[ CAS No. 109179-31-9 ]

Name: 109179-31-9|2-Bromo-3-methylbenzaldehyde|98%
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Quality Control of [ 109179-31-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 109179-31-9 ]

SDS Specification

Alternatived Products of [ 109179-31-9 ]

Product Details of [ 109179-31-9 ]

CAS No. :	109179-31-9	MDL No. :	MFCD18392002
Formula :	C₈H₇BrO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CYQUDJGXCABLPN-UHFFFAOYSA-N
M.W :	199.05	Pubchem ID :	13707076
Synonyms :

Calculated chemistry of [ 109179-31-9 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	44.5
TPSA :	17.07 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.78 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.95
Log Po/w (XLOGP3) :	2.44
Log Po/w (WLOGP) :	2.57
Log Po/w (MLOGP) :	2.52
Log Po/w (SILICOS-IT) :	3.12
Consensus Log Po/w :	2.52

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.99
Solubility :	0.204 mg/ml ; 0.00102 mol/l
Class :	Soluble
Log S (Ali) :	-2.44
Solubility :	0.72 mg/ml ; 0.00362 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.59
Solubility :	0.0512 mg/ml ; 0.000257 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.13

Safety of [ 109179-31-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 109179-31-9 ]

* 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 [ 109179-31-9 ]
Downstream synthetic route of [ 109179-31-9 ]

[ 109179-31-9 ] Synthesis Path-Upstream 1~8

1
[ 168886-97-3 ]
[ 109179-31-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	With pyridinium chlorochromate In dichloromethane at 20℃;	A solution of the (2-bromo-3-methylphenyl)methanol 35 (100mg, 0.49mmol, 1equiv), PCC (161mg, 0.75mmol, 1.5equiv), and Celite (0.48mg) in anhydrous CH₂Cl₂ (4.5mL) was stirred at room temperature overnight. The mixture was quenched by addition of brine and extracted with Et₂O. Combined organic layers were washed with water, brine, dried over Na₂SO₄, filtered, and concentrated under reduced pressure. Crude product was passed through a silica/Celite plug and concentrated to give 36 (94mg, 95percent) as a white solid. R_f=0.57 (Pentane/Et₂O 95:5). ¹H NMR (400MHz, CDCl₃) δ (ppm)=10.45 (d, ⁴J=0.8Hz, 1H, H-8), 7.75–7.73 (m, 1H, H-6), 7.48 (ddd, ³J=7.6Hz, ⁴J=1.6Hz, ⁵J=0.8Hz, 1H, H-4), 7.32 (br t, ³J=7.6Hz, 1H, H-5), 2.48 (s, 3H, H-7). ¹³C NMR (125MHz, CDCl₃) δ (ppm)=192.8 (C-8), 139.7 (C-3), 136.4 (C-4), 134.1 (C-1), 129.7 (C-2), 127.52 (C-5 or 6), 127.45 (C-5 or 6), 23.0 (C-7). IR (CDCl₃) ν (cm⁻¹)=3339, 2982, 2920, 2866, 1889, 1695, 1674, 1573, 1448, 1373, 1237, 1031, 912, 779, 690, 536. HRMS (GC FI, 10,000V) calculated for C₈H₇BrO [M^+·] 197.96803, found 197.96767 (Diff.: −1.80ppm). Mp=50°C.
89%	With pyridinium chlorochromate In dichloromethane at 20℃;	[00203] A flask was charged with (2-bromo-3-methylphenyl)methanol (5.00 g, 24.9 mmol, 1.00 equiv), pyridinium chlorochromate (16.2 g, 75.0 mmol, 3.00 equiv), and DCM (70 mL). The resulting solution was stirred overnight at rt and concentrated. The residue was chromatographed on a silica gel column (20:80 EtOAc/petroleum ether) to provide 2-bromo-3-methylbenzaldehyde (4.40 g, 89percent yield) as a white solid. GCMS (EI, m/z): 198 [M]+.

Reference： [1] Comptes Rendus Chimie, 2017, vol. 20, # 6, p. 665 - 681
[2] Patent: WO2016/149401, 2016, A2, . Location in patent: Paragraph 00203
[3] Photochemical and Photobiological Sciences, 2018, vol. 17, # 3, p. 290 - 301
[4] Patent: US2011/82109, 2011, A1, . Location in patent: Page/Page column 33
[5] Chemistry - An Asian Journal, 2018, vol. 13, # 17, p. 2401 - 2404

2
[ 131001-86-0 ]
[ 109179-31-9 ]

Reference： [1] Tetrahedron, 2008, vol. 64, # 52, p. 11852 - 11859
[2] Patent: WO2016/149401, 2016, A2,
[3] Comptes Rendus Chimie, 2017, vol. 20, # 6, p. 665 - 681

3
[ 53663-39-1 ]
[ 109179-31-9 ]

Reference： [1] Comptes Rendus Chimie, 2017, vol. 20, # 6, p. 665 - 681
[2] Photochemical and Photobiological Sciences, 2018, vol. 17, # 3, p. 290 - 301
[3] Chemistry - An Asian Journal, 2018, vol. 13, # 17, p. 2401 - 2404
[4] Patent: US2011/82109, 2011, A1,

