Product Name

  • Name

    Picramic acid

  • EINECS 202-544-6
  • CAS No. 96-91-3
  • Article Data36
  • CAS DataBase
  • Density 1.749 g/cm 3
  • Solubility water: <0.1 g/100 mL at 20.5 °C
  • Melting Point 169 °C
  • Formula C6H5N3O5
  • Boiling Point 386.3 °C at 760 mmHg
  • Molecular Weight 199.123
  • Flash Point 187.5 °C
  • Transport Information UN 3317
  • Appearance dark red crystals
  • Safety 35-61
  • Risk Codes 1-20/21/22-52/53
  • Molecular Structure Molecular Structure of 96-91-3 (Picramic acid)
  • Hazard Symbols ExplosiveE,HarmfulXn
  • Synonyms 1-Amino-2-hydroxy-3,5-dinitrobenzene;1-Amino-3,5-dinitro-2-hydroxybenzene;1-Hydroxy-2-amino-4,6-dinitrobenzene;2,4-Dinitro-6-aminophenol;2-Amino-4,6-dinitrophenol;4,6-Dinitro-2-aminophenol;6-Amino-2,4-dinitrophenol;C.I. Oxidation Base 21;Fourrine 4R;Fourrine 93;Furro 4R;NSC 36939;NSC 4861;Zoba 4R;
  • PSA 137.89000
  • LogP 2.41840

Synthetic route

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

picramic acid
96-91-3

picramic acid

Conditions
ConditionsYield
With sulfur; sodium hydroxide In methanol; water at 80℃; for 8h; Green chemistry;87%
With ethanol; hydrogen sulfide; ammonia
With sodium hydrogensulfide in der Waerme;
ammonium 2-amino-4,6-dinitrophenolate

ammonium 2-amino-4,6-dinitrophenolate

picramic acid
96-91-3

picramic acid

Conditions
ConditionsYield
With acetic acid In water at 60℃; Inert atmosphere;79%
2-amino-6-nitrophenol
603-87-2

2-amino-6-nitrophenol

picramic acid
96-91-3

picramic acid

Conditions
ConditionsYield
With sulfuric acid; nitric acid at 0 - 5℃;40%
dopamine picrate
75802-61-8

dopamine picrate

picramic acid
96-91-3

picramic acid

Conditions
ConditionsYield
at 250℃; for 5h;8%
benzoic acid-(2-hydroxy-3,5-dinitro-anilide)
13316-89-7

benzoic acid-(2-hydroxy-3,5-dinitro-anilide)

picramic acid
96-91-3

picramic acid

Conditions
ConditionsYield
With hydrogenchloride at 140℃;
With hydrogenchloride at 130℃;
acetic acid-(2-hydroxy-3,5-dinitro-anilide)
5422-72-0

acetic acid-(2-hydroxy-3,5-dinitro-anilide)

furan-2,3,5(4H)-trione pyridine (1:1)

furan-2,3,5(4H)-trione pyridine (1:1)

picramic acid
96-91-3

picramic acid

sodium picrate
3324-58-1

sodium picrate

picramic acid
96-91-3

picramic acid

Conditions
ConditionsYield
With methanol; sodium hydrogensulfide
With water; sodium disulfide
ethanol
64-17-5

ethanol

hydrogen sulfide
7783-06-4

hydrogen sulfide

ammonia
7664-41-7

ammonia

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

picramic acid
96-91-3

picramic acid

ammonium chloride

ammonium chloride

water
7732-18-5

water

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

picramic acid
96-91-3

picramic acid

Conditions
ConditionsYield
und im Wasserstoff-Strom erhitztes Aluminium (in Kaeltemischung);
2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

