(2R)-2-{[(tert-butoxy)carbonyl]amino}-2-phenylacetic acid

HCID 2755953

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Grundinformationen

CAS: 33125-05-2
Standard-SMILES: CC(C)(C)OC(=O)N[C@@H](C(=O)O)c1ccccc1
InChIKey: HOBFSNNENNQQIU-SNVBAGLBSA-N
Summenformel: C13H17NO4
Durchschnittliche Molmasse: 251,28 g/mol
Monoisotopische Masse: 251,11575802

Namen und Bezeichner

Bevorzugter Name: (2R)-2-{[(tert-butoxy)carbonyl]amino}-2-phenylacetic acid
IUPAC: (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylacetic acid
Englischer Name: Boc-D-Phenylglycine
Summenformel: C13H17NO4
Molmasse: 251.28

Namen und Synonyme

(2R)-2-{[(tert-butoxy)carbonyl]amino}-2-phenylacetic acid(2R)-2-(((tert-butoxy)carbonyl)amino)-2-phenylacetic acidRefChem:396925834-862-1Boc-D-Phg-OH33125-05-2Boc-D-PhenylglycineN-Boc-D-PhenylglycineMFCD00062043(R)-2-((tert-Butoxycarbonyl)amino)-2-phenylacetic acidN-(tert-Butoxycarbonyl)-D-2-phenylglycineD-BOC Phenylglycine

Weitere Namen anzeigen

BOC-PHG-OH(R)-N-tert-butoxycarbonyl-2-phenylglycineFS000066BOC-L-PHGST5210539BOC-L-PHG-OHBoc-D-PhenyL

(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylacetic acid4PFG3246TW(alphaR)-alpha-[[(1,1-Dimethylethoxy)carbonyl]amino]benzeneacetic acid(2R)-2-(tert-Butoxycarbonylamino)-2-phenylethanoic acid(R)-2-(Boc-amino)-2-phenylacetic AcidHY-34663tert-Butyloxycarbonyl D-alpha-phenylglycineBoc-D-alpha-phenylglycine

Datenbank-Bezeichner

CAS: 33125-05-2
PubChem CID: 2755953
DTXSID: DTXSID30373158
ChEMBL: CHEMBL5306173
UNII: 4PFG3246TW
EC Number: 834-862-1
Nikkaji: J703.280C

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 2,2
Polarare Oberfläche (TPSA): 75,6 Å²
H-Brücken-Donoren: 2
H-Brücken-Akzeptoren: 4
Frei drehbare Bindungen: 5
Schwere Atome: 18
Formalladung: 0
Komplexität: 303

Physikochemische Eigenschaften

Schmelzpunkt: 88 · 88-91 °C
Siedepunkt: 407.2 · 407.2±38.0 °C(Predicted)
Dichte: 1.182 · 1.182±0.06 g/cm3(Predicted)
Brechungsindex: -140 ° · -140 ° (C=1, EtOH)
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
Löslichkeit: DMSO, Methanol
Aggregatzustand: Crystalline Powder
pka: 3.51 · 3.51±0.10(Predicted)
Farbe: White
Wasserlöslichkeit: Insoluble in water. Slightly soluble in DMSO and methanol.
BRN: 3033982 · 3033982
Major Application: peptide synthesis
InChI: InChI=1S/C13H17NO4/c1-13(2,3)18-12(17)14(9-11(15)16)10-7-5-4-6-8-10/h4-8H,9H2,1-3H3,(H,15,16)
InChIKey: KIAPYAZGXJCKQL-UHFFFAOYSA-N
SMILES: C(O)(=O)CN(C(OC(C)(C)C)=O)C1=CC=CC=C1
CAS Datenbank: 33125 · 33125-05-2(CAS DataBase Reference)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 5 Einträge

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract 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 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Gefahrenhinweise

Hazard Classes and CategoriesSkin Irrit. 2 (100%)；Eye Irrit. 2A (100%)；STOT SE 3 (100%)

Sicherheitsdaten

wgk: 3
hs_code: 29242990
safety_code: 24/25
hazard_class: IRRITANT
Speicherklasse: 13 - Non Combustible Solids

Chemie und Industrie

Anwendungen · 1 Eintrag

VerwendenIt is a reagent of choice for assignment of absolute configuration of chiral primary amines by 1H NMR, giving better results than Mosher's acid ((R)-(+)--Methoxy--(trifluoromethyl)-phenyl-acetic acid. αR)-α-[[(1,1-Dimethylethoxy)carbonyl]amino]-benzeneacetic Acid is D-(+)-2-Phenylglycine with Boc protecting group. (αR)-α-[[(1,1-Dimethylethoxy)carbonyl]amino]-benzeneacetic Acid is used as part of a catalyst combination to catalyze regioselective [4 + 2] cycloadditions of β-substituted cyclic enones and polyconjugated malononitriles. It can also be used to catalyze stereoselective preparation of polyfunctional nitrocyclohexene carboxaldehydes.