88-89-1

Basic information

• Product Name: 2,4,6-Trinitrophenol
• Synonyms: Picric acid(6CI,8CI);1-Hydroxy-2,4,6-trinitrobenzene;2,4,6-Trinitrophenol;C.I. 10305;Carbazotic acid;Melinite;NSC 36947;NSC 56147;Nitroxanthic acid;Picral;Picronitric acid;Trinitrophenol
• CAS NO: 88-89-1
• Molecular Formula: C₆H₃N₃O₇
• Molecular Weight: 229.12
• EINECS: 201-865-9
• Mol File: 88-89-1.mol
• Article Data: 62

Chemical Properties

• Melting Point: 122-123℃
• Boiling Point: 303.6 °C at 760 mmHg
• Flash Point: 133.9 °C
• Appearance: Yellow solid
• Density: 1.856 g/cm³
• Vapor Density: 0.62 (vs air)
• Vapor Pressure: 2.3 kPa (@ 20°C)
• Water Solubility: Soluble in water
• CAS DataBase Reference: 2,4,6-Trinitrophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-Trinitrophenol(88-89-1)
• EPA Substance Registry System: 2,4,6-Trinitrophenol(88-89-1)

Safety Data

• Hazard Codes: F:Flammable;;
• Statements: R1:; R4:; R11:; R23/24/25:
• Safety Statements: S25:; S36/37:; S45:
• RIDADR: 0154
• HazardClass: 1.1D
• Hazardous Substances Data: 88-89-1(Hazardous Substances Data)

Usage

General Description

2,4,6-Trinitrophenol, also known as picric acid, is a highly explosive and toxic chemical compound with the molecular formula C6H3N3O7. It is a yellow crystalline solid that is commonly used in the production of dyes, explosives, and as a chemical reagent. Picric acid is highly reactive and is classified as a primary high explosive, meaning it can detonate under a wide range of conditions. It is also considered toxic and can cause severe skin irritation, respiratory issues, and liver damage upon exposure. Due to its hazardous properties, picric acid is typically handled and stored with extreme care and is often substituted with safer alternatives in industrial applications.

InChI:InChI=1/C6H3N3O7/c10-6-4(8(13)14)1-3(7(11)12)2-5(6)9(15)16/h1-2,10H

Synthetic route

(imidazole-1-yl)-2,4,6-trinitrobenzene (23309-22-0) → 2,4,6-Trinitrophenol (88-89-1)

Conditions	Yield
With water	100%

2,4,6-trinitrochlorobenzene (88-88-0) + sodium methylate (124-41-4) + acetylacetone (123-54-6) → 2,4,6-Trinitrophenol (88-89-1) + 1-methoxy-2,4,6-trinitrobenzene (606-35-9) + 3-(2,4,6-trinitrophenyl)-2,4-pentanedione (87687-98-7)

Conditions	Yield
In methanol; dimethyl sulfoxide at 25℃; Rate constant; Mechanism;	A 1% B 1% C 96%

S,S'-bis(2,4,6-trinitrophenyl) dithiooxalate (37590-58-2) → 2,4,6-Trinitrophenol (88-89-1)

Conditions	Yield
With nitric acid	95%
With nitric acid for 1h; Product distribution;
Multi-step reaction with 2 steps 1: conc. HNO3 / 25 - 30 °C 2: 91 percent / H2O, H2SO4 / 4 h / 50 °C View Scheme

2,4,6-trinitrochlorobenzene (88-88-0) + sodium methylate (124-41-4) + acetoacetic acid methyl ester (105-45-3) → 2,4,6-Trinitrophenol (88-89-1) + methyl 2-(2,4,6-trinitrophenyl)-3-oxobutanoate (87687-99-8)

Conditions	Yield
In methanol at 25℃; Rate constant; Mechanism;	A n/a B 94%

phenol (108-95-2) → 2,4,6-Trinitrophenol (88-89-1) + p-benzoquinone (106-51-4)

Conditions	Yield
With NO+*18-crown-6*H(NO3)2- In various solvent(s) for 2h; Nitration; Heating;	A 94% B 5%
With Zn(NO3)2*2N2O4 In ethyl acetate at 20℃; for 0.25h;	A 86% B 8%

1,2,3,5-tetranitrobenzene (3698-53-1) → 4,6-dinitrobenzofuroxan (5128-28-9) + 2,4,6-Trinitrophenol (88-89-1)

