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131222-99-6

131222-99-6

Identification

Synonyms:Dibromochrysene;

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Safety information and MSDS view more

  • Signal Word:Warning

  • Hazard Statement:H302 Harmful if swallowedH413 May cause long lasting harmful effects to aquatic life

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

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  • Manufacture/Brand:TRC
  • Product Description:6,12-Dibromochrysene
  • Packaging:5mg
  • Price:$ 60
  • Delivery:In stock
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  • Manufacture/Brand:TCI Chemical
  • Product Description:6,12-Dibromochrysene >98.0%(HPLC)
  • Packaging:200mg
  • Price:$ 138
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  • Manufacture/Brand:TCI Chemical
  • Product Description:6,12-Dibromochrysene >98.0%(HPLC)
  • Packaging:1g
  • Price:$ 412
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:6,12-Dibromochrysene 95+%
  • Packaging:250mg
  • Price:$ 319
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  • Manufacture/Brand:Matrix Scientific
  • Product Description:6,12-Dibromochrysene 95+%
  • Packaging:1g
  • Price:$ 706
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  • Manufacture/Brand:Labseeker
  • Product Description:6,12-DIBROMOCHRYSENE 95
  • Packaging:100g
  • Price:$ 1046
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  • Manufacture/Brand:Crysdot
  • Product Description:6,12-Dibromochrysene 97%
  • Packaging:1g
  • Price:$ 231
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  • Manufacture/Brand:Crysdot
  • Product Description:6,12-Dibromochrysene 97%
  • Packaging:5g
  • Price:$ 704
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:6,12-Dibromochrysene
  • Packaging:2 g
  • Price:$ 570
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  • Manufacture/Brand:Biosynth Carbosynth
  • Product Description:6,12-Dibromochrysene
  • Packaging:500 mg
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Relevant articles and documentsAll total 8 Articles be found

Flash vacuum thermolysis of acenaphtho[1,2-a]acenaphthylene, fluoranthene, benzo[k]- and benzo[j]fluoranthene - Homolytic scission of carbon-carbon single bonds of internally fused cyclopenta moieties at T ≥ 1100°C

Sarobe, Martin,Kwint, Huibert C.,Fleer, Theun,Havenith, Remco W.A.,Jenneskens, Leonardas W.,Vlietstra, Edward J.,Van Lenthe, Joop H.,Wesseling, Jolanda

, p. 1191 - 1200 (1999)

Flash vacuum thermolysis (FVT, 1000 °C ≥ T ≥ 1200 °C) of acenaphtho[1,2-a]acenaphthylene (3, C22H12) gave the C22H12 cyclopenta-fused polycyclic aromatic hydrocarbon (CP-PAH) acenaphtho[1,2- e]acenaphthylene (4), cyclopenta[cd]perylene (5) and cyclopenta[def]benzo[hi]chrysene (6). Whereas the formation of 4 is explained by a ring contraction/ring expansion rearrangement of 3, the identification of 5 and 6 suggests that 3 also undergoes homolytic scission of a five- membered ring's carbon-carbon single bond furnishing the transient diradical intermediate 7. Ring closure of 7 to form 8 after rotation around the carbon- carbon single bond of the intact five-membered ring followed by hydrogen shifts will give 6. The latter can rearrange subsequently into 5 by ring contraction/ring expansion. The structural assignment of 4 and 5 was supported by independent FVT of 6,12-bis(1-chloroethenyl)chrysene (14) and 3- (1-chloroethenyl)perylene (23), respectively. FVT of 14 (900-1200 °C) gave in a consecutive process 6,12-bis(ethynyl)chrysene (15), 9- ethynylbenz[j]acephenanthrylene (16) and bis(cyclopenta[hi,qr])chrysene (17). Although at T ≥ 900 °C 17 selectively rearranges into 4 by ring contraction/ring expansion, at 1200 °C the latter is converted into 5 presumably via a diradical intermediate obtained by homolytic scission of a single carbon-carbon bond of a five-membered ring. FVT of 23 gave in situ 3- ethynylperylene (25), which at 1000 °C is nearly quantitatively converted into 5. The propensity of internal cyclopenta moieties to undergo homolytic scission of a five-membered ring's carbon-carbon single bond was corroborated by independent FVT of benzo[k]- (11) and benzo[j]fluoranthene (12). Previously unknown thermal pathways to important (CP)-PAH combustion effluents are disclosed at T≥ 1000 °C.

From chrysene to double [5] Helicenes

Bock, Harald,Huet, Stephanie,Dechambenoit, Pierre,Hillard, Elizabeth A.,Durola, Fabien

, p. 1033 - 1039 (2015)

Glyoxylic functionalization of chrysene by Friedel-Crafts acylation with ethyl chloroglyoxylate or by bromination followed by substituent exchange enables the formation of bis[5]helicene-tetracarboxylates and tetracarboxdiimides through Perkin reactions and palladium-catalyzed cyclizations. Tetrasubstituted bishelicenic dichrysenoanthracenes and dinaphthochrysenes are thus obtained from chrysene in four to six steps. In the cyclization to dinaphthochrysenes, a rearrangement of the conjugated carbon skeleton is identified as side reaction. In solution, the diimides form mixtures of M,P- and M,M/P,P-diastereomers, which equilibrate at room temperature when the helices are distant but equilibrate only upon heating when the helices are close and acting in concert. The nonplanar arene geometry allows close π-contacts in two dimensions between neighboring molecules in the crystal.

