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7149-18-0

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7149-18-0 Usage

Chemical Properties

light yellow crystalline powder

Check Digit Verification of cas no

The CAS Registry Mumber 7149-18-0 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,1,4 and 9 respectively; the second part has 2 digits, 1 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 7149-18:
(6*7)+(5*1)+(4*4)+(3*9)+(2*1)+(1*8)=100
100 % 10 = 0
So 7149-18-0 is a valid CAS Registry Number.
InChI:InChI=1/C8H13NO2/c1-2-11-8(10)6-4-3-5-7(6)9/h6,9H,2-5H2,1H3/b9-7+/t6-/m1/s1

7149-18-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name ethyl 2-aminocyclopentene-1-carboxylate

1.2 Other means of identification

Product number -
Other names 2-amino-1-cyclopentene-1-carboxylate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:7149-18-0 SDS

7149-18-0Synthetic route

2-ethoxycarbonyl-1-cyclopentanone
611-10-9

2-ethoxycarbonyl-1-cyclopentanone

ethyl 2-amino-1-cyclopentene-1-carboxylate
7149-18-0

ethyl 2-amino-1-cyclopentene-1-carboxylate

Conditions
ConditionsYield
With ammonia; silica gel at 20℃; for 0.166667h;99%
With ammonium acetate; tetraethoxy orthosilicate In ethanol Heating;90%
With tetraethoxy orthosilicate; ammonium acetate In ethanol for 6h; Reflux; Inert atmosphere;82%
4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

ethyl bromoacetate
105-36-2

ethyl bromoacetate

A

ethyl 2-amino-1-cyclopentene-1-carboxylate
7149-18-0

ethyl 2-amino-1-cyclopentene-1-carboxylate

B

(Z)-ethyl 2-(pyrrolidin-2-ylidene)acetate
35150-22-2

(Z)-ethyl 2-(pyrrolidin-2-ylidene)acetate

Conditions
ConditionsYield
Stage #1: 4-Chlorobutyronitrile; ethyl bromoacetate With methanesulfonic acid; zinc In tetrahydrofuran for 1h; Blaise reaction; Reflux; Inert atmosphere;
Stage #2: With potassium tert-butylate In tetrahydrofuran at 0 - 20℃; for 5h; Blaise reaction; Inert atmosphere; chemoselective reaction;
A 13%
B 68%
Stage #1: 4-Chlorobutyronitrile; ethyl bromoacetate With methanesulfonic acid; zinc In tetrahydrofuran for 1h; Blaise reaction; Reflux; Inert atmosphere;
Stage #2: With sodium hexamethyldisilazane In tetrahydrofuran at 0℃; Blaise reaction; Inert atmosphere; Reflux; chemoselective reaction;
A 17%
B 12%
ethyl bromoacetate
105-36-2

ethyl bromoacetate

4-bromobutanenitrile
5332-06-9

4-bromobutanenitrile

ethyl 2-amino-1-cyclopentene-1-carboxylate
7149-18-0

ethyl 2-amino-1-cyclopentene-1-carboxylate

Conditions
ConditionsYield
With methanesulfonic acid; zinc In tetrahydrofuran for 8h; Blaise reaction; Reflux; Inert atmosphere; chemoselective reaction;40%
4-Chlorobutyronitrile
628-20-6

4-Chlorobutyronitrile

ethyl bromoacetate
105-36-2

ethyl bromoacetate

A

ethyl 2-amino-1-cyclopentene-1-carboxylate
7149-18-0

ethyl 2-amino-1-cyclopentene-1-carboxylate

B

pyrrolidin-2-ylideneacetic acid ethyl ester
25219-53-8, 35150-22-2, 108139-96-4

pyrrolidin-2-ylideneacetic acid ethyl ester

Conditions
ConditionsYield
With methanesulfonic acid; zinc In tetrahydrofuran for 15h; Blaise reaction; Reflux; Inert atmosphere; chemoselective reaction;A 29%
B 6%
With methanesulfonic acid; zinc In tetrahydrofuran Inert atmosphere; Reflux;A 29%
B 6%
diethyl adipate
141-28-6

diethyl adipate

ethyl 2-amino-1-cyclopentene-1-carboxylate
7149-18-0

ethyl 2-amino-1-cyclopentene-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Reaktion ueber mehrere Stufen
2: concentrated alcoholic ammonia / 140 - 150 °C
View Scheme
ethyl 2-[(ethoxycarbonyl)amino]-1-cyclopentene-1-carboxylate
20873-66-9

