2-Bromopyridine

Iupac Name：2-bromopyridine

Molecular Weight：157.998

Modify Date.: 2022-11-29 12:05

Introduction: 2-Bromopyridine is a 2-halogenated pyridine used in the preparation of a variety of biologically active compounds such as antimalarial agents and beta-adrenoceptor agonist. View more+

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1. Names and Identifiers

1.1 Name: 2-Bromopyridine
1.2 Synonyms: 2,6-DI-TERT-BUTYL-4-MERCAPTOPHENOL 2-BROMO PYRIDINE 2-BROMO-6-METHYLPYRIDINE 2-Bromopyridin 2-Bromo-pyridine 2-BROMOPYRIDINE FOR SYNTHESIS 2-brompyridin 2-Pyridyl bromide 6-bromopyridine AKOS BBS-00004324 ALPHA-BROMOPYRIDINE bromopyridine BROMOPYRIDINE(2-) EINECS 203-641-6 MFCD00006219 monobromopyridine NSC 8031 o-Bromopyridine Pyridin-2-yl bromide Pyridine, 2-bromo- Pyridine, 2-bromo-, Pyridine,2-bromo Pyridine,2-bromo- TIMTEC-BB SBB003999 α-bromopyridine β-Bromopyridine

1.3 CAS No.: 109-04-6

1.4 CID: 7973

1.5 EINECS(EC#): 203-641-6

1.6 Molecular Formula: C5H4BrN (isomer)

1.7 Inchi: InChI=1S/C5H4BrN/c6-5-3-1-2-4-7-5/h1-4H

1.8 InChkey: IMRWILPUOVGIMU-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=CC=NC(=C1)Br

1.10 Isomers Smiles: C1=CC=NC(=C1)Br

2. Properties

2.1 Density: 1.65

2.1 Melting point: 193 °C

2.1 Boiling point: 192-194℃

2.1 Refractive index: 1.5705-1.5725

2.1 Flash Point: 54℃

2.1 Precise Quality: 156.95300

2.1 PSA: 12.89000

2.1 logP: 1.84410

2.1 Solubility: 20g/l

2.2 Appearance: Clear colorless to pale brown Liquid

2.3 Storage: Ambient temperatures.

2.4 Chemical Properties: dark red liquid

2.5 Color/Form: Clear colorless to pale brown

2.6 pKa: pK1: 0.71(+1) (25°C)

2.7 Water Solubility: Slightly miscible with water.

2.8 Stability: Stable. Flammable. Incompatible with strong oxidizing agents, strong acids, acid chlorides.

2.9 StorageTemp: Refrigerator

3. Use and Manufacturing

3.1 GHS Classification: Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 38 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H226 (23.68%): Flammable liquid and vapor [Warning Flammable liquids]
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
H310 (89.47%): Fatal in contact with skin [Danger Acute toxicity, dermal]
H311 (10.53%): Toxic in contact with skin [Danger Acute toxicity, dermal]
H315 (97.37%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (97.37%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (92.11%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P210, P233, P240, P241, P242, P243, P261, P262, P264, P270, P271, P280, P301+P310, P302+P350, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P370+P378, P403+P233, P403+P235, P405, and P501

3.2 Methods of Manufacturing: Derived from 2-aminopyridine by bromination.?In industrial production, hydrobromic acid (above 48%) is first cooled to below 0°C, 2-aminopyridine is slowly added, then liquid bromine is added dropwise under salt bath freezing, the rate of addition is used to control the reaction temperature below -5°C Is appropriate.?After the addition, dropwise add an aqueous solution of sodium nitrite, control the reaction temperature below 0°C, stir for 20-30 min, dropwise add 50% sodium hydroxide solution, extract the reaction solution with ether, wash with water, dry with anhydrous sodium sulfate, filter, and recover Diethyl ether, the residue was distilled under reduced pressure, collecting 88 ℃ -94 ℃/3333Pa distillate to obtain the finished product, the yield was 83.8%.

3.3 Purification Methods: Dry 2-bromopyridine over KOH for several days, then distil it from CaO under reduced pressure, and taking the middle fraction. [Beilstein 20/5 V 422.] 2-Bromopyridine Preparation Products And Raw materials Preparation Products

3.4 Usage: 2-Bromopyridine is a 2-halogenated pyridine used in the preparation of a variety of biologically active compounds such as antimalarial agents and beta-adrenoceptor agonist.

4. Safety and Handling

4.1 Hazard Codes: T

4.1 Risk Statements: R10;R23/24/25;R36/37/38

4.1 Safety Statements: S16;S26;S28;S36/37/39;S38;S45

4.1 Packing Group: II

4.1 Hazard Class: 6.1

4.1 Hazard Declaration: H301-H310-H315-H319-H335

4.1 RIDADR: UN 2929 6

4.1 Caution Statement: P280-P301 + P310 + P330-P302 + P352 + P310-P304 + P340 + P312-P305 + P351 + P338-P337 + P313

4.1 WGK Germany: 3

4.1 RTECS: US3850000

4.1 Safety: Hazard Codes:T,Xn,F
Risk Statements:10-24/25-36/37/38-23/24/25-20/21/22
10:Flammable
24/25:Toxic by inhalation, in contact with skin and if swallowed
36/37/38:Irritating to eyes, respiratory system and skin
23/24/25:Toxic by inhalation, in contact with skin and if swallowed
20/21/22:Harmful by inhalation, in contact with skin and if swallowed
Safety Statements:16-36/37-45-38-36/37/39-28A-26
16:Keep away from sources of ignition - No smoking
36/37:Wear suitable protective clothing and gloves
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
38:In case of insufficient ventilation, wear suitable respiratory equipment
36/37/39:Wear suitable protective clothing, gloves and eye/face protection
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
RIDADR:UN 2929 6.1/PG 2
WGK Germany:3
HazardClass:6.1
PackingGroup:II
Hazard Note:Toxic
HS Code:29333999