AROMATIC AMINE DERIVATIVE AND ORGANIC ELECTROLUMINESCENT DEVICES CONTAINING THE SAME

-

Paragraph 0112-0113, (2021/03/03)

To further develop a fluorescent light emitting material so as to obtain a higher element efficiency, a longer lifetime of the device, and more blue emission.SOLUTION: The invention discloses aromatic amine derivative, and an organic electroluminescent device including the same. In a structure, fluorene/silafluorene groups with ortho-substituents are introduced into the aromatic amine derivative, therefore the aromatic amine derivative can be used as light-emitting materials in a light-emitting layer of the organic electroluminescent device. These novel compounds can provide better device performance.SELECTED DRAWING: None

Chrysene-Based Azahelicene π-Linker of D-π-D-Type Hole-Transporting Materials for Perovskite Solar Cells

Tang, Zefeng,Li, Tianyu,Cao, Yucai,Zhang, Yuyan,He, Lifei,Zheng, Aibin,Lei, Ming

, p. 4923 - 4928 (2021/10/19)

Chrysene is a readily available material for exploring new polycyclic aromatic hydrocarbons (PAHs). In this study, two chrysene based azahelicenes, nine-membered BA7 and ten-membered DA6, are constructed by intermolecular oxidative annulation of 6-aminochrysene and intramolecular annulation of N6,N12-bis(1-chloronaphthalen-2-yl)chrysene-6,12-diamine, respectively. The hexylated BA7 and DA6 and their brominated products were undoubtedly characterized by single crystal XRD. Subsequent amination with bis(9-methyl-9H-carbazol-3-yl)amine (BMCA) electron donor afforded D-π-D-type semiconductors BA7-BMCA and DA6-BMCA with beneficial properties to act as hole transport materials for perovskite solar cell. Compared with 19.4 % champion power conversion efficiency (PCE) of BA7-BMCA based device, a higher PCE of 20.2 % for DA6-BMCA counterpart may be attributed to its S-shaped double helicene-like linker with extended π-conjugated system.

Regioselective arene homologation through rhenium-catalyzed deoxygenative aromatization of 7-oxabicyclo[2.2.1]hepta-2,5-dienes

Murai, Masahito,Ogita, Takuya,Takai, Kazuhiko

supporting information, p. 2332 - 2335 (2019/02/27)

Combined use of oxorhenium catalysts with triphenyl phosphite as an oxygen acceptor allowed efficient deoxygenative aromatization of oxabicyclic dienes. The reaction proceeded under neutral conditions and was compatible with various functional groups. Combining this deoxygenation with regioselective bromination and trapping of the generated aryne with furan resulted in benzannulative π-extension at the periphery of the PAHs. This enabled direct use of unfunctionalized PAHs for extension of π-conjugation. Iteration of the transformations increased the number of fused-benzene rings one at a time, which has the potential to alter the properties of PAHs by fine-tuning the degree of π-conjugation, shape, and edge topology.

Observation of the rare chrysene excimer

Khorev, Oleg,Boesch, Caroline D.,Probst, Markus,Haener, Robert

, p. 1506 - 1512 (2014/03/21)

Formation of the so far elusive chrysene excimer in solution is achieved by using DNA as a supramolecular scaffold. Oligonucleotides possessing one or two chrysene building blocks have been synthesized. Chrysene excimer fluorescence has been unambiguously observed in DNA double strands, as well as in single strands containing two neighbouring chrysenes.

Process route upstream and downstream products

Process route

chrysene
218-01-9

chrysene

6,12-dibromochrysene
131222-99-6

6,12-dibromochrysene

Conditions
Conditions Yield
With bromine; In chloroform; at 80 ℃; for 24h; regioselective reaction; Inert atmosphere;
90%
With bromine; In 1,2-dichloro-ethane; at 85 ℃; for 18h;
84%
With bromine; In tetrachloromethane; for 4.66h; Reflux;
76.1%
With copper(II) bromide supported on alumina; In tetrachloromethane; for 96h; Heating;
74%
With bromine; In chloroform; for 16h; Reflux;
74%
With bromine; In tetrachloromethane; at 20 ℃; for 5h; Heating / reflux;
73%
With bromine; In 1,2-dichloro-ethane; at 20 - 85 ℃; for 16h; Inert atmosphere;
50%
With bromine; 1,1,2,2-tetrachloroethane;
With bromine; acetic acid;
With carbon disulfide; bromine;
With bromine; nitrobenzene;
With bromine; nitrobenzene;
With bromine; In chloroform; Reflux;
chrysene
218-01-9

