[ CAS No. 4378-61-4 ] {[proInfo.proName]}

Name: 4378-61-4|4,10-Dibromonaphtho[7,8,1,2,3-nopqr]tetraphene-6,12-dione|95%
Brand: Ambeed
SKU: A423545
Rating: 91 (22 reviews)

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2D 3D

Structure of 4378-61-4 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 4378-61-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 4378-61-4 ]

SDS Specification

Alternatived Products of [ 4378-61-4 ]

Product Details of [ 4378-61-4 ]

CAS No. :	4378-61-4	MDL No. :	MFCD00059495
Formula :	C₂₂H₈Br₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HTENFZMEHKCNMD-UHFFFAOYSA-N
M.W :	464.11	Pubchem ID :	78084
Synonyms :

Calculated chemistry of [ 4378-61-4 ]

Physicochemical Properties

Num. heavy atoms :	26
Num. arom. heavy atoms :	22
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	114.59
TPSA :	34.14 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.55 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.1
Log Po/w (XLOGP3) :	6.45
Log Po/w (WLOGP) :	5.96
Log Po/w (MLOGP) :	4.81
Log Po/w (SILICOS-IT) :	7.61
Consensus Log Po/w :	5.59

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	0.0
Egan :	1.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-7.41
Solubility :	0.0000182 mg/ml ; 0.0000000392 mol/l
Class :	Poorly soluble
Log S (Ali) :	-6.96
Solubility :	0.0000507 mg/ml ; 0.000000109 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-10.46
Solubility :	0.0000000159 mg/ml ; 0.0 mol/l
Class :	Insoluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	2.42

Safety of [ 4378-61-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 4378-61-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 4378-61-4 ]
Downstream synthetic route of [ 4378-61-4 ]

[ 4378-61-4 ] Synthesis Path-Upstream 1~5

1
[ 641-13-4 ]
[ 4378-61-4 ]

Reference： [1] Chimica e l'Industria (Milan, Italy), 1936, vol. 18, p. 295,296
[2] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 16, p. 1418
[3] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 16, p. 1410
[4] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 16, p. 1421,1422
[5] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 16, p. 1410
[6] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 16, p. 1421,1422
[7] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 16, p. 1417,1418
[8] Patent: DE458598, , ,
[9] Patent: DE458598, , ,

2
[ 102442-61-5 ]
[ 4378-61-4 ]

Reference： [1] Giorn. Chim. ind. appl., vol. 15, p. 335[2] Chem. Zentralbl., 1933, vol. 104, # II, p. 2819
[3] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 16, p. 1422
[4] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 16, p. 1422,1424

3
[ 857779-55-6 ]
[ 4378-61-4 ]

Reference： [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 16, p. 1413
[2] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 16, p. 1413
[3] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 16, p. 1413

4
[ 96962-87-7 ]
[ 4378-61-4 ]

Reference： [1] Patent: US1876973, 1928, ,
[2] Patent: US1876973, 1929, ,

5
[ 7664-93-9 ]
[ 102442-61-5 ]
[ 4378-61-4 ]

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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Yield	Reaction Conditions	Operation in experiment
39%	Stage #1: 2-(2-ethylhexyl)thiophen With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.333333h; Inert atmosphere; Stage #2: 4,10-dibromoanthanthrone In tetrahydrofuran; hexane at 0℃; for 1h; Inert atmosphere; Stage #3: With hydrogenchloride; tin(ll) chloride In tetrahydrofuran; hexane; water at 20℃; for 1h; Inert atmosphere;	4 Synthesis of 4,10-dibromo-6,12-bis(5-isooctyl-2-thienyl)anthracene (AANT): Add 2-octylthiophene (113 mg, 0.58 mmol) and dry tetrahydrofuran (3 mL) to a dry three-necked flask under nitrogen protection and cool to 0°C. A solution of n-butyllithium in n-hexane (2.5M, 0.23mL, 0.58mmol) was slowly added dropwise to the system.After reacting at this temperature for 20 minutes, use a syringe at 0°C to transfer the reaction solution to a nitrogen atmosphere containing compound 1 (100 mg, 0.14 mmol) dissolved in dry tetrahydrofuran. After reacting at this temperature for one hour, 4 mL 10% will be used. A solution of stannous chloride (400 mg, 1.78 mmol) dissolved in hydrochloric acid was added dropwise, and then returned to room temperature, and reacted for another 1 hour.The reaction was quenched with water, and the organic layer was extracted twice with dichloromethane.The organic layer was dried with anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The crude product was purified by silica gel column chromatography (petroleum ether/dichloromethane 2:1 v/v) to obtain compound 5 as a yellow solid (57mg, 39%) .
39%	Stage #1: 2-(2-ethylhexyl)thiophen With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.333333h; Inert atmosphere; Stage #2: 4,10-dibromoanthanthrone In tetrahydrofuran; hexane at 0℃; for 1h; Inert atmosphere; Stage #3: With hydrogenchloride; tin(II) chloride dihdyrate In tetrahydrofuran; hexane; water at 20℃; for 1h; Inert atmosphere;

