Benzamide

Benzamide
Names
	Preferred IUPAC name Benzamide
	Systematic IUPAC name Benzenecarboxamide
	Other names Benzoic acid amide; Phenyl carboxamide; Benzoylamide
Identifiers
CAS Number	55-21-0 ;
3D model (JSmol)	Interactive image; Interactive image;
3DMet	B01116;
Beilstein Reference	385876
ChEBI	CHEBI:28179 ;
ChEMBL	ChEMBL267373 ;
ChemSpider	2241 ;
ECHA InfoCard	100.000.207
EC Number	200-227-7;
KEGG	C09815 ;
PubChem CID	2331;
RTECS number	CU8700000;
UNII	6X80438640 ;
CompTox Dashboard (EPA)	DTXSID0021709 ;
	show InChI
	show SMILES
Properties
Chemical formula	C7H7NO
Molar mass	121.139 g·mol−1
Appearance	Off-white solid
Density	1.341 g/cm3
Melting point	127 to 130 °C (261 to 266 °F; 400 to 403 K)
Boiling point	288 °C (550 °F; 561 K)
Solubility in water	13 g/l
Acidity (pKa)	approx. 13 (H2O); 23.3 (DMSO);
Magnetic susceptibility (χ)	-72.3·10−6 cm3/mol
Pharmacology
ATC code	N05AL (WHO)
Hazards
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H302, H341
GHS precautionary statements	P201, P202, P264, P270, P281, P301+312, P308+313, P330, P405, P501
NFPA 704 (fire diamond)	1 1 0
Flash point	180 °C (356 °F; 453 K)
Autoignition; temperature	> 500 °C (932 °F; 773 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	(what is ?)
	Infobox references

Benzamide is a white solid with the chemical formula of C₆H₅C(O)NH₂. It is the simplest amide derivative of benzoic acid. It is slightly soluble in water, and soluble in many organic solvents. A number of substituted benzamides are commercial drugs: sulpiride, remoxipride, amisulpride, tiapride, sultopride, veralipride, aminohippuric acid, cisapride, imatinib, and procainamide.

References[]

^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 841. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
^ Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–89. ISBN 978-1498754286.
^ Bordwell, Frederick G.; Ji, Guo Zhen (October 1991). "Effects of structural changes on acidities and homolytic bond dissociation energies of the hydrogen-nitrogen bonds in amidines, carboxamides, and thiocarboxamides". Journal of the American Chemical Society. 113 (22): 8398–8401. doi:10.1021/ja00022a029.

External links[]

[iupac2013-1] Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 841. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.

[CRC97-2] Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–89. ISBN 978-1498754286.

[3] Bordwell, Frederick G.; Ji, Guo Zhen (October 1991). "Effects of structural changes on acidities and homolytic bond dissociation energies of the hydrogen-nitrogen bonds in amidines, carboxamides, and thiocarboxamides". Journal of the American Chemical Society. 113 (22): 8398–8401. doi:10.1021/ja00022a029.

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[3]

show v t Antipsychotics (N05A)
Typical	Butyrophenones: Benperidol Bromperidol Droperidol Haloperidol^# Moperone Pipamperone Spiperone Timiperone Trifluperidol Diphenylbutylpiperidines: Fluspirilene Penfluridol Pimozide Phenothiazines: Acetophenazine Butaperazine Carphenazine (carfenazine)^‡ Chlorpromazine Cyamemazine Dixyrazine Fluphenazine Levomepromazine (methotrimeprazine) Mesoridazine Perazine Periciazine Perphenazine Piperacetazine Pipotiazine Prochlorperazine Promazine Sulforidazine Thiopropazate Thioproperazine Thioridazine Trifluoperazine Triflupromazine Thioxanthenes: Chlorprothixene Clopenthixol Flupentixol Tiotixene (thiothixene) Zuclopenthixol
Disputed	Benzamides: Amisulpride Levosulpiride Nemonapride Remoxipride^‡ Sulpiride Sultopride Tiapride Veralipride^‡ Butyrophenones: Melperone Tricyclics: Carpipramine Clocapramine Clorotepine Clotiapine Loxapine Mosapramine Others: Molindone
Atypical	Benzisoxazole/benzisothiazoles: Iloperidone Lurasidone Paliperidone Paliperidone palmitate Perospirone Risperidone^# Ziprasidone Butyrophenones: Lumateperone Phenylpiperazines/quinolinones: Aripiprazole Aripiprazole lauroxil Brilaroxazine^† Brexpiprazole Cariprazine Tricyclics: Asenapine Clozapine^# Olanzapine Quetiapine Zotepine Others: Blonanserin Pimavanserin Sertindole
Others	Azacyclonol Cannabidiol Oxypertine Reserpine Tetrabenazine
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

