ChemicalBook--->CAS DataBase List--->1093879-46-9

1093879-46-9

1093879-46-9 Structure

1093879-46-9 Structure
IdentificationBack Directory
[Name]

2-(6-bromopyridin-2-yl)acetic acid
[CAS]

1093879-46-9
[Synonyms]

6-BroMo-2-pyridineacetic acid
2-Pyridineacetic acid, 6-bromo-
2-(6-bromopyridin-2-yl)acetic acid
[Molecular Formula]

C7H6BrNO2
[MDL Number]

MFCD10000075
[MOL File]

1093879-46-9.mol
[Molecular Weight]

216.03
Chemical PropertiesBack Directory
[Boiling point ]

347.2±27.0 °C(Predicted)
[density ]

1.710±0.06 g/cm3(Predicted)
[storage temp. ]

Inert atmosphere,2-8°C
[pka]

3.76±0.10(Predicted)
[Appearance]

Off-white to light brown Solid
[InChI]

InChI=1S/C7H6BrNO2/c8-6-3-1-2-5(9-6)4-7(10)11/h1-3H,4H2,(H,10,11)
[InChIKey]

XZQWPHKCEJPCDK-UHFFFAOYSA-N
[SMILES]

C1(CC(O)=O)=NC(Br)=CC=C1
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H335
[Precautionary statements ]

P264-P280-P302+P352-P321-P332+P313-P362-P305+P351+P338-P337+P313-P261-P271-P304+P340-P312-P403+P233-P405-P501
[HazardClass ]

IRRITANT
[HS Code ]

2933399990
Hazard InformationBack Directory
[Uses]

6-Bromo-2-pyridineacetic Acid is used in preparation of pyrimidine derivatives as RORγ modulators.
[Synthesis]

(6-BroMopyridin-2-yl)acetic acid ethyl ester

955369-63-8

2-(6-bromopyridin-2-yl)acetic acid

1093879-46-9

The general procedure for the synthesis of 2-bromo-6-pyridylacetic acid from ethyl (6-bromopyridin-2-yl)acetate was as follows: to a mixed solution of THF (10 mL), water (10 mL), and MeOH (20 mL) containing ethyl 2-(6-bromo-2-pyridinyl)acetate (2.00 g, 8.19 mmol) was added LiOH-H2O (1.03 g, 24.5 mmol). Subsequently, the reaction mixture was stirred at 20 °C for 2 hours. After completion of the reaction, the mixture was concentrated in vacuum. The residue was acidified with 1.0 N HCl to pH=3.0, washed with water (150 mL) and extracted with ethyl acetate (3 x 150 mL). The organic layers were combined, dried with Na2SO4, filtered and concentrated in vacuum to give 2-bromo-6-pyridineacetic acid (1.70 g, 96% yield) as a light yellow solid. The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ=12.63 (br.s, 1H), 7.86-7.71 (m, 1H), 7.59 (d, J=8.0 Hz, 1H), 7.46 (d, J=7.6 Hz, 1H), 3.81 (s, 2H).

[References]

[1] Patent: WO2018/106636, 2018, A1. Location in patent: Paragraph 00239
[2] Journal of Organic Chemistry, 2018, vol. 83, # 16, p. 9088 - 9095
Spectrum DetailBack Directory
[Spectrum Detail]

2-(6-bromopyridin-2-yl)acetic acid(1093879-46-9)1HNMR
2-(6-bromopyridin-2-yl)acetic acid(1093879-46-9)FT-IR
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