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2,2',4,4',6,6'-헥사나이트로다이페닐아민

Dipicrylamine

HCID 8576
노트반응
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
부분 구조 검색유사 구조 찾기

기본 정보

CAS
131-73-7
표준 SMILES
O=[N+]([O-])c1cc([N+](=O)[O-])c(Nc2c([N+](=O)[O-])cc([N+](=O)[O-])cc2[N+](=O)[O-])c([N+](=O)[O-])c1
InChIKey
CBCIHIVRDWLAME-UHFFFAOYSA-N
분자식
C12H5N7O12
평균 분자량
439.21 g/mol
단동위원소 질량
438.99961862

개요

Dipicrylamine appears as a yellow solid. Decomposes violently at high temperatures. Insoluble in water and alcohol. Used as a booster explosive. May explode under prolonged exposure to heat or fire. Primary hazard is the blast effect of an instantaneous explosion and not flying projectiles and fragments.

이름 및 식별자

우선 이름
Dipicrylamine
IUPAC
2,4,6-trinitro-N-(2,4,6-trinitrophenyl)aniline
현지명
2,2',4,4',6,6'-헥사나이트로다이페닐아민
영어명
HexanitrodiphenylaMine
분자식
C12H5N7O12
분자량
439.21

이름 및 동의어

DipicrylamineHexylHexanitrodiphenylamineHexil131-73-7Hexyl (reagent)Bis(2,4,6-trinitrophenyl)amineDipikrylaminEsanitrodifenilaminaHexanitrodifenylamineDiphenylamine, hexanitro-Hexamine (potassium reagent)
이름 더 보기
2,2',4,4',6,6'-헥사나이트로다이페닐아민HNDPAURANTIAHNDPHHEXITECI 10360
2,2',4,4',6,6'-HEXANITRODIPHENYLAMINE2,4,6,2',4',6'-HexanitrodiphenylamineBis(2,4,6-trinitro-phenyl)-amin2,4,6-Trinitro-N-(2,4,6-trinitrophenyl)benzenamineC.I. 1036014STR4KG8TBenzenamine, 2,4,6-trinitro-N-(2,4,6-trinitrophenyl)-Diphenylamine, 2,2',4,4',6,6'-hexanitro-

데이터베이스 식별자

CAS
131-73-7
PubChem CID
8576
DTXSID
DTXSID4059621
UNII
14STR4KG8T
EC Number
205-037-8
Nikkaji
J5.566B

물성

구조 계산 물성

XLogP
3
극성 표면적
287 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
13
회전 가능 결합 수
2
무거운 원자 수
31
형식 전하
0
복잡도
662

실험 및 물리화학적 성질

Chemical Classes · 3건

Nitrogen Compounds -> Other Aromatics (Nitrogen)

Other Uses -> Explosives

Flammable agents - 3rd degree

Color/Form · 3건

Pale yellow prisms from acetic acid

Yellow solid

Yellow prisms

Solubility · 4건

Soluble in alkalies, glacial acetic acid; insoluble in acetone, alcohol, ether

Insoluble in benzene, carbon tetrachloride; very soluble in pyridine

Soluble in nitric acid

In water, 60 mg/L at 17 °C

Decomposition · 2건

When heated to decomposition it emits toxic fumes of /nitroxides/. /Nitrates/

Decomposes violently at high temperatures.

Melting Point244 °C (decomposes)
Physical Description · 3건

Dipicrylamine appears as a yellow solid. Decomposes violently at high temperatures. Insoluble in water and alcohol. Used as a booster explosive. May explode under prolonged exposure to heat or fire. Primary hazard is the blast effect of an instantaneous explosion and not flying projectiles and fragments.

