苦味酸

Picric Acid

HCID 6954CAS 88-89-1

基本信息

标准SMILES
O=[N+]([O-])c1cc([N+](=O)[O-])c(O)c([N+](=O)[O-])c1
InChIKey
OXNIZHLAWKMVMX-UHFFFAOYSA-N
分子式
C6H3N3O7
平均分子量
229.1 g/mol
单同位素质量
228.99709944

概述

Picric acid, [dry] appears as yellow crystals. An explosive. Specific gravity 1.767. Melting point 251.2 °F (121.8 °C). Explodes at 572 °F. Toxic by ingestion.

名称与标识

首选名称
Picric Acid
IUPAC
2,4,6-trinitrophenol
中文名
苦味酸
英文名
PICRIC ACID
分子式
C6H3N3O7
分子量
229.1

名称与别名

PICRIC ACID2,4,6-TrinitrophenolTrinitrophenol88-89-1Carbazotic acidPicronitric acidMeliniteAcide picriqueNitroxanthic acidPhenol trinitratePicralPikrinezuur
展开更多名称
苦味S苦味酸必苦酸黄色炸药三硝基困醇三硝基苯酚苦味酸 溶液乙腈中苦味酸苦味酸标准品乙腈中苦味酸溶液picric2,4,6-TrinitrofenolPICRIC ACID SOLUTIONPicric acid moistened with water, >=98%TNP、PA
PikrinsaeureAcido picricoPikrynowy kwasPhenol, 2,4,6-trinitro-Phenoltrinitrate2-Hydroxy-1,3,5-trinitrobenzenePicricum acidumKyselina pikrova

数据库标识

CAS
88-89-1
PubChem CID
6954
DTXSID
DTXSID4025909
ChEMBL
CHEMBL108541
ChEBI
CHEBI:46149
UNII
A49OS0F91S
EC Number
201-865-9
Nikkaji
J3.910A

性质

结构计算性质

XLogP
0.9
极性表面积
158 Ų
氢键供体
1
氢键受体
7
可旋转键
0
重原子
16

实验与物化性质

Chemical Classes · 2 条

Other Uses -> Explosives

Flammable agents - 4th degree

DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesBoiling point
LogP · 3 条

log Kow = 1.44

2.03

1.64

OdorOdorless
TasteIntensely bitter

物理化学性质

熔点
122 · 122-123 °C (dried material, Lit. Merck Index 12th Ed.)(lit.)
沸点
300 ℃ · 300℃
密度
1 g/mL · 1.00 g/mL at 20 °C
蒸气密度
7.9 · 7.9 (vs air)
蒸气压
1 mm · 1 mm Hg ( 195 °C)
折射率
1.763 · 1.7630 (estimate)

化学性质

黄色晶体。味很苦,不易吸湿。 难溶于冷水,较易溶于热水,溶于乙醇、乙醚、苯和氯仿。

安全与法规

GHS分类

GHS Classification · 6 条

Danger

H201: (Deleted) Explosive; mass explosion hazard [Danger Explosives]

P210, P230, P240, P250, P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+P364, P370+P380, P372, P373, P401, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H201 (98.5%): (Deleted) Explosive; mass explosion hazard [Danger Explosives]

P203, P210, P230, P240, P250, P260, P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P318, P319, P321, P330, P333+P317, P337+P317, P361+P364, P362+P364, P370+P380, P372, P373, P391, P401, P403+P233, P405, and P501 (click each P-code to see the statement)

危害信息

Regulatory Information · 4 条

Chemical: Phenol, 2,4,6-trinitro-

Status: Cease Manufacture Update: 03-04-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/23472

Phenol, 2,4,6-trinitro- (wetted with >30% water): HSNO Approval: HSR001448 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - Phenol, 2,4,6-trinitro-: Human health tier I assessment
DOT Label · 3 条

Explosive 1.1D

Flammable Solid

Flammable Solid

Fire Hazards · 6 条

Excerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:

Excerpt from ERG Guide 113 [Flammable Materials (Wet / Desensitized Explosive)]:

Excerpt from ERG Guide 113 [Flammable Materials (Wet / Desensitized Explosive)]:

· Flammable/combustible material.

