DI-TERT-BUTYL IMINODIACETATE Chemical Properties

Melting point:

38-42 °C(lit.)

Boiling point:

298.0±25.0 °C(Predicted)

Density 

1.011±0.06 g/cm3(Predicted)

Flash point:

>230 °F

storage temp. 

2-8°C(protect from light)

solubility 

soluble in Methanol

form 

powder to lump to clear liquid

pka

4.52±0.20(Predicted)

color 

White or Colorless to Almost white or Almost colorless

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

WGK Germany 

3

HS Code 

29224999

MSDS

• Language:English Provider:SigmaAldrich

DI-TERT-BUTYL IMINODIACETATE Usage And Synthesis

Chemical Properties

White to tan solid

Uses

Di-tert-butyl iminodiacetate may be used as a reagent in the synthesis of:

• multi-carboxylic acid-containing carbocyanine dyes
• monosubstituted difunctionalized polyhedral oligomeric silsesquioxanes (POSS) monomers
• multigenerational fluorinated dendrimers
• 2,6-dipyrazol-1-ylpyridine derivatives

It may also be used for the preparation of di-tert-butyl N-(4-allyloxy-4-oxobutanoyl)iminodiacetate.

General Description

Di-tert-butyl iminodiacetate is a secondary amine.

Synthesis

The general procedure for the synthesis of di-tert-butyl iminodiacetate from tert-butyl chloroacetate is as follows: in a 250 mL three-necked flask equipped with a thermometer, condenser tube and mechanical stirring device, 120 mL of methanol was added. Under continuous stirring, 120.0 g of tert-butyl chloroacetate (0.8 mol) was heated to 65 °C and 5.1 g of ammonia (0.3 mol) was slowly passed through. The reaction was carried out for 2 hours and then continued to hold the reaction for 5 hours. After the reaction mixture was cooled to room temperature, it was filtered to remove the resulting white solid ammonium chloride. The filtrate was concentrated by rotary evaporation to recover about 110 mL of methanol. The concentrated residue was cooled to 0 °C to induce precipitation of the product. The precipitate was collected by filtration to give 23.3 g of di-tert-butyl iminodiacetate with a melting point of 41 °C.

IC 50

Non-cleavable Linker

References

[1] Patent: CN108191686, 2018, A. Location in patent: Paragraph 0040-0073

DI-TERT-BUTYL IMINODIACETATE(85916-13-8)Related Product Information

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• diisobutyl terephthalate
• ISOBUTYL P-TOLUENESULFONATE
• DIISOBUTYL PHOSPHITE
• Pinacol vinylboronate
• Iminodiacetic acid
• Iminodibenzyl
• Iminodiacetonitrile
• DI-TERT-BUTYL IMINODIACETATE
• N,N-BIS(T-BUTYL-4-CARBOXYMETHYL)AMINOETHANOL
• 4-(N-BOC-AMINOXYACETAMIDO)BENZYL ETHYLENEDIAMINETETRAACETIC ACID, TETRA(T-BUTYL) ESTER
• N-[2-[2-[2-[BIS[2-(1,1-DIMETHYLETHOXY)-2-OXOETHYL]AMINO]-5-METHYLPHENOXY]ETHOXY]PHENYL]-N-[2-(1,1-DIMETHYLETHOXY)-2-OXOETHYL]-GLYCINE 1,1-DIMETHYLETHYL ESTER
• N-[2-[2-[2-[BIS[2-(1,1-DIMETHYLETHOXY)-2-OXOETHYL]AMINO]-5-BROMOPHENOXY]ETHOXY]-4-METHYLPHENYL]-N-[2-(1,1-DIMETHYLETHOXY)-2-OXOETHYL]-GLYCINE TERT-BUTYL ESTER
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• 3-BENZYLSULFANYL-2-(TERT-BUTOXYCARBONYLMETHYL-AMINO)-PROPIONIC ACID TERT-BUTYL ESTER
• N-(5-AMino-1-carboxypentyl)iMinodiacetic Acid Tri-t-butyl Ester
• DI-TERT-BUTYL-2-BROMOETHYLIMINODIACETATE
• [[(S)-2-(BIS-TERT-BUTOXYCARBONYLMETHYL-AMINO)-PROPYL]-(TOLUENE-4-SULFONYL)-AMINO]-ACETIC ACID TERT-BUTYL ESTER