5-Chloro-2,3,3-trimethyl-3H-indole Chemical Properties

Boiling point:

271.1±40.0 °C(Predicted)

Density 

1.083 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.594(lit.)

Flash point:

>230 °F

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

solid

pka

4.87±0.40(Predicted)

color 

Red

InChI

InChI=1S/C11H12ClN/c1-7-11(2,3)9-6-8(12)4-5-10(9)13-7/h4-6H,1-3H3

InChIKey

GSKATGIMEUGNJN-UHFFFAOYSA-N

SMILES

N1C2=C(C=C(Cl)C=C2)C(C)(C)C=1C

CAS DataBase Reference

25981-83-3(CAS DataBase Reference)

EPA Substance Registry System

3H-Indole, 5-chloro-2,3,3-trimethyl- (25981-83-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HS Code 

2933998090

MSDS

• Language:English Provider:SigmaAldrich

5-Chloro-2,3,3-trimethyl-3H-indole Usage And Synthesis

Synthesis

GENERAL METHOD: 3-methyl-2-butanone (1.2 eq.) and p-chlorophenylhydrazine hydrochloride (1 g) were sequentially added to a 10 mL microwave reaction tube equipped with a magnetic stirrer. Subsequently, deionized water (3 mL) and sulfuric acid (0.1 equiv) were added to the reaction mixture. The reaction tube was sealed and placed in a microwave reactor and radiated at 100 °C for 10 min until the feedstock was completely converted. Upon completion of the reaction, the aqueous layer was removed and saturated sodium bicarbonate solution (3 mL) was added to the residue to neutralize the reaction solution. The mixture was sonicated for 10 min to completely quench the residual acidity. The organic layer was separated and the resulting oily product was dissolved in a minimum volume of dichloromethane and dried by adding anhydrous sodium sulfate for 30 minutes. After gravity filtration, the filtrate was concentrated to obtain 5-chloro-2,3,3-trimethylindole in quantitative yield.

References

[1] Dyes and Pigments, 2015, vol. 113, p. 27 - 37
[2] Dyes and Pigments, 2015, vol. 113, p. 27 - 37
[3] Journal of Heterocyclic Chemistry, 2002, vol. 39, # 2, p. 263 - 269
[4] Advanced Synthesis and Catalysis, 2015, vol. 357, # 8, p. 1692 - 1696
[5] Patent: WO2004/39894, 2004, A2. Location in patent: Page 37

5-Chloro-2,3,3-trimethyl-3H-indole(25981-83-3)Related Product Information

• Trimethyl borate
• Epichlorohydrin
• FLUOROLUBE GREASE, GR-362
• Triphenylmethyl Chloride
• Chlorotrimethylsilane
• 2-Methylindole
• λ-Cyhalothrin
• Indole
• 4-Chlorobenzotrifluoride
• Chlorotrifluoroethylene
• Trazodone
• Triazolam
• Chloroacetic acid
• Difluorochloromethane
• 1,3,3-Trimethyl-2-methyleneindoline
• 2,3,3-Trimethylindolenine
• SQ-NHS*
• 5-Chloro-2,3,3-trimethyl-3H-indole