Picric acid

Picric acid
Names
	Preferred IUPAC name 2,4,6-Trinitrophenol
	Systematic IUPAC name 2,4,6-Trinitrobenzenol
	Other names Picric acid; Carbazotic acid; Phenol trinitrate; Picronitric acid; Trinitrophenol; 2,4,6-Trinitro-1-phenol; 2-Hydroxy-1,3,5-trinitrobenzene; TNP; Melinite; Lyddite
Identifiers
CAS Number	88-89-1 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:46149 ;
ChEMBL	ChEMBL108541 ;
ChemSpider	6688 ;
DrugBank	DB03651 ;
ECHA InfoCard	100.001.696
PubChem CID	6954;
RTECS number	TJ7875000;
UNII	A49OS0F91S ;
UN number	UN1344
CompTox Dashboard (EPA)	DTXSID4025909 ;
	InChI InChI=1S/C6H3N3O7/c10-6-4(8(13)14)1-3(7(11)12)2-5(6)9(15)16/h1-2,10H Key: OXNIZHLAWKMVMX-UHFFFAOYSA-N ; InChI=1/C6H3N3O7/c10-6-4(8(13)14)1-3(7(11)12)2-5(6)9(15)16/h1-2,10H Key: OXNIZHLAWKMVMX-UHFFFAOYAM;
	SMILES O=[N+]([O-])c1cc(cc([N+]([O-])=O)c1O)[N+]([O-])=O;
Properties
Chemical formula	C6H3N3O7
Molar mass	229.104 g·mol−1
Appearance	Colorless to yellow solid
Density	1.763 g/cm3, solid
Melting point	122.5 °C (252.5 °F; 395.6 K)
Boiling point	Sublimes above MP
Solubility in water	12.7 g/L
Solubility in sulfuric acid	10.18 g/100g sln. (18 °C (64 °F; 291 K)); 16.23 g/100g sln. (50 °C (122 °F; 323 K)); 25.86 g/100g sln. (80 °C (176 °F; 353 K)); (in 100% H2SO4)
Solubility in ethanol	7.452 g/100g
Solubility in diethyl ether	1.08 g/100g (13 °C (55 °F; 286 K))
Solubility in benzene	5.9 g/100g (15 °C (59 °F; 288 K))
Solubility in toluene	12.0 g/100ml (20 °C (68 °F; 293 K))
Solubility in amyl alcohol	1.755 g/100ml (20 °C (68 °F; 293 K))
log P	1.33
Vapor pressure	2 mmHg (0.27 kPa) (195 °C (383 °F; 468 K)); 50 mmHg (6.7 kPa) (255 °C (491 °F; 528 K));
Acidity (pKa)	0.38
Magnetic susceptibility (χ)	−84.34×10−6 cm3/mol
Structure
Crystal structure	Orthorhombic
Space group	Pca21
Lattice constant	a = 9.2596 Å, b = 19.138 Å, c = 9.7075 Å α = 90°, β = 90°, γ = 90°
Lattice volume (V)	1720.3 Å3
Formula units (Z)	8
Thermochemistry
Std enthalpy of; formation (ΔfH⦵298)	−215 kJ/mol
Enthalpy of fusion (ΔfH⦵fus)	20 kJ/mol
Enthalpy of vaporization (ΔfHvap)	88 kJ/mol
Explosive data
Shock sensitivity	65–93 cm (26–37 in) (Bureau of Mines test); 33 cm (13 in) (Picatinny Arsenal test); 4 g (62 gr) rifle bullet at more than 400 m/s (1,300 ft/s);
Friction sensitivity	Very slight (produces weak burning odor)
Detonation velocity	7,480 m/s (24,500 ft/s) at ρ=1.70
RE factor	1.12 (Ballistic mortar test); 1.01 (Trauzl test); 1.07 (Plate dent test);
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H228, H301+H311, H317, H332
Precautionary statements	P210, P240, P241, P261, P264, P270, P271, P272, P280, P301+P310+P330, P302+P352, P302+P352+P312, P304+P340+P312, P333+P313, P361, P363, P370+P378, P405, P501
NFPA 704 (fire diamond)	2 4 4
Flash point	150 °C; 302 °F; 423 K
Autoignition; temperature	300–310 °C (572–590 °F; 573–583 K) Burns after melting with sooty flame and characteristic whistling noise. (may explode if confined, contaminated with picrates, or in contact with metals that form picrates)
Threshold limit value (TLV)	0.1 mg/m3 (TWA)
	Lethal dose or concentration (LD, LC):
LDLo (lowest published)	100 mg/kg (guinea pig, oral); 250 mg/kg (cat, oral); 120 mg/kg (rabbit, oral);
	NIOSH (US health exposure limits):
PEL (Permissible)	0.1 mg/m3 (TWA, skin)
REL (Recommended)	0.1 mg/m3 (TWA); 0.3 mg/m3 (ST, skin);
IDLH (Immediate danger)	75 mg/m3
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Picric acid is an organic compound with the formula (O₂N)₃C₆H₂OH. Its IUPAC name is 2,4,6-trinitrophenol (TNP). The name "picric" comes from Greek: πικρός (pikros), meaning "bitter", due to its bitter taste. It is one of the most acidic phenols. Like other strongly nitrated organic compounds, picric acid is an explosive, which is its primary use. It has also been used as medicine (antiseptic, burn treatments) and as a dye.