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Cas Database

Name	6-Bromopyridine-2-carbaldehyde	EINECS	-0
CAS No.	34160-40-2	Density	1.683 g/cm³
PSA	29.96000	LogP	1.65660
Solubility	Soluble in dichloromethane, ether, ethyl acetate and methanol. Insoluble in water.	Melting Point	81-85 °C(lit.)
Formula	C₆H₄BrNO	Boiling Point	248.2 °C at 760 mmHg
Molecular Weight	186.008	Flash Point	103.9 °C
Transport Information	N/A	Appearance	Light yellow flakes
Safety	26-36-36/37/39-16	Risk Codes	36/37/38-20/21/22-10
Molecular Structure		Hazard Symbols	Xn, Xi, F
Synonyms	Picolinaldehyde,6-bromo- (8CI);2-Bromo-6-formylpyridine;2-Bromopyridine-6-carboxaldehyde;2-Bromopyridyl-6-carboxaldehyde;2-Formyl-6-bromopyridine;6-Bromo-2-formylpyridine;6-Bromo-2-pyridinecarbaldehyde;6-Bromo-2-pyridinecarboxaldehyde;6-Bromopicolylaldehyde;6-Bromopyridine-2-aldehyde;Bromo-2-pyridinecarboxaldehyde;	Article Data	57

6-Bromopyridine-2-carbaldehyde Synthetic route

: 33674-96-3
2-bromo-6-(hydroxymethyl)pyridine

: 34160-40-2
6-bromo-2-pyridinecarbaldehyde

Conditions

Conditions	Yield
With fluorosulfonyl fluoride; potassium carbonate; dimethyl sulfoxide at 20℃; for 12h; chemoselective reaction;	98%
With phosphoric acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide for 1.5h; Ambient temperature;	89%
With 1-iodobenzoic acid In dimethyl sulfoxide at 20℃;
With phosphoric acid; dicyclohexyl-carbodiimide In dimethyl sulfoxide at 25℃; for 1.5h;
With 2-Iodobenzoic acid In dimethyl sulfoxide at 20℃; for 2h;

: 626-05-1
2,6-Dibromopyridine

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 34160-40-2
6-bromo-2-pyridinecarbaldehyde

Conditions

Conditions	Yield
Stage #1: 2,6-Dibromopyridine With n-butyllithium; butyl magnesium bromide In tetrahydrofuran; hexane; toluene at -10 - -5℃; for 3.5h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane; toluene at -10 - -5℃; for 0.5h; Further stages.;	97%
Stage #1: 2,6-Dibromopyridine With n-butyllithium; butyl magnesium bromide In tetrahydrofuran; hexane; toluene at -10℃; for 3h; Stage #2: N,N-dimethyl-formamide In toluene at -10 - -5℃; for 1h; Stage #3: With citric acid at 20℃; for 0.166667h;	95%
Stage #1: 2,6-Dibromopyridine With n-butyllithium In tetrahydrofuran; hexane at -70℃; for 2h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -70 - 0℃;	94.2%

: 626-05-1
2,6-Dibromopyridine

: 109-72-8, 29786-93-4
n-butyllithium

: 693-04-9
butyl magnesium bromide

: 34160-40-2
6-bromo-2-pyridinecarbaldehyde

Conditions

Conditions	Yield
With acetic acid In tetrahydrofuran; hexane; N,N-dimethyl-formamide; toluene	95%

: 109-04-6
2-bromo-pyridine

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 34160-40-2
6-bromo-2-pyridinecarbaldehyde

Conditions

Conditions	Yield
Stage #1: 2-bromo-pyridine With n-butyllithium In tetrahydrofuran; hexane at -78 - -70℃; for 2.5h; Inert atmosphere; Schlenk technique; Stage #2: N,N-dimethyl-formamide With zinc chloride*2(tetrahydrofuran) In tetrahydrofuran; hexane at -78 - 40℃; Inert atmosphere; Schlenk technique;	90.4%

: 82315-66-0
2-bromo-6-(dibromomethyl) pyridine

: 34160-40-2
6-bromo-2-pyridinecarbaldehyde

Conditions

Conditions	Yield
With calcium carbonate In water for 8h; Heating;	86%

: 626-05-1
2,6-Dibromopyridine

: 1068-55-9
isopropylmagnesium chloride

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

A: 5431-44-7
2,6-Pyridinedicarboxaldehyde

B: 34160-40-2
6-bromo-2-pyridinecarbaldehyde

C: 153646-83-4
6-isopropyl-2-pyridinecarboxaldehyde

Conditions

Conditions	Yield
Stage #1: 2,6-Dibromopyridine; isopropylmagnesium chloride In tetrahydrofuran at 20℃; for 5h; Stage #2: N,N-dimethyl-formamide With acetic acid at 0℃;	A 1% B 85% C 6%

