CAS 6404-31-5 1-benzyl hydrogen (R)-pyrrolidine-1,2-dicarboxylate (HCID 111208)

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Basic information

CAS: 6404-31-5
Standard SMILES: O=C(O)[C@H]1CCCN1C(=O)OCc1ccccc1
InChIKey: JXGVXCZADZNAMJ-LLVKDONJSA-N
Molecular formula: C13H15NO4
Average molar mass: 249.26 g/mol
Monoisotopic mass: 249.10010796

Names & identifiers

Preferred name: 1-benzyl hydrogen (R)-pyrrolidine-1,2-dicarboxylate
IUPAC: (2R)-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid
English name: N-Benzyloxycarbonyl-D-proline
Molecular formula: C13H15NO4
Molecular weight: 249.26

Names & synonyms

6404-31-5N-(Benzyloxycarbonyl)-D-proline1-Benzyl hydrogen (R)-pyrrolidine-1,2-dicarboxylateDTXSID60214085EINECS 229-021-5RefChem:429703DTXCID60136576229-021-5Z-D-Pro-OHN-Benzyloxycarbonyl-D-prolineZ-D-PROLINE(R)-N-BENZYLOXYCARBONYLPROLINE

Show more names

(R)-1-(benzyloxycarbonyl)pyrrolidine-2-carboxylic acidD-Z-PROZ-D-ProCbz-D-ProZ-D-Pro-0HPROLINA-Z-DCBZ-D-PRO-OH

N-Carbobenzoxy-D-prolineN-Cbz-D-proline(2R)-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid1-[(benzyloxy)carbonyl]-d-prolineMFCD00063228(2R)-1-[(benzyloxy)carbonyl]pyrrolidine-2-carboxylic acid((Benzyloxy)carbonyl)-D-prolineCBZ-D-PROLINE

Database identifiers

CAS: 6404-31-5
PubChem CID: 111208
DTXSID: DTXSID60214085
ChEMBL: CHEMBL5306625
UNII: HC73QAB2ZF

Properties

Computed structural properties

XLogP: 1.7
Topological polar surface area: 66.8 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 4
Rotatable bonds: 4
Heavy atoms: 18
Formal charge: 0
Complexity: 312

Physicochemical properties

Melting point: 76 · 76-78 °C(lit.)
alpha: 40 · 40 º (c=2, EtOH)
Boiling point: 432.3 · 432.3±45.0 °C(Predicted)
Density: 1.309 · 1.309±0.06 g/cm3(Predicted)
refractive index: 40 ° · 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 · 3.99±0.20(Predicted)
color: White
optical activity: 25 · [α]25/D +40.2°, c = 2 in ethanol
BRN: 485188 · 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

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 12.5% (1 of 8) of reports.

Warning

H302 (12.5%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 8 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory InformationStatus: Active Update: 10-05-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/23421

Hazard Classes and CategoriesAcute Tox. 4 (12.5%)

Safety data

wgk: 3
hs_code: 29339900
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 24/25
Hazard statements: H335-H319-H302-H315-H332
REACH Registrations: Active
Precautionary statements: P264-P280-P305+P351+P338-P337+P313P-P261-P271-P304+P340-P312-P264-P280-P302+P352-P321-P332+P313-P362-P264-P270-P301+P312-P330-P501

Chemistry & industry

Applications · 1 item

UsesN-(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.