Conditions	Yield
With hydroxylamine hydrochloride; sodium acetate In methanol at 45 - 50℃; for 1h;	A 93% B n/a

2,4,6-trinitrochlorobenzene (88-88-0) + 2,4-dinitrophenylhydroxylamine potassium salt → 2,4,6-Trinitrophenol (88-89-1) + 5-nitrobenzofuroxane (3702-88-3)

Conditions	Yield
In methanol at 20℃; for 0.5h;	A n/a B 92%

2,4,6-trinitronitrosobenzene (10123-09-8) → 2,4,6-Trinitrophenol (88-89-1)

Conditions	Yield
With sulfuric acid; water at 50℃; for 4h;	91%

4-nitro-phenol (100-02-7) → 2,4,6-Trinitrophenol (88-89-1)

Conditions	Yield
With Zn(NO3)2*2N2O4 In dichloromethane for 0.583333h; Heating;	90%
With nitric acid

2,4,6-trinitrochlorobenzene (88-88-0) + 2,6-dinitrophenylhydroxylamine potassium salt → 2,4,6-Trinitrophenol (88-89-1) + 4-nitrobenzofuroxan (18771-85-2)

Conditions	Yield
In methanol at 20℃; for 0.5h;	A n/a B 88%

phenol (108-95-2) → 2,4,6-Trinitrophenol (88-89-1)

Conditions	Yield
With nitric acid In dimethyl sulfoxide at 100℃; for 4h;	87%
With copper(II) nitrate trihydrate In acetonitrile at 70℃; for 20h; Inert atmosphere; Irradiation;	75%
technische Herstellung durch Sulfonierung und anschl. Nitrierung;

2-hydroxynitrobenzene (88-75-5) → 2,4,6-Trinitrophenol (88-89-1)

Conditions	Yield
With Zn(NO3)2*2N2O4 In dichloromethane for 1.5h; Heating;	86%
With nitric acid

phenol (108-95-2) → 2,4-Dinitrophenol (51-28-5) + 2,4,6-Trinitrophenol (88-89-1) + p-benzoquinone (106-51-4)

Conditions	Yield
With NO+*18-crown-6*H(NO3)2- In ethyl acetate for 0.166667h; Nitration; Heating;	A 82% B 8% C 3%
With silica-acetate; dinitrogen tetraoxide In ethyl acetate for 0.166667h; Heating;	A 74% B 8% C 10%

phenylboronic acid (98-80-6) → 2,4,6-Trinitrophenol (88-89-1)

Conditions	Yield
With dipotassium peroxodisulfate; copper(II) nitrate trihydrate In acetonitrile at 70℃; for 20h; Reagent/catalyst; Solvent; Temperature; Time; Inert atmosphere; Irradiation; Green chemistry;	78%

9-acetoxy-10-(4'-acetoxyphenyl)-anthracene (57374-14-8) → 9,10-phenanthrenequinone (84-65-1) + 2,4,6-Trinitrophenol (88-89-1) + 10-hydroxy-10-(3',5'-dinitro-4'-hydroxyphenyl)anthrone-9 (85773-94-0)

Conditions	Yield
With nitric acid In acetic acid at 105 - 110℃; for 0.25h;	A 75% B 75% C 10%

2-nitrophenylboronic acid (5570-19-4) → 2,4,6-Trinitrophenol (88-89-1)

Conditions	Yield
With dipotassium peroxodisulfate; copper(II) nitrate trihydrate In acetonitrile at 70℃; for 20h; Inert atmosphere; Irradiation; Green chemistry;	70%

1-methyl-2-nitrobenzene (88-72-2) → ortho-nitrobenzoic acid (552-16-9) + 2,4,6-Trinitrophenol (88-89-1)

Conditions	Yield
With nitric acid at 170℃; for 0.333333h;	A 66% B 21%
With nitric acid at 170℃; for 0.25h; Product distribution; variation of temperature, reaction time, concentration of nitric acid, proportion of nitric acid;	A 63% B 18%
With nitric acid at 170℃; for 0.333333h;	A 55% B 25%
With nitric acid at 180 - 185℃; under 11400 Torr;

2-nitro-benzaldehyde (552-89-6) → ortho-nitrobenzoic acid (552-16-9) + 2,4,6-Trinitrophenol (88-89-1)

