[ CAS No. 19472-74-3 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 19472-74-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 19472-74-3 ]

SDS Specification

Alternatived Products of [ 19472-74-3 ]

Product Details of [ 19472-74-3 ]

CAS No. :	19472-74-3	MDL No. :	MFCD00001896
Formula :	C₈H₆BrN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BVCOJESIQPNOIF-UHFFFAOYSA-N
M.W :	196.04	Pubchem ID :	29625
Synonyms :

Calculated chemistry of [ 19472-74-3 ] Expand+

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 :	43.66
TPSA :	23.79 ?2

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) :	-5.88 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.84
Log Po/w (XLOGP3) :	2.27
Log Po/w (WLOGP) :	2.52
Log Po/w (MLOGP) :	2.52
Log Po/w (SILICOS-IT) :	2.81
Consensus Log Po/w :	2.39

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.86
Solubility :	0.268 mg/ml ; 0.00137 mol/l
Class :	Soluble
Log S (Ali) :	-2.41
Solubility :	0.769 mg/ml ; 0.00392 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.74
Solubility :	0.0353 mg/ml ; 0.00018 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.31

Safety of [ 19472-74-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362-P403+P233-P501	UN#:	N/A
Hazard Statements:	H302-H312-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 19472-74-3 ]

* 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 [ 19472-74-3 ]
Downstream synthetic route of [ 19472-74-3 ]

[ 19472-74-3 ] Synthesis Path-Upstream 1~1

1
[ 19472-74-3 ]
[ 74-88-4 ]
[ 57775-06-1 ]

Yield	Reaction Conditions	Operation in experiment
79%	With NaH In tetrahydrofuran; water	A/ Preparation of 2-(2'-bromophenyl)-2-methylpropionitrile: A solution of 2-(2'-bromophenyl)-acetonitrile (7.5 g; 38 mmole) and iodomethane (16.2 g; 114 mmole) in THF (30 ml) was slowly added (60 minutes) to a suspension of NaH (4.0 g; 100 mmole) in THF (100 ml) which had been refluxed in an inert atmosphere. The reaction was exothermic. Refluxing was continued for 2.5 h. The reaction mixture was then stirred at room temperature for 15 h. The solvent was evaporated off under reduced pressure; the residue was taken up in 100 ml of water and extracted with 2100 ml of tertiobutylmethylether. The organic phases were combined, washed with 3100 ml of a saturated NaCl solution; dried over MgSO₄ then filtered. The solvent was evaporated off under reduced pressure. The desired product was obtained as a colorless oil after distillation under reduced pressure (T=125-140° C.; p=0.1 mbar). Yield=79percent. This substance was also made using the procedure described by W. E. Parham and L. D. Jones (see J. Org. Chem., (1976), 41, pp 1187-1191) with a yield of 90percent. Physical characteristics: ¹ H NMR (CDCl₃) 1.90 ppm (s; 6H); 7.19 ppm (m; 1H; J=7.5 Hz); 7.35 ppm (t; 1H; J=7.5 Hz); 7.49 ppm (m; 1H; J=7.5 Hz); 7.67 ppm (d; 1H; J=7.5 Hz). ¹³ C NMR: (CDCl₃) 27.13 ppm; 37.64 ppm; 123.08 ppm; 123.92 ppm; 127.76 ppm; 128.49 ppm; 130.15 ppm; 136.18 ppm; 138.77 ppm. MS (IE; 70 eV) 225/223 (M⁺; 80percent); 210/208 (100percent); 183/181 (75percent); 102 (20percent).

Reference： [1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 31, p. 6404 - 6409
[2] Journal of Organic Chemistry, 1998, vol. 63, # 18, p. 6414 - 6420
[3] Patent: US5968920, 1999, A,
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1979, p. 829 - 837
[5] Journal of the American Chemical Society, 2010, vol. 132, # 2, p. 466 - 467
[6] Patent: WO2014/26243, 2014, A1, . Location in patent: Page/Page column 144