Yellow solid; [Merck Index] Yellow crystals; [MSDSonline]

Yellow solid; [CAMEO]

Stability/Shelf Life

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 6건

Danger

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

P210, P230, P240, P250, P260, P262, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P316, P319, P320, P321, P330, P361+P364, P370+P380, P372, P373, P391, P401, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H201 (100%): (Deleted) Explosive; mass explosion hazard [Danger Explosives]

P210, P230, P240, P250, P260, P262, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P316, P319, P320, P321, P330, P361+P364, P370+P380, P372, P373, P391, P401, P403+P233, P405, and P501 (click each P-code to see the statement)

유해성 정보

Regulatory Information · 2건

Chemical: Benzenamine, 2,4,6-trinitro-N-(2,4,6-trinitrophenyl)-

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.)

DOT LabelExplosive 1.1D
Fire HazardsExcerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:
Fire PotentialFlammable by spontaneous chemical reaction; practically all nitrates are powerful oxidizing agents. /Nitrates/
Health HazardsExcerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:
Hazards Summary · 2건

Explosive compound; [Merck Index] Emergency treatment: Methemoglobinemia; [HSDB] Very toxic by inhalation, ingestion, and skin contact; [eChemPortal: ESIS] May cause irritation; May cause methemoglobinemia; [MSDSonline]

An explosive oxidizing agent; [CAMEO]

화학 및 산업

용도 및 제조

Uses · 4건

Used as a booster explosive (bombs, mines, and torpedo warheads) and as a reagent for gravimetric determination of potassium; [HSDB]

Used as a booster explosive; [CAMEO]

Reagent for gravimetric determination of potassium

Booster explosive

U.S. Production · 2건

(1972) NOT PRODUCED COMMERCIALLY IN US

(1975) NOT PRODUCED COMMERCIALLY IN US

Methods of ManufacturingNitration of diphenylamine, also from dinitrochlorobenzene.
General Manufacturing Information · 3건

Benzenamine, 2,4,6-trinitro-N-(2,4,6-trinitrophenyl)-: ACTIVE

A powerful and violent explosive used as a booster explosive; its use is superior to TNT. It is not as good for this purpose as tetryl, but is extremely stable and much safer to handle.

No longer used as an explosive.

응용 분야

용도Reagent for gravimetric determination of potassium.

상·하류 제품 정보

상류 원료

N-(2,4-디니트로페닐)-2,4-디니트로아닐린picrylanilineN-(2,4-디니트로페닐)-2,4,6-트리니트로아닐린2,4,6-트리니트로-N-(4-니트로페닐)아닐린트라이니트로아니솔

관련 반응

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화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
... Extremely stable ...

물리화학적 성질

녹는점
238 ° · about 238° with dec
끓는 점
550.83 °C · 550.83°C (rough estimate)
밀도
1.6613 · 1.6613 (rough estimate)
굴절률
1.64 · 1.6400 (estimate)
산도 계수 (pKa)
1 · pK1:5.42(+1) (25°C)
수용성
60 mg/L · 60mg/L(17℃)
Henry's Law Constant
4.3 · 4.3×1011 mol/(m3Pa) at 25℃, HSDB (2015)
EPA
2 · Benzenamine, 2,4,6-trinitro-N-(2,4,6-trinitrophenyl)- (131-73-7)

화학적 성질

Yellow solid.decomposes violently at higher temperatures. Insoluble in water and alcohol; soluble in alkalies and warm acetic or nitric acid.

Reactive Group
Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic
RCRA Requirements · 1건

D003; A solid waste containing 2,2',4,4',6,6'-hexanitrodiphenylamine 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.

Reactivity AlertsExplosive
Reactivity Profile · 1건

DIPICRYLAMINE is an oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides may begin a vigorous reaction that culminates in a detonation. May explode in the presence of a base such as sodium hydroxide or potassium hydroxide even in the presence of water or organic solvents. The explosive tendencies of aromatic nitro compounds are increased by the presence of multiple nitro groups.

DOT Hazard Classification · 3건

Hexanitrodiphenylamine or Dipicrylamine or Hexyl

UN0079

Div 1.1 Explosives (with a mass explosion hazard) (49 eCFR § 173.50)

Air and Water ReactionsInsoluble in water.

