[ CAS No. 5372-81-6 ]

Name: 5372-81-6|Dimethyl aminoterephthalate|98%
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Quality Control of [ 5372-81-6 ]

COA NMR CNMR HPLC LC-MS

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Alternatived Products of [ 5372-81-6 ]

Product Details of [ 5372-81-6 ]

CAS No. :	5372-81-6	MDL No. :	MFCD00008427
Formula :	C₁₀H₁₁NO₄	Boiling Point :	345.6°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	-
M.W :	209.20	Pubchem ID :	-
Synonyms :

Computed Properties of [ 5372-81-6 ]

TPSA :Topological Polar Surface Area	-	H-Bond Acceptor Count :	-
XLogP3 :	-	H-Bond Donor Count :	-
SP3 :	-	Rotatable Bond Count :	-

Safety of [ 5372-81-6 ]

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 [ 5372-81-6 ]

Upstream synthesis route of [ 5372-81-6 ]
Downstream synthetic route of [ 5372-81-6 ]

[ 5372-81-6 ] Synthesis Path-Upstream 1~8

1
[ 5372-81-6 ]
[ 4637-24-5 ]
[ 313535-84-1 ]

Reference： [1] Patent: US6348474, 2002, B1, . Location in patent: Page column 83

2
[ 5372-81-6 ]
[ 77287-34-4 ]
[ 313535-84-1 ]

Reference： [1] Chemistry - A European Journal, 2016, vol. 22, # 1, p. 211 - 221

3
[ 5372-81-6 ]
[ 10312-55-7 ]

Reference： [1] Journal of Medicinal Chemistry, 1981, vol. 24, # 6, p. 735 - 742
[2] Inorganic Chemistry, 2018, vol. 57, # 3, p. 1040 - 1047

4
[ 5372-81-6 ]
[ 174074-89-6 ]

Reference： [1] Patent: WO2012/58671, 2012, A1,

5
[ 60-35-5 ]
[ 5372-81-6 ]
[ 174074-88-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	at 200℃; for 3 h;	Step 1: 2,4-Dioxo-l,2,3,4-tetrahydro-quinazoline-7-carboxylic acid methyl esterTo a 250 mL round bottom flask, 2-amino dimethyl terephthalate (3 g, 0.0143 mol) and urea (4.3 g, 0.0717 mol) were added. The reaction mixture was stirred at 200°C for 3 h. The reaction mixture was allowed to reach 100 °C and water was added. The aqueous reaction mixture was stirred at 100°C for 5-10 min then allowed to reach room temperature. The solid was filtered, washed with chloroform dried and azeotroped with toluene to afford the title compound [2.5 g, 80percent]. This material was taken to the next step without any further purification. 1H NMR; (400 MHz, DMSO-d₆): δ 11.25 (brs, 2H), 7.98 (d, 1H, J= 8.2 Hz), 7.78 (s, 1H), 7.65 (d, J= 8.2, 1.2 Hz, 1H), 3.98 (s, 3H): LC-MS (ESI): Calculated mass: 220.0; Observed mass: 221.0 [M+H]⁺ (RT: 0.19 min)

Reference： [1] Patent: WO2012/58671, 2012, A1, . Location in patent: Page/Page column 112-113

6
[ 5372-81-6 ]
[ 264276-14-4 ]

Reference： [1] Patent: WO2012/160464, 2012, A1,
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 11, p. 4521 - 4536
[3] Patent: US2014/155398, 2014, A1,

7
[ 5372-81-6 ]
[ 1258298-05-3 ]

Reference： [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 11, p. 4521 - 4536

8
[ 5372-81-6 ]
[ 1415800-43-9 ]

Reference： [1] Patent: CN104072403, 2016, B,

[ 5372-81-6 ] Synthesis Path-Downstream 1~7

1
[ 5292-45-5 ]
[ 5372-81-6 ]