ethyl 2-[(ethoxycarbonyl)amino]-1-cyclopentene-1-carboxylate

ethyl 2-amino-1-cyclopentene-1-carboxylate
7149-18-0

ethyl 2-amino-1-cyclopentene-1-carboxylate

Conditions
ConditionsYield
With sodium methylate In methanol
ethyl 2-amino-1-cyclopentene-1-carboxylate
7149-18-0

ethyl 2-amino-1-cyclopentene-1-carboxylate

p-Tolylisocyanate
622-58-2

p-Tolylisocyanate

2-(3-p-Tolyl-ureido)-cyclopent-1-enecarboxylic acid ethyl ester

2-(3-p-Tolyl-ureido)-cyclopent-1-enecarboxylic acid ethyl ester

Conditions
ConditionsYield
In toluene Heating;83%
ethyl 2-amino-1-cyclopentene-1-carboxylate
7149-18-0

ethyl 2-amino-1-cyclopentene-1-carboxylate

m-chlorophenyl isocyanate
2909-38-8

m-chlorophenyl isocyanate

2-[3-(3-Chloro-phenyl)-ureido]-cyclopent-1-enecarboxylic acid ethyl ester

2-[3-(3-Chloro-phenyl)-ureido]-cyclopent-1-enecarboxylic acid ethyl ester

Conditions
ConditionsYield
In toluene Heating;78%
ethyl 2-amino-1-cyclopentene-1-carboxylate
7149-18-0

ethyl 2-amino-1-cyclopentene-1-carboxylate

ethyl 2-isothiocyanatoacetate
24066-82-8

ethyl 2-isothiocyanatoacetate

ethyl 2-[3-ethoxycarbonylmethylthioureido]cyclopentene-1-carboxylate

ethyl 2-[3-ethoxycarbonylmethylthioureido]cyclopentene-1-carboxylate

Conditions
ConditionsYield
With pyridine for 2h; Heating;76%
ethyl 2-amino-1-cyclopentene-1-carboxylate
7149-18-0

ethyl 2-amino-1-cyclopentene-1-carboxylate

3-tolyl isocyanate
621-29-4

3-tolyl isocyanate

2-(3-m-Tolyl-ureido)-cyclopent-1-enecarboxylic acid ethyl ester

2-(3-m-Tolyl-ureido)-cyclopent-1-enecarboxylic acid ethyl ester

Conditions
ConditionsYield
In toluene Heating;66%
ethyl 2-amino-1-cyclopentene-1-carboxylate
7149-18-0

ethyl 2-amino-1-cyclopentene-1-carboxylate

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

2-[3-(4-Chloro-phenyl)-ureido]-cyclopent-1-enecarboxylic acid ethyl ester

2-[3-(4-Chloro-phenyl)-ureido]-cyclopent-1-enecarboxylic acid ethyl ester

Conditions
ConditionsYield
In toluene Heating;63%
2-methylsulfanyl-4,5-dihydrothiazoline
19975-56-5

2-methylsulfanyl-4,5-dihydrothiazoline

ethyl 2-amino-1-cyclopentene-1-carboxylate
7149-18-0

ethyl 2-amino-1-cyclopentene-1-carboxylate

2,3,7,8-tetrahydro-5H,6H-cyclopenta[1,2-d]thiazolo[3,2-a]pyrimidin-5-one

2,3,7,8-tetrahydro-5H,6H-cyclopenta[1,2-d]thiazolo[3,2-a]pyrimidin-5-one

Conditions
ConditionsYield
With acetic acid for 24h; Heating;60%
ethyl 2-amino-1-cyclopentene-1-carboxylate
7149-18-0

ethyl 2-amino-1-cyclopentene-1-carboxylate

Glycine ethyl ester isocyanate
2949-22-6

Glycine ethyl ester isocyanate

ethyl 2-[3-ethoxycarbonylmethylureido]cyclopentene-1-carboxylate

ethyl 2-[3-ethoxycarbonylmethylureido]cyclopentene-1-carboxylate

Conditions
ConditionsYield
With pyridine for 2h; Heating;58%
2-(methylthio)-1,4,5,6-tetrahydropyrimidine
20112-81-6