[ 19472-74-3 ] Synthesis Path-Downstream 1~7

1
[ 1001-26-9 ]
[ 19472-74-3 ]
C₁₃H₁₂BrNO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Ethyl 3-ethoxyacrylate (36.9 kg, 255. 0MOLES), 2-BROMOPHENYL acetonitrile (50 kg, 255. 1MOLES), and tetrahydrofuran (57 L) were combined in reactor 1 and the resultant solution was stirred at 25°C until needed (4 hours.). Palladium II acetate (1.3 kg, 5. 7MOLES), tricyclohexylphosphine (1.9 kg, 6. 7MOLES), and tetrahydrofuran (148 L) were combined in reactor 2 and the resultant mixture was stirred for 30 minutes at 25°C. The mixture was then cooled to 5°C and sodium t-butoxide (61.3 kg, 637.7 moles) was added to reactor 2 at 5°C. The resulting mixture was warmed to 15°C and stirred for 15 minutes and then cooled back to 5°C. The contents in reactor 1 were then slowly charged to reactor 2 over 2 hours. at 10°C and then the contents in reactor 2 were stirred for 15 minutes at 10°C. Reactor 2 was then SLOWLY HEATED TO 60°C AT A RATE OF 8 TO 2°C PER HOUR (5 HOURS. ) AND THEN HELD AT 60°C FOR 4 hours. The reaction was then cooled to 5°C and ethylene glycol was added at 5°C. The Tetrahydrofuran in the reaction was then distilled off. The reaction was again cooled to 10°C and sulfuric acid (88.4 kg) added over 1.5 hours at 10°C. The reaction was heated to 40°C at a rate of 8 to 12°C per hour (3 hours) and held at 40°C for 8 hours. The reaction was cooled to 10°C and ammonium hydroxide (44.8 kg) and water (201 L) were added. The slurry was warmed to 20°C and granulated for 2 hours. The solid was filtered and washed with water (61 L). The crude solid was recharged to the reactor and water (220 L) added. The slurry was granulated at 20°C for 4.5 hours and then filtered. The filter cake was washed with water (61 L) and the product dried at 55°C. The melting point was 227-229°C

Reference： [1]Patent: WO2004/48318,2004,A1 .Location in patent: Page 7-8

2
[ 1001-26-9 ]
[ 19472-74-3 ]
[ 3375-31-3 ]
[ 2622-14-2 ]
3-(ethoxy-hydroxy-methylene)-3H-indene-1-carbonitrile, sodium salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium chloride; sodium t-butanolate; In 1,2-dimethoxyethane;	Example 5 3-(ETHOXY-HYDROXY-METHYLENE)-3H-INDENE-1-CARBONITRILE, SODIUM SALT A solution of tricyclohexylphosphine (21.5 mg, 0.0770 mmol) in ethylene glycol dimethyl ether (10 mL) under nitrogen was charged with palladium (II) acetate (11.5 mg, 0.0510 mmol). The reaction was stirred at room temperature until the solution was homogenous (approx. 15 minutes), cooled to 0° C. and charged with sodium tert-butoxide (2.53 g, 25.5 mmol). After 5 minutes a solution of 2-bromo-phenylacetonitrile (1.32 mL, 10.2 mmol) and ethyl-3-ethoxyacrylate (1.47 mL, 10.2 mmol) in ethylene glycol dimethyl ether (10 ml) was added dropwise over 10 minutes. Upon complete addition, the reaction was warmed to room temperature then heated to 85° C. for 1 hour. The reaction was cooled to room temperature then diluted with ethyl acetate (50 mL) and poured into aqueous potassium dihydrogen phosphate (0.25 M, 50 mL), pH=7. The aqueous layer was saturated by addition of sodium chloride as solid and the organic layer separated and washed with aqueous saturated sodium chloride (1*50 mL), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo affording 3-(ethoxy-hydroxy-methylene)-3H-indene-1-carbonitrile, sodium salt, as a dark brown oil (1.74 g, 84percent) which solidifies on standing. 1H NMR (400 MHz, CD3CN) delta8.04 (d, 1H, J=6.0), 7.58 (s, 1H), 7.43 (d, 1H, J=6.0), 6.98-6.91 (m, 2H), 4.25 (q, 2H, J=7.2), 1.35 (t, 3H, J=7.2); 13C NMR (100 MHz, CD3CN) delta166.7, 135.5, 132.3, 131.3, 122.8, 120.5, 119.0, 118.4, 117.7, 103.3, 79.2, 58.2, 14.6; IR (ATR, neat) 2176, 1597, 1465, 1257, 1195,1068, 1029, 754 cm-1.