show v t Antiemetics (A04)
5-HT₃ serotonin ion channel antagonists	Alosetron Azasetron Bemesetron Cilansetron Clozapine Dazopride Dolasetron Granisetron Lerisetron Metoclopramide Mianserin Mirtazapine Olanzapine Ondansetron Palonosetron (+netupitant) Quetiapine Ramosetron Ricasetron Tropisetron Zatosetron
5-HT serotonin G-protein receptor antagonists	Clozapine Cyproheptadine Hydroxyzine Olanzapine Risperidone Ziprasidone
CB₁ agonists (cannabinoids)	Dronabinol Nabilone Tetrahydrocannabinol (cannabis)
D₂/D₃ antagonists	Alizapride Bromopride Chlorpromazine Clebopride Domperidone Haloperidol Hydroxyzine Itopride Metoclopramide Metopimazine Prochlorperazine Thiethylperazine Trimethobenzamide
H₁ antagonists (antihistamines)	Cyclizine Dimenhydrinate Diphenhydramine Hydroxyzine Meclizine Promethazine
mACh antagonists (anticholinergics)	Atropine Diphenhydramine Hydroxyzine (very mild) Hyoscyamine Scopolamine
NK₁ antagonists	Aprepitant Casopitant Ezlopitant Fosaprepitant Maropitant Netupitant Rolapitant Vestipitant
Others	Cerium oxalate Dexamethasone Lorazepam Midazolam Propofol

show Authority control
General	Integrated Authority File (Germany)
National libraries	United States
Other	Microsoft Academic

Names


Preferred IUPAC name Benzamide^[1]
Systematic IUPAC name Benzenecarboxamide
Other names Benzoic acid amide Phenyl carboxamide Benzoylamide
Identifiers
CAS Number	55-21-0^Y
3D model (JSmol)	Interactive image Interactive image
3DMet	B01116
Beilstein Reference	385876
ChEBI	CHEBI:28179^Y
ChEMBL	ChEMBL267373^Y
ChemSpider	2241^Y
ECHA InfoCard	100.000.207
EC Number	200-227-7
KEGG	C09815^Y
PubChem CID	2331
RTECS number	CU8700000
UNII	6X80438640^Y
CompTox Dashboard (EPA)	DTXSID0021709
show InChI InChI=1S/C7H7NO/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H2,8,9)^Y Key: KXDAEFPNCMNJSK-UHFFFAOYSA-N^Y InChI=1/C7H7NO/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H2,8,9) Key: KXDAEFPNCMNJSK-UHFFFAOYAA
show SMILES O=C(N)c1ccccc1 c1ccc(cc1)C(=O)N
Properties
Chemical formula	C₇H₇NO
Molar mass	121.139 g·mol⁻¹
Appearance	Off-white solid
Density	1.341 g/cm³
Melting point	127 to 130 °C (261 to 266 °F; 400 to 403 K)
Boiling point	288 °C (550 °F; 561 K)
Solubility in water	13 g/l
Acidity (pK_a)	approx. 13 (H₂O)^[2] 23.3 (DMSO)^[3]
Magnetic susceptibility (χ)	-72.3·10⁻⁶ cm³/mol
Pharmacology
ATC code	N05AL (WHO)
Hazards
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H302, H341
GHS precautionary statements	P201, P202, P264, P270, P281, P301+312, P308+313, P330, P405, P501
NFPA 704 (fire diamond)	1 1 0
Flash point	180 °C (356 °F; 453 K)
Autoignition temperature	> 500 °C (932 °F; 773 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y (what is ^YN ?)
Infobox references

Benzamide

See also[]

References[]

External links[]