2-(methylthio)-1,4,5,6-tetrahydropyrimidine

ethyl 2-amino-1-cyclopentene-1-carboxylate
7149-18-0

ethyl 2-amino-1-cyclopentene-1-carboxylate

2,3,4,7,8,9-hexahydro-1H,6H-cyclopenta[1,2-d]pyrimido[1,2-a]pyrimidin-6-one

2,3,4,7,8,9-hexahydro-1H,6H-cyclopenta[1,2-d]pyrimido[1,2-a]pyrimidin-6-one

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide at 160℃; for 10h;57%
5,6-dihydro-2-(methylthio)-4H-1,3-thiazine
58842-19-6

5,6-dihydro-2-(methylthio)-4H-1,3-thiazine

ethyl 2-amino-1-cyclopentene-1-carboxylate
7149-18-0

ethyl 2-amino-1-cyclopentene-1-carboxylate

2,3,4,7,8,9-hexahydro-6H-cyclopenta[4',3':4,5]pyrimido[2,1-b][1,3]thiazin-6-one

2,3,4,7,8,9-hexahydro-6H-cyclopenta[4',3':4,5]pyrimido[2,1-b][1,3]thiazin-6-one

Conditions
ConditionsYield
With acetic acid for 24h; Heating;56%
5-fluorothiophene-2-carbonitrile
32415-91-1

5-fluorothiophene-2-carbonitrile

ethyl 2-amino-1-cyclopentene-1-carboxylate
7149-18-0

ethyl 2-amino-1-cyclopentene-1-carboxylate

2-(5-fluorothiophen-2-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-ol

2-(5-fluorothiophen-2-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-ol

Conditions
ConditionsYield
With potassium tert-butylate In 1,3,5-trimethyl-benzene at 150℃; for 4h;55%
2-methylthioimidazoline
20112-79-2

2-methylthioimidazoline

ethyl 2-amino-1-cyclopentene-1-carboxylate
7149-18-0

ethyl 2-amino-1-cyclopentene-1-carboxylate

1,2,3,6,7,8-hexahydro-5H-cyclopenta[1,2-d]imidazo[1,2-a]pyrimidin-5-one

1,2,3,6,7,8-hexahydro-5H-cyclopenta[1,2-d]imidazo[1,2-a]pyrimidin-5-one

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide at 160℃; for 12h;52%
ethyl 2-amino-1-cyclopentene-1-carboxylate
7149-18-0

ethyl 2-amino-1-cyclopentene-1-carboxylate

2-tolyl isocyanate
614-68-6

2-tolyl isocyanate

2-(3-o-Tolyl-ureido)-cyclopent-1-enecarboxylic acid ethyl ester

2-(3-o-Tolyl-ureido)-cyclopent-1-enecarboxylic acid ethyl ester

Conditions
ConditionsYield
In toluene Heating;50%
ethyl 2-amino-1-cyclopentene-1-carboxylate
7149-18-0

ethyl 2-amino-1-cyclopentene-1-carboxylate

phenyl isocyanate
103-71-9

phenyl isocyanate

N-(2-Carbethoxycyclopentenyl)-N'-phenylharnstoff
49786-25-6

N-(2-Carbethoxycyclopentenyl)-N'-phenylharnstoff

Conditions
ConditionsYield
In toluene Heating;45%
ethyl 2-amino-1-cyclopentene-1-carboxylate
7149-18-0

ethyl 2-amino-1-cyclopentene-1-carboxylate

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

ethyl 2-((4-methylphenyl)sulfonamido)cyclopent-1-ene-1-carboxylate

ethyl 2-((4-methylphenyl)sulfonamido)cyclopent-1-ene-1-carboxylate

Conditions
ConditionsYield
With pyridine In dichloromethane at 25℃; for 12h;32%
With pyridine In dichloromethane at 20℃;30%
ethyl 2-amino-1-cyclopentene-1-carboxylate
7149-18-0

