Product Name

  • Name

    tert-Butyl glycinate

  • EINECS 1533716-785-6
  • CAS No. 6456-74-2
  • Article Data47
  • CAS DataBase
  • Density 0.973 g/cm3
  • Solubility Miscible with acetone and methanol. Slightly miscible with ehtanol. Immiscible with water.
  • Melting Point 148-150 °C (decomp)
  • Formula C6H13NO2
  • Boiling Point 145.7 °C at 760 mmHg
  • Molecular Weight 131.175
  • Flash Point 20.7 °C
  • Transport Information
  • Appearance White crystalline powder/Colorless Clear Liquid
  • Safety 26-36/37/39
  • Risk Codes 36/38
  • Molecular Structure Molecular Structure of 6456-74-2 (tert-Butyl glycinate)
  • Hazard Symbols R36/38:Irritating to eyes and skin.;
  • Synonyms Glycine,tert-butyl ester (6CI,7CI,8CI);1,1-Dimethylethyl glycinate;Aminoacetic acidtert-butyl ester;Aminoacetic acid tert-butyl ester;[(tert-Butoxycarbonyl)methyl]amine;tert-Butyl 2-aminoacetate;tert-Butylaminoacetate;tert-Butyl glycinate;
  • PSA 52.32000
  • LogP 0.98710

Synthetic route

tert-butyl N-(benzyloxycarbonyl)glycinate
16881-32-6

tert-butyl N-(benzyloxycarbonyl)glycinate

Glycine tert-butyl ester
6456-74-2

Glycine tert-butyl ester

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In ethanol92%
With hydrogen; palladium on activated charcoal In ethanol
With hydrogen; palladium on activated charcoal In methanol
bromoacetic acid tert-butyl ester
5292-43-3

bromoacetic acid tert-butyl ester

Glycine tert-butyl ester
6456-74-2

Glycine tert-butyl ester

Conditions
ConditionsYield
With ammonia In diethyl ether 1.) -40 deg C, 2 h, 2.) RT, overnight;90%
With ammonia In diethyl ether at -40℃;87%
With ammonia at -78℃; for 48h; Inert atmosphere;72%
With ammonia In diethyl ether at -40℃;70%
Multi-step reaction with 2 steps
1: aq. NaN3 / acetone
2: H2 / Pd-C / methanol
View Scheme
N-(9-fluorenylmethoxycarbonyl)glycine tert-butyl ester
35661-42-8

N-(9-fluorenylmethoxycarbonyl)glycine tert-butyl ester

Glycine tert-butyl ester
6456-74-2

Glycine tert-butyl ester

Conditions
ConditionsYield
With triethylamine; 1-butyl-3-methylimidazolium Tetrafluoroborate In neat (no solvent) at 25℃; Green chemistry;82%
(2,2,2-trichloro-ethoxycarbonylamino)-acetic acid tert-butyl ester
819050-60-7

(2,2,2-trichloro-ethoxycarbonylamino)-acetic acid tert-butyl ester

Glycine tert-butyl ester
6456-74-2

Glycine tert-butyl ester

Conditions
ConditionsYield
With 1-methyl-1H-imidazole; zinc In ethyl acetate for 6h;57%
tert-butyl methyl ether
1634-04-4

tert-butyl methyl ether

glycine
56-40-6

glycine

Glycine tert-butyl ester
6456-74-2

Glycine tert-butyl ester

Conditions
ConditionsYield
With sulfuric acid at 25℃; for 2h; Molecular sieve; chemoselective reaction;51%
Fms-Gly-OtBu
1245735-65-2

Fms-Gly-OtBu

Glycine tert-butyl ester
6456-74-2

Glycine tert-butyl ester

Conditions
ConditionsYield
With piperidine In N,N-dimethyl-formamide at 25℃; for 0.166667h;
N-(diphenylmethylene)glycine tert-butyl ester
81477-94-3

N-(diphenylmethylene)glycine tert-butyl ester

A

benzophenone
119-61-9

benzophenone

B

Glycine tert-butyl ester
6456-74-2

Glycine tert-butyl ester

Conditions
ConditionsYield
With cesiumhydroxide monohydrate In dichloromethane; toluene
N-(diphenylmethylene)glycine tert-butyl ester
81477-94-3

