[ CAS No. 54087-03-5 ] {[proInfo.proName]}

Name: 54087-03-5|6-Chloropicolinaldehyde|97%
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Quality Control of [ 54087-03-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 54087-03-5 ]

SDS Specification

Alternatived Products of [ 54087-03-5 ]

Product Details of [ 54087-03-5 ]

CAS No. :	54087-03-5	MDL No. :	MFCD09832941
Formula :	C₆H₄ClNO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XTRLIKXVRGWTKW-UHFFFAOYSA-N
M.W :	141.56	Pubchem ID :	10796848
Synonyms :

Calculated chemistry of [ 54087-03-5 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	34.63
TPSA :	29.96 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.02 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.02
Log Po/w (XLOGP3) :	1.61
Log Po/w (WLOGP) :	1.55
Log Po/w (MLOGP) :	0.4
Log Po/w (SILICOS-IT) :	2.16
Consensus Log Po/w :	1.35

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.16
Solubility :	0.981 mg/ml ; 0.00693 mol/l
Class :	Soluble
Log S (Ali) :	-1.85
Solubility :	1.99 mg/ml ; 0.0141 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.56
Solubility :	0.387 mg/ml ; 0.00274 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.3

Safety of [ 54087-03-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 54087-03-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 54087-03-5 ]
Downstream synthetic route of [ 54087-03-5 ]

[ 54087-03-5 ] Synthesis Path-Upstream 1~9

1
[ 33674-97-4 ]
[ 54087-03-5 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458
[2] Journal of Medicinal Chemistry, 1998, vol. 41, # 11, p. 1827 - 1837

2
[ 109-09-1 ]
[ 68-12-2 ]
[ 54087-03-5 ]

Reference： [1] Tetrahedron, 2006, vol. 62, # 26, p. 6166 - 6171
[2] Organic Letters, 2000, vol. 2, # 6, p. 803 - 805

3
[ 109-09-1 ]
[ 2591-86-8 ]
[ 54087-03-5 ]

Reference： [1] Tetrahedron, 2006, vol. 62, # 26, p. 6166 - 6171

4
[ 52313-59-4 ]
[ 54087-03-5 ]

Reference： [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 11, p. 1827 - 1837

5
[ 86209-84-9 ]
[ 54087-03-5 ]

Reference： [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 11, p. 1827 - 1837

6
[ 18368-63-3 ]
[ 54087-03-5 ]

Reference： [1] Patent: WO2005/12306, 2005, A2, . Location in patent: Page/Page column 60

7
[ 68-12-2 ]
[ 258506-66-0 ]
[ 54087-03-5 ]

Reference： [1] Tetrahedron Letters, 2014, vol. 55, # 36, p. 5074 - 5077

8
[ 4684-94-0 ]
[ 54087-03-5 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458

9
[ 109-09-1 ]
[ 54087-03-5 ]

Reference： [1] Tetrahedron Letters, 2014, vol. 55, # 36, p. 5074 - 5077

[ 54087-03-5 ] Synthesis Path-Downstream 1~5

1
[ 33674-97-4 ]
[ 54087-03-5 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1990,vol. 38,p. 2446 - 2458
[2]Journal of Medicinal Chemistry,1998,vol. 41,p. 1827 - 1837

Yield	Reaction Conditions	Operation in experiment
		The latter were refluxed for 2 hours with 1.6 g of sodium carbonate in 30 ml of water and 30 ml of methanol. The solution was then boiled with activated carbon, filtered and firstly extracted with carbon tetrachloride and then trichloromethane. The trichloromethane phase was rotated in and yielded approximately 4 g of 2-chloro-6-hydroxymethyl pyridine. The latter was dissolved in 100 ml of trichloromethane, mixed with 5 g of activated manganese dioxide and refluxed for 2.5 hours. The manganese dioxide was filtered off hot and the solution rotated in. 2.1 g of 6-chloropyridine-2-aldehyde were obtained.

3
[ 54087-03-5 ]
[ 1026587-36-9 ]

Yield	Reaction Conditions	Operation in experiment
86%	With diethylamino-sulfur trifluoride; In dichloromethane; at -20 - 27℃;Inert atmosphere;	(Diethylamino)sulfur trifluoride (2.4 ml_, 18.3 mmol) was added to a solution of a 2- pyridinecarboxaldehyde derivative (8.3 mmol) in DCM (30 ml_, anhydrous), drop-wise, under nitrogen in an acetone /C02 bath at -20 C. The resultant solution was allowed to warm to ambient temperature and then stirred until complete conversion was observed by TLC. The reaction was quenched with ice and then basified to pH 8-10 with solid sodium hydrogen carbonate. The layers were then separated, and the organic phase washed successively with water and then saturated brine solution, then dried (MgS04), concentrated in vacuo and purified by gradient flash chromatography, affording the 2- fluoromethylpyridine derivative.
29%	With diethylamino-sulfur trifluoride; In dichloromethane; at -20 - 20℃; for 16.0h;	A solution of 6-chloropyridine-2-carbaldehyde (5 g, 35.3 mmol) in DCM (50 mL) was stirred at 20 C for 1 h DAST (965 ml 60 0 mmol) was then added and the mixture was stirred at RT for 16 h. The mixture was neutralized to pH 7-8 with sat. aq. NaHCO3 and extracted with DCM (3 x 20 mL). The combined organic layers were washed with H2O, dried (Na2SO4) and concentrated under reduced pressure to afford the title product (1.65 g, 29%) as a black liquid. LCMS (Method A): 0.92 min; m/z: 164.0 [M+H]+.
29%	With diethylamino-sulfur trifluoride; In dichloromethane; at -20 - 20℃; for 16.0h;	A solution of 6-chloropyridine-2-carbaldehyde (5 g, 35.3 mmol) in DCM (50 mL) was stirred at 20 C for 1 h DAST (965 ml 60 0 mmol) was then added and the mixture was stirred at RT for 16 h. The mixture was neutralized to pH 7-8 with sat. aq. NaHCO3 and extracted with DCM (3 x 20 mL). The combined organic layers were washed with H2O, dried (Na2SO4) and concentrated under reduced pressure to afford the title product (1.65 g, 29%) as a black liquid. LCMS (Method A): 0.92 min; m/z: 164.0 [M+H]+.