iron(II) sulfate

iron(II) sulfate

alkali

alkali

picramic acid
96-91-3

picramic acid

water
7732-18-5

water

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

D-(+)-lactose
63-42-3

D-(+)-lactose

alkali

alkali

picramic acid
96-91-3

picramic acid

ammonia
7664-41-7

ammonia

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

CuCl

CuCl

picramic acid
96-91-3

picramic acid

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

hydrosulfite sodium

hydrosulfite sodium

picramic acid
96-91-3

picramic acid

water
7732-18-5

water

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

iron-turnings

iron-turnings

picramic acid
96-91-3

picramic acid

Conditions
ConditionsYield
at 100℃;
water
7732-18-5

water

iron(III) chloride
7705-08-0

iron(III) chloride

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

iron-turnings

iron-turnings

picramic acid
96-91-3

picramic acid

Conditions
ConditionsYield
at 100℃;
water
7732-18-5

water

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

iron-turnings

iron-turnings

NaCl

NaCl

picramic acid
96-91-3

picramic acid

Conditions
ConditionsYield
at 100℃;
methanol
67-56-1

methanol

water
7732-18-5

water

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

Na2S

Na2S

NaHCO3

NaHCO3

picramic acid
96-91-3

picramic acid

Conditions
ConditionsYield
at 60℃;
ethanol
64-17-5

ethanol

water
7732-18-5

water

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

Na2S

Na2S

NaHCO3

NaHCO3

picramic acid
96-91-3

picramic acid

Conditions
ConditionsYield
at 80℃;
ammonia
7664-41-7

ammonia

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

SnCl2

SnCl2

picramic acid
96-91-3

picramic acid

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

sodium ferropyrophosphate

sodium ferropyrophosphate

picramic acid
96-91-3

picramic acid

water
7732-18-5

water

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

sodium hydrogensulfide

sodium hydrogensulfide

picramic acid
96-91-3

picramic acid

ethanol
64-17-5

ethanol

sulfuric acid
7664-93-9

sulfuric acid

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

vanadyl sulfate

vanadyl sulfate

picramic acid
96-91-3

picramic acid

Conditions
ConditionsYield
Electrolysis;
ammonia
7664-41-7

ammonia

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

zinc-dust

zinc-dust

picramic acid
96-91-3

picramic acid

ethanol
64-17-5

ethanol

ammonium chloride

ammonium chloride

2,4,6-Trinitrophenol
88-89-1

2,4,6-Trinitrophenol

cerium-powder

cerium-powder

A

2,4,6-triaminophenol
609-24-5

2,4,6-triaminophenol

B

picramic acid
96-91-3

picramic acid

hydrogenchloride
7647-01-0

hydrogenchloride

benzoic acid-(2-hydroxy-3,5-dinitro-anilide)
13316-89-7

benzoic acid-(2-hydroxy-3,5-dinitro-anilide)

A

benzoic acid
65-85-0

benzoic acid

B

picramic acid
96-91-3

picramic acid

Conditions
ConditionsYield
at 130℃;
3.5-dinitro-2-oxy-phenyl isocyanate

3.5-dinitro-2-oxy-phenyl isocyanate

water
7732-18-5

water

picramic acid
96-91-3

picramic acid

Conditions
ConditionsYield
beim Kochen;
acetic acid-(2-amino-4,6-dinitro-phenyl ester)

acetic acid-(2-amino-4,6-dinitro-phenyl ester)

aqueous NaOH-solution

aqueous NaOH-solution

picramic acid
96-91-3

picramic acid

C24H26N4O5

C24H26N4O5

picramic acid
96-91-3

picramic acid

C23H15N5O7

C23H15N5O7

Conditions
ConditionsYield
Stage #1: picramic acid With hydrogenchloride; acetic acid; sodium nitrite In methanol; water at 0℃; for 2h;
Stage #2: C24H26N4O5 With sodium hydroxide In methanol; 2-ethoxy-ethanol; water at 0℃; for 2h; pH=11;
98.3%
3-Hydroxy-naphthalene-2-carboxylic acid butylamide
3665-54-1

3-Hydroxy-naphthalene-2-carboxylic acid butylamide

picramic acid
96-91-3

picramic acid

C21H19N5O7

C21H19N5O7

Conditions
ConditionsYield
Stage #1: picramic acid With hydrogenchloride; acetic acid; sodium nitrite In methanol; water at 0℃; for 2h;
Stage #2: 3-Hydroxy-naphthalene-2-carboxylic acid butylamide With sodium hydroxide In methanol; 2-ethoxy-ethanol; water at 0℃; for 2h; pH=11;
95.1%
2,2-dimethyl-3-(N-methyl-N-phenylamino)-2H-azirine
75755-40-7

2,2-dimethyl-3-(N-methyl-N-phenylamino)-2H-azirine

picramic acid
96-91-3

picramic acid

2-(1-Amino-1-methylethyl)-5,7-dinitro-1,3-benzoxazole
130138-19-1

2-(1-Amino-1-methylethyl)-5,7-dinitro-1,3-benzoxazole

Conditions
ConditionsYield
In acetonitrile for 24h; Ambient temperature;83%
N-methyl-N-phenyl-1-azaspiro[2.4]hept-1-en-2-amine
116139-91-4