N-(diphenylmethylene)glycine tert-butyl ester

Glycine tert-butyl ester
6456-74-2

Glycine tert-butyl ester

Conditions
ConditionsYield
With cycl-isopropylidene malonate; water In ethyl acetate at 20℃; for 8h;
Glycine tert-butyl ester
6456-74-2

Glycine tert-butyl ester

benzaldehyde
100-52-7

benzaldehyde

tert-butyl N-benzylideneglycinate
64923-12-2

tert-butyl N-benzylideneglycinate

Conditions
ConditionsYield
With sodium sulfate In benzene Ambient temperature;100%
With trimethyl orthoformate for 8h;96%
With magnesium sulfate In benzene for 0.5h; Ambient temperature;75%
With magnesium sulfate In benzene
Stage #1: Glycine tert-butyl ester With magnesium sulfate; triethylamine In dichloromethane at 20℃; for 1h;
Stage #2: benzaldehyde In dichloromethane at 20℃;
Glycine tert-butyl ester
6456-74-2

Glycine tert-butyl ester

Z-Gly-L-Azy-Gly-OBzl
72087-11-7

Z-Gly-L-Azy-Gly-OBzl

A

N-carbobenzyloxy-glycyl-glycine tert-butyl ester
27375-61-7

N-carbobenzyloxy-glycyl-glycine tert-butyl ester

B

(2S)-H-Azy-Gly-OBzl
76314-24-4

(2S)-H-Azy-Gly-OBzl

Conditions
ConditionsYield
In dichloromethane for 24h; Ambient temperature;A 84.8%
B 100%
...Expand
Glycine tert-butyl ester
6456-74-2

Glycine tert-butyl ester

2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methyl-thiobutyric acid S-(2-formyl-4-nitro-phenyl) ester
557095-50-8

2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methyl-thiobutyric acid S-(2-formyl-4-nitro-phenyl) ester

Fmoc-Val-Gly-OtBu

Fmoc-Val-Gly-OtBu

Conditions
ConditionsYield
With N-methylmaleimide In phosphate buffer; N,N-dimethyl-formamide at 20℃; for 2.5h; pH=8.0;100%
Glycine tert-butyl ester
6456-74-2

Glycine tert-butyl ester

4-trifluorophenylsulfonyl chloride
2991-42-6

4-trifluorophenylsulfonyl chloride

tert-Butyl 2-(4-(trifluoromethyl)phenylsulfonamido)acetate
959997-92-3

tert-Butyl 2-(4-(trifluoromethyl)phenylsulfonamido)acetate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 18h;100%
4,4-dimethylpentanal
926-36-3

4,4-dimethylpentanal

Glycine tert-butyl ester
6456-74-2

Glycine tert-butyl ester

2-[(E)-(3,3-dimethylbutylidene)amino]acetic acid tert-butyl ester
1219086-34-6

2-[(E)-(3,3-dimethylbutylidene)amino]acetic acid tert-butyl ester

Conditions
ConditionsYield
In dichloromethane at 20℃;100%
In dichloromethane at 20℃;
3,3-dimethylbutyrylaldehyde
2987-16-8

3,3-dimethylbutyrylaldehyde

Glycine tert-butyl ester
6456-74-2

Glycine tert-butyl ester

2-[(E)-(3,3-dimethylbutylidene)amino]acetic acid tert-butyl ester
1219086-34-6

2-[(E)-(3,3-dimethylbutylidene)amino]acetic acid tert-butyl ester

Conditions
ConditionsYield
In dichloromethane at 20℃;100%
In dichloromethane at 20℃;100%
In dichloromethane at 20℃;100%
Glycine tert-butyl ester
6456-74-2

Glycine tert-butyl ester

(N-benzyloxycarbonyl)-L-alanine N-hydroxysuccinimide ester
3401-36-3

(N-benzyloxycarbonyl)-L-alanine N-hydroxysuccinimide ester

tert-butyl ((benzyloxy)carbonyl)-L-alanylglycinate
13512-48-6

tert-butyl ((benzyloxy)carbonyl)-L-alanylglycinate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h; Inert atmosphere;100%
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h; Inert atmosphere;
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h; Inert atmosphere;
1-chloro-4-methoxyisoquinoline-3-carboxylic acid
914672-45-0

