2-hydroxybenzamide

Structural formula
General
Surname	2-hydroxybenzamide
other names	Salicylamide Salicylic acid amide o-hydroxybenzamide
Molecular formula	C 7 H 7 NO 2
Brief description	white to yellowish solid
External identifiers / databases
CAS number 65-45-2 EC number 200-609-3 ECHA InfoCard 100,000,554 PubChem 5147 ChemSpider 4963 DrugBank DB08797 Wikidata Q2496906
Drug information
ATC code	N02 BA05
properties
Molar mass	137.14 g mol −1
Physical state	firmly
density	1.175 g cm −3
Melting point	138-142 ° C
boiling point	181 ° C (19 hPa)
solubility	soluble in water (2.06 g / l at 25 ° C) soluble in chloroform, dimethyl sulfoxide, ethanol and methanol Easily soluble in alkali hydroxide solutions
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS labeling of hazardous substances Caution H and P phrases H: 302-411 P: 261-305 + 351 + 338
Toxicological data	980 mg kg −1 ( LD 50 ,  rat ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2-Hydroxybenzamide is a chemical compound from the group of substituted phenols .

Extraction and presentation

2-Hydroxybenzamide can be obtained by ammonolysis of methyl salicylate . A regulation for implementation in the case of slight overpressure, for example during an internship, can be found in the literature.

properties

2-Hydroxybenzamide is a flammable, difficult to ignite, crystalline, white to yellowish solid. It has a monoclinic crystal structure with the space group C 2 / c (space group no. 15) . Other crystal structures are also known at high pressure.

use

2-Hydroxybenzamide is used in combination with aspirin and caffeine in over-the-counter pain relievers. It is used as both an analgesic and an antipyretic . In solution in ethanol it also serves as a metal hole chrome indicator in the detection of iron (III). It has little anti-rheumatic effect. Salicylamide is converted to gentisinamide to 20% in the body. 70% of the salicylic acid derivative is excreted in the urine coupled with glucuronic acid .

Individual evidence

1. ↑ ^{a b c d e f g} Entry on 2-hydroxybenzamide in the GESTIS substance database of the IFA , accessed on November 3, 2018(JavaScript required) .
2. ↑ David R. Lide: CRC Handbook of Chemistry and Physics A Ready-reference Book of Chemical and Physical Data . CRC Press, 1995, ISBN 978-0-8493-0595-5 , pp. 316 ( limited preview in Google Book Search).
3. ↑ ^{a b c} Data sheet salicylamides, 98% from AlfaAesar, accessed on November 3, 2018 ( PDF )(JavaScript required) .
4. ↑ basg.gv.at: Salicylamid , April 17, 2015, accessed on November 3, 2018
5. ↑ Data sheet Salicylamide, puriss., ≥99.0% (T) from Sigma-Aldrich , accessed on November 3, 2018 ( PDF ).
6. ↑ Entry on 2-hydroxybenzamide in the Hazardous Substances Data Bank , accessed on November 3, 2018.
7. ↑ Dr. Eric Täuscher: Small synthesis corner. In: Internship in Biotechnical Chemistry TU-Ilmenau, OC-1. Techniche Universität Ilmenau, accessed on June 11, 2020 (German). 
8. ↑ Yoshio Sasada, Tsunehiro Takano, Masao Kakudo: Crystal Structure of Salicylamide. In: Bulletin of the Chemical Society of Japan. 37, 1964, p. 940, doi : 10.1246 / bcsj.37.940 .
9. ^ Russell DL Johnstone, Alistair R. Lennie et al. a .: High-pressure polymorphism in salicylamide. In: CrystEngComm. 12, 2010, p. 1065, doi : 10.1039 / B921288D .
10. ^ Karl-Heinz Beyer: Biotransformation der Arzneimittel . Springer-Verlag, 2013, ISBN 978-3-642-74386-3 , pp. 493 ( limited preview in Google Book search).
11. ↑ A. Townshend, DT Burns, Ryszard Lobinski, EJ Newman, G. Guilbault, Z. Marczenko, H. Onishi: Dictionary of Analytical Reagents . CRC Press, 1993, ISBN 978-0-412-35150-1 , pp. 541 ( limited preview in Google Book search).
12. ↑ Lexicon of Biology: Salicylamide - Lexicon of Biology , accessed on November 3, 2018.