4
[ 52780-15-1 ]
[ 109179-31-9 ]

Reference： [1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 13, p. 2493 - 2502

5
[ 576-22-7 ]
[ 109179-31-9 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1986, vol. 59, p. 3285 - 3286

6
[ 66790-58-7 ]
[ 109179-31-9 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1986, vol. 59, p. 3285 - 3286

7
[ 109179-31-9 ]
[ 53663-39-1 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 1986, vol. 59, p. 3285 - 3286

8
[ 109179-31-9 ]
[ 610794-15-5 ]

Reference： [1] Patent: US2016/9706, 2016, A1,

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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
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Environmental hazards
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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

Yield	Reaction Conditions	Operation in experiment
95%	With pyridinium chlorochromate; In dichloromethane; at 20℃;	A solution of the (2-bromo-3-methylphenyl)methanol 35 (100mg, 0.49mmol, 1equiv), PCC (161mg, 0.75mmol, 1.5equiv), and Celite (0.48mg) in anhydrous CH2Cl2 (4.5mL) was stirred at room temperature overnight. The mixture was quenched by addition of brine and extracted with Et2O. Combined organic layers were washed with water, brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. Crude product was passed through a silica/Celite plug and concentrated to give 36 (94mg, 95percent) as a white solid. Rf=0.57 (Pentane/Et2O 95:5). 1H NMR (400MHz, CDCl3) delta (ppm)=10.45 (d, 4J=0.8Hz, 1H, H-8), 7.75?7.73 (m, 1H, H-6), 7.48 (ddd, 3J=7.6Hz, 4J=1.6Hz, 5J=0.8Hz, 1H, H-4), 7.32 (br t, 3J=7.6Hz, 1H, H-5), 2.48 (s, 3H, H-7). 13C NMR (125MHz, CDCl3) delta (ppm)=192.8 (C-8), 139.7 (C-3), 136.4 (C-4), 134.1 (C-1), 129.7 (C-2), 127.52 (C-5 or 6), 127.45 (C-5 or 6), 23.0 (C-7). IR (CDCl3) nu (cm?1)=3339, 2982, 2920, 2866, 1889, 1695, 1674, 1573, 1448, 1373, 1237, 1031, 912, 779, 690, 536. HRMS (GC FI, 10,000V) calculated for C8H7BrO [M+·] 197.96803, found 197.96767 (Diff.: ?1.80ppm). Mp=50°C.
89%	With pyridinium chlorochromate; In dichloromethane; at 20℃;	[00203] A flask was charged with (2-bromo-3-methylphenyl)methanol (5.00 g, 24.9 mmol, 1.00 equiv), pyridinium chlorochromate (16.2 g, 75.0 mmol, 3.00 equiv), and DCM (70 mL). The resulting solution was stirred overnight at rt and concentrated. The residue was chromatographed on a silica gel column (20:80 EtOAc/petroleum ether) to provide 2-bromo-3-methylbenzaldehyde (4.40 g, 89percent yield) as a white solid. GCMS (EI, m/z): 198 [M]+.
	With manganese(IV) oxide; In chloroform;	Example 67Synthesis of N-[(E)-3-(4'-hydroxy-6-methyl-biphenyl-2-yl)-2-methyl-acryloyl]-guanidine<Step 1>2-methyl-3-bromobenzoic acid (1 g, 4.65 mmol) and triethylamine (0.97 mL, 6.78 mmol) were dissolved in THF (20 mL), chloroformic acid ethyl (0.49 mL, 6.11 mmol) was added thereto while cooling it by ice and then stirred for 15 minutes. The precipitate was then eliminated by suction filtration, 1 g of ice and sodium borohydride (260 mg, 6.78 mmol) were added to the resulting filtrate while cooling it by ice and then stirred overnight. It was washed with water and saturated saline and then dried over anhydrous MgSO4. The solvent was then eliminated in vacuo to obtain a residue. The resulting residue was dissolved in chloroform (50 mL), manganese dioxide (2 g, 22.5 mmol) was added thereto and then stirred overnight. After filtration, the solvent was eliminated in vacuo and then purified by reversed phase HPLC (0.1percent TFA in water/CH3CN) to obtain an aldehyde (640 mg, 69percent).MS: 199

[ CAS No. 109179-31-9 ]

Quality Control of [ 109179-31-9 ]

Related Doc. of [ 109179-31-9 ]

Product Details of [ 109179-31-9 ]

Calculated chemistry of [ 109179-31-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 109179-31-9 ]

Application In Synthesis of [ 109179-31-9 ]

[ 109179-31-9 ] Synthesis Path-Upstream 1~8

[ 109179-31-9 ] Synthesis Path-Downstream 1~68

Related Functional Groups of [ 109179-31-9 ]

Aryls

Bromides

Aldehydes

Precautionary Statements-General

Prevention

Response

Storage

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Physical hazards

Health hazards

Environmental hazards

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Related Functional Groups of
[ 109179-31-9 ]