N-methyl-N-phenyl-1-azaspiro[2.4]hept-1-en-2-amine

picramic acid
96-91-3

picramic acid

2-(1-Aminocyclopentyl)-5,7-dinitro-1,3-benzoxazole
130138-32-8

2-(1-Aminocyclopentyl)-5,7-dinitro-1,3-benzoxazole

Conditions
ConditionsYield
In acetonitrile for 24h; 0 deg C to room temp.;81%
3,3-bis(3,4,5-trimethoxyphenyl)acrylaldehyde

3,3-bis(3,4,5-trimethoxyphenyl)acrylaldehyde

picramic acid
96-91-3

picramic acid

2-(2,2-bis(3,4,5-trimethoxyphenyl)vinyl)-5,7-dinitrobenzoxazole

2-(2,2-bis(3,4,5-trimethoxyphenyl)vinyl)-5,7-dinitrobenzoxazole

Conditions
ConditionsYield
Stage #1: 3,3-bis(3,4,5-trimethoxyphenyl)acrylaldehyde; picramic acid In ethanol for 3h; Reflux;
Stage #2: With lead(IV) tetraacetate; acetic acid at 20℃; for 1h;
78%
4-(9H-pyrido[3,4-b]indol-1-yl)thiazole-2-carbaldehyde

4-(9H-pyrido[3,4-b]indol-1-yl)thiazole-2-carbaldehyde

picramic acid
96-91-3

picramic acid

1-(2-(5,7-dinitrobenzo[d]oxazol-2-yl)thiazol-4-yl)−9H-pyrido[3,4-b]indole

1-(2-(5,7-dinitrobenzo[d]oxazol-2-yl)thiazol-4-yl)−9H-pyrido[3,4-b]indole

Conditions
ConditionsYield
With [bis(acetoxy)iodo]benzene In 1,4-dioxane at 20℃; for 0.25h;77%
chloroacetyl chloride
79-04-9

chloroacetyl chloride

picramic acid
96-91-3

picramic acid

6,8-dinitro-(2H)-1,4-benzoxazin-3(4H)-one
96753-74-1

6,8-dinitro-(2H)-1,4-benzoxazin-3(4H)-one

Conditions
ConditionsYield
With sodium hydrogencarbonate In water for 4h; Heating;75%
3-(Dimethylamino)spiro<2H-azirin-2,1'-cyclohexan>
56912-87-9

3-(Dimethylamino)spiro<2H-azirin-2,1'-cyclohexan>

picramic acid
96-91-3

picramic acid

A

2-(1-Aminocyclohexyl)-5,7-dinitro-1,3-benzoxazole
130138-33-9

2-(1-Aminocyclohexyl)-5,7-dinitro-1,3-benzoxazole

B

1',2',3',4'-Tetrahydro-5',7'-dinitrospiro-2'-one
130138-29-3

1',2',3',4'-Tetrahydro-5',7'-dinitrospiro-2'-one

C

2'-(Dimethylamino)-3',4'-dihydro-5',7'-dinitrospiro
130138-31-7

2'-(Dimethylamino)-3',4'-dihydro-5',7'-dinitrospiro

D

1-Amino-N-<2-(dimethylamino)-3,5-dinitrophenyl>cyclohexanecarboxamide
130138-35-1

1-Amino-N-<2-(dimethylamino)-3,5-dinitrophenyl>cyclohexanecarboxamide

Conditions
ConditionsYield
In acetonitrile for 24h; 0 deg C to room temp.;A 54%
B 3%
C 8%
D 27%
picramic acid
96-91-3

picramic acid

A

3'-(Dimethylamino)spiroazirin>
108805-12-5

3'-(Dimethylamino)spiroazirin>

B

2'-(Dimethylamino)-3',4'-dihydro-5',7'-dinitrospiro
130138-30-6

2'-(Dimethylamino)-3',4'-dihydro-5',7'-dinitrospiro

C

1-Amino-N-<2-(dimethylamino)-3,5-dinitrophenyl>cyclopentanecarboxamide
130138-34-0

1-Amino-N-<2-(dimethylamino)-3,5-dinitrophenyl>cyclopentanecarboxamide

D

1',2',3',4'-Tetrahydro-5',7'-dinitrospiro-2'-one
130138-28-2

1',2',3',4'-Tetrahydro-5',7'-dinitrospiro-2'-one

Conditions
ConditionsYield
In acetonitrile for 24h; 0 deg C to room temp.;A 40%
B 32%
C 16%
D 4%
3'-(Dimethylamino)spiroazirin>
108805-12-5

