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5-Amino-2-bromopyridine structure
5-Amino-2-bromopyridine structure

5-Amino-2-bromopyridine

Iupac Name:6-bromopyridin-3-amine
CAS No.: 13534-97-9
Molecular Weight:173.013
Modify Date.: 2022-11-22 21:53
Introduction:

To a solution of 2-bromo-5-nitropyridine (2.03 g, 10 mmol) in ethanol (48 mL), iron powder (2.8 g, 50 mmol), concentrated hydrochloric acid (1.9 mL) and water (9.1 mL) were sequentially added. 1. 1. Preparation of 6-bromopyridine-3-amine To a solution of 2-bromo-5-nitropyridine (64g, 0.317mol)/ethanol (1L) was successively added Fe powder (88g, 1.571mmol), concentrated hydrochloric acid (61mL) and water (287mL). The reaction mixture was reacted under reflux for 5h. The reaction mixture was cooled and filtered. The filtrate was concentrated and adjusted with a sodium bicarbonate solution to pH≈7-8, and re-filtered. The resulting filtrate was extracted with dichlormethane. The organic phase was dried with anhydrous sodium sulfate, and concentrated in a reduced pressure to produce 40.5g of the title compound as a pale-yellow solid in a yield of 74.4percent.2-Bromo-5-nitro-pyridine (202 g, 1.0 mol) was dissolved in methanol (2.0 L), and a saturated aqueous ammonium chloride solution (2.0 L) was added thereto, followed by stirring at 50° C. Then, iron (224 g, 4.0 mol) was slowly added thereto, followed by stirring at 50° C. for 6 hours. The reaction solution was cooled to room temperature and then filtered, followed by washing with ethyl acetate. The filtrate was diluted with water, followed by extraction with ethyl acetate (1.0 L×6). The extraction liquids were combined, washed with a saturated aqueous sodium hydrogen carbonate solution (2.0 L) and saturated aqueous sodium chloride, and dried over anhydrous sodium sulfate. Then, the solvent was removed under reduced pressure, and the obtained residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate=1:1) to obtain the title compound (126 g, 73percent). [1152] 1H NMR (400 MHz, DMSO-d(Step 1) 6-Bromopyridin-3-amine (0221) (0222) 2-Bromo-5-nitro-pyridine (202 g, 1.0 mol) was dissolved in methanol (2.0 L), a saturated aqueous solution of ammonium chloride (2.0 L) was added thereto, the resulting mixture was stirred at 50° C., then iron (224 g, 4.0 mol) was slowly added thereto, and the resulting mixture was stirred at 50° C. for 6 hours. The reaction solution was cooled to room temperature and then filtered and washed with ethyl acetate. The filtrate was diluted with water and then extracted with ethyl acetate (1.0 L×6). The extracts were combined, washed with a saturated aqueous solution of sodium hydrogen carbonate (2.0 L) and a saturated saline solution, dried over anhydrous sodium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (petroleum ether:ethyl acetate=1:1) to obtain the title compound (126 g, 73percent). (0223) 1H NMR (400 MHz, DMSO-d0.282 g of 5percent Pd / C and lOmmol of anhydrous sodium sulfate were added to a 100 mL round bottom flask containing 20 mmol of 5-nitro-2-bromopyridine in 40 ml of tetrahydrofuran, then hydrogen was introduced, heated to 37 ° C and stirred 20 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, suction filtered, steamed and subjected to column chromatography (eluent: dichloromethane / acetone, 10: 1 in volume ratio) and dried in vacuo to give 2.476 g of 5-amino- Bromopyridine in 72percent yield.Iron powder (88g, 1.571mmol), concentrated hydrochloric acid (61mL) and water (287mL) were sequentially added to a solution of 2-bromo-5-nitropyridine (64g, 0.317mol) in ethanol (1L). Iron powder (88 g, 1.571 mmol), concentrated hydrochloric acid (61 mL) and water (287 mL) were sequentially added to a solution of 2-bromo-5-nitropyridine (64 g, 0.317 mol) in ethanol (1 L). 1.1a Synthesis of 5-amino-2-bromopyridine

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1. Names and Identifiers
1.1 Name
5-Amino-2-bromopyridine
1.2 Synonyms

(2-Bromopyridin-5-yl)amine 2-Amino-5-bromopyridine 2-BROMO-5-AMINOPYRIDINE 2-Bromo-5-aminoyridine 2-Bromopyridin-5-amine 2-Pyridinamine, 5-bromo- 3-Amino-6-bromopyridine 3-Pyridinamine, 6-bromo- 5-AMINO-2-BROMOPYRIDINE 5-BROMO-2-AMINOPYRIDINE 5-Bromo-2-pyridinamine 5-bromopyridin-2-amine 6-Bromo-3-aminopyridine 6-Bromo-3-pyridinamine 6-BROMOPYRIDIN-3-AMINE 6-Bromopyridin-3-ylamine 6-Brompyridin-3-amin EINECS 214-019-9 LABOTEST-BB LT00129606 MFCD00006323 Pyridine, 3-amino-6-bromo- Pyridine, 5-amino-2-bromo- TIMTEC-BB SBB003823 TIMTEC-BB SBB005540

1.3 CAS No.
13534-97-9
1.4 CID
642811
1.5 EINECS(EC#)
214-019-9
1.6 Molecular Formula
C5H5BrN2 (isomer)
1.7 Inchi
InChI=1S/C5H5BrN2/c6-5-2-1-4(7)3-8-5/h1-3H,7H2
1.8 InChkey
XTHKRYHULUJQHN-UHFFFAOYSA-N
1.9 Canonical Smiles
C1=CC(=NC=C1N)Br
1.10 Isomers Smiles
C1=CC(=NC=C1N)Br
2. Properties
2.1 Density
1.71
2.1 Melting point
75-79℃
2.1 Boiling point
291.2 °C at 760 mmHg
2.1 Refractive index
1.636
2.1 Flash Point
291.2 °C at 760 mmHg
2.1 Precise Quality
171.96400
2.1 PSA
38.91000
2.1 logP
2.00750
2.1 Appearance
Beige to brown-black Powder
2.2 Storage
Ambient temperatures.
2.3 Chemical Properties
Light yellow needles 5-Amino-2-bromopyridine Preparation Products And Raw materials Raw materials
2.4 Color/Form
Beige to brown-black
2.5 pKa
1.87±0.10(Predicted)
3. Safety and Handling
3.1 Hazard Codes
Xi
3.1 Risk Statements
R36/37/38
3.1 Safety Statements
S26;S37/39
3.1 Packing Group
III
3.1 Hazard Class
IRRITANT
3.1 Hazard Declaration
H315-H319-H335
3.1 RIDADR
UN 2811 6.1/PG 3
3.1 Caution Statement
P261-P305 + P351 + P338
3.1 WGK Germany
3
4. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H315 Causes skin irritation

H319 Causes serious eye irritation

H335 May cause respiratory irritation

Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P261 Avoid breathing dust/fume/gas/mist/vapours/spray.

P271 Use only outdoors or in a well-ventilated area.

Response

P302+P352 IF ON SKIN: Wash with plenty of water/...

P321 Specific treatment (see ... on this label).

P332+P313 If skin irritation occurs: Get medical advice/attention.

P362+P364 Take off contaminated clothing and wash it before reuse.

P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

P337+P313 If eye irritation persists: Get medical advice/attention.

P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.

P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.

Storage

P403+P233 Store in a well-ventilated place. Keep container tightly closed.

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

5. Synthesis Route
13534-97-9Total: 8 Synthesis Route
13534-97-9
13534-97-9 216 Suppliers

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