1-chloro-4-methoxyisoquinoline-3-carboxylic acid

Glycine tert-butyl ester
6456-74-2

Glycine tert-butyl ester

tert-butyl 2-(1-chloro-4-methoxyisoquinoline-3-carboxamido)acetate

tert-butyl 2-(1-chloro-4-methoxyisoquinoline-3-carboxamido)acetate

Conditions
ConditionsYield
Stage #1: 1-chloro-4-methoxyisoquinoline-3-carboxylic acid With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.166667h;
Stage #2: Glycine tert-butyl ester In N,N-dimethyl-formamide at 20℃; for 0.333333h;
Stage #3: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 16h; Inert atmosphere;		100%
Glycine tert-butyl ester
6456-74-2

Glycine tert-butyl ester

C46H51N5O10

C46H51N5O10

C52H62N6O11

C52H62N6O11

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at -5 - 20℃; Temperature;100%
Glycine tert-butyl ester
6456-74-2

Glycine tert-butyl ester

C69H75N5O18

C69H75N5O18

C75H86N6O19

C75H86N6O19

Conditions
ConditionsYield
Stage #1: Glycine tert-butyl ester; C69H75N5O18 With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate at 0℃; for 0.333333h;
Stage #2: With N-ethyl-N,N-diisopropylamine at 0℃;		100%
Glycine tert-butyl ester
6456-74-2

Glycine tert-butyl ester

C68H73N5O18

C68H73N5O18

C74H84N6O19

C74H84N6O19

Conditions
ConditionsYield
Stage #1: Glycine tert-butyl ester; C68H73N5O18 With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate In N,N-dimethyl-formamide at 0℃; for 0.5h;
Stage #2: With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide		100%
Glycine tert-butyl ester
6456-74-2

Glycine tert-butyl ester

(2'S,5R)-1-(1'-oxo-2'-phenylmethylpropyl)-3,3,5-trimethylpyrrolidin-2-one
155956-28-8

(2'S,5R)-1-(1'-oxo-2'-phenylmethylpropyl)-3,3,5-trimethylpyrrolidin-2-one

(2S)-N-tert-butoxycarbonylmethyl-2-phenylmethylpropanamide

(2S)-N-tert-butoxycarbonylmethyl-2-phenylmethylpropanamide

Conditions
ConditionsYield
for 120h;99%
at 20℃; for 120h;99%
Glycine tert-butyl ester
6456-74-2

Glycine tert-butyl ester

2,2,2-Trichloroethyl chloroformate
17341-93-4

2,2,2-Trichloroethyl chloroformate

(2,2,2-trichloro-ethoxycarbonylamino)-acetic acid tert-butyl ester
819050-60-7

(2,2,2-trichloro-ethoxycarbonylamino)-acetic acid tert-butyl ester

Conditions
ConditionsYield
With pyridine In tetrahydrofuran at 0 - 20℃;99%
BTZO-2
501375-54-8

BTZO-2

Glycine tert-butyl ester
6456-74-2

Glycine tert-butyl ester

tert-butyl ({3-[6-(4-Oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]propanoyl }amino)acetate

tert-butyl ({3-[6-(4-Oxo-4H-1,3-benzothiazin-2-yl)-2-pyridyl]propanoyl }amino)acetate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 17h;99%
Glycine tert-butyl ester
6456-74-2

Glycine tert-butyl ester

benzyl chloroformate
501-53-1

benzyl chloroformate

benzyloxycarbonyl-amino acetic acid tert-butyl ester

benzyloxycarbonyl-amino acetic acid tert-butyl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 3h;99%
2,2-dimethyl-4-oxobutyronitrile
18240-73-8

2,2-dimethyl-4-oxobutyronitrile

Glycine tert-butyl ester
6456-74-2

Glycine tert-butyl ester

tert-butyl (E)-2-(3-cyano-3-methylbutylideneamino)acetate

tert-butyl (E)-2-(3-cyano-3-methylbutylideneamino)acetate

Conditions
ConditionsYield
In dichloromethane at 20℃;98.8%
Glycine tert-butyl ester
6456-74-2

Glycine tert-butyl ester

Allyloxycarbonylamino-acetic acid (3aR,5R,6S,6aR)-5-dimethylaminomethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester
145147-49-5

Allyloxycarbonylamino-acetic acid (3aR,5R,6S,6aR)-5-dimethylaminomethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

Aloc-Gly-Gly-OtBu
145147-53-1

Aloc-Gly-Gly-OtBu

Conditions
ConditionsYield
lithium bromide In dichloromethane at 20℃; for 24h;98%
lithium bromide In dichloromethane at 20℃; for 24h; Rate constant; other carbohydrate ester of N-protected amino acids, other amino acid esters; uncatalyzed reaction;98%
Glycine tert-butyl ester
6456-74-2

