oxalic dichloride

• ChemBase ID: 78496
• Molecular Formular: C2Cl2O2
• Molecular Mass: 126.9262
• Monoisotopic Mass: 125.9275346
• SMILES: ClC(=O)C(=O)Cl
• Canonical SMILES: ClC(=O)C(=O)Cl
• InChI: InChI=1S/C2Cl2O2/c3-1(5)2(4)6
• InChIKey: CTSLXHKWHWQRSH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: oxalic dichloride
• IUPAC Traditional name: oxalyl chloride
• Synonyms: oxalyl dichloride; Oxalyl chloride; Ethanedioyl dichloride; Oxalyl chloride; Oxalyl chloride solution; Oxalic acid chloride; Oxalic acid dichloride; Oxalyl dichloride; Oxalic dichloride; Oxaloyl chloride; 乙二酰二氯; 草酰氯; 草酰氯 溶液

Database IDs

• CAS Number: 79-37-8
• EC Number: 201-200-2
• MDL Number: MFCD00000704
• Beilstein Number: 1361988
• Merck Index: 146914
• PubChem SID: 24886877; 162043262; 24858810; 24859263; 24898062; 24853204
• PubChem CID: 65578
• Chemspider ID: 59021
• Wikipedia Title: Oxalyl_chloride

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.8029077
• LogD (pH = 7.4): 0.8029077
• Log P: 0.8029077
• Molar Refractivity: 22.1556 cm^3
• Polarizability: 8.683687 Å^3
• Polar Surface Area: 34.14 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Decomposes in water
• Apperance: APHA: 0-150; colorless liquid
• Melting Point: -10--8 °C(lit.); -12°C; -12°C; -16°C; 63-64°C @ 763 mm
• Boiling Point: -12°C; 62-65 °C(lit.); 63 - 64°C (1.017 bar); 63-64°C; 63-64°C
• Density: 1.335 g/mL at 25 °C; 1.455; 1.455 g/ml; 1.4785 g/mL, liquid; 1.48; 1.5 g/mL at 20 °C(lit.)
• Refractive Index: 1.429; 1.4290; n20/D 1.429(lit.)
• Vapor Pressure: 150 mmHg ( 20 °C)
• Vapor Density: 4.4 (vs air)

Safety Information

• Storage Condition: 2-8°C, Desiccate
• Storage Warning: Moisture Sensitive; Toxic/Corrosive/Lachrymatory/Moisture Sensitive/Store under Argon
• RTECS: KI2950000
• European Hazard Symbols: Corrosive (C); Toxic (T)
• UN Number: 2922; 2927; UN2927
• German water hazard class: 2
• Hazard Class: 6.1; 8
• Packing Group: 1; 2; II
• Australian Hazchem: 2XE
• Risk Statements: 14-22-23-29-34; 14-23-29-34; 14-23-29-34-37; 14-23-29-34-37-40; R:14-22-34
• Safety Statements: 26-36/37/39-45; 4-7/8-9-20-23-26-30-36/37/39-45-60; S:27/28-30-36/37/39-45
• EU Classification: CT1
• EU Hazard Identification Number: 8B
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS06; GHS07; GHS08
• GHS Signal Word: Danger
• NFPA704:
  

  3

  1
• GHS Hazard statements: H314-H331; H314-H331-H335; H314-H332-H335-H351; H331-H302-H314-H318
• GHS Precautionary statements: P261-P280-P305 + P351 + P338-P310; P280-P303+P361+P353-P305+P351+P338-P310-P402+P404
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US); Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2922 8/PG 1; UN 2927 6.1/PG 2
• Supplemental Hazard Statements: Contact with water liberates toxic gas., Reacts violently with water.

