3D Mol Similar

9-Bromoanthracene

: Iupac Name：9-bromoanthracene; CAS No.: 1564-64-3; Molecular Weight：257.12526; Modify Date.: 2022-11-29 08:50; Introduction: 9-bromoanthracene is a kind of bromine-derived anthracene. It is known to be able to reversibly photodimerize in a head-to tail fashion upon irradiation by long-wavelength ultraviolet light. The photodimers of 9-bromoanthracene are suitable to be used as alkyl halide initiators in the atom transfer radical polymerization (ATRP) reactions. It is also used as the intermediate for the preparation of the 9-substitued form of the polycyclic aromatic hydrocarbon (PAH) anthracene. View more+

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1. Names and Identifiers

: 1.1 Name; 9-Bromoanthracene; 1.2 Synonyms; 50KG/100KG(CIF INDIA COURIER/AIR) 9-Anthracenyl bromide 9-Anthracyl bromide 9-bromanthracen 9-monobromoanthracene anthracen-9-ylbromide Anthracene, 9-bromo- Anthracene,9-bromo EINECS 216-359-3 MFCD00001243 MS-BROMOANTHRACENE RARECHEM AQ BD AN02 TIMTEC-BB SBB007978; View all

1.3 CAS No.: 1564-64-3

1.4 CID: 74062

1.5 EINECS(EC#): 216-359-3

1.6 Molecular Formula: C14H9Br (isomer)

1.7 Inchi: InChI=1S/C14H9Br/c15-14-12-7-3-1-5-10(12)9-11-6-2-4-8-13(11)14/h1-9H

1.8 InChIkey: ZIRVQSRSPDUEOJ-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=CC=C2C(=C1)C=C3C=CC=CC3=C2Br

1.10 Isomers Smiles: C1=CC=C2C(=C1)C=C3C=CC=CC3=C2Br

2. Properties

2.1 Density: 1.479

2.1 Melting point: 98-100℃

2.1 Boiling point: 389.7 oC at 760 mmHg

2.1 Refractive index: 1.733

2.1 Flash Point: 190.3 oC

2.1 Precise Quality: 255.98900

2.1 PSA: 0.00000

2.1 logP: 4.75550

2.1 Appearance: Yellow Powder

2.2 Storage: Ambient temperatures.

2.3 Chemical Properties: white to light yellow crystal powder

2.4 Color/Form: Yellow

2.5 Water Solubility: Insoluble in water.

2.6 StorageTemp: Sealed in dry,Room Temperature

3. Use and Manufacturing

3.1 Purification Methods: Crystallise 9-bromoanthracene from MeOH or EtOH followed by sublimation in vacuo. [Masnori et al. J Am Chem Soc 108 126 1986, Beilstein 5 IV 2295.]

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Risk Statements: S22-S24/25

4.1 Safety Statements: S24/25

4.1 Hazard Declaration: H315

4.1 RIDADR: NONH for all modes of transport

4.1 Caution Statement: P201, P202, P261, P264, P271, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

4.1 WGK Germany: 3

4.1 Safety: Hazard Codes: Xi
Safety Statements: 22-24/25
S22:Do not breathe dust.
S24/25:Avoid contact with skin and eyes.
WGK Germany: 3
Hazard Note: Irritant
May cause eye irritation. if absorbed through the skin，it will cause skin irritation.
Ingestion:if swallowed，it May cause the irritation of digestive tract.if inhaled.it May be harmful for your respiratory.

4.2 Specification: 9-Bromoanthracene (CAS NO.1564-64-3) is also named as NSC 803 ; Anthracene, 9-bromo- ; 10-Bromoanthracene ; 9-Anthracenyl bromide ; 9-Bromo anthracene . 9-Bromoanthracene (CAS NO.1564-64-3) is white to light yellow crystal powder.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

6. NMR Spectrum

1H NMR : 400 MHz in DMSO-d6

1H NMR : 90 MHz in CDCl3

1H NMR : Predict

Predict 1H proton NMR

IR : KBr disc

IR : nujol mull

Mass

Mass spectrum (electron ionization)

7. Synthesis Route

1564-64-3Total: 19 Synthesis Route

120-12-7 92 Suppliers

1564-64-3 189 Suppliers

Literatures:
Ghorbani-Vaghei, Ramin; Jalili, Hamid Synthesis, 2005 , # 7 art. no. Z21504SS, p. 1099 - 1102
Yield: ~10%