Conditions	Yield
With nitric acid at 160 - 170℃; for 0.0833333h;	A 65% B 25%

2,4-Dinitrophenol (51-28-5) → 2,4,6-Trinitrophenol (88-89-1)

Conditions	Yield
With nitric acid	60%
With sulfuric acid; nitric acid anfangs bei Raumtemperatur, zuletzt bei 65grad;
With nitric acid

picryl bromide (4185-53-9) → 1,3,5-trinitrobenzene (99-35-4) + m-Anisidine (536-90-3) + 2,4,6-Trinitrophenol (88-89-1)

Conditions	Yield
With copper In nitrobenzene for 9h; Product distribution; Irradiation; other solvent, var. time;	A 51% B 27% C n/a

1,3,5-trinitrobenzene (99-35-4) → 2,4,6-Trinitrophenol (88-89-1)

Conditions	Yield
With Cumene hydroperoxide; potassium tert-butylate In N,N,N,N,N,N-hexamethylphosphoric triamide at -5 - 5℃; for 0.25h;	50%
With sodium carbonate; potassium hexacyanoferrate(III)

2,4,6-tribromophenol (118-79-6) → bromine (7726-95-6) + 2,4,6-Trinitrophenol (88-89-1)

Conditions	Yield
With nitric acid	A 50% B n/a
With nitric acid	A >99 B n/a

N-butyl-2,4,6-trinitroaniline (32902-85-5) → 2,4,6-Trinitrophenol (88-89-1) + 5,7-dinitro-2-propyl-1H-benzimidazole 3-oxide

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water for 18h; Heating;	A 10.4% B 46.3%

9-acetoxy-10-(4'-acetoxyphenyl)-anthracene (57374-14-8) → 10-hydroxy-10-(4'-hydroxyphenyl)anthrone-9 (7477-15-8) + 9,10-phenanthrenequinone (84-65-1) + 2,4,6-Trinitrophenol (88-89-1) + 10-hydroxy-10-(3',5'-dinitro-4'-hydroxyphenyl)anthrone-9 (85773-94-0)

Conditions	Yield
With nitric acid In acetic acid at 90 - 95℃; for 0.0833333h; Mechanism; Product distribution; other 9-acetoxyanthracene derivatives, other temperatures;	A 10% B 30% C 30% D 20%
With nitric acid In acetic acid at 90 - 95℃; for 0.0833333h;	A 10% B 30% C 30% D 20%

N-(2,4,6-trinitrophenyl)acetamide (16400-86-5) → picramide (489-98-5) + 2,4,6-Trinitrophenol (88-89-1) + 1,2,3,5-tetranitrobenzene (3698-53-1)

Conditions	Yield
With sulfuric acid; ozone for 72h; Ambient temperature;	A 5% B n/a C 29%

copper picrate tetrahydrate → 2,4,6-Trinitrophenol (88-89-1)

Conditions	Yield
With 2,2'-[1,1'-(ethylenedioxydinitrilo)diethylidyne]diphenol In acetone for 1461h;	25.9%

2-thiazolylamine (96-50-4) + 1-methoxy-2,4,6-trinitrobenzene (606-35-9) → 2-N-(2,4,6-trinitrophenyl)thiazoleamine (132666-70-7) + [3-Methyl-3H-thiazol-(2Z)-ylidene]-(2,4,6-trinitro-phenyl)-amine (132666-77-4) + 2,4,6-Trinitrophenol (88-89-1)

Conditions	Yield
With sodium acetate In methanol	A n/a B 20% C 20%

4-methylthiazol-2-ylamine (1603-91-4) + 1-methoxy-2,4,6-trinitrobenzene (606-35-9) → 2-N-(2,4,6-trinitrophenyl)-4-methylthiazoleamine (68557-44-8) + [3,4-Dimethyl-3H-thiazol-(2Z)-ylidene]-(2,4,6-trinitro-phenyl)-amine (132666-78-5) + 2,4,6-Trinitrophenol (88-89-1)

Conditions	Yield
With sodium acetate In methanol	A n/a B 20% C 20%

o-hydroxyacetophenone (118-93-4) → 2,4,6-Trinitrophenol (88-89-1)

Conditions	Yield
With nitric acid In acetic acid at 100℃; for 0.5h;	20%

morpholine-4-carboxylic acid amide (2158-02-3) + 2,4,6-Trinitrophenol (88-89-1) → Picric acid; compound with morpholine-4-carboxylic acid amide (87448-69-9)

