CAS 79-37-8|Oxalic acid dichloride|Oxaloyl chloride|Ethanedioyl dichloride|Oxalic dichloride|Oxalyl chloride solution|Oxalyl dichloride|草酰氯溶液|oxalic dichloride|Oxalyl chloride|乙二酰二氯|Oxaly...

General Information

Structure

Molecular Formula

C₂Cl₂O₂

Molecular Mass

126.9262

Exact Mass

125.9275346

Charge

InChI

InChI=1S/C2Cl2O2/c3-1(5)2(4)6

InChIKey

CTSLXHKWHWQRSH-UHFFFAOYSA-N

Canonic Smiles

ClC(=O)C(=O)Cl

Isomeric Smiles

ClC(=O)C(=O)Cl

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

0.8029077

LogD (pH = 7.4)

0.8029077

Log P

0.8029077

Molar Refractivity

22.1556

Polarizability

8.683687

Polar Surface Area

34.14

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

Synonyms

Oxalic acid dichlorideEthanedioyl dichlorideOxaloyl chlorideOxalic dichlorideOxalyl chloride solutionOxalyl dichlorideOxalyl chloride草酰氯溶液乙二酰二氯草酰氯Oxalyl chlorideOxalic acid chlorideoxalyl dichloride

IUPAC name

oxalic dichloride

IUPAC Traditional name

oxalyl chloride

Names and Identifiers

Registration numbers

Beilstein Number

1361988

MDL Number

MFCD00000704

PubChem SID

2485320424858810162043262248592632489806224886877

CAS Number

EC Number

Merck Index

PubChem CID

Chemspider ID

Wikipedia Title

Registration numbers

Properties

Safety Information

Toxic/Corrosive/Lachrymatory/Moisture Sensitive/Store under Argon

Moisture Sensitive

Toxic (T)

Properties

Related Proteins

No Data Available

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Molecular Spectra

Molecule Details

MP Biomedicals

02156012

1 ml = approx. 1.48 g

Wikipedia

Oxalyl_chloride

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

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

310670

Packaging
100, 800 mL in Sure/Seal™

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

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

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

Molecule Details

References

PubChem Literature

From Data Sources

• 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).

• For a brief feature on uses of this reagent in Organic synthesis, see: Synlett, 1172 (2007).

• 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.

• 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.

• Caution! Carbon monoxide may be evolved.

• 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.

• Reactive acid chloride which can be used as a phosgene substitute in many reactions.

• 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).

References

Bioactivity

PubChem BioAssay

Bioactivity

Registration numbers

Beilstein Number

1361988

MDL Number

MFCD00000704

PubChem SID

2485320424858810162043262248592632489806224886877

CAS Number

EC Number

Merck Index

PubChem CID

Chemspider ID

Wikipedia Title

References

PubChem Literature

From Data Sources

• 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).

• For a brief feature on uses of this reagent in Organic synthesis, see: Synlett, 1172 (2007).

• Caution! Carbon monoxide may be evolved.

• Reactive acid chloride which can be used as a phosgene substitute in many reactions.

• 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).

Bioactivity

PubChem BioAssay