안전 및 보호

Fire FightingExcerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:
First AidExcerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:
Firefighting HazardsThe primary hazard is from blast effect where the entire load can explode instantaneously and not from flying projectiles and fragments.
Fire Fighting Procedures · 3건

If material on fire or involved in fire: Dangerously explosive. Do not fight fires in a cargo of explosives. Evacuate area and let burn.

Wear positive pressure self-contained breathing apparatus when fighting fires involving this material.

Evacuation: If the material is on fire or involved in fire consider evacuation of one (1) mile radius.

Nonfire Spill ResponseExcerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:
Disposal Methods · 1건

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

Preventive Measures · 2건

If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material wet. Wet spilled material before picking it up. Do not attempt to sweep up dry material.

Personnel protection: Avoid breathing dusts, and fumes from burning material ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water.

Isolation and EvacuationExcerpt from ERG Guide 112 [Explosives - Division 1.1, 1.2, 1.3 or 1.5]:
Personal Protective Equipment (PPE) · 2건

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

Wear appropriate chemical protective gloves and goggles.

독성 정보

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.1X10+6(SRC), determined from a structure estimation method(2), indicates that 2,2',4,4',6,6'-hexanitrodiphenylamine is expected to be immobile in soil(SRC). Volatilization of 2,2',4,4',6,6'-hexanitrodiphenylamine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.3X10-17 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 2,2',4,4',6,6'-Hexanitrodiphenylamine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.3X10-14 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). Biodegradation data in soil were not available(SRC, 2010).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.1X10+6(SRC), determined from a structure estimation method(2), indicates that 2,2',4,4',6,6'-hexanitrodiphenylamine is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.3X10-17 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 76(SRC), from an estimated log Kow of 3.4(6) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC), provided the compound is not metabolized by the organism(SRC). Biodegradation data in water were not available(SRC, 2010).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2,2',4,4',6,6'-hexanitrodiphenylamine, which has an estimated vapor pressure of 6.3X10-14 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase 2,2',4,4',6,6'-hexanitrodiphenylamine may be removed from the air by wet or dry deposition(SRC). 2,2',4,4',6,6'-Hexanitrodiphenylamine does not contain chromophores that absorb at wavelengths >290 nm(3) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect
Ecotoxicity Excerpts · 1건

/AQUATIC SPECIES/ Aqueous samples containing various explosives, their reduced metabolites, as well as related compounds were subjected to the luminescent bacterium Vibrio fischeri NRRLB-11177 to determine their ecotoxicological potential. As the most important parameter, the EC50 values of 24 test compounds were calculated. ... HEXYL must be classified in the category "very toxic to aquatic organisms"...

Soil Adsorption/Mobility · 1건

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 2,2',4,4',6,6'-hexanitrodiphenylamine can be estimated to be 1.1X10+6(SRC). According to a classification scheme(2), this estimated Koc value suggests that 2,2',4,4',6,6'-hexanitrodiphenylamine is expected to be immobile in soil.

Artificial Pollution Sources2,2',4,4'6,6'-Hexanitrodiphenylamine's production and former use as a booster explosive(1) may have resulted in its release to the environment through various waste streams(SRC).
Sediment/Soil ConcentrationsSOIL: 2,2',4,4',6,6'-Hexanitrodiphenylamine was not detected in soil samples from the former munitions plant Nieder-Neuendorf (Brandeburg, Germany)(1).
Environmental Bioconcentration · 1건

An estimated BCF of 76 was calculated in fish for 2,2',4,4',6,6'-hexanitrodiphenylamine(SRC), using an estimated log Kow of 3.4(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC), provided the compound is not metabolized by the organism(SRC).

