Dinitrophenols

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2,4-dinitrophenol

The dinitrophenols ( DNP ) form a group of aromatic compounds that are derived from phenol as well as from nitrobenzene or dinitrobenzenes . The structure consists of a benzene ring with a hydroxyl group  (-OH) and two nitro groups  (-NO 2 ) as substituents . Their different arrangement results in six constitutional isomers with the empirical formula C 6 H 4 N 2 O 5 , with 2,4-dinitrophenol being the most important. The latter arises from o - and p -nitrophenol by re-nitriding. It is an intermediate product on the way to picric acid .

Dinitrophenols are very toxic and, if contaminated by inhalation, ingestion or contact, cause irritation of the eyes, the digestive tract, blood poisoning, liver damage, dizziness, nausea, headache and irritation of the respiratory tract. 2,4-Dinitrophenol in particular is said to be teratogenic, carcinogenic and mutagenic .

Dinitrophenols
Surname 2,3-dinitrophenol 2,4-dinitrophenol 2,5-dinitrophenol 2,6-dinitrophenol 3,4-dinitrophenol 3,5-dinitrophenol
Structural formula 2,3-dinitrophenol 2,4-dinitrophenol 2,5-dinitrophenol 2,6-dinitrophenol 3,4-dinitrophenol 3,5-dinitrophenol
CAS number 66-56-8 51-28-5 329-71-5 573-56-8 577-71-9 586-11-8
25550-58-7 (mixture of isomers)
PubChem 6191 1493 9492 11312 11348 11459
Molecular formula C 6 H 4 N 2 O 5
Molar mass 184.11 g mol −1
Physical state firmly
Brief description yellow, crystalline solids
Melting point 144-146 ° C 110-112 ° C 105 ° C 64 ° C 132-135 ° C 122; 126 ° C
pK s value 4.09 5.04 3.71 5.42
solubility soluble in water, soluble in ethanol, ether and chloroform
GHS
labeling
06 - Toxic or very toxic 08 - Dangerous to health 09 - Dangerous for the environment
danger
H and P phrases 331-311-301-373-410
no EUH phrases
261-273-280
301 + 310-311 		261-273-280
301 + 310-311 		261-273-280
301 + 310-311 		no P-phrases 261-273-280
301 + 310-311 		no P-phrases

Individual evidence

  1. ↑ a b Entry for CAS no. 25550-58-7 in the GESTIS substance database of the IFA , accessed on March 13, 2017(JavaScript required) .
  2. ↑ a b Entry on 2,3-Dinitrophenol in the GESTIS substance database of the IFA , accessed on March 13, 2017(JavaScript required) .
  3. ↑ a b Entry on 2,4-dinitrophenol in the GESTIS substance database of the IFA , accessed on March 13, 2017(JavaScript required) .
  4. ↑ a b Entry on 2,5-dinitrophenol in the GESTIS substance database of the IFA , accessed on March 13, 2017(JavaScript required) .
  5. ^ Entry on 2,6-Dinitrophenol in the GESTIS substance database of the IFA , accessed on March 13, 2017(JavaScript required) .
  6. ↑ a b Entry on 3,4-Dinitrophenol in the GESTIS substance database of the IFA , accessed on March 13, 2017(JavaScript required) .
  7. ↑ a b c d e CRC Handbook of Tables for Organic Compound Identification , Third Edition, 1984, ISBN 0-8493-0303-6 .
  8. ↑ Entry on 3,5-dinitrophenol in the GESTIS substance database of the IFA , accessed on March 13, 2017(JavaScript required) .

Web links

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