Product Information

• Purity: ≥96.0% (AT); ≥99%; 98%
• Concentration: ~2 M in methylene chloride; 2.0 M in methylene chloride
• Grade: purum; reagent grade; ReagentPlus®
• Impurities: <10 ppb Heavy metals; ≤1.0% phosgene content
• Quality: dist.
• Linear Formula: ClCOCOCl

DETAILS

MP Biomedicals - 02156012

1 ml = approx. 1.48 g

Sigma Aldrich - 75760

Packaging
2.5 kg in glass bottle
25, 100, 500 mL in glass bottle
Application
Reactant involved in:
• Synthesis of N-heterocyclic ynones and ynediones, used to activate carboxylic acids1
• Chlorination and halogenation2
• Three-component [3+2] cycloadditions3
• Reactions with organostannanes4
• Synthesis of cyclopentenones5
• Carbonylations, used as a carbonyl synthon6

Sigma Aldrich - 310670

Packaging
100, 800 mL in Sure/Seal™

Sigma Aldrich - 320420

Packaging
1 L in PVC coated
Application
Reactant involved in:
• Synthesis of N-heterocyclic ynones and ynediones, used to activate carboxylic acids1
• Chlorination and halogenation2
• Three-component [3+2] cycloadditions3
• Reactions with organostannanes4
• Synthesis of cyclopentenones5
• Carbonylations, used as a carbonyl synthon6

Sigma Aldrich - 77514

Application
Reactant involved in:
• Synthesis of N-heterocyclic ynones and ynediones, used to activate carboxylic acids1
• Chlorination and halogenation2
• Three-component [3+2] cycloadditions3
• Reactions with organostannanes4
• Synthesis of cyclopentenones5
• Carbonylations, used as a carbonyl synthon6

Sigma Aldrich - O8801

Packaging
1, 2.5 kg in glass bottle
25, 100 g in glass bottle
Application
Reactant involved in:
• Synthesis of N-heterocyclic ynones and ynediones, used to activate carboxylic acids1
• Chlorination and halogenation2
• Three-component [3+2] cycloadditions3
• Reactions with organostannanes4
• Synthesis of cyclopentenones5
• Carbonylations, used as a carbonyl synthon6

Sigma Aldrich - 221015

Application
Suitable for the synthesis of acid chlorides used to produce liquid crystals.
Reactant involved in:
• Synthesis of N-heterocyclic ynones and ynediones, used to activate carboxylic acids1
• Chlorination and halogenation2
• Three-component [3+2] cycloadditions3
• Reactions with organostannanes4
• Synthesis of cyclopentenones5
• Carbonylations, used as a carbonyl synthon6
Packaging
5, 25, 100 g in ampule
Legal Information
ReagentPlus is a registered trademark of Sigma-Aldrich Co. LLC

REFERENCES

• Friedel-Crafts reaction with arenes give carboxylic acids via the acid chlorides; see, e.g.: Org. Synth. Coll., 5, 706 (1973); 7, 420 (1990). For other phosgene equivalents, see Trichloromethyl chloroformate, A17444, and Triphosgene, A14932.
• Widely used to activate Dimethyl sulfoxide, A13280, for selective oxidation of alcohols to aldehydes or ketones (Swern oxidation) at low temperatures under very mild conditions: J. Org. Chem., 43, 2480 (1978). The reactive species is thought to be chlorodimethylsulfonium chloride: J. Org. Chem., 44, 4148 (1979). For examples of Swern oxidations, see: Org. Synth. Coll., 7, 258 (1990); 8, 501 (1993); 9, 692 (1998); Org. Synth., 76, 110 (1998). See also Trifluoroacetic anhydride, A13614.
• Has advantages over POCl₃ in the Vilsmeier formylation reaction in that cleaner reactions often occur and a much lower mass of acidic by-product is formed. See N,N-Dimethylformamide, A13547 and (Chloromethylene)dimethylammonium chloride, B24172.
• Reaction with Grignards in the presence of LiBr and CuBr provides a route to symmetrical ɑ-diones in good yield: Tetrahedron Lett., 36, 7305 (1995).
• For a brief feature on uses of this reagent in Organic synthesis, see: Synlett, 1172 (2007).
• Reactive acid chloride which can be used as a phosgene substitute in many reactions.
• Caution! Carbon monoxide may be evolved.
• Mild reagent for conversion of sensitive acids to acid chlorides; see, e.g.: Org. Synth. Coll., 8, 486 (1993); Org. Synth. Coll., 9, 516 (1998).