Volatilization from Water/Soil · 1건

The Henry's Law constant for 2,2',4,4',6,6'-hexanitrodiphenylamine is estimated as 2.3X10-17 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2,2',4,4',6,6'-hexanitrodiphenylamine is expected to be essentially nonvolatile from water and moist soil surfaces(2). 2,2',4,4',6,6'-Hexanitrodiphenylamine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 6.3X10-14 mm Hg(SRC), determined from a fragment constant method(3).

Environmental Abiotic Degradation · 1건

2,2',4,4',6,6'-Hexanitrodiphenylamine is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(1). 2,2',4,4',6,6'-Hexanitrodiphenylamine does not contain chromophores that absorb at wavelengths >290 nm(1) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Probable Routes of Human Exposure · 1건

Occupational exposure to 2,2',4,4',6,6'-hexanitrodiphenylamine may occur through dermal contact with this compound at workplaces where 2,2',4,4',6,6'-hexanitrodiphenylamine is produced or used(SRC). Limited monitoring data indicate that the general populated may have been exposed to 2,2',4,4',6,6'-hexanitrodiphenylamine via ingestion of drinking water. Occupational exposure and general population exposure should be low or non-existent since 2,2',4,4',6,6'-hexanitrodiphenylamine is no longer produced or used as an explosive in the US(1).

Environmental Water Concentrations · 1건

GROUNDWATER: Water samples in the surroundings of a former munitions plant at Elsnig, Germany were found to contain 2,2',4,4',6,6'-hexanitrodiphenylamine at a concentration range of 13 to 215 ug/L(1). The compound was detected, not quantified in the upper 4.6-6.9 m, but not the lower 16-18 m levels in the groundwater at this site(2).

Environmental Fate/Exposure Summary · 1건

2,2',4,4',6,6'-Hexanitrodiphenylamine's production and former use as a booster explosive may have resulted in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 6.3X10-14 mm Hg at 25 °C indicates 2,2',4,4',6,6'-hexanitrodiphenylamine will exist solely in the particulate phase in the atmosphere. Particulate-phase 2,2',4,4',6,6'-hexanitrodiphenylamine will be removed from the atmosphere by wet or dry deposition. 2,2',4,4',6,6'-Hexanitrodiphenylamine does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight. If released to soil, 2,2',4,4',6,6'-hexanitrodiphenylamine is expected to have no mobility based upon an estimated Koc of 1.1X10+6. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 2.3X10-17 atm-cu m/mole. Biodegradation data were not available. If released into water, 2,2',4,4',6,6'-hexanitrodiphenylamine is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 76 suggests the potential for bioconcentration in aquatic organisms is moderate. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Occupational exposure to 2,2',4,4',6,6'-hexanitrodiphenylamine may have occurred through dermal contact with this compound at workplaces where 2,2',4,4',6,6'-hexanitrodiphenylamine was produced or used. Limited monitoring data indicate that the general population may have been exposed to 2,2',4,4',6,6'-hexanitrodiphenylamine via ingestion of drinking water. Occupational exposure and general population exposure should be low or non-existent since 2,2',4,4',6,6'-hexanitrodiphenylamine is no longer produced or used in the US. (SRC)

규제 정보

RCRA Requirements · 1건

D003; A solid waste containing 2,2',4,4',6,6'-hexanitrodiphenylamine 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) · 6건

Dipicrylamine [or] Hexyl

A Commercial Grade

5000

A Commercial Grade

400

Explosive chemical that can be released at a facility.

안전 데이터

tsca
TSCA listed
ridadr
UN 0079 (HEXANITRODIPHENYLAMINE (DIPICRYLAMINE; HEXYL))
risk_code
2-26/27/28-33-51/53
hazard_code
E,T+,N
safety_code
35-36-45-61
위험 등급
1.1D
유해 물질 데이터
131-73-7(Hazardous Substances Data)
2-클로로-1,3,5-트라이니트로벤젠
1,1-디페닐우레아
2,4-디니트로디페닐아민
N-Methyldiphenylamine

공급사8 곳

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