3'-(Dimethylamino)spiroazirin>

picramic acid
96-91-3

picramic acid

A

2'-(Dimethylamino)-3',4'-dihydro-5',7'-dinitrospiro
130138-30-6

2'-(Dimethylamino)-3',4'-dihydro-5',7'-dinitrospiro

B

1-Amino-N-<2-(dimethylamino)-3,5-dinitrophenyl>cyclopentanecarboxamide
130138-34-0

1-Amino-N-<2-(dimethylamino)-3,5-dinitrophenyl>cyclopentanecarboxamide

C

2-(1-Aminocyclopentyl)-5,7-dinitro-1,3-benzoxazole
130138-32-8

2-(1-Aminocyclopentyl)-5,7-dinitro-1,3-benzoxazole

D

1',2',3',4'-Tetrahydro-5',7'-dinitrospiro-2'-one
130138-28-2

1',2',3',4'-Tetrahydro-5',7'-dinitrospiro-2'-one

Conditions
ConditionsYield
In acetonitrile for 24h; 0 deg C to room temp.;A 32%
B 16%
C 40%
D 4%
2-phenylamino-5-hydroxynaphthalene-7-sulphonic acid
119-40-4

2-phenylamino-5-hydroxynaphthalene-7-sulphonic acid

picramic acid
96-91-3

picramic acid

C22H15N5O9S

C22H15N5O9S

Conditions
ConditionsYield
Stage #1: picramic acid With hydrogenchloride; sodium nitrite In water at 0 - 5℃; for 1h;
Stage #2: With aminosulfonic acid In water for 0.05h;
Stage #3: 2-phenylamino-5-hydroxynaphthalene-7-sulphonic acid In water at 10℃; for 2h;
3.4%
pyridine
110-86-1

pyridine

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

picramic acid
96-91-3

picramic acid

1-[2,4-dinitro-6-(toluene-4-sulfonylamino)-phenyl]-pyridinium betaine

1-[2,4-dinitro-6-(toluene-4-sulfonylamino)-phenyl]-pyridinium betaine

phthalic anhydride
85-44-9

phthalic anhydride

picramic acid
96-91-3

picramic acid

N-(2-hydroxy-3,5-dinitro-phenyl)-phthalimide

N-(2-hydroxy-3,5-dinitro-phenyl)-phthalimide

Conditions
ConditionsYield
With acetic acid
O4,O6-((R)-ethylidene)-O2,O3-((1Ξ,3Ξ)-1,3-dimethyl-2-oxa-propanediyl)-D-glucose

O4,O6-((R)-ethylidene)-O2,O3-((1Ξ,3Ξ)-1,3-dimethyl-2-oxa-propanediyl)-D-glucose

picramic acid
96-91-3

picramic acid

O4,O6-((R)-ethylidene)-O2,O3-((1Ξ,3Ξ)-1,3-dimethyl-2-oxa-propanediyl)-D-glucose-(2-hydroxy-3,5-dinitro-phenylimine)

O4,O6-((R)-ethylidene)-O2,O3-((1Ξ,3Ξ)-1,3-dimethyl-2-oxa-propanediyl)-D-glucose-(2-hydroxy-3,5-dinitro-phenylimine)

Conditions
ConditionsYield
With methanol
chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

picramic acid
96-91-3

picramic acid

(2-hydroxy-3,5-dinitro-phenyl)-carbamic acid ethyl ester

(2-hydroxy-3,5-dinitro-phenyl)-carbamic acid ethyl ester

acetic anhydride
108-24-7

acetic anhydride

picramic acid
96-91-3

picramic acid

2-methyl-5,7-dinitro-benzooxazole
98434-14-1

2-methyl-5,7-dinitro-benzooxazole

Conditions
ConditionsYield
With sulfuric acid
acetic anhydride
108-24-7

acetic anhydride

picramic acid
96-91-3

picramic acid

A

acetic acid-(2-amino-4,6-dinitro-phenyl ester)

acetic acid-(2-amino-4,6-dinitro-phenyl ester)

B

acetic acid-(2-hydroxy-3,5-dinitro-anilide)
5422-72-0

acetic acid-(2-hydroxy-3,5-dinitro-anilide)

