benzyl chloroformate

• ChemBase ID: 92311
• Molecular Formular: C8H7ClO2
• Molecular Mass: 170.59298
• Monoisotopic Mass: 170.01345714
• SMILES: O(Cc1ccccc1)C(=O)Cl
• Canonical SMILES: ClC(=O)OCc1ccccc1
• InChI: InChI=1S/C8H7ClO2/c9-8(10)11-6-7-4-2-1-3-5-7/h1-5H,6H2
• InChIKey: HSDAJNMJOMSNEV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl chloroformate
• IUPAC Traditional name: benzyl chloroformate
• Synonyms: benzyl carbonochloridate; Carbobenzoxy chloride; Z-Chloride; Benzyl chloroformate; Benzyl chloroformate solution; Benzyl carbonochloridoate; Benzyl chloroformate 95%; Benzyl chloroformate; Chloroformic acid benzyl ester; 苯甲氧基甲酰氯; 苯甲氧羰酰氯; 氯甲酸苄酯; 氯甲酸苄酯 溶液

Database IDs

• CAS Number: 501-53-1
• EC Number: 207-925-0
• MDL Number: MFCD00000640
• Beilstein Number: 509751
• Merck Index: 141801
• PubChem SID: 162079009; 24847303
• PubChem CID: 10387
• Chemspider ID: 9958
• Wikipedia Title: Benzyl_chloroformate

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.6537483
• LogD (pH = 7.4): 2.6537483
• Log P: 2.6537483
• Molar Refractivity: 42.7384 cm^3
• Polarizability: 16.667994 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 0 °C; -20°C
• Boiling Point: 103 °C (20 Torr); 103 °C/20 mmHg(lit.); 178-180°C; 178-180°C
• Flash Point: 125°C(257°F); 197.6 °F; 20 °C; 68 °F; 80 °C; 92 °C; 92°C
• Density: 1.02 g/mL at 20 °C; 1.195; 1.195 g/cm^3; 1.195 g/mL at 25 °C(lit.); 1.212
• Refractive Index: 1.5190; n20/D 1.519(lit.)
• Vapor Pressure: 1.39 psi ( 20 °C)
• Vapor Density: 1 (vs air)

Safety Information

• Storage Warning: Corrosive/Moisture Sensitive/Store at -20°C; Moisture Sensitive
• European Hazard Symbols: Corrosive (C); Flammable (F); Nature polluting (N); Toxic (T); Harmful (Xn)
• UN Number: 1739; 2924; UN1739
• German water hazard class: 3
• Hazard Class: 3; 8
• Packing Group: 1; 2; I
• Risk Statements: 34-50/53; 45-34-37-50/53; 45-63-11-34-37-48/20-50/53-65-67; R34, R50/53
• Safety Statements: 26-45-60-61; 53-26-36/37/39-45-61; 53-26-36/37/39-45-61-62; S1/2, S26, S45, S60, S61
• TSCA Listed: 是
• EU Index: 607-064-00-4
• GHS Pictograms: GHS02; GHS05; GHS07; GHS08; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H304-H314-H335-H336-H350-H361d-H373-H410; H314-H318-H400-H410; H314-H335-H350-H410
• GHS Precautionary statements: P201-P210-P261-P273-P280-P301 + P310; P201-P261-P273-P280-P305 + P351 + P338-P310; P280-P273-P305+P351+P338-P309-P310-P501A
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1739 8/PG 1; UN 2924 3/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: 95%; 95%, stab. with ca 0.1% sodium carbonate
• Concentration: 50% in toluene
• Grade: technical; technical grade
• Linear Formula: ClCO2CH2C6H5; ClCOOCH2C6H5

DETAILS

Sigma Aldrich - 119938

Application
Cbz-protected anilines were prepared directly from aromatic carboxylic acids, sodium azide and Cbz-Cl.1 Also used in a recently reported 3-step synthesis of 1,2,4-oxadiazoles.2
Protecting reagent in peptide synthesis.
Useful for the introduction of the benzyloxycarbonyl(Cbz,Z) protecting group
Packaging
100 g in Sure/Seal™
2.5 kg in Sure/Seal™
5 g in glass bottle