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N,N-Diethylanilin

N,N-Diethylaniline

HCID 7061
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Grundinformationen

CAS
91-66-7
Standard-SMILES
CCN(CC)c1ccccc1
InChIKey
GGSUCNLOZRCGPQ-UHFFFAOYSA-N
Summenformel
C10H15N
Durchschnittliche Molmasse
149,23 g/mol
Monoisotopische Masse
149,12044948

Überblick

N,n-diethylaniline appears as a colorless to yellow liquid with a fishlike odor, that is strongly corrosive. Irritating to skin, eyes and mucous membranes and moderately toxic by inhalation, absorption and ingestion. Flash point 185 °F. Used in dyes and in the production of organic chemicals.

Namen und Bezeichner

Bevorzugter Name
N,N-Diethylaniline
IUPAC
N,N-diethylaniline
Lokaler Name
N,N-Diethylanilin
Englischer Name
N,N-Diethylaniline
Summenformel
C10H15N
Molmasse
149.23

Namen und Synonyme

N,N-DIETHYLANILINE91-66-7DiethylanilineDiethylphenylamineN,N-DiethylanilinBenzenamine, N,N-diethyl-PhenyldiethylamineAniline, N,N-diethyl-DiaethylanilinN,N-DiethylbenzenamineN,N-DiethylaminobenzeneN-Phenyldiethylamine
Weitere Namen anzeigen
DEAN,N-DIETHYLANILINE, 98%N,N-DIETHYLANILINE, 98%N,N-DIETHYLANILINE, 98%N, ≥99%(GC)
(diethylamino)benzeneDTXSID80218001WR1HJ2PGWNSC-7205DTXCID701800RefChem:161183N,N-DEA202-088-8

Datenbank-Bezeichner

CAS
91-66-7
PubChem CID
7061
DTXSID
DTXSID8021800
ChEMBL
CHEMBL252071
UNII
1WR1HJ2PGW
EC Number
202-088-8
Nikkaji
J3.559I

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3,3
Polarare Oberfläche (TPSA)
3,2 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
1
Frei drehbare Bindungen
3
Schwere Atome
11
Formalladung
0
Komplexität
91

Experimentelle und physikochemische Eigenschaften

Chemical Classes · 2 Einträge

Nitrogen Compounds -> Amines, Aromatic

Flammable agents - 2nd degree

SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP · 3 Einträge

log Kow= 3.31

3.31

3.11

Density · 4 Einträge

0.906 (USCG, 1999) - Less dense than water; will float

0.9307 @ 20 °C/4 °C

Relative density (water = 1): 0.93

0.9307 @ 20°C

Color/Form · 2 Einträge

Colorless to yellow liquid

BROWN OILY LIQUID

Solubility · 5 Einträge

less than 1 mg/mL at 76.1 °F (NTP, 1992)

1 g dissolves in 70 ml of water at 12 °C; slightly sol in alcohol, chloroform and ether

Sol in acetone

In water, 139 mg/l @ 25 °C

Solubility in water, g/100ml at 25 °C: 0.014

Flash Point · 3 Einträge

185 °F (NTP, 1992)

185 °F (85 °C) (CLOSED CUP)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 6 Einträge

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

P260, P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P319, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 0.2% (1 of 421) of reports.

Danger

H301 (99.8%): Toxic if swallowed [Danger Acute toxicity, oral]

Gefahrenhinweise

Regulatory Information · 6 Einträge

Chemical: Benzenamine, N,N-diethyl-

Hazard Traits - Hepatotoxicity and Digestive System Toxicity; Immunotoxicity; Neurotoxicity

Benzenamine, N,N-diethyl- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenamine, N,N-diethyl- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

REACH registered substance: N,N-diethylaniline (EC: 202-088-8)

Diethylaniline: Does not have an individual approval but may be used under an appropriate group standard

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 LabelPoison
Fire Hazards · 3 Einträge

Special Hazards of Combustion Products: Emits toxic fumes under fire conditions. (USCG, 1999)

· Combustible material: may burn but does not ignite readily.