· Flammable/combustible material.

· Flammable/combustible material.

Fire Potential · 3 条

Flammable solid.

Flammable solid when exposed to heat or flame ... .

It will burn once ignited by a flame and will continue to burn quietly if the quantity is small or the material is thinly spread over a large area. /Trinitrophenol, dry/

Health Hazards · 6 条

Excerpt from NIOSH Pocket Guide for Picric acid:

Excerpt from ERG Guide 113 [Flammable Materials (Wet / Desensitized Explosive)]:

Excerpt from ERG Guide 113 [Flammable Materials (Wet / Desensitized Explosive)]:

· Some are toxic and may be fatal if inhaled, ingested or absorbed through skin. Specifically, Dinitrophenol, wetted (UN1320); Dinitrophenolates, wetted (UN1321), Sodium dinitro-o-cresolate, wetted (UN1348); and Barium azide, wetted (UN1571) are known to be toxic.

· Some are toxic and may be fatal if inhaled, ingested or absorbed through skin. Specifically, Dinitrophenol, wetted (UN1320); Dinitrophenolates, wetted (UN1321), Sodium dinitro-o-cresolate, wetted (UN1348); and Barium azide, wetted (UN1571) are known to be toxic.

· Some are toxic and may be fatal if inhaled, ingested or absorbed through skin. Specifically, Dinitrophenol, wetted (UN1320); Dinitrophenolates, wetted (UN1321), Sodium dinitro-o-cresolate, wetted (UN1348); and Barium azide, wetted (UN1571) are known to be toxic.

安全与防护

Fire Fighting · 4 条

Excerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:

Excerpt from ERG Guide 113 [Flammable Materials (Wet / Desensitized Explosive)]:

Excerpt from ERG Guide 113 [Flammable Materials (Wet / Desensitized Explosive)]:

Use water in large amounts. In case of fire: keep drums, etc., cool by spraying with water.

First Aid Measures · 4 条

Fresh air, rest. Refer for medical attention.

Rinse and then wash skin with water and soap. Seek medical attention if you feel unwell.

Rinse with plenty of water for several minutes (remove contact lenses if easily possible).

Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention .

Accidental Release Measures · 6 条

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

First Aid · 6 条

Excerpt from NIOSH Pocket Guide for Picric acid:

Excerpt from ERG Guide 113 [Flammable Materials (Wet / Desensitized Explosive)]:

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

General First Aid:

General First Aid:

General First Aid:

Safe StorageFireproof. Cool. Substance should be kept wet. Separated from strong oxidants, metals and reducing agents. Store in an area without drain or sewer access.
Firefighting Hazards · 3 条

The primary hazard is from blast effect where the entire load can explode instantaneously and not from flying projectiles and fragments. /Trinitrophenol, dry/

Closed containers may rupture violently when heated.

Explosive decomposition may occur under fire conditions.

毒理信息

Interactions · 1 条

Fifty mg/kg of picric acid injected ip into rats 30 min before morphine, meperidine, methadone, pentazocine, etonitazene, aminopyrine, sodium salicylate and pentobarbital potentiated analgesia and sleeping time induced by these drugs, but had no effect on pentylenetetrazole and amphetamine.

Target OrgansEyes, skin, kidneys, liver, blood
Ecotoxicity Values · 5 条

LC50; Species: Nitocra spinipes (Harpacticoid Copepod) age 2-4 wk, adult; Conditions: saltwater, static, 20 °C; Concentration: 72000 ug/L for 96 hr /formulation/

EC50; Species: Daphnia magna (Water Flea) age 6-24 hr newborn, clone 1; Conditions: freshwater, static, 20 °C, dissolved oxygen >80%; Concentration: 104000 ug/L for 24 hr; Effect: intoxication, immobilization /formulation/

EC50; Species: Daphnia magna (Water Flea) age 6-24 hr newborn, clone 1; Conditions: freshwater, static, 20 °C, dissolved oxygen >80%; Concentration: 55000 ug/L for 48 hr; Effect: intoxication, immobilization /formulation/

LC50; Species: Americamysis bahia (Opossum Shrimp) age 4 days, juvenile; Conditions: saltwater, static, 20 °C, pH > or =7.0-8.0, dissolved oxygen 70-121%; Concentration: 13000 ug/L for 96 hr /> or =99% purity/

For more Ecotoxicity Values (Complete) data for Picric acid (8 total), please visit the HSDB record page.