Yield	Reaction Conditions	Operation in experiment
73%	With Aliquat 336; sodium hydroxide at 60℃; for 3h; Inert atmosphere;	1 Synthesis of 4,10-dibromo-6,12-bis(2-ethylhexaneoxy)anthracene (AAN): Under the protection of nitrogen,Packed in a 250ml single-neck bottleVat Orange 3(500mg, 1.08mmol), sodium hydroxide solution (0.1m, 50mL, 5mmol), Aliquat 336 (530mg, 0.6mL, 1.31mmol), sodium hydroxide (485mg, 2.78mmol), and bromoisooctane (1.5mL , 1.66g, 8.62mmol). The reaction solution was heated to 60°C for 3h until the reaction system became colorless. Pour out the water gently, and then add 30 mL of methanol. The crude product was filtered off with suction, and then washed with methanol. Purified by silica gel column chromatography (dichloromethane/petroleum ether 1:2v/v) to obtain compound 2 as an orange solid (544mg, 73%).
73%	With sodium dithionite; sodium hydroxide In water at 80℃; for 3h; Inert atmosphere;

Yield	Reaction Conditions	Operation in experiment
83%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; water; palladium diacetate; cesium fluoride; cyclo-octa-1,5-diene at 120℃; for 1.5h; Milling;
43%	Stage #1: 4,10-dibromoanthanthrone; 4-(diphenylamino)phenyl boronic acid With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) In water at 20℃; for 0.0833333h; Stage #2: With triethylamine In water at 80℃; for 12h;	2.3.2. Compounds 1-7, 10 General procedure: Aryl bromide (0.5 mmol, 1 eq.), aryl boronic acid (1.5 mmol, 3 eq.) and Pd(dtbpf)Cl 2 (0.01 mmol, 0.02 eq.) were weighed in the test tube and 3 mL of 2 wt% of l - α-lecithin and Tween 80 (2:8) solution in water were added. The mixture was stirred for 5 min at room temperature, then Et 3 N (3 mmol, 6 eq.) was added. After 12 h, the mixture was diluted with 20 mL of MeOH and filtered.

Yield	Reaction Conditions	Operation in experiment
96%	Stage #1: 4,10-dibromoanthanthrone; 3,5-di-tert-butylphenyl boronic acid With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) In water at 20℃; for 0.0833333h; Stage #2: With triethylamine In water at 80℃; for 12h;	2.3.2. Compounds 1-7, 10 General procedure: Aryl bromide (0.5 mmol, 1 eq.), aryl boronic acid (1.5 mmol, 3 eq.) and Pd(dtbpf)Cl 2 (0.01 mmol, 0.02 eq.) were weighed in the test tube and 3 mL of 2 wt% of l - α-lecithin and Tween 80 (2:8) solution in water were added. The mixture was stirred for 5 min at room temperature, then Et 3 N (3 mmol, 6 eq.) was added. After 12 h, the mixture was diluted with 20 mL of MeOH and filtered.
94%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; 18-crown-6 ether; potassium carbonate In ethanol; water; toluene at 105℃; for 3h; Inert atmosphere;
72%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; water; palladium diacetate; cesium fluoride; 1,5-cyclooctadiene at 120℃; for 1.5h; Milling;

[ CAS No. 4378-61-4 ] {[proInfo.proName]}

Quality Control of [ 4378-61-4 ]

Related Doc. of [ 4378-61-4 ]

Product Details of [ 4378-61-4 ]

Calculated chemistry of [ 4378-61-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 4378-61-4 ]

Application In Synthesis of [ 4378-61-4 ]

[ 4378-61-4 ] Synthesis Path-Upstream 1~5

[ 4378-61-4 ] Synthesis Path-Downstream 1~88

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

72 %	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; cesium fluoride; 1,5-cyclooctadiene In water at 250℃; Sealed tube; Milling;	1 [Example 1] 0.15 mmol (1.0 eqiv) of compound A shown in Scheme 1 and 0.36 mmol of compound B (relative to compound A 2.4 eqiv), 0.015 mmol of Pd(OAc) as a metal catalyst (10 mol % with respect to compound A), and 0.0225 mmol of SPhos as a phosphine compound.(15 mol% with respect to compound A), 0.9 mmol of CsF as a base (6.0 eqiv with respect to compound 1), 1.08 mmol of water as a reaction accelerator (7.2 eqiv with respect to compound A), unsaturated 0.2 μL/mg of 1,5-cyclooctadiene was added as a hydrocarbon compound. The lid of the ball mill jar was closed, the ball mill was mounted, and the jar was heated with a heat gun set at 250° C. while being shaken (30 Hz) and stirred for 90 minutes to carry out a cross-coupling reaction.After completion of the reaction, the reaction mixture was extracted with dichloromethane and dried over magnesium sulfate. Then, after removing dichloromethane with an evaporator, the target compound 1 was isolated by purifying the reaction mixture with silica gel column chromatography. Isolated yield was 72%.
82 %	With water; palladium diacetate; cesium fluoride; 1,5-cyclooctadiene In neat (no solvent) at 80℃; Milling;

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 18-crown-6 ether / water; ethanol; toluene / 3 h / 105 °C / Inert atmosphere 2: tetrahydrofuran / 4 h / -78 - -40 °C / Inert atmosphere 3: hydrogenchloride; tin(II) chloride dihdyrate / tetrahydrofuran; hexane / 1 h / 20 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 18-crown-6 ether / water; ethanol; toluene / 3 h / 105 °C / Inert atmosphere 2: tetrahydrofuran / 4 h / -78 - -40 °C / Inert atmosphere 3: hydrogenchloride; tin(II) chloride dihdyrate / tetrahydrofuran; water / 5 h / 20 °C / Inert atmosphere

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed