[ CAS No. 5815-08-7 ] {[proInfo.proName]}

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Quality Control of [ 5815-08-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 5815-08-7 ]

SDS Specification

Alternatived Products of [ 5815-08-7 ]

Product Details of [ 5815-08-7 ]

CAS No. :	5815-08-7	MDL No. :	MFCD00042858
Formula :	C₉H₂₂N₂O	Boiling Point :	-
Linear Structure Formula :	C₄H₉OCH(N(CH₃)₂)₂	InChI Key :	HXRAMSFGUAOAJR-UHFFFAOYSA-N
M.W :	174.28	Pubchem ID :	79885
Synonyms :

Calculated chemistry of [ 5815-08-7 ] Expand+

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	52.29
TPSA :	15.71 ?2

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) :	-6.37 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.6
Log Po/w (XLOGP3) :	1.4
Log Po/w (WLOGP) :	1.21
Log Po/w (MLOGP) :	1.54
Log Po/w (SILICOS-IT) :	-0.06
Consensus Log Po/w :	1.34

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.54
Solubility :	5.04 mg/ml ; 0.0289 mol/l
Class :	Very soluble
Log S (Ali) :	-1.33
Solubility :	8.08 mg/ml ; 0.0464 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.1
Solubility :	13.9 mg/ml ; 0.08 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.26

Safety of [ 5815-08-7 ]

Signal Word:	Danger	Class:	3,8
Precautionary Statements:	P501-P270-P240-P210-P233-P243-P241-P242-P264-P280-P370+P378-P303+P361+P353-P301+P330+P331-P363-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P403+P235-P405	UN#:	2733
Hazard Statements:	H302-H314-H226	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 5815-08-7 ]

* 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 [ 5815-08-7 ]
Downstream synthetic route of [ 5815-08-7 ]

[ 5815-08-7 ] Synthesis Path-Upstream 1~1

1
[ 5815-08-7 ]
[ 60956-25-4 ]
[ 610794-15-5 ]

Reference： [1] Patent: WO2008/79918, 2008, A1, . Location in patent: Page/Page column 61-62
[2] Patent: WO2003/82826, 2003, A1, . Location in patent: Page/Page column 54
[3] Patent: WO2005/110991, 2005, A1, . Location in patent: Page/Page column 50-51

[ 5815-08-7 ] Synthesis Path-Downstream 1~11

1
[ 5815-08-7 ]
[ 3883-58-7 ]
4,4-Dimethyl-3,5-dioxo-cyclopentane-1,2-dicarbaldehyde [ No CAS ]

Reference： [1]Justus Liebigs Annalen der Chemie,1972,vol. 762,p. 62 - 72

2
[ 5815-08-7 ]
[ 3883-58-7 ]
4,5-Bis-[1-dimethylamino-meth-(E)-ylidene]-2,2-dimethyl-cyclopentane-1,3-dione [ No CAS ]

Reference： [1]Justus Liebigs Annalen der Chemie,1972,vol. 762,p. 62 - 72

3
[ 14001-61-7 ]
[ 5815-08-7 ]
[ 137475-74-2 ]

Reference： [1]Bulletin des Societes Chimiques Belges,1991,vol. 100,p. 533 - 538

4
[ 2346-00-1 ]
[ 5815-08-7 ]
2-(2-dimethylaminoethylidene)-4,5-dihydrothiazole [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1999,vol. 36,p. 1147 - 1150

5
[ 4360-68-3 ]
[ 5815-08-7 ]
[ 456-14-4 ]
[ 76128-69-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2003,vol. 1,p. 1638 - 1640

6
[ 4360-68-3 ]
[ 5815-08-7 ]
[ 57297-29-7 ]
2-cyclopropyl-4-phenyl-pyrimidine [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2003,vol. 1,p. 1638 - 1640

7
[ 5815-08-7 ]
[ 55984-93-5 ]
[ 872018-08-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	In N,N-dimethyl-formamide; at 75℃; for 72h;Inert atmosphere;	Methylterephthalonitrile (1.42g, 9.99mmol) and Bredereck's reagent (3.48g, 19.98mmol) were dissolved in DMF (15mL). The reaction mixture was heated at 75°C under nitrogen for 72hrs after which time the solvent was removed in vacuo. Trituration with Pet. Ether gave a bright yellow solid identified as 2-((E)- 2-dimethylamino-vinyl)-terephthalonitrile ester (1.88g, 0.95mmol, 95percent yield). XH NM (CD3OD) delta: 3.20 (6H, s), 5.34 (1H, d, J = 13.4Hz), 7.21 (1H, dd, J = 8.0Hz, 1.4Hz), 7.9 (1H, d, 13.4Hz), 7.61 (1H, d, J = 8.0Hz), 7.94 (1H, d, J =1.2Hz)
95%	In N,N-dimethyl-formamide; at 75℃; for 72h;Inert atmosphere;	Example 10A. 2-((E)-2-Dimethylamino-vinyl)-terephthalonitrile esterMethylterephthalonitrile (1.42g, 9.99mmol) and Bredereck's reagent (3.48g, 19.98mmol) were dissolved in DMF (15mL). The reaction mixture was heated at 75°C under nitrogen for 72hrs after which time the solvent was removed in vacuo. Trituration with Pet Ether gave a bright yellow solid identified as 2-((E)-2- dimethylamino-vinyl)-terephthalonitrile ester (1.88g, 0.95mmol, 95percent). H NMR (CD3OD) delta: 3.20 (6H, s), 5.34 (1H, d, J = 13.4Hz), 7.21 (1H, dd, J = 8.0Hz, 1.4Hz), 7.9 (1H, d, 13.4Hz), 7.61 (1H, d, J = 8.0Hz), 7.94 (1H, d, J =1.2Hz)
95%	In N,N-dimethyl-formamide; at 75℃;Inert atmosphere;	Into a 250-mL round-bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 2-methylbenzene-l,4-dicarbonitrile (4 g, 28.14 mmol, 1.00 equiv), [(tert-butoxy)(dimethylamino)methyl]dimethylamine (9.8 g, 56.23 mmol, 2.00 equiv) in N,N-dimethylformamide (50 mL). The resulting solution was stirred overnight at 75 °C, and then concentrated under vacuum. The resulting mixture was washed with 50 mL of hexane. The solids were collected by filtration. This provided 5.3 g (95percent) of 2-[(E)-2- (dimethylamino)ethenyl]benzene-l,4-dicarbonitrile as a yellow solid.

95%	In N,N-dimethyl-formamide; at 75℃;Inert atmosphere;	Step 2. 2-[(E)-2-(dimethylamino)ethenyl]benzene-1,4-dicarbonitrileInto a 250-mL round-bottom flask, which was purged and maintained with an inert atmosphere of nitrogen, was placed a solution of <strong>[55984-93-5]2-methylbenzene-1,4-dicarbonitrile</strong> (4 g, 28.14 mmol, 1.00 equiv), [(tert-butoxy)(dimethylamino)methyl]dimethylamine (9.8 g, 56.23 mmol, 2.00 equiv) in N,N-dimethylformamide (50 mL). The resulting solution was stirred overnight at 75° C., and then it was concentrated under vacuum. The resulting mixture was washed with 50 mL of hexane. The solids were collected by filtration. This provided 5.3 g (95percent) of 2-[(E)-2-(dimethylamino)ethenyl]benzene-1,4-dicarbonitrile as a yellow solid.
95%	In N,N-dimethyl-formamide; at 75℃; for 72h;Inert atmosphere;	Al. 2-({E)-2-Dimethylamino-vinYl)-terephthalonitrie ester Methylterephthalonitrile (1.42g, 9.99mmol) and Bredereck's reagent (3.48g, 19.98mmol) were dissolved in DMF (15mL). The reaction mixture was heated at 75 *C under nitrogen for 72hrs after which time the solvent was removed in vacuo. Trituration with Pet. Ether gave a bright yellow solid identified as 2-((E)- 2-dimethylamino-vinyl)-terephthalonitrile ester (1.88g, 0.95mmol, 95percent yield). 3H NMR (CD3OD) delta: 3.20 (6H, s), 5.34 (1H, d, J = 13.4Hz), 7.21 (1H, dd, J = 8.0Hz, 1.4Hz), 7.9 (1H, d, 13.4Hz), 7.61 (1H, d, J = 8.0Hz), 7.94 (1H, d, J =1.2Hz)
	In 1,2-dimethoxyethane; at 75℃; for 12h;	Methylterephthalonitrile (1.42 g, 1.0 mmol) and t-butoxybis(dimethylamine)methane (3.5 g, 2.0 mmol) were heated with 15 mL of DML at 75 °C for 12 h under N2. The DMF was removed and hexane was added. The precipitate formed was filtered and dried to give 1.85 g of the desired product. MS: 504.4, (M+H)+.

Reference： [1]Patent: WO2014/188211,2014,A1 .Location in patent: Page/Page column 44
[2]Patent: WO2015/22547,2015,A1 .Location in patent: Page/Page column 24
[3]Patent: WO2015/171526,2015,A2 .Location in patent: Paragraph 0110
[4]Patent: US2015/315198,2015,A1 .Location in patent: Paragraph 0239; 0241
[5]Patent: WO2016/83816,2016,A1 .Location in patent: Page/Page column 34
[6]Patent: WO2005/123050,2005,A2 .Location in patent: Page/Page column 165

8
[ 628-36-4 ]
[ 5815-08-7 ]
[ 16114-05-9 ]

Reference： [1]Synthesis,2008,p. 3380 - 3382

9
[ 5815-08-7 ]
[ 66116-81-2 ]
[ 5637-42-3 ]
[ 1383716-96-8 ]

Yield	Reaction Conditions	Operation in experiment
		Preparation of intermediate 4-(4-(2-(methylthio)-6-oxo-l,6-dihydropyrimidin-5- yl)pyrimidin-2-ylamino)benzonitrile (34) : (34)5-Acetyl-2-(methylthio)pyrimidin-4(3H)-one (33) (1.094 g, 5.94 mmol) was dissolved in l-tert-butoxy-N,N,N',N'-tetramethylmethanediamine (12.26 mL, 59.4 mmol), then the reaction mixture was heated at 120C for 6 hours. The reaction mixture was concentrated in vacuo, and dried over high vacuum for 1 hour. The crude intermediate was taken up in DMF (31.6 mL), then l-<strong>[5637-42-3](4-cyanophenyl)guanidine</strong> (2.076 g, 8.91 mmol) and K2C03 (4.10 g, 29.7 mmol) were added. The reaction mixture was heated at 120C for 48 hours. Additional 1 -<strong>[5637-42-3](4-cyanophenyl)guanidine</strong> (2.076 g, 8.91 mmol) and K2C03 (3.69 g, 26.7 mmol) were added, and the reaction mixture was stirred at 120C for additional 18 hours. The reaction mixture was cooled to rt, then was slowly poured into an ice-cooled IN HCl solution while stirring vigorously. The reaction mixture was neutralized with additional IN HCl, then the reaction mixture was allowed to stir for an additional 30 minutes. The resulting precipitate was filtered, washed multiple times with DI water, 2-propanol, then diethyl ether. The resulting crude product was dried over high vacuum for 18 hours to obtain the desired product as a red/brown solid (940 mg, 47% yield). MS (ES+): m/z = 337.2 (100) [MH+]. HPLC: tR = 1.35 minutes over 3 minutes. Purity: 72% [HPLC (LC/MS) at 220 nm].

Reference： [1]Patent: WO2012/85815,2012,A1 .Location in patent: Page/Page column 87-88

10
[ 5815-08-7 ]
[ 62621-09-4 ]
[ 1508296-89-6 ]

Yield	Reaction Conditions	Operation in experiment
70.1%	In N,N-dimethyl-formamide; at 143℃; for 3h;	ethyl 2-(2-(dimethylamino)vinyl)-4-nitrobenzoate [00148] To Intermediate 3A (1 1.35 g, 58.2 mmol) in DMF (15 ml) was added l-tert- butoxy-N,N,N',N'-tetramethylmethanediamine (39.6 ml, 192 mmol). The mixture was heated at 143 C for 3.0 h. DMF was removed by vacuum distillation at 70 C to leave a semi solid. The semi-solid was triturated with EtOAc/hexanes (1 :4) and stored at 4 C overnight. The precipitate was collected by filtration to give Intermediate 3B (10.2 g, 40.8 mmol, 70.1% yield) as a dark solid. lR NMR (400 MHz, chloroform-d) delta ppm 8.21 (d, J=2.20 Hz, 1 H) 7.87 (d, J=8.79 Hz, 1 H) 7.66 (dd, J=8.79, 2.20 Hz, 1 H) 7.02 (d, J=13.19 Hz, 1 H) 6.12 (d, J=13.74 Hz, 1 H) 3.91 (s, 3 H) 2.94 (s, 6 H).
69.7%	In N,N-dimethyl-formamide; at 143℃; for 3h;	Intermediate 3 B: 2-((E)-2-Dimethylamino-vinyl)-4-nitro-benzoic acid methyl ester j00130j To Intermediate 3A (6.6 g, 33.8 mmol) in DMF (9.0 mL) was added 1-tert- butoxy-N,N,N?,N?-tetramethylmethanediamine (23.04 mL, 112 mmol). The mixture washeated at 143 C for 3 h. The crude reaction mixture was vacuum distilled at 70 C toleave a semi-solid. The semi-solid was triturated with EtOAc/Hexanes (1:4) and stored at4 C overnight. The precipitate was collected by filtration to give Intermediate 3B (5.9 g,23.58 mmol, 69.7 % yield) as a dark solid. ?H NMR (400 MHz, CHLOROFORM-cl) oeppm 8.21 (d, J=2.20 Hz, 1 H) 7.87 (d, J=8.79 Hz, 1 H) 7.66 (dd, J=8.79, 2.20 Hz, 1 H)7.02 (d, J=13.19 Hz, 1 H) 6.12 (d, J=13.74 Hz, 1 H) 3.91 (s, 3 H) 2.94 (s, 6 H).

Reference： [1]Patent: WO2013/184734,2013,A1 .Location in patent: Paragraph 00147; 00148
[2]Patent: WO2014/201073,2014,A1 .Location in patent: Paragraph 00130

11
[ 5815-08-7 ]
[ 62621-09-4 ]
C₁₂H₁₄N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69 g	In N,N-dimethyl-formamide; at 140℃; for 3h;	To a solution of El (93 g, 476 mmol) in DMF (45 mL) was added l-tert-butoxy-N,N,N',N'- tetramethyl-methanediamine (249 g, 1.43 mol, 295 mL). The reaction mixture was stirred at l40C for 3 hr to give a brown mixture. TLC showed new spot. The mixture was cooled to room temperature and stirred at 0C for 30 min. Solid was precipitated out. After filtration, the filter cake was washed with EtOAc/PE and dried under reduced pressure to give compound E2 (69 g) as a purple powder.

Reference： [1]Patent: WO2019/197546,2019,A1 .Location in patent: Page/Page column 33; 50; 51

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Isomers

Technical Information

? Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions ? Chan-Lam Coupling Reaction ? Heat of Combustion ? Hydride Reductions ? Leuckart-Wallach Reaction ? Mannich Reaction ? Nomenclature of Ethers ? Petasis Reaction ? Preparation of Amines ? Preparation of Ethers ? Reactions of Amines ? Reactions of Ethers ? Specialized Acylation Reagents-Vilsmeier Reagent ? Ugi Reaction

Historical Records

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[ 5815-08-7 ]

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H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
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. 5815-08-7 ] {[proInfo.proName]}

Quality Control of [ 5815-08-7 ]

Related Doc. of [ 5815-08-7 ]

Product Details of [ 5815-08-7 ]

Calculated chemistry of [ 5815-08-7 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 5815-08-7 ]

Application In Synthesis of [ 5815-08-7 ]

[ 5815-08-7 ] Synthesis Path-Upstream 1~1

[ 5815-08-7 ] Synthesis Path-Downstream 1~11

Technical Information

Related Functional Groups of [ 5815-08-7 ]

Aliphatic Chain Hydrocarbons

Ethers

Amines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 5815-08-7 ]