Conditions	Yield
In hexane; isopropyl alcohol Heating;	100%
	78%

Te,Te-di(p-methoxyphenyl)-N-(p-tolylsulfonyl)tellurimide (62486-35-5) + 2,4,6-Trinitrophenol (88-89-1) → bis oxide (107590-69-2)

Conditions	Yield
In diethyl ether; dichloromethane for 0.5h;	100%

N-(p-tolylsulfonyl)diphenyltellurimide (78727-83-0) + 2,4,6-Trinitrophenol (88-89-1) → toluene-4-sulfonamide (70-55-3) + bis oxide (107590-68-1)

Conditions	Yield
In diethyl ether; dichloromethane for 0.5h;	A 78% B 100%

2,4,6-Trinitrophenol (88-89-1) + N-(trifluoroacetyl)-di(p-methoxyphenyl)tellurimide (77571-23-4, 78780-20-8, 78780-21-9) → bis oxide (107590-69-2)

Conditions	Yield
In diethyl ether; dichloromethane for 0.5h;	100%

2,4,6-Trinitrophenol (88-89-1) + (Z)-3-(pyrrolidin-1-ylmethylene)-3H-indole (75629-45-7) → 3-(1-pyrrolidinylmethylene)-3H-indolium picrate (75629-53-7)

Conditions	Yield
In ethanol Ambient temperature;	100%

2,4,6-Trinitrophenol (88-89-1) + S-Methyl-<2,4-bis-ethylamino-1,3,5-triazin-6-yl>-isothiuronium-methoiodid → S-Methyl-<2,4-bis-ethylamino-1,3,5-triazin-6-yl>-isothiuroniumpikrat

Conditions	Yield
In water	100%

2,4,6-Trinitrophenol (88-89-1) + S-Methyl-<2-ethylamino-4-isopropylamino-1,3,5-triazin-6-yl>-isothiuronium-methoiodid → S-Methyl-<2-ethylamino-4-isopropylamino-1,3,5-triazin-6-yl>-isothiuroniumpikrat

Conditions	Yield
In water	100%

2,4,6-Trinitrophenol (88-89-1) + S-Methyl-<2,4-bis-isopropylamino-1,3,5-triazin-6-yl>-isothiuronium-methoiodid → S-Methyl-<2,4-bis-isopropylamino-1,3,5-triazin-6-yl>-isothiuroniumpikrat

Conditions	Yield
In water	100%

tetraethylammonium chloride (56-34-8) + 2,4,6-Trinitrophenol (88-89-1) → tetraethylammonium picrate (741-03-7)

Conditions	Yield
With 2-chloropyridine In acetonitrile Product distribution; without reagent;	100%

2,4,6-Trinitrophenol (88-89-1) + 4-(2-Benzyl-aziridin-1-yl)-5-methoxy-[1,2]benzoquinone (179805-77-7) → 4-Methoxy-5-[3-phenyl-2-(2,4,6-trinitro-phenoxy)-propylamino]-[1,2]benzoquinone

Conditions	Yield
In acetonitrile at 50℃; for 0.0833333h;	100%

C10H13N5O4 (1015842-84-8) + 2,4,6-Trinitrophenol (88-89-1) → C6H3N3O7*C10H13N5O4 (1015842-86-0)

Conditions	Yield
In methanol; water	100%

C87H123N7O9 (1336893-26-5) + 2,4,6-Trinitrophenol (88-89-1) → C6H3N3O7*C87H123N7O9 (1336893-27-6)

Conditions	Yield
In chloroform-d1 Inert atmosphere;	100%

C32H28N4O4*C46H52N4O3 + 2,4,6-Trinitrophenol (88-89-1) → C32H28N4O4*C46H52N4O3*C6H3N3O7

Conditions	Yield
In chloroform	100%

C35H31N3O2*C32H28N4O4 + 2,4,6-Trinitrophenol (88-89-1) → C32H28N4O4*C35H31N3O2*C6H3N3O7

Conditions	Yield
In chloroform	100%

C46H52N4O3 + 2,4,6-Trinitrophenol (88-89-1) → C46H52N4O3*C6H3N3O7

Conditions	Yield
In chloroform	100%

2,4,6-Trinitrophenol (88-89-1) + C12H16N2OS (95213-58-4) → α-morpholinobenzylideneamine picrate (52460-55-6)