...Expand

: 5315-25-3
2-bromo-6-methylpyridine

: 34160-40-2
6-bromo-2-pyridinecarbaldehyde

Conditions

Conditions	Yield
With selenium(IV) oxide In 1,4-dioxane at 80℃; for 16h;	71%
Multi-step reaction with 2 steps 1: 88 percent / N-bromosuccinimide; benzoylperoxide / CCl4 / 4 h / Heating 2: 86 percent / CaCO3 / H2O / 8 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 53 percent / KMnO4 / H2O / Heating 2: 1) NEt3, ethyl chloroformate, 2) LiAlH4 / 1) benzene, rt, 1 h, 2) THF, -78 deg C, 30 min 3: 89 percent / DMSO, N,N'-dicyclohexylcarbodiimide, H3PO4 / 1.5 h / Ambient temperature View Scheme
Stage #1: 2-bromo-6-methylpyridine With bromine In dichloromethane; water at 10 - 50℃; for 10h; Stage #2: With hexamethylenetetramine In ethanol at 40℃; for 12h; Stage #3: With sulfuric acid; acetic acid In ethanol at 90℃; for 1h;	62.3 g

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 34160-40-2
6-bromo-2-pyridinecarbaldehyde

Conditions

Conditions	Yield
Stage #1: With n-butyllithium; n-BuMgCl In tetrahydrofuran; H2O; hexane; N,N-dimethyl-formamide; toluene at -10℃; for 0.5h; Stage #2: 2,6-Dibromopyridine In tetrahydrofuran; hexane; toluene at -10℃; for 2.5h; Stage #3: N,N-dimethyl-formamide With citric acid more than 3 stages;	52%

: 626-05-1
2,6-Dibromopyridine

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

A: 5431-44-7
2,6-Pyridinedicarboxaldehyde

B: 34160-40-2
6-bromo-2-pyridinecarbaldehyde

Conditions

Conditions	Yield
Stage #1: 2,6-Dibromopyridine With n-butyllithium; butyl magnesium bromide In tetrahydrofuran at -10℃; Stage #2: N,N-dimethyl-formamide at 0℃;	A 43% B 49%

: 37709-60-7
2-(6-bromopyridinyl)lithium

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 34160-40-2
6-bromo-2-pyridinecarbaldehyde

Conditions

Conditions	Yield
In tetrahydrofuran at -75℃; for 0.25h; Yield given;

6-Bromopyridine-2-carbaldehyde Chemical Properties

Molecule structure of 6-Bromo-2-pyridinecarboxaldehyde (CAS NO.34160-40-2) :

IUPAC Name: 6-bromopyridine-2-carbaldehyde
Molecular Weight: 186.00606 g/mol
Molecular Formula: C₆H₄BrNO
Density: 1.683 g/cm³
Melting Point: 81-85 °C(lit.)
Boiling Point: 248.2 °C at 760 mmHg
Flash Point: 103.9 °C
Molar Volume: 110.5 cm³
Polarizability: 15.37*10^-24 cm³
Surface Tension: 52.1 dyne/cm
Enthalpy of Vaporization: 48.54 kJ/mol
Vapour Pressure: 0.0246 mmHg at 25 °C
Storage temp.: Refrigerator (+4 °C)
Sensitive: air sensitive
Appreance: light yellow flakes
XLogP3-AA: 1.7
H-Bond Acceptor: 2
Rotatable Bond Count: 1
Exact Mass: 184.947626
MonoIsotopic Mass: 184.947626
Topological Polar Surface Area: 30
Heavy Atom Count: 9
Complexity: 107
Canonical SMILES: C1=CC(=NC(=C1)Br)C=O
InChI: InChI=1S/C6H4BrNO/c7-6-3-1-2-5(4-9)8-6/h1-4H
InChIKey: QWFHFNGMCPMOCD-UHFFFAOYSA-N
Product Categories: Pyridine; Aldehydes; Pyridines; Nucleotides and Nucleosides; Bases & Related Reagents; Nucleotides; C6Heterocyclic Building Blocks; Halogenated Heterocycles; Heterocyclic Building Blocks; Building Blocks

6-Bromopyridine-2-carbaldehyde Uses

6-Bromo-2-pyridinecarboxaldehyde (CAS NO.34160-40-2) is a useful synthetic intermediate.

6-Bromopyridine-2-carbaldehyde Safety Profile

Hazard Codes: Irritant Xi, Harmful Xn, F
Risk Statements: 36/37/38-20/21/22-10
R36/37/38: Irritating to eyes, respiratory system and skin
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed
R10: Flammable
Safety Statements: 26-36-36/37/39-16
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
S36: Wear suitable protective clothing
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection
S16: Keep away from sources of ignition
WGK Germany: 3
Hazard Note: Irritant

6-Bromopyridine-2-carbaldehyde Specification

6-Bromo-2-pyridinecarboxaldehyde (CAS NO.34160-40-2) is also called 6-Bromopyridine-2-carbaldehyde ; 6-Bromo-2-formylpyridine ; 6-Bromopyridine-2-barboxaldehyde .

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