chrysene

bromine
7726-95-6

bromine

6,12-dibromochrysene
131222-99-6

6,12-dibromochrysene

Conditions
Conditions Yield
6,12-dibromochrysene
131222-99-6

6,12-dibromochrysene

dibenzo[g,p]chrysene
191-68-4

dibenzo[g,p]chrysene

Conditions
Conditions Yield
Multi-step reaction with 2 steps
1: sodium amide; potassium tert-butylate / tetrahydrofuran / 15 h / 50 °C / Inert atmosphere
2: perrhenic acid anhydride; triphenyl phosphite / toluene / 80 °C / Inert atmosphere
With triphenyl phosphite; perrhenic acid anhydride; potassium tert-butylate; sodium amide; In tetrahydrofuran; toluene; 1: |Diels-Alder Cycloaddition;
9-phenanthrenylboronic acid
68572-87-2

9-phenanthrenylboronic acid

6,12-dibromochrysene
131222-99-6

6,12-dibromochrysene

6,12-bis(9-phenanthryl)chrysene

6,12-bis(9-phenanthryl)chrysene

Conditions
Conditions Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0); In water; toluene; for 10h; Heating / reflux;
93%
6,12-dibromochrysene
131222-99-6

6,12-dibromochrysene

(3,5-dichlorophenyl)boronic acid
67492-50-6

(3,5-dichlorophenyl)boronic acid

6,12-bis-(3,5-dichlorophenyl)chrysene

6,12-bis-(3,5-dichlorophenyl)chrysene

Conditions
Conditions Yield
6,12-dibromochrysene; (3,5-dichlorophenyl)boronic acid; With potassium carbonate; In ethanol; toluene; for 1h; Inert atmosphere; Reflux;
With tetrakis(triphenylphosphine) palladium(0); In ethanol; toluene; at 110 ℃; for 21h; Inert atmosphere;
N-phenyl-(9,9-dimethyl-9H-fluoren-2-yl)amine
355832-04-1

N-phenyl-(9,9-dimethyl-9H-fluoren-2-yl)amine

6,12-dibromochrysene
131222-99-6

6,12-dibromochrysene

C<sub>60</sub>H<sub>46</sub>N<sub>2</sub>

C60H46N2

Conditions
Conditions Yield
With palladium diacetate; sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate; In 5,5-dimethyl-1,3-cyclohexadiene; at 80 ℃; for 0.5h; Inert atmosphere;
70%
N-phenyl-(9,9-dimethyl-9H-fluoren-2-yl)amine
355832-04-1

N-phenyl-(9,9-dimethyl-9H-fluoren-2-yl)amine

6,12-dibromochrysene
131222-99-6

6,12-dibromochrysene

C<sub>60</sub>H<sub>46</sub>N<sub>2</sub>

C60H46N2

Conditions
Conditions Yield
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate; In toluene; for 12h; Inert atmosphere; Reflux;
60.2%
1,2-bis(4-methylphenyl)acetylene
2789-88-0

1,2-bis(4-methylphenyl)acetylene

6,12-dibromochrysene
131222-99-6

6,12-dibromochrysene

4,5-di(4-tolyl)cyclopenta[hi]chrysene

4,5-di(4-tolyl)cyclopenta[hi]chrysene

4,5,10,11-tetra(4-tolyl)dicyclopenta[hi,qr]chrysene

4,5,10,11-tetra(4-tolyl)dicyclopenta[hi,qr]chrysene

Conditions
Conditions Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; cesium pivalate; In 1,4-dioxane; at 130 ℃; for 24h; regioselective reaction; Sealed tube;
10%
50%
6,12-dibromochrysene
131222-99-6

6,12-dibromochrysene

acetic acid
64-19-7,77671-22-8

acetic acid

p-benzoquinone
106-51-4

p-benzoquinone

Conditions
Conditions Yield
di-p-tolylamine
620-93-9

di-p-tolylamine

6,12-dibromochrysene
131222-99-6

6,12-dibromochrysene

tetra-p-tolylchrysene-6,12-diamine

tetra-p-tolylchrysene-6,12-diamine

Conditions
Conditions Yield
With tri-tert-butyl phosphine; sodium t-butanolate; palladium diacetate; In toluene; at 100 ℃;
93%
With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In toluene; at 110 ℃; for 10h; Inert atmosphere;
25%

131222-99-6 Upstream products

131222-99-6 Downstream products

Global suppliers and manufacturers

Global( 79) Suppliers
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  • Amadis Chemical Co., Ltd.
  • Business Type:Lab/Research institutions
  • Contact Tel:86-571-89925085
  • Emails:sales@amadischem.com
  • Main Products:29
  • Country:China (Mainland)
  • Shaanxi BLOOM TECH Co.,Ltd
  • Business Type:Lab/Research institutions
  • Contact Tel:+86-29-86470566
  • Emails:sales@bloomtechz.com
  • Main Products:79
  • Country:China (Mainland)
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