Yield	Reaction Conditions	Operation in experiment
99.1%	With iron; ammonium chloride; In ethanol; water; for 0.5h;Reflux;	Nitro Reduction: To 50ml volume ratio of 1: 1 ethanol / water solution of ammonium chloride was added 2.3g, iron 2.3g, stirred heated to reflux for 30min; 2-nitro-dimethyl terephthalate (ie, compound II ) 10.0 g was dissolved in 25ml of ethanol, was added dropwise to the reaction flask slowly (to prevent the red material), after the addition was complete the reaction was continued at this temperature for 30min, TLC monitored the reaction was complete; cooled to room temperature, filtered through celite pad, the cake washed with until no product was adsorbed was washed with ethanol, and concentrated under reduced pressure to remove ethanol; aqueous layer was washed with saturated Na2CO3Solution was adjusted pH10, 50mlEA aqueous phase was extracted twice, the combined organic phase was washed by saturated sodium chloride, dried over anhydrous sodium sulfate, and evaporated to dryness to give 8.7g solid, i.e., 2-amino dimethyl terephthalate (i.e. compound III ), shown in Figure 2, a yield of 99.1percent,
98.9%	With hydrogen; In isopropyl alcohol; at 80℃; under 2250.23 Torr;pH 7 - 8;Large scale;	In the case of 200 kg of 2-nitro-terephthalic acid dimethyl ester, the catalyst used was a self-made catalyst. The total amount of catalyst used in the production was 0.1_3percent (0.2-6 kg) and the total amount of isopropyl alcohol was 8 times the raw material (1600 kg), in the hydrogenationThe order of the 2-nitro terephthalate, isopropanol and catalyst into the kettle is as follows:1, 2 - nitro - terephthalic acid dimethyl ester 200 kg, isopropyl alcohol 1600 kg added to the reactor, gas replacement.2, the introduction of hydrogen, hydrogenation reaction began to control the reaction temperature of 80 ± 5 ° C, the control reaction pressure of 0.3-1.0Mpa.3,The reaction ends the filtration catalyst,The filtrate cools down to below 20 degrees Celsius,Filter dry,To obtain the finished 2-amino terephthalate.4. The product obtained according to the above method was analyzed, and the conversion rate of dimethyl 2-nitro terephthalate was100percent, the selectivity of dimethyl 2-aminoterephthalate was 99.6percent, the content of dimethyl 2-aminoterephthalate was 99.9percentThe yield was 96.5percent.
	In tetrahydrofuran; methanol;	a) Dimethyl 2-aminoterephthalate 23.9 g (0.1 mol) of <strong>[5292-45-5]dimethyl 2-nitroterephthalate</strong> are hydrogenated in a mixture of 100 ml of methanol and 200 ml of tetrahydrofuran with palladium/charcoal at 5 bar and 20° C. After the catalyst has been removed by suction filtering the solvent is evaporated off and the residue is recrystallized from methanol. Yield 18-19 g, yellowish crystals m.p. 130-131° C.

Reference： [1]Patent: CN104072403,2016,B .Location in patent: Paragraph 0034
[2]Patent: CN106045868,2016,A .Location in patent: Paragraph 0013; 0014; 0015; 0016
[3]Liebigs Annalen der Chemie,1987,p. 833 - 838
[4]Canadian Journal of Chemistry,1986,vol. 64,p. 1969 - 1973
[5]Journal of the Chemical Society,1905,vol. 87,p. 1265
[6]Journal of the Chemical Society,1905,vol. 87,p. 1265
[7]Monatshefte fur Chemie,1912,vol. 33,p. 152,156, 166
[8]Justus Liebigs Annalen der Chemie,1912,vol. 393,p. 25
[9]Australian Journal of Chemistry,1997,vol. 50,p. 1159 - 1182
[10]Chemical Communications,2016,vol. 52,p. 7719 - 7722
[11]Chemistry - A European Journal,2018,vol. 24,p. 4234 - 4238
[12]Patent: US5185442,1993,A

2
[ 5292-45-5 ]
[ 5372-81-6 ]
hydroxyamino-terephthalic acid dimethyl ester [ No CAS ]

Reference： [1]Journal of the Chemical Society,1905,vol. 87,p. 1265

3
[ 5372-81-6 ]
[ 636-94-2 ]

Reference： [1]Journal of Materials Chemistry,2007,vol. 17,p. 1981 - 1988

4
[ 75680-92-1 ]
[ 5372-81-6 ]
2-ethyl 7-methyl 10-oxo-10H-pyridazino[6,1-b]quinazoline-2,7-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethanol; chloroform;	Step A. A mixture of <strong>[75680-92-1]ethyl 6-chloro-3-pyridazinecarboxylate</strong> (0.52 g, 2.79 mmol, Example 2, Step A) and dimethyl aminoterephthalate (0.61 g, 2.92 mmol, Aldrich Chemical Co.) was heated as a melt at 165-170 C. for 15 min. The resulting brown solid was dissolved into 50 mL of chloroform:ethanol (4:1), washed with 50 mL of 10% ammonium hydroxide solution, dried (MgSO4), filtered and concentrated. The crude oily solid was chromatographed (silica gel, 50% hexanes-50% ethyl acetate) to afford 2-ethyl 7-methyl 10-oxo-10H-pyridazino[6,1-b]quinazoline-2,7-dicarboxylate as a yellow solid, mp 202-204 C. dec.

Reference： [1]Patent: US5340808,1994,A

5
[ 73217-11-5 ]
[ 5372-81-6 ]
[ 1028694-66-7 ]

Reference： [1]Chemistry of Heterocyclic Compounds,2007,vol. 43,p. 460 - 469

6
[ 5372-81-6 ]
[ 264276-14-4 ]

Reference： [1]Patent: WO2012/160464,2012,A1
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 4521 - 4536
[3]Patent: US2014/155398,2014,A1

7
[ 5372-81-6 ]
[ 1415800-43-9 ]

Reference： [1]Patent: CN104072403,2016,B

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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H316	Causes mild skin irritation
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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. 5372-81-6 ]

Quality Control of [ 5372-81-6 ]

Related Doc. of [ 5372-81-6 ]

Product Details of [ 5372-81-6 ]

Computed Properties of [ 5372-81-6 ]

Safety of [ 5372-81-6 ]

Application In Synthesis of [ 5372-81-6 ]

[ 5372-81-6 ] Synthesis Path-Upstream 1~8

[ 5372-81-6 ] Synthesis Path-Downstream 1~7

Related Functional Groups of [ 5372-81-6 ]

Amines

Aryls

Esters

Precautionary Statements-General

Prevention

Response

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Health hazards

Environmental hazards

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Related Functional Groups of
[ 5372-81-6 ]