tert-butyl N-[(4-isothiocyanatophenyl)methyl]carbamate

• ChemBase ID: 155900
• Molecular Formular: C13H16N2O2S
• Molecular Mass: 264.34334
• Monoisotopic Mass: 264.09324876
• SMILES: CC(C)(C)OC(=O)NCc1ccc(cc1)N=C=S
• Canonical SMILES: S=C=Nc1ccc(cc1)CNC(=O)OC(C)(C)C
• InChI: InChI=1S/C13H16N2O2S/c1-13(2,3)17-12(16)14-8-10-4-6-11(7-5-10)15-9-18/h4-7H,8H2,1-3H3,(H,14,16)
• InChIKey: FZQIQTXXAATZOS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl N-[(4-isothiocyanatophenyl)methyl]carbamate
• IUPAC Traditional name: tert-butyl N-[(4-isothiocyanatophenyl)methyl]carbamate
• Synonyms: 4-(N-tert-Butoxycarbonylaminomethyl)phenyl isothiocyanate; tert-Butyl N-(4-isothiocyanatophenylmethyl)carbamate; BAMPITC; N-Boc-4-isothiocyanatobenzylamine; 4-(Boc-aminomethyl)phenyl isothiocyanate

Database IDs

• CAS Number: 89631-74-3
• MDL Number: MFCD00077918
• Beilstein Number: 9557243
• PubChem SID: 162250038; 24849397
• PubChem CID: 688395

CALCULATED PROPERTIES

• Acid pKa: 14.087988
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.6129353
• LogD (pH = 7.4): 3.6129367
• Log P: 3.612937
• Molar Refractivity: 76.4673 cm^3
• Polarizability: 28.967052 Å^3
• Polar Surface Area: 50.69 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 111-113 °C

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22-36/37/38-42
• Safety Statements: 22-26-36
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H312-H315-H319-H332-H334-H335
• GHS Precautionary statements: P261-P280-P305 + P351 + P338-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Product Information

• Purity: ≥98.0% (HPLC)
• Empirical Formula (Hill Notation): C13H16N2O2S

DETAILS

Sigma Aldrich - 15400

Other Notes
Novel protein micro sequencing reagent with a masked amino group which renders the thiohydantoin upon deblocking susceptible to fluorogenic detection.; A 2.5- to 10-fold increase in sensitivity over the most commonly used detection methods was observed (UV-detection at 254 nm)1,2