Environmental Fate · 3 条

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 2250(SRC), determined from a structure estimation method(2), indicates that picric acid is expected to have slight mobility in soil(SRC). The pKa of picric acid is 0.42(3), indicating that this compound will exist entirely in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of the anion from moist soil is not expected because anions do not volatilize(SRC). Picric acid is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 7.5X10-7 mm Hg at 25 °C(5). A 23% of Theoretical BOD using activated sludge in the Japanese MITI test(6) suggests that biodegradation is not an important environmental fate process in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 2250(SRC), determined from a structure estimation method(2), indicates that picric acid is expected to adsorb to suspended solids and sediment(SRC). A pKa of 0.42(3) indicates picric acid will exist entirely in the anion form at pH values of 5 to 9 and, therefore, volatilization from water surfaces is not expected to be an important fate process(SRC). The picric acid concentration in sterile pore water decreased from 2000 umoles/L to <1500 umoles/L at 20 °C after 28 days, suggesting that hydrolysis or other unknown abiotic breakdown processes contribute to picric acid transformation(4). According to a classification scheme(5), BCFs of <2.2 measured in carp (Cyprinus carpio)(6) suggest bioconcentration in aquatic organisms is low. Under simulated solar radiation, the picric acid concentration in seawater decreased from 3510.55 umoles/L to 3206.05 umoles/L after 47 days exposure(4). Mixed cultures of phenol adapted microorganisms exhibited little or no oxygen uptake in the presence of picric acid(7-8), suggesting that picric acid is resistant to degradation under aerobic conditions(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), picric acid, which has a vapor pressure of 7.5X10-7 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase picric acid is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 110 days(SRC), calculated from its rate constant of 1.4X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase picric acid may be removed from the air by wet or dry deposition(SRC). Picric acid contains chromophores that absorb at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Exposure Routes · 2 条

The substance can be absorbed into the body by ingestion.

inhalation, skin absorption, ingestion, skin and/or eye contact

法规信息

RCRA RequirementsD003; A solid waste containing picric acid may become characterized as a hazardous waste when subjected to testing for reactivity as stipulated in 40 CFR 261.23, and if so characterized, must be managed as a hazardous waste.
DHS Chemicals of Interest (COI) · 6 条

Trinitrophenol

A Commercial Grade

5000

A Commercial Grade

400

Explosive chemical that can be released at a facility.

State Drinking Water Guidelines(ME) MAINE 57 ug/L

安全数据

wgk
2
tsca
TSCA listed
毒性
LC50 (48-h) for red killifish 513 mg/L (Yoshioka et al., 1986).
RTECS号
TJ7875000
包装类别
I
危险等级
4.1

毒性防护

急性毒性口服- 大鼠 LD50: 200 毫克/ 公斤; 腹注- 小鼠 LD50: 56.3 毫克/ 公斤

职业标准TLV-TWA 0.1 毫克/ 立方米; STEL 0.3 毫克/ 立方米

包装储运 · 3 条

爆炸物危险特性高热、震动、撞击、摩擦可爆

可燃性危险特性燃烧产生有毒氮氧化物烟雾

储运特性轻装轻放; 库房通风、远离明火、高温、阳光; 与氧化剂、易燃物分开存放

化学与工业

药理信息

Biological Half-Life · 2 条

The bioconcentration and metabolism of picric acid and picramic acid were determined for rainbow trout. ... The half-life (t1/2) elimination for the high and low dose of picric acid was 12.0 and 12.5 d, respectively ... .

/In Fischer-344 rats/ the plasma half-life for picric acid was 13.4 hr with a gut absorption coefficient (ka) of 0.069/hr.

Metabolism/Metabolites · 3 条

Picric acid is metabolized largely to picramic acid.