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 79 °C explosive vapour/air mixtures may be formed.

Health Hazards · 2 Einträge

Chemie und Industrie

Pharmakologische Informationen

Metabolism/MetabolitesIN RAT LIVER MICROSOMES N-DEALKYLATION OCCURRED DURING MICROSOMAL METABOLISM OF N,N-DIALKYLANILINES. N-OXIDATION WAS FOUND WITH N,N-DIETHYLANILINE ONLY.
Absorption, Distribution and Excretion · 2 Einträge

IT IS READILY ABSORBED THROUGH INTACT SKIN ...

... Readily absorbed ... by inhalation of vapors.

Verwendung und Herstellung

Uses · 3 Einträge

Used to make pharmaceuticals and dyes; [HSDB]

USED IN SYNTH OF PHARMACEUTICALS

Chem int for dyes and for other organic syntheses

U.S. Imports · 2 Einträge

(1977) 1.50X10+8 GRAMS (PRINCPL CUSTMS DISTS)

(1979) 2.11X10+8 GRAMS (PRINCPL CUSTMS DISTS)

U.S. Production · 3 Einträge

2023: 220,460 lb

(1977) 9.62X10+8 GRAMS

(1979) 1.16X10+9 GRAMS

Industry UsesIntermediate
Methods of Manufacturing · 2 Einträge

REACTION OF ANILINE WITH ETHANOL AT HIGH PRESSURE WITH AN ACID CATALYST

...by ethylation of aniline: Whitman, US patent 2,501,556 (1950 to Du Pont); Voltz, J Org Chem 22, 48 (1957). Closson et al, J Org Chem 22, 646 (1957); Horyna, Cerny, Coll Czech Chem Commun 21, 906 (1956); from bromobenzene, sodium azide plus diethylamine: Bunnett, Brotherton, J Org Chem 22, 832 (1957).

Formulations/PreparationsGrade: Technical
General Manufacturing Information · 3 Einträge

Miscellaneous Manufacturing

Benzenamine, N,N-diethyl-: ACTIVE

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79 °C c.c.

Boiling Point · 3 Einträge

419.9 °F at 760 mmHg ; 198 °F at 10 mmHg (NTP, 1992)

216.3 °C

216.3 °C @760 [mm Hg]

Decomposition · 2 Einträge

When heated to decomposition it emits toxic fumes of nitroxides.

215 °C

Melting Point · 4 Einträge

-37.8 °F (NTP, 1992)

-38.8 °C

-38 °C

-38.8 °C

Vapor Density · 2 Einträge

1.0 (AIR= 1)

Relative vapor density (air = 1): 5.1

Vapor Pressure · 4 Einträge

1 mmHg at 121.5 °F (NTP, 1992)

0.13 [mmHg]

0.14 mm Hg @ 25 °C

Vapor pressure, Pa at 20 °C: 19

Physikochemische Eigenschaften

Schmelzpunkt
-38 °C · -38 °C
Siedepunkt
217 °C · 217 °C(lit.)
Dichte
0.938 g/mL · 0.938 g/mL at 25 °C(lit.)
Dampfdichte
5.2 · 5.2 (vs air)
Dampfdruck
1 mm · 1 mm Hg ( 49.7 °C)
Brechungsindex
20 · n20/D 1.542(lit.)
Flammpunkt
208 °F · 208 °F
storage temp.
30 °C · Store below +30°C.
Löslichkeit
1 g · water: soluble1g in 70ml at 12°C
pka
6.61 · 6.61(at 22℃)
Aggregatzustand
Liquid
Farbe
Clear yellow
PH
8 · 8 (0.1g/l, H2O, 20℃)
Explosionsgrenze
1.1 · 1.1-5.3%(V)
Wasserlöslichkeit
14 g/L · 14 g/L (12 ºC)
Merck
14 · 14,3114
BRN
742483 · 742483
Henry's Law Constant
6.7 · 6.7×10-2 mol/(m3Pa) at 25℃, Brockbank (2013)
Dielectric constant
5.5 · 5.5(19℃)
Stabilität
Stable. Combustible. Incompatible with strong oxidizing agents, strong acids.
InChI
1S/C10H15N/c1-3-11(4-2)10-8-6-5-7-9-10/h5-9H,3-4H2,1-2H3
InChIKey
GGSUCNLOZRCGPQ-UHFFFAOYSA-N
SMILES
CCN(CC)c1ccccc1
LogP
3.904 at · 3.904 at 25℃
CAS Datenbank
91 · 91-66-7(CAS DataBase Reference)
NIST chemische Informationen
Benzenamine, N,N-diethyl-(91-66-7)
EPA chemische Informationen
N,N-Diethylaniline (91-66-7)