4.2 Specification: dark red liquid
Safety Statements:16-36/37-45-38-36/37/39-28A-26
16:Keep away from sources of ignition - No smoking
36/37:Wear suitable protective clothing and gloves
45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
38:In case of insufficient ventilation, wear suitable respiratory equipment
36/37/39:Wear suitable protective clothing, gloves and eye/face protection
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice

4.3 Toxicity: Abdominal cavity-mouse LDL0: 31.3 mg/kg

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 3

Acute toxicity - Dermal, Category 2

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	Danger
Hazard statement(s)	H301 Toxic if swallowed H310 Fatal in contact with skin H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P262 Do not get in eyes, on skin, or on clothing. 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	P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P310 Immediately call a POISON CENTER/doctor/\u2026 P361+P364 Take off immediately all contaminated clothing and wash it before reuse. 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	P405 Store locked up. P403+P233 Store in a well-ventilated place. Keep container tightly closed.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

Predict 1H proton NMR

7. Synthesis Route

109-04-6Total: 24 Synthesis Route

626-05-1 235 Suppliers

109-04-6 380 Suppliers

Literatures:
Mase; Houpis; Akao; Dorziotis; Emerson; Hoang; Iida; Itoh; Kamei; Kato; Kawasaki; Lang; Lee; Lynch; Maligres; Molina; Nemoto; Okada; Reamer; Song; Tschaen; Wada; Zewge; Volante; Reider; Tomimoto Journal of Organic Chemistry, 2001 , vol. 66, # 20 p. 6775 - 6786
Yield: ~98%

110-86-1 85 Suppliers

109-04-6 380 Suppliers

Literatures:
Gros, Philippe; Fort, Yves; Caubere, Paul Journal of the Chemical Society - Perkin Transactions 1, 1997 , # 24 p. 3597 - 3600
Yield: ~73%

109-09-1 215 Suppliers

109-04-6 380 Suppliers

Literatures:
Schlosser, Manfred; Cottet, Fabrice European Journal of Organic Chemistry, 2002 , # 24 p. 4181 - 4184
Yield: ~48%

View all

8. Precursor and Product

precursor:

68-12-2

624-28-2

109-72-8

96-22-0

52200-48-3

626-05-1

223463-14-7

110-86-1

78948-09-1

109-09-1

100-39-0

13534-89-9

107263-95-6

View all

product :

2402-92-8

5957-90-4

822-89-9

1970-80-5

366-18-7

91-02-1

4411-83-0

142-08-5

2835-33-8

132-22-9

3445-09-8

6952-68-7

4392-85-2

253-72-5

4479-74-7

4467-07-6

2766-64-5

2637-34-5

504-29-0

1008-89-5

626-05-1

261-05-2

694-85-9

1807-97-2

4350-51-0

View all

9. Other Information

9.0 Usage: 2-Bromopyridine is used in the preparation of a variety of biologically active compounds like antimalarial agents. It is also used to prepare beta-adrenoceptor agonist.

9.1 Storage Conditions: Derived from 2-aminopyridine by bromination.?In industrial production, hydrobromic acid (above 48%) is first cooled to below 0°C, 2-aminopyridine is slowly added, then liquid bromine is added dropwise under salt bath freezing, the rate of addition is used to control the reaction temperature below -5°C Is appropriate.?After the addition, dropwise add an aqueous solution of sodium nitrite, control the reaction temperature below 0°C, stir for 20-30 min, dropwise add 50% sodium hydroxide solution, extract the reaction solution with ether, wash with water, dry with anhydrous sodium sulfate, filter, and recover Diethyl ether, the residue was distilled under reduced pressure, collecting 88 ℃ -94 ℃/3333Pa distillate to obtain the finished product, the yield was 83.8%.

9.2 Storage features: Treasury is ventilated, low temperature and dry; stored separately from food materials

9.3 Manufacturing Info: Pyridine, 2-bromo-: ACTIVE

10. Computational chemical data

Molecular Weight: 157.998g/mol
Molecular Formula: C₅H₄BrN
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 156.95271
Monoisotopic Mass: 156.95271
Complexity: 56
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 1
Topological Polar Surface Area: 12.9
Heavy Atom Count: 7
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcYBiAAAAEAAAAAAAAAAAAAAAAAAAAAAsAAAAAAAAAAABgAAAHABAAAABOADBEgQ8gJIIEACgADBnRACCgCAxAiQI2CA4ZLgIIOLAkZGEIAhggADIyhYQAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==