523-27-3 162 Suppliers

1564-64-3 189 Suppliers

Literatures:
Chem. News J. Ind. Sci., , vol. 34, p. 465,145
Yield: null

120-12-7 92 Suppliers

1564-64-3 189 Suppliers

84-65-1 274 Suppliers

Literatures:
Tetrahedron Letters, , vol. 51, # 33 p. 4415 - 4418
Yield: ~85%

View all

8. Precursor and Product

precursor:

109-89-7

120-12-7

100-67-4

20244-61-5

22362-86-3

523-27-3

75-77-4

46491-50-3

7783-06-4

128-08-5

77-48-5

64-19-7

613-31-0

View all

product :

1055-23-8

22362-86-3

27069-99-4

523-27-3

84030-79-5

38474-09-8

141982-29-8

100622-34-2

53531-34-3

82131-18-8

23674-20-6

6313-44-6

61832-79-9

2606-52-2

723-62-6

1210-12-4

87842-41-9

15364-55-3

38982-12-6

602-55-1

87919-72-0

23674-13-7

529-85-1

15080-14-5

13752-40-4

View all

9. Other Information

9.0 Usage: 9-Bromoanthracene acts as an intermediate in the preparation of 9-substituted derivative of the polycyclic aromatic hydrocarbon (PAH) anthracene.

9.1 Preparation: Anthracene (5 g, 28.05 mmol) was dissolved in CHCl3. Then N-bromosuccinimide (NBS，4.99 g, 28.05 mmol) was added in batches away from light, and the reaction solution was continuously stirred for 12 h. The resulting mixture was stirred for another 30 min with appropriate water, and extracted with CH2Cl2. The CH2Cl2 solution was dried over anhydrous MgSO4. After removing CH2Cl2 solvent, the residue was recrystallized from anhydrous ethanol to give 4.78 g (66.3 %) of a green-yellow needle solid. 1H NMR (500 MHz, CDCl3) δ 8.55 (d, J = 8.9 Hz, 2H), 8.48 (s, 1H), 8.03 (d, J = 8.4 Hz, 2H), 7.67 – 7.60 (m, 2H), 7.56 – 7.51 (m, 2H). EI-MS (m/z): Calculated for C14H9Br: 257.13. Found [M+ ]: 255.96.

Synthesis of 9-bromoanthracene

9.2 Synthesis Reference(s): The Journal of Organic Chemistry, 57, p. 2740, 1992 DOI: 10.1021/jo00035a038

9.3 BRN: 1869747

9.4 Description: 9-bromoanthracene is a kind of bromine-derived anthracene. It is known to be able to reversibly photodimerize in a head-to tail fashion upon irradiation by long-wavelength ultraviolet light. The photodimers of 9-bromoanthracene are suitable to be used as alkyl halide initiators in the atom transfer radical polymerization (ATRP) reactions. It is also used as the intermediate for the preparation of the 9-substitued form of the polycyclic aromatic hydrocarbon (PAH) anthracene.

9.5 Chemical Properties: white to light yellow crystal powder

9.6 Purification Methods: Crystallise 9-bromoanthracene from MeOH or EtOH followed by sublimation in vacuo. [Masnori et al. J Am Chem Soc 108 126 1986, Beilstein 5 IV 2295.]

10. Computational chemical data

Molecular Weight: 257.12526g/mol
Molecular Formula: C₁₄H₉Br
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 255.98876
Monoisotopic Mass: 255.98876
Complexity: 203
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 0
Topological Polar Surface Area: 0
Heavy Atom Count: 15
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBwAAAAEAAAAAAAAAAAAAAAAAAAAAAwYMAAAAAAAADBVAAAGABAAAABrACAGAAwAMAAAACAAiBCAAACAAAgAAQIiAAAAKgIICKAERCAIAAggAAIihcAgMAOwAACEAAQgACAAAQgACEAAAAAAAAAAA==

11. Question & Answer

What is 9-Bromoanthracene and how is it synthesized? Dec 06 2022
9-Bromoanthracene, also known as 9-Bromoanthracene, is a yellow solid at room temperature and pressure. It belongs to the class of polycyclic compounds and contains a large conjugated system in its m..
How to Prepare 9-Bromoanthracene: A Professional and Interesting Approach Dec 15 2020
Background and Overview[1] 9-Bromoanthracene is a highly efficient fluorescent and phosphorescent material widely used in the fields of optics, cosmetics, electronics, semiconductors, and electrolumin..

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