ethyl 2-amino-1-cyclopentene-1-carboxylate

acetic anhydride
108-24-7

acetic anhydride

2-acetylaminocyclopent-1-enecarboxylic acid ethyl ester
29942-18-5

2-acetylaminocyclopent-1-enecarboxylic acid ethyl ester

ethyl 2-amino-1-cyclopentene-1-carboxylate
7149-18-0

ethyl 2-amino-1-cyclopentene-1-carboxylate

phenyl isocyanate
103-71-9

phenyl isocyanate

3-phenyl-1,5,6,7-tetrahydro-cyclopentapyrimidine-2,4-dione
5313-47-3

3-phenyl-1,5,6,7-tetrahydro-cyclopentapyrimidine-2,4-dione

Conditions
ConditionsYield
With pyridine; xylene
ethyl 2-amino-1-cyclopentene-1-carboxylate
7149-18-0

ethyl 2-amino-1-cyclopentene-1-carboxylate

methyl thioisocyanate
556-61-6

methyl thioisocyanate

3-methyl-2-thioxo-2,3,6,7-tetrahydro-1H-cyclopenta[d]pyrimidin-4(5H)-one
108989-50-0

3-methyl-2-thioxo-2,3,6,7-tetrahydro-1H-cyclopenta[d]pyrimidin-4(5H)-one

Conditions
ConditionsYield
With pyridine; xylene
ethyl 2-amino-1-cyclopentene-1-carboxylate
7149-18-0

ethyl 2-amino-1-cyclopentene-1-carboxylate

diethyl malonate
105-53-3

diethyl malonate

2,4-dihydroxy-6,7-dihydro-5H-[1]pyrindine-3-carboxylic acid ethyl ester
55618-82-1

2,4-dihydroxy-6,7-dihydro-5H-[1]pyrindine-3-carboxylic acid ethyl ester

Conditions
ConditionsYield
With ethanol; sodium ethanolate at 110℃;
ethyl 2-amino-1-cyclopentene-1-carboxylate
7149-18-0

ethyl 2-amino-1-cyclopentene-1-carboxylate

Di-(2-carboxycyclopentyl)amin
104743-69-3

Di-(2-carboxycyclopentyl)amin

Conditions
ConditionsYield
With hydrogen; platinum(IV) oxide In acetic acid
ethyl 2-amino-1-cyclopentene-1-carboxylate
7149-18-0

ethyl 2-amino-1-cyclopentene-1-carboxylate

sodium ethanolate
141-52-6

sodium ethanolate

diethyl malonate
105-53-3

diethyl malonate

2.4-dihydroxy-6.7-dihydro-5H-<1>pyrindine-carboxylic acid-(3)-ethyl ester

2.4-dihydroxy-6.7-dihydro-5H-<1>pyrindine-carboxylic acid-(3)-ethyl ester

Conditions
ConditionsYield
at 110℃;
ethyl 2-amino-1-cyclopentene-1-carboxylate
7149-18-0

ethyl 2-amino-1-cyclopentene-1-carboxylate

cis-2-acetylaminocyclopentanecarboxylic acid ethyl ester

cis-2-acetylaminocyclopentanecarboxylic acid ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine / tetrahydrofuran / Heating
2: H2; HBF4; (S)-[2,2'-bis(PPh2)-6,6'-(1,3-propylidenedioxy)]biphenyl / Ru(COD)(methallyl)2 / ethanol / 18 h / 20 °C / 38000 Torr
View Scheme
Multi-step reaction with 2 steps
1: toluene / 2 h / 75 °C / Inert atmosphere
2: [bis(2-methylallyl)cycloocta-1,5-diene]ruthenium(II); (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); tetrafluoroboric acid dimethyl ether complex; hydrogen / methanol / 0 - 50 °C / 3878.71 Torr / Inert atmosphere
View Scheme
ethyl 2-amino-1-cyclopentene-1-carboxylate
7149-18-0

ethyl 2-amino-1-cyclopentene-1-carboxylate

3-ethoxycarbonylmethyl-2,4-dioxo-1,3,4,5,6,7-hexahydro-2H-cyclopenta[1,2-d]pyrimidine

3-ethoxycarbonylmethyl-2,4-dioxo-1,3,4,5,6,7-hexahydro-2H-cyclopenta[1,2-d]pyrimidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 58 percent / pyridine / 2 h / Heating
2: 68 percent / NaOEt / ethanol / 1 h / 20 °C
View Scheme
ethyl 2-amino-1-cyclopentene-1-carboxylate
7149-18-0

ethyl 2-amino-1-cyclopentene-1-carboxylate

3-ethoxycarbonylmethyl-4-oxo-2-thioxo-1,3,4,5,6,7-hexahydro-2H-cyclopenta[1,2-d]pyrimidine

