(2R)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid

HCID 688022

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Basic information

CAS: 37784-17-1
Standard SMILES: CC(C)(C)OC(=O)N1CCC[C@@H]1C(=O)O
InChIKey: ZQEBQGAAWMOMAI-SSDOTTSWSA-N
Molecular formula: C10H17NO4
Average molar mass: 215.25 g/mol
Monoisotopic mass: 215.11575802

Names & identifiers

Preferred name: (2R)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid
IUPAC: (2R)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
English name: N-Boc-D-proline
Molecular formula: C10H17NO4
Molecular weight: 215.25

Names & synonyms

(2R)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid(2R)-1-((tert-butoxy)carbonyl)pyrrolidine-2-carboxylic acidRefChem:396793805-206-1N-Boc-D-proline37784-17-1Boc-D-Pro-OHBoc-D-proline(R)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acidN-(tert-Butoxycarbonyl)-D-prolineMFCD00063226tert-butoxycarbonyl-D-proline

Show more names

BOC-D-PRON-Boc-D-proLBOC-D-PROLINE-OHBOC-D-PYRD(2)-OHN-T-BOC-D-PROLINEBOC-D-Proline,98%

(TERT-BUTOXYCARBONYL)-D-PROLINEM03316(2R)-1,2-Pyrrolidinedicarboxylic acid 1-(1,1-dimethylethyl) ester;BocDProOH1-(tert-butoxycarbonyl)-D-prolineBoc-DPro-OHN-Boc, D-proline(r)-n-boc-proline

Database identifiers

CAS: 37784-17-1
PubChem CID: 688022
DTXSID: DTXSID901369254
EC Number: 805-206-1
Nikkaji: J1.260.635D

Properties

Computed structural properties

XLogP: 1.5
Topological polar surface area: 66.8 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 4
Rotatable bonds: 3
Heavy atoms: 15
Formal charge: 0
Complexity: 269

Physicochemical properties

Melting point: 134 · 134-137 °C (lit.)
alpha: 60 · 60 º (c=2, acetic acid)
Boiling point: 355.52 °C · 355.52°C (rough estimate)
Density: 1.1835 · 1.1835 (rough estimate)
refractive index: 60 ° · 60 ° (C=2, AcOH)
storage temp.: 2 · 2-8°C
solubility: almost transparency in Acetic acid
form: Crystalline Powder or Crystals
pka: 4.01 · 4.01±0.20(Predicted)
color: White to off-white
optical activity: 22 · [α]22/D +60°, c = 2 in acetic acid
BRN: 479316 · 479316
Major Application: peptide synthesis
InChI: InChI=1S/C10H17NO4/c1-10(2,3)15-9(14)11-6-4-5-7(11)8(12)13/h7H,4-6H2,1-3H3,(H,12,13)/t7-/m1/s1
InChIKey: ZQEBQGAAWMOMAI-SSDOTTSWSA-N
SMILES: N1(C(OC(C)(C)C)=O)CCC[C@@H]1C(O)=O
CAS DataBase Reference: 37784 · 37784-17-1(CAS DataBase Reference)
UNSPSC Code: 12352209 · 12352209
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H335
Precautionary statements: 261 · P261-P280-P301+P312-P302+P352-P305+P351+P338
Safety Statements: 24 · 24/25
WGK Germany: 3 · 3
HS Code: 2933 · 2933 99 80
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 33.3% (1 of 3) of reports.

Warning

H315 (66.7%): Causes skin irritation [Warning Skin corrosion/irritation]

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

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

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (66.7%)

Safety data

wgk: 3
hs_code: 2933 99 80
Signal word: Warning
Symbol(GHS): GHS07
safety_code: 24/25
Storage Class: 11 - Combustible Solids
Hazard statements: H302-H315-H319-H335
Precautionary statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Chemistry & industry

Applications · 1 item

Usestert-Butoxycarbonyl-D-proline is Boc protected 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.