Conditions
ConditionsYield
With sulfuric acid
acetic anhydride
108-24-7

acetic anhydride

picramic acid
96-91-3

picramic acid

acetic acid-(2-hydroxy-3,5-dinitro-anilide)
5422-72-0

acetic acid-(2-hydroxy-3,5-dinitro-anilide)

acetic anhydride
108-24-7

acetic anhydride

picramic acid
96-91-3

picramic acid

2-acetoxy-1-acetylamino-3,5-dinitro-benzene
99057-38-2

2-acetoxy-1-acetylamino-3,5-dinitro-benzene

Conditions
ConditionsYield
With pyridine
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

picramic acid
96-91-3

picramic acid

2,4-dinitro-6-(4-nitro-benzylidenamino)-phenol

2,4-dinitro-6-(4-nitro-benzylidenamino)-phenol

1-methoxy-2,4,6-trinitrobenzene
606-35-9

1-methoxy-2,4,6-trinitrobenzene

picramic acid
96-91-3

picramic acid

1,3,6,8-tetranitro-phenoxazine

1,3,6,8-tetranitro-phenoxazine

Conditions
ConditionsYield
With ethanol; sodium acetate at 130℃; im Rohr;
benzyl chloride
100-44-7

benzyl chloride

picramic acid
96-91-3

picramic acid

2-benzylamino-4,6-dinitro-phenol

2-benzylamino-4,6-dinitro-phenol

Conditions
ConditionsYield
With water
salicylaldehyde
90-02-8

salicylaldehyde

picramic acid
96-91-3

picramic acid

salicylaldehyde-(3.5-dinitro-2-hydroxy-phenylimine)

salicylaldehyde-(3.5-dinitro-2-hydroxy-phenylimine)

Conditions
ConditionsYield
With potassium hydroxide

Picramic acid Chemical Properties

IUPAC Name: Picramic acid
The MF of Picramic acid (96-91-3) is C6H5N3O5.

                    
The MW of Picramic acid (96-91-3) is 199.12.
Synonyms of Picramic acid (96-91-3): Phenol, 2-amino-4,6-dinitro- ; 1-Amino-2-hydroxy-3,5-dinitrobenzene ; 2,4-Dinitro-6-aminophenol ; 2-Amino-4, 6-dinitrophenol ; 4, 6-Dinitro-2-aminophenol ; 2-Hydroxy-3,5-dinitroaniline
Product Categories: Intermediates of Dyes and Pigments
Form: dark red crystals
Index of Refraction: 1.73  
EINECS: 202-544-6
Density: 1.749 g/ml
Flash Point: 187.5 °C 
Boiling Point: 386.3 °C
Melting Point: 169 °C
Water Solubility: <0.1 g/100 mL at 20.5 ºC
Merck: 7409
Stability: Stable

Picramic acid Uses

   Picramic acid (96-91-3) is used as dye intermediates and indicator.

Picramic acid Toxicity Data With Reference

1.    

mmo-sat 5 µmol/plate

    NEZAAQ    Nippon Eiseigaku Zasshi. Japanese Journal of Hygiene. 38 (1983),533.
2.    

mma-sat 5 µmol/plate

    NEZAAQ    Nippon Eiseigaku Zasshi. Japanese Journal of Hygiene. 38 (1983),533.
3.    

ivn-dog LDLo:150 mg/kg

    AIPTAK    Archives Internationales de Pharmacodynamie et de Therapie. 50 (1935),20.
4.    

ipr-pgn LDLo:140 mg/kg

    AIPTAK    Archives Internationales de Pharmacodynamie et de Therapie. 50 (1935),20.

Picramic acid Safety Profile

Poison by intravenous and intraperitoneal routes. Mutation data reported. Combustible when exposed to heat, flame or oxidizers. A powerful explosive when dry. May explode when shocked or heated. When heated to decomposition it emits toxic fumes of NOx. See also EXPLOSIVES, HIGH.
Safety information of Picramic acid (96-91-3):
Hazard Codes  E,Xn
Risk Statements 
1  Explosive when dry
20/21/22  Harmful by inhalation, in contact with skin and if swallowed
52/53  Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment
Safety Statements 
35  This material and its container must be disposed of in a safe way
61  Avoid release to the environment. Refer to special instructions safety data sheet
RIDADR  3317
RTECS  SJ5800000
HazardClass  4.1
PackingGroup  II

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