chloro(2,2,2-trichloroethoxy)methanone

• ChemBase ID: 77889
• Molecular Formular: C3H2Cl4O2
• Molecular Mass: 211.85878
• Monoisotopic Mass: 209.88089002
• SMILES: O(CC(Cl)(Cl)Cl)C(=O)Cl
• Canonical SMILES: ClC(=O)OCC(Cl)(Cl)Cl
• InChI: InChI=1S/C3H2Cl4O2/c4-2(8)9-1-3(5,6)7/h1H2
• InChIKey: LJCZNYWLQZZIOS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: chloro(2,2,2-trichloroethoxy)methanone; 2,2,2-trichloroethyl chloroformate
• IUPAC Traditional name: chloro(2,2,2-trichloroethoxy)methanone; 2,2,2-trichloroethyl chloroformate
• Synonyms: Trichloroethyl chloroformate; 2,2,2-Trichlorethoxycarbonyl chloride; 2,2,2-Trichloroethoxycarbonyl chloride; 2,2,2-Trichloroethyl chloroformate; Chloroformic acid 2,2,2-trichloroethyl ester; β, β, β-Trichloroethoxycarbonyl chloride; 2,2,2-Trichloroethyl carbonochloridoate; 2,2,2-Trichloroethyl chloroformate; 三氯乙氧基甲酰氯; 氯甲酸-2,2,2-三氯乙酯; 2,2,2-三氯乙基氯甲酯

Database IDs

• CAS Number: 17341-93-4
• EC Number: 241-363-7
• MDL Number: MFCD00000810
• Beilstein Number: 970619
• PubChem SID: 24853913; 24848380; 162042732
• PubChem CID: 10387; 87063
• Chemspider ID: 78534
• Wikipedia Title: 2,2,2-Trichlorethoxycarbonyl_chloride

CALCULATED PROPERTIES

• Molar Refractivity: 38.0803 cm^3
• Polarizability: 14.960162 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.504431
• LogD (pH = 7.4): 2.504431
• Log P: 2.504431

PROPERTIES

Physical Property

• Melting Point: 0 °C; 0-2°C; 0-2°C
• Boiling Point: 171-172 °C(lit.); 171-172°C; 171-172 °C; 171-172°C
• Flash Point: >100°C; >100°C(212°F)
• Density: 1.539; 1.539 g/cm^3; 1.539 g/ml; 1.539 g/mL at 25 °C(lit.)
• Refractive Index: 1.4700; 1.471; n20/D 1.471; n20/D 1.471(lit.)
• Vapor Pressure: 0.06 psi ( 20 °C)

Safety Information

• Storage Condition: 2-8°C
• Storage Warning: Moisture Sensitive; Toxic/Corrosive/Lachrymatory/Moisture Sensitive/Keep Cold/Store under Argon
• European Hazard Symbols: Corrosive (C); Flammable (F); Toxic (T)
• UN Number: 2742; 3277; UN3277
• German water hazard class: 3
• Hazard Class: 3/8; 6.1
• Packing Group: 2; II
• Australian Hazchem: 3W
• Risk Statements: 22-23-34; 23-34; R:10-22-34; R23, R34
• Safety Statements: 26-36/37/39-45; 9-20-26-36/37/39-45; S:16-26-27/28-36/37/39-46-64; S26, S36/37/39
• EU Classification: TFC
• EU Hazard Identification Number: 6.1A
• Emergency Response Guidebook(ERG) Number: 155
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H330-H314-H318; H314-H331
• GHS Precautionary statements: P260-P301+P310-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 3277 6.1/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (NT); 95%; 97%; 98%
• Grade: purum
• Linear Formula: ClCOOCH2CCl3

DETAILS

MP Biomedicals - 02156978

Purity: 95%
1 ml = approx. 1.54 g

Sigma Aldrich - 142077

Packaging
25, 100 g in glass bottle
Application
Protecting reagent for aliphatic and aromatic hydroxyl and amino groups.1

Sigma Aldrich - 23258

Other Notes
Protecting group reagent for amines and alcohols 1,2; Reagent for the demethylation of tert-amines3

REFERENCES

• Reagent for the protection of OH groups as their trichloroethyl (Troc) carbonates, specifically cleaved by reduction with zinc: Tetrahedron Lett., 2555 (1967). For a systematic study of the protection of amines as their Troc-carbamates, see: Synthesis, 268 (1981).
• Preferred to ethyl chloroformate for the N-demethylation of tert-amines, since the resulting carbamate can be cleaved by reductive elimination: Tetrahedron Lett., 1325 (1974); Synth. Commun., 7, 79 (1977).
• Effective reagent for dehydration of primary amides to nitriles: Synth. Commun., 30, 3047 (2000).
• For a brief survey of uses of this reagent in synthesis, see: Synlett, 1473 (2007).