May be fatal if inhaled, swallowed or absorbed through the skin. Vapor or mist is irritant to the eyes, mucous membranes, upper respiratory tract; causes skin irritation. Absorption into the body leads to the formation of methemoglobin which, in sufficient concentration, may cause cyanosis. Onset may be delayed 2-4 hours or longer. Exposure can cause nausea, dizziness, headache, damage to the eyes, and blood effects. (USCG, 1999)

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

Hazards Summary · 1 Eintrag

A skin and eye irritant; May be absorbed through skin; Can induce methemoglobinemia; May cause anemia; [ICSC] A skin, eye, mucous membrane, and upper respiratory tract irritant; Can induce methemoglobinemia; [CAMEO] An irritant; [MSDSonline] See Aniline.

DOT ID and Guide2432 153
Reactive GroupAmines, Aromatic
EC ClassificationSymbol: T, N; R: 23/24/25-33-51/53; S: (1/2)-28-37-45-61
UN ClassificationUN Hazard Class: 6.1; UN Pack Group: III
Reactivity Profile · 1 Eintrag

N,N-DIETHYLANILINE neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Chemical DangersDecomposes on heating. This produces toxic fumes including nitrogen oxides.
Packaging and LabellingDo not transport with food and feedstuffs.

Sicherheit und Schutzausrüstung

Fire Fighting · 2 Einträge

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Use water spray, foam, powder, carbon dioxide.

First Aid Measures · 4 Einträge

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give one or two glasses of water to drink. Give a slurry of activated charcoal in water to drink. Refer for medical attention .

Accidental Release Measures · 2 Einträge

· 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 · 2 Einträge

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:

Safe StorageStore in an area without drain or sewer access. Well closed. Separated from food and feedstuffs.
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).
Fire Fighting ProceduresIf material involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Keep run-off water out of sewers and water sources.
Nonfire Spill ResponseExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Disposal Methods · 1 Eintrag

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Spillage Disposal · 1 Eintrag

Personal protection: complete protective clothing including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

Preventive Measures · 2 Einträge

If material not on fire and not involved in fire: Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard.

Personnel protection: Keep upwind. Avoid breathing vapors. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Avoid bodily contact with the material.

Isolation and Evacuation · 2 Einträge

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Immediate precautionary measure

Toxikologische Informationen

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,500(SRC), determined from a log Kow of 3.31(2) and a regression-derived equation(3), indicates that N,N-diethylaniline is expected to have low mobility in soil(SRC). A pKa value of 6.57(4) suggests that N,N-diethylaniline will exist partially in the protonated form in moist soils and the protonated form of N,N-diethylaniline is expected to bind strongly to soil surfaces(SRC). Volatilization of N,N-diethylaniline from moist soil surfaces is expected to be an important fate process for the neutral species(SRC) given an estimated Henry's Law constant of 1.9X10-4 atm-cu m/mole(SRC), derived from its vapor pressure of 0.14 mm Hg(5) and water solubility of 139 mg/l(6) at 25 °C. N,N-Diethylaniline is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(5). N,N-Diethylaniline achieved 0% of the theoretical BOD in a sewage sludge test during a 5 day incubation period and was considered persistent(7).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1,500(SRC), determined from a log Kow of 3.31(2) and a regression-derived equation(3), indicates that N,N-diethylaniline is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.9X10-4 atm-cu m/mole(SRC), derived from its vapor pressure of 0.14 mm Hg(4) and water solubility of 139 mg/l(5) at 25 °C. Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 5 hours and 6.5 days, respectively(SRC). A pKa of 6.57(6) suggests that N,N-diethylaniline will exist partially in the protonated form in aqueous environments and the protonated form of N,N-diethylaniline is not expected to volatilize from water. According to a classification scheme(7), BCF values of 17-161 measured in carp(8) suggest bioconcentration in aquatic organisms is low to high. N,N-Diethylaniline achieved 0% of the theoretical BOD in a sewage sludge during a 5 day incubation period and was considered persistent(9). Using the Japanese MITI test, N,N-diethylaniline achieved 0% of theoretical BOD in an acclimated study during a 4 week incubation(8).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), N,N-diethylaniline, which has a vapor pressure of 0.14 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase N,N-diethylaniline 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 2 hours(SRC), calculated from its estimated rate constant of 1.6X10-10 cu cm/molecule-sec at 25 °C(3) determined using a structure estimation method(3).

Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect
Exposure RoutesThe substance can be absorbed into the body by inhalation of its vapour, by ingestion and through the skin.
Signs and Symptoms · 4 Einträge

Blue lips, fingernails and skin. Convulsions. Dizziness. Laboured breathing. Vomiting. Symptoms may be delayed.

Redness. MAY BE ABSORBED! Further see Inhalation.

Redness. Pain.

See Inhalation.

Effluent ConcentrationsN,N-Diethylaniline was detected in the effluent of a publicly owned treatment works in NJ at a concn of 3 ppb(1) and at 2 mg/l in the retort water fraction from a shale oil facility(2).
ICSC Environmental Data · 1 Eintrag

The substance is toxic to aquatic organisms. Bioaccumulation of this chemical may occur along the food chain. It is strongly advised not to let the chemical enter into the environment. The substance may cause long-term effects in the aquatic environment.

Soil Adsorption/Mobility · 1 Eintrag

A pKa value of 6.57(1) suggests that N,N-diethylaniline will exist partially in the protonated form in moist soils and the protonated form of N,N-diethylaniline is expected to bind strongly to soil surfaces(SRC). The Koc of N,N-diethylaniline is estimated as 1,500(SRC), using a log Kow of 3.31(2) and a regression-derived equation(3). According to a classification scheme(4), this estimated Koc value suggests that N,N-diethylaniline is expected to have low mobility in soil.

TSCA Test Submissions · 2 Einträge

Developmental toxicity of diethylaniline was evaluated in groups of 24 pregnant CD rats fed dose levels of 0, 50, 250, or 500 mg/kg bw/day, by gavage, on gestation days 6-15, followed by fetal examination on gestation day 20. The treatment killed 0, 0, and 5 rats in the low-, mid-, and high-dose groups, respectively. Symptoms of maternal toxicity that were observed in all dose groups included decreased body weight gain and food consumption, and excessive salivation; rats in the mid- and high- dose groups also had excessive lacrimation and staining of the skin/fur in the ano-genital region. The treatment was fetotoxic (reduced fetal weight gain and retarded sternebral ossification), but not embryotoxic or teratogenic, at the high-dose level. The treatment was not embryotoxic, fetotoxic, or teratogenic at the low- and mid-dose levels.

Developmental toxicity of diethylaniline was evaluated in groups of 5 pregnant Sprague-Dawley CD rats fed dose levels of 0, 100, 250, 500, 750, 1000, 1500, or 2000 mg/kg bw/day, by gavage, on gestation days 6-15, followed by fetal examination on gestation day 20. The treatment killed 0, 0, 0, and 4 rats in the 100, 250, 500, and 750 mg/kg dose groups, respectively. All rats in the 1000, 1500, and 2000 mg/kg dose groups died by gestation day 7, after receiving 1-2 treatments; embryotoxic, fetotoxic, and teratogenic effects could not be evaluated in those groups. Symptoms of maternal toxicity in surviving dams included decreased body weight gain and food consumption (100, 250, 500, and 750 mg/kg), and staining of the fur in the ano-genital region (250, 500, and 750 mg/kg). Gross necropsy revealed discolored lungs in some dams at all dose levels. The treatment was not embryotoxic (rate of uterine implantation was normal) or teratogenic at any dose level, but was fetotoxic (reduced fetal weight gain) at 500 and 750 mg/kg.

Human Toxicity ExcerptsPOISONING MAY ... OCCUR THROUGH INHALATION OF VAPORS. ... HAZARDS MAY BE CONSIDERED AS SIMILAR TO THOSE OF ANILINE.
Artificial Pollution SourcesN,N-Diethylaniline's production and use in the synthesis of dyes(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 1 Eintrag

N,N-Diethylaniline, present at 100 mg/l, reached 0% of its theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/l and the Japanese MITI test(1). N,N-Diethylaniline achieved 0% of the theoretical BOD in a sewage sludge during a 5 day incubation period and was considered persistent(2).

Environmental Bioconcentration · 1 Eintrag

BCF values of 44-161 were measured for carp exposed to 0.2 mg/l of N,N-diethylaniline for 8 weeks and BCF values of 17-125 were measured for carp exposed to 0.02 mg/l(1). According to a classification scheme(2), this BCF data suggests the potential for bioconcentration in aquatic organisms is low to high.

Regulatorische Informationen

CERCLA Reportable Quantities · 1 Eintrag

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1000 lb or 454 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

Sicherheitsdaten

F
8
wgk
2
tsca
TSCA listed
ridadr
UN 2432
hs_code
2921 42 00
RTECS-Nr.
BX3400000
risk_code
23/24/25-33-51/53
Toxizität
LD50 orally in Rabbit: 610 mg/kg LD50 dermal Rat > 5000 mg/kg
hazard_code
T,N
hazard_note
Toxic
safety_code
28-37-45-61-28A
hazard_class
6.1
packing_group
III
Speicherklasse
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Giftige Stoffe Daten
91-66-7(Hazardous Substances Data)
Hazard Classifications
Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralAquatic Chronic 2Skin Irrit. 2STOT RE 2 Oral
Selbstentzündungstemperatur
500 °C

INSECT REPELLING SUBSTANCE, N,N-DIETHYLANILINE WAS WORKED UP WITH POLYETHYLENE GLYCOL, POLYVINYL ALCOHOL, ETHOXYLATED ALCOHOLS, & CELLULOSE DERIVATIVES TO LOTIONS OR OINTMENTS APPLICABLE TO SKIN. THE COMPOSITION IS READILY WASHED OFF AFTER USE.

Anwendungen

VerwendenN,N-Diethylaniline is used in dyestuffs and in the synthesis of other intermediates and pharmaceuticals.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

EthanolAnilin

Nachgelagerte Produkte

4-Amino-2-chloro-6-methyl-5-nitropyrimidine2-Chlorpyrimidin-4,5-diaminN,N-Diethylbenzol-p-diaminmonohydrochloridTrioxysalen4,6-Dichloro-1H-pyrazolo[3,4-d]pyrimidine2,4-dichloropyrimidine-5-carbonitrile2-Methoxy-5-nitropyrimidin-4-amine2,4,6-Trichloropyrimidin-5-amine2,4-Dichloro-5-nitropyrimidineN,N-Diethyl-1,4-benzoldiamin-sulfat (1:1)4,6-Diamino-5-nitropyrimidine8-Hydroxy-7-methoxycoumarin7-Hydroxy-6-methoxycumarin2-Chlor-5-nitropyrimidin-4-aminN-(2-Amino-4,6-dichloro-5-pyrimidinyl)formamide2,4-Dichloro-6-methyl-5-nitropyrimidine4,5-Diamino-6-methylpyrimidine2,4-Dichloro-5-cyanopyrimidine5-Bromo-2-chloro-4-(dimethylamino)pyrimidine2-Bromofuran6-Amino-5-nitropyrimidin-4-ol4,4'-Benzylidenebis[N,N-diethylaniline9-Hydroxy-7H-furo[3,2-g][1]benzopyran-7-on2,4,6-Trichloro-5-nitropyrimidine2-Chloro(bromo)pyrimidine