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Ethyl 5-bromonicotinate

Ethyl 5-bromonicotinate structure

CAS No:
20986-40-7
Formula:
C8H8BrNO2
Chemical Name:
Ethyl 5-bromonicotinate
Synonyms:
TIMTEC-BB SBB005820;Ethyl 5-bromopyridine-3-carboxylic acid;Ethyl-5-Bromonicotinate98%;5-Bromonicotinicacidethylester~Ethyl5-bromopyridine-3-carboxylate;5-Bromo Nitinic Acid Ethyl Ester;5-Bromonicotinic acid ethyl ester 97%;Ethyl 5-bromonicotinate 97%;5-BROMONICOTIC ACID ETHYL ESTER
Categories:
Organic Chemistry > Carboxylic Acids and Derivatives

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Description

white crystal powder

Ethyl 5-bromonicotinate Basic Attributes

Molecular Weight：

230.06

Exact Mass：

228.973831

BRN：

131473

EC Number：

-0

NSC Number：

363896

DSSTox ID：

DTXSID10175197

HScode：

2933399090

Characteristics

PSA：

39.2

XLogP3：

Appearance：

white crystal powder

Density：

1.5±0.1 g/cm3

Melting Point：

39-42 °C

Boiling Point：

86-92°C0,5mm

Flash Point：

86-92°C/0.5mm

Refractive Index：

1.545

Storage Conditions：

0-10°C

Vapor Pressure：

0.0135mmHg at 25°C

Safety Information

Hazard category：

IRRITANT

hazard class code：

36/37/38

safety instructions：

37/39-26-3637/39

Marks：

Hazard note：

Irritant

Precautionary statement(s)：

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

Hazard Statements：

H315

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 45 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Ethyl 5-bromonicotinate Use and Manufacturing

5-Bromonicotinic acid (2.66 g, 13.1 rnmol) in excess thionyl chloride (6 mL, 82.3 mmol) was brought to reflux conditions and left to stir overnight. The reaction mixture was cooled to room temperature, placed in an ice bath, and excess ethanol (7 tnL) was added to the mixture portion-wise, with stirring. The reaction mixture was returned to reflux conditions and stirred for 2 h. The solution was then cooled to room temperature and solvent removed en vacuo and redissolved in dichloromethane to produce a suspension. 10' NaHCO3 was added with stirring to obtain a pH = 8. The dichloromethane layer was removed and the aqueous layer was extracted 2 more times with dichloromethane. The organic fractions were combined, back extracted with water, extracted with brine, and dried over Na2SO4. After filtration, the solvent was removed in vacuo and used without further purification (2.99 g, 99percent yield) . 1H NMR (300 MHz, CDC13) ' ppm 9.04 {d, IH), 8.75 (d, IH), 8.34 (dd, IH), 4.35 {d, 3H) , 1.34 Ct, 2H) .To an ice-cool solution of 5-bromonicotinic acid (iS g, 75 mmol) in ethanol (2S0 mL) was added concentrated sulthric acid (4 mL) slowly drop wise and refluxed under argon for 18 h. Ethanol was removed under reduced pressure and resulting white residue was dissolved in water. The aqueous solution was made basic to pH 8 with sat. sodium bicarbonate and extracted with ethet The organic layer was washed with brine, dried over anhydrous MgSO4, and concentrated under diminished pressure afforded 1 as a pale yellow solid: yield1S.20 g (89percent); ‘H NMR (400 MHz, CDC13) ö 1.39 (t, 3H, J=7.2 Hz), 4.40 (q, 2H, J=7.6, 14.8 Hz), 8.40 (t, 1H, J=2.0 Hz), 8.81 (d, 1H, J=2.4 Hz) and 9.10 (d, 1H, J=1.6 Hz); ‘3C NMR (100 MHz, CDC13) ö 14.3, 62.0, 120.7, 127.6, 139.S, 149.0, 1S4.S and 164.1.2-Amino-4-(5-cyano-pyridin-3-yl)-3-cyano-7-methyl-4H-pyrrolo[2, 3-h]chromene; a) Ethyl 5-bromonicotinate:; To a white stirring suspension of 5-bromonicotinic acid (3.00 g, 14.9 mmol) in ethyl alcohol (30.0 mL) was added concentrated H20 ml (27 mmol) of thionyl chloride are added dropwise, at room temperature, to a solution of 10 g (49 mmol) of 5-bromonicotinic acid in 250 ml of ethanol. The reaction medium is stirred at room temperature for 4 days and then evaporated under vacuum. The residue is taken up in dichloromethane and washed with aqueous sodium carbonate solution. The organic phase is dried over sodium sulfate, filtered and evaporated under vacuum. The residue obtained is purified by chromatography on a column of silica eluted with a 7/3 heptane/ethyl acetate mixture. 9 g (82percent) of ethyl 5-bromonicotinate are obtained.

Computed Properties

Molecular Weight:230.06
XLogP3:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:228.97384
Monoisotopic Mass:228.97384
Topological Polar Surface Area:39.2
Heavy Atom Count:12
Complexity:163
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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