chloro(1-chloroethoxy)methanone

• ChemBase ID: 77903
• Molecular Formular: C3H4Cl2O2
• Molecular Mass: 142.96866
• Monoisotopic Mass: 141.95883473
• SMILES: O(C(C)Cl)C(=O)Cl
• Canonical SMILES: CC(OC(=O)Cl)Cl
• InChI: InChI=1S/C3H4Cl2O2/c1-2(4)7-3(5)6/h2H,1H3
• InChIKey: QOPVNWQGBQYBBP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: chloro(1-chloroethoxy)methanone; 1-chloroethyl chloroformate
• IUPAC Traditional name: chloro(1-chloroethoxy)methanone; 1-chloroethyl chloroformate
• Synonyms: 1-Chlorocarbonyloxy-1-chloroethane; 1-Chloroethyl Carbonochloridate; 1-Chloroethyl Chloroformate; Chloroformic Acid 1-Chloroethyl Ester; α-Chloroethoxycarbonyl Chloride; α-Chloroethyl Chloroformate; Chloroethyl chloroformate; ACE-Cl; 1-Chloroethyl chloroformate; 1-Chloroethyl carbonochloridoate; 1-Chloroethyl chloroformate; 1-氯乙基氯甲酸酯

Database IDs

• CAS Number: 50893-53-3
• EC Number: 256-834-2
• MDL Number: MFCD00000647
• Beilstein Number: 1747601
• PubChem SID: 162042746; 24858191; 24853857
• PubChem CID: 521305
• Chemspider ID: 454726
• Wikipedia Title: Chloroethyl_chloroformate

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 1.7725649
• LogD (pH = 7.4): 1.7725649
• Log P: 1.7725649
• Molar Refractivity: 27.6075 cm^3
• Polarizability: 11.0032 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Clear Pale Yellow Oil
• Melting Point: -65°C; -65°C
• Boiling Point: 118-119 °C(lit.); 118-121°C; 119-121°C
• Flash Point: 104 °F; 40 °C; 40.5°C; 45°C(113°F)
• Density: 1.312; 1.325; 1.325 g/mL at 25 °C(lit.)
• Refractive Index: 1.422; 1.4230; n20/D 1.422; n20/D 1.422(lit.)
• Vapor Pressure: 3.25 psi ( 20 °C)

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere
• Storage Warning: Moisture Sensitive; Toxic/Flammable/Corrosive/Lachrymatory/Moisture Sensitive/Store under Argon/Keep Cold
• European Hazard Symbols: Toxic (T)
• UN Number: 2742; UN2742
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2; II
• Risk Statements: 10-22-23-34
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 否
• GHS Pictograms: GHS02; GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H226-H302-H314-H331; H330-H302-H314-H318-H226
• GHS Precautionary statements: P210-P303+P361+P353-P304+P340-P305+P351+P338-P320-P330-P405-P501A; P261-P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2742 6.1/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (GC); 98%
• Grade: purum
• Linear Formula: CH3CHClOCOCl

DETAILS

Sigma Aldrich - 301485

Application
Reagent for the selective N-dealkylation of tertiary amines in high yields.
Reagent used to cleave benzhydryl groups from amines.
Packaging
5, 25 g in glass bottle

Sigma Aldrich - 23178

Other Notes
Reagent for the selective N-dealkylation of tertiary amines1; Reagent for the synthesis of alkyl 1-chloroethyl carbonates, useful in the synthesis of drugs2,3,4

REFERENCES

• Reagent, introduced by Olofson, and found to be superior to other chloroformates for dealkylation of tert-amines, e.g. N-alkylpiperidines to piperidines: J. Org. Chem., 49, 2081, 2795, 2081 (1984). For selective debenzylation of tert-amines, see: Synlett, 195 (1993). For reviews, see: Pure Appl. Chem., 60, 1715 (1988); Synthesis, 1 (1989).