloxy-P-proline

N-Benzyloxycarbonyl-D-proline ,99%

Benzyloxycarbonyl-D-proline (Z-D-pro-OH)

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

N-Cbz-D-proline Z-D-Pro-OH

Z-D-Pro

N-benzyloxycarbonyl-D-proline (KSM-I)

CBZ-D-PROLINE

CBZ-D-PRO-OH

(R)-N-BENZYLOXYCARBONYLPROLINE

N-ALPHA-CBZ-D-PROLINE

N-ALPHA-BENZYLOXYCARBONYL-D-PROLINE

N-ALPHA-CARBOBENZOXY-D-PYRROLIDINE-2-CARBOXYLIC ACID

N-ALPHA-CARBOBENZOXY-D-PROLINE

N-CARBOBENZOXY-D-PROLINE

N-CBZ-D-PROLINE

N-BENZYLOXYCARBONYLAMINO-D-PROLINE

N-BENZYLOXYCARBONYL-D-PROLINE

N-Z-D-PROLINE

Z-D-PROLINE

Z-D-PRO-OH

Z-D-PYRD(2)-OH

1-benzyl hydrogen (R)-pyrrolidine-1,2-dicarboxylate

N-CBZ-D-PROLINE CRYSTALLINE

N-Cbz-D-proline,98+%

N-CBZ-D-PRO-OH

N-CARBOBENZYLOXY-D-PROLINE

N-Benzyloxycarbonyl-D-proline, 98+%

Z-D-PROLINE extrapure

(+)-Z-D-proline

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

(2R)-1,2-Pyrrolidinedicarboxylic acid 1-benzyl ester

1-(Benzyloxycarbonyl)-D-proline

N-Carbobenzoxy-D-proline &gt

N-Cbz-D-ProL

N-Benzyloxycarbonyl-D-proline [CBZ-D-Proline]

N-Benzyloxycarbonyl-D-proline USP/EP/BP

N-Cbz-D-proline, 98% [Z-D-Pro-OH]

D-Cbz-Proline

N-Benzyloxycarbonyl-D-proline, 95%

Z-D-Pro-0H

6404-31-5

6404-31-

1144-21-2

Peptide Synthesis

Specialty Synthesis

Protected & Labeled Amino Acids

Cbz-Amino Acids