Conditions	Yield
In ethanol for 2h; Ambient temperature;	99%

pentaphenylantimony (2170-05-0) + 2,4,6-Trinitrophenol (88-89-1) → (2,4,6-trinitrophenoxy)tetraphenylantimony (126858-87-5, 209054-82-0)

Conditions	Yield
In toluene room temperature;	99%

1,2,3-trimethylimidazolium hydrogen carbonate (1227510-75-9) + 2,4,6-Trinitrophenol (88-89-1) → 1,2,3-trimethylimidazolium picrate (941584-22-1)

Conditions	Yield
In ethanol; water at 20℃; for 24h;	98%

N,N-dimethylpyrrolidinium hydrogen carbonate (1227510-78-2) + 2,4,6-Trinitrophenol (88-89-1) → N,N-dimethylpyrrolidinium picrate (108565-31-7)

Conditions	Yield
In ethanol; water at 20℃; for 24h;	98%

1-methyl-1H-imidazole (616-47-7) + 2,4,6-Trinitrophenol (88-89-1) → 1-methylimidazolium picrate (6314-33-6, 22683-11-0)

Conditions	Yield
In ethanol; water at 40℃; for 10h;	98%

1,2-dimethyl-1H-imidazole (1739-84-0) + 2,4,6-Trinitrophenol (88-89-1) → 1,2-dimethylimidazole*2,4,6-trinitrophenol (24134-14-3)

Conditions	Yield
In ethanol; water at 40℃; for 10h;	98%

1-Butylimidazole (4316-42-1) + 2,4,6-Trinitrophenol (88-89-1) → 1-butyl-1H-imidazole; picrate (107054-84-2)

Conditions	Yield
In ethanol; water at 40℃; for 10h;	98%

2,4,6-Trinitrophenol (88-89-1) + 1-butyl-2-methyl-1H-imidazole (13435-22-8) → 1-butyl-2-methylimidazolium picrate (40229-82-1)

Conditions	Yield
In ethanol; water at 40℃; for 10h;	98%

heptakis(6-guanidino-6-deoxy)-β-CD hydrochloride + 2,4,6-Trinitrophenol (88-89-1) → 7C6H3N3O7*C49H91N21O28

Conditions	Yield
In water	98%

2,4,6-Trinitrophenol (88-89-1) + Risperidone (106266-06-2) → C23H27FN4O2*C6H3N3O7 (1425681-44-2)

Conditions	Yield
In methanol at 20℃; for 0.75h; Equilibrium constant;	98%

tetraammine(salicylamidato)cobalt(III) chloride hydrate + 2,4,6-Trinitrophenol (88-89-1) → tetraammine(salicylamidato)cobalt(III) picrate

Conditions	Yield
In water aq. soln. of Co complex added to aq. soln. of picric acid, stirred; ppt. filtered, washed with water and EtOH, dried; elem. anal.;	97.4%

2,4,6-Trinitrophenol (88-89-1) → 2,4,6-triaminophenol (609-24-5)

Conditions	Yield
With sodium tetrahydroborate; pyrographite In tetrahydrofuran; water at 50 - 60℃; for 4h;	97%
With sodium tetrahydroborate; antimony(III) fluoride In water; acetonitrile at 20℃; for 0.5h;	90%
With hydrogenchloride; tin(ll) chloride Electrolysis;

2,4,6-Trinitrophenol (88-89-1) + (3aα,4α,7α,7aα)-3a,4,5,6,7,7a-Hexahydro-4,7-methano-3,3-dimethyl-1-(2,4,6-trichlorophenyl)-3H-indazolium terachloroaluminate → (3aα,4α,7α,7aα)-3a,4,5,6,7,7a-Hexahydro-4,7-methano-3,3-dimethyl-1-(2,4,6-trichlorophenyl)-3H-indazolium picrate

Conditions	Yield
In ethanol	97%

O,O-dimethyl (1-tert-butyl-3,3-dimethyl-aziridin-2-yl)phosphonate + 2,4,6-Trinitrophenol (88-89-1) → 1-tert-butyl-2-dimethoxyphosphoryl-3,3-dimethylaziridinium 2,4,6-trinitrophenoxide (1326345-04-3)