3-ethoxycarbonylmethyl-4-oxo-2-thioxo-1,3,4,5,6,7-hexahydro-2H-cyclopenta[1,2-d]pyrimidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 76 percent / pyridine / 2 h / Heating
2: 73 percent / NaOEt / ethanol / 1 h / 20 °C
View Scheme
ethyl 2-amino-1-cyclopentene-1-carboxylate
7149-18-0

ethyl 2-amino-1-cyclopentene-1-carboxylate

3-phenyl-1,5,6,7-tetrahydro-cyclopentapyrimidine-2,4-dione
5313-47-3

3-phenyl-1,5,6,7-tetrahydro-cyclopentapyrimidine-2,4-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 45 percent / toluene / Heating
2: 61 percent / aq. NaOH / Heating
View Scheme
ethyl 2-amino-1-cyclopentene-1-carboxylate
7149-18-0

ethyl 2-amino-1-cyclopentene-1-carboxylate

3-p-Tolyl-1,5,6,7-tetrahydro-cyclopentapyrimidine-2,4-dione

3-p-Tolyl-1,5,6,7-tetrahydro-cyclopentapyrimidine-2,4-dione

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 83 percent / toluene / Heating
2: 70 percent / aq. NaOH / Heating
View Scheme

7149-18-0Relevant articles and documents

Iridium complex-linked porous organic polymers for recyclable, broad-scope photocatalysis of organic transformations

Xu, Zi-Yue,Luo, Yi,Zhang, Dan-Wei,Wang, Hui,Sun, Xing-Wen,Li, Zhan-Ting

supporting information, p. 136 - 143 (2020/01/21)

Two rigid porous organic polymers (Ir-POP-1 and Ir-POP-2) were prepared from the coupling reactions of tetraphenylmethane tetraborate and two [Ir(ppy)2(dtbbpy)]+-based bitopic linkers and applied as heterogeneous visible-light photocatalysts for organic transformations. Ir-POP-2 was found to exhibit high catalytic activity for a wide range of organic reactions, which include Smiles-Truce rearrangement of alkyliodides, desulfurative conjugate addition to Michael acceptors, and aerobic oxidations of sulfides and arylboronic acids. For all the transformations, Ir-POP-2 could achieve heterogeneous photocatalytic efficiency that rivals that of the homogeneous prototype iridium complexes. This remarkably high photocatalytic performance has been attributed to the large pore size of the conjugated backbone. The new heterogeneous photocatalyst was also highly stable to achieve good recyclability for all the studied reactions and could be reused eight to nineteen times.

Chemoselective intramolecular alkylation of the Blaise reaction intermediates: Tandem one-pot synthesis of exo -cyclic enaminoesters and their applications toward the synthesis of N -heterocyclic compounds

Kim, Ju Hyun,Shin, Hyunik,Lee, Sang-Gi

experimental part, p. 1560 - 1565 (2012/04/04)

The intramolecular alkylative reactivity and N/C selectivity of the various Blaise reaction intermediates, which are formed from the reaction of the Reformatsky reagents with ω-chloroalkyl nitriles, did not reach the synthetic potential as an entry to exo-cyclic enaminoesters. To circumvent this issue, various additives were investigated, among which the addition of NaHMDS dramatically enhanced the reactivity and N/C selectivity. This modification provided a highly efficient route for the synthesis of various N-fused heterocyclic compounds, as it requires only two steps from nitriles.

Development of a suitable process for the preparation of a TNF-α converting enzyme inhibitor, WAY-281418

Wang, Youchu,Papamichelakis, Maria,Chew, Warren,Sellstedt, John,Noureldin, Razzak,Tadayon, Sam,Daigneault, Sylvain,Galante, Rocco J.,Sun, Jerry

, p. 1253 - 1260 (2013/01/03)

A suitable process for the preparation of kilogram quantities of a TNF-α converting enzyme (TACE) inhibitor (WAY-281418) was developed using isatin 13 as starting material and an efficient coupling step for the formation of sulfonamide 8 in a 15% overall yield. Process preparation of (+)-(1S,2R)-2-aminocyclopentane-1-carboxylic acid (7, (+)-cispentacin), a chiral component for WAY-281418, was successfully scaled up via an asymmetric hydroge-nation reaction. Crystallization allowed the isolation of all intermediates and the final product 9.

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