Reference： [1]Patent: US2003/60624,2003,A1

3
[ 34846-90-7 ]
[ 19472-74-3 ]
[ 77-92-9 ]
4-(2-bromo-phenyl)-4-cyano-but-3-enoic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With sodium chloride; sodium t-butanolate; In tetrahydrofuran;	Example 3 4-(2-BROMO-PHENYL)-4-CYANO-BUT-3-ENOIC ACID METHYL ESTER A solution of 2-bromo-phenylacetonitrile (6.62 mL, 51.0 mmol) and methyl-3-methoxyacrylate (5.32 mL, 49.5 mmol) in tetrahydrofuran (10 ml) was added to a suspension of sodium tert-butoxide (5.05 g, 51.0 mmol) in tetrahydrofuran (70 mL) at 0° C. over 10 minutes under a stream of nitrogen. The reaction mixture was warmed to room temperature and after 15 minutes diluted with methyl tert-butyl ether (240 mL). To the mixture was added 0.2 N aqueous citric acid until the aqueous layer had a pH of 2 (80 mL). The organic layer was separated and washed with a saturated aqueous solution of sodium chloride (2*80 mL), dried over anhydrous sodium sulfate, filtered through a pad of Celite and silica (4:1) and concentrated in vacuo to provide 4-(2-bromo-phenyl)-4-cyano-but-3-enoic acid methyl ester as a pale yellow oil (13.8 g, 96percent). Major isomer 1H NMR (400 MHz, CDCl3) delta7.59 (dd, 1H, J =7.6, 1.2), 7.57-719 (m, 3H), 6.71 (t, 1H, J=7.1), 3.71 (s, 3H), 3.61 (d, 2H, J=7.1); 13C NMR (100 MHz, CDCl3) delta169.7, 144.4, 133.7, 131.4, 131.1, 128.3, 122.5, 118.1, 117.3, 115.3, 52.7, 36.6; IR (ATR, neat) 1737, 1434, 1319, 1199, 1171, 1026, 755 cm-1. Minor isomer 1H NMR (400 MHz, CDCl3) delta7.61 (dd, 1H, J=7.6, 1.0), 7.57-7.19 (m, 3H), 6.9 (t,1H, J=7.5), 3.64 (s, 3H), 3.06 (d, 2H, J=7.5).

Reference： [1]Patent: US2003/60624,2003,A1

4
[ 3314-30-5 ]
[ 19472-74-3 ]
[ 60987-27-1 ]

Yield	Reaction Conditions	Operation in experiment
41%	With potassium phosphate; In dimethyl sulfoxide; at 130℃; for 24h;Inert atmosphere;	General procedure: A flask was equipped with a magnetic stir bar and charged with 1Hpyrrole-2-carbaldehyde (2a; 19.0 mg, 0.2 mmol, 1.0 equiv), 2-bromophenylacetonitrile(1a; 39.2 mg, 0.2 mmol, 1.0 equiv), and K3PO4(63.6 mg, 0.3 mmol, 1.5 equiv). The flask was evacuated and filledwith N2, and then anhydrous DMSO (2.0 mL) was introduced via a syringe.The flask was heated in a 130 °C oil bath for 24 h, at which timeTLC analysis [petroleum ether (bp 60?90 °C)?EtOAc, 10:1] indicatedcomplete consumption of 2a and 1a. The reaction mixture was cooledto r.t. and added to a sat. solution of NaCl (20 mL) and extracted withEtOAc (3 × 10 mL). The combined organic layers were dried (Na2SO4)and filtered. The filtrate was concentrated, and the residue was purified by column chromatography on SiO2 [petroleum ether (bp 60?90°C)?EtOAc, 10:1 to 30:1] to give 3ai; Yield: 19.9 mg (41percent); tan solid; mp 251.7?252.8 °C.

Reference： [1]Synthesis,2015,vol. 47,p. 1913 - 1921

5
[ 19472-74-3 ]
[ 21906-31-0 ]

Reference： [1]Organic Letters,2018,vol. 20,p. 4223 - 4226

6
[ 1001-26-9 ]
[ 19472-74-3 ]
3-Cyano-indan-1-carboxylic acid, ethyl ester [ No CAS ]

Reference： [1]Patent: US2003/60624,2003,A1

7
[ 19472-74-3 ]
[ 40138-17-8 ]
3-methylphenanthrene-9-carbonitrile [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 14593 - 14596
Angew. Chem.,2018,vol. 130,p. 14801 - 14805,5

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Isomers

Technical Information

? Alkyl Halide Occurrence ? Benzylic Oxidation ? Birch Reduction ? Blaise Reaction ? Blanc Chloromethylation ? Catalytic Hydrogenation ? Complex Metal Hydride Reductions ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Ritter Reaction ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Thorpe-Ziegler Reaction ? Vilsmeier-Haack Reaction

Historical Records

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H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
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
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
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

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[ CAS No. 19472-74-3 ] {[proInfo.proName]}

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[ 19472-74-3 ] Synthesis Path-Upstream 1~1

[ 19472-74-3 ] Synthesis Path-Downstream 1~7

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Aryls

Bromides

Nitriles

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[ 19472-74-3 ]