29%

With diethylamino-sulfur trifluoride; In dichloromethane; at -20 - 20℃; for 16.0h;

A solution of 6-chloropyridine-2-carbaldehyde (5 g, 35.3 mmol) in DCM (50 mL) was stirred at 20 C for 1 h DAST (965 ml 60 0 mmol) was then added and the mixture was stirred at RT for 16 h. The mixture was neutralized to pH 7-8 with sat. aq. NaHCO3 and extracted with DCM (3 x 20 mL). The combined organic layers were washed with H2O, dried (Na2SO4) and concentrated under reduced pressure to afford the title product (1.65 g, 29%) as a black liquid. LCMS (Method A): 0.92 min; m/z: 164.0 [M+H]+.

Reference： [1]Patent: WO2011/95625,2011,A1 .Location in patent: Page/Page column 113
[2]Patent: WO2021/253095,2021,A1 .Location in patent: Page/Page column 81-82
[3]Patent: WO2021/253095,2021,A1 .Location in patent: Page/Page column 81-82
[4]Patent: WO2021/253095,2021,A1 .Location in patent: Page/Page column 81-82

4
[ 68-12-2 ]
[ 258506-66-0 ]
[ 54087-03-5 ]

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 5074 - 5077

5
[ 54087-03-5 ]
[ 20439-47-8 ]
C₁₈H₁₈Cl₂N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With calcium sulfate In dichloromethane at 20℃;	2. The synthesis of ligand L8 To the solution of 6-chloropyridine-2-carboxaldehyde (339 mg, 2.4 mmol) in CH2Cl2 (8 mL), (R,R)-1,2-cyclohexanediamine (139 mg, 1.2 mmol) was added and the mixture was stirred for 5 h at room temperature with the addition of CaSO4. The mixture was filtered followed by concentration of the filtrate in vacuo (to 1 mL). Then diethyl ether (2 mL) was added and the mixture was again concentrated in vacuo to 1 mL, followed by a further diethyl ether addition (2 mL). This solution was stored at -20 C for 1 h and then filtered to give a white precipitate ( 355 mg, 80% yield) which was dried at room temperature. 1H NMR (400 MHz, CDCl3), δ 8.21 (s, 2H), 7.86 (d, J=8.0 Hz, 2H), 7.63 (t, J=8.0 Hz, 2H), 7.28 (d, J=8.0 Hz, 2H), 3.52-3.45 (m, 2H), 1.89-1.76 (m, 6H), 1.53-1.47 (m, 2H); 13C NMR (100 MHz, CDCl3): δ 160.14, 155.20, 150.71, 139.08, 125.15, 119.41, 73.49, 32.54, 24.23; IR (KBr): 2935.3, 2857.4, 1651.3, 1850.6, 1556.2, 1439.1, 1326.4, 1307.2, 1158.8, 1136.8, 1072.6, 895.5, 794.7, 731.0 cm-1; HRMS (ESI): Exact mass calcd for C18H19Cl2N4 [M+H]+: 361.0981, found: 361.0976.

Reference： [1]Xie, Shiliang; Gao, Xiaotong; Zhou, Feng; Wu, Haihong; Zhou, Jian [Chinese Chemical Letters, 2020, vol. 31, # 2, p. 324 - 328]

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Code	Phrase
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
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P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
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Physical hazards
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
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H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
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H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
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H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
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H361d	Suspected of damaging the unborn child
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H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 54087-03-5 ] {[proInfo.proName]}

Quality Control of [ 54087-03-5 ]

Related Doc. of [ 54087-03-5 ]

Product Details of [ 54087-03-5 ]

Calculated chemistry of [ 54087-03-5 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 54087-03-5 ]

Application In Synthesis of [ 54087-03-5 ]

[ 54087-03-5 ] Synthesis Path-Upstream 1~9

[ 54087-03-5 ] Synthesis Path-Downstream 1~5

Related Functional Groups of [ 54087-03-5 ]

Chlorides

Aldehydes

Related Parent Nucleus of [ 54087-03-5 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 54087-03-5 ]

Related Parent Nucleus of
[ 54087-03-5 ]