3,5-Dinitrobenzoyl chloride

3,5-Dinitrobenzoyl chloride
	; 3,5-Dinitrobenzoyl chloride
Names
	Preferred IUPAC name 3,5-Dinitrobenzoyl chloride
Identifiers
CAS Number	99-33-2;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL2005426;
ChemSpider	7154;
ECHA InfoCard	100.002.500
EC Number	202-750-6;
PubChem CID	7432;
UNII	5JFA2DVM4D;
CompTox Dashboard (EPA)	DTXSID2059194 ;
	InChI InChI=1S/C7H3ClN2O5/c8-7(11)4-1-5(9(12)13)3-6(2-4)10(14)15/h1-3H Key: NNOHXABAQAGKRZ-UHFFFAOYSA-N;
	SMILES C1=C(C=C(C=C1[N+](=O)[O-])[N+](=O)[O-])C(=O)Cl;
Properties
Chemical formula	C7H3ClN2O5
Molar mass	230.56 g·mol−1
Melting point	68–69 °C (154–156 °F; 341–342 K)
Boiling point	196 °C (385 °F; 469 K) 11 mmHg
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H314
GHS precautionary statements	P260, P264, P280, P301+330+331, P303+361+353, P304+340, P305+351+338, P310, P321, P363, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

3,5-Dinitrobenzoyl chloride (C₇H₃ClN₂O₅) is an organic compound with a melting point of 68–69 °C.[1] It is the acyl chloride of 3,5-dinitrobenzoic acid and like it is mainly used in the analysis of organic substances by derivatization.[2]

Synthesis

3,5-dinitrobenzoyl chloride is prepared by the reaction of 3,5-dinitrobenzoic acid with phosphorus pentachloride, PCl₅.[3] It can likewise be prepared by reaction with phosphorus trichloride, PCl₃, or thionyl chloride, SOCl₂.[4]

Uses

3,5-Dinitrobenzoyl chloride has its main use in the analysis of organic compounds by derivatization, specifically of alcohols and amines. It is used in cases where the substance to be analyzed is sensitive and cannot be directly reacted with 3,5-dinitrobenzoic acid. Generally, the reaction is done in pyridine in order to bind the hydrogen chloride released.[5] With this method, it is for instance possible to identify amino acids.[3]

Identification of alanine via reaction with 3,5-dinitrobenzoyl chloride. The product has a melting point of 177 °C[6]

References

Sigma-Aldrich Co., 3,5-Dinitrobenzoyl chloride. Retrieved on 12. März 2017.
W. T. Robinson, R. H. Cundiff, P. C. Markunas: „Rapid Determination of Organic Hydroxyl Groups with 3,5-Dinitrobenzoyl Chloride“, in: Anal. Chem., 1961, 33 (8), S. 1030–1034 (doi:10.1021/ac60176a050).
Saunders, B. C.; Stacey, G. J.; Wilding, I. G. E. (1942). "The Preparation of 3:5-Dinitrobenzoic Acid and 3:5-Dinitrobenzoyl Chloride – Observations on the Acylation of Amino-acids by means of 3:5-Dinitrobenzoyl Chloride and certain other Acid Chlorides". Biochem. J. 36 (3–4): 368–375. doi:10.1042/bj0360368. PMC 1265703. PMID 16747534.
Organikum (in German) (19th ed.). Leipzig·Berlin·Heidelberg: Johann Ambrosius Barth. 1993. p. 440. ISBN 3335003438.
Organikum (in German) (19th ed.). Leipzig·Berlin·Heidelberg: Johann Ambrosius Barth. 1993. p. 424. ISBN 3335003438.
CRC Handbook of Tables for Organic Compound Identification, Third Edition, 1984, ISBN 0-8493-0303-6.

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[Sigma-1] Sigma-Aldrich Co., 3,5-Dinitrobenzoyl chloride. Retrieved on 12. März 2017.

[2] W. T. Robinson, R. H. Cundiff, P. C. Markunas: „Rapid Determination of Organic Hydroxyl Groups with 3,5-Dinitrobenzoyl Chloride“, in: Anal. Chem., 1961, 33 (8), S. 1030–1034 (doi:10.1021/ac60176a050).

[Saunders-3] Saunders, B. C.; Stacey, G. J.; Wilding, I. G. E. (1942). "The Preparation of 3:5-Dinitrobenzoic Acid and 3:5-Dinitrobenzoyl Chloride – Observations on the Acylation of Amino-acids by means of 3:5-Dinitrobenzoyl Chloride and certain other Acid Chlorides". Biochem. J. 36 (3–4): 368–375. doi:10.1042/bj0360368. PMC 1265703. PMID 16747534.

[4] Organikum (in German) (19th ed.). Leipzig·Berlin·Heidelberg: Johann Ambrosius Barth. 1993. p. 440. ISBN 3335003438.

[5] Organikum (in German) (19th ed.). Leipzig·Berlin·Heidelberg: Johann Ambrosius Barth. 1993. p. 424. ISBN 3335003438.

[CRC-6] CRC Handbook of Tables for Organic Compound Identification, Third Edition, 1984, ISBN 0-8493-0303-6.