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1,1-Cyclohexanediacetic acid mono amide
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Name

1,1-Cyclohexanediacetic acid mono amide

 EINECS 449-430-4
CAS No. 99189-60-3 Density 1.135 g/cm3
PSA 80.39000 LogP 1.98730
Solubility N/A Melting Point 143-146 °C
Formula C10H17NO3 Boiling Point 443.6 °C at760mmHg
Molecular Weight 199.25 Flash Point 222.1 °C
Transport Information N/A Appearance White powder
Safety 22-24/25 Risk Codes 61
Molecular Structure Molecular Structure of 99189-60-3 (1,1-Cyclohexanediacetic acid mono amide) Hazard Symbols T
Synonyms

Cyclohexaneaceticacid, 1-(carbamoylmethyl)- (6CI);1,1-Cyclohexanediacetic acid monoamide;1-(Carboxymethyl)cyclohexane-1-acetamide;1-[(Aminocarbonyl)methyl]cyclohexaneacetic acid;

Article Data 11

1,1-Cyclohexanediacetic acid mono amide Synthetic route

1130-32-1

3-azaspiro[5,5]undecane-2,4-dione

99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

Conditions
ConditionsYield
With water; sodium hydroxide at 50℃; for 6h; Reagent/catalyst;93%
With sodium hydroxide
Stage #1: 3-azaspiro[5.5]undecane-2,4-dione With sodium hydroxide; water at 95 - 105℃; for 6h; Heating / reflux;
Stage #2: With hydrogenchloride In water; isopropyl alcohol at 20 - 40℃; for 1h; pH=6.5; Industry scale;
Stage #3: With hydrogenchloride In water; isopropyl alcohol at 35 - 40℃; for 1h; pH=4.0 - 4.5; Industry scale;
Stage #1: 3-azaspiro[5.5]undecane-2,4-dione With sodium hydroxide; water for 1h; Heating / reflux;
Stage #2: With hydrogenchloride In water at 25℃; pH=5;
90961-78-7

spiro[cyclohexane-1,9’-(3,7-diazabicycle-[3.3.1]nonane)]-2’,4’,6’,8’-tetraone

99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

Conditions
ConditionsYield
With water; sodium hydroxide at 100 - 105℃; for 18h;80.8%
1010-26-0

1,1-cyclohexanediacetic acid anhydride

99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

Conditions
ConditionsYield
Stage #1: 1,1-cyclohexanediacetic acid anhydride With ammonia In water; acetic acid; toluene at 10 - 30℃; for 1.33333h; pH=> 8;
Stage #2: With hydrogenchloride In water at 40 - 45℃; for 0.333333h; pH=3.8 - 4.2;
Stage #1: 1,1-cyclohexanediacetic acid anhydride With sodium hydroxide; water; ammonium chloride at 0 - 30℃; for 4h;
Stage #2: With hydrogenchloride; water pH=2 - 3; Product distribution / selectivity;
Stage #1: 1,1-cyclohexanediacetic acid anhydride With ammonia; water In isopropyl alcohol at 5℃; for 1h;
Stage #2: With hydrogenchloride; water In isopropyl alcohol at 15 - 20℃; for 15h; pH=2 - 3; Product distribution / selectivity;
4355-11-7

1,1-cyclohexanediacetic acid

99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: acetic anhydride / 2 h / 130 °C
2.1: ammonia / benzene / 5 h / 25 - 105 °C
2.2: 1.5 h / 55 °C / pH 4
View Scheme
Multi-step reaction with 2 steps
1: acetic anhydride / 0.5 h / 110 °C
2: ammonium hydroxide / 1 h
View Scheme
99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

64744-50-9

gabapentin-lactam

Conditions
ConditionsYield
Stage #1: [1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid With sodium hydroxide; sodium hypochlorite In water at 0 - 40℃; for 3.5h;
Stage #2: With hydrogenchloride In water at 100 - 105℃; for 3h; pH=8.2 - 8.8; Product distribution / selectivity; Heating / reflux;		100%
Stage #1: [1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid With sodium hydroxide; sodium hypochlorite In water at 0 - 50℃; for 3h;
Stage #2: With hydrogenchloride In water at 100 - 105℃; for 3h; pH=11 - 12; Product distribution / selectivity;		93.8%
Stage #1: [1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid With sodium hydroxide In water at 20 - 30℃; for 0.5h;
Stage #2: With sode de l'acide trichloroisocyanurique In water at 0 - 20℃; for 5h;
Stage #3: In water; toluene at 80℃; for 8h; Reagent/catalyst;		85%
Multi-step reaction with 2 steps
1.1: trichloroisocyanuric acid / methanol / 1.75 h / 20 - 25 °C
2.1: sodium hydroxide / water / 4 h / 0 - 20 °C
2.2: 8 h / 80 °C
View Scheme
99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

