benzyl 2,2,2-trichloroethanecarboximidate

• ChemBase ID: 61948
• Molecular Formular: C9H8Cl3NO
• Molecular Mass: 252.52492
• Monoisotopic Mass: 250.96714692
• SMILES: C(=N)(C(Cl)(Cl)Cl)OCc1ccccc1
• Canonical SMILES: N=C(C(Cl)(Cl)Cl)OCc1ccccc1
• InChI: InChI=1S/C9H8Cl3NO/c10-9(11,12)8(13)14-6-7-4-2-1-3-5-7/h1-5,13H,6H2
• InChIKey: HUZCTWYDQIQZPM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl 2,2,2-trichloroethanecarboximidate
• IUPAC Traditional name: benzyl 2,2,2-trichloroethanecarboximidate
• Synonyms: Benzyl 2,2,2-trichloroacetimidate; 2,2,2-Trichloroacetimidic acid benzyl ester; Benzyl 2,2,2-trichloroacetimidate; 2,2,2-三氯乙酰亚胺苄酯; 苄基-2,2,2-三氯乙酰亚氨酸酯; 2,2,2-三氯乙亚氨酸苄酯

Database IDs

• CAS Number: 81927-55-1
• MDL Number: MFCD00000805
• Beilstein Number: 2525375
• PubChem SID: 162027687; 24889440; 24848466
• PubChem CID: 144968

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 3.3738768
• LogD (pH = 7.4): 3.3789399
• Log P: 3.3790047
• Molar Refractivity: 70.2809 cm^3
• Polarizability: 22.883371 Å^3
• Polar Surface Area: 33.08 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 106-114 °C/0.5 mmHg(lit.); 110-114°C/0.5mm; 110-114°C/0.5mm
• Flash Point: >110°C(230°F); 113 °C; 235.4 °F
• Density: 1.356; 1.359 g/mL at 25 °C(lit.)
• Refractive Index: 1.5450; n20/D 1.545; n20/D 1.545(lit.)
• Transition Temperature: solidification point 3-4 °C

Safety Information

• Storage Warning: Moisture Sensitive; MOISTURE SENSITIVE, KEEP COLD
• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38; 36/37/38
• Safety Statements: 26; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335; H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (GC); 97%; 98%; 99%
• Grade: purum
• Impurities: <1% benzyl alcohol
• Linear Formula: CCl3C(=NH)OCH2C6H5

DETAILS

Sigma Aldrich - 140333

Packaging
5, 25 g in glass bottle
Application
Used for the acid-catalyzed benzylation of hydroxy groups.1

Sigma Aldrich - 91075

Other Notes
Reagent used for the benzylation of alcohols under mild, acidic catalysis1,2,3,4,5

REFERENCES

• Mild, selective benzylating agent. Formation of benzyl ethers from alcohols at room temperature is catalyzed by triflic acid; isopropylidene and benzylidene protecting groups are unaffected: J. Chem. Soc., Perkin 1., 2247 (1985). TMS triflate has also been recommended as a catalyst, avoiding racemization of sensitive substrates: Tetrahedron, 43, 1619 (1993). For use in the preparation of benzyl ethers of ?-hydroxy esters, see: Synthesis, 568 (1987).
• The reagent can also be used for mild esterification of carboxylic acids in the presence of a catalytic amount of BF₃ etherate: Synthesis, 168 (1997). For conversion of N-Boc groups to N-Cbz, catalyzed by triflic acid, see: J. Org. Chem., 55, 5170 (1990). See also Appendix 6.