Glycine tert-butyl ester

6-methyl-2,4-pyrimidine-diyl dibenzoate
155632-06-7

6-methyl-2,4-pyrimidine-diyl dibenzoate

A

6-Methyluracil
626-48-2

6-Methyluracil

B

hippuric acid tert-butyl ester
19811-56-4

hippuric acid tert-butyl ester

Conditions
ConditionsYield
In dichloromethane for 0.5h; Heating;A n/a
B 98%
...Expand
Glycine tert-butyl ester
6456-74-2

Glycine tert-butyl ester

(1S)-N,N-bis(1-methylethyl)-7,7-dimethyl-2-thioxobicyclo[2.2.1]heptane-1-methanesulfonamide
213532-59-3

(1S)-N,N-bis(1-methylethyl)-7,7-dimethyl-2-thioxobicyclo[2.2.1]heptane-1-methanesulfonamide

(1S)-1,1-dimethylethyl 2-(N,N-bis(1-methylethyl)-7,7-dimethyl-1-methanesulfonamidobicyclo[2.2.1]hept-2-ylideneamino)ethanoate

(1S)-1,1-dimethylethyl 2-(N,N-bis(1-methylethyl)-7,7-dimethyl-1-methanesulfonamidobicyclo[2.2.1]hept-2-ylideneamino)ethanoate

Conditions
ConditionsYield
In toluene for 48h; Heating;98%
Benzophenone imine
1013-88-3

Benzophenone imine

Glycine tert-butyl ester
6456-74-2

Glycine tert-butyl ester

N-(diphenylmethylene)glycine tert-butyl ester
81477-94-3

N-(diphenylmethylene)glycine tert-butyl ester

Conditions
ConditionsYield
In dichloromethane at 20℃; for 24h;98%
Glycine tert-butyl ester
6456-74-2

Glycine tert-butyl ester

(2R,3S)-3-endo-benzyloxycarbonyl-bicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid
581100-26-7

(2R,3S)-3-endo-benzyloxycarbonyl-bicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid

(2S,3R)-3-endo-(1-tert-butoxycarbonyl-methylcarbamoyl)bicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid benzyl ester

(2S,3R)-3-endo-(1-tert-butoxycarbonyl-methylcarbamoyl)bicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid benzyl ester

Conditions
ConditionsYield
With dmap; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 0 - 20℃; for 13h;98%

tert-Butyl glycinate Specification

The Glycine,1,1-dimethylethyl ester, with the CAS registry number 6456-74-2, has the systematic name of tert-butyl glycinate. It is a kind of air sensitive chemical, and belongs to the product categories of Miscellaneous and Telmisartan. And the molecular formula of the chemical is C6H13NO2.

The characteristics of Glycine,1,1-dimethylethyl ester are as followings: (1)ACD/LogP: 0.40; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.44; (4)ACD/LogD (pH 7.4): 0.12; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 20.53; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 29.54 ?2; (13)Index of Refraction: 1.434; (14)Molar Refractivity: 35.12 cm3; (15)Molar Volume: 134.7 cm3; (16)Polarizability: 13.92 10-24cm3; (17)Surface Tension: 31.6 dyne/cm; (18)Density: 0.973 g/cm3; (19)Flash Point: 20.7 °C; (20)Enthalpy of Vaporization: 38.27 kJ/mol; (21)Boiling Point: 145.7 °C at 760 mmHg; (22)Vapour Pressure: 4.8 mmHg at 25°C. 

Uses of Glycine,1,1-dimethylethyl ester: It can react with benzaldehyde to produce benzylidene t-butoxycarbonylmethylamine. This reaction will need reagent anhydrous magnesium sulfate, and the menstruum benzene. The reaction time is 0.5 hours with ambient temperature, and the yield is about 75%.   

You should be cautious while dealing with this chemical. It irritates to eyes and skin. Therefore, you had better take the following instructions: Wear suitable protective clothing, gloves and eye/face protection, and if in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.   

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: O=C(OC(C)(C)C)CN
(2)InChI: InChI=1/C6H13NO2/c1-6(2,3)9-5(8)4-7/h4,7H2,1-3H3
(3)InChIKey: SJMDMGHPMLKLHQ-UHFFFAOYAE

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