3,5-Dibromotoluene Chemical Properties

Melting point:

34-38 °C (lit.)

Boiling point:

246 °C (lit.)

Density 

1.8246 (rough estimate)

refractive index 

1.6075 (estimate)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

color 

White to Yellow to Orange

BRN 

1928685

InChI

InChI=1S/C7H6Br2/c1-5-2-6(8)4-7(9)3-5/h2-4H,1H3

InChIKey

DPKKOVGCHDUSAI-UHFFFAOYSA-N

SMILES

C1(Br)=CC(C)=CC(Br)=C1

CAS DataBase Reference

1611-92-3(CAS DataBase Reference)

NIST Chemistry Reference

Benzene, 1,3-dibromo-5-methyl-(1611-92-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29039990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3,5-Dibromotoluene Usage And Synthesis

Chemical Properties

slightly yellow crystalline solid

Uses

3,5-Dibromotoluene was used in the preparation of 3,5-bis(diphenylphosphinothioyl)toluene.

General Description

3,5-Dibromotoluene is a halogenated toluene and its electric moment was evaluated.

Synthesis

The general procedure for the synthesis of 3,5-dibromotoluene from 2,6-dibromo-4-methylaniline was as follows: 1.5 L of water was added to a 5 L reaction flask and cooled to 0-5 °C in an ice bath. Under stirring conditions, 500 g of 2,6-dibromo-4-methylaniline was added in five batches, keeping the temperature between 0-5 °C to form a light yellow suspension. The temperature was controlled not to exceed 5 °C. Sodium nitrite solution (156 g of sodium nitrite dissolved in 500 mL of water) was added slowly, a small amount of reddish brown gas was released during the reaction, and the solid was gradually dissolved. After the addition was completed, stirring was continued at 0-5°C for 30 min, and the reaction solution became a transparent liquid with some foam on the surface and a small amount of black solid attached to the wall of the bottle. Subsequently, hypophosphite solution (prepared by mixing 524 g of sodium hypophosphite monohydrate and 601 g of 30% hydrochloric acid, and filtered to remove undissolved sodium chloride solid after mixing for 1 hr) was added slowly and dropwise at 0-5 °C. After completion of the dropwise addition, the reaction was maintained at 0-5°C with stirring for 5 hours. The ice bath was removed to allow the reaction temperature to rise rapidly to 15-20 °C and stirring was continued for 16 hours. The amount of diazonium salt intermediate remaining in the reaction solution was detected as 0.87% by HPLC. The reaction mixture was filtered under reduced pressure and washed with water to give 570 g of wet product. The wet product was mixed with 800 mL of methanol and heated to 50 °C with stirring until completely dissolved and layered. The heating was stopped and the stirring was cooled to 0-10 °C, and 514 g of wet product was obtained by filtration. The wet product was dried under reduced pressure at 30 °C to give 440 g of the yellow solid product 3,5-dibromotoluene (HPLC purity: 94%, yield: 93%), which could be used directly in the next step of the reaction.The NMR spectrum of 3,5-dibromotoluene is shown in Figure 2.

References

[1] Patent: CN108250046, 2018, A. Location in patent: Paragraph 0053; 0060; 0061; 0062
[2] Journal of Medicinal Chemistry, 2001, vol. 44, # 12, p. 1866 - 1882
[3] Journal of Medicinal Chemistry, 2001, vol. 44, # 12, p. 1866 - 1882
[4] Chemische Berichte, 1880, vol. 13, p. 963
[5] Chemische Berichte, 1881, vol. 14, p. 417

3,5-Dibromotoluene(1611-92-3)Related Product Information

• Xylene
• 2,4-DIBROMOBIPHENYL
• p-Toluenesulfonic acid
• 1,3-Dibromo-5,5-dimethylhydantoin
• ALPHA,ALPHA-DIBROMOTOLUENE,α,α-dibromotoluene,A,A-DIBROMOTOLUENE
• ETHYL EOSIN
• 3,5-Dibromo-4-hydroxybenzoic acid
• Bromocresol green
• 2,3,4,5,6-Pentabromoethylbenzene
• Tetrabromophenol Blue
• 3,5-Dibromosalicylaldehyde
• 3,4,5,6-TETRABROMO-O-CRESOL
• Toluene
• Tetrabromophthalic anhydride
• 3',3'',5',5''-TETRABROMOPHENOLPHTHALEIN
• 3,5-Dibromosalicylic acid
• 2,6-Dibromo-4-methylaniline
• Bromoxynil