The bioconcentration and metabolism of picric acid and picramic acid were determined for rainbow trout. The bioconcentration factor (BCF) in the epaxial muscle at 42 d for both of these compounds was less than 1; the skin had a BCF value of 1 and 9, respectively. The half-life (t1/2) elimination for the high and low dose of picric acid was 12.0 and 12.5 d, respectively; and for picramic acid was 9.0 and 9.5 d, respectively. In separate experiments, approximately 34% of the injected [14C]picric acid was metabolized to picramic acid, glucuronide conjugates, and an unidentified group of compounds, and 42% of the [(14)C]picric acid was metabolized to picric acid, glucuronide conjugates, and an unidentified group of compounds. The low bioconcentration in the trout muscle may be due to the trout's ability to excrete the parent compound and metabolites. The higher radioactivity observed on the skin may be due to the water route of exposure and the binding of the parent compounds to protein.

Metabolism of picric acid /in Fischer-344 rats/ was limited to reduction of nitro groups to amines. Metabolites isolated from urine included N-acetylisopicramic acid (14.8%), picramic acid (18.5%), N-acetylpicramic acid (4.7%), and unidentified components (2.4%). Approximately 60% of the parent picric acid was excreted unchanged.

MeSH Pharmacological Classification · 2 条

Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant &amp; Hackh&apos;s Chemical Dictionary, 5th ed, p301, p499)

Chemical agents that uncouple oxidation from phosphorylation in the metabolic cycle so that ATP synthesis does not occur. Included here are those IONOPHORES that disrupt electron transfer by short-circuiting the proton gradient across mitochondrial membranes.

Absorption, Distribution and Excretion · 4 条

Twenty-four hours following oral administration of ((14)C)picric acid (100 mg/kg) /to Fischer-344 rats/, the primary depots of radioactivity (per gram tissue basis) were blood, spleen, kidney, liver, lung, and testes. Respective tissue/blood ratios were 0.37, 0.31, 0.28, 0.26, and 0.22. All other tissue assayed had partition ratios < 0.20, with brain and adipose tissue having the least amount of radioactivity. Tissue/blood ratios were essentially maintained over a 48-hr postadministration period. Binding (in vitro) of ((14)C)picric acid to plasma proteins (whole blood preparations) demonstrated both high- and low-affinity binding sites, with dissociation constants of 3.18 x 10-6 and 2.85 x 10-4 M, respectively.

/Picric acid is/ readily absorbed through skin ... .

... /Picric acid/ may be absorbed from ... mucous membranes of body.

... Trinitrophenol /was found/ in the urine of humans following oral exposure. ... Picric acid is eliminated from humans in both the free form and as picramic acid.

用途与制造

Uses · 6 条

Used as an explosive, dye, fungicide, copper etching agent, and chemical intermediate for metal picrates; it is used in the manufacturing of leather products, batteries, colored glass, textile mordants, rocket fuel, and photographic emulsions; [HSDB]

An OSHA Class A Explosive (1910.109)

Battery Manufacturing [Category: Industry]

Explosives, matches; in leather industry; electric batteries; etching copper; manufacture colored glass; textile mordant. Reagent for preparation of organic derivatives for identification.

Used in synthesis of dyes.

Picric acid was used as solvent for extraction of insulin from human tissue.

U.S. Production · 3 条

(1972) PROBABLY GREATER THAN 4.54X10+5 G

(1975) PROBABLY GREATER THAN 4.54X10+5 G

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#3803]

Methods of Manufacturing · 2 条

Prepared by sulfonating phenol then treating with nitric acid ... ; by treating benzene with nitric acid and mercuric nitrate: Teeters, Mueller, United States of America patent 2455322 (1948 to Allied Chem.); by nitration of 2-tert-butyl-4,6-dinitrophenol ... .

Nitration of phenolsulfonic acid, obtained by heating phenol with concentrated sulfuric acid.

Formulations/Preparations · 2 条

Grades: technical paste; pure paste.

Usually found in solution with 10 - 20% water.

General Manufacturing Information · 2 条

Phenol, 2,4,6-trinitro-: ACTIVE

The explosive power of picric acid is somewhat superior to that of TNT, both as regards to the strength and the velocity of detonation.

应用领域

用途用于制红光硫化黑及酸性染料、照相药品、炸药及农药等,医药上用作外科收敛剂

用途用作分析试剂

相关反应

26 条

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