C10H16ClNO3

Conditions
ConditionsYield
With trichloroisocyanuric acid In methanol at 20 - 25℃; for 1.75h;100%
99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

63562-00-5

1-(aminomethyl)-1-cyclohexaneacetic acid sodium salt

Conditions
ConditionsYield
With sodium hypobromide; sodium hydroxide In water at 40 - 55℃; Reagent/catalyst; Temperature; Hofmann Rearrangement; Flow reactor;91.98%
With sodium hydroxide; sodium hypobromide In water at 0 - 10℃; for 2 - 3h; Product distribution / selectivity; Hofmann Rearrangement;67%
With sodium hydroxide; sodium hypochlorite In water at 0 - 10℃; for 2 - 3h; Product distribution / selectivity; Hofmann Rearrangement;65%
99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

1-(aminomethyl)cyclohexaneacetic acid hydrochloride

Conditions
ConditionsYield
Stage #1: [1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid With sodium hydroxide; sodium hypochlorite In water at -5 - 25℃; for 9h;
Stage #2: With hydrogenchloride In water; butan-1-ol pH=1.5;		75%
Stage #1: [1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid With sodium hydroxide; bromine In water at -8 - 40℃; for 2h;
Stage #2: With hydrogenchloride; water for 4h; pH=2;
Multi-step reaction with 2 steps
1.1: sodium hydroxide / water / 0.5 h / 20 - 30 °C
1.2: 5 h / 0 - 20 °C
1.3: 8 h / 80 °C
2.1: hydrogenchloride; water / 10 h / 100 °C
View Scheme
Multi-step reaction with 3 steps
1.1: trichloroisocyanuric acid / methanol / 1.75 h / 20 - 25 °C
2.1: sodium hydroxide / water / 4 h / 0 - 20 °C
2.2: 8 h / 80 °C
3.1: hydrogenchloride; water / 10 h / 100 °C
View Scheme
Stage #1: [1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid With sodium hypochlorite; sodium hydroxide In water; benzene at 100℃;
Stage #2: at 95℃; for 3h; Temperature;
99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

gabapentin hemisulphate

Conditions
ConditionsYield
Stage #1: [1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid With sodium hydroxide; sodium hypochlorite In water at -5 - 25℃; for 9h;
Stage #2: With sulfuric acid In water; butan-1-ol pH=1.5;		73.8%
99189-60-3

[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid

60142-96-3

H-Gpn-OH

Conditions
ConditionsYield
With sodium carbonate In benzyl alcohol pH=7 - 7.5; Product distribution / selectivity;68.6%
With sodium hydroxide; sodium hypochlorite In water at -10 - 20℃; for 8h; Hofmann Rearrangement;
Stage #1: [1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid With sodium hypochlorite; sodium hydroxide In water at 40℃; Hofmann Rearrangement;
Stage #2: With sodium metabisulfite In water Product distribution / selectivity;

1,1-Cyclohexanediacetic acid mono amide Chemical Properties

Empirical Formula: C10H17NO3
Molecular Weight: 199.2469 g/mol
EINECS: 449-430-4 
Index of Refraction: 1.497
Density: 1.135 g/cm3
Flash Point: 222.1 °C
Melting point: 141-146 °C(lit.)
Appearance: White powder
Enthalpy of Vaporization: 76.88 kJ/mol
Boiling Point: 443.6 °C at 760 mmHg
Vapour Pressure: 4.14E-09 mmHg at 25 °C
Structure of 1,1-Cyclohexanediacetic acid mono amide (CAS NO.99189-60-3):
                            
Product Category of 1,1-Cyclohexanediacetic acid mono amide (CAS NO.99189-60-3): Organic acids

1,1-Cyclohexanediacetic acid mono amide Safety Profile

Safety Description of 1,1-Cyclohexanediacetic acid mono amide (CAS NO.99189-60-3): S24/25
 S24/25:Avoid contact with skin and eyes.

1,1-Cyclohexanediacetic acid mono amide Specification

 1,1-Cyclohexanediacetic acid mono amide , its cas register number is 99189-60-3. It also can be called 3,3-Pentamethyleneglutaramic acid .

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