8-Bromo-1-naphthoic acid Chemical Properties

Melting point:

162-164

Boiling point:

421.2±18.0 °C(Predicted)

Density 

1.648±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

2.02±0.10(Predicted)

Appearance

Off-white to yellow Solid

InChI

InChI=1S/C11H7BrO2/c12-9-6-2-4-7-3-1-5-8(10(7)9)11(13)14/h1-6H,(H,13,14)

InChIKey

DMEZDDHJCUHENA-UHFFFAOYSA-N

SMILES

C1(C(O)=O)=C2C(C=CC=C2Br)=CC=C1

CAS DataBase Reference

1729-99-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-24/25

Hazard Note 

Irritant

HS Code 

2916399090

8-Bromo-1-naphthoic acid Usage And Synthesis

Synthesis

Under stirring conditions, 1.0 g (2.70 mmol) of dehydrated-8-hydroxymercuric-1-naphthalenecarboxylic acid 26 was added to a mixture of 1.0 mL (67 mmol) acetic acid and 0.40 mL (22.2 mmol) H2O, and the suspension was stirred for 10 min at 0 °C. Subsequently, 0.89 g (8.66 mmol) of NaBr dissolved in 3.2 mL of water and 0.43 g (2.70 mmol) of bromine were added sequentially and the reaction system was slowly heated to 100 °C. After completion of the reaction, it was cooled to room temperature and the mixture was poured into ice and filtered to give 0.57 g (84% yield) of 8-bromo-1-naphthalenecarboxylic acid as a cream-colored solid with a melting point of 173-174 °C (literature value: 174-175 °C). The product was characterized by 1H NMR (500 MHz, DMSO-d6) and 13C NMR (125.77 MHz, DMSO-d6) with the following data: 1H NMR δ 7.49 (t, J = 7.8 Hz, 1H), 7.61 (t, J = 7.3 Hz, 1H), 7.68 (d, J = 7.0 Hz, 1H), 7.96 (d, J = 7.3 Hz, 1H), 8.07 (d, J=8.0 Hz, 1H), 8.11 (d, J=8.0 Hz, 1H), 13.32 (s, 1H); 13C NMR δ119.3,126.3,127.6,128.0,128.3,129.4,131.2,133.6,133.9,135.7, 171.3.

References

[1] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 6, p. 2067 - 2081
[2] Journal of Organic Chemistry, 1983, vol. 48, # 17, p. 2926 - 2928

8-Bromo-1-naphthoic acid(1729-99-3)Related Product Information

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• 1-Naphthoic acid
• 4-Bromomethylbenzoic acid
• Phthalic acid
• Calcium formate
• Retinoic acid
• Benzoic acid
• Benzyl benzoate
• Methyl formate
• Folic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• Citric acid
• Ascoric Acid
• 1-Naphthalenemethanol
• Methyl 4-bromo-1-naphthoate
• 6-BROMO-2-NAPHTHOIC ACID METHYL ESTER,2-Bromo-6-naphthoic acid methylester
• t-Butyl 4-bromo-1-naphthalenecarboxylate
• 5-Bromo-1-naphthoic acid