Conditions	Yield
In diethyl ether at 20℃; for 24h; Inert atmosphere;	97%

Upstream product

• 96-77-5 4-hydroxy-benzene-1,3-disulfonic acid 
• 606-35-9 1-methoxy-2,4,6-trinitrobenzene 
• 71-43-2 benzene 
• 67-56-1 methanol 
• 88-88-0 2,4,6-trinitrochlorobenzene 
• 10123-09-8 2,4,6-trinitronitrosobenzene 
• 37590-58-2 S,S'-bis(2,4,6-trinitrophenyl) dithiooxalate 
• 81344-96-9 vaticaffinol 
• 99-35-4 1,3,5-trinitrobenzene 
• 108-95-2 phenol 
• 137-51-9 4-aminobenzene-1,3-disulfonic acid 
• 121-57-3 4-aminobenzene sulfonic acid 
• 482-89-3 1H,1H'-2,2'-Biindolylidene-3,3'-dione 
• 54-12-6 Trp 

Downstream Products

• 121790-99-6 1,1'-(4,7-dioxo-3,8-diaza-decanediyl)-bis-pyridinium; dipicrate 
• 119369-65-2 1,1'-(4,9-dioxo-3,10-diaza-dodecanediyl)-bis-pyridinium; dipicrate 
• 112625-97-5 triethyl-(β-hydroxy-phenethyl)-ammonium; picrate 
• 58077-34-2 N¹-benzyl-N²-phenylethane-1,2-diamine 
• 100-52-7 benzaldehyde 
• 5938-04-5 benzyliden-aniline; picrate of benzylidenaniline 
• 88-88-0 2,4,6-trinitrochlorobenzene 
• 93-98-1 N-phenyl benzoyl amide 
• 14703-71-0 2-hydroxy-6-amino-1-nitrobenzene 
• 609-24-5 2,4,6-triaminophenol 
• 17356-96-6 Anthracene picrate 

Relevant articles and documents

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Medium effect on the reaction of N-butyl-2,4,6-trinitroaniline with NaOH

The kinetics of the reaction of N-butyl-2,4,6-trinitroaniline (3) with NaOH have been studied in 10 and 60% 1,4-dioxane/H2O at 25 °C. In both cases, several processes were observed. In 10% 1,4-dioxane/H2O the only product formed was 2,4,6-trinitrophenol (4), whereas in 60% 1,4-dioxane/ H2O a mixture of 4 and 5,7-dinitro-2-propyl-1H-benzimid- azole 3-oxide (5) was observed in ratios that depend on the HO- concentration. A mechanism involving the formation of a complexes through the addition of one or two HO- anions to unsubstituted ring positions is proposed for 2,4,6-trinitrophenol formation. The presence of these complexes was confirmed by NMR studies in 60% [D8]1,4-dioxane/D2O. The mechanism suggested for the formation of the N-oxide includes the cyclization of an N-alkylidene-2-nitrosoaniline-type intermediate as the rate-determining step. The decrease in solvent polarity produces a decrease in the observed rate constant for the formation of 4 of about one order of magnitude making the cyclization reaction a competitive pathway. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

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Supramolecular structure of 2,4,6-trinitrophenol

The compound 2,4,6-trinitrophenol with the molecular formula C6H3N3O7, crystallizes with two crystallographically independent but chemically identical molecules in the asymmetric unit. The dihedral angle formed by the two benzene rings is about 67.49. The

Visible-Light-Induced Radical Polynitration of Arylboronic Acids: Synthesis of Polynitrophenols

We report a visible light-assisted one-pot method for the synthesis of polynitrophenols through radical tandem hydroxylation and nitration of arylboronic acids by utilizing copper(II) nitrate tri-nitydrate as the nitro source. This method features mild conditions, a simple procedure, and good functional group tolerance. Compared to conventional methods, this work provides a straightforward approach for the polynitration of aromatic compounds.

O-Phenylisourea Synthesis and Deprotonation: Carbodiimide Elimination Precludes the Reported Chapman Rearrangement

The kinetics of the addition of phenol to diisopropylcarbodiimide, and reaction of the resulting N,N′-diisopropyl-O-phenylisourea with hydroxide, are reported. The isourea is generated by a slow overall termolecular equilibrium process, inhibited by isourea–phenol salt generation. In contrast to an earlier report, reaction of the isourea with hydroxide does not induce a synthetically useful 1,3-O–N (Chapman) rearrangement. Instead, deprotonation results in solvolysis by carbodiimide elimination.